MY NEW LIFE

By Naughty Papa

Chapter 3 - The Shopping Trip

(Mf, Mggg, oral, creampie, crossdress, blackmail)

After a morning of tit and dick sucking, Cathy takes Tom shopping...

LINK TO CHAPTER 1

LINK TO CHAPTER 2

LINK TO CHAPTER 3

LINK TO CHAPTER 4

LINK TO CHAPTER 5

LINK TO CHAPTER 6

LINK TO CHAPTER 7

LINK TO CHAPTER 8

LINK TO CHAPTER 9

LINK TO CHAPTER 10

Pursuant to the Berne Convention, this work is copyrighted 2016 with all rights expressly reserved by its author unless explicitly granted.


Standard Disclaimer: This story contains sexually graphic and explicit material and as such it is not suitable for minors. If you are a minor, please leave now as it is illegal for you to be here. If it is illegal for you to read or view sexually explicit material in the community you view such material, please leave now. This story and characters are purely fictional and any resemblance to events or persons (living or dead) is purely coincidental. If you are offended by sexually explicit stories, please read no further. If you are offended by stories featuring group sex, bisexual situations, incest, sex between minors and adults, or any other situation, please check the story code before reading the text. These stories are just that, stories, and do not promote or condone the activities described herein, especially when it comes to unsafe sexual practices or sex between adults and minors.



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The rest of the evening and night was uneventful.I got a good night's sleep, still in the required clothing, and woke up the next morning surprised and refreshed.When I walked into the kitchen at 7 AM, Cathy was there already.She had cooked me bacon and eggs for breakfast and the coffee was on.Nice.

�Good morning, Cathy.I take it you have plans for me today.I have an appointment at nine, and one at ten, so I hope what you have in mind won't interfere.�

�That's fine, Tom.I need about two hours of our time, so we can get together at 11 AM?�

�Sure.�I sat down to breakfast and started eating.Cathy walked over to me and started taking off her tank top.She did not have a bra on and her big bosom just stared at me.After I had finished a bite of eggs, she took my cheeks in her hands and turned my head to her waiting nipple.�Pretend you want some milk with your breakfast, Tom.Suckle my nipple like a baby.�I wasn't sure how to do that, so I just latched on and gently started to suck her nipple in and out. �A little harder suck, Tom, and latch on harder.�I did as I was asked and enjoyed every minute.

After about five minutes, she pulled away and told me to finish breakfast.As I did, she started to remove the rest of her clothes, and stood naked before me.Her sweet pussy was as bald as Cindy's.I turned in my chair and she knelt down in front of me.Slowly, she unzipped my pants and pulled out my cock.It was hard and she bent over and took it all the way in her mouth.Her lips were tight on my shaft and they moved expertly up and down my pole as it got harder and harder.When I was getting close to cumming, she stood up and straddled me, putting my cock at the entrance of her cunt.She easily went down on my shaft and started to hump up and down.I leaned over and took her breast in my mouth, this time like a man would and not a baby.As she rode me, I sucked her.Soon, I felt her orgasm coming on, and I let my load go into her waiting pussy.She moaned loudly, and took all of it in.

But then she did something unexpected.She stood up and pulled my head into her pussy. �Suck it out, Tom.Now!�I put my mouth over her cunt lips and sucked with all I had.My sperm came flowing back into my mouth mixed with her juices and I about gagged on it.I sucked her dry and then licked her pussy clean.She then went down on my cock and licked it clean.Fast and fun.I loved it. This teenager was good.

�Okay, Tom.I'll meet you in the ladies department of Kohls at eleven.Don't be late�She quickly dressed and was out the door.8 o'clock... I had to hurry.

I finished my two appointment and went to Kohls.It was 10:55.Cathy was in the front part of the woman's department and saw me right away.She walked up and gave me a hug.�Ready to do some shopping?�

�Sure.What are we buying?�

�Why, Tom, clothes for you!After all, you don't have any really nice ladies clothes, and I want you to feel special.So we need to get some just for you!�

�Oh.That's a surprise, but I'll go along.Uh, where do we start?�This was going to be fun,I had always toyed with the idea of wearing woman's clothes, but yesterday was the first day I had actually put some on.Now that I didn't have a choice, I was ready to roll.

�First, we have to determine size.I went through a couple racks already and pulled these out.Let's go to the dressing room and try them on.�She handed me three similar dresses, sizes 8, 10 and 12.They were Summer dresses, with thin shoulder straps, and thin material that had a blue background with small pink flowers scattered around.I loved the look of them, but was hesitant about the trying on part.

�Now we also need blouses and pants,� she added.We walked over to another rack and Cathy pulled off some dress pants, again in three sizes, and a plain button up white blouse.

We headed to the dressing room and Cathy whispered something to the clerk.With a smile the clerk looked over my purchase and let me go to the room.I'm sure my embarrassment showed.Cathy followed close behind.�I'll be right out here to see how things fit.�

I went in and stripped down to the underwear she had given me before.I slipped on the size 12 dress, figuring that would be closest.It fit pretty good, so I opened the door for Cathy.�Hmm... not too bad.Is that the 10?�I told her it was the 12 and she said to try the 10.I went back in and put the 10 on.It hugged me pretty good and showed that I had some waist form from working out.The bust was a little tighter, but would have room for a bra underneath.It came down to mid-thigh.I really liked the way it looked on me.I showed it to Cathy, and she agreed.

I went back into the dressing room and put on the size 10 pants and blouse.They fit nicely, so we were done. �All done?� I asked Cathy.

�No, silly.You need lingerie!But you don't have to try that on; we know your size from yesterday.�

I told Cathy I trusted her to pick out the best lingerie at this point, so she did so.A black bra with push-ups, and a red one that had small cups and slim straps � both 36B.The underwear she chose was nylon/lycra blend, size 6.They were bikinis with kind of a wide band that went around the waist.They looked different to me, but I trusted her.Next was a slimming girdle type thing; she got a small.I wondered, but kept my tongue.Then came a couple garter belts and some thigh high stockings, one black, one white.Last was a couple bedtime short sets.The shorts were tiny, and the blouse buttoned up the front.Both were floral prints, one pink, the other blue.On the way to the checkout a couple more blouses, two dresses and two pairs of pants.

�Okay, that's it for today," Cathy announced."We need to get back home now.�

It was 1:30.I wasn't sure why we had to get back home, but I didn't ask.I pulled out my credit card at the checkout, and rang up the almost $300 purchase.I also applied for a Kohls charge, figuring it would come in handy.I was very financially sound, so it didn't bother me a whole lot.

We got all our bags in the car and headed back to the house.Upon entering, I heard giggling coming from the living room.We set the bags down in the kitchen and walked in on three naked little girls just lounging around.They all ran up and hugged me, but Cathy shooed them off.�Now girls, you know what the plan is.I have to get Tom ready.�

�We just wanted to say, HI!�Abby said as she squeezed my cock through my pants.�Hi, Tom.�

�Hi, Abby.Nice to see you; all of you!And I mean all!�

The girls giggled.Cathy took my hand and led me to the bedroom with bags in hand.She told me to stand by the bed, and she slowly started to take off her top and pants.She had on identical underwear as she bought me!She looked incredibly hot for a 14 year old.I wanted to jump her, but I saw the look in her eyes.�Now Tom, I want you to reach into the bags and put on the same exact clothing I have on.�I nodded my head and proceeded to remove my clothes until I was naked before her.

I pulled out the black bra first.I snapped it closed in the front and turned it around, putting my arms through the straps and pulling them up.It fit great, with the push up cups dangling in front of me.Cathy walked over and picked my socks up.She wadded them up and put them inside the bra, pulling my pecs out so the cup would fill.I actually had a little cleavage at that point. �Wow, like magic!�I said.Cathy smiled

Next I started to put the panties on, but Cathy said garter first.So I took the black garter and put it on, followed be the black panties.I put the garter straps over the top, but Cathy walked over and pulled them underneath the panties.She then reached in and tried to put my cock back through my legs, but I was too hard.She pulled down my panties and gave me an Incredible blow job, lightning fast.When I was done, I was left dangling, and she tucked me back, pulling the panties up tight.It looked like I just had a big mound there.

Next came the girdle-type thing.I came to realize it was a corset when she started it in the front and put the laces around back.She started to tighten up the corset, and I could barely breath.The curve from the hips to the waist became incredible as she tightened up one lace at a time.As she approached the top, I could barely breathe.The effect was that it pushed my bra up even more, and brought my waist down about 4 inches.She brought me over to the mirror, and I was astounded by the look.

I had quite a figure with the tight corset on, and if not for my face, I would have thought it was a girl's figure.The cleavage was small, but noticeable.I was adjusting to the different breathing necessary with the tight fit.

�Last will be the nylons, Tom.I'll show you how they work.���

She pulled out the pair I had bought, and then reached in her purse and pulled out a black pair of her own.She sat down on the bed, and pulled me down beside her.�Now, do just what I do.�We rolled the nylons up and then gently pulled them over our toes.She showed me to pull them tight as I we slowly pulled them up our legs.The feeling was incredible, and oh so sexy.The nylon worked over the knee andcame up to mid thigh.She then showed me how to attach the garter to the top.We did the other leg the same, and the outfit was complete.

Cathy pulled the blue floral print dress out of my bag, and again, as if by magic, she pulled the same dress out of her bag.We slipped them on over our heads and the material almost floated down across my body.Cathy walked over and adjusted the shoulder straps so they lined up, smoothed out the breast area and down around the corset.Then she took me over to the mirror again. We stood side by side and looked like twins from the neck down, except her figure was a lot more curvy than mine.

�How does that feel?� she asked me.I looked in amazement and told her it was an incredible feeling, and I was so pleased with the way it looked.She smiled real big and kissed me on the cheek.�We'll make you look even better another day, but this will do for now.Let's go out to the living room�

She took my hand and led me out there.Annie, Abby and Cindy all sat up when we walked in the room.To my dismay, the girls had gotten dressed again while we were getting dressed. Their eyes were wide with excitement and whistled cat calls as we both sat down, Cathy in the lounge chair, me on the couch.The three younger girls came over and started to play with me.That's when Joan walked into the room, stark naked.

I had to take a minute to review my plight.   Here I am, a 35 year old bachelor in pretty good shape and modestly good looking, sitting on my couch with a corset, nylons, garter belt, panties and a bra on under a very nice fitting dress. There is a 16 year old beauty sitting in my lounge chair with the exact same outfit on.Over to the side is a naked 14 year old lass holding a video camera.

I have three other younger girls sitting on me and hugging me. Abby, 12, has a tank top and shorts on. She is, sitting on my lap facing me. Her arms are around my neck and her legs are on each side of me. Annie, 7, has on a little white dress and is snuggled up to my left side with her arms round my waist. Cindy, 5, is on my right side wearing a thin shirt sleeve top and a pair of skorts. She has one hand in my stomach and the other on my shoulder. What's not to love about this situation? I find myself eager with anticipation of what will come next. Going by past experience, I have no doubt they have already rehearsed something for thus very moment.

Then Abby got off my lap and went over to Cathy. She started unbuttoning Cathy's dress down the front, very slowly. As she did, Cindy and Abby did the same to me, alternating buttons. They went very slowly, and it was very erotica. Cathy just looked straight into my eyes, and I tried to look into hers as well, but I also wanted to see her body again.

Once the buttons were all undone, the girls started pushing the material off my shoulders as Abby did the same to Cathy. Cathy moved her glance to my semi hard cock. Then looked back up at me and licked her lips. I just smiled. My cock started hardening under the panties again. Once the dress was off our shoulders, the girls had us both stand up. They were in charge, and Cathy and I were just their pawns.

Abby put her fingers into the waistband of Cathy's panties while Cindy and Annie each grabbed one side of mine. When Cathy put the panties on me, she put them outside the garter, Cathy's were the same. Very slowly the girls started to peel down our panties. Cathy's pussy was not completely bald, she had a thin patch of well manicured hair that ran from top to bottom hiding her little cunt. Very nice. My cock sprung out and stood at attention. The girls pulled the panties to the floor and we both stepped out of them simultaneously. They then pulled our dresses off.

With Annie and Cindy behind me, and Abby behind Cathy, the girls put their hands on our bare bottoms and urged us toward each other. Cathy was about 5'3", I was 5'9, so when we met in the middle, my cock was squished between us, up against the bottom of her corset. I leaned down and put my lips on hers. I felt a pair of small hands reach in between us and move my cock down so it nestled against her pussy lips. Slanting slightly downward. I was getting harder by the minute. I wanted to just grab her and fuck her hard, but being led by the smaller girls was much more erotic.

Our kiss became very passionate as our tongues started to intertwine. Both of our hands remained by our sides as we kissed. Cathy leaned into me, and I could feel her large breasts on my chest. Our juicy, wet kiss continued as Cindy took my hands and put them on Cathy's shapely butt. I gently started to knead her soft, firm cheeks. Then I felt her arms go around my neck as she pulled into the kiss.

She pulled harder, as if to try and climb me, and I took the cue. I grabbed her upper thighs between her legs and lifted her off the ground. I pulled that cute little 14 year old close to me and I felt a pair of tiny hands grab my engorged penis. I looked to see Annie reach under us and felt her hands as they guided my cock into Cathy's waiting pussy. We were both breathing hard, my breathing made even more difficult because of the corset. What an amazing feeling, having this precious teenager in my arms, both of us dressed to kill.

Cathy starred riding my cock, rocking up and down on my pole while she continued to kiss me. She was not heavy, but I knew I could not keep this up for long. I heard the other three girls giggling, and looked over to see them watching intently. Out if the corner of my eye I saw Cathy with the video recorder. Too late now!   I was so turned on by all this that I quickened the pace, pulling her up and thrusting into her, again and again. She ground her lips onto mine and started moaning with delight. Her arms hugged me harder as her breathing became more intense. She hugged me tighter, and I pulled her up, and then lunged into her as she came down.

One thrust after another was getting me so close. Then I felt Cathy tense up and start to shudder. Now or never. I drew back and plunged quickly into her one more time, and my cock let out a huge stream of cum, right into her waiting pussy. She screamed with delight and had a second orgasm as she passionately kissed me again. After a few more lunges, I was getting soft. So I stopped, held her tight and kissed her again. Then I pulled out, put her down, and collapsed on the couch.

"Wow," said Abby. "That was amazing. Your pretty good, Tom."

Joan popped in, "Yes, it was. What a great movie!"Heck, I'd forgotten all about Joan, but now that she had my attention, I couldn't help but admire her lithe nude form.

Then it dawned on me.Were they expecting me to fuck her now?Despite the two naked and available teenage girls, my cock lay limp and useless for the moment."Oh, my girls. I am done for the day; coming twice in about an hour has me worn out." I looked over at Joan, who was videotaping again, prepared to plea my case.

"Aw, Tom. Are you sure?" Annie said it with a quizzical look as she threw her dress off over her head. Not her too!

Abby and Cindy both followed her lead, and in no time all three were naked. They walked up to me and looked up at me and in unison asked again, "Are you sure?" Cindy took hold of my cock and Abby lowered her mouth on it while Cindy pumped it, trying to help me get it up again. Annie reached in and gently played with my balls, and my cock gave me away as it started to grow again.

"See, Tom.  You have more to give," said Cathy with a grin as Joan kept the video going.

What could I do? Five nymphs, all expecting to have sex with me.I was right by the couch, so I leaned back and fell into it, even surprising them, and in the process ripping my cock out of the seven-year-old's mouth. "Girls, you're going to break me if you're not careful!"

Cathy slyly said, "Oh, Tom, we have already broken you. I mean, you'll do anything we ask. Won't you?" The last two words were very stern, definitely not fooling around.

"Yes, I will," I replied glancing at the video camera that was still recording my damning tryst with very young girls. "I'm yours for sure now with the recordings you have. I'd be in prison for life if this gets out."

"That's right, Tom." said Cathy. "And don't ever forget it!"

With that, the girls got their clothes back on and headed out the door. I'm not sure if I was disappointed or relieved,Cathy was the last to leave and she had some instructions. "There are more clothes in your room with a note. Make sure you follow the instructions because we will be back." Then she came over and kissed me on the cheek and was gone. My curiosity was piqued by her statement. I went into the bedroom and saw a bag sitting on the bed with a note attached. Still dressed in my lingerie, minus the panties,   I sat down and started reading the note.

Tom:

You are such a good sport. All of us simply love you, and love the fact that you are willing to play around with us. We have been having so much fun, and I hope you have to. I think you are an amazing man. We all wanted you to know that we are truly falling in love with you!

In this bag is a nice pair of men's underwear and some pajamas. I bet you were expecting something wild! Well, we know that there are times you need to still feel like the wonderful man you are, and this is just a gift to show our appreciation for all you have done, and all we will do in the future.

Please wear these to bed tonight and see if they don't feel nice and fit you well. Tomorrow will be a day off, you deserve a rest, and we need to plan out some more fun things to do.

We love you Tom!

Signed by all five girls.

I was touched. I reached in the bag and pulled out a pair of satin briefs and some silk pajamas... very nice.   I wondered for a minute where they got the money for these, but that thought quickly faded. I was touched, and actually felt a little emotion at their thoughtfulness. I took off the lingerie and put it in the bag, and put on the clothes they gave me. Perfect fit.How do they do that every time? I put the bag in my closet, turned out the lights and went to bed.


END of Chapter 3

LINK TO CHAPTER 4




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