Shemales Porn Stories
Page 76

A video shoot - Part 2 of 2

Now there are even more guys on set. About half seem to be jacking off. I ask John what he has up his sleeve and what he needs me for.

It a Bukkake film. Damn, I get to see Tina covered in cum. My cock twitches at the thought. John tells me he needs a fluffer. I don't quite understand. After all Tina is just damn hot. Who would need a fluffer to cum on her? John says Tina is too girly. WTF? He says well some of the guys are gay and are having a hard time getting up. No pun intended. I now get what is happening. I protest weakly. But I am almost in pain from being horny as hell.... Continue»
Posted by nobodywashere 5 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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My first encounter with a man

As usual when I was travelling I was sitting in my hotel room working. I finished my work while drinking a beer or two, as the tingling feeling started to grow. In my suitcase I had packed my outfits and my toys ready for some hotel room action. Although; action meant myself, porn and self-satisfaction.

I took a shower and washed away all the dullness of a day on travel. I was stroking my cock and balls gently feeling the hairless skin glowing, and my cock started to grow. Since I was eager to save up for a massive load I finished the shower and started to get dressed.

The black panties ... Continue»
Posted by theevilothertwin 26 days ago  |  Categories: Anal, First Time, Shemales  |  
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First time

first time

This is the story of my first careful steps outside as a girl. I was at time 23 years-old, living in a house
with 16 other students and had been trying on girls underwear for some time, but always in private.
This time I would try out somewhere else.
I found an erotic shop in town, which had a cinema in the back. Or actually 3 different cinema rooms,
all playing different videos. I went there dressed in my normal guy�s clothes but underneath I was
wearing my favorite lingerie: a black lacy thong with matching garter belt and bra and a pair of black
stockings. It was my firs... Continue»
Posted by vince01 3 years ago  |  Categories: Gay Male, Shemales  |  
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So you know women...

I was in another state in an extended stay motel for spring break. The girls were hot and the guys were hotter, I did not know which way I would go on this trip.

I had noticed two females that seemed to be daughter and mother, they would come in early morn and stay in their room. The young girl was close to my age and very light skinned, the one I thought was her mother was some what darker and had a heavier build.

One morning I was returning from an all night party and was just a little bit d***k. I saw them as they pulled in and the elder of the two ran from the car saying someth... Continue»
Posted by d4david 3 years ago  |  Categories: Anal, Group Sex, Shemales  |  
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thursday night at the Gloryhole

So I went out to meet some friends on thursday, after a day of drinks we split or seperate ways. I started walking towards union square with the intent of grabbing a few drinks then heading home. As I got there I saw the bars were crowded so I started walking farther into the tenderloin not really with a destination in mind. I was walking on polk when i saw Frenchy's adult store, the sign said video booths, being a bit tipsy i figured why not see what was going on, so in I went. I grabbed some tokens from the guy at the register and headed into the back. There were a few booths organized in ... Continue»
Posted by tat2sf 4 years ago  |  Categories: Fetish, 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 4 years ago  |  Categories: Masturbation, Shemales  |  
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A Black Tranny Fantasy

It was only when she emerged from the bedroom in a purple silk nightie that not only clung to her full breasts, but also betrayed the hint of a bulge between her legs, that I realised that it was actually going to happen: my fantasy of sl**ping with a black shemale was about to come true. She paused at the bedroom door and smiled at me.

'You like what you see?'

I did indeed, but my mouth was too dry for me to say anything, so I just smiled back and nodded. Sasha looked as good as in the picture I'd seen online on the e****t site. Chocolate brown skin, soft, generous lips, a cute smile, b... Continue»
Posted by amylee-jones 1 year ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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Carpool buddies revisited

This is a follow to my carpool story from earlier in the summer.

I had found a really good thing in my carpool group. It was refreshing not to sit in traffic alone on my work commute and my new friends were terrific, but it ended up lasting only a couple weeks. When it became apparent to everyone that Natalie and I were sl**ping together, the group dynamic got a little uncomfortable. I don’t think there was any jealousy really, but it stopped being fun for one reason or another. That was cool with me, as I’m always running solo anyway so I decided to tell the girls I had to leave... Continue»
Posted by ocmike 2 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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Visiting shemale goddesses

Sexy hung shemales have long been a favourite of mine and over the years i have had several sexy encounters of all kinds. As ive got older it has become more appealing to have these beauties top me if possible. Most ive met have been quite abrupt and arrogant and have suited the top position well. Not every experience has been nice. However my last one was a really nice suprise.
I was in Amsterdam working for a week and had a 3hr slot early afternoon to amuse myself so took a short walk around the red light area. I am a nicely dressed and reasonably decent looking transvestite so find the she... Continue»
Posted by Jennifertaylor 3 years ago  |  Categories: Anal, Hardcore, 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 3 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  
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Virgin Sissy learns her place in life

As with any relationship, things change. The suprising thing that happened between me and Martin was at the begining he was a bit soft and I was the dominant person. It could have been that he was new at college and a bit shy. But as the summer went on he bacame a member of the Football, Tennis and Hocky teams. All the better as far as I was concerned as he had three different kits for me to sniff and lick after he had been playing. Blue top,shorts and socks for football, white t shirt shorts and gym socks for tennis and Blue top and white socks for hockey.
One Saturday, Martin turned up at ... Continue»
Posted by igglepiggle 3 years ago  |  Categories: Fetish, Shemales, Taboo  |  
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Careful not to cum too quick!

I'm a 42 year old married bisexual guy, slim built, average height and shaved below. I've had a few encounters with other men but none dressed as a Woman. I've had fantasies for years about wearing women's clothes and make up. Unfortunately I haven't had much opportunity for either, that was until a few months ago.

After my initial encounter I took a little more time to plan my next step. I'd had time to reflect about my first time experience, some things had gone well some not so. Next time I decided I would plan everything a little better, making sure to do a better job on my make... Continue»
Posted by jimbo70xyz 3 years ago  |  Categories: Anal, Fetish, Shemales  |  
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Cindy Growing Up

My first memories are of my mommy playing dolls with me in my
crib, and singing softly as she nursed me. I grew quickly, and I
was a chatty little k**, and by four Mom would take me out to
play with the other little girls. I remember always being dressed
in skirts and layer after layer of soft, frilly underwear.

I was treated like a little princess, and by five I was told that
my father had died just after I was born, leaving Mom enough
money to raise me without worry. I also learned I was different
from the other little girls. Mom explained that some people are
born without parts, ... Continue»
Posted by alex_wd 3 years ago  |  Categories: Fetish, Shemales  |  
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Shemale Cam Girl Sample

Sample from "The Shemale Cam Girl" available on Amazon (http://www.amazon.com/dp/B00R0BADB8).

“Yes,” she pushed him down onto the couch. “Look, if you are going to suck my cock you are going to have to get better at it. I don’t just let anyone suck my cock, you know,” she shook her head and laughed. “I mean, you saw it? That’s not the kind of cock you just let anyone suck on and Joel, hon, that was not a very good blowjob.”

“I’m sorry,” he hung his head, not sure how to respond.

“No, it’s okay,” she lifted his chin up, leaning in and planting a kiss on his lips. “It was your first tim... Continue»
Posted by rehumanize 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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The Surprise Visit

I had been chatting for some time online with a guy who said he liked crossdressers and loved getting his cock sucked. we chatted numerous nights, roleplayed online. i guess, i don't remember, but i guess i gave him my address. but i worked long changing hours. one thursdau night about 2 am i was coming home from worked, turned onto my street when i saw a strange car parked there. as i drove by its headlights came on and it pulled out following me. i parked in my driveway and watched as it slowly drove past me. i was in the house about 3-5 minutes when i heard a car door shut then footste... Continue»
Posted by cdamanda 5 years ago  |  Categories: First Time, Hardcore, Shemales  |  
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#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 4 years ago  |  Categories: First Time, 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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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 1 year ago  |  Categories: 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 1 year ago  |  Categories: Anal, Gay Male, 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 5 years ago  |  Categories: Shemales  |  
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