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Shemales Porn Stories

Friends with benefits Part TWO (Edith)

FetishSex HumorShemales

this is the second part of my fantasy.... It took me about 3 minutes to decide what matching set I was going to wear for the night out with my friend. I found a very sexy Simone Pêrele satin demi bra with its matching thong, that was my choice, I turned around to my friend which was in her "born suit" and "I CHOOSE THIS ONE... you sexy bitch!" She gave me the ok look, "lets get dress first and then I am going to put you make up, I have couple of ideas, do you mine if I take pictures.....hahahahah whom I am k**ding, I am going to take tons of pictures, my sexy friend. I… Read more

Posted by ilialenyc 1 year ago 2 1,864 100%

Friends with benefits, part ONE (Edith)

FetishSex HumorShemales

This is a fictional story. My cell rang with a familiar melody, I picked it up and looked at the screen. It was my friend Edith. I answer it and her voice on the other end said, "do yo want pizza and a fuck?" I just giggle, "damn woman...." Then she interrupted me... "what don't you like pizza???" She cracked up... "Hey I am in the neighborhood, mind if I stop by?" Edith said. "No worries, bring some beer, real beer, no Coronas." "Ok, will be there in a few." This woman has been my friend… Read more

Posted by ilialenyc 1 year ago 6 2,532 80%

Cockatoo Part 1

First TimeLesbian SexShemales

Cockatoo Nikkie Silk It’s a cliché, isn’t it? Man comes home early and finds his wife in bed with someone else. Only slightly less of a cliché in my case, as the ‘someone else’ was my wife’s closest girlfriend - closest in every sense of the word. It was a quick divorce; no k**s, only a rented flat, so the only squabbles were about books and cds. In the end I told her to keep the lot. I wanted to make it a clean break. I managed to fit all I owned into the boot of my small car. I was 28 years old, fit, healthy and with a good but frankly boring job in a software company j… Read more

Posted by nikkiesilk 1 year ago 3 3,232 100%

Me and myself


It was a sunny day sun shining birds singing so i thought to myself im guna make the best of today. With that i dressed up in my silky panties under my normal clothing and went on my way, i was going for a walk down the river bank it was beautiful on a summers day even better when i was feeling horny and slutty! As i got further away from public i slowly kept taking items of clothing off one by one as strutted more slutty like now wiggling my little ass i did this till all was left was me in my black bra and panties, mmmh i looked down at myself and got a shiver you sexy bitch i thought!… Read more

Posted by missycd23 1 year ago 1,497 86%

Tranny Surprise Part 1


After being cheated on for months here I am alone in a bar having a drink. I dont understand whats wrong with me im above average in looks, im fit, im successful for my age. Its time I move on though and so far no girls ive dated have been worth a second date. As I look around the bar I see her. I immediately start to stare. Looks like she was there with a couple of her friends. I order another beer and decide to scope it out for a little bit. I just couldnt get over how pretty she was. She was tall, thin, and had the cutest smil… Read more

Posted by Entities 1 year ago 13 10,161 91%

Hypno whore at camp.

Gay MaleShemalesTaboo

At 1pm Bob picked me up right on time. I came out with a big duffle bag of stuff and threw it in the back seat as I climbed in. "Did you get everything?" he asked with a big smile. I shrugged shook my head "Tooth brush, tooth paste, shoes, socks, underwear, pants and shirts." "Cool, let's go." he said still smiling I looked at him closely "Why you so happy?" He chuckled "I just cant wait to get there." And pulled out. He was really smirking because he knew what I had in the bag. I thought I had packed what I told him. What I really packed was T-brush and paste, makeup, wig, panties,… Read more

Posted by bfer13 1 year ago 10 4,237 89%

A Very New Year

First TimeShemales

Sometimes things happen unexpectedly. Those words describe my entire New Year's Eve. My night started with me downtown. Now ordinarily I wouldn't step foot downtown on New Year's Eve if I could at all avoid it. The place becomes a zoo of d***ken bafoons and desperate revelers. But through an unfortunate series of events I found myself behind virtual enemies lines too late into the day this New Year's Eve. Many of the roads had already been blocked off and those that weren't were highly congested with the other like minded people that would give anything to be out of here before things got too… Read more

Posted by rhyze 1 year ago 2 1,429 100%

Tranny Motel

Gay MaleInterracial SexShemales

Tyrone and Kimberly Woods kissed as all of the guests at their house party cheered them on. It was their first anniversary and they were celebrating this night with f****y and friends. There were close to forty people in attendance – most of whom had brought some form of alcohol and all of whom had brought a gift. There was great music and excellent barbecue as Kimberly’s dad and Tyrone’s uncle manned the grill. Folks were laughing, dancing, and having a great time. In one corner of the yard, there was a game of dominoes transpiring. Next to it, a foursome was playing Spades. Several minute… Read more

Posted by faggyboi 1 year ago 2 3,136 100%

Big Booty Femme Gets Bossed

AnalGay MaleShemales

“What’s up, Unc,” the thirty-one year old, dark-skinned brotha said into his phone. “You still wanna meet at the diner at nine o’clock,” inquired the man’s mother’s b*****r. “Yeah. I’ll be there at nine. I just gotta make a quick stop to drop off some tools at a friend’s house and I’ll be right over.” “Alright. See you then.” Hadrian Woods walked out of his one-bedroom apartment and started his fire red 2013 GMC Sierra 1500 pickup truck by remote. He drove slowly out of the gated community. It was a bit past 8:00 a.m. He turned right out of the complex. The music playing from his iTunes… Read more

Posted by faggyboi 1 year ago 1 4,105 92%

A Reluctant Gang Bang

Group SexInterracial SexShemales

byTonyaTV69© This story was stolen and posted here by a LIAR claiming it was theirs but I am the real author and they were just a cheap barely literate FAKE!!! Hi all! I have been cross dressing and playing with men for many years now. One of My first experiences was being gang fucked by about 9 guys at an adult arcade. I was 18 at the time and it kind of traumatized me as it was pretty much a gang **** at an adult arcade. I was dressed up in a white flowered sundress panty hose and white strap on high heeled sandals all borrowed from my older s****r. I had my make up done up just ri… Read more

Posted by Tonyatv69 1 year ago 13 7,400 100%


BDSMGay MaleShemales

Daddy at the Truckstop - 4 The van didn't have many windows, but there wasn't a lot to see anyway where I was. Tucked neatly in a cage, my wrists and ankles were chained to the bars, and a ring gag kept my mouth open, at first drooling a bit, but over time my mouth started to become dry. The vibrating plug in my asspussy didn't slow at all. I could feel the bumps of the concrete as Daddy sped down the freeway, and I had no way of knowing how far he was taking me from the truckstop. Was it 30 minutes? 45? It was hard to say. At first I was filled with shame and fear after Daddy made m… Read more

Posted by StaceyDeprave 1 year ago 1 3,725 100%

Exiting second time

AnalGroup SexShemales

After the first time had already passed, I decided to take some time as my ass still hurt a few days after my encounter. The guy I used to talk still had not sent me any message a 2 weeks after the events of the previous story so I decided to do something. After the pain went away I noticed I coul very easily play with my ass and I would not hurt at all! I went to the point that I could fist myself and it would rarely hurt.I played putting things in my ass and it felt awesome. I decided I was 100% bi and wanted to try something new, so I began crossdressing more seriously. I went to swimming l… Read more

Posted by Ktm999 1 year ago 4 2,113 88%

The Biograph Cinema

First TimeMatureShemales

I visited the Biograph Cinema in Victoria London in the 70’s as a fairly naïve teenager, who ended up m*****ed. Shame the place closed, I was enjoying being fiddled with by dirty old men. The Biograph was clearly the haunt of the Dirty Mac Brigade, and all of those sorts of men my Mother had told me to watch out for. Aged 18 I’d never even kissed a girl let alone had someone else make me cum. So, I was drawn back to the place. Like any teenager I wanked at least daily, but the previous episodes had become my favourite wanking material and I just had to go back for more. A week after m… Read more

Posted by Vikkinylons 1 year ago 10 2,030 100%

The secret exchange (Sarah)


"Your wife told me you were a crossdresser 12 years ago, still doing it?" Sarah asked me. Very calm, I sip my coffee and answer, "Yes." This is how this story got to this point. Sarah has been friend with my wife for about 14 years, out of college they met in the bank they both used to work. They became very good friends. Thirteen years ago I met my wife, she did not know about Iliana, back then I was just trying to be myself with my then girlfriend and one day I decided to let her know about my closet life style. To my surprised she reacted very well, she asked tons of questions… Read more

Posted by ilialenyc 1 year ago 4 3,037 100%

Swimming with a larg man.


More of my diaries. Sorry it takes long time for this one to come. I was very busy. I was in 13 and I nearly grown up my body was like a girl big boot and breast. My father was sl**ping with me nearly every night. I had a lots of sexy clothes my father bought for me . In school I still was a boy and I needed to wear very big school wear to other guys don't see my boobs. Last few years I changed my school few times because when some one realised about me, my father very quickly change my school to avoid trouble. I get to use to have a double life. I kind of like it. I was going to… Read more

Posted by Echoes90 1 year ago 2 5,980 70%

sl**ping With The Enemy

Gay MaleShemales

sl**ping With The Enemy The present day… The wedding party was in full swing now and I anxiously scanned the guests to see if everybody was enjoying themselves. The noise levels had risen in line with the amount of drink being consumed, so I guess that was a good enough proxy for enjoyment. I was holding a glass of champagne in my perfectly manicured fingers and as I took a sip I caught the eye of my new husband who had been buttonholed by two of my aged relatives. His eyes pleaded at me to rescue him but I simply grinned and raised my glass to him; I would leave him there for a while to t… Read more

Posted by nikkiesilk 1 year ago 17 8,524 94%

I slept with a porn star


This is a true story. I left out her name but if you need to know message me. I was on Tinder late Wednesday night. I'd gotten home from a first date with a very attractive woman with absolutely no spark I knew there wouldn't be a second date and that was fine. Laying on the couch, flipping through the profiles, I swiped right on a very attractive younger woman. I didn't look at her profile and moved on. A couple minutes later I got a notification that she swiped right on me. So, I figured I'd check out her full profile this time and saw she was transgendered. That was fine - I'm pansexual.… Read more

Posted by artbasel 1 year ago 6 11,880 90%



They didn’t need to advertise the job for Santa’s helper. I already offered my services. Since I was fairly popular and I could provide my own costume, a skintight green catsuit, my copper wig and boots, my supervisor went for it. I must admit that my main motivation was that I would be paid to wear a skintight costume, and hopefully get a few curious glances at my ass and body in the shimmery material! The Santa for the job was some retired security guard called Alfred who used to work at our store, who a few times I served pantyhose to in the pretext that they were for his wife. In fact… Read more

Posted by leotardlust 1 year ago 2 3,394 90%

Busted Wearing Panties Ch. 04


Tranny – bisexual – bdsm – nipple play – anal – first time Chris and Jessica had to leave for a dinner engagement which they could not get out of. Emily and I we wanted to be alone anyway so we were glad. Jessica and Chris weren't even out of the driveway before I slipped behind Emily, reached my arms around her chest tweaking her nipples, and then I started rubbing my cockhead between her cheeks. "MMMMM! That feels nice. I'm going to clean the kitchen up a bit. You grab the towels outside and put them in the laundry. I will meet you in the bedroom in five minutes." I ran out t… Read more

Posted by naughty_bi_interest 1 year ago 6 2,848 93%

Peaches And Cream #1

First TimeFetishShemales

Prositutes – lingerie – hookers – transsexual first time – butt plugs I have a little problem. Well, to be honest, it's more than just a little problem. Some might consider it to be a huge problem. I am addicted to prostitutes. I have been pretty much all of my adult life, since I first walked out of the front gate at Lackland Air f***e Base in Texas and saw a pretty young girl sitting on the hood of a car in front of a massage parlor. When I glanced over at her she had slipped her shorts aside and exposed her hairy vagina, and I had followed her into the massage parlor and… Read more

Posted by naughty_bi_interest 1 year ago 3 2,761 90%