Shemales Porn Stories
Page 81

Lodgers Surprise

I had started my first job after leaving university. Having moved to a small town where I knew no one I had taken lodgings with a couple who had a large house a short walk from my office.
The couple were called Jenny and Mike. They were both in their fifties and had retired early and took in the occasional lodger. Jenny was about 5 foot 2 and was plump and sexy. She had good tits and fine legs which I often admired when I thought she wasn’t looking. To my joy she always wore nylons either stockings (I could see the garter bumps) or tights when she was wearing tighter clothes.
Mike was 5’11” ... Continue»
Posted by maninnylons 3 days ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 4371  |  
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My real story



I couldn't believe it. Here I was in bed with an older man – and one that I most wanted as he lay there sated by my ministrations to him.

It had all started two weeks earlier when I had posted an ad on Craigslist. Up until this particular posting I had always been pretty bland..."Willing to do anything."

Now what I had written was the following:
"Young 48 year old, looking for an older man, early to mid sixties, still sexually active willing to be my top. Would love to get together and decide what our roles would be and then keep them going whenever we meet. I am a submissive who lo... Continue»
Posted by lookin02 2 years ago  |  Categories: BDSM, Gay Male, Shemales  |  Views: 656  |  
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Seven Minutes in Heaven

This is purely a work of fiction about two 18/19 year olds...


It is the summer before our first year of college and we are home alone at his house. My mom works from home, but his place will be empty until his s****r gets home from her summer internship. We have been playing truth or dare since we got up this morning. However, as close c***dhood friends there are few questions to ask when we keep no secrets. Our game has purely consisted of dares.

Early on, I was dared to put on women's lingerie. Most of the day I have been dressed up in a black fishnet body stocking with a matching b... Continue»
Posted by pantiedslave 3 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 1319  |  
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He has made me the town slut

We live in a very very small town, and now I am the town slut. This is the story of how my obsession with one mans cock turned me into the town slut.
I had been sneaking over to see Phillip every chance I could after he had fucked me and let me suck him. I couldn't get enough of his cock. I tried to see him at least once a week. I would usually blow him, but sometimes he would have the time to fuck me good and hard. I get off work hours before my wife and Phillips wife works later so this gives me time after work to dress up and head over to their house for some sissy fun.
One part... Continue»
Posted by firstknightd 2 years ago  |  Categories: Group Sex, Shemales  |  Views: 3213  |  
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First BJ

Coming home one day a school bully caught me in an area of trees and bushes. He often tormented me and others, being a stupid bully. On this day he ran at me telling me to freeze where I was. I turned and ran. Which set him to cursing me and demanding I stop. He caught up with me and grabbed me by the shoulders. He got in my face and called me names. Fag boy because I was slight and feminine looking, wimp, pussy etc. I begged him to let me go home but my pleading only seemed to increase his pleasure in over powering me. Then he told me since I ran, he was going to de-pants me and make me wal... Continue»
Posted by Celine-Fache 1 year ago  |  Categories: First Time, Shemales  |  Views: 2425  |  
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Cruising and Swinging 3

Blackmailed
It was about an hour after dawn on the third day of our Mediterranean cruise. I’d left my wife Melissa, asl**p with our neighbour Roger in his cabin. We’d spent the previous day fucking with Roger in the ship’s sauna and in his port-side cabin. I awoke to watch Roger and Mel making love, but once they went back to sl**p I was wide awake and slipped out to go for a swim.
I had swum about half a mile and was looking forward to the rest of the day as I walked back to our cabin. When I got there, our Brazilian maid, Maria, approached me looking concerned.
“Meester Jac... Continue»
Posted by lankybacon 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 2570  |  
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Sissy slaveboy gets trapped & blackmailed Pt 1

I had been a submissive with ever more disgusting fantasises for several years now and had acted out a fair few of them over that time.
I was a manly, muscular lad who everyone looked up to and would think was the textbook "normal man".
I held a professional job, steady girlfriend and a good standard of living, to the outside world, the perfect existence.
Behind closed doors i had harboured a strong, submissive streak which i could simply never satisfy and a desire to be controlled and humiliated that just grew day by day.
I love to serve Dominant women and adore total degradation, shame ... Continue»
Posted by kinkyandfun 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 2295  |  
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My first experience

I had been dressing for a while but kept it very secret. I am a 5’11, 175 lb gurl who feels very sexy when I was dressed up. When I was alone in my dorm room I would put on sexy little outfits, make-up, and a wig and play with dildos that I had hidden in my dresser. No one in the dorm knew that I dressed up. I tried to keep it very secret. It was hard to do. I was on an all-male floor with a communal shower. There would sometimes be 5 or 6 guys showering at the same time. I would try to keep my excitement from showing and was successful most of the time. It was so hard not to stare at some of ... Continue»
Posted by taylorbaby 2 years ago  |  Categories: Shemales  |  Views: 2283  |  
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Tgirls

Shemale, tranny or as some like calling them t-girls, I like them. Im not talking cross dressers, I'm talking about the ones with titties, curves and sound like a woman. Being a bi male, to me its the best of both worlds. I like watching porn of them and honestly I prefer the ones of them doing a strip tease, ending with them stroking their cock and cumming all over themselves. 
I met one, unknowingly, once while playing around on a chat site. I was cruising thru the members "online" when I came across her profile where she had a good  picture of herself.  I sent her an Instant message and af... Continue»
Posted by rogue-1966 3 years ago  |  Categories: Fetish, Mature, Shemales  |  Views: 1331  |  
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becoming Rachel

I was about 15 when i found a bounty of porn magazines and female lingerie in the park near my parents house. Without thinking at all i grabbed it and took it home. that night after getting horny reading some of the porn magazines I tried on some of the stockings and silky lingerie. it was the sexiest feeling i had ever felt. they seemed like a natural fit for me, as i had a slim and somewhat girlish figure.

Over the next few months i regularly played with myself while dressed up and reading the mags. but after a while, without the magazines, imagining I was a girl, with my legs spread wi... Continue»
Posted by rachel_cd 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 3654  |  
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My latest foto shoot got extra freaky

I was fucking this hot yung guy and my fotographers cock started getting hard so I got the chance to play fotographer as I took pics of him pounding this guys hole bareback and dumping a load of cum in him.

I have got to do this more often it was very exciting.



HE TOOK THAT DICK LIKE A CHAMP

I will definately be seeing him again

... Continue»
Posted by sexychanel 4 years ago  |  Categories: Anal, Shemales, Taboo  |  Views: 2396  |  
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good fucking

thank god 3 months at sea not had rest or sex havin men around 24/7 can do things to a man,singapore been here few times wid times and some fucked up shit wow,
left for land 3 days leave was gonna make the most of it.
went in couple bars checking things out see what was happening,
found out there was a lady boy competition on thought what the hell always good for a laugh, never thought anything about it, as in men being women,
got in the club it was packed with sailors all with the same idea spose,
any way the guy in charge started to speak to the crowd asking if there was anyone
who w... Continue»
Posted by peternorth111 3 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  Views: 1107  |  
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My first Crossdresser - Part One

When she walked in to the restaurant I knew I was in trouble.

It was the end of three long days at the convention and I was tired. I had come down to the NASCAR Cafe for a sandwich, mainly because it was the only bar in the Sahara that didn't have video poker...I lose a lot of money playing video poker. Well there I am with my beer and sandwich, and I glance toward the entrance just as she's strutting toward a table.

Convincing she was not, a crossdresser without question. But pretty, really pretty. And the way she walked, shit, I was getting hard just watching her. She wore a tight bla... Continue»
Posted by abend 3 years ago  |  Categories: Fetish, First Time, Shemales  |  Views: 1529  |  
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The Superbowl

I was very surprised when my b*****r-in-law Tom invited me to watch the super bowl with some of his friends. The only reason he would “invite” me over was to be his little sex sissy, since he had enough pictures of me dressed as a girl sucking and being fucked by him I had no choice but to do as told.

This would be different, I thought because his friends would be there and he would never let them know he did any homosexual acts.

When I arrived Tom immediately hustled me into the bedroom. I saw right away the little French maid outfit on the bed and my heart sank. I protested, and said t... Continue»
Posted by pandys 2 years ago  |  Categories: Gay Male, Group Sex, Shemales  |  Views: 2284  |  
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How it all began

My mother had 4 c***dren, 3 girls and a boy. I was the youngest. My s****rs were 5, 4 and 2 years older than me. Being the youngest I had to do as my older s****rs told me, including being dressed up as a dolly to play with when I was 4. When the oldest started wearing make up at 11, I was used for practice by all three of them, so I learned how to apply it myself.

When the oldest graduated from high school and went into the Army I was the same size as my youngest s****r and took to trying on her clothes. The feel of her bra’s & panties was awesome compared to my cotton tee shirts & briefs... Continue»
Posted by Andii18 2 months ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 11654  |  
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Job Interview with an e****t Service

On my 18th birthday, I had a job interview with a local e****t service. It was actually my 16th birthday but I had managed to get a fake ID ;-) I had a female cousin that was e****ting for this service and when she told them that she had a crossdressing bisexual male cousin, they wanted to meet me!

I showed up to the interview completely in drag: black stockings, garter belt, stiletto heels, black miniskirt, red blouse, wig, face painted like a fucking whore! It wasn't long into the interview when I was informed that the job would involve getting naked with mostly male clients and asked ... Continue»
Posted by cdsexslut 2 years ago  |  Categories: Fetish, Group Sex, Shemales  |  Views: 2217  |  
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him again :)

Since my roommate has moved out Ive taken it upon myself to begin exploring my Transgender tendencies. I shaved my legs, cock, chest everything. As I walked through work the first day, just feeling my jeans against my smooth shaven skin was a huge turn on, I felt my little sissy clit getting harder and harder as the day went on, tugging my panties tighter and tighter against my little bitty pussy ass, as they get stretched out. Its so erotic knowing that I am such a slut, that underneath my dirty grungy work clothes is a sexy soft girly sissy begging to be abused by cocks. mmmm. Spending all d... Continue»
Posted by Chubby_Decatur_Sissy 3 years ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 1132  |  
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my first tranny pt. 2

it hurt so bad but felt so damn good. I told her just to stay still so I can get use to it. get use to having a cock in my ass. that was a totally new feeling. it was something I always wanted to try. now I was.

she slowly started to move back & forth. not really pulling out, just enough to make me feel better about it. she was stroking my cock, which was rock hard. I could feel her balls on my ass. deep down i was freaking out. this is really happening. I knew that coming here I was going to fuck some ass. not get my ass fucked.

eventually, I got use to her cock in my ass & she was pu... Continue»
Posted by radec_24 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 1432  |  
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Summers of Love (Part 1)



A couple of weeks ago my wife hosted an Ann Summers party. I had hoped to sneak away for the evening as, though I would have been more than interested in the lingerie on display, I didn't fancy listening to the constant cackling common to "women only" parties and also the inevitable anti-partner jibes such as: "I ask are you in yet and he says I'm finished", "he picks his nose and farts afterwards" and "you'd think he was rodding a drain the way he goes about it" etc. The wife had other ideas however and I was drafted in to prepare the nibbles, pour the drinks and answer the door, the latt... Continue»
Posted by MichaelaCD 3 years ago  |  Categories: Shemales  |  Views: 977  |  
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t gurl at the bus stop

The radio was loud and the top was down when I first saw her.
She looked so beautiful sitting there at the bus stop.I remember her legs, they were long and tan and clad in silky smooth thigh highs. Her skirt shifted when she crossed her legs and I could see the garters clinging to her tan skin. She turned her head and smiled at me while I waited for the light. Her eyes were so bright. I think they were green, maybe blue. Every movement she made seemed to beckon me. As if she was calling me to her.

I couldn't help but stare at her tits - they were fabulous. A car behind me honked. shatterin... Continue»
Posted by allflavors 2 years ago  |  Categories: Hardcore, Shemales, Taboo  |  Views: 2381  |  
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