Shemales Porn Stories
Page 65

Daddy's Little Sissy Cock Sleeve.

I stirred as I felt my bed suddenly shift with the weight of someone crawling up from the end and between my legs. I’d slept so peacefully, as I do every night when my Daddy Dom locks my wrists and ankles to the corners of my bed in leather lined steel resrraints, face down, with my little sissy pussy filled with his cock. He fucks me to sl**p, and keeps me covered like a security blanket till I’m soundly dozing, then he slides out of me and fastens the translucent pink plastic panties around my waist. He doesn’t bother with diapers… he used to, but he says he likes the way it looks when his c... Continue»
Posted by AniGirl81 9 months ago  |  Categories: Anal, BDSM, Shemales  |  
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Dream Date. Part 1

Part 1 Dream Date.....

Sitting along in a booth enjoying 18 yr old scotch, when I hear the clicking a high heels against the wooden floor. All the men and some of the women turn and take you in. You are absolutely one of the hottest women I have ever seen. Wearing a short blue demon skirt white top and very super sexy red heels, but it's not what you are wearing, it's your smooth sexy long legs that has my attention. I can see the envy in all the men's eyes. I ask you to sit and you ask if I've been waiting long, in which I reply you are well worth the wait.
This ... Continue»
Posted by pleasetv 9 months ago  |  Categories: Anal, First Time, Shemales  |  
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Fucking my first tranny - Fun times with Jennifer

This happened about a month ago, it was one of those days where I felt really horny so I had to do something about it and I just didn't want to fuck a woman this time. I've been really curious about trannies for a while now, I once fucked a friend of mine when were fooling around (I should write a story about him too!), but the combination of tits, smooth ass and a cock would always catch my interest and would get me really aroused every single time I thought about having sex with one.

A little backstory to this before we go any further...

Through this bullshit dating site I came across... Continue»
Posted by Sylf 9 months ago  |  Categories: Anal, First Time, Shemales  |  
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My Dirty imagination ;-) Chapter 1

I arrived on the doorstep of a huge house, feeling a little intimidated and small in comparison. As I knocked on the brass door a few seconds later a woman appeared at the door, mid 40s, tall, brown ei black hair in a pencil skirt and a shirt. With heels on as well she looked rather intimidating but smiled and said “oh you’re his present” I half smiled and nodded not knowing what to say. She invited me in, fixed me a drink of cider saying “its what all the young boys love isn’t it” and led me down into the cellar. She then told me she was going to get me ready, she asked me to strip from my bo... Continue»
Posted by CathyxXx142 9 months ago  |  Categories: Anal, First Time, Shemales  |  
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A Super Panty Daddy Fantasy -- PART ONE

*From time to time I get so horny that I start looking for partners on CL. It has been years since I've managed to actually physically connect with someone that I found on there. This story is a fantasy of a scenario that I'd be very interested in playing out. Hope you enjoy.*

Scanning down the page on Craigslist, I was looking for ads for m4m, t4m, m4t, t4t, and especially mw4m / mw4t. I found a mw4t ad that instantly hardened my pantied dick. The sheer fabric stretched as I kept slowly teasing the underside of my cockhead through it.

"Looking for masculine panty daddy.

We are a... Continue»
Posted by cumquarts 9 months ago  |  Categories: Fetish, Group Sex, Shemales  |  
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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 9 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 9 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 9 months ago  |  Categories: Fetish, Mature, Shemales  |  
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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 9 months ago  |  Categories: Fetish, Gay Male, 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 9 months 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 9 months ago  |  Categories: Anal, Interracial Sex, 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 9 months ago  |  Categories: Fetish, 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 9 months ago  |  Categories: Anal, Hardcore, 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 9 months ago  |  Categories: Anal, First Time, 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 9 months ago  |  Categories: Fetish, Group Sex, 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 9 months ago  |  Categories: First Time, Gay Male, 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 9 months ago  |  Categories: BDSM, Gay Male, 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 9 months ago  |  Categories: Anal, Shemales, Taboo  |  
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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 9 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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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 9 months ago  |  Categories: Group Sex, Shemales  |  
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