Shemales Porn Stories
Page 14

My First Gangbang

For as long as I can remember, I have always enjoyed wearing women's clothing. When I was in fifth grade, I started wearing pantyhose under my pants during the winter. By the time I was going into the seventh grade, I had learned that, not only did I enjoy wearing pantyhose, I also liked playing with peckers too ;-)

As you may imagine, I became VERY popular! Pretty soon, there wasn't a sl**pover in the neighborhood that I wasn't invited to ;-)

I quickly developed what would be a lifelong obsession: semen. And no matter how much I got, I still wanted more! The feel of it squirting into my... Continue»
Posted by cdsexslut 3 years ago  |  Categories: Group Sex, Shemales, Taboo  |  
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first time with a Tranny

My first tranny I had was back after I graduated from high school. I was working with her/him at a Wal-Mart store. We got along pretty good then we started to date, I was living on my own so we usually go to my apartment. I had no clue she had a cock, she was a very beautiful woman with size B tits. We dated for about a month when talk her into just taking her shirt off, after a while without her shirt off she finally took her bra off. I would make out with her and suck on her tits, lick her nipples. One day we were together I decide to change it up so I took my pants off in the bedroom and ... Continue»
Posted by theho_1 4 years ago  |  Categories: Anal, Shemales  |  
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A young man's summer [full story]


My name is Jason, and I am a typical teenaged young man; lean, horny all the time and really happy that I have reached the age where I can get a job that pays better than mowing lawns or delivering papers. My parents work all the time and me and my older b*****r John, have had the house to ourselves since I was 8 and he was 13, which meant no more getting up at 5:30 to go to a sitter who would either keep us all day or make sure we got on the bus for school.

I discovered the concept of sex early on; John would jerk off constantly if he thought no one was watching, this sta... Continue»
Posted by serious58 5 months ago  |  Categories: First Time, Masturbation, Shemales  |  
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How I got started dressing my true story.

As far back as I can rememeber I have always gravitated towards fem things. As a young boy I played with whatever girls clothes I could get my hands on. Which wasn't much. At 12 y/o I had a few pairs a panties and bras stolen from my cousins. One thanksgiving after dinner the girls changed and one of them left behind a black knee length dress and white pantyhose in the guest bedroom. I was so excited when I found them...needless to say she never saw that dress again. With the bra and panties I alrady had from her and the new black dress and white pantyhose...I had my first total outfit. My tr... Continue»
Posted by Sarahaspencd 10 months ago  |  Categories: Masturbation, Shemales, Taboo  |  
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beautiful tranny

This guy picks up a girl and takes her to his place. Can you imagine his surprise when he finds out that this girl has a dong?

Hi! My name is Andrew! I’m a 5.4 feet tall, with some cute beer belly, crew cut light brown haired guy, blue eyes. My friends say I have a big noseJ but it’s not that I should worry about! Men of my f****y have always been stocky, and thickset. So a big nose and stocky figure are not a trouble! I’m working in a Western City College as a tutor of English Literature. I teach student best masterpieces of Shakespeare and Charles Dickens, and so I am in my whole best! I ... Continue»
Posted by princessamyov 9 months ago  |  Categories: Anal, Shemales, Taboo  |  
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What is it about a womens bulge

A very attractive women once bumped into me in a very crowed club in Mexico City, I turned to say excuse me. I was speechless at her beauty. She was wearing a short skirt, garters below the skirt and knee high boots. She just stared at me and with out saying a word she bumped me again. I felt something different something firm and it moved it was very intriguing. I kept looking at her and without saying a word I couldn't move, I wanted to say something and I couldn't. She slowly put her arm around my waist and she slowly rub her crotch on my leg. I was frozen standing there looking at this gor... Continue»
Posted by ilgreek 6 months ago  |  Categories: First Time, Shemales, Taboo  |  
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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 2 years ago  |  Categories: Gay Male, Shemales  |  
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New Neighbors

My first attempt at writing one of these. Let me know what you think.

My roommate Mike burst into the room grinning, “Dude, have you seen the two girls that just moved in down the hall?” That caught my attention, “Wait, that blonde and brunette are moving onto our floor?” I had indeed seen them earlier outside the building. They had stood, laughing and chatting with one another, while movers unloaded boxes under their supervision. I couldn’t help but notice them; the blonde in a slightly too short summer dress that showed off her strong legs, and a low neck-line that promised never-ending ... Continue»
Posted by slatemhor 10 months ago  |  Categories: Anal, Hardcore, Shemales  |  
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Cheating Bastard

I began to suspect that my husband was cheating on me about 6 months ago. He'd call me and tell me he was working late or he'd show up to different events claiming that his boss needed him to finish a project before he could leave. Then his phone started to have more activity than normal. He'd often move to another room to take calls or messages. He started hiding his phone whenever he was asl**p so I couldn't go through it. The final clue came when he started to smell different. I had been married to him for many years so I knew his scent well but whenever we made love I could detect ano... Continue»
Posted by RyleighM72 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  
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Josie's Awakening

My name is Joseph, and this is a wonderful trip down memory lane for me. Join me as I relive the first few experiences of what would soon become a life changing event......


Jason and I were always best friends. We grew up together, we played sports together, we got laid at practically the same time by another pair of best friends, everything. This is our story......

I was out of town for a few weeks on business so we hadn’t had a chance to hang out for a while, so once I got back into town I called him up to see what he was up to
"Hey man what’s up"
"Nothin, my s****r is... Continue»
Posted by qqqqq2qq 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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Nate and his tranny neighbour

My first ever story. Depicting sex between a man and a transsexual.
It is lengthy but personally I enjoy these best. Constructive feedback is greatly appreciated, so feel free to write to me. Enjoy ; )

Nathan (Nate for short) was an average eighteen year old boy; liked girls, sports, partying, and being on his summer holidays he enjoyed the time off school. With some exceptions to the average rule, he loved his kinky dirty thoughts and porn. Frequently watching shemale porn, gorgeous busty women with big tits, a pretty female face but a thick juicy cock to be pleased, not a pussy to be fu... Continue»
Posted by BiTwinkxx 7 months ago  |  Categories: Anal, First Time, Shemales  |  
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Job Interview

I was interviewing for a new secretary and it had nearly reached the end of the day with no likely successful candidates. There was just one to go, a Keliana Kotey, whose CV certainly looked impressive and seemed as if she would do pretty well for the job, but I had to wait and see. The company’s receptionist, Paula, put her head around the office door to tell me that Miss Kotey was waiting and asked if she should show her in. I agreed and sat back to watch the view of Paula’s nice arse as she walked away from me. A twenty two year old gorgeous blonde, Paula was the kind of person who brighten... Continue»
Posted by keliana 4 years ago  |  Categories: Shemales  |  
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Am I A Bad Aunt - Part 4

Am I a Bad Aunt - Part Four

By billy69boy

(Part Three ended with Aunt Eve and her niece Ariel getting ready to pleasure each other with Ariel's favorite black strap-on.)

Ariel pleaded with me to fuck her first, such was her heightened state of arousal, as she regaled me with the details of her first sexual episode with Malcolm. After she helped me adjust the straps, she handed me the baby oil, and bent over the end of her bed, reaching back to spread her ass as best as she could with one hand. She was silent as I first lubed the thick black dildo, and then I dripped some down her... Continue»
Posted by billy69boy 1 year ago  |  Categories: Lesbian Sex, Shemales  |  
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Daddys little helper

Maybe if I'd minded my own business and stayed off my dad's computer, my life would have been a whole lot different. As it is I wouldn't change it for the world.

My name is George Mason Jr. I was twenty years old when I moved back in with my father (George Snr, obviously) after my mum left him and took up with some arse-wipe she met at her gym. He had been devastated by the betrayal and I had moved back in to keep him company and make sure he didn't do something stupid. I was quite a good cook and a bit of a neat freak, so it worked out okay for both of us. I got out of my shitty one bedroo... Continue»
Posted by sparkyking 1 year ago  |  Categories: Shemales, Taboo  |  
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Tranny orgy

You can live with someone and never really know them.
I was running a car wash in West Palm beach and every day I would take lunch at a cafe down the Blvd. The food was good, and cheap and I had the hots for Debbie, this built to the hilt redhead chick working there. She wasn't any great beauty but she had a body to die for. 36 DD tits. big hips and thick legs. Just my type. After a couple weeks I got the nerve to invite her to TGI Fridays for some drinks.
After a few, she started talking about her past. She was on parole from Ohio for cocaine trafficking. I found that interesting because a ... Continue»
Posted by kwhagie 1 month ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  
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crossdressing with my moms friend

Mom opened my bedroom door. she stood there in the doorway and stared at me obviously repulsed. after 10 or so seconds she closed the door and walked away.
i was mortified. i was kneeling on my bed, with her clothing catalogue open at the lingerie section laying on the bed before me, hard cock in hand. But most embarrasing.....i was wearing my mom's black bra, suspender belt and black stockings....her black panties were thrown onto the bedroom floor, cast aside when the urge to cum had become too much.

for weeks after this incident, we barely spoke. as it was just the two of us since Dad h... Continue»
Posted by hornyTVluvr 3 years ago  |  Categories: Fetish, First Time, Shemales  |  
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Turned Into A Sissy Boi

It started innocently enough. I was spending another weekend with my girlfriend and we were in bed late one Saturday night. She had just cum and I was rapidly on my way there. I was on top pumping in and out of her. She snaked her hand back and started lightly brushing her fingertips around my butt-hole. I let out one moan, then another, and on the third one, I shot my load inside her. It was one of the best orgasms of my life!
“Oh, you liked when I played around with your backdoor, huh?” she said a moment later with a teasing smile.
“I sure did! It was great!” I responded. Lookin... Continue»
Posted by subjaye 5 months ago  |  Categories: BDSM, Fetish, Shemales  |  
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He caught me in his wife's cloths

I do odd job's and I was about to do one for my wife's best friend Tina and her Husband Phillip. I went over and looked at the job. I told her it would take several days and that I could do the work while her and her husband were at work. That way I wouldn't be in anyones way. Well the first day of the job I showed up just before Tina left for work. Pillip was already gone. We chatted a while the she left for work. Tina is really very hot and I have wanted to fuck her for a long time. Sense i knew that was not going to happen I thought I would do the next best thing. I went stra... Continue»
Posted by firstknightd 5 years ago  |  Categories: Shemales  |  
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How I got started dressing

I was a sophomore in high school and like any teenage boy I was extremely horny. I masturbated atleast once a day usually 2 or even 3 times because I had so much time on my hands. I started off watching plain straight porn but I watched so much of it daily that I started to get bored of it. I just used sites like google or yahoo to find videos by typing in whatever I was into that day. It started out with just words like "blonde getting fucked" or "girlfriend giving blowjob." Once I started to get bored my words started to get more descriptive "Slut takes huge cock in ass."I was skimming throu... Continue»
Posted by pantyyboy 4 years ago  |  Categories: First Time, Masturbation, Shemales  |  
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I was bored one afternoon...

It was my day off. I was bored, and very horny. I can't help myself some days. Well, I thought to myself, I can either jerk off quickly or take a drive to one of the two adult stores with peep shows. It didn't take too long to decide.

I live in a very cold climate, and it was fairly cold out today, so as tempting as it was, I wasn't going to dress up in a cute skirt. I slipped into some tight jeans and looked at my profile in the mirror. I sure wish I had a better ass. Just a bit more of a 'bubble' would be nice. I put on a cute shirt and put a generic dark blue hoodie on. Dressed l... Continue»
Posted by zaria_ts 10 months ago  |  Categories: Shemales  |  
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