Shemales Porn Stories
Page 73

Tranny and Me Meet The MILF

This past Friday morning my phone rang. It was Chandra my tranny friend who I met and fucked some weeks ago. She told me that she had nothing to do this weekend and that her roommate was out of town and she was alone. I told her that if she wanted to get out of the city that she could spend the weekend at my place. She said that was a great idea and that she would be over in a few hours. When Chandra got to my place she was horney as hell. She dropped her overnight bag, dropped to her knees and opened my pants. She pulled out my cock and began to suck it really good. She was licking my balls, ... Continue»
Posted by adw276 3 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  Views: 1784  |  
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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 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 2568  |  
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Chatroom trick

I couldn’t believe I was doing this, as I stood by her front door I struggle to find breath on a surprisingly clear day. It had started some months ago, and internet chatroom, boy those things can be dangerous. I had spoke to Mary almost every night, soon chats turned to sex then to fantasies. The difference was she only lived in the next town so when she asked to meet I jumped at the idea, she was so sexy in her pictures. Admittedly Mary was 41 and I was 26, but still. She stood at 5ft10, long straight red hair, a body most twenty one year old girls would be jealous of. Stunning was the word.... Continue»
Posted by stig1963 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1342  |  
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The trannt from work

I've always had a thing about trannies. Just something. Never sure what or why. I loved looking at them. Seeing their huge tits. Their nice asses. Then seeing a dick between their legs. Now I'm not gay but, was always interseted. I would look up e****ts here in town just to see how far I would go. Finally one day, I got the nerve to do it.

Her name was Angelina. She was about 5'4". Say 125 with some hugh tits. Say 38 D or so. I had seen her where I worked. Would of never thought she was a tranny. Just always saw this hot chick with a huge rack & a hot ass. Everytime she came in the store, p... Continue»
Posted by radec_24 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 2656  |  
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ALL MY SINS REMEMBER'D part 3

After numerous flutes of wine Kathy Lee was becoming very vocal despite Hoda's vain attempts to silence her proved to be. The only think that silenced her was when she was sucking my cock. She held it in her hands and then cast glance over at Hoda and a mischievious smile smile across her face.
"Reminds of that visit to the farm," she said. "Remember, Hoda. The stables?"
Hoda's face tightened and reddened and she gave Kathy Lee a solid punch on the arm and pushed her head downward and filled her mouth with my engorged prick. She cast a nervous glance over at me, which I responded with an... Continue»
Posted by slappywag64 2 years ago  |  Categories: Celebrities, Sex Humor, Shemales  |  Views: 461  |  
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Workout

Several times a week I go to the health club for a mild workout. I often see a guy named Mike. We chat as we workout. Now I am a secret TS so I'm totally clean shaven but also lots of guys who are into working out are also. Anyhow Mike is a real hunk! As most guys do Mike will make an occasional joke about the size of his penis. The bulge I secretely glance at looks pretty good but real size hard to tell. So last week we were done together so we were showering & boy was he right about the size of his cock. So he caught me looking & said "see told you it is pretty big". I said "yes it ... Continue»
Posted by nyloned1 1 month ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 4839  |  
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MY GIRLFRIEND HAS A PENIS???

I met Gina at a club she was by herself at the bar and when I looked at her I was smitten I knows that sounds cliche but it was like that for me! I sat down a few seats down and ordered a drink a whiskey sour I believe it was took a few pulls to get up my courage then I offered to buy her a drink and she looked over at me with these incredible sea green eyes and actually smiled at me "Ok " she said and ordered white wine which she sipped so sexily I asked her if I could sit beside her and she patted the seat next to her I couldn't believe my good luck to find such a babe here and she likes ... Continue»
Posted by laceysgirl 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 4105  |  
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first time crossdressing exp

well this hapened a few years back,ive always been into wearing lacy underwear etc so i put an add in for anther knicker wearer for fun in an adult contact site,and was amazed at the replys,anyway i met a guy and we got on so we arranged a meet later that week at his house,i got there had a couple of drinks as it was our first bi experience, so he went upstairs to get changed and i got changed downstairs i put on black see through lacy knickers sockings and matching bra and mini skirt white blouse and a wig,dave came down wearing a very sexy outfit which was similar to mine also complete with ... Continue»
Posted by mumlover1960 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 873  |  
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Charlotte and her sister go swimming

I did not write this story.

I am 18, I have a younger sibling who is 2 years younger than me called Emily. Even though she is younger than me and we both come from the same parents, she has a better body than me. She is curvy, taller than me, wider hips, small waist, amazing big round ass and huge tits. I'm a D but she is an E, almost F. She turns me on a lot, I know it's wrong but I get horny thinking of her naked.

We both love our swimming. Even though this is an awkward sport for me as I am tiny and it is hard for me to hide a big 8 inch cock. I usually tuck it between my legs pushing... Continue»
Posted by drew1207 3 months ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 4542  |  
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A Special Girl - Birth of a Special Girl

A Special Girl - Chapter 1

By Alhana Escher

Birth of a Special Girl


James’ world had been turned upside down. Just moments before he had been getting off with, in his opinion, the cutest and sexiest girl in school. Now though, his was totally freaked out sitting on his living room floor having just discovered his girlfriend Alice wasn’t actually a girl at all. He had found out when his hand, that had been slowly making it’s way up her legs underneath her dress had reached the silkiness of her knickers to find a unexpected surprise waiting within. A small, but definitely hard ... Continue»
Posted by AlhanaCD 2 years ago  |  Categories: Shemales, Taboo  |  Views: 2340  |  
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school teen gay crossdresser first time sex

A young cross dresser's first gay experience
I was just a young boy then, senior in high school, horny as hell and dreaming of my first gay experience since sitting in my new red lace thong and white lacy bra and discovering the one porno in the house everyone kept hiding from me. I guess they thought my s****rs panty drawer held no interest for me......they were wrong.

It had been a great afternoon jacking off in my new bra and panties and watching my first porno when it happened, I saw the most beautiful thing ever, Peter north titty fucking a hot blonde and cuming all over her face. I w... Continue»
Posted by allisontranny 12 days ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 4073  |  
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Daddy's whore

I had always been fascinated by the feel of womens clothes against my skin, and today was no different. Mom was away on a business trip to Canada, and dad was away at work for the next couple of hours.

I had always had an effeminate look to me, with me being 6’1” and thin as a twig at 19, I was scrawny. I had bought a black wig to go with the outfit that I had picked out. It was black 6” heels, black pantyhose, a black garter belt and panties, with a short black skirt and a little black tube top. I was hard just thinking about what I would look like.

I took a shower and completely shaved... Continue»
Posted by vince01 1 year ago  |  Categories: Gay Male, Shemales  |  Views: 4377  |  
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Sissy Slut Amanda Part 1: The Beginning

The Story of Sissy Slut Amanda

This is a story of fiction

Part 1: The Beginning


When I was twenty-three I meet my Sissy Slut Amanda for the first time. Now he was only eleven at the time and it would be many years before I would know him as Sissy Slut Amanda, but still funny to look back at now. The first time I met my future sissy slut, he was Mark, son of the woman I was dating. He seemed like a nice k**, very shy and timid but sweet nonetheless. It’s wasn’t too long after our first meeting that I would be asking his mother to marry me. We had a good marriage and although I nev... Continue»
Posted by TheSissyFucker 1 year ago  |  Categories: First Time, Shemales, Taboo  |  Views: 2502  |  
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A true story: me and a transvestite man - part 1

This isn't a 'story' at all, in the sense that it really happened. I just thought I'd share my experience with you; perhaps you'd care to comment if you enjoyed it, found it sexy, or want to know more.

There isn't a 'transvestite' niche on xHamster, so this is filed rather awkwardly under 'Shemales' 'Gay male', and 'First Time'.

OK, about 10 years ago I discovered that I got turned-on by 'shemales'. Let's be clear about that: shemale is a casual term for transsexual men, that is, they were born with a male body, male genitals, but for whatever reason, don't want to live as men. Today,... Continue»
Posted by LookingForSomething 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1081  |  
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A Slut is born


There I was, one week before the end of high school. Going to college in the fall. Nice car, good f****y, friends.
I had it all. So, what was I doing on my hands and knees in a video booth on the wrong side of town,
dressed as a cheerleader with a cock in each hand, one in my ass and one buried in my throat?
It had all started a few months ago. I was locked out of my house in the pouring rain,
and I went over to our neighbor’s to see if I could hang out with him until my parents got home.
He was a cool guy... Continue»
Posted by vosmou_vrot 10 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 4242  |  
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cruisin the park for sex

when I started crossdressing,I was bout 15,a few later I got my own place,and was able to do more,except getting in clubs.I was 19yrs old when I got my first appartment,and was not able to get in,cause at the time,the drinking age was 21.and the club,Call club park avenue,hottest gay cub in town,well it was the only one.well I would crise the park where the club was,which was uptown in a very nice setting.so on fridays,and sats nights,I drive around the park looking for hot guys to have sex withI would all way wear a short sexy skirt,and a low cut top,under that a bra,panties,matching gartbel... Continue»
Posted by blonde68 2 years ago  |  Categories: Shemales  |  Views: 620  |  
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Morning Routine at the Mansion of My Misstress


My eyes open with the gentle humming of my small alarm clock. I quickly shut it off so as not to disturb anyone else in the room. Its 4:30am, well before light creeps into the day and the room is now pitch black. Very quietly I rise up on my hands and knees and crawl off of the small doggy bed on the floor next to the big bed. It‘s embroidered with my name “Heather” in pink because it’s my bed and I’m the pet of my Mistress.

I’m silent when I move because I have done this so many times before. On all fours I make my way to the master bathroom and gently close the door behind me. I then st... Continue»
Posted by heatherlingerie 3 years ago  |  Categories: Fetish, Shemales  |  Views: 1145  |  
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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 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 1426  |  
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Courtney and Michael

I wrote this last Christmas Eve and sent out to friends who've provided me their email. I tried to include the photo that was the inspiration but couldn't get it to show ... it was stellar! So enjoy ...


"Oh Michael, you're company's holiday party is always so boring! Do we really have to go?"

"You know Courtney that I am expected to be there. I AM the Senior Vice President, after all."

Michael wore his typical grey business suit with a festive tie to the event. Courtney, a tall, shoulder-length blonde, wore a black mesh dress with black stockings and boots. The party was held ... Continue»
Posted by call_me_dana 3 years ago  |  Categories: Shemales  |  Views: 952  |  
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Bus Stop

Dressed with my red 17cm boots, fishnet stockings, transparent skirt and transparent top I was waiting at the bus-stop to go back to my hotel in Barcelona, but suddenly a car behind be honked.


A beautiful Spanish guy stopped and looked at me, he couldn’t leave his eyes from my beautiful huge tits under the shirt. He whispered into my ear, “Need a ride?” I wasn't even startled and thought if this guy would have a nice cock as his body it would be a good start for the night…. I said “Sure, let's go.”
I saw tha... Continue»
Posted by Sexysamara 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 1216  |  
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