Shemales Porn Stories
Page 63

Met 2 s****rs with a secret part 2

Synopsis: This story is about a young man named Devon who is living abroad as he goes to college. In the previous installment, Devon meets Asha and Shanthi - two half-white, half-Sri Lankan s****rs who live in the apartment next to his, and they begin an immediate friendship. With Asha, that friendship becomes more after Devon discovers that she is a transsexual. After their first night of passionate sex, Asha tells Devon that they must keep their relationship a secret because her s****r Shanthi is in love with him, and Asha fears she has already betrayed her s****r by sl**ping with him. But D... Continue»
Posted by drew1207 1 year ago  |  Categories: Anal, Fetish, Shemales  |  
2025
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double date fun

It was just normal saturday when the phone rang.I answered it an my mom was on other end.She said can I ask you to do favor for me? I depends on what it is.Well she said, you know Cathy (moms lez lover) she called me and ask me to go out on date tonite.I yea so go, she said want to but her son just moved back in with her.I said yea don't he know about you two?Yes he does but we were wondering if you go out with him with us.I said well let me think,she said he very tall handsome an 46 yrs old.I said but does he know I am fulltime crossdresser? Mom paused a minute and said yes he does.I said ok... Continue»
Posted by cdpaula 4 years ago  |  Categories: Mature, Shemales, Taboo  |  
2022
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95%
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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  |  
2024
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100%
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Gary's Dressup Sissy

When I was a teenager I lived next door to a guy named Gary. We were friends for years but drifted apart as he was 3 or 4 years older than me, so when he discovered girls I didn’t see him for a while. However, one summer he and his then girlfriend had a fight, so being at a loose end he would invite me over to watch movies and play video games.

One day we were watching a movie, when Gary suggested watching some of his dad’s pornos. I eagerly said yes. So for a few days we would watch porno from about 10 am till 4 pm when his mom came home. His dad seemed to have hundreds of movies. One mov... Continue»
Posted by palmorr 1 year ago  |  Categories: Anal, First Time, Shemales  |  
2021
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100%
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Becoming the girl i really am....

I guess I'll start from the beginning, I was in my early teens and my parents had friends in town who we did everything with, travelling, camping, holidays, the works. They had a daughter who was a couple years older, and a son who was my age who was pretty much my best friend.

We started masturbating together in our very early teens, and since we were such good friends we were together a lot. One night i was sl**ping ove rhis house and while we were masturbating he asked "have you ever gotten a blow job?" "No" i said, giggling nervously as he slid right up against me in bedand slowly r... Continue»
Posted by dirtygurl4u 5 years ago  |  Categories: First Time, Shemales  |  
2020
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91%
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Crossdresser drinks cum

Nikki looked up at me with her big, brown eyes as her head bobbed on my cock. Nothing was quite so sweet as one of her blow jobs. She had this way of dragging her tongue along the underside of my cock that made me want to cum in seconds. I always tried to hold it, but Nikki wouldn't let me. When she wanted me to pop, she'd plunge her head all the way down my pole.

Less than three minutes into the BJ, my cock disappeared into her face. I shot my load. Nikki froze while I unloaded. She couldn't say a word, but the bemused look in her eyes told me she was loving every second of it. I must've d... Continue»
Posted by MasterDavidsslut 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  
2020
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98%
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My New Lover!

I was still testing the waters a bit. I went out in my skinny jeans and just a t-shirt (I still don't crossdress in public at least not heavily, still uncomfortable), my slightly long hair makes me look very androgynous. I wear very subtle eye makeup as well, I am happy in my body, it suits being a guy for my job and a girl for my lover. I thought I liked him a little but by the time we made it back to my house, which was empty, an irregular occurrence, he had been very nice and hit on me a little. He complimented my body and my ass (not to stroke my ego but I love my ass, I get compliments on... Continue»
Posted by bisubtaylor92 10 months ago  |  Categories: Anal, Gay Male, Shemales  |  
2018
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89%
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Settling in with my new RoommateHe

It didn't take very long for my roommate, Ed, to figure out that I was a submissive sissy slut. I think that Ed was basically a straight guy as far as his sexual orientation went but he liked the fact that, if he couldn't score away from home, a willing mouth and ass was always at home when he wanted it. Ed insisted that I wear at least a garter belt and stockings to bed every night. He said that he liked the way the garter belt "framed my ass" and he liked the way my stockings felt when I would wrap my legs around his waist. So, I would go to sl**p in my bed dressed in sexy lingerie and s... Continue»
Posted by rikki50 3 years ago  |  Categories: Gay Male, Shemales  |  
2014
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100%

He Got Used and Didn't Mind. (Part 1)

I am getting back into the habit of writing stories. As I have done in the past physical features of characters are left to the imagionation. Please comment on this if you like to let me know when I need to write part 2.

Dave met Jesse online and they kicked it off well due to things they have in common. Since they lived in the same city they decided to meet in person at Jesse's place. Dave had been working side jobs and told his wife Lucy that his new friend Jesse wanted to talk out some jobs he may have available, and off he went.

Once there a conversation took place about common inte... Continue»
Posted by mrman1982 2 years ago  |  Categories: Sex Humor, Voyeur, Shemales  |  
2013
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100%
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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 2 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
2009
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91%
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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
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61%
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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  |  
2008
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92%
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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%
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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  |  
2004
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97%
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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  |  
2003
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94%
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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%
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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  |  
2004
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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 1 month ago  |  Categories: BDSM, Shemales, Taboo  |  
2002
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100%
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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
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95%
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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 4 years ago  |  Categories: First Time, Group Sex, Shemales  |  
1998
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92%
  |  3