Shemales Porn Stories
Page 7

Oh My, You Have a Cock...

It was a regular Friday night no different from others I'd experienced before. I was lonely having broken up with my girlfriend earlier that week. What a bitch! I needed to find me a sweet woman capable of matching my libido. My last lady was all about the lights off, missionary position sex, come to think about it I don't think I ever got a good look at her naked. Those are six months I guess I will never get back. As I sat alone in my bachelor apartment, clean for a guy, but still not the greatest place to bring a chick home to, I started feeling sorry for myself. I had a feeling it was goin... Continue»
Posted by Asmarani 4 months ago  |  Categories: Anal, Shemales  |  
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Weekend with my s****r - part 1

Continued from sunbathing with my s****r.

The week went so slowly, my mind always wandering back to our day together....stroking my cock endlessly replaying each and every kiss, touch and stroke. We stuck to our agreement of not talking about it when anyone else was in the house, not touching or staring was the hardest part, the sexual tension between us was incredible, I can't believe our parents didn't sense anything. We did leave bedroom and bathroom doors open just enough it was safe. Each morning when Jane left for work she'd leave some underwear on her bed for me.....twice it was e... Continue»
Posted by ukdan78 4 years ago  |  Categories: First Time, Shemales, Taboo  |  
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Car Bonnet Cockriding Whore

Hi Guys,




This true story dates back about 4 1/2 months now, and takes place outdoors, well over a car bonnet to be exact.


I had been chatting to this lovely guy called Dave, we had been chatting on a different site and arranged for him to come over from where he lived to where I live in Droitwich. Well I had been getting my self ready most of the evening showering, shaving my self totally smooth including my pussy, made a real effort to look hot with my makup and clothes. The usual things, stockings suspenders, 1/4 cup bra with matching thong, and high heels, a loose fitting top ... Continue»
Posted by donnamarie09 7 months ago  |  Categories: Anal, Shemales  |  
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Dominant Sex Therapy

I had to go see a sex ther****t because I was addicted to jerking off. Little did I know she had a surprise waiting for me when i got there. I sat down and she got right to the questions. "So how long have you been jacking off" She asked. I said "about 20 years now" She nodded her head and asked " Do you watch porn when you jerk off?" I said "Yeah every time" She said "Good. How many times a day do you jack off" I said "all depends sometimes once, If i get a really good scene I try to break my mind from cumming too fast so it can be, 4-5 times a day." She said "Wow that's a lot of masturbat... Continue»
Posted by michneo 28 days ago  |  Categories: Anal, Hardcore, Shemales  |  
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supermarket tranny

It was a typical Saturday morning. I was at the grocery
store doing my weekly food shopping. As I was perusing
through the vegetable section my eyes caught sight of a
a very attractive woman. She had long dark brown hair,
pretty face and a nice body.

I worked my way over to her and checked her left hand
for a wedding ring. She had none. I made some remarks
about the slim pickings the supermarket had. She and I
quickly engaged in conversation about cooking etc.

We walked around the store side by side picking our own
groceries an just having a good time. It was time to
c... Continue»
Posted by rickk1 1 month ago  |  Categories: Anal, First Time, Shemales  |  
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MY GAY PRISON SISSY ****


I'm sure many of you have seen a number of movies or television programs based on prison life behind bars. Having recently spent some 29 months in an undisclosed New England State Pen, I'll now share with you first hand, some of the wildest and most unbelievable sexual experiences one could ever imagine.

While still on parole now, I will change my name here and not mention the state facility involved. Other than to substitute a few names for some of the real ones involved, all of what I'm disclosing here actually happened between late July of 2007 and Dec. of 2009. My work... Continue»
Posted by cddixie 5 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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Deer Hunting with Daddy

Every year, a group of my f****y members, mostly uncles and male cousins, all pack up our gear and head into the mountains every fall for the yearly deer hunt. I had been going since I was 5. All the younger cousins slept inside an uncle's trailer, while the adult's and older cousins slept outside in a tent. This tent was huge and was intended to hold up to 10 people.

One year, when I was 8, I was having trouble sl**ping. I left the trailer and went to the "grownup" tent. As I got closer, I could hear strange noises...grunting and moaning noises ;-) I quietly unzipped the tent, but only en... Continue»
Posted by cdsexslut 2 years ago  |  Categories: Group Sex, Shemales, Taboo  |  
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mommy's new girl

It's true that I had become accustomed to drama in my f****y. My father was loud and mean, especially when he was d***k, which was most evenings and every weekend. He would back my poor mother into a corner of the kitchen and berate her, towering over her in that threatening way that I knew so well, telling her she was fat and ugly and stupid and spending too much money on me. He would get louder and louder until she finally began to tremble and sob – then he would storm out of the house in disgust, as if her crying gave him the right to leave his "silly emotional wife" and visit his drinking ... Continue»
Posted by momandboys 1 year ago  |  Categories: Fetish, Mature, Shemales  |  
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The heavy girl in the bar.

This is one of those stories from my past that I wouldn't consider rather astounding except for how it ends. It was a monday about 2 years ago. I was recently single and pretty horny so I figured my best bet aside from dating websites would be to go out to a bar and find a girl to hookup with. I hopped from bar to bar in town and everything was pretty empty with mostly men. I got to the last bar I would visit for the night, it was a bit more upscale than usual but there were a few women there. I flirted with them but they turned around at the bar and started ignoring me as if I didn't exist wh... Continue»
Posted by experiencedjojo 5 months ago  |  Categories: Fetish, First Time, Shemales  |  
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The special overnight bag

I did not want to have another boaring sales trip,so I packed up my special overnight bag for this trip. All the items a gurl would need to have a special trip. Inside were a few skirts some stockings and two wigs ( I can never decide)a few items so I could get clean and my laptop and camera.
After my sales meeting I went back to the hotel,took a long bath,cleaned myself and shaved everything smooth. Put on my make up ( this time I got my eyes perfect !) put on my stockings slinkey red skirt and this time I opted for the long black wig.

I felt so slutty walking down to the bar in the hotel... Continue»
Posted by sodeep2 1 year ago  |  Categories: Anal, Shemales  |  
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Becoming a Sissy Cocksucker (true story)

I always loved feminine things. I'd wear my s****rs panties as often as I could. I loved the way they felt, the soft fabric, the high cut legs, and especially the frilly lace edging! I graduated to bras and padding them and wondered what it'd be like to be a girl.

I always loved watching porn where a guy is sucked off by a
woman. I started to realize, what turned me on the most about it was watching his cock when it orgasmed! I LOVED watching the cum shoot out and on to her face and in her mouth! I used to watch it (and still do) dressed in panties. Well, fantasy eventually took over, I wo... Continue»
Posted by vickiebicd 7 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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My shemale mother!!!!!!!!

I know there is a similar story similar to these but be assured, the other story only served its purpose as a catalyst for this one. This is a pure fantasy, the top fantasy that has been lingering in my mind for several years..here it is....


I am 35 years old and had always been living with my mother, who is almost 50 since my father left us 20 years ago. I am not sure of the reasons but I do know that my mother is an average looking woman with nice looks and a not so fantastic body. Her pear shaped figure is a norm for any woman with Indian origin and what I do know best is her mammary g... Continue»
Posted by yarracuda 3 years ago  |  Categories: Fetish, Mature, Shemales  |  
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Leila Has a Big 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 drew1207 10 months ago  |  Categories: Fetish, Sex Humor, Shemales  |  
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The Day Lana Turned Me Into Her Daughter!

When I was much younger my neighbor, Lana, a divorcee, kept an eye on me while my folks went out of town. It was she whom formally introduced me to cross dressing and it was quite to my surprise. Back then I could actually pass for a woman due to my build. My hair was shoulder length and my body was small framed with feminine features.
I used to try on my mother's panties and clothes even though they were too big for me. Lana, on the other hand, had a great body. She was athletic and did not have a huge chest or big ass. She had great curves and was well defined. When my parents asked if ... Continue»
Posted by lovetopleaseu 1 year ago  |  Categories: Fetish, First Time, Shemales  |  
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Crossdressers First Time

I was in my mid 40's and divorced and living a great life. I ran my own successful business from home and lived in a large house in its own grounds at least 5 miles from my nearest neighbour.
Whilst I was single I had an active sex life having been lucky enough to know 3 ladies who were unattached and had no need for a long term relationships but were happy to meet up for sex or go away for a break all no strings attached. They all knew of each other and I was aware they saw other men or ladies if they wished.
Debi was 50 a successful lawyer and very dirty. Helen was 60 a retired busin... Continue»
Posted by maninnylons 3 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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My sexy wife has a secret

My wife, what can I say she is tall and leggy with thick, natural wavey orange red head with beautiful porceline skin and just enough freckles to tell you she is a ginger. Add to that smokey green eyes and thin sexy lips and you can see why people refer to her as Gorgeous Gwen.
From the time we started dating my friends all expressed their envy at me landing such a smoking hot piece of ass. She is a freelance writer for fashion magazines and on-line blogs so she is pretty dressed up where ever she goes.
I got home one Friday evening from an afternoon shift. I knew she was home because ... Continue»
Posted by triphammer73 11 months ago  |  Categories: Anal, Fetish, Shemales  |  
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My Parents Had Gone Away on Vacation

My parents had gone away on vacation for a week. I was thrilled!

On my own for a whole week, free to do whatever I liked. And truth be told, what I liked was being nude, as well as dressing in women’s clothes. The first day they were away, I began enjoying my newfound freedom.

I am very slight of build, feminine really. My body is hairless save for in my crotch.

After dinner, I decided I wanted to enjoy myself nude. I turned off all the bright lights in the house, and left on a few lights that were dim. All the blinds in the house were open. I stripped off all my clothes and walke... Continue»
Posted by ssup28 1 month ago  |  Categories: Shemales, Voyeur  |  
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Becoming the neighbourhood slut

The following is a fictional story but mixed up with some real experiences and a few of my actual desires :)



The first real days of spring were finally upon us. This was extra cool since I would be alone for a week or so. I took a few days off of work too, so I can spend the time dressing up at home and possibly try to find some real fun too.

When I got a few free days I always did the needed grocery shopping in the morning so I have the rest of the day completely free to dress up and stay dressed up. I usually went to a shop nearby, grab the needed stuff quickly and go home.

I di... Continue»
Posted by analhottie 2 months ago  |  Categories: Anal, Fetish, Shemales  |  
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Dinner with Brooke

Brooke texted me on my way home from work, “I’m making dinner, come down when you get home.” I replied back, “Sure, I’ll stop and get some beer.” “No bother,” she said, “I already grabbed some. Just you is all we need.” This was always nice to hear, and it was always nice to see Brooke. I felt so comfortable with her especially since the many last encounters. But I never think any more than what it is. Just dinner.
When I got home, I went upstairs, dropped my bag and headed down the front stairs to her apartment. Her door was cracked open a bit so I knocked, saying hello and opened the door.... Continue»
Posted by ahsleymills 14 days ago  |  Categories: Fetish, Lesbian Sex, Shemales  |  
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Sissy story

Date: Thu, 11 Aug 2011 16:42:22 -0700 (PDT)
From: Danny Smith <bobber1945@yahoo.com>
Subject: A Sissy Story Part 2

I got very excited writing the following story

I always considered myself straight. I was married and at 55 my k**s had
flown the coop. But over the last few years I began to fantasizing about
cocks and being submissive to a more masculine man. I was 6' tall fairly
trim at 175, but with a small 3.5inch cock. I never thought a lot about the
size of my cock until one evening while I was traveling I visit an adult
video arcade. When I entered one of the video booths, I s... Continue»
Posted by aimen72 1 year ago  |  Categories: Gay Male, Shemales  |  
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