Shemales Porn Stories
Page 62

#1 - Nikki's First Experience

I had recently started my transformation and was just past 18. I was at the stage where I was just starting to dress as a female in public and friends convinced me to go out. At the local pub over the course of the night my friends all found someone and I had resigned to the fact that I probably wouldnt find anyone until a young guy in his mid 20’s approached me. He said my friends has told him about my change and he was very complementary saying I looked pretty convincing. Over the next hour or so we spoke in the pub about everything from jobs, hobbies and eventually if we were both single wh... Continue»
Posted by Nikki_93 3 years ago  |  Categories: First Time, Shemales  |  
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Mt tranny story

I've been dressing like a girl for the past three years. I've been a girl my whole life though. I always knew I wasn't the same as the other boys. I tried desperately to blend in and be a normal boy but couldn't. Behind the scenes, at home, I'd raid the laundry basket at night and grab some of my older s****rs clothes and underwear, rush back to my room, lock the door and indulge. I don't know right but even from a young age something about wearing woman's clothes was very liberating for me. From the age of 12, every night without fail I slept in a pair of French knickers. I had a set of girly... Continue»
Posted by stevolayton 7 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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The Slut on the Balcony

A night away from home on business always meant a night of crossdressing and exhibitionism. I loved to get a room with a balcony so I could easily be seen by men walking around the motel grounds. This night I'd dolled in in a black lace corset; heels, hose, and g-string. I slipped on a leopard print short spaghetti strapped dress over; poured some wine and strolled out onto the balcony. My red wig flowed over my shoulders and my make up was just a bit slutty. I put on a choker that spelled out cumslut in rhinestones around my neck. I just knew that I would get lucky this night. Another mo... Continue»
Posted by dana213 5 years ago  |  Categories: Group Sex, Shemales, Voyeur  |  
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Cross dressed slavery

Oh just try it on, don’t act so…stereotypical.”

I started to protest again, I mean I was not trying to be a jerk, but I did not feel like serving as Leena’s dress dummy all afternoon. I felt uncomfortable enough around her and her clothes. The way she dressed made me crazy and I knew she would tease me all afternoon if I let her. It was my own fault really, I approached her at her last ‘fashion show’ and offered to take some pictures. I really did like her designs, but mostly because of my own peculiar fetishes. Leena worked a lot with sweaters and wool, knit creations she called them, ... Continue»
Posted by stig1963 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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Gina C

A number of years later, after my first shemale expereince, I still had a penchant for a hot shemale or a slender sissyboy who was passable. That's when I met Gina, who fit the mold of a slender sissyboy who was much more than passable, she was gorgeous.

The first time we got together was on a rainy Sunday afternoon. My wife was out of town and I was cruising aroind on AOL in the SoCal Shemales chatroom. I came across her screenname and we started to chat. We traded writen descriptions of one another and she sounded very hot. She was white, in her late 30's and was married like me. Sh... Continue»
Posted by Blackpapi65 10 months ago  |  Categories: Shemales  |  
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Becoming Aphrodite Ch 01

My wife and I have been married for 10 years. She is a beautiful brunette of 5'8" and 120 pounds. With her long hair and her cute and innocent face, she looks a lot like the porn star Cheyenne Silver. I would dare to say she's even prettier: her extraordinary green eyes are totally unforgettable and even the famous porn star I mentioned could not compete with her.

We got married very young and we were very happy for many years but Jennifer was slowly changing, discovering parts of her which could not be ignored any more. In fact, she did not have enough sexual experience before getting marr... Continue»
Posted by slutyvanessa 2 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  
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Last night I drank my own cum

Once upon a time...

There was a regular boy, who was always fascinated by women, but one day (casually) discovered the dirty and horny world of the "third way" of sex, the fantastic shemale-ladyboy-tranny universe, and it was like a shock for him, a very sweet shock, he never believed or thought in exciting himself by watching a girl with a cock, but instead that new world electrified him, and made himself very curious about these she-males, widening his love above women and becoming a real sex pig and an orgasm addict.


Well, that regular boy was me. I consider myself as ... Continue»
Posted by Porcellone 3 years ago  |  Categories: Masturbation, Shemales  |  
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Cumming for Christina

I love you and will see you Friday night I told my wife as I hung up the phone. My heart began pumping big time as I hung up from my nightly call and the familiar ring of a new text sounded off. My cock stirred just seeing it was from Christina. The message read that the rendezvous was on for 10:00 with a room number and hotel. I cleaned up nice and fresh grabbed the condoms and lube and headed out.

My stomach was in knots as Christina answered the door. I quickly entered and stood frozen staring at her beauty. After months of exchanges on Xhamster we were together. Within seconds our lip... Continue»
Posted by iheartm2f 1 year ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Tabby Cat: Sex KItten

This story was posted under my old profile, sluttycdprincess, and I'm reposting it.

OK. So, this is my first story on any site, and I'm finally pleased enough with it to post. Hopefully people will enjoy it and if so I will definitely be writing more. Leave me comments or PM me about it if you want, I would love the feedback. I plan on making this a series, with all of the characters making more appearances and being fleshed out more. I also would like to write the story of my character leading up to this point. Her Origin story so to speak. Obviously the main character is transgendered as... Continue»
Posted by summer_angel_cd 8 months ago  |  Categories: Anal, Group Sex, Shemales  |  
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a real cd explains what cd on cd sex is like

alot of "strait" guys love shemale porn.I was one of them.Pre-internet I discovered shemale porn but it was hard to find.I had girlfriends but the sex was never great.like many i was more concerned with cumming to soon than actually enjoying myself.Plus,as a porn watcher my fav was anal.My girlfriends fav...not so much.after 25 years i realized that i was most unhappy when i had a girlfriend.even then I had bought and worn nylons and enjoyed anal dildo play alone.then came the net.and i bought a wig,shoes, and some makeup.I had wanted to be with a cd.I didn't realize i could be an attractive ... Continue»
Posted by tran1001 2 years ago  |  Categories: Shemales  |  
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Wife was Away!

I hadn't been out for over a month and it was starting to bother me. Since I started dressing four years ago most of my excursions in public have been from fall till spring. Its easier to hide my shaved body in the cooler months, which makes me feel much more feminine. When I'm smooth all over I get to wear more revealing clothes and I can let the guys I meet run their hand anywere they like without them getting turned off by unwanted body hair.

My wife was about to leave town for ten days at a convention she attends every year and as soon as I dropped her off at the airport I ru... Continue»
Posted by kristygurl 4 years ago  |  Categories: Shemales  |  
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IT WAS SO WRONG BUT SO NICE WE WAS JUST HAVEING FU

IT WAS WHEN I WAS 17 NEARLY 18 MY MOTHER AND FATHER SPLITT UP WHEN I WAS ABOUT 12--13 AND I LIVED WITH ME DAD IT WAS ALL GOOD WHEN I WAS 15 ME DAD MEET A NEW GIRL FRIEND CAFFE SHE WAS YOUNGER THEN DAD HE WAS IN HIS LATE 40,S SHE WAS IN HER ERLY 30,S THEY WAS WITH EACH OTHER FOR A WHILE THEN CAFF WAS MOVEING IN OWR HOUSE IT WAS COOL I WAS WITH A GIRL AT THIS I LOOK,T AT CAFF AS ME STEP MUM WE USE,T TO JOKE ABOUT HOW DAD WAS 17 YEARS OLDER THEN HER AN I,D SAY THERS THE SAME AGE GAP BETWEN U AND DAD AND ME AN U SHE WOULD SAY NO IM AN ADULT SO IS YOUR DAD U R STILL A TEENAGER WELL ATHTTER 2 OR 3 Y... Continue»
Posted by needyboy 4 years ago  |  Categories: Shemales  |  
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Babysitter - Part 2

From: A K little s****r Alyssia

Babysitter - Part 2

I'm a mess in the mirror, well, I think I look sexy too with my hair all
tussled, a little cum rubbed over my cheeks and chin, and a grin like the
cat that ate the canary. The dress has some wet spots and a few small gobs
of his cum. I wash up as best I can and blot the spots on the dress, I
start thinking, Nicole is going to kill me! I might have ruined her dress
and I just gave her man a blowjob. That could be a problem. I still can't
believe it!. He kissed me and I sucked his dick! But I know I want to do it
again.. Did I real... Continue»
Posted by jayymie 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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Walk his way

Just for the thrill of it all, I moisturized my freshly shaved body, combed out my long hair over my shoulders, and put on a pair of very short cut off denims, cuffed them even shorter, and a Betty Boop T shirt with the neck and sleeves cut out. I looked and felt very much on the fem side. Not really crossdressed, but without a doubt, sissified. I drove down the interstate to the nearest rest area and parked all the way at the end. I carried my little belly bag like a handbag, and walked to the rest rooms with a swish in my step and a grin on my face. Most people did a bit of a double take; a ... Continue»
Posted by dana213 5 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  
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Weekend with Kelly, my new lover, part 4

After we got out of the tub and ate dinner I asked her if she
was ready for dessert.


Her eyes sparkled and said "Of course my dear".



I told her I'll meet her in the living room.


She stood as I moved her chair back from the table. I kissed
her lightly on her lips.


Then, leaving the kitchen and going to the master bedroom
to get myself ready. I applied some lube to my favorite dildo
and slid down on it stretching my hole to ready myself for
her. Walking out into the living room and finding her relaxing
on the coach. She didn't hear me come into the room as
I snuck up... Continue»
Posted by Bigrodtaz 12 months ago  |  Categories: Anal, Fetish, Shemales  |  
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My First Meeting - A work of fiction

I had absolutely no idea what to expect as I rang the doorbell of Jane’s house. It was an extended bungalow on the outskirts of Edinburgh and it had taken me 30minutes to drive there, getting more nervous with each passing mile. Jane and I first contacted each other through as online transvestite networking site a couple of months previous. We had got on well, and often chatted in a private chatroom, and exchanged pictures of each other. While I was relatively new to being a tranny, Jane had been doing it for years, going on nights out and meeting people.

Jane answered the door, wearing... Continue»
Posted by misssuzywhyte 2 years ago  |  Categories: First Time, Shemales  |  
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About Me

I don't know where to start so I guess I will start where I first felt like I might like men. I was about 14 and walking to store for my grandmother. The neighborhood bully acosted me and when I was walking away he felt my ass. That was it. I don't know why but it felt good. I fought off those feelings for a while. Then when I was older I got an obsession with panties and lingerie. I started sniffing and wearing my s****r's. I fought that off. I went on to get married and then the urge came back. I started wearing and sniffing my wife's panties. I knew she was cheating on me and I would wait u... Continue»
Posted by pantyluver711 2 years ago  |  Categories: Gay Male, Shemales  |  
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Fantasy Cums True part 2

This story is written by Tittie-baby for xhamster.com any reprint without permission is strictly prohibited.

FANTASY CUM TRUE part 2

I woke up with Terri still sl**ping in my arms. God this woman was beautiful. She was so surprised that I didn't freak out when I found out she was a shemale. I have been with over a thousand women but Terri was my first shemale. Last night had been special for sure and I wanted to start the day off right too. I knew she would be getting up soon for work so I eased myself down the bed and took her limp cock in my mouth. I licked all around the head and the... Continue»
Posted by tittie-baby 1 year ago  |  Categories: Shemales  |  
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Sharon's Mistress Throws a Sissy Party

Sharon’s Mistress throws a Sissy Party
(Prior chapter is Sharon’s Sissy Saturday)

The next morning Mistress was kind enough to let me sl**p in, but an alarm above the door to my little cell went off at 6:30, rousing me from a delicious dream of being naked and fucked in the woods by a handsome, dark-haired man who kept me as his personal sissy slave slut. I woke with the sensation of his hard cock filling my dripping pussy, and I realized I was still leaking cum from my day in the booth. I crawled from my cell and saw a note from Mistress Angela telling me not to wash up but to dres... Continue»
Posted by scatpetsmaster 1 year ago  |  Categories: Fetish, Shemales  |  
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a naughty "girl" i was

Once again i had the house to myself, i got online and soon found myself an eager man ready to come plow me. I waited in my black tank and pladd mini skirt, running my hands up and down my thigh highs. Suddenly a knock at the door, i answered the door in a robe. After he came in i relized how big a boy he was. HE was easily 6'6" and round 250bls, i have to admit i was intimidated. I disrobed in front of him and a smile came aross his face. MY naughty little outfit had made a rather large buldge in his pants.
HE took his time with me, caressing my body and grinding ag... Continue»
Posted by witdacandy09 4 years ago  |  Categories: Shemales  |  
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