Hot transgender and crossdresser stories
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The beautician came next and when she had finished Sammie was hard pressed to recognise the young woman that stared quizzically at him from behind the mirror. Who is she? He thought before wondering. Where have I gone?
Finally it was into one of the little boutiques that sold just about everything that a girl needed. “My daughter needs a new outfit announced Winnie Morgan haughtily. This student-gunge look just won’t do!”
And that was that. Over the course of about a fortnight, Sam Pearce had ceased to exist and without any fuss or resistance, Sammie Morgan had seamlessly taken his place.
“As far as the world is concerned, you are a girl now, so it is up to me to teach you to behave like one!” Winnie had proclaimed imperiously.
As far as Sammie was concerned, she didn’t feel like a girl, in fact she didn’t feel any differently to before. The only change that she was aware of was an increase in confusion… A lot of confusion.
However she had gathered what remained of her wits and asked Mistress Morgan a simple question. “If I’m a woman, why have I still got a willy?”
Winnie had glared at her. “Because, you are a shemale you silly little bitch, so get used to it! You are also my legal property to use however the fuck I like, so get used to that was well. But at least …
“I could have fun training you, dear heart.” The man mused in a high-pitched cultured voice.
Much to Sam’s embarrassment, his penis twitched and began to stiffen. This caused the man to chuckle again. He shook his head. “You’re a bit small.” He said sounding disappointed. Never the less his eyes twinkled as he continued to gently fondle Sam’s genitals for a minute or so before moving away.
Small? What’s he on about? Sam though, his manhood oddly affronted. I’m six inches soft and more than seven hard! What does he mean, small?
A couple of women appeared in front of him again, one of them being the blonde from earlier. “Changing your preferences, Winnie?” Her shorter companion enquired bitchily. “I didn’t think you were into boys.”
The tall blonde snorted. “I was thinking more along the lines of entertainment…” But the look on her face told Sam that her interest was anything but innocent. Her head turned slowly until her gaze fell on Rachel: she smiled again.
People began to circulate more purposefully and several of them could be seen writing things down on small squares of card. Each card was then slipped into an envelope and placed on one of the podiums; some of which acquired five or six while others only one, or in Sam’s case: none. He didn’t know whether to be relieved or disappointed, but then it hit him with the force of …
It is the late 2030’s and somewhere in a small run-down town in South Wales there is a rather shabby looking Industrial Estate that is long past it’s ‘sell-by’ date. Over to one side of the ram-shackled collection of buildings is an old and dilapidated warehouse long in need of a coat of paint… The warehouse, however, sports a large new-looking sign board proclaiming it to be the home of “SECOND-LIFE AUCTIONS Ltd.” The warehouse has no windows and only a couple of doors… It is not as run-down as it looks…
1. Collection and Preparation.
As student parties go it had been quite unremarkable and had followed the traditional pattern of immature boys trying to impress young ladies by drinking more cheap alcohol than was good for them. Although why the sight of drunken lads vomiting in the various corners of the room would impress anyone is mystery lost in the mists of time.
Sam had only gone to the party because it was sort of expected — his mates were there and so was he, where they led — he followed, which is why he had mates… They were there to lead each other into trouble. Besides, as the only alternative had been to hide away in his room and write an overdue essay on the causes of the Korean War, the party had naturally won hands down.
The party which had been lively …
Hi, my name’s Terri I’m 24 5’6 220 pounds, brown eyes with thick kissable lips and equipped with rich mahogany complexation. I’m about 90% hairless meaning the only hair you will find on me are my eyebrows and long black eye lashes. I decide on the bald look at 17 when I went to my senior prom in drag.
Some may consider me chubby but I’m not a lazy fat fuck. I’m a bike massager, I do at least 4 miles a day and that’s what got me from 265 to 220 in a little under 10 months and that has my measurements at 36- 36-38 ½, nonetheless my fat is stored in the right places.
Riding around greater Tampa Florida delivering mail on a bike isn’t my long turn goal. But it helps pay the bills while I’m in grad school and allows me to keep my nights free. The freedom of riding around town with my gloriously round ass cheeks hoisted for the world to view, gets my 7 inch cock motivated to see the world.
When I’m at work I like wearing a jockstrap under my cargo shorts. Because a jock strap keeps my ass cheeks framed and wonderfully parted. However when I’m out and about and not at work I prefer the feeling of G-string or thong underwear. I don’t wear them to work, because if I am ever hit by a car or god forbid a truck. The last thing I want to have my …
“Well hello,” I said, as she strolled into my office & sat down, “I was starting to wonder if you were going to show or not.”
“You know I’d never pass up an opportunity with you honey,” she replied, coyly flashing that coquettish smile at me that I loved so much.
“Did you lock the door behind you??” I asked.
“Sure did, & yours is the only car left in the parking lot.”
“Good, well let’s get down to business then,” I said, rising from my chair.
I had done well for myself over the course of my life, graduated valedictorian in high school, was a two time All American in football, graduated Suma Cum Laude from college, built a successful finance company from the ground up, but something was always missing. I had always been pretty good with the ladies too, having had my share of girlfriends & casual hookups along the way, but had never felt like I was in love. I threw myself head first into my career & that kept me occupied most of the time, but I still had all of this money & success & no one to share it with.
That was until I found Juliana & my entire life changed.
I was at the office one night, late, & I decided to take a break & surf around on the internet a little. I was browsing through some singles ads & I saw a banner for a TS dating website. I …
One night, a few weeks before school started back, Edward asked me if I could dress very sexy and take a ride with him. It scared me a little to be away from my comfort zone but I reluctantly agree.
I wore my skin tight black dress, black lingerie complete with thigh high stocking and matching bra and panties. My makeup skills were getting much better and my hair continued to grow. My mannerisms around him were certainly natural and it felt kinda slutty to be sneaking out with him. I made my way through the dark back yard and to his truck, where he was waiting.
When I asked where we plan to go, he asked if I remembered one of the first fantasies I had shared the first night? I could not seem to recall so he reminded me of the conversation where I admitted that I liked to tease men and that it turned me on to have the attention of several men at once. He reminded me of how passable I had become and made me secure that I could walk into a store or a crowded room and everyone would stare because they thought I was hot, not a guy. He told me not to be scared and that he would protect me. That’s when he pulled into a parking lot.
I read the sign – Heidi’s Adult Books and Videos. I had been driven past this location for years but had never know what …
“The water is fine,” he whispered in her ear as he moved his hips from side to side and squeezed her breasts gently.
Janet groaned and raised her hands to cover his. “This, this isn’t, uh, getting any messes cleaned up.”
Luke kissed the side of her neck and out onto her shoulder. Janet moved her head to the side and whimpered softly as he caressed her breasts. His palm rubbing her nipples shot jolts of pleasure straight to her sex. When he crouched down slightly and moved his hips from side to side, his dick centered up between her ass cheeks.
Janet whimpered and pressed her ass tighter to his hot dick. “You, you’re going to make another mess.”
“And the problem with that is,” Luke whispered as he kissed the top of her shoulder.
“The, uh, score is already two to one. I hate taking advantage of you,” Janet said in a breathy whisper.
Luke’s right hand moved off her right breast and Janet squeezed and pinched the nipple. She took several deep hissing breaths. A moment later, Luke whispered, “Put a hand on you dick and rub it.”
Janet moved her left hand to her dick and made a fist around the head and upper shaft. She stroked herself slowly. Between Luke’s hand on one breast, his dick rubbing in the crack of her ass, the fingers of her right hand pinching her right nipple, and her …
Luke and Janet had been friends since Janet moved in next-door nine years ago. She had been the only one to show up at his tenth birthday party. Back then, Luke had been short, fat, and wore enough silver in his mouth to plate the bumper on an old Buick.
Now that had all changed, Luke had grown taller, the fat had melted away as he became more active with sports, and his teeth were straight and pearly white. The only thing that had remained the same was his friendship with Janet.
She was home schooled and didn’t mingle much. This had always confused Luke. While Janet wasn’t a raving beauty by any means, she was the typical cute girl next-door type. Luke paused in dealing the cards he held and thought about that. He had never seen Janet in anything besides baggy clothes. She had always refused his invitations to use his family’s pool.
Looking across the coffee table at Janet, he asked, “Why don’t you ever come over to go swimming when I ask you?”
“I don’t swim for one and I don’t own a bathing suit for another. Anyway, my mom wouldn’t allow it,” Janet replied as she picked up her cards and looked at Luke expectantly.
With a little jerk, Luke continued to deal the cards. “I wonder when the power will come back on?”
“When the power company fixes the problems the storm …
Bound, naked and being spitroasted by two cocks is not how I thought I would lose my virginity. I know what you’re thinking, I’m the idiot that got myself into this… Well.. Before you draw any conclusions, let me tell my side of the story first. I also need to state for the record that I am completely 100% straight. Being rammed by two cocks wasn’t on my bucket list, let alone something I would ever fantasize about.
You see, this all started when my drunk of a dad took a job as a maintenance repairman for a luxurious apartment complex in New York a month ago. The job did come with perks. We got to live in the smallest available apartment. When I say small, I mean small. I’ve seen bedrooms bigger than our apartment. Of course, it’s better than nothing. Seeing how we got evicted from the last place, we really didn’t have a choice.
Also before I really dig deep into the story, I should probably introduce myself. My name is Austin Patterson. I considered myself a somewhat normal kid. I wasn’t into drugs, nor did I party much. Mainly because I wasn’t part of the popular crowds and I never got invited to any parties. I wasn’t a loser or anything. No one bullied me. I was pretty much invisible. I’m 100% positive no one would even notice if I never showed up. …
I felt so groggy, a haze covered my senses. I didn’t want to open my eyes, they still felt so heavy. All of a sudden a weight was put on my chest. I felt something tapping against my lips. I went to brush it away, but my hands were still bound from last night. Last night! I totally forgot about last night! I open my eyes to find a giant cock pressed against my lips.
“Morning sunshine!” My eyes journeyed up the cock to find Angela staring down with a big smile. She tapped her dick once more against my lips. “Be a dear and open up for me.”
I still can’t get over the fact that Angela and Diana have cocks. I’ve never felt more trapped. Bound and at the mercy of their will. I wanted to protest, I wanted to deny them, but how could I?
“Don’t be a sour puss Austin,” she said, sticking out that bottom lip to emphasize her displeasure. “I promise if you try and put forth the initiative, you’ll love being mine.”
“Just put in the ring gag and fuck his face, he’ll learn eventually it’s better to willingly suck cock over having a dick forced down your throat.” I followed the sound of Diana’s voice to find her sitting on the chair watching us, completely naked.
“Huhhh, I don’t want to force fuck his mouth, I want …