Shemales Porn Stories
Page 63

Never Going Back Again

feminize – feminization – transsexual – crossdresser – gay

To tell the truth, I never really figured out how to do the guy thing very well. I was always small for my age. People used to say that I'd shoot up someday, but it never happened. All through my school years, I looked about two years younger than my classmates. It didn't make for an adolescence filled with confidence, or even security. I was picked on mercilessly—teased, of course, but also actually beaten up from time to time.

It didn't help that I wasn't just small of stature but also small in the "manhood department"—s... Continue»
Posted by naughty_bi_interest 1 month ago  |  Categories: Fetish, Gay Male, Shemales  |  
2009
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91%
  |  5

Sexy show

One night I was at a friends house with a few people playing cards. The whole time watching my friends wife sit in front of me in little shorts and a shirt that showed her big tits when she bent over. I was so horny that I snuck in her room and went thru her drawers so I could grab some panties and a couple bras. I found a sexy leotard swimsuit, pantyhose, tight sheer shorts, and a skirt. I went to the bathroom and put it all on under my clothes then I left. I was so turned on in her clothes that I took my clothes off and I wore her white bra, a hot pair of her thong panties and put on her p... Continue»
Posted by droger709 3 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  
2008
  |  
61%
  |  2

A used sissy

“This one right here” Bob said. “This little sissy is perfect!” Bob and his two friends had spent the last few weeks scouring Craigslist personal ads for a small transvestite that they could take advantage of. “I’ll email the cunt with a pic of my nine inch cock – see if she bites!” Bob said. Sure enough a day later, the TV named Debi contacted Bob with pictures of “her” own. Bob shared the pics with his friends. “Look!” Bob said, “The cunt could pass easily, and the sissy even has little sissy boobs! Oh, this is gonna be fun! ” They all agreed that Debi was to be the one.
Debi had said in... Continue»
Posted by tvdebi 1 year ago  |  Categories: Shemales  |  
2008
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100%
  |  8

Long Distance Cr*!gslist Charity

Through the stresses and demands of everyday life, I had found myself becoming evermore restless being alone after loosing Frank. It was coming up the five year anniversary since he passed. I had been looking on Cr*!gslist infrequently in search for a possible new partner. Often find men who are married seeking a play toy on the side, or those who want a gurl with a dick to suck, and bend over for. While in the world of alternative love, passion comes in far more than 32 flavors- that's not what I'm seeking. After realizing that the local ads are little more that the same handful of horn... Continue»
Posted by gurlinpumps 1 year ago  |  Categories: Anal, Shemales, Taboo  |  
2007
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92%
  |  5

Drama queen part two

Please read Drama Queen part one before starting this story

Drama Queen Part two.

About 2 pm on Thursday I heard the door bell, looking through the spy hole there stood Amy again fully dressed and made up. I let her in and took her coat. As I hung it up for her I felt her hands creep up under my skirt and round to the front of my panties and caress my penis.
“Steady darling” I said “You’ll have me ejaculate in my panties instead of your mouth”.
“What have you got that is poking into me, it’s very hard”. I added.
“Just a little something I hope you will enjoy”. Amy answered
“If it’s w... Continue»
Posted by hottvcarole 1 year ago  |  Categories: Shemales  |  
2007
  |  
100%
  |  3

f***ed to be Female Pt2

Back in my room I lay on the bed trying to come to terms with the fact that I was being f***ed to become a woman. I kept looking at where my testicles had been, trying to see what they had done to me.
My penis had been pulled back into the space where my testicles had been and then they had stitched it flat. I soon found that I had to sit in order to go to the toilet.
I felt my face and arms. They were so smooth and free of hair. My chest was bare and smooth too and I looked at my nipples for any tell tale signs that might suggest that I was growing breasts. My nipples felt sensitive and I c... Continue»
Posted by PaRiaH236 21 days ago  |  Categories: BDSM, Shemales, Taboo  |  
2007
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100%
  |  1

My First Time with a Transexual

I was in a large city about 100 miles from my home for a week on business. I had been hitting the bars for a few days with out a lot of luck. On the way back to my hotel afer work one day I picked up a few of the alternative newspapers/sex ads. Checking the ads out later I saw women, men and transexuals all offering there services. I saw one picture of a beautiful blond and was blown away to see that the ad was for a transexual. I called and made arrangments for her to come to my hotel in a few hours. I busied myself shaving a showering for when she would arive, putting on a pair of gym shorts... Continue»
Posted by Bob111401 5 years ago  |  Categories: Anal, Shemales  |  
2006
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100%
  |  11

My night of first times!!!

I was sitting in the bar with my friends when she walked in. Black short dress, low cut neckline. I can see the garter straps holding her stockings. I think that is what caught my attention first. I had seen garters and stockings in movies but never in real life and her legs looked great. I couldn't keep my eye off her all night. I had to seem like a stalker with my eye's, I wasn't paying much attention to the conversation at the table with my friends she was lust at first sight. I had to make a restroom trip and when I walked out she was standing there. My heart skipped a beat and my stomach ... Continue»
Posted by Trudru 5 years ago  |  Categories: Shemales  |  
2006
  |  
94%
  |  6

I've dumped my boyfriend. Now he wants cock..

Me and Marc had been going out for 7 months. He's nothing that special to the eyes but he has a way with words. He could put a simple sentenced together and get any girl, any age, with any genitals?
I thought it was only a rumor going around that he was Bi-sexual so i ignored it completely because he was great in bed.

Tall strapping lad about 6'3", toned body, tanned skin and semi long hair about ear length. Long enough to twirl in your fingers while he's pushing himself into you.


After 7 months, he kinda gets boring. Like he lost interest in me and i lost interest in him. I actually ... Continue»
Posted by sophie101 5 years ago  |  Categories: Anal, Gay Male, Shemales  |  
2003
  |  
97%
  |  8

Luci........... My first.


LUCI


I only went into the bar on that stormy winters night because I was drenched, and I had to get out of the rain.
As I walked in a soft dark voice beside me said “Oh you're wet, you should get out of those clothes.” I turned and saw a lovely lady sitting at a corner table near the door.
Well I'm not the ugliest bloke in the world, but it's the first time an absolutely gorgeous woman has told me to take my clothes off as an opening line!
I told her I was very flattered by her invitation. I saw she was alone so I asked if I could buy her a drink?
She said “That would be nice.” So I... Continue»
Posted by cockhappy 4 years ago  |  Categories: First Time, Gay Male, Shemales  |  
2003
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99%
  |  5

PF's Black Romp and JoyceLynn's Awakenin

PF's Black Romp and JoyceLynn's Awakening

To start with you can see my profile at http://profiles.yahoo.com/joycelynntv1 which also has some phoito albums and my primary email address. I have a 360 page at http://360.yahoo.com.JoyceLynnTV1.

When my wife and I first met, our sex life was fantastic! She was a very sexual lady and always made herself available. She usually wore stockings and garter belt or thigh highs, high heel sandals, and something that was sexy and suggestive. We made love and had sex in every room of the house, including the kitchen while she was making dinner. Once I ... Continue»
Posted by JoyceLynnTV 4 years ago  |  Categories: Interracial Sex, Mature, Shemales  |  
2003
  |  
95%
  |  26

My first sex

I left home when I started college and had to take a part-time job delivering advertising leaflets in order to pay my way.

I had been doing the job for a couple of weeks when one houseowner, mowing his front lawn, asked me if I would like to do some Saturday gardening. He named the wage and I readily agreed.

I started that Saturday and after a couple of hours Tom called me into the house where cakes and soft drinks were waiting. He said he had an appointment and he left his wife Terri to keep me company.
Terri was a tall, graceful brunette with 48-inch doubleD breats that looked as if... Continue»
Posted by Dav10 3 years ago  |  Categories: First Time, Group Sex, Shemales  |  
1998
  |  
92%
  |  3

Party Favor(s)

My getting into Blue Mountain State U., in the early 1970's was a blessing in so many ways. For one thing it got me out of a bad living environment in my little "Hick Town". I got accepted on a Music scholarship, not Football or Basketball, like most Black students there at the time, so I had to make the most of it. Back then no one asked bout sexual orientation, but since I managed to become the Drum Major for our high school band it was assumed, that I was "lite in the loafers", for some reason. It just happened to be true, but like so many back then I buried it deep and tried to no... Continue»
Posted by Keith_Walters 2 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
1995
  |  
100%
  |  5

A Date


Dad sat across from me at the table and shoveled oatmeal into his mouth more out of habit than for nourishment. Dark circles under his blue eyes confessed a lack of sl**p. His constant sad expression made him look older than his forty-seven years. It didn't help that his hair had rescinded back to his ears. Worry had thinned his once bulky frame. He had been in a declining emotional state since my mother had left us last spring.

The day after I graduated high school my mother packed her suitcases and ... Continue»
Posted by Batman_112 24 days ago  |  Categories: Taboo, Shemales  |  
2002
  |  
91%
  |  1

Tranny Gas Station Attendant

This happened about ten years ago and I thought I'd share it with you all for your enjoyment and mine! Like I've said before, although I'm bi-sexual, I don't walk around checking out other guys, nor do I like to be intimate with one. Sure, some might consider taking a cock in the mouth or ass intimate, but I consider it just sex. When I say I'm not intimate with other guys, I mean I don't kiss or cuddle or anything like that. It's always just sex, with no strings attached.......usually! There are exceptions to any rule, and this experience is one of them!

... Continue»
Posted by panteeluvr 5 years ago  |  Categories: Shemales  |  
1992
  |  
98%
  |  16

My first time with a TS woman, the next morning

After sucking my new ts girlfriend and holding her close on the couch, we spent the night sl**ping together.

I woke with her in my arms. We were sl**ping on our sides and face to face. Her body felt so nice and warm against mine. Then I noticed that she was hard. Her cock was hard and hot and pressed against my cock.

I reached down between our legs and started to stroke her hard cock. Soon she woke in my arms and kissed me while I stroked her. She enjoyed my attention for a while then suddenly she jumped out of the bed and grabbed my hand. She pulled me to the bathroom and into the showe... Continue»
Posted by tsLove888 3 years ago  |  Categories: Anal, First Time, Shemales  |  
1991
  |  
21%
  |  8

Confessions of a first time dogger

I’d been dressing for some years at home before one day, I dared step outside climb into my car and go for a drive. I was dressed in my school girl outfit which was quite daring considering this was my first public appearance. I headed straight for a local dogging spot I knew. An old stretch of road that is now only used as a cut through for the odd bit of thru traffic. I drove slowly up and down passing a few parked cars and vans whilst cautiously looking at the drivers to see if they were looking. After a short while a guy who was parked up smiled at me. I drove back passed him once again to... Continue»
Posted by mirandacarlton 2 years ago  |  Categories: Anal, First Time, Shemales  |  
1990
  |  
100%
  |  6

How I developed a crush for transvestites

How I developed a crush for transvestites


I am a 33 years old woman who loves sex very much. My name is Desirè. With my boyfriend Errol we have a very happy and open relationship. Since I am also a bisexual from time to time we make love with another woman. We also had group sex a few times.

Last week I left home to go to my girl friend Natalie's summer place to have a threesome with her husband. Just when I was approaching the suburbs I noticed that I forgot my cellular phone. Since it was early enough I returned home.Errol had told me that he would go fishing. When I ent... Continue»
Posted by CDDilekGul 6 years ago  |  Categories: Shemales  |  
1988
  |  
17%
  |  8

Old Black Carl (part 1)

Old Black Carl (part 1)

This is a true story that took place just as I graduated from High School.
I grew up in a small town, and there wasn't a lot of diversity. I had a very thin, smooth body, and long flowing hair that went halfway to my ass. In those days, I thought I looked like a rock star, and so did the girls. I did pretty well. I met a lot of girls from a town about 20 miles away, and I didn't have a car. But back then you could count on getting a ride if you hitchhiked, and I did so to hang out with the girls, often. And that’s how it all started.
I was dressed in a pair of jea... Continue»
Posted by cocksucker4bbc 2 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
1988
  |  
100%
  |  8

I Could Really Use Some Extra Money (Part 1)

Boy, I could really use some extra money, I was thinking as I walked over to George’s for a Saturday visit. Maybe George would have some ideas.

I arrived at George’s house. He greeted me once I was in the house with a kiss while he squeezed my ass cheeks. I loved the way he touched me.

I’d known George for two years, since I’d started mowing his lawn.

I lived with my Mom. She was a d***k and paid me no mind; I might as well have been living alone.

But George had taken a keen interest in me from the beginning.

We got some coffee and sat down to chat. After awhile, I brought up ... Continue»
Posted by ssup28 1 year ago  |  Categories: Shemales  |  
1988
  |  
100%
  |  6