Single mother hires an escort for her son's 18th birthday. She learns her son had mother-son fantasies and comes to grips with her own desire in this area.
Story Codes: (MF, consensual, incest, anal, oral, voy, exhib)
CONTENT CAUTION: This story does contain depictions of: Incest and Prostitution. If either of these topics offends you please don't read any further.
Jennifer was a 36 year old woman with one son. She was 18 when she gave birth to James. Upon her boyfriend learning of the pregnancy he would have nothing to do with her. Her parents and several of her friends told her she should get an abortion, but she had not listened. Being a single mother had not been easy but she loved her son, whom she had named James, and had struggled to make a life for the two of them. While not easy to accomplish she had been a loving mother and James was soon to officially become a man. His 18th birthday was now only four weeks away. Jennifer was excited for him wanting it to be a very special occasion.
During James' journey toward becomming a man Jennifer had been the model mother. She had been active in his school activities while working full time. While raising James, Jennifer had risen to the position of Executive Secretary to the CEO of a successful tech company.
Jennifer was well aware of the fact her current position was due in part to her physical looks. When people failed to give her credit for her mental abilities claiming her success was due in large part to her good looke, she had always retored by saying if it was her looks that got her noticed it was her brains that would get her the job. There was no dispute amongst the executives at the company that Jennifer was indeed the brains behind her boss. She kept him organized and at the top of his game. He had tragically lost his wife to cancer five years earlier and had even hinted to Jennifer he would like to see her socially. When this happened she had told him she was flattered, but she didn't want to ruin their relationship.
Secretely she was flattered by his interest and had to give him credit for trying, but she was serious about her job and didn't want to screw it up with an office romance that could likely end in her loosing her job if they decided it could not work between the two of them. Her boss didn't give up easily, but after a few more attempts he seemed to respect her dedication to her job and didn't pursue the issue any further. She would still catch him looking at her from time to time and each time he was caught he would laugh and say, "Jennifer you're a beautiful woman and after all I am just a man. You never said I couldn't look."
Having been the 'Pretty Girl' her whole life Jennifer had become accustom to attracting the interest of men. She knew her boss was half joking and half sincere. They both recgonized they were good for each other and had a great working relationship. She didn't mind his flirtatious joking with her and she liked the reinforcement that she could still attract the attention of a very handsome man. She knew he would never force himself on her or use his position to coerce her into doing something with which she was uncomfortable.
More than once she had looked in the mirror and wonderd if she was unconsciously teasing him. She always dressed professionally, but she had noticed most of her blouses had a neckline that plunged a little more than maybe those worn by the other secretaries and her skirts were a little tighter and quite a bit shorter. She always wore heels with at least a four inch heel. She was proud of her body. Her C cup breasts were firm and she always thought they were the perfect size for her body. She had never once considered having them enlarged. Her shoulder length blond hair was always cute and perfectly styled. Each time Jennifer had considered her attire she concluded she was proud of the way she looked. Even though men had a weakness, she had always enjoyed the attention.
James, her son, had always been a little on the shy side. She had always been pretty out-going and had never understood why her son had not inherited that personality trait. He was a handsome young man, but even though he had dated a few girls in high school, she could tell girls made him feel uncomfortable. She knew he liked girls, but when it came to romance he seemed to freeze. She knew growing up without his father had not been easy and as a woman it was hard for her to have those manly talks with him, a father is supposed to have with his son. James and her father had always been very close and he had been the male influence during James early and then later adolescent years. Jennifer had a strong suspicion her son was still a virgin.
Several times she had tried to bring up the topic of girls, but each time he would get embarrassed and tell her, "Mom I know about girls don't need you telling me about the birds and the bees."
A couple weeks prior to her son's birthday Jennifer asked her boss if they could discuss something personal. He looked up from his desk with a serious look on his face and told her to close the door and come on into his office. He then motioned toward a chair asking her to take a seat.
"Thanks Ben. I hate to bother you with this, but it's about James."
"Is he okay?" Nothing wrong, I hope.
"No, nothing wrong. At least nothing I know of. It's about girls."
Ben grinned and said, "You had me worried there for a minute. I'm not surprised, James is a good looking young man. I imagine he has all sorts of girls after him."
"Yea, I know and I guess that's part of my problem. The fact is he doesn't seem to have an interest in girls. I'm wondering if he might be gay. If he is, that's okay, but I would like to know."
"Why would you think he's gay?"
"He's dated a little. Girls that is, but he's never had a serious girlfriend. He seems to freeze up around girls."
"That doesn't mean he's gay. As I recall James has always been sort of shy."
"Yes, he's always been that way."
"Maybe he just needs a little push in the right direction."
"What sort of push?" Jennifer asked.
"It's possible he needs a woman who will take charge and show him what it's like to be with a confident woman. There's a lot of social pressure on young boys to be the man and take the lead when it comes to dating and that sort of thing. When I was his age I was scared to death to ask a girl on a date. Trust me, it can be quite intimidating, especially if it's a girl he thinks is pretty and feels like she might not share the same level of interest in him that he has for her."
"That never stopped you from hitting on me," laughed Jen. "I guess you don't think I'm pretty. Is that it?"
Grinning he said, "I think we both know how I feel about you. Maybe I should have been a little more discrete but Jennifer you know you're a beautiful woman. I did my best but you broke my heart," he laughed as he slapped his open palm over his heart. "But seriously Jennifer, a man learns to accept rejection as he gets older. I can understand how a young man like James might fear rejection from girls he finds attractive."
"So, you said something about giving him a push in the right direction. Is there something I can do to help?"
"I might have an idea, but I'm not sure you're going to like it."
Jennifer was suspicious, but asked, "Okay, just what is it you have in mind?"
"As I recall his 18th birthday is coming up soon."
"Yes, four weeks from today."
"Don't get mad at me for suggesting this, but you could hire an escort for him for his birthday."
"An escort? You can't be serious."
"Very serious. Now hear me out before you decide I'm crazy. With an escort you can look at their photos and select a pretty girl. You know she will not only go to bed with him she will also know what to do once they're in bed. It won't be like the typical date where he wonders if she will or won't. For a girl like I'm talking about; one he can take to dinner then a hotel it's not going to be inexpensive, but I have a feeling once he gets a taste of a real woman he will have the confidence to take it from there with other girls. An Escort doesn't have to be like a girl he would pick up soliciting on the street. The sort of Escort I'm talking about would give him the girlfriend experience."
Initially rejecting his idea, Jennifer paused and actually thought about what Ben had said. As bad as she hated to admit it, what he said made sense. As she was still thinking Ben added, "On the other hand, if he is gay, and that's a big IF, the escort will be able to determine that and if you wanted she could report back to you. If that's the case, you will at least know why he hasn't had a serious girlfriend."
Again what he was saying made sense. She said, "I'm not crazy about the idea, but it just might work. The problem is I have no idea as to where I would begin. Do you know anyone who has ever hired an escort?"
Ben's silence combined with the look on his face answered her question. In a surprised voice she asked, "You? Seriously?"
Nodding his head Ben said, "Yes and the first time was a little strange. Once I got past that first time I was able to relax and they have all been wonderful girls."
She thought to herself, 'Not only has he done this before, but evidently he's done it several times.'
She asked, "Is there a particular agency you recommend I call?"
Reaching into his center desk drawer Ben pulled out a card and handed it to Jennifer saying, "Ask for Kiki. I think you will be impressed and I'm certain, if he isn't gay, James will like her."
It took Jennifer a week to summon up the courage to call the number on the card Ben had given her. She had gone to the Escort Agency's web site and looked at the photos of the girls working for this particular agency. She found the one named Kiki and was blown away by how adorable she appeared in the photos. Kiki looked like a high school prom queen. Her stats said she was 25, which was older than she looked. To Jennifer she didn't look over 18 or maybe 20 at the most. She had blond hair and Jennifer realized the girl looked a lot like she had when she was in high school. She had gone back to the site several times and each time she looked at Kiki she became even more convinced this was the girl for James. If she hadn't known better she would have sworn the girl was her twin sister from several years earlier.
Jennifer wanted to ask her boss if he had ever hired Kiki, but she didn't have the nerve to ask him such a question. When she finally got the nerve to call she asked if Kiki was available the evening of her son's birthday. The woman she spoke to assured her Kiki was available.
"Would it be possible for her to call me? This is for my son's 18th birthday and I would like to talk to her first."
"That shouldn't be a problem. Just give me a number and when you want her to call."
Jennifer gave the woman her mobile number and said she could call anytime after 6:00 PM.
"I'll give her the message. Do you want to wait until you talk to her to reserve her for that date?"
"No, I'll go ahead and book her. I want to make sure I get her and she is available for that day."
"How long do you want her?"
"I've never done this before. What do you suggest?" asked Jennifer.
"The minimum is one hour, but it sounds like this is a special occasion. My suggestion is to have Kiki start at 7:00 and spend the entire night."
"All night? How much would that be?"
"As I said, it sounds like a special occasion. It would be $3,000 for overnight."
Jennifer did some quick calculations in her head and said, "Okay, I guess let's do all night. He will only have one 18th birthday."
The woman took Jennifer's information and told her to call back with a location for Kiki to show up. As she hung up the phone Jennifer hoped this girl was worth that much money. She knew there would also be a tip expected on top of the 3 grand.
It was almost 8 o'clock that evening when her mobile phone rang. Caller ID showed the number as Private. She almost didn't answer then remembered Kiki was supposed to call and maybe this was her. Pressing the Send button she answered, "Hello."
She heard a female voice ask "Is this Jennifer?"
"Yes it is."
"This is Kiki. You called the agency and asked for me to call."
"Oh, yes, thank you so much. I guess you're going to spend the night with my son."
"That's what I have been told. I was told this is his 18th birthday. Is that correct?"
"Yes, that's right." Jennifer went on to explain how James was shy and she suspected he was still a virgin and there was a possiblity he might be gay. She asked if Kiki would mind calling her after the date and let her know how it went. The girl said she could do that. When Jennifer had finished Kiki said, "I'm sure he's just shy. I'm looking forward to meeting him. I assume we will go to dinner then spend the night getting to know each other?"
Jennifer had to smile hearing the girl phrase it in that manner. "Yes that's what I had in mind. He may have different ideas and if this is something he doesn't like, I understand. I will pay you the full night."
"A lot of guys his age like what we call the 'girlfriend experience.' It's much more laid back and like a regular date."
Jennifer remembered Ben mentioning that and said, "That shounds good."
They talked a little longer then said good-bye agreeing to talk again before James' birthday.
Three days prior to his birthday, Jennifer called Kiki and gave her the name of the hotel where she had reserved a suite. They agreed it would be easier for Kiki and James to meet at the hotel then leave from there to go eat. Kiki promised to call Jennifer the day after James' birthday to let her know how it went.
The day before his birthday Jennifer was having second thoughts wondering if this idea for her son's birthday had been a mistake. She had spent a lot of money on her son's birthday. She didn't mind the money so much, but she didn't want her son to be upset with her for sticking her nose into this area of his personal life.
Jennifer printed a few of Kiki's photos from the web site and wrapped them in a box with some other papers. She was hopeful the photos were recent and that Kiki actually did look like the photos on the web site. She had considered showing them to her boss and asking him if she was as pretty as the photos showed. Even though he had given her Kiki's name she had been too embarrassed to talk to him about what she had set into motion.
Jennifer and James were eating dinner the night before his birthday when Jennifer asked, "Hon, you don't have plans for tomorrow night, do you?"
"Not yet. Why?"
"Can you do me a big favor and keep it open? I have something special planned for your birthday."
"Like what?"
"I'll tell you tomorrow. I got you a special gift and need you to keep tomorrow night open."
"Okay, Mom." With a grin on his face he asked, "What did you get me, a new car?"
Grinning she said, "I can say it's not a new car, but it's a surprise and you have to wait until your birthday to find out."
"Okay, but you know I hate waiting."
"I know, but I'm pretty sure this will be worth the wait. Trust me."
Jennifer could see the excitement on her son's face. She liked giving him gifts and hoped this one didn't blow up in her face.
She wondered why her parents had not told her what they were getting him. With James being their only grandchild they always went overboard when it came to the gifts they gave him. She wondered what they might have gotten him, but she was almost certain whatever it was it wouldn't be the same as what she had gotten him.
That night Jennifer lay in bed unable to sleep. She was thinking about what she was sure would be her son's first time with a woman. She remembered her first time and how special it had been for both her and the boy who took her virginity. She figured loosing one's virginity was better for the boy since he didn't have the pain of having his hymen torn. She remembered her second time with a boy had certainly been better than the first.
As she thought of her son in that hotel suite with Kiki her fingers drifted to her clit. She had no way of knowing at that same moment, only a few feet away, her son was in his own room with his hand wrapped around his hard cock slowly stroking it as he watched a porn video on his computer.
James wanted nothing more than to get into a girl's panties, but each time he had tried he had been afraid of rejection. He had several friends who were girls, but had never had a real girlfriend. Girls had always been very intimidating, but the girls on the Internet would never reject him. He could jerk off without fear of them turning him down.
He enjoyed stroking his cock and when he did cum it always felt great. He kept telling himself one day he would find a girl and find out what it felt like to have his cock inside another person instead of his hand. The videos he watched made it look incredibly fun. When he could hold back no longer he came hard and shot his load of cum into a tissue. He milked his cock and wiped the last drop he could squeeze out with the tissue before tossing the soggy tissue into his trash basket then climbing into bed. He always felt better after he jerked off. Now his thoughts turned to what his mother could have gotten him as a gift for his birthday that would require him to be home all night.
As her son was going to sleep Jennifer's fingers were rubbing little circles over her stiff little clit. She had several fantasies she liked thinking about as she lay in bed at night. One of her favorites involved her boss. She had always had fantasies of him calling her into his office and telling her to close his door. She would do as he instructed. She liked working in an office and liked dressing up for Ben. She liked dressing for him and knew he liked her short skirts and heels. Her blouses often showed the inside swells of her breasts. She knew she probably would never let him fuck her, but she did enjoy teasing him and seeing his reaction. She had not started intentionally teasing him until a while after his wife had died. She thought it brightened his day seeing her looking sexy. She had overheard some of the executives comment when they thought she was too far away to hear. Ben's comments had never been crude, but she could feel the pride in his comments when he mentioned her.
She had taken note of the way Ben looked at her. He had always been very professional, but she could tell he found her attractive. She thought she wanted him to drop the employee/employer fa�ade and see her as a woman, but when he had tried she got nervous and stopped it before anything happened. A few times when she thought about it she sort of wished he had pushed her a little harder and had not been such a gentleman. Learning he uses an escort service made her even more frustrated. She knew she could supply that need all men crave.
Pushing her fingers between her lips into her soaking wet pussy she imagined her fingers were was Ben's cock entering her. She could almost feel him inside her as her orgasm flooded over her and she let out a cry of ecstasy. Her pussy clamped down on her fingers as she pushed them deep into her pussy. She knew James might have heard her, but she needed that release. As she calmed and was enjoying the afterglow she almost wished James had heard her. She wondered what he would think if he knew his mother just rubbed herself to a wonderful orgasm.
Jennifer woke up early Saturday morning. Her first thoughts were memories of what had happened 18 years earlier that same day. She thought back to being in the hospital and how her legs had been spread open with what seemed like the entire hospital looking at her pussy. At that moment she remembered how much it hurt and she didn't care if they televised it nationally just as long as they made it stop hurting. Her mother was there with her giving her support the entire time. She remembered how once James had struggled to make his way out of her body and the nurse placed him on her bare skin. She remembered being focused entirely on the precious life that had come from her body. Giving birth to her precious son had been the single most joyful highlight of her entire life. That day had been filled with some of her most precious memories. She remembered the tears of joy in her mother's eyes as James took his first breath and how wonderful the sound of him crying had been. Giving birth to him had been the most painful thing she had ever undergone, but all that pain was quickly forgotten when the nurse laid James on her bare skin.
She knew they wanted mother and child to have the skin to skin contact for bonding. James was wiggling around and felt incredible on her skin. Thoughts of James' worthless father couldn't have been further from her thoughts as she and her mother marveled at the miracle of birth and how she was now a mother.
It was now Eighteen years later, and this would be the day her boy became a man in more ways than just age. She was sure she was more excited regarding her plans for the day than James was, but she was pretty sure that would change once he met Kiki. At least that was what she hoped.
Jennifer had bought James a new pair of slacks and dress shirt for his birthday. He would later learn they were intended for his date that evening. She hurried getting out of bed, it was going to be a big day and she had lots to get done.
Jennifer was cooking breakfast when James came out of his bedroom and into the kitchen. When she saw him she turned, threw her arms in the air and yelled, "Happy Birthday!"
He gave her a cute grin and said, "Thanks Mom. I really made it, I'm finally an adult."
"Yea, 18 and ready to take on the world."
"Well, at least 18. I'm not so sure about taking on the world. At least not today."
"I'm going to bake you a cake after we finish breakfast. If you have anything you want to do, please be home no later than 5 o'clock. Okay?
"Sure Mom. I'll probably just hang out here, if that's okay."
"Okay? Absolutely! I love having a man around the house."
He gave her another grin as she placed a plate of eggs, bacon and toast in front of him. She poured him a glass of juice then fixed herself a plate before sitting down to eat with him. "You're such a handsome man. I can't believe the girls haven't swarmed all over you."
"Mom, please."
"I'm serious. You really are a very handsome man."
"Thanks, but girls scare me. I wish they were all as easy to talk to as you."
"Girls shouldn't scare you. They are just as nervous as you are. Once you understand that, it will be a lot easier to talk to them. You have a lot of girls you're friends with. Isn't there one of them that you have thought about asking out?"
"Sure, and you know I've been on a few dates. The problem is after we go out a couple times they don't seem to want to go again. I don't know what I'm doing wrong. There's one I really would like to…" He paused then as if dismissing the idea he said, "But it would never work."
She wanted to press the issue and find out who this girl was, but she could tell he didn't want to talk about her. Instead she said, "I'm confident you will figure it all out. I think you just need to believe in yourself."
They sat there eating in silence when Jennifer said, "Honey, do you mind if I ask you something? It's very personal?"
James had no idea what she wanted. Had she heard him jerking off the night before? If that's what it was, he would simply die. "What's it about?"
"This is hard to ask, and I really don't want to embarrass you." Jennifer was stumbling trying to come up with a reason for her question when she said, "I was at the doctor a couple days ago and he asked if you've been… well if you've been with a girl?"
"Mom! Seriously?"
"Honey I know it's hard to talk about and since you don't have a father to talk to, I thought maybe we should talk."
"No, Mom. I've never been with a girl, at least not like what you're talking about."
"Oh – well okay. You do know I'm here if you ever want to talk."
"I know Mom, it's just hard to talk about that."
"I understand." Deciding to change the subject she asked, "What kind of cake do you want?"
"How about that one you make with the chocolate fudge in the middle?"
"I can do that. I've even got some candles. Grandma and Grandpa are planning on coming over later this afternoon."
She saw James smile when she told him this. He had always had a special relationship with his mother's parents. James pitched in and helped his mother clean the kitchen then went back to his room.
As she was baking the cake she was more certain now than ever she had been correct about James being a virgin. Now if he would just be receptive to Kiki.
Jennifer had two gifts for James, but for obvious reasons she had only given him the new outfit she had purchased for his date. As Jennifer had suspected, her parents were true to form and gave James a sporty, but used, two seater convertible. The car had been well taken care of and looked almost new. James had been speechless when his grandfather handed him the keys. Jennifer enjoyed seeing her son so happy, but still told her parents it was too much.
Jennifer had let her partents know she had made plans for James for later that evening, but for obvious reasons had not told them what the plans involved. After they all enjoyed a piece of cake and ice cream the grandparents excused themselves leaving Jennifer and James alone.
Jennifer asked James to have a seat telling him she needed to talk to him and told him she had one more very special birthday gift for him. As she sat across from him she said, "Son, you're officially a man today. I hope you don't get mad at me, but I arranged for a special gift that will be our own little secret."
James wasn't sure what to think. His mother had already given him the clothes and his grandparents had given him a fantastic car. What could his mother be talking about?
"I realize it hasn't been easy for you not having a father around. I've tried my best to fill in, but we both know how that can be a little awkward at times."
James nodded his head grinning as he remembered some of those awkward conversations. Jennifer went on by saying, "I don't know how to say this any other way other than just come out with it. My boss suggested a gift for your 18th birthday and… well, I've arranged a special date for you tonight. She's an escort and you are to meet her at a hotel where I have reserved a suite for you. I've also made dinner reservations at that really nice Italian restaurant you like. After you eat you can take her for a walk on the beach, go straight back to the hotel, or anything you would want to do on a date. The big difference is this girl is expecting to spend the entire night with you."
Jennifer paused to allow a few moments for what she had just said register with James. James said, "Mom… what exactly are you saying?"
This is when she retrieved the package she had wrapped earlier and handed it to him. He held it making no move to open it, while at the same time staring at his mother letting what she had just told him sink in. She said, "Go on Honey, open it. I think what's inside will answer most of your questions."
James waited a few more moments then began to slowly tear the wrapping paper from the package. He then opened the box as if it contained a rattlesnake he was half way expecting to jump out and bite him. Inside he first found a brochure from the hotel with a photo of one of the suites. His mother explained it was similar to the one she had reserved. Next was a layer of crumpled blue tissue paper. When he removed it he found three color photos of Kiki. Jennifer saw him grin then look up at her. He laughed and said, "Mom, you had me going there for a minute. I thought you were serious. Where did you get the pictures of the smoking hot babe? If you were going to set me up with some hot fox, she would certainly be a great choice! Do you mind if I take my new car for a spin?"
"Honey, this isn't a joke. She's the girl you are to spend the night with." Jennifer glanced at her watch then said, "She's meeting you at the hotel in two hours. Her name is Kiki. She is yours for the night."
"Mom, there's no way I'm spending the night with a girl as gorgeous as this. Be serious and confess this is all a big joke."
"No, it's not a joke. She's an escort and she IS your date tonight."
"You're serious. Your really not kidding, are you?"
"No, not at all. I want you to go and have fun. There is more in the box. You need to keep digging."
James looked back in the box and saw another layer of crumpled tissue paper. Upon removing it he saw a box of condoms and could hardly believe what this all meant. This was so surreal. He looked back at his mother and said, "This really isn't a joke, is it?"
"No Honey. You have a beautiful young woman who is anxious to introduce you to the pleasures a woman can give a man."
"Mom, I don't know what to say."
"Get your handsome ass ready for your date. This is why I got you that new outfit. Get in the shower and get cleaned up. You have less than two hours. I've already paid for everything, but I have some cash for you to pay for dinner and give the rest to Kiki tomorrow morning as a tip. Now get a move on. You don't want to keep her waiting."
"I don't know what to say or do."
"Just say thanks Mom, then get your ass moving."
With a huge grin he said, "Thanks Mom," then gave her a bone crushing hug. Jennifer was a little shocked when he hugged her and she felt the hard bulge in his pants pressing against her stomach. He then headed off toward his bedroom.
Jennifer could see the excitement on his face as she handed him an envelope saying, "This is for dinner and Kiki's tip. Have fun Baby and I don't want to see you before noon tomorrow. I've already arranged for you to have a 1:00 o'clock checkout."
"Thanks Mom! I still can't believe you did this."
"Just have fun and when I see you tomorrow you will know what it's like to be a man and be with a woman."
Jennifer saw her son blush a little then turn and head outside to his new car. She watched as he drove away and didn't look away and head back into the house until he was out of sight. She sat on the sofa and thought it had gone better than she feared it might. Now the rest was up to James and Kiki. She could hardly wait to hear from Kiki.
James loved his car. It was a two seat convertible. Sure it was a few years old, but it looked almost new. The car was red with tan leather interior. It had a standard transmission and he loved shifting through the gears. As much as he was in love with his new car, his mind was mostly on what his mother had just given him. The girl in the photos was gorgeous! He was having a hard time believing his mother had actually hired an escort for him. He didn't have to worry about her turning him down when he asked her out and better yet he never would have been brave enough to have asked a girl as pretty as her out. There was no way a girl looking like her would ever go out with him. What would he talk to her about? What would they do all night? His mother said she was spending the night and obviously his mom expected them to fuck, since she had actually included a box of condoms. He knew he should be embarrassed by what she had done, but he was too horny and excited thinking about the night.
He was hoping his mother hadn't noticed his dick was hard. He had been so excited and hugged his mother that he had not even realized he was hard until he was hugging her and it was too late. She was so short his hard dick had been pressed into his mother's stomach. He was pretty sure she hadn't noticed.
He pulled up in front of the hotel. A valet about the same age as James came to collect the keys. The valet grinned and said, "Sweet ride."
"Yea, I just got it."
As the valet drove his new car off to park it, James pulled the piece of paper his mom had given him. On it was the reservation information along with instructions to get registered then go to the suite. Kiki would arrive and she knew the suite number. She would meet him there and then they would leave and go to the restaurant where his mother had already made reservations.
James got some strange looks as he checked in at the front desk. He figured they were not accustom to seeing an 18 year old check into a suite by himself. After getting the key he headed toward the elevators. Glancing at his watch he saw he only had 15 minutes before his date was to arrive.
Getting on the elevator, James sensed another person get on. Without looking he asked, "Which floor?"
A feminine voice said, "If you're James, I'm headed to the same floor as you."
He caught a faint whiff of what smelled like flowers. It was the perfume she was wearing and it smelled great. He turned to look at the woman and saw immediately it was the girl in the photos his mother had given him. She looked even better in real life than she did in the photos. He wasn't sure what he had been expecting. In the photos she was wearing a very tiny bikini. Now she was dressed in a blouse and skirt with sexy heels that were not too tall. He guessed they had maybe a three inch heel. She had shoulder length blond hair, a necklace and gold hoop bracelets. She wasn't dressed in the manner James would have expected. She looked very normal and best of all, she was beautiful.
The girl smiled at him and saw he was speechless. She extended her hand and said, "I take it you're James. I'm Kiki."
"I-I-I-I recognize you from the photos."
She gave him a big smile and said, "I hope you're not disappointed."
"N-n-n-n-o-o-o, not at all. You are very pretty."
"Thank you James. I must say you're not too bad yourself. You're actually a very handsome man."
"How did you know it was me?"
"I could tell. You don't see too many guys your age checking into a hotel alone. I've been in the lobby waiting for a few minutes."
"I'm sorry. I didn't mean to keep you waiting."
"No problem. I like being early and I've been looking forward to tonight."
"Really?" exclaimed James.
"Yes really. You have no idea how refreshing it is to be with a man like you."
James wasn't sure what she meant, but he liked the way she had said it. The elevator stopped on their floor. They headed to the suite and James opened the door letting Kiki in first. As she passed him she said, "A real gentleman. I like that." She let her finger tips caress his arm as she passed. Her touch sent a chill up James' arm. He realized his dick was once again hard. He hoped she hadn't noticed, but she was hot and he couldn't help it!
They looked around the room and it was very nice. He stepped into the bedroom and was checking things out when Kiki came up behind him and touched him saying, "Nice bedroom. I can hardly wait."
James had to adjust his dick before turning to follow Kiki back into the living room. He tried to be discrete as he adjusted his dick, but out of the corner of her eye Kiki had seen him. She had to grin to herself. She had this effect on men and liked seeing their arousal upon seeing her.
James asked, "You hungry?"
"Starved."
He smiled and said, "I've got reservations at that really nice Italian restaurant downtown."
Kiki took hold of his elbow and said, "Let's go handsome."
Kiki commented on James' new car telling him all the girls would love it. He told her he had just received it for his birthday.
They were escorted to their table. It was situated back in the corner giving them a little privacy. James thought it would be a nice place to sit with your girlfriend, but Kiki wasn't really his girlfriend. He had liked that every man who had seen them enter gave his date a good look. He could see the envy in their eyes. He knew they wished they were in his shoes. Kiki hadn't even seemed to notice. Her full attention was on James.
They were given menus and Kiki immediately put her's to the side. She said, "I like my date to order for me, if you don't mind."
"But I don't know what you like."
"If you order it, I know I will like it."
James ordered them both lasagna and salads. He wanted to order wine, but he would have to wait another three years before he could legally do that.
As they waited for their food Kiki began talking asking him about his hobbies and what he liked in the way of music. James found she had a way about her that made it easy to talk to her. Even though her looks had been very intimidating, he found himself opening up to her telling her all about himself. He asked her a few things, but most of the conversation was her wanting him to talk about himself.
They split a dessert and James liked that they were eating from the same dish. Their table was small and rather than being seated across from each other, Kiki was seated next to James. As they were eating their dessert she kept touching his leg with her hand. Her touch felt wonderful, but was making James very uncomfortable as it wasn't allowing his cock to relax. He remained hard throughout the entire meal. He was concerned he might blow a load right there in the restaurant.
Somehow James was able to maintain control until they paid the bill and got out of the restaurant and back into his car. Kiki was fun and made James forget the fact she was being paid to spend the night with him. With Kiki it felt as if she was like any of the few girls he had dated before. The exception was she was a lot more fun and a whole lot better looking.
Kiki was impressed with James. He was a handsome young man. At first he had been overly nervous. She had dealt with men like him before. She knew she made men nervous. Some were nervous because of her looks and others were nervous because they were paying her for her time. There were still others who were nervous they were going to be seen with her by their wives or girlfriends. James was different. His mother had hired her. That was not very common, but she had been hired by fathers for their sons before. The 18th birthday was one that parents seemed to think their son should learn what it's like to have sex with a woman. Kiki had always enjoyed these dates.
She knew getting a man to talk about his favorite topic – himself – was a sure fire way to ease the tension and make him more comfortable. She might be an escort, but she wanted a happy customer and wanted to enjoy herself at the same time. She had noticed there was something about someone else paying her fee that also helped the man she was with to relax. She had already been paid by her agency, so that part of the business transaction was out of the way. She had sent a text message to her agency letting them know she was fine and that James would be no problem regarding her safety.
James had suggested a walk along the beach and Kiki liked the idea. He parked and she kicked off her heels. He removed his shoes and socks then rolled up his pants legs. They were walking toward the beach. The sun had set and there were very few people remaining from the earlier beach crowd.
As they walked toward the water she was close to James and let her hand brush against his a few times. It didn't take long for him to take the hint and take hold of her hand. She loved walking along the edge of the water as the surf would wash over her feet. They hadn't walked along the water too far before she felt James move the hand holding her's behind her back. He released his hold on her hand and put it on her waist. He pulled her in closer toward him.
Kiki smiled as she enjoyed his touch on her. They had walked quite a ways when Kiki stopped and tuned toward James. He looked down at her and saw her looking up at him. She said, "I don't know about you, but this is my favorite time of the day to be on the beach."
"Yes, it's nice. It's even better with a pretty girl," said James.
She stood there looking up at him. Neither of them spoke for the longest time. Kiki then leaned in toward him and James got the idea. He put his arms around her and kissed her. The first two or three kisses were a little tentative, but then James became more aggressive and kissed her with much more passion.
Kiki felt his hardness pressing against her. At first she ignored it, but then she dropped her hand to squeeze his hard shaft through his pants. She said, "Baby, you really do have a big cock."
"Sorry about that," James said, somewhat embarrassed.
"You have nothing to be sorry about. I like a man with a big cock."
She began to unzip his pants. James almost went into a panic as he looked to see if anyone was nearby who might see what she was doing. There was nobody even close, but no woman had ever done anything like this to him. He looked down at Kiki who was still looking up at him as her hand entered the opening in his pants and was now touching his cock through his boxers. He felt her fingers opening the fly in his boxers and felt the first touch of a woman's bare hand come into contact with his cock. Sure he was sure his mother had touched him there when he was little, but that had been years ago. This was a beautiful adult woman whose fingers were now wrapped about his hard flesh. Her hand was slowly stroking and squeezing his male organ.
Kiki said, "Honey, I think you better take me back to your hotel room. Your cock feels wonderful and I need to see and taste it."
James was sure he was going to blow cum all over her hand. Kiki sensed his level of arousal and slowly withdrew her hand. As their lips met for another passionate kiss she zipped his pants closed. They then made their way back along the beach. They were not running, but they were certainly moving faster than they had when they walked to where they had been. They stopped a few times along the beach to kiss as they made their way back to the car. Once there Kiki brushed the sand from her feet and slipped on her heels while James rolled his pants down and put his shoes on, not bothering to put his socks on.
Upon arriving at the hotel, James tossed the valet his keys as Kiki didn't wait for him to open her door. The elevator ride to their floor seemed as if the elevator had gone into slow motion.
When they were finally in the suite and the door closed and latched behind them, James took Kiki in his arms and kissed her hard. Kiki felt almost like he might bruise her lips. She always liked the passion a young man demonstrated. When he released her she began unbuttoning his shirt. She pulled it form his pants and finished unclasping the buttons. When she opened his shirt she found his chest was muscular and smooth. Many men had a mat of thick hair on their chest, but James was bare-chested. This was just the way she liked a man.
James kicked off his shoes as Kiki began to unbutton her own blouse. She pulled it form her skirt and slipped it off her shoulders, letting it fall down her arms. James saw she was wearing a lavender satin and lace quarter cup bra. Her breasts were not overly large and the bra offered them support from below. Her pale pink nipples were fully exposed and had James' full attention.
Kiki saw the excitement in his eyes as he looked at her breasts. She liked the way men responded to her sexy bra. James stood there as if he had been frozen. Kiki said, "Do you want to touch me?"
His eyes rose to meet her's as he nodded and said, "Yea."
"I'm here for you. You can touch me wherever and however you want. Just so you know, I like having my nipples sucked on."
James grinned then slowly raised his hands to gently touch her bare breast flesh. Kiki closed her eyes and let out a sigh when he touched her. She said, "Yea, just like that. Pinch my nipples. They are very sensitive."
James did as she asked. He gently pinched her nipples and felt them harden under his touch. This was the first woman he had touched like this and felt her nipples get hard. He then leaned forward and kissed her nipples before taking them between his lips and tasting them. His hands went to her skirt and before he could damage the garment Kiki said, "Honey let me do that."
Moments later her skirt was pooled on the floor at her feet. She stepped out of it and was now wearing her bra, matching thong and heels. James baked away to get a good look at her. Before he could close the gap again Kiki was on her knees at his feet. She removed his shoes then unfastened his belt and opened his pants. Pulling them down she helped him as he stepped out of them. Dressed only in his boxers he looked at the feminine creature on her knees before him.
Her eyes were on his as she took hold of his boxers and began to pull them down to his feet. As she pulled her eyes dropped to get a good look at the man flesh she was exposing. She pulled the elastic away from his body and saw his painfully hard cock bob up and down as she continued to pull the boxers down.
In her line of work she saw every shape, size and color of cocks. Most were short and stubby. Some were long and thin while others were very thick. Some were ungly and some were handsome masterpieces. Regardless of what his cock looked like all cocks had one thing in common. The owner of each was proud of what he had. She knew even though they knew she was lying, they all liked to hear her tell them they had a magnificent cock and how good their cock felt inside her. She had to be quite the actress sometimes, but with James he did have a handsome cock. His glans was perfectly shaped with thick veins running along the shaft. His cock was both thick and long. Kiki preferred thickness over length, but having both was a bonus.
Unlike most of the girls in this line of work, Kiki wasn't an escort for just the money. She also genuinely enjoyed being with a man and having him inside her. Some guys were simply a job and a way to earn money to pay the bills, but something made her believe James was going to be much more. She had a feeling this was going to be a night she would enjoy and remember.
She looked up at James and smiled, then said, "I've been waiting for this all night."
He watched as she extended her tongue and flicked it at across the end of his cock. She then ran the top of her tongue slowly along the underside of his glans making him literally shake from the intensity of her touch. She grinned and asked, "Like that?"
"Uh huh," was all he could say.
He watched as his cock disappeared between her lips and into her mouth. The feeling of the warm wetness of her mouth engulfing his cock was beyond anything he had ever felt. He had watched tons of porn videos and wondered what this would feel like, but never had he ever thought it could feel as incredible as it did.
Cupping his balls in her hand, Kiki squeezed them ever so gently while bobbing her head up and down his long thick shaft. She felt his hands on her head at almost the exact same time she heard him groan then push his cock further into her mouth. With her hand on his scrotum she could feel the pulsations of his body on not only her hand but also her tongue as his cum forcefully jetted into the back of her mouth.
She liked the taste of cum and didn't mind swallowing it, but James cock was deep enough into her mouth she was unable to taste him. As for swallowing him there is no way she would deny him the pleasure of giving her his cum. She was looking up at him as she held him in her mouth until he began to soften. As he pulled back away from her his cock slipped from between her lips and she gave him a big smile.
Reaching down to her James gripped her arms and lifted her from her knees to her feet. She wrapped her arms around him saying, "I hope you enjoyed that, I know I did. You have a really nice cock."
What he did next surprised her. He put his finger under her chin lifting it to give him access to her lips. He kissed her passionately. Kiki had found that very few men wanted to kiss her after they had cum in her mouth. She had always thought it was ridiculous that they wanted her to swallow their semen, but then didn't want to kiss her. She liked that James wasn't like most men. This only helped confirm her earlier suspicions that James didn't see her as a prostitute.
After their lips parted James said, "I've never felt anything like that. It was amazing, no, you are amazing!"
Kiki smiled and hugged him tight. She thought to herself if she ever did find a man she could settle down with and spend her life loving, it would be a man like James.
They stood there for several minutes holding each other, then Kiki felt his cock begin to harden again. That was what she liked about young men, they could recover quickly and keep on going. What they lacked in technique and experience they more than made up for in stamina.
Kiki couldn't resist laughing when James pulled her thong down and saw her freshly waxed pussy. He was like a small child in his amazement of the appearance and softness of her pussy. He asked her if he could eat her pussy. She knew some men liked to eat her, but a lot didn't want to given the fact she slept with a lot of different men. They might eat their wife's pussy or even their girlfriend's, but not her's. She told him, "Sure, if you want to. I'd like that."
He grinned and then looked down at her pussy as she spread her legs offering him better access to her body.
At first he studied her very closely. He had never seen a real woman he could touch and feel, and to be this close he wanted to get a good look. He first pulled her lips apart and saw the moist pink flesh. He thought to himself, 'So this is what a woman's scent is like.' He liked they way she smelled and his cock was once again reacting to his excitement. He looked up at her and asked, "Where's your clit?"
Grinning she took his hand and then guided his index finger until she felt it touch her clit and said, "Right there, that's my clit. If you what to drive me wild, just suck it or flick the tip of your tounge across it. That drives me wild."
He extended his tongue touching it to the small sensitive bump of flesh then flicked it up and down and back and forth, just like she had said. Kiki sucked in a sharp breath of air before saying, "Yea Baby, you've got the idea. Just like that."
He then closed his lips on it and sucked it between his lips. He could taste her juices and liked the way she moved her hips rubbing herself against his face. He moved off her clit and pushed his tongue into her moist depths. He felt her fingers in his hair. She was pulling him against her and saying, "Oh Baby that feels so good. Please don't stop."
Her fingers tightened in his hair and he felt her get even wetter. She cried out and pushed herself hard against his face. He wasn't sure, but thought maybe she had experienced an orgasm. When she relaxed she said, "You made me cum. Nobody ever makes me cum. That felt so damn good."
He grinned as he looked up at her. He was proud of himself for what he had been able to accomplish.
Kiki could hardly believe one of her clients had actually made her cum. That hadn't happened in such a long time she couldn't remember the last time it had happened. Once in a while she would experience an orgasm, but that was almost always with a client she knew very well and even then it was incredibly rare. She looked at his handsome face. His mouth was on her pussy and her thighs were raised and on each side of his head. She said, "Come up here Baby. Put your cock in me. I want that beautiful cock in my pussy."
James slid between her legs and up her body until his chest was pressed against her breasts. He could feel the softness of her breasts along with the satin and lace of that tiny bra she was still wearing. He liked the way it looked on her and had not wanted her to remove it. He was kissing her when he felt her right hand move between their bodies and her fingers wrap around, taking hold of his hard cock. He felt her guide his cock to her opening. He could feel her warm slick wetness on his glans and knew at least part of his cock was inside her. She pulled her hand back then looked up at him saying, "You're in place. Just push it into me. Push it all the way in, as deep into me as you can."
He began to do as she said. Slowly he began pushing his hard flesh into her. This was the first time he had ever had his cock inside a pussy. The incredible sensation on his cock of her body accepting his hard manhood was incredible.
When he was all the way inside her his pubic hair was pressed tight against her bald mons. Kiki said, "Yea, Baby, that feels good. You are such a big man. Do you like the way my pussy makes your cock feel?"
"Fuck yea. This is amazing."
Smiling she said, "I thought you might like it. Now I'm yours. You own me, at least until tomorrow. You can fuck me fast, slow, hard or gentle. Fuck me however you want."
"Oh fuck! I forgot!"
Kiki realized something was wrong and asked, "What's wrong?"
"I forgot a rubber."
She laughed and said, "Do you want one? We can stop and you can put one on if you want."
"Don't you want me to wear one? Shouldn't I?"
"Yes Honey. Normally you should, but I make everyone wear one and I get regular checkups. You have never been with a woman so you are safe. You are the only man I've not made wear a condom, but if you want one, that's okay. If you don't that's also okay."
"What do you think?"
"I personally would like it if you put your cum inside me instead of a condom, but you need to do what you want."
"Okay, it does feel really good like this. I would like to do it without one, if that's okay."
"Perfectly okay with me. Now that we have that settled, I want to feel that big hunk of man meat fuck me."
James grinned as he began to withdraw from her. Just before he pulled all the way out he pushed back into her slowly. He did this a few times then began to speed up. He was thrusting into her hard when she said, "Yea Baby, just like that. Fuck Kiki's pussy with that big hard cock."
Her words only added fuel to his level of lust. He was now fucking her even harder. She was a petite little girl and felt so small and fragile under him. He was about to cum when she said, "Stop, don't cum yet. I want to show you something."
James stopped just in time. He had jerked off so many times he knew how it felt when he was about to cum and he had been very close. He was glad she had stopped him since it gave him time to get himself under control.
Kiki had him roll off her and she got on her hands and knees. She lowered her head to the pillow then said, "Okay, get behind me and put it back in my pussy." She laughed and said, "Make sure you get it in the correct hole."
James moved behind her, gripping her hips with his hands. He looked down and saw her little pucker hole. He had seen guys put their cock in a woman's ass in the videos, but he couldn't imagine how his cock could ever fit in that tiny hole. He took hold of his wet cock and put it back in Kiki's pussy. He then began thrusting in and out of her. She cautioned him to not thrust into her as hard as he had before. She explained he was now going deeper inside her and she couldn't take him at full force like she had just been doing.
He did like the way she felt and liked being able to grip her hips. It didn't take long before he was back where he had been and he pushed into her hard holding himself deep inside her as he came. She knew he was filling her and said, "That's it Baby. Fill my pussy full of your cum."
They were laying naked next to each other when Kiki asked, "Was it as good as you thought it would be?"
"Better, if that's possible," said James.
"I'm happy you liked it. Is there anything else you want to do?" she asked.
"Well there is one thing I wanted to ask."
"Let me guess – my ass – right?"
"How'd you know?"
"All men like fucking a woman's ass."
"Really? It's not that I wanted to do it, I just wanted to ask if you have ever done that."
"Sure, many times."
"How can a cock fit into such a tiny hole?"
"Very tight. Seriously, that's why guys like it. It's so tight. Yes a cock will usually fit, but you have to go slow and use lots of lube. If you want to put it in my ass, we can try. You are very thick but I think I can do it."
"Really? I would like to try."
"I think I can take you if you go slow."
James and Kiki lay in bed talking. James could hardly believe how easy it was to talk to Kiki. Before when he had talked to a girl, he had always been extremely nervous. He learned Kiki was seven years older than him, but she was so small and was so easy to talk to it didn't seem like she was any older than the girls he had gone to school with.
Jennifer had been very excited as she watched her son drive off in his new car to meet his date. He had been out of sight just a few minutes when she began to worry about him having a good time. She even called the hotel an hour later to make sure he had checked in without any issues. When they rang his room nobody answered the phone. She felt bad about checking up on him, but she wanted to know if things had gone as she planned. She knew he had checked in and since nobody answered the phone he had likely already met up with Kiki and they were at the restaurant. She vowed to mind her own business and not check up on him any further.
She had tried to pass the time by watching a movie, but could not stop thinking about James. She thought back to when she gave him the box with the photos and how hard he had been when he hugged her. She was ashamed of herself for even thinking about her son like that. She had never thought of him in a sexual manner before. Sure she wondered if he was a virgin or how he was with the girls, but that wasn't how she'd been thinking since she decided to give him a birthday present consisting of spending a night with an escort.
The harder she tried to get her son out of her thoughts the more she found herself thinking about him. She finally turned off the television and decided to look up some information on the Internet. When she tried to log onto her computer her monitor flashed a bright light then went black. She tried everything she could think of, but she finally determined the monitor was dead. She would need to get a new one. That is when she decided to use her son's computer. He'd recently replaced his computer and had a nice one. She had looked at it when he got it, but since she had her own she had no reason to use his.
Sitting down at his computer she logged on. She opened his browser and began typing in the information she wanted to research, but the predictive suggestions the browser offered brought up sites she had not expected. Forgetting about her original topic she began looking specifically at his browser history and found sites that didn't surprise her, but it was what she found, she never would have expected, that got her full attention.
Her son was a healthy 18 year old male and she wasn't surprised he had been looking at porn. Jennifer was not so naïve as to think he never looked at porn, but the type of porn he was looking at was what she had not expected. He was not only watching videos and reading stories of a pornographic nature, he was specifically searching for porn with the central theme of mother and son incest.
She sat there trying to process this new information in her own thoughts. She happened to glance at the waste basket and saw used tissues. Reaching into the trash she picked up one of the tissues on top. That's when she realized it wasn't dried. Opening the tissue it was obvious what the content of the tissue was.
It appeared James was masturbating in his room while viewing mother-son incest materials. She wasn't upset, as she felt most mothers would be, but she was concerned that both she and her son had been fantasizing about the same thing. The question now was what she should do, if anything. Would James think differently after his night with Kiki? She was hopeful he would.
After two hours of laying in bed talking to Kiki while she fondled his cock, James found he was the proud owner of a new erection. He wondered how many times Kiki could get his cock hard in one night.
While still holding his cock Kiki asked, "Are you still interested in putting this monster in my little ass?"
"Can we at least try?"
"Sure, but you have to promise to go slow and do exactly what I say."
"Okay, I promise."
Kiki opened her purse and pulled out a condom and bottle of lube. She said, "For this you really should use a condom. I always carry lube. You need to put a lot of lube inside me and on the outside before we try this."
She could see the sparkle in his eyes at the excitement of doing what she was offering. She normally did this herself, but she had a feeling James might like to do it. As it turned out she had been right. Her tube of lube had a nozzle on the tip that easily slipped inside her. Lying on her back, on the bed, with her legs pulled up she looked at James as she said, "Okay, put the tip of the tube inside me."
She felt the cool nozzle enter her. James looked up as if asking for further instructions. "That's it Baby. Now squeeze the tube and put quite a bit of the slippery gel in me."
The cool gel always felt good as it filled her. When she thought he had put enough in her she said, "That should be enough. Now pull it out and coat me good on the outside."
James had lost his shyness as he used his fingers to smear the clear gel between her firm cheeks and around her little hole. She liked the way this felt and could have let him do this all night. She finally said, "I think that should be enough. Now hand me the lube and come up here so I can coat that big handsome cock."
She almost laughed at the look on his face. He reminded her of one of those old movies of a small child in an old General Store looking at all the jars of candy. The excitement on his face could only be described as 'cute.' She really wanted to do this, not for herself but for him. She had already been paid and wasn't sure she would be getting a tip. She always liked money, but for some reason this night and this date was different. She was accustom to men watching the clock to make sure they fully utilized their time with her. With James it was different. She would be spending the night and he likely had no idea how much his mother had paid Kiki for her to let him use her body for his enjoyment for the night.
Kiki saw his cock was as hard as it had been all night. She slowly coated his cock with the gel, making sure to also coat his ball sac. This had absolutely nothing to do with what they were about to do, but she knew how sensitive this area was for a man and wanted to give James all the enjoyment she could. She was sure this would likely be his last orgasm for the night.
When she was satisfied he was properly lubed and ready to put his cock in her ass she put the cap on the lube and placed it on the bedside table. Looking at him she said, "I can roll over on my tummy and you get on top of me or we can do it like this. Even though I prefer it like this, as large as you are it might work better if I'm on my tummy. Is that okay?"
"Sure, whatever you think will work best."
She gave him a smile then rolled over. She looked at him and said, "Get on top of me and remember to go slow. If I say stop, please stop and pull out. If I say wait, just stop pushing into me, but don't pull out. If that happens it is because I just need a moment to adjust. If I say anything other than 'stop' or 'wait' keep doing what you're doing. Does that make sense?"
"Yea, wait or stop. I got it."
James saw Kiki bunch up her pillow hugging it as she put her face in it. He was looking at the back of her head and thought her hair looked so soft and pretty. He looked down further at her ass. It was so small and firm. Her legs were together as he placed one of his knees against the outside of each of her knees. His cock was so hard it hurt. He moved down until the tip of his cock touched between her ass cheeks. Pushing between them they separated and he was now touching the outside of her little hole he had just lubricated.
He asked, "Are you ready?"
Nodding her head she said, "Just go slow."
He began pushing against her hole and at the same time lowered himself until his chest was pressed against her back. She felt so small and vulnerable underneath him. His nose was in her hair and it smelled like flowers. He thought her shampoo must be scented like the shampoo he had seen in his mother's bathroom.
James was surprised how hard he was having to push. He could feel Kiki's body tense underneath him. He was afraid she was going to decide he was to big for her and stop him. He didn't want to hurt her, but he did want to see what it felt like to be in a woman's ass. He lowered his mouth to her ear and asked, "Keep going?"
She didn't answer, but did lift her head enough to nod. He kept pushing but finally she turned her head to the side and said, "James, stop! This isn't going to work. You're cock is too thick."
Looking down he could see her face was wet with tears. He was already off her and laying next to her. He brushed the hair from her face and she said, "I'm so sorry. I thought I could do it, but you're thicker than any man who has been in my ass. I'm sorry I couldn't do this for you."
In his typical caring manner James said, "It's okay. I understand. You've been amazing, it isn't that big of a deal."
"Yes it is. I really wanted to do this for you, and thought I could do it, but I just can't."
Kiki wiped the tears from her eyes and got out of bed. She went into the bathroom and came back with a warm washcloth. She cleaned the lube from James' cock. It was still hard when she looked up at him, smiled and said, "We can't let a nice hard cock simply go to waste." She then took him in her mouth and slowly began to give him a blow job that she made last almost an hour. She was determined to make up for what she had been unable to do for him.
She would take him right to the edge then ease of letting his arousal fade slightly before taking him back almost to the point of no return. She did this over and over until James didn't think he could take any more. When she finally decided to let him cum she straddled his cock taking his thick shaft into her pussy while facing him Cowgirl style.
James had his hands on her breasts when she sat up straight and put her arms behind her back to unclasp her bra. Letting it fall down her arms she tossed it to the side giving James full access to her firm and natural C cup breasts. She rode up and down on his cock using every trick she had learned as an escort. She would sit on his cock forcing it in her as deep as she could get it then use the muscles deep in her pussy to squeeze his glans and shaft. She practiced her Kegel exercises daily. This was something all men enjoyed her doing.
When James felt her squeezing him the first time his eyes shot to hers in surprise. He asked, "How did you do that?"
Kiki grinned and said, "Lots of exercises. Do you like it?"
"Hell yea! That feels great!"
She knew it wasn't the anal penetration he had wanted, but it did seem to take his mind off what she had been unable to do earlier. Due to the edging she had done earlier, his heightened arousal did permit him to last long before he came shooting jet after jet of cum up into her.. Kiki remained on his cock until it began to soften.
Normally Kiki would only do what she did next with a boyfriend she was involved with, but James had touched a sweet spot in her and she found it was something she wanted to do. She gave him a kiss then lifted herself off his cock and leaned over to take him into her mouth. She cleaned his cock and scrotum of all their combined body juices.
Only after she was absolutely certain he was clean did she lay next to him. James had his arm around her like a boyfriend would do. She laid her head on his chest and remembered how she had told his mother what she would offer her son was a 'girlfriend experience.' She felt she had gone beyond that and even could feel a deeper connection with James than almost all her other clients. It felt good to be here with James arm around her. In no time they were both sound asleep.
Jennifer awoke early the following morning. She had not slept well and when she had been able to sleep she had dreams of James coming into her bedroom. She wasn't sure what was going to happen once James returned home. The one thing she knew for sure was that her life would be forever changed as a result of the previous 24 hours. Whether anything happened or not, she was now almost certain her son had sexual fantasies that involved her, his mother. The only question was whether or not they were simply fantasies, or were these thoughts he had a strong desire to experience in real life.
She tried to rationalize this by telling herself a lot of boys and young men fantasize about sex with their mothers. Jennifer knew she had a good body and the fact men were always very friendly and took notice of her confirmed she still had what it takes to get the attention of men. What she didn't know was how strong of an attraction did her son have for her. Not only that, she wasn't even sure this was something she could do. Sure he was a handsome man, but he was her son. She had fantasies, but she had never thought she would ever actually follow through on those fantasies, but then she hadn't known her son apparently had similar thoughts.
What she did know for sure was she now saw James in a much different light. She felt she could control her emotions as long as James didn't start showing an overt interest in her. She feared if he began to show any signs of sexual interest in her she very likely would not have the willpower that would be required to resist him.
Jennifer then wondered if she had the opportunity to change things, knowing then what she did now, if she would have still arranged the date between Kiki and her son. As she lay in bed thinking of this she almost began to stroke her clit. Catching herself she pulled her hand back and forced herself to get out of bed.
It was almost 1:30 when she heard James pull his new car into the drive. Fighting the urge to run and hug him she waited for him to come inside. She had a big smile for him when he came in the front door. When he entered she saw he had the sweetest grin on his face, confirming to her he had indeed had fun. It also confirmed, at least in her mind, that her son was now no longer a virgin.
"How did I it go? Was she nice?"
"Mom, you have no idea. She was… I don't know how to say it other than say she was absolutely awesome! Thank you so much."
"You're very welcome. I was worried you might be mad at me for setting that all up."
"Mom I love you. You know that."
"Yea, but I was afraid I might have stepped over the line."
"No, it was the best birthday gift you could have given me."
Grinning she said, "So my boy is now a man in every way."
She saw him blush then say, "Yea, I guess so."
"Tell me all about your date; at least all the parts you can tell your old mother."
He said, "First off you're not old." They sat on the couch and he began to tell her how Kiki had been waiting for him at the hotel. He told her around the restaurant then their walk on the beach and their first kiss. He then said, "I don't think you would be interested in what happened after that, but let's just say it was even better than I had ever imagined it could be."
Jennifer wanted to tell him he was wrong and she wanted to hear all the sexy details, but she knew he wouldn't tell her that part. As she listened to him she delighted in the sparkle in his eyes and his excitement from having been with such an incredible and beautiful woman.
Telling his mom about his date made James remember what had happened earlier that morning when they woke up. Kiki had been so warm and soft laying there up against him. They had gotten out of bed and showered together. She had knelt in the shower and given him another blow job, swallowing every drop of his semen when he came. They stood under the shower head as the warm water cascaded over them. They did finally turn off the water then stood there simply holding onto each other. Kiki suggested they call room service for breakfast.
When they heard the knock at the door they were each wrapped in the terrycloth robes the hotel provided for guests in the more expensive suites. James had laughed at Kiki when she put the robe on telling her they need to call down and get a petite or child's size for her. The robe supplied was a few sizes to large and simply swallowed her up.
James remembered not being able to take his eyes off her as they ate. She was absolutely the sexiest woman he had ever met. He realized it bothered him that she was an escort and not his girlfriend. As incredible as the past few hours had been she would likely be with another man if not that evening then certainly the next. If he could only have her as his girl everything would be perfect. He knew part of his infatuation with her was she was the only girl he had ever had sex with. Even knowing that he felt like she was still perfect, at least in his eyes.
For James there was only one other girl, or rather woman, who even came close to Kiki – his mother. James had always thought his mother was beautiful. Nobody else knew he had jerked off to thoughts of his mother sucking his cock and even of him fucking her. It wasn't something he was proud of, but it was a fact, in his eyes, his mother was absolutely hot. All the guys he had gone to school with commented on how hot she was. She had always been his mother and he hadn't given it much thought until he began noticing girls and thinking of them in a sexual way. The comments of his friends made him realize his mother might be mom, but she was also what they were saying. She was indeed a beautiful woman. He realized their comments gave him a sense of pride in a way he hadn't felt before. James had seen the mothers of his friends and could see on the hotness scale there was no comparison. At school functions he had begun to notice how the fathers of his friends looked at her. There was no doubt they thought she was hot, but she was still his mother.
James thought about how he and Kiki had one last fuck before they got dressed. James later discretely handed Kiki the envelope his mother had given him. He had paid for dinner from the envelope, but had not counted the money. As they were getting ready to leave the suite he had folded the envelope in half and took Kiki in his arms to kiss her again. When their lips parted he said, "You were amazing. I could not have asked for anything better. It hurts that I have to let you go." Looking at the envelope in his hand he said, "Here, this is for you. It isn't enough for what you have done for me, but it's yours.. Thank you for such an incredible birthday."
Kiki took the envelope, thanked him, then slipped it in her purse without unfolding it. She said, "Honey you're a wonderful man and whoever the woman is that gets you, she will be a very lucky woman. Enjoy life and don't get in a hurry to settle down. Believe it or not, this has been unlike any of my other dates. You are one of my most incredible men I have ever met."
James' heart was breaking as they made they way to the elevator. Once in the elevator Kiki reached over and took his hand in her own. To James the horribly slow elevator ride the previous evening had changed into what James felt was an express elevator. The doors opened at the ground floor much too soon. They walked hand in hand out the front. Kiki wanted to take a cab, but James talked her into letting him give her a ride home.
Kiki would never have let a client see where she lived, but she felt like James was different. On the drive to her apartment Kiki wondered if James had been a few years older and she hadn't been an escort, could things have worked out between them. It was something she would never know, but she did know she had enjoyed her date with him much more than she normally did with other men. She knew he would hold a special place in her heart.
Later after she was in her apartment and the door was closed and double locked she took out the envelope James had given her. Inside were fifteen one hundred dollar bills along with two twenties and three ones. She had seen James pull a hundred dollar bill from an envelope at the restaurant he had used to pay the bill. He then stuffed the change back in the envelope. For her this was a very nice tip and would help her with bills, but still she hated that the date with James had been a business arrangement. He had been too sweet for her to think of him as simply being one of her clients.
Jennifer could see as James' had been talking his mind had drifted to something else. She figured he was thinking about Kiki and it made her happy his mind was now focused on girls. She was looking forward to hearing from Kiki, but there was little doubt now regarding her son's sexual orientation.
James told his mother he wanted to show his new car to his friends. She was happy for him and told him to drive safely. Sure it was what all mothers say, and she was his mother.
He changed clothes and just before heading out the door he gave his mother a kiss. This was not out of the ordinary, but the fact he kissed her on the lips was something she could only remember him doing as a small child. It wasn't a passionate lover's kiss, but neither was it the kiss of a five year old child. Jennifer felt a tingle in her clit and wondered if she had misinterpreted what had just happened or did she still have something she should be concerned about.
She watched James back out of the drive then take off down the street faster than she would have preferred, but she was happy to see him happy. She was still thinking about that kiss when her phone rang. She answered, "Hello."
"Hello, Jen? It's Kiki. I promised I would call."
Jennifer snapped out of her daze and said, "Yea, right, Kiki. James was very happy when he got home."
"You have a very special son, but I'm not telling you anything you didn't already know. He is also a very capable lover."
"He is very shy. Was that a problem?"
"Yes, at first he was, but once we talked a bit he really did start to open up. I don't know if he told you, but we went for a very romantic walk along the beach."
"Yes, he did tell me about that. He was also laughing about you and the hotel robe."
"He got a kick out of that. I'm very petite and that robe was much too large, but we did have a lot of fun. There was one thing, I don't know if I should say anything about, but…"
"What was it? I promise to not tell him you even called."
"I felt bad I couldn't do one thing he wanted to do. I did try and really wanted to, but you probably don't know your son is a very large man, if you understand what I'm saying. Combine that with me being very petite and that was a problem."
"You mean you weren't able to take him in you?"
"Not exactly. I was able to take him in all but one place. We tried lots of lube, and even though I have done it before, I just couldn't take him. Like I said, he might be 18 and not look it, but he is very thick in certain places."
"I see," said Jennifer.
"I normally would never have mentioned it, but it was something he specifically wanted to do. I felt really bad not being able to take him there. We tried, but he was just too thick."
"I'm sure he understood."
"He did and that made me want to do it even more, but I just couldn't. I wanted you to know if he ever said anything, which I don't think he ever would. It's nothing really and I probably shouldn't have mentioned it."
"No, that's fine. I'm glad you did."
"I figure the money in the envelope was from you and I want you to know how much I appreciate it. James is a very special man. I'm not just saying this because it's you, but he's one man I will certainly remember. Thank you for allowing me to be a part of his birthday."
"Thank you Kiki for making his birthday so memorable. You be sure to take care of yourself."
"I will and you do the same. Bye Jennifer."
"Bye Kiki."
As Jennifer pressed the end button on her phone she stared at the phone thinking about what Kiki had said. It sounded like her son had a good time. She would have to remember and thank her boss for suggesting Kiki.
When James returned home it was after dark. He was excited as he told his mother what his friends thought of his car. He also told her he stopped by his grandparents house to thank them again for such a cool birthday present. They ate a late dinner then watched some TV together before heading off to bed.
Jennifer saw James in the hall. He was wearing just his boxers and even though she had seen him dressed in only his boxers many times, this time it was different. She had always intentionally avoided looking at the front of his boxers, but this time she couldn't help but glance at the thin fabric separating his manhood from her eyes. She couldn't help but to think about what Kiki had said regarding how large his male organ was. Jennifer had to force herself to not stare at him as she attempted to see for herself. Thankfully James hadn't appeared to notice her interest as he told her good night and disappeared into his bedroom closing the door behind him.
She had already taken her bath and was dressed in a short satin robe. She thought she had seen James look at her. She couuldn't figure out if he was looking at her differently, or if maybe it was just her imagination. Since that kiss on the lips earlier her imagination had been running wild. Remembering what Kiki had said on the phone, and now thinking about what James might be doing behind that closed door had her pussy wet. Thinking behind that door James might have his cock in his hand stroking it as he was watching a video portraying a son fucking his mother had Jennifer's pussy on fire.
There was a vibrator she had used over the years. The vibrator in it no longer worked, but it was still a good dildo that could reach where her fingers couldn't. She was feeling particularly randy and decided to try something. She made sure her door was closed before getting her broken vibrator out of the hiding place she kept it. She had an old tube of lube that she had had for several years. She was afraid it might be dried up or empty. She found there was enough to cover her worn out toy. Lying on her back she decided to see if it was possible for her to insert the broken vibrator into her ass. She was a petite woman, but apparently not as small as Kiki. She had to know if she could take it into her ass. She had experienced anal sex, but that had been several years earlier.
Placing a pillow under her waist and pulling her legs open and back toward her she teased her little hole with the pointed end of her toy. She pushed it in a fraction of an inch. The point penetrated her and began to stretch her little hole open. The sensation brought back memories of the last time a man had penetrated her ass. She pushed a little harder and kept pushing until it was too uncomfortable to go further.
She was breathing hard as she thought about what Kiki must have been feeling. She could not help but wonder how much larger her son was than the hard plastic toy she was now holding. After making up her mind she was going to do this she pushed it into her little hole again and again. She wasn't able to take it all, but she felt like she was slowly making progress.
After working on her ass for several minutes she placed the dildo on the bedside table and began rubbing her clit until she had a nice orgasm. She caught herself just before she cried out in ecstasy. Sated, Jennifer quickly fell off to sleep.
In his room James had shucked his boxers and had one of his favorite videos pulled up. The video was of a son attempting to seduce his mother. In the video the mother was in a tiny bikini laying next to their pool. Her son came along and seeing his mother he offered to give her a massage. The mother at first resisted, but when the son kept insisting she finally gave in. He rubbed oil into her back and didn't waste any time getting to her ass cheeks. He convinced her to let him untie the bikini bottom at her hips so he woudn't get oil on her new bikini. It didn't take long before the mother was lying on her side with her son's cock in her mouth. In the video he asked his mother if he could put his cock in her ass. At first she said no, but as the scene heated up he was working oil between her ass cheeks and soon was balls deep in her ass.
He kept stroking his cock while watching closeups of the actor's cock being forcefully driven into the ass of the actress portraying the mother. It wasn't long before the actor shoved his cock in deep and yelled to the world he was cumming. As he pulled out the camera zoomed in for a close-up showing his thick white cum leaking from the mother's ass. It was one of James' favorite videos.
As James watched the video he had his fingers wrapped around his cock and was slowly stroking it. When he had first started watching the video his thoughts had been on Kiki and how hot she had been, but the theme of the video quickly changed his thoughts to his mother. He was watching the video as he stroked his cock, but his mind was on his own real life mother, and not the actress. He was thinking how hot she had looked when he had seen her earlier outside his bedroom. She had been wearing a pink satin robe that was barely long enough to hide her pussy from his view. He remembered thinking how her legs had been so fucking hot and the neckline of the robe plunged down between her breasts. He could even see the inside curve of her breasts, but not much more. He wondered if she had any clue as to how hot her body was, or if she knew what effect she had on him.
The video was still playing, but his thoughts were elsewhere. He was thinking how sexy his mother's legs had looked then began wondering if her pussy might be bald like Kiki's. It was at that moment his cock spasmed and he filled a clean tissue with a load of his fertile semen. He tossed the tissue into the trash, unaware his mother had seen in his trash, the previous night, one of his previous eruptions in a discarded tissue. With his balls now empty he closed his browser and climbed into bed.
Laying there James' remembered when his sexual interest in his mother had begun building. It began when he stumbled onto another video where a friend of the son had told him he knew a guy who had fucked his own mother. The actor in the video decided it was time for him to try and fuck his own mother. The actress was much too young to actually be the guy's mother, but it was a porn and nobody really cared if the ages were correct. All that mattered was for the naked bodies on the video to be hot and hopefully the actress playing the mother to look at least a few years older than the actor playing the part of the son.
As unrealistic as that video had been, James remembered stooting many loads of cum watching it over and over. His time with Kiki had been fantastic, but the woman whose body he knew he wanted to get his cock into was that of the woman whose body his life had begun inside. He knew people thought it was wrong, but to him she was the perfect woman. He also knew she would never allow him to have what he wanted more that anything else. He would have to be satisfied living his life enjoying only the fantasy he conjured up in his mind of his cock inside his mother.
It had been three weeks since James birthday. Jennifer had watched to see if she detected any evidence he was now dating anyone, but saw nothing. She had thanked her boss for the referral. He wanted to know as much as possible. Jennifer told him all James had told her, but left out the call from Kiki. He confessed he had seen a few different escorts, but Kiki was his favorite.
Three or four nights a week Jennifer secretely worked on stretching her ass. She was determined to stretch her ass, but didn't really know what the purpose was. It was more of a personal goal than anything else. Her efforts to open her ass to accept a large cock had nothing to do with her son, or at least that is what she kept telling herself. She had been able to get the toy in her ass the second night, but it had been painful. Each time she tried it became easier and with less pain. She had purchased a new tube of lube and had even purchased a larger toy. This one actually looked like a cock. It was complete with a glans and thick veins along the shaft. The box it came in claimed it was an actual silicone mold made by a porn star whose name was in large bold letters on the box. She didn't know if it was true, but she did have to admit it certainly did look real.
Her broken vibrator had been hard plastic and had been smooth. It had been called a torpedo and that is what it looked like. Her new toy was much more realistic.
After having conquered her torpedo she began working on her new toy. It was much thicker, but she had managed to eventually get it fully inside her ass. It was still slightly painful, but the sensation of fullness felt great. She found a little pain even added something to the pleasure. She knew the toy wasn't physically harming her, it was simply stretching her tight little sphincter. She didn't like a lot of pain, but the hint of pain let her know she was taking as much as she could do so safely.
It was Friday and had been a busy day at the office. Both she and James had gone to bed early. Jennifer had played with her toy and then placed it on the bedside table before falling asleep. She was so tired it took a while for her to drift off to sleep, but once she did she slept soundly.
Saturday morning James was up first. His mother's door was not closed as it was normally, but was slightly ajar. He would never go in her room without knocking, but since it wasn't pulled shut he slowly pushed it open. His mother was laying on her side facing away from him. She was wearing some sort of satin top but like the robe she had been wearing, the top was short. During the night it had ridden up until it was now above her waist. With the sunlight coming in through the windows there was plenty of light to see her fully exposed ass. He knew he shouldn't be where he was, but she appeared to be asleep and the sight of her bare ass was too tempting to resist seeing. He was being careful to not make a sound when something caught his attention and he glanced at the table next to her bed to see the realistic looking thick rubber cock. It appeared to be covered with something, but fearing he would be caught he backed out of her room pulling the door almost closed, just as he had found it.
Heading back to his room his cock was painfully hard and was making a tent in his boxers. He closed his bedroom door and immediately began stroking his cock. This time he didn't have or need a porn video running. In his mind he was reliving what he had just seen. He was imagining climbing into bed with the hot female who happened to be his mother. The thought of climbing into bed with his mother had him so aroused he didn't last long before he filled a tissue and had to grab three more to soak up all the cum that shot out of his cock.
After tossing the tissues into the trash he decided on a plan. The only question was whether or not it would work.
James remained in his room with his door open so he could listen and hear his mother when she got up. He didn't have to wait long before he heard the bathroom door close. He knew her routine and about how long she would be in the bathroom.
He checked his cock to make sure no additional drops of cum had formed on the tip. He then pulled up his boxers and reached in through the fly. Taking hold of his cock he pulled it out and through the opening. He stood and looked in a full length mirror. Having just cum his cock was soft. Like all guys he had measured it before and knew it was eight inches long flaccid. It grew two additional inches when it was hard as well as getting much thicker. He liked the way it looked hanging out of the fly in his boxers. James preferred sleeping nude, but on a few occasions he would sleep in a pair of boxers. He had actually woken up a few times with his cock hanging out his fly. Each time he had wondered how that could happen, but the fact is it did.
James heard the hair dryer and knew that was his mother's last thing to do before coming back out. With his door open he was as ready as he could be. He felt his cock starting to fill with blood and harden. If that happened it would spoil his plan. He willed it to soften, but it refused. He did manage to keep it from becoming fully erect and sticking up like some flag pole. When he heard the door open he stumbled out his door like he had just woke up and was unaware of the condition of his cock. He was rubbing his eyes when he saw his mother glance at him then freeze.
In a faux sleepy voice he asked, "Mom, you up already?"
"Y-y-y-es James. You just get up?"
Yawning and rubbing his eyes while acting as if he was totally unaware of his exposed cock he said, "Yea, I slept like a log."
He was now looking at her standing there with a towel wrapped around her otherwise naked body. He acted like he just noticed she was staring at him as he followed her line of sight and was now looking at his bare cock on full display. He said, "Oh shit. Sorry about that Mom. It does that sometimes."
He then slowly took hold of it and stuffed it back in his boxers. He looked at his mother who was still staring at his boxers and said, "Sorry about that Mom. It sometimes has a mind of it's own."
"Uh huh" was all she said.
Now safely back behind her bedroom door Jennifer was leaning against the door with the image of her son's cock burned into her brain. She thought, 'Kiki was right. That thing is huge, even when soft. What must it be like when hard?'
James gave her a few moments, but knew she hadn't had enough time to dress before knocking on her door. "Mom, you okay?"
From behind the door he heard, "Yea, just give me a few minutes to get dressed."
"Mom, I need to talk to you now. Can I please come in?"
Even though she knew it was a mistake, Jennifer turned, took hold of the door knob and turned it. Pulling the door open she saw her son standing there just as he had been moments earlier. His cock was still tucked somewhat safely inside his boxers, but she could see it had become partially hard by the way it was filling and pushing his boxers forward.
"Mom, I think we should talk."
Jennifer didn't know what to do. She tried to look up into her son's eyes, but she was unable to tear them away from his boxers. She watched what had started out as an obvious bulge grow slowly until it had become a tent. She then realized her son had closed the space between them. She felt his hand on her chin as he lifted it.
Even as he brought her chin up her eyes remained locked on the front of his boxers until she could no longer see it. Her eyes then went to his and she saw it in his eyes. She heard her own voice say, "No James, we can't do this. I'm your mother." While her body was saying 'I need you. Take me and fuck me.'
She heard James reassuring voice say, "It's okay Mom. Nobody needs to know," just before she felt his lips on her own. She instinctively opened her mouth allowing his tongue to probe her mouth. This was a kiss filled with unbridled passion. She put her arms around her son's neck and felt his hand under her arm where she had tucked the towel to keep it from falling. She felt the towel drop away from her body, but at that point she didn't care. She wrapped her arms tighter around her son's neck pressing her breasts against his bare chest. She felt one of his arms slide behind her knees while the other was behind her back. She felt her feet leave the carpet as he lifted her into his arms and began to carry her toward the bed. As he carried her their lips remained locked together in a lover's kiss. After laying her back on the bed their lips finally parted.
Looking down at her James thought his mother was the most beautiful he had ever seen her. He looked at her body and said, "Mom you're beautiful. I need you so much."
"Baby, I'm yours if you want me. Take me and show me what a man you have become."
James felt her hand pull at the waistband of his boxers. He helped her lower the garment and saw the look on her face when she saw his fully erect cock. He had seen on the bedside table what she had been using and was pretty sure he was bigger than it. The look on his mother's face pretty much confirmed his own assessment.
She looked up at him smiling as she asked, "You really do think I'm pretty?"
"Are you joking? Mom your gorgeous."
Grinning she pulled him over on top of her. The feeling of her firm body and soft skin under him felt incredible. In much the same way Kiki had done, his mother inserted her hand between their bodies, taking hold of his hard manhood and rubbed it between her moist lips. Holding him in place she looked up at him saying, "Take me Baby, I'm all yours."
As James began pushing his cock into his mother he felt her release his cock then move her hand away. He didn't know how it was possible, but she felt even better than Kiki. He was began thrusting his hard cock in and out of this woman who had given him life. Thinking about the fact just over 18 years earlier he had traveled through this same tunnel that was now making his cock feel so good.
Because he had jerked off an hour or so earlier he was now able to thrust himself in and out of her bringing her to several orgasms. When he could last no longer he said, "Mom I going to cum."
"Fill me with your cum. I need to feel your cum inside me. I want your precious seed."
Everything combined and came crashing down on James as his cock began to pump spurt after spurt of thick fertile cum into his mother's body. When his cock stopped pumping his semen into his mother, James collapsed on top of her.
Jennifer wrapped her arms around him saying, "Thank you Baby. Thank you for giving me that."
They lay in bed talking about everything. Jennifer said, "If you want to sleep in here, I would like that."
"Really, you want me to sleep in your bed every night?"
"Honey, after what we just did, it is OUR bed, and yes I want my man in bed with me."
She had promised Kiki to not tell James she had called and told her about the more intimate aspects of their date so she decided to approach it a little differently by saying, "Honey you do know I have two other holes I would like for you to try. Maybe tonight we can explore both of those if you want."
James looked at her a moment then hugged her saying, "Mom I love you so much!"
Jennifer kept teasing James as he followed her all over the house. He couldn't get enough of her, and his enthuisasm was infectious. She felt like she was 18 again. She liked having a handsome young man touching her as he tried getting into her panties. After a while she didn't even think of it being her son who was trying to coax her into bed. Once she even told him she was going to call Kiki and see if she wanted him back.
He said, "Mom she was amazing, but now that I've had a woman so much better, I wouldn't want to go back to her. You're so much sexier than her."
Jennifer was flattered but wasn't so sure she was willing to believe what he was saying. She had never seen the girl in person, but had seen her photos and Jennifer knew a beautiful girl when she saw one. Kiki was no doubt beautiful.
She finally gave in and agreed to go to bed early. Jennifer knew what James wanted and was beginning to wonder if she should have promised him what she did. It was too late now and like Kiki had said, Jennifer was determined to do her best to let her man experience her body in this manner. She had been practicing and while James was a little thicker than her new toy, she was pretty sure she could do this.
James was smart enough to take his time getting his mother worked up and wanting his cock. He began by starting out with a massage. They were both naked as he rubbed the oil into her back. He teasted her but didn't touch her where he had learned Kiki wanted him to touch. He wanted to massage her ass, but intentionally went from her waist to her thighs. He rubbed between her legs and his mother tried to get him to move further up her legs. Instead he moved lower to her calves and feet. He massaged her toes admiring the pedicure she had just had done. He was not really into women's feet, but he had to admit a pair of small feet in sexy heels was sexy, even if he didn't have a foot fetish.
He began slowly moving back up her legs. As he got closer to the top of her thighs she spread them a bit to give him better access. One thing he had learned that morning was his mother did keep her pussy bare. She told him she saved three or four times a week. She had told him at first she had started shaving for bikini weather when she was much younger and learned how good it felt. Even though there were no men in her life she had chosen to keep her pussy bald.
James drizzled oil between her cheeks then massaged it in. There was something first about Kiki's and now his mother's ass that excited him. Sure her pussy was great, but her ass held a special interest. Maybe it was that he had been so close once and had failed that his mother's ass excited him so much. He was hopeful this night would turn out better.
Slipping his fingers between her cheeks his mother lifted her pelvis off the mattress to push against his fingers. He gently massaged the little hole and found his mother was as sensitive there as Kiki had been. He knew his mother had given herself a series of enemas. She had chased him out of the bathroom and he later found an enema bag she had evidently been using. He liked that she had put in the effort to prepare her body for him. It excited him knowing she was offering herself to him. The fact he was her son didn't really matter to James. He knew he wanted her and knowing she was his mother only served to excite him more. He didn't see what the big deal was with regard to incest. As long as they were both adults what difference should that make? When he told his mother this she kissed him and told him he would understand later.
He understood the deal with children and birth defects, but if they didn't have children what was the problem. Not only that he thought the idea of his sperm making a baby in his mother was very exciting. He knew she most likely wouldn't agree, but he knew he would try and talk her into letting him get her pregnant. The idea of what he was doing had fueled countless orgasms in the privacy of his own bedroom.
James gently slipped his finger into his mothers ass. She felt so warm and slippery inside. It was different than a pussy due to the tight ring keeping the hole closed. He could tell it was tight and that must be what Kiki was talking about when she said men liked the way her ass grips their shaft. His mother was not objecting to his finger in her ass. It was quite the opposite with her heavy breathing and the way she was moving her ass with his finger deep inside her.
She said, "Put more than one in me. Stretch me as much as you can. Baby that does feel good. Put lots of oil on me and in me."
James was happy to do as she wanted. He pushed a second oil covered finger into her ass and soon a third. She had him take it easy with his third telling him to not thrust them into her, but instead to use them to open her up for his cock. James had been anxious to learn about the female body, but this had been so much more fun than he had ever imagined. First Kiki and now his own sexy mother. He knew his 18th birthday had been one to remember, but he had a feeling the year or years following his 18th birthday would be even better.
His mother eventually told him she wanted him to do her front. When she rolled over he began in the most logical spot – her tits. Making it even better she put some of his oil on her hand and took hold of his cock. She made sure to not overstimulate him, but her oiled hand felt really good to James. He moved to her pussy and he separated her lips while keeping his cock close enough for his mother to be able to reach it.
Jennifer was surprised how easily her son found her clit. She thought maybe Kiki had been responsible for teaching him that. When he bent down and took her clit between his lips then began sucking on it, she knew without a doubt it had been either Kiki or one of his porn videos that had taught him this trick. She could not help but moan as he expertly sucked on her sensitive clit. She had even tried to stop him, wanting to cum with his cock inside her. Her efforts were ignored and she experienced a squirting orgasm. This was not her first, but she had not had all that many. She had to be extremely aroused before she squirted during an orgasm.
When she had recovered she said, "I'm so worked up now. I want your cock in my ass."
James grinned at her and not needing to be told twice asked her how she wanted him to do it. She wasn't sure what he meant until he told her what Kiki had said. She knew it might be easier on her tummy, but she really wanted to see her son's face to see his expression when his cock penetrated into her ass. She was pretty sure she would be able to take him either way.
Laying on her back she pulled her legs up. He had already oiled her up and she had covered his cock with oil as she had been massaging his breeding organ. They didn't say a lot to each other as James moved to place his cock against her little hole. When he had it in place Jennifer nodded and said, "Yea Baby right there. Now push against me slowly. You will have to push hard, but I know it will open and let you in.
James slowly applied pressure as he watched his mother's face. He liked this much better than when he had tried this with Kiki and he had been looking at the back of her head. He saw a grimmace on his mother's face and asked, "Want me to stop."
Shaking her head side to side in a strained voice she said, "No, keep going. Push harder, you can do it."
He began pushing harder afraid of hurting her when he felt his cock slip in and the ring of muscle clamp down hard on him just behind his glans. Jennifer said, "Hold it baby, stop right there."
Misunderstanding, James started to pull out and his mother said, "No Baby, don't pull out. Just hold it right there a minute and let me adjust."
Relieved, James did as she said. The tight constriction on his shaft really did feel good. He could see now what Kiki had been talking about. After a couple minutes his mother said, "Okay Baby, slowly push that wonderful cock all the way into me."
James watched as his mother concentrated on taking his shaft. When he felt her ass cheeks touch him he knew he was almost all the way in. Jennifer felt it too and said, "All the way Honey, give me all of your cock."
"Oh Baby, I never realized how huge your cock is. You have me stretched to the limit."
She heard the concern in his voice and saw it on his face when he asked, "Want me to pull out? Mom, we don't have to do this if it hurts."
No Baby, it's okay. I just need to get accustom to such a huge cock. Honey I've never been with a man whose cock is anywhere near as thick as yours. Honestly it does feel good, but it will take me a lot of practice to be able to do this easier. Do you think you can help me out with that?"
Grinning he said, "I think I can make time in my busy schedule, but only because it's you."
She had always loved his sense of humor and replied, "That's very thoughtful of you. You're such a gentleman."
The absurdity of her comment made it all that more funny. Here was her son with his cock buried root deep in her ass and she was complementing him for being such a gentleman. They both were laughing when Jennifer said, "Okay Baby, let's start out slow. Fuck your mother's ass big boy."
With a huge smile James began to pull out of her. When he was almost out he slowly pushed back in. Her eyes were locked on his and he loved the smile on her face. She was nodding encouragement as his abs touched her ass and he pressed driving himself into her only to then reverse direction. After several strokes like this he could feel her starting to move her hips in a small rotation. She said, "Much better. It's starting to feel really good. You can fuck me faster and harder if you want."
After a couple more slow strokes he began to slowly increase speed. This felt nothing like fucking a pussy. He now understood what Kiki had said about men enjoying fucking her ass because of the tightness gripping their cocks. His mother was getting into it and getting more energetic as she told him how much she had been thinking of him. She was saying things James had never believed she would say as she told him to fuck her ass and fill her with his cum. Her excitement was fueling his own passion and it wasn't long before he thrust hard burrying himself deep in her just before his cock began injecting his seed into her and filling her ass. It was without question the best orgasm he had ever felt. Granted most of his experience came from masturbation, but he had felt a few pretty intense orgasms that night he had spent with Kiki.
When he pulled out of his mother they hugged and kissed. He acually thanked her for letting him fuck her ass. She told him she had been looking forward to it and confessed she had even been stretching her ass with a dildo. James told her how Kiki had tried, but had been unable to take him in her ass. Jennifer never confessed the fact she already knew. She liked that he felt comfortable enough to share such an intimate story with her.
They eventually got up and took a shower together. James liked feeling his mother's soapy hands on his body. It didn't surprise him that most of her attention was given to his cock and balls. He even liked when she ran her soap covered fingers between his cheeks and over his own own little hole. He literally jumped when he felt her insert the tip of one of her fingers in him.
"Did you like that?" his mother asked.
"Yea it felt good, but I didn't know you were going to do that."
"Baby I have lots of things to teach you. Our bodies can give us so much enjoyment."
When it was his turn to wash his mother, James did it much the same way she had done him. He even pushed one of his fingers into her ass. It wasn't tight and actually was open slightly. When he asked her about it she assured him by morning it would close back like it was, but after having such a thick cock in it the process would take a while.
They remained in the shower until the hot water ran out and began to turn cold. Jennifer jokingly said they needed to get a larger hot water tank so that in the future they would be able to stay longer.
When they were back in bed they cuddled and touched each other as they talked. Jennifer saw her man had undergone quite a change. Gone was the shy son and in his place was a confident, but curious, young man who wanted to learn all he could about how to make a woman happy. She told him she had a lot to teach him and that the next lesson was to show him how good his cock would feel in her mouth.
There was something about a woman swallowing his cum that excited James. Feeling her mouth on his cock was one thing, but watching his cock slide in and out of her mouth and then for her to take his cum and eagerly swallow it was even more powerful.
That was the second night they slept in the same bed. They each loved feeling the naked body of the other up against them. Boxers and night shirts were banned from their bed as they slept naked and in each other's arms whenever possible.
The following morning James and his mother moved many of his things into what was now 'Their Bedroom.' They left behind enough in his room for friends and family visiting to not realize he no longer slept in the bedroom most thought of as his. He continued to use his computer in his old bedroom, but oftentimes his mother joined him as they both enjoyed watching porn where actors played the roles of mother and son. One time he started a video before his mother realized what it was. The video involved a dominate male and submissive female practicing bondage. Jennifer looked at her son who was already looking at her. She saw the grin on his face and realized she was going to be busy keeping her man happy.
Jennifer encouraged her son to date girls his own age. She was hopeful one day he would find a woman and get married. She wanted grandchildren. James had told her he wanted to impregnate her so they could have a child of their own. He told his mother she was not too old to have children, but as diplomatically as possible she made it clear she didn't want to have his child. She said while it was true they both fully enjoyed their current relationship, it was still considered wrong by most people. She explained she didn't care what others thought as long as the two of them were happy. She explained even though this was all true, she didn 't want to bring a child into the world having been the product of incest.
At first James was upset thinking of this as a rejection of him as his mother's lover. He later realized it wasn't what he had at first thought and that his mother really did love him as both her son and her lover.
A few years passed and James did fall in love with a girl. Her name was Sasha and she reminded James of his mother and Kiki. She was cute and fun loving. She loved sex and the best thing was she didn't mind sharing him with his mother. Every now and then James would return home to spend the night with his mother. He would even drop by on a weekend and the two of them would spend a couple hours in bed sharing their intimate desires. James and Sasha gave Jennifer the grandchildren she had wanted.
Jennifer did cave to the pressure of Ben, her boss, and started dating him. The sex was good but they had very little else in common. They realized they were not on the path to marriage and agreed to just enjoy each other and be fuck buddies. They were good together in bed, but that was the extent of their personal relationshp. The best part was they were able to maintain their professional work relationship while still enjoying an intimate relationship. It wasn't uncommon for Ben to call her into his office, have her lock the door and her to leave with a load of cum in her stomach or pussy. She never allowed any man other than the man she loved more than any other to penetrate her most intimate of holes. She told her son that her ass belonged to him and was only for his own personal use.
THE END© 2019