Shemales Porn Stories
Page 120

First Time By Transsexual

When I was 21, I spent a summer in a southern city doing a service project. I was engaged to a girl and excited about marriage, but I was also extremely curious about the male body. I was one of those k**s that masturbated constantly, and almost always about sex with a man or a transsexual. The summer before my senior year, I was down in this southern city living completely on my own for the first time. Since I was doing a service project, I only got one night a week off. I wasn't sure what to do with that night since I didn't know anyone, so I decided to get d***k. Several times, I just went ... Continue»
Posted by kbking64 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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First time with a shemale

I must have been 16 back in the day, but I always looked older so it didn't really affect anyone's judgement in the sex world that I had loved since I can remember jerking off for the first time.
I was walking the streets of Amsterdam that day, the Red light Disctrict looked like paradise on earth, all those hot hot girls smiling and telling you to come in...I don't even know how much they wanted, I didn't care, just walking in those tiny streets and seeing those creatures was more than enough.

There pretty much everything there, from the porn starlet straight from Poland to the big Colomb... Continue»
Posted by joelo 3 years ago  |  Categories: Shemales  |  
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Fun with Stephanie-Gurl at the Park!!!

Fantasy Story: Fun with Stephanie-Gurl at the park.

After weeks of chatting online I was able to convince Stephanie to meet me but she had one condition it has to be in public place. Now I am not one to hook up in public but I was dying to meet Stephanie and have a little fun. I knew of a park that was nearby that we could meet at late at night and she agreed to the location. That night I arrived at the parking lot of the park around 11 o’clock and waited in my car. Of course being the sexy gurl she is, she made me wait. We had agreed to meet around 11 but I was waiting for almost 45 min... Continue»
Posted by Ryu1313 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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My wife dressed me and used me like a slut

I think you are about ready my wife “Jen” exclaimed and she rotated me towards the mirror. My cock was already rock hard and sticky soaking the silky panties as I looked at my reflection. I gazed at my blonde shoulder length wig bounded into two braided pig tails, my face heavily coated in foundation, my eyebrows and lashes painted dark, around my eyes multi shades of blue and my lips a glossy pink. I could feel the silky tiny cup bra as it rub across my nipples, I could feel the top of the multi colored leggings clasping my thighs with the feeling of the tiny skirt that just covered my pantie... Continue»
Posted by Zeffer1 3 years ago  |  Categories: Anal, Group Sex, Shemales  |  
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First BJ

I have always felt that I was a Woman born into a Man's body. Growing up I remember seeing my Mother in a girdle, garterbelt & Nylon stockings. I always felt that I wanted to wear them also. In school I watched the Girls start wearing their first bras, Nylons, garterbelts, makeup, heels etc. & also listened to them talk about it along with their "Boy" stories. I so wanted to be able to join in but of course couldn't! I had worn stolen or thrown out pieces of lingerie & of course tried on my Mothers but it still wasn't like having my own. I also had wondered what it was like to suck a Man... Continue»
Posted by nyloned1 3 years ago  |  Categories: First Time, Shemales  |  
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dressing up

have been ‘dressing’ from a young age, the usual situation occurring, finding an aunties pink satin brassiere, a long line one which just hung on me, but that didn’t matter and also the matching corset also too large, but it felt so natural to wear these items, it gradually developed into wanting to dress more and more frequently, then it was dressing from there on.

My final transformation started about 7 years ago my wife had arranged to go away for a weekend with friends, a sort of girls weekend. I was ecstatic, my chance to dress for a weekend properly with no interruption. After she ha... Continue»
Posted by manfed 3 years ago  |  Categories: BDSM, Mature, Shemales  |  
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The Hotel Part 1

I knew when this started it would be like nothing I had ever done before. I drove up to the hotel early friday morning. I was checking in for seven days.
Seven Days of non stop pounding of my asshole, Strapons, Crossdressing, f***ed fem, huge dildos, and giant buttplugs are just a few of my fetishes, and I expected every fantasy to be fulfilled this week.
As I pulled up under the awning of the front enterance I was met by a woman in a French Maid uniform. I introduced myself, and said I was checking in fo rthe week. She smiled, as she opened my car door, helped me out of the car, took my ba... Continue»
Posted by NJStraponLover 3 years ago  |  Categories: Anal, Fetish, Shemales  |  
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Unexpected Secret

My neighbor and I get together almost every day after my husband goes to work. We have become very good friends. We go shopping, watch soaps, play cards, and cook together, all kinds of stuff. Her name is Linda. She recently revealed to me that she has a secret and isn't all that she appears to be.

Linda said she is a man who has been living full time as a woman for ten years now. She said she had breast implants and electrolysis. I couldn't believe it! She is feminine in every way. Her looks, mannerisms, clothes, make-up, body language, voice, everything, is always a woman.

So, I asked ... Continue»
Posted by nova169 3 years ago  |  Categories: First Time, Masturbation, Shemales  |  
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car fun!

Some years ago, I had overnight business travel and I cross-dressed in my motel rooms after hours. I had some married men that I met online that would come see me when I was in their towns, and get some sweet head from me on their way home from work or whatever. One of my regular hookups, named Frank, pulled into the motel parking lot late one afternoon and looked up and saw me on the balcony. I was in a mini dress; heels and all dolled up, waiting for him, but was just getting a little "exposure" time in, as I waited. When Frank came in he said that he could tell that I was into being seen an... Continue»
Posted by dana213 3 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  
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Leila's Secret

I'm an ordinary guy, nothing special about me at all. Well, maybe my choice in women could set me apart from most.

It all started one rainy afternoon in Northern California as I was driving home after a party I'd attended alone the day before.

I'd stayed over at a friend's house and after a nice leisurely breakfast I headed home so that I would be back home before dark. I had to be at work the next day and wanted plenty of rest.

I was driving along Highway 1 when I first saw her. And boy, was she a vision. It had been raining all morning and the woman who stood there beside the road w... Continue»
Posted by nova169 3 years ago  |  Categories: First Time, Hardcore, Shemales  |  
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All grown up part 1

It has been about 3 years since we all moved into our own house and my s****r even with her stunning looks and drop dead gorgeous face she could not hold down a relationship. The boys she went out with were all not very open minded and ended the relationship by the time they got the bedroom and over the months you could see she was a little down because of it.

when she was 21 years old she found a boyfriend and he was the friendliest of the lot she had met and we all got along quite well. After a couple of months into this relationship and one day she asked us to go out for the night somewh... Continue»
Posted by horndogs 3 years ago  |  Categories: Gay Male, Group Sex, Shemales  |  
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Being a shemale's toy can be fun

Joliet called and asked if I would be interested in having some fun...I thought about the last time and how pissed off she got. I hesitated long enough for Joliet to whimper in the phone 'I promise to make up for my last theatrics, no bondage and I will reward you very handsomely if you attend to my needs this week end.'

Sensing desperation, I gave my demands 'reward me up front in large bills in an envelop that I will address and drop into the post office before we do any thing, you will give me your car keys before we enter any building, and I have the last word as to what I will and ... Continue»
Posted by d4david 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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Gloryhole

I have had a fantasy since college. I was in the adult viewing booth when I heard a tap. I loooked down at the hole and heard a womans voice asking if I wanted my dick sucked. Obviously I did, so I pulled it out and stuck it through the hole. At first it was just licked with some tugging on my balls. Once I was fully erect she took into her mouth. She sucked it with just her mouth at first. She then started working it with one hand while gently rubbing my balls with the other. I counldn't hold back any longer. I came with such intensity I thought I would pass out. It was the best blowjob I eve... Continue»
Posted by swordlvr69 3 years ago  |  Categories: First Time, Shemales  |  
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MY FIRST SHEMALE ENCOUNTER

I remember the first time I found myself in bed with a shemale. I had just broken up with my girlfriend. I was lonely, I was horny, and
I had zero intention of finding myself in another relationship with a woman. When I told my buddy, Bob, he told me he knew just where to take me to solve this. So he took me to this club over in West Hollywood. The place was FULL of gorgeous women. My head was swimming - they were almost all slender and dressed in very sexy attire. Short skirts and sheer nylons everywhere.
"Wow!" I told Bob. "These chicks are all drop-dead gorgeous. What's the catch? Are the... Continue»
Posted by madnessx 3 years ago  |  Categories: Anal, Masturbation, Shemales  |  
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Brandi the Shemale Cums After MNF

So, I come home from watching Monday Night Football with some guys at the local pub. I turn on the TV and some infomercial for an exercise machine comes on. The model working the machine has a great body and seeing her workout is really working me up. My cock even gets a bit hard.
Feeling a bit on the adventurous side, I open the phonebook and look for an e****t service that has shemales. I find one. Just talking to the dispatcher and describing what I want makes my cock hard again.
The hour I have to wait for her to arrive is excruciating. I’m so horny that I decide to prep myself by jerkin... Continue»
Posted by madnessx 3 years ago  |  Categories: Shemales  |  
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T*GIRL AT THE BUS STOP

The radio was loud and the top was down when I first saw her.
She looked so beautiful sitting there at the bus stop.I remember her legs, they were long and tan and clad in silky smooth thigh highs. Her skirt shifted when she crossed her legs and I could see the garters clinging to her tan skin. She turned her head and smiled at me while I waited for the light. Her eyes were so bright. I think they were green, maybe blue. Every movement she made seemed to beckon me. As if she was calling me to her.

I couldn't help but stare at her tits - they were fabulous. A car behind me honked. shatterin... Continue»
Posted by madnessx 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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Flying High



The plane landed as scheduled. Luckily it had been a very smooth flight. I made my way through the busy airport. While I was waiting for my luggage my eyes went everywhere looking for beautiful girls. I saw my luggage come around and went for it. At the same time a voluptuous brunette reached for the same bag.

“Excuse me,” I said. “I’m pretty sure this one is mine.”

“Oh I’m so sorry, the look like mines.” Her voice was soft and sounds a little hoarsed. I looked her up and down. She had a very latin style, which my cock i... Continue»
Posted by Pedeco 3 years ago  |  Categories: Shemales  |  
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Massage parlor surprise

I have to admit one of my biggest turn ons are shemales/ladyboys. In all my little ventures to asian massage parlors for some relaxing relief only once did I get a total surprise. About a year ago I visited one of my favorit little places and Mama said I should try her new girl....I might like her. So I agreed to meet with her. Waiting in my little room in walks a very hot sexy little asian girl and we started our massage session. While getting my rub down I started letting my hands wander to her thighs and lower butt to rub and feel then and to let her know i was cool for some extra if on the... Continue»
Posted by longrod4u 3 years ago  |  Categories: Shemales  |  
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My late night dinner with Keilana Love



I maneuvered my car through the heavy traffic. I was on my way to see Keilana Love, the love of my life and the most beautiful woman in the world. Work had kept Keilana and I away from each other for the last two weeks. Longing to see my darling lent urgency to my trip. Keilana and I had planned to have a late dinner and well we would see where the night would lead us.

I screeched to a halt in front of Keilana’s apartment block. I jumped out of my car and bounded up the stairs. Keilana’s apartment is on the fifth floor, but ... Continue»
Posted by Pedeco 3 years ago  |  Categories: Shemales  |  
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The only guy who's been able to get this tran

His name is E***. He is 19, has a very sexy deep voice (though he doesn't like his voice, so I had to just settle for his typing), a virgin (but that's not a factor), he's got a 9in gorgeous cock and is able to self suck to half his shaft.
I've helped him cum through caming before, but wasn't turned on enough to get off myself. I haven't been able to do that for in a long while. Though before today. I hadn't see him give him self head yet.
Now thankx to a friend, who I sucked off just so he could release some well needed tension. But all that did was get me horny.
So I got home, a li... Continue»
Posted by ThirdEyeGirl 3 years ago  |  Categories: Shemales  |  
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