Chris's Surprise Prize free porn video

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Chris's Surprise Prize Part 1 My name is Christopher James who is 22 years old. I am called Chris. I am a closet cross-dresser. I live on my own in an apartment in Palm Beach, Florida and worked at a bank. I bought my clothes by mail-order not having the courage to buy things in person. I just loved the feel of the soft silky women's clothes on my skin. I often wore panties and pantyhose under my suit to work. I had several nightgowns which I always wore to bed. In fact I rarely wore male sleepwear. While I was growing up I used to wear my mother's clothes. I had entered a completion in a magazine called "Blush". The first prize was an car which would be great as my own was old and giving lots of problems. The other prizes were surprise prizes. They just gave the value of the prizes. The 2nd prize was worth $30,000, while the other prizes were lesser amounts. I had just got home from work and entering the foyer of the apartment building from the underground garage I went to my post box. I collected my post and noted amongst the envelopes was one from "Blush". It was after the closing date of the competition. I went into the elevator and heard someone calling for me to hold the elevator. It was a woman who lived on the same floor as me. Her name was Patricia and I fancied her but not had the courage to ask her out on a date and also because of an incident. The building had a basement Laundromat. I had on occasion washed my women's clothes there. There was one occasion when Patricia had surprised me when I was taking some of my delicates out of the drier. She looked at me quizzically but did not say anything. Patricia was wearing a sheer blouse and her lacy bra was visible. I caught myself staring at her bra rather than its contents. She noticed and smiled and said, "Chris are you looking at my tits?" I averted my eyes to look into her eyes. I was short for a guy and Patricia was taller than me. I felt my face get hot as I blushed. Patricia continues to tease me and said, "Or is it my bra you were looking at?" I blushed even more. I stammered, "S... sorry it's your t... tits I was looking at." Patricia said, "You can't fool me, I know it's my bra you were looking at." I just stayed silent the rest of the ride in the elevator. We reached our floor and then exited the elevator. Being a gentleman I let Patricia go first. I walked behind her and looked at her back my eyes focused on her bra straps. I remembered from school I loved looking at the girl's bra straps as I sat behind them in class. We reached my apartment first and I stopped to get my keys out. Patricia turned around and waved at me and I returned her wave. I unlocked my door and went inside. The first thing I did was after putting my briefcase down was open the letter from "Blush". I began to read the contents and my mouth dropped open in surprise when I read that that I had won the 2nd second prize. I turned to the second page and discovered what I had won was a voucher from a bridal store to the value of $30,000. The voucher was not exchangeable for cash and had to be used within a month. I was stunned I had won something of great value yet to get it I would have to go to a bridal shop and present the voucher. I was apprehensive of doing it. The next day was Saturday and I decided to go to the shop called "Cinderella's" just to check the place out. I loved walking in malls and secretly looking at women's clothes. But for now I was just going to relax with a DVD and also surf the internet while dressed of course. I made myself a cup of coffee and relaxed while sitting my couch. I read the letter from "Blush" again. I had always wanted to wear a wedding dress with lots of petticoats. I now had a chance. I just had to muster up enough courage to go into the shop. I went to my bedroom which looked like a normal young guy's room. I kept my female clothes with my male clothes. I began to undress, removing my outer male wear. I had panties and pantyhose on. I just added a silk lacy camisole and a half slip to what I was wearing. I put on a white silk blouse and a red skirt. I just loved the cool feeling of the slip on my stocking legs. I had small feet and was able to wear ladies shoes so put on a pair of white low heeled sandals. I did not shave my leg and body hair so the effect was not that good. I did not have the nerve to do that. I wore my hair on my shoulders and for work wore it in a ponytail. At home I wore it loose. I undid it and brushed it out. I would love for someone to style it for me. I kept my finger and toenails neatly trimmed and shaped. I would often paint my fingernails. I went to the kitchen and began to prepare my supper. I was a fairly good cook and loved to make my own meals. Tonight I was doing my favorite, macaroni cheese. I had the TV on and was watching soaps. I had a glass of wine as I cooked. I had everything done by the time "The Bold and the Beautiful" started. After my meal I went to my bedroom to fetch some nail polish which I used to paint my nails as I watched the TV news. After that I went to my room and while standing in the bathroom I got a tube of lipstick from the cabinet and applied it to my lips. I always coated it thickly. Back in my lounge I poured myself another glass of wine and put in a DVD. It was about cross-dressing and portraying yourself as a female. I knew it would be a long time before I venture outdoors while dressed. As I watched I sipped my wine and was delighted when I left a trace of lipstick on the glass. After the DVD I put on a Star Trek Voyager DVD. This was my other passion, sci-fi movies. Later on I got ready for bed. It was nice to undress and then put on my nightgown, which was a long pink cerise creation. It had a matching gown. I kept my panties, pantyhose and slip on. I got into bed after doing my teeth and reveled at the soft silky material on my skin. I surfed the internet for a while looking at sissy outfits. I fell asleep wondering about my visit to the bridal shop the next day. I woke the next morning and as was my custom upon waking I began to stroke myself after I lifted myself up and pulled my panties down. I gripped my tool with my nightgown. My tool was normally hard this time of the morning being excited by the soft silky material of the nightgown. I wanted to prolong my excitement so I stroked myself slowly. I began to build up in excitement till I reached the point of no return and I erupted into my nightgown. I lay and relaxed for a while and then got up and put on a clean nightgown and a pink quilted gown and went to make myself breakfast. Really had a proper breakfast during the week and enjoyed a full breakfast on the weekends. I finished eating and then went to the bathroom and where I had a long leisurely bubble bath. I got out the bath and dried myself off with one of my soft fluffy pink towels. I stood in front of the mirror and shaved while standing in the nude. This was a task I hated but an unshaved face looked really terrible. I powdered myself with baby powder. It had no smell. I went to my room and began to dress. I put a pink panty which had ruffles across the seat. Next I put on some thigh high stockings which had elasticized top to hold the up. I did not want to wear my garter belt in case they were seen under my pants. I put on one of my silk shirts after spraying myself with deodorant. I loved silky clothes, it looked masculine. Next I put on a pair of slacks and then my socks and shoes. I brushed my teeth and then left the apartment. As I walked along the corridor became aware of someone walking behind me and turned around and saw it was Patricia. I said hello and she greeted me also. I got to the elevator and held it for Patricia. We began to ride down to the foyer. During the ride down other people got in the elevator and soon it was full. Amongst the passengers was another girl Kathy who lived on a lower floor and was friends with Patricia. I ended up standing close to Patricia with my rear pressed against her. We got to the foyer. Kathy quickly moved forward and quickly closed the doors and pushed a few buttons. The elevator started going up. I asked her what she was doing. She did not reply but Patricia asked, "Chris are you wearing panties? Don't deny it I could feel them while you were pressed close to me." I blushed and said, "No I'm not," blushing further. She replied and said, "Why are blushing then?"

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Chrissies High School Reunion

Chrissie’s High School ReunionWhen the announcement arrived in the mail notifying Kelly and I that our High School graduating class was organizing a ten year reunion we spent that entire evening discussing the pros and cons of attending. I was fairly certain that I wasn’t interesting in attending but Kelly insisting on listing all the reasons why she felt we should attend.She was interested in going because she wanted to make passes at all the “stuck-up bitches” that pissed her off in high...

4 years ago
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Chrissie and TomChapter 11

Chrissie half woke in the wee small hours, reached for Tom and whimpered when her hand found empty space. Surfacing a little further, she remembered Tom saying he was going; she clasped her hands together in front of her face ... and prayed, feeling as she did so the ring on her finger; comforted, she dropped off to sleep again, fingers of her right hand on the ring. At about the same time, Tom was piloting a barge with about six hundred tons of aggregate on board down the Colne from...

1 year ago
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Chrissie Part 37

"Chrissie" Part IIIVII by c.w. cobblestone Gina spun me around in the salon chair until I was facing Rebecca. My mistress smiled. "Perfect," she said. "Tight little curls, just like a little doll. And I love them green-and-red tips. All ready for the party. You're an artist, girl." "Well, thanks." Gina waved her hand at the salon floor. "Since he's here already, does he have time to clean up a little? We were pretty busy today and we probably shouldn't wait till the morning to...

1 year ago
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Chrissie Part 39

"Chrissie" Part XXXIX by c.w. cobblestone My eyes were open but I saw only swirling blackness. My master's voice, on the other hand, was loud and clear, even at a whisper. "Chrissie. Wake up." He nudged me with his toe a second time. "Go to the living room." I dragged myself off the floor and limped after Karl as he strode out of my bedroom. I knew the drill: my master was horny and Rebecca still hadn't recovered from giving birth, so it was going to be up to me to fulfill his...

1 year ago
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Chrissie and TomChapter 5

It takes time to even load the luggage and instruments for an eighty piece orchestra, then to drive two coaches across London to the M25 and south-west to Portsmouth. It should be less than a two hour drive, but that doesn't take into account London and the M25. So the young people ate sandwiches and fruit on the move and arrived in Portsmouth at their hotel mid afternoon. Their programme for Portsmouth included selections from opera including Merry Widow and Butterfly. Incidentally, did...

1 year ago
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Chrissie Part 40

"Chrissie" Part XL by c.w. cobblestone Gina gave Taylor a smooch before passing her to Katie, who showered the baby with a new batch of kisses while Rebecca looked on with a mommy's proud smile. Katie bounced the giggling infant on her knee. "You are so cuuuuuute, you know that? Little cutie wootie?" While Katie played with the baby, Gina held out her wine glass, which I hurried to refill before resuming my serving post. I watched Katie having fun with Taylor and got caught up in...

1 year ago
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Chrissie Part 44

Interest in this story appears to have waned, so this is definitely the final part of Book Four, and probably the end of the "Chrissie" saga altogether, unless enough folks want the series to continue. "Chrissie" Part XLIV by c.w. cobblestone Rebecca and Karl both did doubletakes when I stumbled through the front door. My angel covered her mouth with her hand. "OMG, Chrissie, what happened to you?" I had to brace myself against the doorjamb to stay upright. "Um ... it was...

4 years ago
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Chrissie Rene and Charles

Chrissie, Rene and Charles I’ve told you previously how I met Rene and how he would, with short notice, send Charles, his driver, to call for me and transport me to his estate. The journey to his home was always very secretive. I would travel in a Rolls Royce Silver cloud with darkened windows and often blindfolded. Charles always in the front seat sequestered behind a privacy partition while I sat alone in the rear seat. My instructions as to how I was to dress and behave during the ride were...

1 year ago
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Chrissie and TomChapter 6

Tom was the first up; in grubby jeans and t-shirt he ate a quick breakfast before boarding Reminder to tidy up some loose ends he would normally have dealt with the previous evening. So when Chrissie arrived, having risen, eaten a cooked breakfast and dressed with care, she didn't find him on board 'Peewit', his yacht. It didn't take much effort to deduce where he was and she picked her way across the decks of SBs Wivenhoe and Xylonite to reach Reminder. He looked up from his labours and...

1 year ago
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Chrissie Part 35

"Chrissie" Part XXXV by c.w. cobblestone Karl winked at me and squeezed his cock. "Mornin' Princess." I served him coffee in bed. "Um, good morning, sir. Good morning, Mrs. Martin." Rebecca blew on her steaming mug. "Good morning, Chrissie. How's your butt?" "Uh, it ... it hurts real bad, Mrs. Martin." Karl scoffed. "Oh, quit your bitching. We seen how much you loved it last night -- fuckin' little sissy." "You squirted everywhere, Chrissie!" my angel snickered. "It...

1 year ago
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Chrissy Tanner Part 3

Chrissy Tanner - Part 3 Chapter Seven - Hotel Christina Chrissy slowly woke to the feeling of her big sister's hand gently shaking her shoulder. "Wake up, Sissy. We're here." Mia had let Chrissy sleep through the entire flight, and even adjusted her seat and removed her seatbelt for her after they landed. Chrissy was groggy, and it took her several seconds to wake up. Just like this morning, the sight of her painted fingernails had the effect of smelling salts, as she finally...

4 years ago
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Chrissie Learns A Harsh Lesson The Conclusion

Chrissie Learns A Harsh Lesson (The Conclusion) My arms were stretched straight up over my head, metal handcuffs circled my wrists and were tied to a metal ring that had been embedded in the ceiling. The rope which was hoisting me up left me suspended from the ceiling in such a mannerthat only the toes of my black 4 inch heels touched the floor. The hard metal of the handcuffs cut into the skin of my wrists and a burning ache traveled through the muscles in my arms and shoulders. I felt...

1 year ago
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Chrissie

Okay, a lot of these stories start out with a cliché, it goes something like this: I came home from work and there was a strange car in the driveway. Well shit, it does happen like that a lot. And my story does have some of that in it, but it's just a tad different. It's different because Chrissie loves me, and will do whatever it takes to protect me, no matter what. Maybe I should start at the beginning. Well the recent beginning anyway. My name is Tim Matthews. I work in IT at a mid sized...

2 years ago
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Chrissie and TomChapter 2

Tom woke before dawn. It may have been the piping of the waders poking around in the mud next to his little yacht or the lapping of the rising tide, but that is unlikely. He looked at his watch in the half-light. Ten to five ... or as he thought of it, 'oh four fifty'. He crawled out of the oddly-shaped berth in the fo'c'sle of his small, elderly yacht. ('She may be old, but she's sound and she's mine, ' he'd say.) He pulled on a pair of jeans and some deck-shoes, picked up a towel,...

4 years ago
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Chrissys Deception Pt 02

Chapter Four Dawn came early to the ranch house. Chrissy hadn’t managed to get more than a few minutes sleep all night, but Mike was rested and refreshed. When they met down in the kitchen for coffee, it was all Chrissy could do to not be snippy with Mike. Fortunately, Tracy and Mark weren’t up yet, so she didn’t have to put on a show for their benefit. When Mike suddenly took her in his arms and planted a wet kiss on her open mouth, she felt like screaming! How dare him? And he looked and...

4 years ago
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Chrissy goes camping chapters 23

Chrissy had wanted to have a pee for ages, but didn’t want to do it in front of the girls. But as they kept behind him he couldn’t just sneak off and relieve himself so in the end he turned and said I need to wee. That’s all right do it here there’s no one to see. But these shorts are so tight I can’t get my ..... thingee out. Well just pull them down a bit with your panties and squat. You mean like a girl? Yes you are wearing girl. Clothes you need to pee like a girl. Chrissy blushed bright...

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