Tommy's Unplanned Sissy Life Part 1 free porn video

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This should not be read by anyone under eighteen. Tommy's new sissy life By Deewet Tommy didn't realize that Gary was hitting on him the first two nights at the in/out bar. Never in his life had a man or woman hit on him before. Women thought he was cute, but they had no desire to be with a cute, 4'11" inch tall, 89 pound man who looked like he was twelve. On the third night, Gary was very straight-forward to Tommy. "I'm going to tell you something," said Gary, leaning forward over to table to talk softly. Well, as softly as a 6'6" man can talk. "You can get up and leave if this bothers you, but have you ever been in a gay relationship before?" Tommy was caught totally of guard and couldn't talk. "I find you very attractive," Gary continued. "Would you like to go to my place?" Tommy always figured he was straight, but since he had never been with a woman, he really wasn't sure. Gary didn't give Tommy a chance to respond. "I've fantasized about how cute you would look in a short leather shirt and pink top. I dream of carrying you to my bed and stripping you down to sexy underwear and making slow, gentle love to your cute body." Tommy couldn't breathe. Gary could pick him up like a child and the thought of that, surprising excited Tommy. He felt very strange down in his groin. "Does that make you wet?" Gary asked. For the first time, Tommy was glad he was small. Maybe he would look hot dressed as a woman. Gary stood. "I'll wait out in my car for fifteen minutes. If this isn't for you, don't come out. But, if you do come to my car, expect a wonderful night in my arms." Tommy didn't watch him leave. His mind whirled as he stood at an unexpected threshold in his life. He was a lonely man who was never taken seriously by men or women. He worked from his small apartment as a freelance writer so he never had a chance to meet anyone and Gary was very nice. It was clear what going out to the car meant to Tommy. He was the little one. He would be the one dressing up as a girl. He would be the one giving the blow jobs or taking Gary in his rear. Was he ready to go that far? Could he change his mind after getting in Gary's car? Gary waited in his car, slowly drawing on his cigarette. He hoped he hadn't jumped too fast, but he had told his customer about finding Tommy and they couldn't wait any longer. Perfect ones like this little guy didn't grow on trees. They expected Tommy to draw a high price at the auction. He glanced at his watch. It was almost fifteen minutes. If Tommy didn't come to him, then it would be harder and more risky, but Gary was ready to do a snatch. The money at stack was too high. In a way, he felt sorry for Tommy. Being that little must be a nightmare, but soon he would be living a life more suited to his size. Gary sat back and smiled. From the front door of the bar came Tommy, almost looking like a little girl sneaking out into the parking lot. His eyes were blue and large when he opened the passenger door and sat down. "This is my first time," Tommy said. "Can we go slowly?" "As slow as you would like," replied Gary. Tommy almost felt sick as Gary drove to his place. He couldn't stop himself from glancing down at Gary's crotch, wondering how big he was inside those jeans. How bad would it hurt? He started to get scared when Gary drove out of the city and into the country. They drove for thirty minutes until Tommy got up the courage to ask, "Where do you live?" "I have a place out here where we don't have to worry about privacy." This didn't ease Tommy's nervousness. What if Gary was a killer or something? Gary turned on to a long gravel drive that ended at a mobile home. "It's nicer inside," Gary said getting out of the car. "Come on in and I'll fix you a drink." Tommy obediently got out and followed Gary into the trailer. The mobile home door slammed closed behind Tommy when he stepped into the living room. His heart sank when he saw two huge guys wearing ski masks. He was going to be raped. "Please, don't hurt me," he managed to squeal, his voice sounding like a little girl's. "Take off your clothes," commanded Gary. Tommy fumbled with the buttons on his shirt. On of the hooded men grabbed the front of the shirt and pulled it off him, popping the buttons. "Now the pants," Gary said. Never had Tommy felt so little and helpless as he stood in the center of the room, his naked, almost hairless body dwarfed by the big men surrounding him. Gary tossed him a short, pink nylon top. The sleeves puffy with white lace. "Put that on." "Please," Tommy cried. "I don't want to -" His sentence was cut off by one of the men behind him stuffing a gag in his mouth. The guy pulled the gag tight and Tommy felt him latching the leather strap behind his head. A tube dangled from the front of the gag with a bulb at it's end. Gary took the bulb and began to inflate the gag filling Tommy's mouth. He continued until Tommy's cheeks bulged. All that came from Tommy was a muffled moan. Gary forced Tommy onto his knees and then pushed his head forward until his forehead was on the smelly, carpeted floor. In this position, Tommy's little tight butt stuck up in the air, and he cringed waiting for the first penetration. It wasn't what he expected. Something small was inserted and then he felt warm water begin to fill his bowels. The water continued until he felt ready to burst. "Now hold that until I tell you different," Gary said. The pain in his gut was horrible as waves of noisy cramps moved inside him. He cried and screamed, but with his mouth securely full, the only sound in the room was the breathing of the waiting men and his muffled grunts. It seemed like forever when Gary lifted him and carried him to the toilet. His bowels exploded to push out the watery mess from his gut. The men laughed. Gary put him back in the position on the floor with his butt in the air. This time he pushed something big into Tommy. When Gary pushed the object, he forced Tommy's face into the carpet. With almost a popping sound, Tommy asshole accepted the huge butt plug. Tommy again screamed into his gag. He felt as if he were being ripped apart. The plug grew bigger as Gary pulled it up. Now both of Tommy's orifices were securely filled. "Stand up and put on the diaper and plastic pants," Gary said. Tommy stood and saw a thick pink diaper, pins and shiny pink plastic pants waiting for him on the couch. He slowly walked over and looked at the stuff. What was going on here? "Go ahead and put the diaper on the floor," Gary said. "Then lie down on it and pin it tightly around your waist." Tommy took the diaper from the couch and laid it out on the floor. He looked over at the men, feeling so small and helpless with a plug filling his butt and the tube and bulb dangling from his gag. He sank to his knees and cried. "Put on the diaper," Gary repeated. Tommy sat on the diaper and laid back. Tommy pulled the soft diaper up between his legs and Gary handed him the diaper pins. Tommy stuck himself once as he pinned himself in the diaper. He stood and picked up the plastic pants. He stuck his legs through the elastic openings and pulled the noisy plastic up his hairless legs. The elastic bit into his thighs and waist, but the rest of it balloon around his diaper. "Make sure all the diaper is inside your plastic panties," Gary instructed. Gary came over and gave Tommy two rubber cuffs, instructing him to attach them tightly on his ankles. Tommy sat down on the couch and followed the instructions, buckling them closed. The rubber felt cool against his skin. Next, Gary told Tommy to stick out his wrists and he put similar purple rubber cuffs on his wrists. Tommy watched his eyes, wondering why he was betrayed. "Lay on your stomach on the floor," Gary said. Tommy obeyed. He felt his ankles pushed together and something attached to hopple them together. The thickness between his legs from the diaper made this very uncomfortable. His arms were pulled behind his back and attached together with a very short chain. The last thing was a blindfold strapped around his head. Now he was completely helpless. Gary paid and then waved his two friends in the ski masks to leave. He could take care of things now, with the little guy all bound and gagged on the floor. He made a call on his cell phone. "Everything is wrapped and ready for shipment." "We'll be there in thirty minutes to pick him up," the voice on the other side said before hanging up. Gary took Tommy's old clothes and put them in a plastic trash bag to be disposed of later. He looked down at the helpless little guy, his butt looking cute in his diaper and pink plastic pants. Tommy didn't know that the clothes in the plastic bag were the last boy clothes he would ever wear or that he would be fixed so that a diaper would always be needed. Gary sat on the couch and waited, listening to the soft whimpers from Tommy. This one was a real find, short and little, perfect for one of their rich, perverted clients. Gary felt himself growing hard as he thought about the future life for little Tommy. He looked at his watch. Still twenty minutes. It wouldn't take that long for Gary. His cock was throbbing thinking about Tommy. He pulled Tommy up to a standing position. He was so short compared to Gary that his mouth was at Gary's cock level. Gary released the air pressure in the pump gag and unstrapped it from the back of Tommy's head. Tommy cried when he popped the gag from his mouth. "Please, let me go," he cried, swaying slightly to keep his balances with his ankles hoppled. Gary said nothing as his unzipped his pants and pulled out his large swollen cock. He marveled how it compared to Tommy's little face. It seems huge as he brushed it against Tommy's lips. Tommy pulled back and almost fell. Gary took his hand and held his head as he guided his penis back to Tommy's mouth. Obviously realizing he had no choice, Tommy opened his mouth and took in Gary's cock. Gary looked over and saw their reflection in mirror on the wall. It looked so wild to see little Tommy, 26 years old, dressed in a pink night shirt, wearing thick diapers covered in pink plastic pants, blindfolded, his wrist and ankles bound, filled with an unseen butt plug and standing there with a cock stuffed between his full lips. Gary started humping Tommy's mouth, his cock so big that only a third could be forced into Tommy. The feeling around his cock was explosively pleasurable. Gary's legs felt weak. His face grew numb as he felt ready to cum already. His cock throbbed and he began to shoot cum in Tommy's mouth. Instead of pulling back, Gary was surprised when Tommy sucked harder at the cock in his mouth, causing Gary to shout with pleasure as his cum was swallowed by the diaper-clad sissy.

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Saturday NightAfter the wife’s date for the night cancelled on her at point 99, the wife and I went out for a Few drinks at our local Watering hole, just to spend time alone (got our eldest daughter to Babysit)Wife was all dressed super sexy and when we walked in you could see how some men were looking at her.Was so HOT!!!We sat and had a few drinks when she got a message from one of our friends saying how Horny he was and stuck at work.She asked him till what time he is working and was told...

3 years ago
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Unplanned Pleasure

Unplanned PleasureBy: Londebaaz Chohan Everybody was thankful that the jobs were saved and the bank; instead of closing its doors forever went into the merger plan with another larger bank. It was the part of the deal that none of the employees shall be sacked but if anybody found a better job and wanted to leave, he or she shall be treated fairly and given all what was due to them. The bank also announced the special packages, particularly for the senior employees who were expected to take the...

3 years ago
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Brother8217s Unplanned Romance With His Cousin Sister 8211 Part 2

Hello guys, I am Raghav Batra back with 2nd part of “Brother’s unplanned romance with his cousin sister”. After that incident (read 1st part) I was feeling very ashamed and was not able to face her. Somehow I passed brother’s marriage. Next day there were some after-marriage rituals, we all were invited, but I decided not to go there ( as there will be only family members and I had to face her more which I don’t want to ). I made an excuse that I had some important work with my friend and I...

Incest
3 years ago
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Unplanned Pleasure On A Hill Station

Hi Friends.. This Rohit.I am back with my new story. After getting 100% positive feedback for my stories “My wife’s Pleasure My priority” and “The return of My wife’s Pleasure My priority”, I was too excited to write my next experience. However, I wanted to live up to the expectation of my fans so did not want to take a chance and disappoint them. One fine morning, I got a fan email and it was from a girl named Nisha. We started exchanging emails and started sharing our experiences too. It went...

4 years ago
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Unplanned Sex With Colleague Which Gave Ultimate Pleasure

Hi friends.. My name is Nikita. I am 26 year old now. Naturally I am a very horny girl but these many days I had kept satisfied myself with masturbating only.I had lost my virginity to one of my cousin at the age of 18 itself who now works in the army and from then I never had an utmost urge to have sex with anyone even I had a lot of liking for many guys. My vital stats are 34d-32-34 and being from northern India I m extremely fair. My height is 5.4 and slightly on the plumper side which adds...

4 years ago
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Unplanned Fun Time With Maid

Unplanned Fun Time With Maid Hi, I am in the management of a leading MNC married happily with kids. My work demands that I am out to office as early as 7 AM and don’t return before 2030h.my personal sex life is great as my wife is a socialite and we enjoy ourselves to the core. I hardly know the house helps as I don’t get to see them due to work.it so happened that one day, after a customer call, I found time to return home around 1500h. I called my wife in advance, who told me that she is...

2 years ago
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An Unplanned Initiation

An Unplanned Initiation Introduction - Just after posting my first story here, I happened to read 'Loss of Control' by Julie O, and that got me thinking of how I might take one part of that story and expand upon it. The lead character there gets transported across an international border, but that action is just briefly mentioned. I thought about how that moment might be interesting if there were a little more detail (well actually a lot!), so I wrote a similar story based around...

4 years ago
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Unplanned Vacation in a Nudist Camp

Unplanned Vacation in a Nudist CampFew years ago my girlfriend Mitra and I were on vacation in Greece. We booked a tent at a nice camp by the sea on the Island of Ios. Pictures of the camp were fabulous and we couldn’t wait to get there. However, when we arrived there was a big surprise waiting for us. By the entrance, there was a sign with two words that changed my perception of vacation's forever. The sign read: “Nudist Camp”. When I saw it, my heart jumped. I felt both shocked and a lure of...

Exhibitionism
3 years ago
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My Sissy Cuckold Life

Hello everyone, my name is Mike and i am now a sissy cuckold. If you don't know what a sissy or a cuckold is i will explain, a sissy is like a cross-dresser but usually dresses up in pink frilly women's clothing and cuckolding is similar to a hotwifing where she goes out on dates and fucks other men without her husband/boyfriend around but with cuckolding it usually involves the husband/boyfriend to be present so she and her lovers can humiliate him while they are having sex. My life didn't...

Fetish
3 years ago
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Sissy Bachelorette Party

'You want it again?' She said, as she climbed between my legs, spreading them with the force of her knee. 'Yes Mistress.' I said, turning my head to the side. Her gloved hand grabbed my chin and turned it towards her. 'You want to be my girly lesbian bitch?' She said, as she tweaked my puffy nipples with her other hand, the dry latex chafing me. 'Yes Mistress - I want to be your girly lesbian bitch,' I rubbed my horny cunt against her stocking clad leg, ignoring the pain, wanting, no, needing...

2 years ago
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My Sissy Life Part 10

Part 10 After a while I heard the doors open, shut and the van started to move. I heard my brother saying to my father that he was happy that Uncle John was coming over tonight. "I haven't seen him in along time, it will be cool to talk to him some more," Jim said. I could hear my family talking to each other as we rode home but I couldn't really make out what anyone was saying exactly. After a while I felt a bump as we pulled into our driveway. The van stopped and everyone...

2 years ago
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The family ndash Sissyrsquos Babysitters Part

The family – Sissy’s Babysitters Part-2Sarah had left, I heard the front door close and her car drive off.....I couldn’t believe what was happening. Sarah and me had done some things, had fun with others, but she had dressed and prepared me not for ‘our’ fun...to leave and let her parents use me, they obviously knew about ‘our’ pleasures....it was James & Helen the couple that I sat with, talked to before marrying their daughter...was it something they always knew, or something they had...

1 year ago
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My life As A Sissy Faggot

My Life As A Sissy Faggot Ladyboy Paula was taller than me, especially on her heels, and hot looking with her long black hair and makeup. I had thought about having sex… My Life As A Sissy Faggot Ladyboy Paula was taller than me, especially on her heels, and hot looking with her long black hair and makeup. I had thought about having sex with a transsexual and sucking my first cock for years till I finally came across her ad and showed up at her place, ready to take the plunge. We stood...

Transexual
2 years ago
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My Sissy Life Part 16

My Sissy Life Part 16 On the ride home all I could think about was that soon, I was going to have breasts. Real breasts. C cup size breasts. When we got home my mother said that she was going to start dinner and that I should be ready to serve in about a half hour. After dinner my father told my mother that he had a few things to do at the office and left. I told my mother that I wasn't feeling good and asked if I could goto bed. She said yes and I went to my room. When I got...

4 years ago
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2088 Its a Sissy World

2088: It's a Sissy World Charles Pauline - Data Processor Cindy Pauline - Charles' wife Ms. Miriam Jensdotter - Charles' Boss James Marie - Charles' work friend Ms. Marysdau - James' boss Creampuff - A Sissy Store Worker Babykins - A Sissy Store Worker Suzi - The Sissy Store Owner Butterscotch - Creampuff's Roommate Supervisor Gabriellez - Creampuff's Apartment Supervisor Janice and Roger - Passengers on the Looper Ms. Hardcastle - Milking Salon Director Nurse Hamilton - Milking...

4 years ago
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My Life As A Sissy

My Life As A SissyFrom the earliest awakening of my sexuality I felt a strong desire to be girly. I was the smallest boy in my grade at school and my slender body was milky white and nearly hairless. I felt that my penis was unusually small as well, and I didn’t have any pubic hair until at least a year later than the other boys. My first reaction was to shave it off, which I did on summer vacations so it wouldn’t be noticed in the shower at gym. I was back to being deliciously smooth, and...

1 year ago
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My Life As A Sissy rewrite

This is equally on the topic of "FIRST TIME STORIES" or "TRANSSEXUAL" and is an updated version of the story I sent less than 24 hours ago *** My Life As A Sissy From the earliest awakening of my sexuality I felt a strong desire to be girly. I was the smallest boy in my grade at school and my slender body was milky white and nearly hairless. I felt that my penis was unusually small as well, and I didn’t have any pubic hair until at least a year later than the other boys. My first reaction was...

Transexual
3 years ago
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Meinen Mann zur Sissy erzogen

Achtung diese Geschichte ist noch voller Rechtschreib- und Gramatikfehler. Jeder der m?chte kann diese Geschichte als Vorlage nehmen und sie verbessern. Jetzt reicht es mir. Ich hatte die Internet Seiten meines Freundes gefunden. Er surft also st?ndig auf Adult Baby Sissy Seiten. Ich hatte mich schon l?nger gefragt warum er im Bett nichts zu Stande bringt. Das kann er haben, ich werde ihn einfach in ein kleines Babym?dchen behandeln bzw im Grunde verwandeln. Er war eine Woche zu einem al...

1 year ago
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Chrissie The Saga of a Lovestruck Sissy Maid

Chrissie by c.w. cobblestone BOOK ONE "Mrs. Martin" Part I My right leg had a mind of its own. Rebecca frowned. "Why you keep bouncing like that? What's wrong with you?" "Um, I ... I ... nothing." "Bullshit, nothing. Something's up; you been acting weird ever since we got back from Paris. What the hell's going on, Chris?" I balled my fists. Clenched my jaw. Closed my eyes. Drew a breath. Took the plunge. "Okay. Okay. It's just ... well, now that we're...

2 years ago
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Sissy spit roast sleep over

Pt 1: Long black limoSissy Saraya was very excited because her new mistress had told her they were going to continue with her corset training tonight, she had been wearing her waist trainer and inflatable plug all day along with her favourite pink maids outfit and cute sissy 6" white heels and stockings with pretty pink bows, She had been watching BBC porn all day and was dreaming of cock while she finished her chores, Mistress text to say her driver would be arriving at 6pm sharp, Mistress...

2 years ago
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The SissyMaster

THE SISSY-MASTER CHAPTER 1 I have read many tales and stories on this site over the years; some of them 'autobiographical' and some of them complete fantasy. It strikes me that most of the stories have been written by the, either real or wannabe sissy girl and therefore is 'her' fantasy from a sissy's perspective. So I have written my stories of my experiences, beliefs and methods from the perspective of the male. This is for the REAL MEN that read this site, a guide to the...

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