Shemales Porn Stories
Page 70

A true story: me and a transvestite man - part 2

OK this is the second part of my true story. I was going to leave it at two parts, but I think there's enough to make it three parts, now!

I think I'd best point out that beyond the (I'm told) common early sexual experiences most straight men have as youngsters, with other men of their age, I'd not had any experience of men. You won't, of course, get many straight men who admit to this. But I'm not like most men.

However, this early experience was enough to leave me curious as to what it would be like to have fun with a cock. As you may have read in part one of this story, I was rapi... Continue»
Posted by LookingForSomething 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1055  |  
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The Cheaters

“God yes,” Lisette moaned as her husband flicked his tongue in and out of her hole. The five-foot-ten-inch brown-skinned beauty grabbed his head with both of her hands and pushed his face deeper into her ass crack. As he made love to her tranny pussy, her body, all one hundred and forty-five pounds of it, squirmed. She wiggled in every direction effectively working the fitted satin sheets off of their California king size bed. Her barely functional clit stiffened. “Fuck me,” she squealed.

Sensing his oral work was finished; Deitrick emerged from her anal cavity and stood on his knees. He ad... Continue»
Posted by faggyboi 2 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 1638  |  
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dogging tv slut

It was dark enough now I thought. It was about eight o'clock on a warm spring evening and I was ready. I had started getting ready about three hours earlier. I'd showered, cleaned all those special parts, applied my make-up heavily and dressed. I was wearing a skimpy flower print top over a black silk bra, my favourite suspenders, black leather micro mini skirt, black gloss stockings and high heeled black knee length boots. I peered from out behind the curtains. Yes the street was clear apart from some young lads on the nearby street corner. It was only about ten yards to the car. Quickly I c... Continue»
Posted by JuliaMiller 2 years ago  |  Categories: Group Sex, Mature, Shemales  |  Views: 1186  |  
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The Making of A Sissy-Part Two

As Bella blossomed physically, Jane ensured the girls took control of her; she was made to know her place amongst females and was still subjected to their choosing her outfits. Bella was habitually made to pose before a full length mirror as Jane and the girls scrutinised her feminine shape; the girls were especially pleased on those occasions when Bella was held naked before the mirror as they stroked and admired her sweet white thighs and bottom, cupped her deliciously formed breasts; the smiling girls actions making Bella’s sissy hairless cock rise with excitement. This gave Tara licence ... Continue»
Posted by midsummerman 2 years ago  |  Categories: Fetish, Shemales, Voyeur  |  Views: 1144  |  
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A gym workout

A few weeks ago i started going to the gym. I liked it because it was normal size and there wasnt too much people so wouldnt have to wait. My trainer was the owner af the gym and his name is Nikola. When i first saw him i was amazed. He had big and nice muscles and was very handsome. He showed me how to work out and while he dide that i noticed that he had a big dick in his shorts. So after a couple times i decided to go for it and put on some stocking,a skirt, a black thong and a black bra,a shitr whic showed more than it hid, a pair of high heals and went to the gym. I got there at around 8 ... Continue»
Posted by nikoletakurva 3 years ago  |  Categories: Anal, Shemales  |  Views: 1443  |  
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Finally, My First Tranny!!!

I just came out of the doctor's office in downtown Philly from my 3 month check-up. I was pretty horney since my doctor is a female and I had a complete physical so she and her nurse were in the room with me. I got to the train station to go back to Willow Grove and was standing on the platform when I saw this beautiful brunette haired woman about 10 feet from me. She was wearing jeans, and a spagetti top shirt. I could see that she had a real nice pair of tits and my cock started to get hard in my jeans. Being horney and looking to get laid, I walked over to her and introduced myself. There w... Continue»
Posted by adw276 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 2929  |  
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My sissy son by his dad and lover Part 5

Well...what a few months it's been since i/we last spoke to you.Many things
have happened,some of them great,some fantastic..some not so good,best tell you!

Lucy and i are in love,no two ways about it,we found out how to change her name by deed poll(to legally change your name in the UK)So she's now,legally..Lucy Alice Andrews and she wears a matching wedding band and engagement ring like mine.I wear just the band when we go out together,as i said..she passes for a woman no problem.So people just think i'm a guy with a younger/sexier trophy wife,(which in a way is right!) She dresses as Lu... Continue»
Posted by chocandres 2 years ago  |  Categories: Anal, Shemales, Taboo  |  Views: 1238  |  
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GF And I's Threesome With A Shemale (True)





This is the true story of when my girlfriend at the time and I had a threesome with a shemale off Craigslist. Enjoy


At the time of this story which was a couple years ago I was dating a girl named Miranda she was sexy,funny and kind of kinky which was everything I looked for in a girl I guess. We had been dating for about five months and after the third months we had begun talking about having a threesome with another guy or girl because Miranda and I are both bi... Continue»
Posted by xXSecondCitySaintXx 22 days ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 10791  |  
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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: 654  |  
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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: 1315  |  
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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: 2257  |  
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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: 2282  |  
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My fucking f****y

I'm really proud of this would love some feedback


Why was I on all fours with my dad's cock in my ass and my s****r's pussy in my face? Well little did I know that my mom knew about my secret. She knew that I had been wearing her and my s****r's lingerie.

It started when one day I was home alone and wandered down to the garage to play around on the air hockey table. I got bored and looked around as we had a lot of stuff down there. Boxes were piled up on one side and I looked in a few of them and found something that made eyes pop open.

I saw a naked girl on the cover of a magazine... Continue»
Posted by 6270daniel 1 month ago  |  Categories: First Time, Shemales, Taboo  |  Views: 7902  |  
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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: 1321  |  
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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: 2391  |  
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cumsquirter

I spent night at girlfriend's house last month, her older b*****r walked in on me while i was naked in bed, jacking my 7 inch shemale cock off to porn, have 34c tits, he did not know that i had a cock, so i asked him if he wanted to suck my cock. He put his mouth on my cockhead and cock and sucked me for about 5 minutes, then i came so much spunk in his mouth, he liked it. Then i jacked him off all over my tis, they were covered with his hot cock juice. We see eachother all the time now and cum all over!... Continue»
Posted by cumsquirter 3 years ago  |  Categories: Shemales  |  Views: 658  |  
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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 2 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  Views: 1106  |  
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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: 1515  |  
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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: 2280  |  
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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: 2211  |  
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