Shemales Porn Stories
Page 4

My Hotel Meet x

So after a year of being a secret sissy crossdresser and modelling my look on a good femal friend of mine I finally got the courage to meet for the first time. It was with a older man as it was less likely that there would be a chance of me knowing the person so would be safe not getting caught out.

I decided to meet at a local hotel that had rooms in a separate block like American Motels. I checked in to my room shaved myself and applied my makeup and got dressed in my black lace bra, panties and stocking and suspenders. I then put on a lace panel bodycon dress which was real tight around... Continue»
Posted by lingeriechick 1 month ago  |  Categories: First Time, Shemales  |  
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Alex and I. from friend to lover

The year was 1996, I was 36 yrs old, I was newly divorced and living on my own in a nice suburban apartment. Had been dressing for a few years and playing on the weekends, when time allowed. My preference at that time was for other gurls, but would not reject a nice gentleman if I found him attractive and appealing. But, I’m getting ahead of myself here. With the chat rooms geared toward the cd/tv scene plentiful, finding partners for a fun time was not hard at all. I was working 50 to 60 hours a week, so playtime during the week was nearly impossible.

I worked as a truck driver during the... Continue»
Posted by LisaTn 1 month ago  |  Categories: Anal, First Time, Shemales  |  
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Unexpected pleasure

Was out the other day running some errands and picking up a few things from a local super store near me. I had a bit of time to kill before I had to be somewhere later in the day, so after I picked up the things that I needed I went to this cute little boutique and second hand store hoping to find a few nice things that would fit my fancy. While just roaming the isle I noticed this young man about have my age crouched down looking at some very sexy lingerie and women's clothes. My curiosity got the best of me so I wandered over to his direction and noticed that he was very cute and was wearing... Continue»
Posted by btbwild 1 month ago  |  Categories: Gay Male, Shemales, Voyeur  |  
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Dear Diary - At the Hop

Cousin Marlene (have mentioned her a few times before in my post) calls telling me they will be having a retro style dance on Saturday night at the dive in movies that is located a few towns from us. I was not old enough to drive as of yet and she wanted me to go with her. Of course I said.
For the next few days (if I my teacher did not need me) she picked me up from school and we went to thrift and second hands stores looking for retro style outfits. I found a cute pink "poodle skirt and pink sweater" she found a yellow retro prom dress.
she came over to pick me up on on Saturday and she ... Continue»
Posted by MichelleSissy14 1 month ago  |  Categories: Hardcore, Shemales, Taboo  |  
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First time stallion continued – A Black stallion

First time stallion continued – A Black stallion

So it’s 22:30 and only around 15 minutes after the sharp exit of my Italian stallion. There I am still in the dark with the light of the bathroom seeping out of the small gap in the door and the flickering light of the T.V flashing occasionally over my silky smooth black stockings as I sit on the edge of the double bed facing towards the bedroom door, playing a little with the stretchiness of my black lace twisted knickers id left around my ankles as I was running through what I’d just been involved in.

As I think about calling it a night ... Continue»
Posted by dirtyjenna 1 month ago  |  Categories: Anal, First Time, Shemales  |  
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My Sexual Odyssey Part VII: Turning Tricks

A continuation of the journey described in part 6:

The next day I went to work as usual, but skipped my noon time ‘date’ with Brad. When I got home, I called Cindy and confirmed the party invitation. Then I called Tracy and asked if she could use me at the club.
“Of course! Are you k**ding? Anytime!”
“Well great, what time should I come by?”
“How early can you make it? We open at nine, as you know, but although nothing much happens until close to midnight, there is always a lot of action for the girls.”
“Well, I could be there by ten or so; is that okay?”
“That’s just fine. I’m sure I... Continue»
Posted by LeicaCD 1 month ago  |  Categories: Shemales  |  
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Sex Interview: Part Two

This is the continuation of The Sex Interview: Part one. More detailed questions and sexier with fantasies and different kinks. Enjoy! Here is the interview:
BD: This is your second interview. Some things have changed in your life. Your breasts have grown, very noticeable, and you have done some more things in which your audience needs to know. When we last checked you were a 46B, where are you now?
Alia: Now, I am at a 52C cup. Got a little bigger. I got to stop sitting down sucking dick. (laughing)
BD: (laughing) Interesting reason on why you think your chest is growing. You ar... Continue»
Posted by bigcheeks4u 1 month ago  |  Categories: Gay Male, Shemales  |  


The plumber was nothing to look at short kind of fat ugly hair on his lip and he smelled like Ben-gay but his helper on the other hand was an a dream come true tall blond muscular with deep blue eyes I couldn't keep my eyes from straying to his crotch where a telltale bulge was visible...I knew the plumber thought I was a real woman but his helper kept stealing looks at me I suspected he was on to me even though I look totally hot as a woman and most times they can't tell some guys just know...he didn't look turned off if he did so who cares right...I showed them where the leak was it was comi... Continue»
Posted by laceysgirl 1 month ago  |  Categories: Anal, Shemales  |  
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First time stallion

So there I am analysing myself in front of my hotel room mirror for a final check that I’m ready to greet my man when he knocks on my room door. Hair, brown shoulder length combed straight , check, Full makeup bronzer, blusher, foundation, mascara, eye liner and of course pretty pink lipstick all in check and a flutter of my false eye lashes for good measure . Perfect, one final pose for sassiness in my leopard print mini club dress being stretched at the breasts to accommodate my 34DD silicone bra infills. The bottom of my dress stopping just shy of the top of my super smooth silky black self... Continue»
Posted by dirtyjenna 1 month ago  |  Categories: Anal, First Time, Shemales  |  
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First time anal with a huge Dom cock (real story)

I was at home alone feeling really horny, I hadn't cum for about 1 week... I started watching porn and soon after I found myself on a dating website that I used to go on at the time...I was cross dressing occasionaly wearing stockings and knickers and I loved it. I had only sucked cock twice and now I needed more...
That night I started talking to someone who was crossdressing also, we chatted for ages and the conversation was getting more and more horny. He was looking to meet the day after, I was anxious about the whole thing but I was so horny that I was ready for everything...At some poin... Continue»
Posted by lidacd1 1 month ago  |  Categories: First Time, Gay Male, Shemales  |  
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sissy rules

sissy rules to live by

Rule#1: A sissy does not have a cock. A sissy has a clitty
Rule#2: A sissy wears a bra and panties
Rule#3: A sissy loves cock
Rule#4: A sissy loves cum
Rule#5: A sissy takes it in the ass
Rule#6: A sissy loves pink
Rule#7: A sissy loves her toys
Rule#8: A sissy dresses like a slut
Rule#9: A sissy shares
Rule#10: Sissies love facials
Rule#11: A sissy must have a tight ass
Rule#12: A sissy must have perfect bimbo makeup
Rule#13: A sissy grows big fake tits
Rule#14: A sissy is a pro cock suck... Continue»
Posted by bigsissy 1 month ago  |  Categories: BDSM, Shemales  |  
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My first time with a shemale

My First Time
2009, I was stationed in Camp Pendleton, CA at the time, just back from having been in Iraq and Kuwait for the previous 9 months. I had been looking at transsexual porn for a couple years at this point, having stumbled upon it somehow almost by accident. Still don’t know exactly how it got on my computer in the first place; probably one of the many hard drive contents exchanges that happened while deployed. Either way, moving along, when I returned, I began thinking more and more about the idea of a beautiful woman with an amazing, thick cock just pounding the absolute shit out ... Continue»
Posted by izach00 1 month ago  |  Categories: Anal, First Time, Shemales  |  
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Shemale Amazon Goddess

This story is based on a dream I had about shemale porn star Meghan Chevalier around 15 years ago.

I'm sitting up in bed. There is an empty glass on the nightstand; I know that I have recently d***k whatever was in the glass. I'm wearing a light violet silk robe, and nothing else. It seems quite feminine. Then I realize that my body has become quite feminine as well. The fat I've been carrying around for years is gone and my waist has tapered down to about 27 inches. My legs are long and slim. My hips are now softly curved with an ass that is far more female than male. My hair is now... Continue»
Posted by Entrapped 1 month ago  |  Categories: Celebrities, Fetish, Shemales  |  
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Misadventures of Karen

Wrote this for someone. Might be a small series, i dunno.

Late in the Winter evening, Karen sat down at her computer searching through her email with a glass of wine as she did almost every night after a long day of work at the office. Strolling through her emails Karen noticed a peculiar one from a coworker titled "Busted!". Karen was curious and opened the email to find picture after picture of her dressed up in super revealing women's clothes and exposing her ass for the world to see. Normally this would be no problem, but you see Karen, the protaganist of this peculiar tale, was born ... Continue»
Posted by ConvertedGirl914 1 month ago  |  Categories: Shemales  |  


All characters are over 18

Béa was sexy femboy when she found a wild runaway boy. She raised him and together raised their feminine side to grow up as s****rs into beautiful transvestites girls. Discovering each others body and transforming together they soon became lovers, living perfect girl life together until zombies attack the city. The girls discovered that people could be cured by having sex. Girls were on their way to inform the news star announcer Jim J.J Johns that zombies can be saved when Lilly was turned into zombie and had sex with a zombie girl that delivered a weird tentacle... Continue»
Posted by Baachan 1 month ago  |  Categories: Anal, Group Sex, Shemales  |  
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The Ultimate Humiliation and Entrapment of a Sissy

In the dingy motel room where my life turned around in such a short time is where this story begins but the beginnings of this story were many years in the past, a past in which dressing up, spanking, bondage, cocksucking, public outings and humiliation had occurred in bits and pieces. I was not so much a real submissive as much as someone who felt like it was edgy to see how far I could come to the precipice of my fantasies that aroused me so much without becoming trapped by them. In the end I hoped I would become trapped and feel all that goes with being stuck living such unusual fantasies... Continue»
Posted by dorisTVmaid 1 month ago  |  Categories: BDSM, Fetish, Shemales  |  
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Indian sissy maid: Wife Returns

the night while pressing aunty feet, she told me how girly i become, she wished she could have Wife like me. She told that village life is harder ,as she has to woke up early ,do all the house ,dairy and farm work, she get little sl** time ,she planned to take her with me as her sissy maid.Doing all the chores,entertaining her and her guests. she already planned to retire ,she planned to purchase a young boy for 20 lakhs, make her as Hijra(live in sissy maid) slave.Whole village knows about it.Even my wife too.
Mother in law slowly fall asl**p, i put her legs from my lap on bed ,covered... Continue»
Posted by tanyakrish 1 month ago  |  Categories: Fetish, Shemales  |  

Cross Dressing Cock Slut Party

Sadly this wonderful story is just a fantasy, but who wants to make something similar a reality!?!

The evening had taken a while to arrange, but had finally arrived. All 5 guests turned up within 15 minutes of each other and as they did, I fixed them a quick drink and showed them into the living room to get to know each other. Alan was a suited businessman in his mid thirties. Dave and Brian were dressed casually in jeans and Tshirts and both in their mid forties. Jeff and Keith were my age, early fifties and dressed in a shirt and smart trousers. We looked like a bunch of golfing mates who... Continue»
Posted by sissydonna 1 month ago  |  Categories: Anal, Group Sex, Shemales  |  

My new assistant - her story, part 2

The next week the office renovations were finished and I started working for Mr. Anderson full time as his assistant. It was a busy week since the office was closed for renovations the week before. I dressed carefully for work every day: makeup, dress, panties, bra (lightly padded), skirt, stockings, and low heels. Although I was born male, I pass easily. I am 5'6” tall, 135 lbs, with a small frame and a small face so I was never masculine. I've been female all my life in my mind; with a little makeup and a little estrogen, no one is the wiser. I plan to keep my penis – it has been a source of... Continue»
Posted by MassMan669 1 month ago  |  Categories: Fetish, First Time, Shemales  |  


She set herself next to me on the couch in the lobby of the hotel I was staying. I was in a lousy mood and everything to lift me up was welcome. I had noticed that elegant strut that only Asian women have and the short summer cotton skirt that made her look younger than she was. Mid thirties, straight short black hair, her white shirt showing a promising decolleté.
"Do you like women?" she asked looking straight ahead.
I nodded.
'Do you like men too?"
Äre you a professional?" I asked.
'No, I am in heat." She replied off-handedly.
We hadn't looked at eachother and I felt she wanted to kee... Continue»
Posted by FetishFreddie 1 month ago  |  Categories: Masturbation, Shemales, Voyeur  |  
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