Shemales Porn Stories
Page 6

First Trans experience

It was about 15 years ago and I thought to myself, Hmmmm I do love transexual porn, I mean I really love it! So I embarked on my search for a transexual that would rock my little world.

Adult Work, ALT and other sites skimmed though to find just the perfect Tgirl for my initiation, as I searched and watched videos, photo galleries along with reviews from fellow punters, I came across Joanna Jet, a fully fledged porn star whom, with long blonde hair, gorgeous body and a cock that simply stood head and shoulders above the rest, this is it, I thought! So without a second thought I booked a 2hr... Continue»
Posted by cardiff_paul 1 month ago  |  Categories: Anal, First Time, Shemales  |  

Poker Night Part 7

A continuation of my story. Parts 1-6 can be found on my profile page. Thank you and Enjoy!

Morning of Halloween Day was uneventful. Daddy prepared breakfast for the two of us and Mistress Claire had come by as well to join us. "Are you excited for tonight?" she asked. I said "Oh yes Mommy I can't wait to get candy!" She giggled a little and said I looked so cute and adorable and continued eating her breakfast. Daddy placed a couple pankcakes on my plate and then I noticed his rock hard cock was fully erect, he was stroking it with one hand and patting my head with the other. "Would my baby... Continue»
Posted by ConvertedGirl914 1 month ago  |  Categories: Group Sex, Shemales  |  
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Tranny Dogging Experience

Not my story as i'm a proper woman lol but i just loved reading this...................

I am a 24 year old male to female transsexual, I have been dressing up as a a woman since I was 14 and had nylon led sexual fun since my early teens. Often wanking myself whilst wearing a pair of sheer stockings. The result is that today I have a very large wardrobe of clothes and shoes, I am completely smooth all over apart from a landing strip and have manicured nails and shaped eyebrows and with killer legs in high heels. I am single but I had this strong desire to go dogging. I fantasized about being... Continue»
Posted by celtic-green 1 month ago  |  Categories: Fetish, Gay Male, Shemales  |  
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A story-tribute to Susie

This story is fiction. Some people like to do tribute photos, where they cum across a photo of someone’s face. This is a story tribute to Susie, aka soeager2, an xHamster user I really want to fuck.

I wasn’t sure what to expect when I got an e-mail about my boss needing to see me in his office later that afternoon. I hadn’t committed any real transgressions and I’m one of the more productive workers in the office, so I didn’t think I was going to be terminated. My mind wandered to anywhere but the job, until it was time for our meeting.

We exchanged some pleasantries and the... Continue»
Posted by 247hornyboi 1 month ago  |  Categories: Anal, Mature, Shemales  |  
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There Are No Limits, part one.

*This story is a work of short(ish) fiction, and despite the tribute that I would like to pay to the real people these are based off of, their names have been changed. Chicagoland area residents will recognize some of the places despite the name changes.*

Part 1:

Sheridan and I have been partners at the Wesley Avenue Police District for something like six years. We're part of a larger group of six: Me, Bonds, Martinez, Sheridan, Maurice (the only one who uses his first name) and Woodard. Officially, we're known as the patrolmen on the night shift in Lakeview, but the brass calls us the... Continue»
Posted by asphalt3 1 month ago  |  Categories: Anal, Shemales, Taboo  |  
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Koni & The Carpet Guys

Monday morning, my day off, and my wife just left for work. I just finished shaving my body and legs to a gay silky smoothness. Excitedly, I went to the closet in my den, pulled out my secret duffle bag and began to dress. Picking out red lacy thong panties, then the lazy red matching bra. The black fishnet stockings, which always made me so excited when I had them on; then the little black dress. I sat that neatly to the side and went upstairs to my wife's vanity cabinet. I sat and began to put on my makeup, concealer, eyeshadow, lipstick and blush, until I look so good I wanted to fuck mysel... Continue»
Posted by Konicum 1 month ago  |  Categories: Group Sex, Hardcore, Shemales  |  
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Tricked by a shemale

I was out with a couple of guys from work, Brian and Dave, and we were having some drinks at a local bar. I'd never been out with them before, but they invited me and I didn't want to be rude.

While we were having our drinks I had made some negative comments about gay men at one point, you know how it is, right? Just trying to make some conversation, but they hadn't said anything back, negative or positive, but they did exchange a look that I didn't think about until later... much later.

Brian ordered us another round and I excused myself to take a leak. All I remember after that was ... Continue»
Posted by kevinj631 1 month ago  |  Categories: BDSM, Gay Male, Shemales  |  
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Call me megan.

I was in high school, and i was about to go on the school trip to germany.
I was really excited to go and enjoy my week off, until i found out one previously unmentioned fact in the trip meeting, that we would be sharing rooms with two other boys.
I had recently started masturbating about guys, and was desperate to feel the thrill of giving another guy head, so desperate i had spent the last two weeks in my room every evening, sucking on the rounded back handle of a hairbrush whilst my dick grew harder and harder in my boxers, then sliding it into my tight teen ass and cumming over my toned ... Continue»
Posted by hardcoresissy 1 month ago  |  Categories: First Time, Gay Male, Shemales  |  
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The Ghetto bitch

-The Guys

4 ghetto guys was inside a porn site looking at random sissy babe pictures when they accidently found a picture of someone they know. Like every album they clicked it that specific one with a tranny dressed so girly with mouth open. The guys had such a stone hard erection by watching all the pictures, they even said "I Would bang that sissy pussy 4 sure!" and everybody agreed. It was that guy from elementary school named L****. They started to chat with him, pretending to be the perfect guy to take care of his sissy needs. After 2weeks they made this sissy want to meet eachother, ... Continue»
Posted by sissyVenessa 1 month ago  |  Categories: Shemales  |  
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My first time

This is a true account of my first time with another man.
Cruising the craigslist personals had become a common practice for me when I was bored or feeling horny. At first it was just reading ads until I got so turned on that I had to masturbate; but then it turned into actually replying to posts. Around the same time, I had become curious about wearing panties. One night when I was feeling especially horny, I tried on a pair of panties that a girl had left under my bed after a late night hook up. I fell in love with the feeling and began placing my own ads to chat with men that liked guys i... Continue»
Posted by igotoneforya 1 month ago  |  Categories: First Time, Gay Male, Shemales  |  
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A dirty Fantasy

Before I start this it would be in a perfect world with no d**gs and disease. This is one of my fantasies of being used just for others dirty pleasure.
I show up at the house dressed in normal clothes, thinking we are just getting together for a few beers or what ever. While we are sitting around, one of you hands me a pair of lace crotchless panties and tell me to go change into them. I do as i am told, and upon re-entering the room I see a bench set up in the middle of the room and the floor around it covered in plastic. I am asked to lay face down on the bench, and I do as I am told.
... Continue»
Posted by Lookingforkink 1 month ago  |  Categories: Fetish, Group Sex, Shemales  |  
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My First Translesbian Encounter

He came over sometime around 6 and wanted to change at my place; that was fine of course. I totally understood. I wouldn't want to risk anyone I know seeing me dressed all feminine. I've always been discreet. Jen and I met through craigslist and after a coupe weeks of emails we finally decided to meet at my place.
I honestly expected her to look a lot more feminine, but then again on her emails all I ever saw of her was her neck down dressed in lingerie. i did not expect some tall broad shouldered stocky guy with spikey hair to show up.
I'm not too into men, and although i would totally ha... Continue»
Posted by Tslizz 1 month ago  |  Categories: Anal, First Time, Shemales  |  
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First time with a tranny I met on grindr!

This is a true story. I am a straight acting 23 year old, 5ft 10 and an athletic 160 pounds.

To this point I've only ever been with one guy before in a wild, spur of the moment spring break fling but it had opened my eyes to a world I knew I wasn't finished with. I had joined the gay app grindr in search of a tranny to fulfill my fantasies and finally I found one!

Her profile read "looking for a submissive bottom to be my bitch" it was just what I wanted! I eagerly messaged her but began to get cold feet and when I started asking too many questions, she told me to "fuck off if you're go... Continue»
Posted by Datrap6 1 month ago  |  Categories: Anal, Hardcore, Shemales  |  
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Hotel Adventure

A few months ago, I started a new job. The job took me around the country, often to locations far from home, where I would stay in some easily forgettable hotels, which usually, at least, were blessed with free WiFi. I would generally arrive the night before attending client meetings the next day.

This gave me many opportunities to enjoy my old hobby of cross dressing. Now, I am straight, but - for as long as I can remember - have enjoyed the thrill of dressing as a woman. I have never gone out in public, and my wife has no idea, so it is a very private hobby, except that recently I have t... Continue»
Posted by mallenwc 1 month ago  |  Categories: Fetish, First Time, Shemales  |  
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Remember Me???

“Okay, folks! I think we can wrap it up and get back to work,” said the brand new manager of the Atakapa Regional Water Treatment Facility. “Angela,” the six-foot-two-inch dark-skinned man said, “what time do I have to meet the realtor?”

“You’re scheduled to meet her at the first house in twenty minutes, sir,” answered his new short and plump secretary.
“Alright then. I better get going.”
“Roger that, sir. I emailed you the location and a link on Google maps. Should take you right there.”
“Thanks. Back in a couple of hours.”

Joe Dowdell checked his iPhone 5S as he strode across the pa... Continue»
Posted by faggyboi 1 month ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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The Passage of Lydia Part 3

The tale continues ……
Aunty Bev led me into the bathroom and after stripping off her lingerie she ran a shower for us and we washed each other, taking time to lather up and explore each other’s bodies. Aunty Bev decided that all traces of hair were to be banished and set about shaving my pubic area and my bum, which I may add was a very pleasing experience.
After towelling ourselves Aunty Bev began rubbing me all over in a body lotion.
“This will help stop any shaving rashes and keep your skin feeling soft and smooth.” She added. I must say the whole sensation was delightful.
I sat at her... Continue»
Posted by fifebi 2 months ago  |  Categories: Fetish, First Time, Shemales  |  
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Pink Short Shorts

For Miniskirt-boy

It's a lazy Wednesday getting close to noon and I'm still lying in bed when Sammy walks in. She's cold. Summer has been pretty underwhelming this year to say the least. The sky is as dirty as the gutter and overflowing, rain hammering the windows.

'Hey,' I smile invitingly and she sees just beneath the covers that I'm still naked too. 'What are you doing?'

'I just came for my knee high socks, my feet are cold,' says Sammy, parading her ass and lean legs in those pink short shorts of hers. On top she's wearing a white pyjama top with pink polkadots, her... Continue»
Posted by dantheman1980 2 months ago  |  Categories: Anal, Shemales  |  
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Something different ....part 3

I looked in the mirror as the curtains behind me opened, my hands went to cover up the growing bulge in the dress i was wearing as i stared at the reflection of the woman who now stood behind me. Just been sorting through the racks and thought that this might suit you she said as she held out her hand towards me which held a corset. I turned a little making sure that my front was facing away from her conscious still of my bulge. I thanked her and took the corset from her and told her that it looked a little bit on the small size. She laughed and replied that it was a lace up corset so that th... Continue»
Posted by oldognewtrix 2 months ago  |  Categories: Fetish, Mature, Shemales  |  

Good ‘sheboiz’ shouldn’t be allo

This is the problem with sissies not locked in chastity. They love the girly clothes - mincing around in high heels and frilly dresses. They love the way they feel an look. It turns them on beyond belief. But most of all they live the way their useless appendages feel through the sheer nylon of their pantyhose or the soft, smooth satin of their panties. They can’t help themselves. Sissies ate generally lifelong, compulsive masturbators. Inevitably this will happen. Cum all over its pantyhose and But most of all they live the way their useless appendages feel through the sheer nylon of their pa... Continue»
Posted by klaramolka 2 months ago  |  Categories: Fetish, Gay Male, Shemales  |  

The Passage of Lydia Part 2

Let me continue my tale ……..

I sat in front of the mirror and saw my pale face as a blank canvas but the array of lip sticks, foundation, eye shadow etc. filled me with dread, I’d watch my mum getting ready and the way her hands would wave our her face and then presto she was all glammed up.
I have to admit it was a disaster and my attempts made me look as if I had been beaten up. Dismayed I thought I would checkout the hat boxes on top of the wardrobe. Eureka! I giggled like a little girl when I found no hats but 6 wigs, and by the soft feel they were good ones. I was drawn to the shoulde... Continue»
Posted by fifebi 2 months ago  |  Categories: Fetish, First Time, Shemales  |  
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