Shemales Porn Stories
Page 78

My First Tranny Experience

I was in my mid twenties when I first became attracted to trannys. This was before the internet and it was harder to meet people, but I found an advertisement in a local newspaper for a TV named Susie who offered a massage service. I phoned the number and she sounded nice so I made an appointment.
I arrived on time at a small apartment block near the city centre. I was extremely nervous as I knocked on the door and waited for a response. The door was quickly opened and I entered, not knowing what to expect. I was very relieved as I walked in to see that Susie looked lovely. She was tall... Continue»
Posted by mjam21 11 days ago  |  Categories: Fetish, First Time, Shemales  |  
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The Tutor and Jenny (Part 4)

The Tutor and Jenny (Part 4)
by Claude van Feinbode


My knees were a little weak as Rachel walked out of the room. I realized that I was keeping my guest waiting and I quickly dressed in blue jeans, black button up shirt with French cuffs, jacket and comfortable shoes. I splashed some cologne and walked out of the master bedroom.

As I walked down the stair towards the main sitting room I heard Gina and Jenny talking while music was playing at a low volume. I smiled and marveled at how Gina had the ability to make anyone feel at home.

"Claude," Gina said. "Its a... Continue»
Posted by NiceGuyz4u 10 days ago  |  Categories: Group Sex, Shemales, Taboo  |  
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How My Husband Fell in Love With Me and Decided to

do you already have a personal cock-servant? i am looking for a man who would take me in as au-pair for the summer. i clean, cook, do your laundry - and suck your dick whenever you want and keep my ass ready to fuck for you - hopefully, you will soon be used to falling asl**p with your dick in my twitching asshole and never leave the bed with full balls in the morning. I keep near you over the day - follow you in a little distance or walk right next to you - until you feel the urge to grab my pants, pull them down quickly, and enjoy a quick and hard fuck into your little fuck sluts hot and oil... Continue»
Posted by spermmakesme 10 days ago  |  Categories: Interracial Sex, Gay Male, Shemales  |  
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My Journey part 1.

My Journey.


As I sat in a small bar in a pub I thought back on my life and how it had brought me a Fifty year old cross dresser to this place and time.
Back in the late 70s and early 80s all the top shelf magazines were full of “lipstick lesbians” dressed in sexy satin and lace lingerie in various poses so when I got hold of some of those magazines the connection was made between feminine beauty, kissing, tongues, sex, satin and same sex love so all that was to follow in my life seemed to follow on from that for me.
I had began to enjoy satin ling... Continue»
Posted by silknsatinxxxx 9 days ago  |  Categories: First Time, Gay Male, Shemales  |  
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Busted

Busted
Nikkie Silk
“Happy is what happens when all your dreams come true," Stephen Schwartz
Sandy came into the bedroom where I was still dozing, holding a pair of tights in her hand.
‘Babe, I wouldn’t ask, but I’m so pushed for time and I’ve just laddered my last pair of clean tights. I desperately need some before I go to this client meeting.’
She held them up as if to prove what she was saying.
‘OK,’ I said, still half asl**p, ‘what can I do about it?’
‘Can I borrow a pair of yours, pretty please?’
My eyes snapped open. What did she just say? I rolled over to look at her and my hea... Continue»
Posted by nikkiesilk 5 days ago  |  Categories: Shemales  |  
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The Party ( Part 1 )

Hello Folks,

In my blog I had mentioned that I may tell the story of the night I dressed as a lady and went out in public. Please remember that I was only 20 years old at this time and of course it was not exactly accepted back then. At 55 now, I still look back on this evening with joy.

I was in college in the North Carolina, I was a a skinny guy at 5'7" and only 140 lbs. I was trying to get in to a Fraternity on campus, but really had no chance since it was basically a jock frat. The only reason I wanted to join was because of a few friends that I had there.

I was at one of their pa... Continue»
Posted by JayDon1960 2 days ago  |  Categories: Gay Male, Shemales  |  
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Crossdressed Pigslut Takes a Cottage Assault

my sexual deviance is based largely around the high heel... of course with the females who wear them but also the nastiness i can get up to when wearing them myself..
i wont meet anybody for sex unless i'm wearing a pair of fuckme heels which are of a certain standard , the idea of wearing just stockings revolts me , as does wearing a pair of heels that i deem un-sexy.
the next obvious step up from wearing heels and lingerie and little black dresses is to be presented to somebody else who appreciates this sort of presentation. these somebodys are easily found online , however they can al... Continue»
Posted by THE-HEELS-STAY-ON 2 days ago  |  Categories: Anal, Group Sex, Shemales  |  
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The Cop & The Chubby

-Wyd?
-Watching TV. You?
-Laying in bed dick hard thinking bout your fag pussi hole.
-Oh wow!
-Come over tonite. My wife is getting ready for work. k**s are sl**p.
-What time?
-Be here at 11:30. You can stay til morn.
-OK.
-You know the drill. Park at the Krogers on Wynnton. Text me and I’ll come pick you up.
-OK Daddy. See you soon.

Russell Jones put his phone back on the nightstand. His wife of nine years exited the bathroom fully dressed in her scrubs. She kissed him before heading out of their two-story Dutch Colonial style four-bedroom house. She was on her way to the hospital... Continue»
Posted by faggyboi 1 day ago  |  Categories: Anal, Gay Male, Shemales  |  
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My new flat

I had not long turned 18 when i moved into my first council rented flat, before then i had been living at home and dressing up in the confines of my bedroom chatting to guys on web cam , some of them knew i was not a girl, but most of them did not.i am only 5ft 6in tall and weigh just under 10st i guess i have never been what you would call masculine .
i had been looking forward to and planning so much for when i moved in and had been out shopping for so much girly stuff for my new life.
I had not long got out of my Bath , skin was smooth not a trace of hair to be seen, i had spent 20 mins ... Continue»
Posted by julieanneff 4 years ago  |  Categories: Fetish, Shemales, Taboo  |  
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black man's sissy boy

I started jerking off to ejaculation when I was around 18. Once I started doing it, it was all I thought about, 27/7 it seemed like. I collected fuck mags and porno tapes wherever I could find them, to use as visual aids. Just looking at those sexy nude women being loved up by their hot men made my dick so fuckin' HARD! Because of that I was able to convince myself that I was normal, of course, in retrospect it is obvious that I was identifying with the women.

One day when my mom was at work, I was laying in her bed, masturbating. I got up and rummaged through her underwear drawer. The draw... Continue»
Posted by nicoleinberlin 3 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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Crossdresser has cinema fun

It had been a few weeks since I'd had any action as Clara and was absolutely gagging for some cock. The girlfriend was away for the weekend so I planned a nice Sunday afternoon in a local-ish sex cinema. I got partially dressed at home wearing black hold-up stockings, black bra with inserts as well as see-through black panties, and a matching vest-top. I pulled on a pair of jogging bottoms and a sweatshirt, pulled on a pair of trainers, packed the rest of my stuff in a tote bag, and left in the car. The journey was uneventful apart from me feeling very lightheaded from being in a constant stat... Continue»
Posted by claracduk 4 years ago  |  Categories: Fetish, Group Sex, Shemales  |  
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she showed them the pictures

Some years ago, While my wife and I were separated, I was out of state and she called to ask if she could use the computer at my place. When I returned home she asked about the pictures she found of me all dressed up like a whore with some guys cock in my mouth and of me setting on a dildo and taking the whole thing. I made up some story about I was experimenting with a fantasy I had but that I didn't like the real thing and I was done with that fantasy. ( I told myself she bought it.) We never talked of it again and we got back together. Life went on. Last Halloween her friend Tina and her hu... Continue»
Posted by firstknightd 4 years ago  |  Categories: Shemales  |  
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Nice surprise on the journey to work

This is a deliciously erotic story sent to me by my fellow writer Ila, I hope you enjoy it as much as I did and also the second part of the story which is to come..

I got up early this morning for a change.  I had a feeling that today was going to be a good day.  At the time I didn't realize just how good.  The sun was shining for the first time in several days.  That, at least, was a good sign and an improvement over yesterday's rain.

I headed off to the bathroom for my morning ritual.  A quick shower and then I was ready to get dressed.  I put on my normal businessman's uniform ... Continue»
Posted by keliana 5 years ago  |  Categories: Shemales  |  
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A walk in the woods.....

I was lounging around the house, like a lady of leisure, wearing an elegant robe in black lace with a pair of sensual seamed stockings held up by a six-strap suspender belt and of course a pair of my favourite spiky pointed hi-heels that are so comfortable to wear round the house. I'd put on one of my favourite bras and placed a nice pair of natural looking silicone titties inside - the whole ensemble topped of with some nice jewellery. The perfect femme fatale bourgeoise SLUT that I LUV to be. I'd just renewed my lipstick and was feeling very femme, VERY slutty and as HORNY as hell when the p... Continue»
Posted by caroletv31 4 years ago  |  Categories: BDSM, Group Sex, Shemales  |  
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Sissy Mailee's first black cock - part1

As long as I could remember I have always had a craving for black cocks. My first time was a few years ago after partying with a friend of a friend.

I had called up one of my CD friends, Suzy, to attend a Halloween party at a local warehouse. We had agreed that we’re both going to the party as slutty school girls. We met up at her place to get dress together. When I arrived at her place she told me she can’t go because she was coming down with the flu. There was no way I was going out in public for the first time by myself. I was super disappointed but she told me that her friend Brad woul... Continue»
Posted by aznfemboi 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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Party Surprise - First sex as a Crossdresser.

This is a work of Fantasy. I hope you enjoy.

Stephanie and I had been married a few years and enjoyed a reasonable sex life. She knew of my dressing and although she didn’t approve she indulged me now and then and we had sex when I was dressed or with me wearing lingerie. I think secretly she was jealous of my legs. She was a petite sexy woman and we were almost the same size but I still had my own stuff that I’d secretly obtained from eBay and op shops.

I didn’t consider myself bisexual, certainly bi curious at least. I liked watching guys stroke on cam and enjoyed the odd bit of cybers... Continue»
Posted by SatincdAus 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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my uncle

The other day I was dressing up in my s****rs tight little black dress, I know I'm passable bit I had no idea how much... Well anyway I always heard I would look like my s****r if I had a dress on and believe me I did. So on this day I had some free time, or so I thought... I spent the day procurring my s****rs things and a few of my mom's.. see my mom doesn't have hair these days in her old age, and she is some what of a wig addict... So she has a great collection, my slightly older s****r helps her buy all of them so they are "hip styles" in moms words.. but I did my hair and makeup the sam... Continue»
Posted by 612Goo612 3 years ago  |  Categories: First Time, Shemales, Taboo  |  
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CD at truck stop with three men

Went to a truck stop last night after a party around midnight in my sexy short dress, got out and bent over looking at my tires for assistance. Gave a nice view to whoever was watching of my smooth white ass and sexy black panties with pink trim with half of both cheeks exposed. A nice older (63 yo) black guy (Ted) asked me from his truck if I needed help. We talked and then thanked him and asked if I could help him for helping me.

We walked over to his truck and got in his sl**ping quarters. Gave him some more intimate show of my nice ass, turned around, unzipped his pants and began ... Continue»
Posted by hotcdsub 3 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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Slave Life: Part 1

Prologue: My thick thighs quivered and shook as the man standing behind me, my Master, fucked my tight cunt into the bathroom wall. My loud moans filled the room as I shot a huge load all over my thighs and the floor. I had never been fucked like this before! I didn't care who heard my loud moans as they echoed across the tile filled bathroom, and I didn't care who heard the sound of my Master penetrating my ass with his enormous cock. Just then my Master moaned and shot his load deep into my tight, warm, and heavily fucked ass. When he had finished pumping his load into my ass, the warm and s... Continue»
Posted by Slave_Alice1389 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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Sissy Emma is Turned Chapter 7

Steve unlocked me from the cage and handed me over to Master. I went to wipe Steve's cum from off my face but was told to leave it.
'So Sissy that's 3 serious demerits you've earned for that little escape attempt. I warned you not to mess with me but you just couldn't help yourself could you?
'No Master' I said sheepishly.
'Right well get yourself home and learn to follow orders' he said. 'I want you to have an early night and watch the videos I have given you on your ipad. And don't forget to take your pill first. Finally, Steve here has agreed to keep an eye on you at work and ensure you ... Continue»
Posted by emmahighheels 3 years ago  |  Categories: Shemales  |  
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