Note: This story was dynamically reformatted for online reading convenience. All the girls I've `loved' before. Part 10 - Janet the secretary By xesman Note from the author: This story takes place in 1995. It occurs about 20 years after my time with Sandy, Jill, and Brenda. During that time, I wasn't dormant. It's just that those stories are not that exciting. Maybe at a later time, I will compile a bunch of short stories about those years. During all that time, Ann was the one constant in my life. We still see each other a few times a year. Janet is a secretary in the company I work for. She is very pretty, about 29 years old, about 5'6", brown hair, very small tits, bubble butt, but excellent legs. Janet is very cocky and a smartass. She had put me down several times when I commented how nice she looked. She would make comments like, "In your dreams" and "Don't you wish". One thing that Janet was embarrassed about was her small chest size. I overheard her talking to other secretaries that she wished her boobs were bigger. She always wore clothes the hid her chest but showed off her fantastic legs. Her skirts were about as short as she could get away with before someone made a comment about their inappropriateness. Her ass was a bit large for her frame and tended to look she was sticking it out. The only term I could think of when I saw her ass swaying down the hall was either bubble butt or booty butt. I had had a couple of discussions with her boss on the side, and he said she gave that same smartass attitude to almost everybody. She hadn't mouthed off to him, though, and he suspected it was because he was the boss. He confided in me that he secretly had a fantasy where he dominated her and she was submissive. He thought that she truly was a submissive but used the smartass attitude as a cover to hide it. A couple of times when he had corrected her, she had hung her head down and kept saying, "Yes sir, I understand. I won't do it again." And things like that. The only problem, he said, was that if he tried it and was wrong, he would be in a ton of trouble. Wow, I walked away from his office with all sorts of thoughts going through my head. As shitty as she had treated me, she was still very pretty and had great legs and I wouldn't mind nailing her. Janet had worked for the company for about five years. She had a kid when she was 17 and had married the father and then divorced him about two years later. She let her parents take care of the kid because she still wanted to have her fun. She had been living with some guy named Will for the last three years and I had met him at a couple of parties. It wasn't long after I had had the conversation with her boss that Janet came to my office one afternoon. My secretary let her in and said I had an appointment in about a half hour. I thanked her and told Janet to have a seat. She looked like she had been crying and had a tissue in her hands that she kept dabbing her eyes with. She asked if she could close the door. I went ahead and closed it and asked my secretary to hold my calls. I went back in and sat down across the table from Janet. I asked her if everything was okay. She said, "No, Mr. Johnson, that was why I came to see you." I noticed that she called me "Mr. Johnson? Instead of Roy like she usually did. My mind started spinning as I wondered what she was here for. Had her boss harassed her or given into his fantasy and now she was complaining. I didn't know. I got up and got the box of tissues from my desk and brought it back to the table. I said, "Here, the one you're holding looks like it could use a replacement." She smiled a little at my joke but took a fresh tissue. I asked her to go ahead and tell me what was the matter. I had my notepad and pen out in case I needed to take notes. She laughed a little through her tears and said it seemed funny; it looked like she was going to dictate a letter and I was going to take shorthand. I laughed at her joke and she said I didn't need the notepad, this was personal. I said okay and set the pen down. I told her to go ahead. She said she didn't know where to start. I told her the beginning is always a good place. She laughed a little and then the tears really started flowing. I didn't know what else to do so I sat there and waited for her to finish. Sobbing she said, "I don't know what I can say and what I can't say." I asked her if it had anything to do with company secrets. She shook her head no. "Then," I told her, "You can tell me about it." She looked towards the door and then back at me and said, "I just don't know how to say it." "Well," I said, taking a chance, "you said it was personal. Would it make you feel better telling me after work? She thought about it a little and said, "I'm not being very professional, am I?" I told her she had a problem and I was willing to listen to her. If she felt more comfortable telling me in a less "official" place then I was okay with that. I said, we can meet at Pete's after work (a local bar not far from the office) and have something to eat and then she could relax and tell me. She had already taken quite a bit of time and I had another appointment in about five minutes. Of course, I didn't tell her that, since I didn't want to rush her or make her feel that she was taking too much of my time (which I thought she was!). She thought about it for a moment and then said, "Yeah, that would be better, I think." I told her, "Okay, Pete's at 5:30 and I'll spring for the food, so bring your appetite. She choked back another sob, and said okay. I gave her another tissue and let her out of the office. My secretary looked at her and then at me. I shrugged my shoulders like I didn't know (and I really didn't!). I asked her where my next appointment was. She said he wasn't here yet. I asked her if she had a moment. She got up and came into my office. Let me explain that my secretary,Mildred, was about 55 and very efficient. She was like a mom to most of the junior employees. I asked her what she knew about Janet. She said not much, just that she had an attitude and today was the first time she had seen her act like this. She asked what the problem was. I told her I didn't have a clue but I would let her know after I found out. She told me to be careful because the girl was probably trouble. I said I would. I finished my appointments and prepared to leave. I was still wondering what Janet's issue was. At about 5:20, I left the office and drove over to Pete's. I went in and got a booth towards the back so if Janet started her sobbing again, she wouldn't make that much of a scene. I ordered my normal drink and waited for Janet. She came in about 5 minutes later, looked around and then saw me and walked over to my table. She had cleaned herself up a little, and reapplied her makeup so her eyes didn't look as red. I noticed she still had a tissue in her hand though. She sat down and I asked her what she was drinking. She said she usually drank margaritas but she didn't feel like one right now. She asked for a scotch and soda. I waved over the waitress and ordered her drink for her and asked for some menus. The waitress came back with the drink and two menus. Janet took a drink and then set the drink down. "Thank you," she said, "I needed that." I looked at the menu and asked her what she felt like having. She said she wasn't very hungry. I told her that she would feel better if she ate something. She looked the menu over and asked what I was going to have. I told her that Pete made a great steak sandwich and I would probably have that with fries. She said, okay, that sounded good, she would have the same. I ordered for both of us and waited for the food. Janet acted like she wanted to start talking but couldn't figure out how. I suggested she wait until after she ate and then we could talk about it. She shook her head okay and took another long drink of her scotch. By the time the food arrived, she had finished her drink so I ordered another for both of us. The food was good and Janet devoured it like she hadn't eaten in a week! I finished mine and she had already finished hers and her drink as well. I ordered another drink for both if us and the waitress cleared our table off. When the third drink arrived, Janet had started to get her courage up and seemed to be a little surer of herself. She started to get some of that cockiness back. I almost wanted to reach across the table and strangle her but I stayed in my seat and listened. "Roy," she said, "Here's the problem." I noticed that it was Roy instead of Mr. Johnson. "My boyfriend dumped me and is moving back east. I can't afford the apartment by myself and have to move to a smaller apartment. I need to move out in two weeks, at the end of the month" In my mind, I knew that by smaller, she meant not as nice. She said if she couldn't find one, then she would have to move back to California with her parents and didn't want to do that. I told her there were a lot of good apartments around. I still couldn't see the problem. She said, "I know there are, but every one that is halfway decent and I can afford, requires a huge deposit." I said, "Well, can your parents help you?" She shook her head no and said that they were both retired and lived on a fixed income. Trying to understand her problem, I asked her how much the deposit was. She said between the apartment and utilities, it was $1000. I could finally see where she was coming from. She wanted $1000. I said, "Wow, that's a lot of money. Have you thought about a loan from the bank?" She said she did, but hadn't checked it out because she thought it would be high interest and she didn't know how she could pay back the loan and the interest. So now, I'm thinking that she wants a "gift" of $1000. I told her, "Janet, I just can't give you a $1000." Then I asked her why she had chosen me to ask. She said, "Well, I tried all my friends but they don't have that kind of money to lend. Then I looked around the company and most of the people who have money are bosses and I couldn't ask my supervisor for a loan. And besides, most of them are married and wouldn't be able to lend me the money without their wife knowing. And then", she paused, lowering her head, "I heard that one of the other girls had a problem and you helped her." That was interesting, I thought. There was only one girl that I had "helped" and that was Tara. She was supposed to keep my assistance to herself but for some reason, she had made it public. I would talk to Tara later about her indiscretion. I asked Janet who it was she had heard it from. She said it was Jenny. Of course it was! Jenny was the big mouth gossip of the company. If you wanted to know anything, just ask Jenny. I asked her what Jenny had told her. She said that she hadn't actually talked to Jenny but had overheard her telling some of the other girls about me helping Tara. Now, I didn't share this with Janet but Tara and I had dated a few times and had had sex quite a few times. Tara was about 10 years younger than me. We were too different so we stopped dating but remained friends. When she ran into some trouble with her ex, she asked me for a small loan to tide her over until she could get on her feet again. She promised me she would wear Victoria Secret's underwear twice a week to work and other nice things in place of the interest. Tara was a good kid so I said okay and lent her the money. I asked her to keep it quiet since I didn't think the relationship would go over real well in the company since I was a supervisor and she was an employee (although not my employee!). It took Tara 4 months to pay me back but that was a great 4 months! She kept her promise and wore sexy underwear at least twice a week. She would flash me a peek at her bra or flip up her skirt and show me her transparent panties whenever we were alone. And at least once a week, she would come to see me at lunch time (I always ate lunch in my office, it was my quiet time) and give me a blow job or bend over the chair and let me fuck her. It made life exciting and certainly took the dreariness out of the day! After she paid back the loan, she still occasionally flashed me. She called me her Guardian Angel, watching over her! But now Jenny knew and had shared it with others and Janet was trying to use it to her advantage. I told Janet that I was going to tell her something that needed to stay between her and me. I noticed her drink was empty and asked her if she wanted another. She said sure. I waved the waitress over and ordered another round of drinks for both of us. As soon as they arrived, I told Janet a little tale. I asked her what else Jenny had said about my helping someone (I didn't use Tara's name since Janet hadn't). Janet said that was all she heard. I told her that I had in fact loaned someone a small amount of money but that it wasn't interest free. Then I paused. Janet took another drink of her drink and asked me to continue. I stopped and told her that from this point on, we had to be on a "friend" basis, not an official basis. Janet looked confused. I told her that what I was going tell her was sensitive and since I was a supervisor, I couldn't relate it to her if we were in a work relationship. She shook her head and said she understood. In fact she said, she felt comfortable calling me Roy and that that was "friendly" not "official" wasn't it? I didn't know how she was going to react to what I was going to share with her but I figured if she reacted poorly, I could claim she heard something else and the alcohol had blurred her understanding. I noticed that her speech was becoming a little slurred and she was starting to have a little trouble putting her thoughts into complete sentences. So I went for it! I asked Janet if she was asking me for a loan. She thought about it for a moment and shook her head yes. I told her that Tara had borrowed less than Janet was asking for (I wasn't going to tell her how much but it was $400) and that Tara had agreed to be my slave until she paid off the loan. Janet hardly reacted at all. Then slowly, I could see some little bit of awareness seeping into her brain. She took another drink and then asked, "What do you mean your slave?" I told her that when Tara had asked for the loan, she had offered to be my slave and do whatever I told her to do. Janet nodded her head like she knew what I was talking about but I could tell she didn't have a clue. She asked, "You mean like cleaning your house and cooking your dinner and stuff?" I said, "No, it was more sexual than that." It was starting to click in Janet's brain. She said, "Oh, so you want to fuck me for the loan?" I told her it would be a little more involved than that. I looked around to make sure nobody was watching and then whispered to Janet, "No, you would have to do everything I told you to do and it would all involve sex!" I let that sink in a moment and then continued. "I'll make you an offer. You don't have to give me an answer tonight, but I need one before the end of the week." She shook her head okay and I continued. "Next week, I am going on a business trip. If you agree, you will take the week off on vacation time and accompany me as an escort. We will leave on Sunday, and return on Saturday. During the day, when I am in meetings, you will be free to do as you please. But in the evenings, I will require your services for everything I demand. You cannot say "no" or the agreement will end and I'll send you home and you'll get nothing. If you agree and do everything and I must stress the word everything, then on Saturday, I will give, not lend you, the $1000. All of your expenses for the week will be paid." I let that sink in a moment and then said, "Do you understand what my offer is?" She shook her head yes but that wasn't good enough for me. I asked her to tell me in her own words what the offer was. She emptied her drink and said, "You want me to be your sex slave for all of next week. If I do everything (and she stressed the word everything) you tell me, I'll get $1000." "And?" I asked. "And, what?" she asked back. I reminded her that if she said "no" anytime during the week, I would send her home and she would get nothing. She said okay. I suggested a little test to her. I told her for $20, she was to go to the ladies room and take off her bra, then come back to the table. She looked at me for a minute without saying anything. I took a twenty out of my wallet and held it in my hand. She asked, "You mean, right now?" I said, yeah, this was only a test. I wanted her to know that I would be very demanding during the week. She got up and walked to the ladies room. I ordered another round of drinks for us and they came back before she did. Finally, after about ten minutes, she came back to the table. She saw the new drink in front of her and took a big gulp of it. "Did you do like I said", I asked. She shook her head yes. "Where's the bra?' I asked. She said it was in her purse. I asked her to show it to me. She opened her purse and there on top was her bra. I pulled it out and looked at it. She looked all around to see who was watching but I had already made sure no one was around. Janet didn't have much in the boob department and her bra was lacy but otherwise looked like a training bra. I put it back in her purse and she snapped it closed. I handed her the twenty which she took and put in her purse. I said, `Very good. Now, for twenty more, unbutton your blouse and flash your tits to me." She said, "What?" I told her that this was easy stuff and if she couldn't handle this then she might consider saying no t next week. She frowned but looked around and then unbuttoned the top three buttons of her blouse and pulled it back and showed me first her right tit and then her left one. "Excellent!" I said and handed her another twenty. She snatched it out of my hand and stuffed it in her purse. "And very nice boobs!" I said. I told her to think about it and let me know before the end of the week because if she didn't go, I was going to make other arrangements. I wanted to plant the seed in her mind that it didn't matter to me if she went or not. I told her I would drive her home or call her a cab because I thought she had had too much too drink. She slurred that she was fine but I wouldn't take no for an answer. She asked how she would get back to her car in the morning or was I planning on spending the night at her place? I told her that was next week. I would drive her home, and then come and get her in the morning and bring her back to her car. No charge. She agreed. I paid the tab and we left the bar. I asked Janet if there was anything she needed out of her car. She said no, so we walked to my car and I opened the door for her. She got in and I went around to the driver's side. I got in and looked at her and her face had an expression on it that was between drunk and confused, or maybe a little of both. I started the car and asked her where her house was. She gave me the address which was only about ten minutes away and I started driving in that direction. About halfway there, she turned to me and asked, "Are you serious about next week?" I said I was and the offer was good. She asked what she would have to do. I told her that she would have to do everything I told her and, yes, all of it would involve sex of one sort or another. She looked like she shivered at that and asked, "Like what?" I told her that that would be my secret until next week. She always had the choice of saying no at any time but then the deal would be off and she would be on her way home. I wouldn't force her to do anything. I would give her a safe word that she could use to stop what we were doing. She said she would think about it. I told her I would pick her up at 8:15 in the morning to take her back to her car. She said okay, got out of the car and stumbled to her apartment. The next morning, I was at her apartment promptly at 8:10. I waited until 8:20 and when she didn't appear, I walked up to her door and knocked. She came to the door, fully dressed but acted shocked to see me there. She asked, "Roy, what are you doing here?" I told her I was here to take her to her car. "Don't you remember that I drove you home last night?" She looked all confused and said, "Wow, I guess I did have too much to drink! My head was hurting when I woke up this morning. I don't remember how I got home or anything." I reminded her that we had gone to Pete's and had something to eat and then we talked. Slowly, I could see her mind remembering what went on. Then I told her to open her purse. She did and saw her bra from last night in there. She got red faced and said, "I thought that was a dream or something. Did I really do that?" I shook my head yes. She told me she would be right back and then turned and walked back into her apartment. She came back a few moments later and said, "Okay, let's go." I walked her out to the car and opened the door for her. I drive her back to her car and during the drive, she didn't say a word. When we got to her car, she thanked me for the ride and got into her car. I drove to work. Once at work, I checked my mail and saw that not much had occurred overnight. Usually I had a few "panic" things to deal with that our main office came up with. They were on the East Coast so they had a two hour head start on us. But today was quiet. I thought about last night at the bar and the sight of Janet's tits! I also thought about what she had said about Jenny knowing about my helping Tara. I called Tara and asked if she had time to come to my office today. She said sure, she could come up at 10:00 if that was okay with me. I said sure and added it to my calendar. My secretary, Mildred, came in right then and said, "Good morning." I returned her greeting and told her she looked nice today, she thanked me for the compliment. Mildred always dressed very professionally and could have been any senior executive's secretary. She liked working in my department and hadn't moved in years. We went over my appointments for today and she reminded me of the briefing I had to give this afternoon. I had completely forgotten about that! I had planned on working on it last night before I got distracted by Janet. So now I had to do it this morning. So much for a quiet day! I got the briefing finished just before 10:00. Tara was early for her appointment and she and Mildred talked for a few minutes before she came into my office. Mildred said that if it was okay with me, she would go make the copies of my briefing while I was talking with Tara. I said that would work fine. She left and closed the door behind her. Tara came over to my desk and asked, "What's up?" I looked at her and she was looking exceptionally good today! Before I went into the reason for asking her up, I told her she looked fantastic today. She did a little twirl and said, "Why, thank you! I felt sexy when I woke up this morning so I figured I would dress sexy." I told her it worked! Then I got into my reason for asking her to come up to my office. I told her that Jenny apparently knew about my loan to her. She looked dumbfounded. She said, "Honestly, Roy, I didn't say a word about it to anyone. Although there was one night when a bunch of the girls had gone to Pete's after work and Jenny had sat next to her and made a comment that I was finally out of the funk that I had been in. I told her that I finally paid off the money I owed when I spilt from my ex and now I could breather a little easier." Tara said that Jenny had asked her who her "Sugar Daddy" was. Tara said she looked at her and asked what that meant. Jenny said that everyone knew she had someone helping her. Tara said she told Jenny that no such thing and then she changed the subject and said she was over her ex and let's have some fun! I guess Jenny didn't drop it and must have put 2 and 2 together in her head and figured who Tara's "helper" was. Now it looked like Tara was upset. She said, "Roy, I'm sorry. I hope it won't cause you any trouble." I told her not to worry about it. She asked if I was sure. I told her it wasn't a problem. She said she needed to get back to work. I thanked her for coming up and thanked her for looking so good. It made my day. Mildred came back from the copy room and said my briefing was ready to go. I thanked her and asked her if she wanted to have lunch with me. I thought it would be a good change and I would be able to relax a little before the afternoon brief. She accepted and we went down to the cafeteria for lunch. Since the office is usually pretty busy, I don't get to talk to Mildred very often. I asked her how she was doing and how her husband was. She seemed overjoyed to be able to talk and told me all about her grandkids and that her husband had just gotten a promotion at his job and they were really doing well. Her face seemed to brighten as she talked. As we finished, we made our way back to the office. As soon as we got there, Mildred thanked me for taking her to lunch and said it really made her day that I asked about her family. I thanked her for going with me and helping me relax for the big briefing. I did my briefing and it was warmly received by the director. I saw him making a bunch of notes on his copy and after it was over, asked me to schedule an appointment with him tomorrow to go over the options. I said I would and left the briefing room. I got back to my office and asked Mildred to call the director's secretary and make an appointment for tomorrow. She did and I was scheduled for 2:00 PM. The rest of the day went well but I didn't hear from Janet. I kind of figured she was going to wait until the last minute to pull a little power play. Although I really did want to fuck her, I was doing this mainly to humiliate her and put her in her place. It would be a lot of fun to see how far I could push it before she gave up! Friday morning I got up and dressed for work. I went into the office early and saw that there were no "disasters" looming from the main office. When Mildred came in, she again thanked me for lunch yesterday and said she had found something out about Janet, like I asked her to do. She told me that Janet's boyfriend had dumped her, although her story was that she had dumped him. She was desperately trying to find someone as a roommate because she couldn't afford the rent on her apartment. That's about all she was able to find out but she would keep her ears open. I didn't know about the roommate thing. Maybe that's why she was waiting until the last minute. Mildred reminded me about my 2:00 appointment with the director and also about my trip next week. She told me all my reservations were in place, and all the details were in a folder on my desk. "Well, not all the details," I thought! There was still the issue of whether or not Janet was going to accept my offer. I thanked her and went to work. I figured the boss would want a few more details than I had given in the briefing but I felt confident that I knew the subject pretty well and could answer any question he could toss at me. About noon, Mildred asked me if it was okay if she went to lunch with Tara. I said sure. She asked me if I wanted her to bring me anything back. I told her a hamburger and fries would be good. No hurry, whenever she was through. She had no sooner left than Janet came into the office and knocked on my door. I looked up and saw her. I said hello and asked her how she was doing. She said fine and then asked if she could come in. I said okay. She looked around and I figured she was looking to see where Mildred was. I told her that Mildred had gone to lunch with Tara and would be back at 12:45. She asked if it was okay if she closed the door. I said it was okay if she really felt it was necessary but it would probably look better if she left it open. She shook her head, and said, "Yeah, you're probably right." She sat down and put her hands in her lap, looking very meek. She looked at me and asked if the offer was still good. I told her it was and asked me if she had made a decision. She said she had and she would accept my offer. She said it was Sunday through Saturday, right. I told her that was correct. She then said she had already put the vacation slip in and it had been approved. I told her I would be at her apartment at 9:00 AM on Sunday. She asked what she should pack. I told her not to pack anything but to have out her sexiest clothing. I would choose what she would wear all week and then she could pack. I saw her clench her hands and some of the color left her face. She said okay. Then I figured I would mess with her a little. I told her to show me her breasts. She immediately looked around at the door and I said, "Everyone is at lunch. Go ahead." She said she thought I would ask that and quickly unbuttoned her blouse. She pulled it open and I could see that she didn't have a bra on. "I took it off before I came in," she said. I looked at her tits a little more than I had in the bar. I could see her hands were shaking a little and she kept looking back at the door. I said, "Okay, that's enough for now. Go ahead and button your blouse. She did and sat back down. I asked her if she was wearing any panties under her skirt. She said she had panties and pantyhose on. I said, "Hmmm." Just that comment made her turn white again. I would have asked her to pull them down but I was afraid that someone would come in and I would be in trouble! Enough time for that next week. I told her she could go and I would see her at 9 AM on Sunday. She turned to walk away and then stopped and asked, "I don't need to bring any money, do I?" I said, no, that I had agreed to pay for everything all week including all her meals. She said okay. Mildred and Tara came back from lunch. Mildred brought my hamburger in to me. Tara just stuck her head in and said hi. I waved at her and asked if she had any plans for the weekend. She said she was just going to sit around and catch up on some of her reading. She asked about me. I told her I was going to have my car serviced on Saturday since I was driving to San Diego next week. She called me a lucky dog and then swung around and left. I quickly ate my hamburger and double checked that I hadn't gotten anything on me. Sunday I got to Janet's house at a little after 9 on Sunday morning. She answered the door dressed in a summer dress that came to above her knees and flat sandals. She said hi and welcomed me into her apartment. She seemed to have some of her cockiness back. I would fix that. My idea was to humiliate her all week and knock some of that cockiness out of her head! I closed the door and said, "Okay, let's see what you've got." She whipped around and said, "What do you mean?" I told her I wanted to see what she had picked out to wear. I knew what she was thinking. I had said what I did to throw her off. She said, "Oh, okay, come on back and I'll show you." We walked back to the bedroom and she had several outfits on the bed. I knew that she had some sexy clothing since she had worn some to work which raised some eyebrows. She showed me about ten different outfits. I picked out five of them and said these would be okay. I told her the other five would be okay for her to wear during the day when I was in my meetings. I asked her what she had for shoes. She slid open her closet. She had about forty pairs of shoes in there! I found a couple of pair of sexy strappy sandals with high heels. She also had a couple of pair of regular high heels with what looked like 4 inch heels. I told her to take those four pair and whatever she wanted to wear during the day. I asked what she had in the way of hose. She opened her drawer and it was full of pantyhose. I pulled out four pair and told her pack those. I said okay, that looks good. She said she hadn't packed any underwear yet. I told her that she wouldn't be wearing any underwear all week but to show me what she had. She opened her lingerie drawer and she did have some sexy bras and panties laid out. I looked at them and said they looked nice but, no, she didn't need to bring any of that. I told her to go ahead and pack what I had picked out and we would get ready to go. She just looked at me and said, "I can't wear any underwear all week?" I said that was what I said, did she have a problem with it. She just shook her head and said okay. I told her I would hang the five nice outfits in the car so they didn't wrinkle and she could pack the rest. I asked her what she had for a purse. She showed me her collection. I picked out a small one that would hold her driver's license and lipstick and told her to take that one. She asked what about all her stuff. I told her that she didn't need any of it, just her driver's license, a lipstick and her house key. All the other "stuff" could go in her suitcase if she needed it. She said okay and started packing. As soon as she finished, I asked her if she had brought all her makeup and hair stuff. She said that was in the one suitcase. I said okay, now it looks like you are wearing a bra under that dress. I said no underwear. She shrugged her shoulders and turned towards the bathroom. I told her to stop and take it off right here, I wanted to watch. She started thinking that this was going to be a little tougher than she thought. She unbuttoned her dress and took it off. She had on a sexy bra and matching thong panties. She reached behind her and undid the bra and took it off. Then she stood there. I looked at the panties and just stared. She reached down and pulled them down, exposing her bush, which was actually pretty close to her hair color. She didn't have a lot of pussy hair and I could see her pussy lips through it. I told her to turn around and so I could see her ass. She did and then faced me again. She asked if she could get dressed. I told her I didn't like the flat sandals. I wanted her to put the pair of high heel sandals on instead. She quickly changed her shoes which made her legs look really good. The she reached for her dress. I told her not yet, that I needed her to get down on her knees and suck me off. She looked at me incredulously. She actually said, "I thought that wasn't going to start until we got to San Diego." I told her I didn't know what gave her that idea but it was Sunday and she was my slave, so do it. She dropped to her knees and started to unzip my trousers. She reached into my underwear and pulled out my cock. She looked it over and then started licking it. Finally she put it in her mouth and started sucking it. She wasn't doing a bad job, certainly better than Donna had done but not as well as Ann or Carrie, but then I had taught them how. It took her about five minutes to get me ready to shoot my load. I gently grabbed her head, careful not to mess up her hair. Then I hit my peak and shot my load into her mouth. She tried to pull away and I heard her making all kinds of sounds around my cock but I just held her head in place while I finished. I could feel her stop moving and I told her to swallow it. She shook her head no and again I told her to swallow it. She finally did and I pulled my cock out of her mouth. I gently brought her to her feet and said, "I didn't want you messing up your hair or makeup. Get used to swallowing." She asked if she could put her dress on and I said sure, we need to going. She went to the bathroom and I could hear her brushing her teeth and spitting it out in the sink. She came back with the dress on and she looked good. She made that comment that I had surprised her by asking for sex so soon. I again told her to get used to it. I figured now was a good time to tell her about her safe word. I asked her if she knew what a safe word was. She shook her head no. I told her that I would give her a safe word to use anytime she wanted to stop and call it quits. She asked why she couldn't just say stop. I told her that 1.) She might say the word `stop' without thinking as an automatic reaction to something she didn't want to do and; 2.) Having to use the safe word would make her think before she said it. I asked her what her sister's name was. She asked me what her sister had to do with anything. I told her that that was a word that wouldn't come up during the week and would be a good safe word to use. She told me her sister's name was Samantha, Sam for short. I told her that her safe word would be "Samantha says no" I asked her if she could remember it. She said she could. I told her that if she said those words when I told her to do something, the deal was off and she would go home. She said she understood. Now Janet is really starting to realize it was not going to be as easy as she thought. By now it was almost 11:00. I asked her if she had her purse and she showed it to me. I asked her to open it and show me what was in it. She did and there was her driver's license and her lipstick, just like I told her. I asked her where her key was and she said it was on the counter. I told her she needed to take it off the key ring and put it in her purse. She struggled with it and I helped her take it off. She threw the other keys back on the counter. I grabbed both of her suitcases and we walked out to the car. I put the suitcases in the trunk with my two and opened her door for her. I watched her get in and I was able to catch a glance at her pussy as she spread her legs to get in. I stared for a moment and she realized what I was looking at and turned red again. I closed her door and got in. I told her to fasten her seat belt and then we left for San Diego. About an hour down the road, I was starting to get hungry. I asked Janet if she was hungry. She said she was and so I suggested we stop for lunch. We pulled in to a restaurant and went in. We got a table and looked at the menu. I decided on the soup and sandwich and she ordered and turkey sandwich. After we ate, I went to the men's room and Janet went to the ladies room. I came out and paid the bill and then waited for her. It took her almost 10 minutes before she came out. I was almost going to have the waitress go in and check on her. When she came out she had a flushed look to her face and she had reapplied her lipstick. I asked her if she was okay and she actually smiled and said she was fine. We got back in the car and got back on the road. We chatted about a bunch of different things as I drove. I asked her what she thought of work. She looked at me and asked if I was asking as a boss or a friend. I was amazed she used the word friend but I told her as a friend. She said the job was okay. Her boss was okay but nothing special. She said a lot of the girls were waiting for Mildred to retire. I asked her why. She said that everyone liked Mildred but they all wanted her job. Again I asked why. She replied, "Everyone thinks that you're the best boss to work for!" That made my head grow a bunch! I said, "Really?" She said, "Yeah, they think that working in your department is cool. Even Jenny says that and I get the idea that she doesn't like you for some reason. Did you ever do anything to her?" I told her no, in fact, I hardly knew Jenny and until Janet had mentioned her name the other day, I hadn't really thought of her. Janet was starting to relax so I figured I'd bring it up a notch. I said, "Janet, lift up your skirt and show me your pussy." She swung her head quickly towards me and said, "What?" I told her again to lift up her skirt and show me her pussy. She dropped her hand in her lap, took a deep breath, and raised her skirt a little. I told her to pull it up higher. She raised it until it was to her waist. Traffic on the freeway was light so there was nobody around. I had the cruise control set at five over the speed limit which I knew was safe. I reached over and stroked her pussy with my right hand. Janet gasped as I wiggled my finger in her furrow and felt her clit. Her pussy felt moist, very moist. I touched her clit and then she gasped again. "Janet," I said, "Your pussy is wet! Are you horny?" She looked straight ahead and shook her head up and down. I thought back to the restaurant and how she had taken so much time in the ladies room. I asked her if she had played with herself in the ladies room at the restaurant. She again shook her head up and down. I stroked her clit some more and she started moaning. Then I stopped and told her to take my cock out of my pants. She reached over and undid my zipper. It took both of her hands to get it down and then pull my cock out. She held it loosely in my hand. "Do you want me to jack you off?" she asked. I told her no, I wanted another blowjob and make sure she swallowed everything so my pants didn't get stained. She looked at me and then dropped her head into my lap and started sucking. She was in a weird position because she hadn't undone her seatbelt. She bobbed her head up and down on my cock and every once in a while paused and I felt her trying to bring all her saliva back into her mouth. She kept it up for about five or six minutes. While she was doing that, I let my hand wander over her body and down to her ass. I pulled her dress out from under her and grabbed her ass with my hand. It felt good. I reached a little further and felt her pussy. It was pretty wet! I stroked her pussy, making sure I kept my eyes on the road. She was still doing a pretty good job on my cock. I had come once in the morning so this time it took a little longer. She kept working on me and I kept fingering her, although I was purposely avoiding her clit. She squirmed around trying to make contact between her clit and my finger. Once she even reached down with her hand and tried to place my finger on her clit. But I kept doing what I was doing. She kept bobbing her head and soon I was ready to shoot. Without warning her, I shot my load into her mouth. She kept sucking and swallowed every bit of it. She finally pulled her lips off my cock and sat back up. I removed my finger from her pussy and brought it up to my nose. It smelled sweet, not pungent at all. I looked over at her and saw that her dress was still up around her waist. I handed her a tissue and she took it and thanked me. She looked in the makeup mirror on the sun visor and checked her makeup. She dabbed her mouth a little and then reached for her purse and got her lipstick out and reapplied it. Then she looked down and saw that she was still exposed. She tugged her dress down until her pussy was covered. "Shucks!" I said, "I was kind of enjoying the view!" "I'll bet you were," she replied. We got to the hotel and, as always, Mildred came through again. She got me a fantastic hotel with a great view of the harbor. The room was fairly large with a king size bed in the middle, a desk by the window, a small sofa and of course the TV set. The bathroom had marble on the floor and walls. Overall, very nice. I brought our four suitcases up to the room and then went back down and got Janet's clothes that had been hanging in the car. I suggested she take her stuff out of the suitcase and place it in the drawers of the dresser to make it easier on her. While she did that, I went to the bathroom. I came out and sat down on the sofa and watched her finish. She walked back and forth between the suitcase which was on the bed and the dresser. As she turned, her skirt would flip up and I caught a sight of her ass cheeks and pussy more than once. When she finished, I put the suitcases in the corner. I asked her if she needed to use the bathroom. She said it wasn't a bad idea. I told her not to take too long this time and she got all red faced. She went quickly and then came out. I told her to take off her dress. She started to kick off her shoes, when I told her to leave them on, just the dress comes off. She gave me another one of those "Whatever" looks and unbuttoned her dress. After she took it off, she walked over to me and stood there. I didn't say anything for a few moments and finally she asked me if I wanted her to suck me off again. I said, "As nice as that sounds, not right now." I had been contemplating what I wanted to do next to her but when she appeared to be submissive, I figured I would throw her for a loop. I told her to get on the bed. She did and sat there. I told her to lay down which she did. I climber between her legs and sucked her tit. She didn't have much tit but she had nice nipples. Then I dipped my head and went lower until I reached her pussy. Using my tongue, I licked her slit and then found her clit. "Oh," she moaned. I kept it up and spread her legs wider and prepared to feast on her pussy. Soon I had her really moaning. She even grabbed my head and moved it around so I got just the right spot. It didn't take long for her to really start moaning and crying out, "Oh, yes, that feels so good! Yes, Yes, Yes!" I kept licking her pussy paying particular attention to her clit. It wasn't long before she grunted and then collapsed. Her clit went soft and I took a few more licks which caused her to jump a little because she was sensitive there. I finished and moved up and laid down on the bed next to her still wearing my clothes. After a few moments, she came down from her orgasm high and turned towards me. She asked, `Why did you do that? It was so nice!" I told her that this week she will always be a slave, sometimes be a slut, but will be treated well if she behaves and so far she has. She shook her head in understanding and I thought I saw a little tear form. She wiped it away and turn and stared at the ceiling. I asked her if she wanted to take a nap. She said she wasn't tired. I told her, "Good! Put your dress on and let's go." She asked, "Where are we going?" I told her she would see when we got there. After she freshened up and put her dress on, we went down to the car. I drove to a nearby mall and we got out. I told her that she didn't have enough sexy stuff to wear so we needed to get a few things. We went into the mall and I checked the directory. I found what I was looking for and started off walking with her alongside, her heels clicking on the mall's tile floor. We past by a Victoria's Secret and she turned her head and looked inside. She said, "There is some nice stuff in there." But I kept walking. A little further down, there was a Fredrick's of Hollywood. This was what I was looking for. I had already treated her to an orgasm, now I would put her down again. We walked in the store and the sales clerk came from behind the counter, introduced herself as Rita, and asked if she could help us. I told her that to start, the lady (Janet) needed four pairs of stockings. Rita asked what type, pantyhose, thigh top or garter. I told her that three pair of thigh top, two in nude and the other white. And the fourth pair would be a garter type, in white. She said fine and proceeded to open drawers and pull out what I had asked for. Janet was dumbfounded. She just looked with her mouth open, not knowing what was going on. After Rita got everything out, she asked if there was anything else. I said that she would need a garter belt in white lace. She looked at Janet to assess her size and went over to another drawer and pulled out two different ones. I picked the lacier one and said that looked good. Rita put it on the counter and asked if that would be it. I said no, that Janet needed some underwear to go with the stockings. I know I was really confusing Janet because I had told her no underwear all weekend. Rita took it all in stride and asked what type. I said that Janet didn't have much in the boob department so she needed a bra that would enhance what she did have Janet turned as red as a beet! Even Rita blushed a little. She asked Janet what size she was and Janet said 34. We walked over to where the bras were and Rita showed us what she had available. The first one she pulled out is exactly what I was looking for. It was a white, half cup bra that would Janet's nipples exposed but had some side pads that would push her tits to the center. I said that was what I was looking for and asked if Janet could try it on. Rita showed her to the dressing room and I followed. Janet went in and before closing the door, gave me a pleading look. I told her that after she put it on, to let me see what it looked like. I thought she would freak. Rita made herself scarce and went to the front of the store. Janet closed the door and a couple of minutes later, reopened it. She had her dress down to her waist and the bra on. It fit perfectly. She asked how it looked and I told her it was perfect. It pushed her little tits up and in and actually gave her some cleavage. I told her to take it off and let me have it. She unsnapped it right in front of me and then pulled her dress up. I waited for Janet to button her dress up and then took the bra up front. Rita was waiting for us. She asked how it fit. I told her it was perfect. I told her the last thing we needed was a couple of pair of panties, lacy white thongs. She went and got two pair and held then up. They were pretty sheer. I told her we needed one more pair that wasn't as sheer. She said okay and went and got them. When she came back, I told her we had everything we needed and she began to ring it up. I paid the bill with my credit card and handed Janet the bag to carry. When we got back to the car, Janet asked me about the underwear. She said, "You said I wouldn't be wearing any underwear this week, but you went out and bought underwear for me. I don't understand." I told her that the bra didn't cover her tits, just enhanced them. The stockings didn't hide her crotch like pantyhose did but it enhanced her already fantastic legs. And the panties were in case we did something that needed to have her crotch covered. We went back to the hotel and I told Janet to shower and get ready to go to dinner. She stripped and got her toiletries and makeup bags and took them in the bathroom. She spent about a half hour in there and came out. She had a towel wrapped around her head and another around her body. She had shaved her legs and all her make-up was off. She still looked extremely pretty. I told her to lose the towel on her body. She said she wasn't dry yet but the bathroom was too hot and steamy to finish in there. She wiped herself dry with the towel and then hung it up to dry. She took the towel off her head and started brushing out her hair. She said she had to blow dry it which she did. I sat back on the bed and watched her. She was getting comfortable being nude in front of me since she didn't try to hide her body as she dried her hair. After she dried and teased her hair full again, she looked around and then asked what she should wear. I told her that she should wear the purple one with the white stockings. "No underwear, right?" she asked. I told her that maybe she should wear the bra we bought. She opened the bag and took out the bra and put it on. Just like in the store, it pushed her small tits together and displayed them on an open shelf. Her nipples stood out. Her tits almost looked like B cup size with the bra on. I told her to wear it. She got the white stockings out and I told her to wear the thigh top ones. She pulled them on and said it felt weird, since she had never worn anything but pantyhose before. She reached for the panties and I shook my head no. I told her she wouldn't need them. She said the dress is awfully short. I said I knew but that was okay. She put on the other pair of the strappy heels and said she was ready. I said okay and told her to have a seat. She did and I went in to take a shower. I guess I could have done that while she was drying her hair but I wanted to watch her. It took me only a couple of minutes to shower and I dried off and went out and got dressed. Janet was sitting in the chair very primly with her knees tightly together, her skirt about halfway up her thighs and her hands in her lap. I could just see the marks her nipples were making on the front of her dress. I dressed quickly, combed my hair and told her, "Let's go!" She stood up quickly and I caught a glance at her pussy as she got up. I looked her over and said she looked like a million bucks! She said thanks. I reached in my bag and took out my digital camera. I told her to stand there while I took a couple of pictures of her. She did and even smiled for the pictures! We went out to a local Italian restaurant and had a nice meal. Janet had three glasses of wine with her dinner. We left the restaurant and went to a bar downtown. They had a live band, which was surprising for a Sunday night, and I found us a table. Janet sat with her legs crossed at the knee showing a lot of thigh and her stocking tops. She had never worn thigh tops before and I don't think she realized how much she was showing. I could still see her nipples pushing at her dress. Several guys in the bar took long looks at her legs. During one of the songs, I asked Janet to dance. We got up and started dancing. It was a fast song but she didn't dance that fast, afraid her dress would lift too much! After the song finished, she started back to the table when a slow song started. I grabbed her hand and pulled her back onto the dance floor. I pulled her tight to me and danced to the music. With her being 5'6" and wearing five inch heels, she wasn't that much shorter than my 6'3". While dancing I rested one of my hands on her back, just above her ass. About halfway through the dance I kissed her ear and then whispered in her ear, "When we get back to the hotel, I'm going to pull your dress off and fuck you hard!" She shivered a little and said, "Okay." Nothing else, just okay. The song finished and we went back to our table. A guy came up to our table and asked her to dance. She looked at me and I shrugged my shoulder. She said okay and the guy took her out to the dance floor. It was another slow song and as they danced, I noticed the guy had his hand on her ass. You could see they were talking to each other. A couple of times, she looked over at me and saw I was watching them. I saw her shake her head no a couple of times and then looked at the guy with her eyes really wide, as if in disbelief. As soon as the song finished, the guy brought her back to the table with his hand on her ass the whole way. He asked if he could buy us a drink and I declined. The guy said, "See you later!" and then left. I asked Janet what they were talking about. She said he said she had great legs and he would love to fuck her. She said he asked her to go out in the parking lot with him after the song. She said she had said no and also shook her head no. He kept trying different lines while rubbing her ass. She kept telling him that I was her husband and we were just here for a couple of drinks and dances. That seemed to finally get through to him although he told her he would really like her to suck his cock. Then she asked me if that was a setup. I asked her what she meant. She asked if I knew that guy and had told him to proposition her. I said no, that she really looked hot and he was trying to make it with her. Her nipples were really standing out against her dress. I figured it was time to go back to the hotel. I told her to finish her drink and let's go. We started to leave and the guy came up to us and handed her his card and said, "In case you change your mind." Janet put on her cocky attitude and told him, "In your dreams!" I remembered hearing that quite a few times. We left the bar and walked to the car. I opened her door for her and let her get in, catching a great view of her pussy as she sat down. I closed her door and got in and started the car. As I left the parking lot, I flipped up Janet's dress, exposing her pussy, and stroked her thigh above her stocking tops. She looked down and saw her pussy was exposed. I reached a little higher and touched her pussy. She moaned a little. She said, "Can we wait until we get back to the hotel?" I said we would wait to get back but I was just playing. She moaned and looked straight forward. I played with her pussy for a while and every once in a while she would shiver a little and moan. I drove us back to the hotel and helped her out of the car. She pulled her dress down and got out. We went up in the elevator and I started unbuttoning the top of her dress and rubbed her tits all the way up. I had the dress unbuttoned almost to her waist, her tits exposed on the shelf of her bra. The door opened on our floor and she started to walk out. There was nobody out in the hallway so I left my hand on her tit. She was walking pretty quickly trying to make it to the room as quickly as possible before someone saw us. I unlocked the door and let her in. We went inside and she started to take her shoes off. I told her to leave them on. I locked the door and went over to her. I finished unbuttoning her dress and looked at her standing there in the open bra, stocking and heels. I grabbed my camera and told her to pose for a couple of more pictures. She was shocked and said no way! I said, "Janet!" She looked at me and said nothing. I asked her if she was trying to remember her safe word. She shook her head no and asked what I was going to do with the pictures. I told her I was going to keep them as a remembrance of the week. She shivered a little and shrugged her shoulders and just stood there. I posed her and took a few pictures. I had her put her heeled foot up on the bed and act like she was adjusting her stocking. Finally I told her to turn around and took a couple of her ass. I put the camera down and took her hand and laid her back on the bed. I licked her pussy a few times and she started moaning and getting hotter. I stood up and took off all my clothes and then went back down on her. As she started getting really hot I rose up and plunged my super hard cock into her pussy. She grunted a little as I took her in a single plunge but she was very wet. Then I started sawing in and out banging my crotch on hers with a slap each time. I could feel her start to take my cock and move around under me. I had already come several times today so I could go awhile. I pounded her for a while and she seemed like she was getting close to cumming but couldn't quite get there. I kept pounding her and leaned down and licked her ear and then asked her if she was close. She was biting her lip and shook her head yes and then I asked her if she wanted me to take her out into the parking lot like this. She shook her head no and then started moaning and grunting. She came as I kept pounding her. After she came, she became a little too relaxed and almost lethargic. I pounded her and then stopped and then rolled us over so that she was on top. I told her to fuck me hard. She started pumping her pussy up and down on my cock. I raised my hips and after a couple of minutes, I shot my load into her wet pussy! After cooling down a little, I rolled her off of me and then bent down and took her shoes and then her stockings off. Then I reached behind her back ad took her bra off. I kissed her lips and then lay down beside her. Soon we both drifted off to sleep. Monday Monday I woke up at 6:00 AM. I went to the bathroom and then came back to bed. I gently roused Janet from her sleep. It took her a few seconds to realize where she was. I asked her if she need to go to the bathroom. She said no. I said, good, because I was going to get ready for the meeting but first I needed a blowjob. She mumbled something like, "Too early, let me sleep!" I said she could go back to sleep when we were done. I pulled the covers aside and lay down on the bed. Janet moved her head down to my crotch and started licking my cock half-heartedly. I could tell she wasn't fully awake yet. I guided her head into a rhythm and soon she was sucking me fully. I hunched my hips, forcing her to take me a little deeper than she liked and she gagged a bit. I think she realized if she didn't do it I was going to do it to her, so her head started bobbing with enthusiasm. Without warning her, I shot my load into her mouth. I let my cock soften in her mouth before pulling away. I let her lay there and went to get ready for the meeting. When I was ready to go I asked her if she wanted me to bring her anything from the restaurant downstairs. She said some orange juice, coffee, and a muffin would be nice. I went down, had my breakfast and brought hers back up to her. I set it on the dresser and told her room service was here. She laughed and said she had already tipped me. I left her $40 for the day including her lunch, told her I would be back about 5:00, and then went to my meeting. The first day of the meeting was more or less introductions of everyone and a few keynote speakers. Basically, it was the cheerleading and pep talks for the rest of the week. I had lunch with the company's CEO from back east and it was interesting hearing his views on where the company was going. When the day's meetings were over, I went back to the hotel and up to the room. It was about 5:15 and when I tried to unlock the door, the safety chain was on. I called out to Janet to unlock the door. She came running to the door and said she was sorry but she didn't want the maid coming in on her while she was dressing. She was standing there totally nude. I asked her how long it would be before she was ready. She told me she was just finishing her makeup and her hair would take 10 minutes and then she would be ready. I went in and took a quick shower and then came out to watch her. I asked her where she had gone today. She said she had gone to Balboa Park to the museums. I thought that was a different Janet than what I knew. I figured she would go shopping or something like that. The she asked me where the stuff we bought was since she couldn't find it. I asked her why she wanted it, since I was picking out her clothes for her. She said she was afraid the maid had taken it. I told her I had locked the stuff up in my locking suitcase since she didn't need the stuff and I didn't want it walking out. In truth, I figured she would wear the panties while I was gone. Then true to spirit, she asked me if she was allowed to wear underwear during the day when I wasn't here. I said, "No underwear all week was the rule, unless I say you can, like last night with the bra." She said okay and then went on to say she had a heck of a time keeping her skirt down with the breezes in the park and she was sure she had given a couple of people a show. I said good for her; practice for tonight. She looked at me and asked what I meant. I told her that it could wait until tonight but she was going to be flashing herself to a few people tonight. She turned that bright shade of red again and said, "I can't do that!" I told her she had done it yesterday at Fredrick's, and at the bar, and in the car. She said she didn't flash anyone in the bar. I told her she sure did! He said, "Oh my God! I can't believe I did that!" I told her that she looked good and nobody knew her here so there was no problem. I told her I would probably have her show some tittie tonight and she asked why. I said because she was good looking and I wanted people to see what I was fucking and secondly, because I could. I asked her if she had cum today and she said no, she didn't need to. I told her to get on the bed and I would do her. She got on the bed and I immediately went down on her pussy. Since she had just taken a shower, she smelled fresh. I licked her clit pretty intensely because I wanted her to cum quickly so we could go eat. She kind of fought it for a bit, acting like she wasn't interested in what I was doing but then she started her moaning and moving her hips around. I could tell it wouldn't be long so I kept up my tongue action. Sure enough she raised up her hips and let out a big exhale and went limp on the bed. I let her recover and then told her to get dressed. She finished her makeup and her hair and again looked fantastic. I picked out another dress for her and handed her another pair of stockings to wear. I had her wear a pair of the 4 inch heels but told her not to wear the bra. I grabbed my camera and took a couple of unposed pictures as she dressed. We went to a nice restaurant for dinner. I was in the mood for a steak and all the fixings so I picked a restaurant that I knew had the best steak in the city. It was also a micro-brewery and had some great beers. I'm not normally a beer drinker but occasionally I like to sample the local stuff. I asked Janet what she wanted to drink and she said she would have a margarita if that was okay. I said it was fine and told the waitress. The drinks came and we ordered. I ordered the steak I was craving and Janet ordered the chicken. While we were waiting for our food, I asked Janet if there was anything that she wanted to do tonight. She said that she would like to go down to the harbor and walk through the shops. I said that was a great idea. Our dinners came and I ordered another round of drinks for us. As we were eating, I asked Janet what she had for lunch. She said she had some tacos at a little stand in the park. I asked her how she got to the park. She said she took the hotel van to the park but she took a taxi back. I asked her if she had enough money. She said she actually had some left over and asked if I wanted it back. I told her to keep it. I asked her what she had planned for tomorrow. She said, if we go to the harbor tonight, she would do something else tomorrow because that was what she had planned. I told her to unbutton the two top buttons of her dress. She did without hesitating because that really didn't expose her at all. I told her that was just a start. She had just about consumed her second drink so I ordered her another without asking her. She said that she really shouldn't because she thought she had had enough. I told her she wasn't driving so why not. She said that I would have to hold her up when we went walking. I said not a problem. Her third drink came and she drank some of it and finished her dinner. She started talking a little faster but still wasn't slurring her words. She finished the third drink and I asked her if she wanted another but she shook her head no. I asked her if she wanted dessert but she declined. I paid the bill and finished my beer. I took Janet's hand and asked if she was ready to go. She said yes. We walked out to the car and I opened the door for her (ever the gentleman!) and as she got in, I got another nice look at her pussy. I closed her door and got in the car. I asked her how she liked her dinner. She said it was excellent, a real treat. I drove to the harbor and after some driving around, found a parking place not too far from the shops. Before I got out, I reached over and undid another button on Janet's dress. This was down around where her cleavage would be if she had any cleavage! A little movement to the side or if she leaned over at all and she would be exposing her tits to the world. Of course, if she leaned over at all, she would be exposing her pussy and ass to the world! I got out and opened Janet's door for her. She held her dress down as she tried to get out as lady-like as possible. I still caught a shot of naked thigh above her stocking tops. I took her hand and we walked along the shops. Janet was walking fairly easily in her heels so I figured the margaritas weren't that strong. Janet was looking in the stores and I was looking for a place to set her up for a flash. Even better, we came up to a waterside bar. I stopped and bought her another margarita and myself a scotch and water. She said she really didn't need one. I said, "Sure you do. Be a good girl and drink it." She took a sip and said it tasted good but a lot stronger than the ones in the restaurant. I asked her if she wanted to sit down or finish her drink quickly. She looked at the tall bar stools and said she would stand and finish quickly. She took a big drink and then started waving her arm and saying, `Brain freeze! Oh...." I gave her a little sip of my drink to "unfreeze" her brain. She sipped it and the scotch burned her throat but got rid of the brain freeze. She held her drink and I said, maybe she ought to sit down. She said no, she would finish her drink quickly. She knew what I was thinking. I leaned over and whispered that if it wasn't here, it would be someplace else, but she was going to show her stuff. She said, "It would be too awkward to try to get up on the stool so can it be someplace else, please?" I conceded that she might actually hurt herself trying to get up on the stool so I told her okay. She took another big drink and again froze her throat. I gave her my drink again and she took a drink. She had drank about half of my drink and three-fourths of hers. I told her to finish her drink. She sipped it this time and was able to get it all down. She set her drink down on the counter. The bartender asked us if we wanted another which I considered but I thought it was time to move on. We walked a little farther and Janet saw something in one of the shops that caught her eye. She said, "Oh, how cute! Would you look at this?" I was looking, alright but it wasn't at what she was looking at. It was her tits exposed as she leaned over. I imagined she was showing a good portion of her ass to whoever was behind us. I glanced quickly over my shoulder and saw three young guys (probably in their early twenties) looking at her ass. They were being pretty blatant about it. I kept talking to Janet about what she was looking at trying to get her to stay in the position she was in. She was starting to sway a little. I think the alcohol was finally starting to kick in. Finally she stood up and asked the counter girl of she could look at the item. The girl played right into my hand without knowing it. She asked Janet which one she wanted. Janet bent over again and pointed it out to her. The girl brought it out and showed it to Janet. Janet looked at it and couldn't decide if she wanted it or not. While she was thinking about it the girl leaned over the counter and whispered in my ear that there were three guys behind us and she thinks they are looking up Janet's dress. I acted shocked and said okay and stood behind Janet. The guys realized the show was over and left. Janet decided she wanted it and asked if I would buy it for her. It was $25 so I said sure. Janet was excited like she had just gotten a Christmas present. She was starting to slur her words a little and hadn't realized she had flashed those guys. I didn't tell her because I wanted her to think she still needed to do it. The clerk wrapped up her purchase and we left the shop. I put my arm around her and pulled her close to me, at the same time pawing her tit. She didn't seem to notice and thanked me for the present. She was wobbling a little now so I figured I had better get the flashing done and get her back to the hotel. Then I saw a waterside restaurant. They weren't very busy since it was a Monday night and I got us a couple of seats. I ordered Janet another margarita and I ordered another scotch and water (I only had half the other one!) The waitress brought the drinks out to us and I told Janet it was time for some flashing. I told her to unbutton another button of her dress. She looked around and quickly undid it. The dress was now pretty wide open now. She had her legs crossed at the knee and was showing almost all of her thigh, way above her stocking top. I looked around and there were two couples leaning on the railing looking at us. I told Janet to uncross her legs and flash the guys across from us. She shook her head no and I told her I gave her the last one, so now she had to do it. She said, "What the hell!" and did as I told her. She only had her legs spread a little and I wasn't sure the people could see anything. But then I saw one of the guys give his girl a hug and stared right at Janet! The other couple was both looking at her now. The second woman tapped her date on the shoulder and was almost pointing at Janet. Then I heard the woman whose back was to us say something like "What are you guys talking about?" She turned around, obviously clued in by the second woman and I saw her eyes and mouth both go wide in surprise! I leaned over and whispered to Janet that she should act shocked by what I was saying and quickly cross her legs. She was so glad to be able to stop exposing herself that she quickly complied. The guys kept looking because although she was no longer flashing her pussy, she was still showing a lot of thigh and tit! I told her to finish her drink and we could leave. She gulped it down and put her glass down. I got up and Janet stood up after uncrossing her legs. I'm not sure she showed them any more pussy but I know they saw all of Janet's tits. We walked back towards the car. Once we were away from the bar, Janet said to me, "That was so embarrassing! Those guys were staring at me and I was totally exposed to them! Even the women were looking!" I told her that nobody knew her and besides, in the shop, she had shown her pussy and ass to three guys. I told her they had certainly enjoyed the view. As we walked further, Janet's steps were starting to stagger quite a bit. I held onto her tit and felt massaged the nipple through her dress. We got to the car and instead of opening the door; I leaned her against it and kissed her deeply. She kissed back and I kneaded her tit. I told her I felt like I needed a blowjob. She almost giggled and asked, "Here?" I said sure. I opened the door for her and let her get in. I went around to the other side and got in. I looked at Janet and told her that if she could get me to come in her mouth before we got to the hotel, then she wouldn't need to flash anybody else tonight. Otherwise.... I left the statement open ended. I drove out of the parking lot and Janet unzipped my fly and with a sigh, put her head in my lap. She was sucking me off but the alcohol was definitely having an effect on her skills. Twice she nicked me with her teeth. I figured I would stop her before she did any serious damage! I pulled her off and told her that she wasn't doing very well. She looked at me and slurred some kind of answer. I told her the way she was sucking, she was going to hurt me. She said, "I'm shorry. I think I had too much to drink." I told her that since I wasn't going to cum before we got to the hotel, she would have to flash someone else. She just sat there and didn't seem to understand what I was saying. We got back to the hotel and I helped her out of the car. We went into the hotel and I looked in the bar and saw that there was only two people plus the bartender in there. I took Janet in and sat her down at a table facing the two guys in there. The bartender came out from behind the bar and asked what we wanted to drink, all the time looking down Janet's dress at her clearly exposed tits. I told him a margarita for the lady and I would have a scotch and water. As he went back to the bar, I leaned over and told Janet to flash the two guys at the other table. She said, "Again, I just did that!" I told her to remember the deal. She hadn't made me cum before we got back to the hotel so now she had to flash again. She spread her legs quite a bit. It was pretty dark in the bar so I'm not sure what the guys good see but it was the mental thing I was trying to accomplish. When the bartender came back, I paid him and said thanks. He said, "No, Thank you!" He smiled and turned and walked away. I told Janet that as soon as she finished her drink that we could leave. Until then, she would have to keep her legs spread. She drank her drink pretty quickly and then said, "Done." I said okay, let's go!" As we left the bar, all three guys said "Bye!" We got in the elevator and I pushed the button for our floor. Then I pulled Janet's dress up and felt her pussy. It was a little damp but not soaking wet. I unbuttoned her dress all the way down so it was hanging on her shoulders. Janet didn't seem to care. I figured she was too far gone to embarrass anymore so I just licked her tits and felt up her pussy. She had her legs spread, giving me access, so I knew she was feeling something. The elevator stopped at our floor and the doors opened. Janet pulled her dress together and ran to the room. I slowly strolled to the room and it was funny watching her standing there trying to cover herself and looking around to see who might be coming. I finally opened the door and let her in. She ran inside. I told her to lose the dress and go to the bathroom. She knew by now, not to try to take her shoes off. She went to the bathroom and I heard her peeing. I heard her flush the toilet and wash her hands. She came out and I sent her back in and told her to wash her pussy. She rolled her eyes up in her head but turned around and marched back into the bathroom. I heard her running the water for quite a while and then she came out on wobbly legs. I looked down and saw that she had washed her pussy. I told her that tomorrow, she should shave her pussy before we went out. She asked why. I said, "Because I have always wanted to see a woman with a shaved pussy!" She said, "Okay, I guess!" I told her to get on the bed and she did. I told her to get on her back and then I went over to my locked bag and opened it. I took out some things and laid them by the side of the bed. I took off my clothes and got on the bed next to her. I told her I still hadn't received my blowjob. The alcohol was really starting to affect her now. She said, "Does Roy want me to suck his cocky wocky?" She reached over and took my hard cock in her hand. She looked at it and started giggling. I hoped my plan to get her drunk wouldn't backfire on me and have her so drunk she didn't know what was going on! She put her head down at my crotch and started licking my cock. I told her, "Let's try something different. Let's do 69." She said okay in a dreamy voice and I had her lay flat on the bed. I climbed over her so my knees were straddling her head and my cock was by her cheek. I guided my cock into her mouth and then began licking her pussy. I licked her entire slot and got it plenty wet. Then I began concentrating on her clit. As I did, I humped my cock into her mouth, more or less fucking her mouth. I heard her gag a little on my cock and I was careful not to go too deep. I didn't want her barfing all over the bed! I worked her pussy over for quite awhile. Even though I was fucking her mouth, she didn't quite have the rhythm down and it was like fucking an old worn out whore. There was hardly any friction so except when I hit her throat, there wasn't much stimulation. Her cunt was pretty wet but I didn't get the feeling that she was anywhere near cumming. I figured it was time for something else. I climbed off of her and swung around and climbed between her legs. I stuck my cock in her pussy and she responded by slurring, "You're fucking me. That feels nice." She hardly had any movement at all and her pussy was pretty loose. After a few minutes of that, I reached underneath her and pushed my index finger into her ass. There was enough moisture there for lubrication since I had eaten her out. Her ass was tight and I heard her make a kind of grunting noise when I slid it in. She became a little more awake and asked me what I was doing. I told her that I was fingering her ass and rubbing my cock to stimulate it. She said it felt weird. I asked her if it hurt. She said a little. I told her that it was making my cock feel good. I told her to clamp her pussy muscles down so I could feel her tightness. I think she tried but she wasn't having a whole lot of success in her inebriated state. I pulled both my cock and my finger out of her and rolled her over onto her stomach. I told her to get up on her hands and knees and we'd do it doggy style so I could go deeper in her. She managed to pull her knees up under her and had her ass and pussy in the air. I inserted my cock into her pussy and pushed all the way in. I pounded into her and I could fell my cock hit her cervix. Every time I did, she grunted a little and said, "Too deep!" But I kept pounding her anyway. I kept that up for a few minutes and then leaned over and picked up the tube of KY jelly that I had placed on the floor earlier. I pulled out of her pussy and coated my cock with the KY. I squeezed some into the crack of her ass cheeks and she said, "That's cold, what is it?" She was still partially out of it. When I thought I had enough lubrication, I placed the head of my cock on her asshole and gently pushed forward. She said, "You're in the wrong place!" I told her it was only my finger that I was putting back in her ass again. She said, "Oh" Then I pushed and then head of my cock popped past her sphincter and into her ass. She screamed, "Ow, that hurts! What are you doing? Stop it!" I leaned over and told her to calm down; that I was fucking her ass. She was grunting pretty heavily and taking deep breaths. Her fists were both clenched tight and she said, "Please take it out, stop! You're hurting me. I told her that if she had blown me in the car, I would have been satisfied (Not really, I had this planned all along!) but she couldn't, so here we were. She kept screaming that it hurt and I was concerned the room next door might call the desk or something. I hadn't moved my cock any deeper past the initial penetration, trying to give her time to adjust. I wiped my hand on the towel I had brought with me from the bathroom and then leaned right next to her face and kissed her lips. Then I locked my lips on hers (a little hard to do, her neck was twisted sideways as was mine.) and stuck my tongue in her mouth. She was still making noises but by kissing her, I had cut most of the sound out. She pulled her lips away from mine and somewhat loudly said, "It hurts! Please take it out!" I asked her if she had ever been fucked in the ass before. She said no, never. I told her I couldn't believe she was almost thirty years old and had never had a cock in her ass before. She grunted, "I don't like this, please take it out." I told her that it felt nice and tight and I was going to finish in her ass. I also told her that I was glad I was able to take one of her cherries. She responded with, "Please stop!" I slowly started pushing more of my cock into her and she started moaning and grunting at the same time. She kept saying, "Stop, stop, stop!" over and over again. Finally I had my entire cock in her ass and I started withdrawing it which apparently caused her a different kind of pain because she started wailing again. I stopped stroking and asked her if she remembered her safe word. She said, "Yes, dammit, I do!" I asked her if she wanted to use it now. She was quiet for quite a while and I started stroking in and out of her. She kept saying "No, no, no!" but didn't use the safe word. After about two more minutes I felt myself getting near the edge. I sped up my strokes, much to Janet's consternation and her ass felt tighter on my cock. She started making a continuous sound. Finally, I shot my load in my ass. I plunged deeply one last time. The I put my hands on her hips and rolled her over with me so we were on our sides, spoon fashion, my cock still in her ass. She is sobbing. I start humping her again even though my cock is only semi-hard. She begs, "Please, no more". I whisper in her ear that she is doing fine and better get used to it `cause we're gonna be doing this every night for the rest of the week. Her reply is, "Oh my God, NO!" We laid there for about 15 minutes and finally her sobbing lessened and then stopped. I thought about doing it again but I felt she had had enough for the night. I pulled my cock out of her ass, eliciting a grunt from her. She asked if she could go to the bathroom. I said sure. She got out of bed quickly, forgetting she still had her heels on and promptly fell on the floor. She laid there for quite awhile and I was concerned she had really hurt herself. I looked over the side of the bed and she was curled up in a ball, sobbing quietly. I asked her if she was alright. She said, "What do you think? No!" I asked her where she had hurt herself. She told me that it was her ass that hurt really bad. I got up out of bed and got down on the floor with her. I gently pulled her shoes and then her stockings off her. Then I got up and helped her up. I half dragged her to the bathroom and placed her on the toilet. She sat there with her elbows on her knees. I left her alone and went back into the bedroom. I picked up her shoes and stockings and put them aside carefully. I picked up the tube of KY and placed it back in my case. I heard Janet passing a lot of gas and finally she flushed the toilet. I heard her start the shower and then curse. I went into the bathroom and she couldn't get her leg over the side of the bathtub. She was holding onto the shower curtain for support. I helped her into the tub and started washing her body as she more or less stood there. When I got to her pussy, I gently parted her lips and washed her. Then I turned her around and washed her ass, removing the remnants of KY on her cheeks. When I touched her asshole, she cringed but I was gentle. Finally, I was finished. While she stood there I used the washcloth to wash my cock. It was amazingly not that dirty and I was happy to see there was no blood on it. I helped Janet out of the tub and dried her off. Then I helped her back to the bed and laid her down. I turned off all the lights and got into bed with her. I held her spoon fashion, but my dick wasn't hard and I don't think she realized it was even there. I held her and finally she drifted off to sleep. I must have dozed off right after that. To be continued in Chapter 11