Shemales Porn Stories
Page 65

From Andy to Amy


Story codes: CD TV mf voy mast nosex

If you are looking for serious one handed reading, then you are in the wrong place. I hpe you like this. It's the stopry of a young man's first venture into cross dressing. Any similarity to me is entirely coincidental!

Title: Andy to Amy

"Why are you staring at my knickers?"

I jerked upright. God, I really had been staring at her knickers - not the ones she was wearing, sadly, but a pair on the floor, presumably yesterday's pair. They were perfectly normal white knickers with little pink flowers on them and a tiny satin bow on the front - ... Continue»
Posted by justpeekinout 2 years ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 1184  |  
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PantyBoy Gets A Reaming

I love to get really in touch with my feminine side. I get so turned on when I watch a man look my body up and down while I'm wearing some really sexy lingerie. I feel so naughty and slutty, knowing that I am going to let him do anything and everything he wants to me!! I was chatting in a room on one of the big websites when an IM from a guy in my area came across my screen. He wasted no time telling me how he liked my pictures that I had posted and how horny they had made him. I told him that flattery would get him everything, and he immediately invited me to his place. I don't usually meet i... Continue»
Posted by LRock4fun 2 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 1183  |  
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A good friend

I have a friend whos name is Novak.We have known each other since we were little k**s.We have always done everything together and have no secrets.But he didnt know that i liked to wear womens clothes.He has blue eyes,is very handsome and is very developed and he also plays football.Since we were really good friends i saw his dick several times and it was nice and big. Sometimes i dreamed i sucked it and that he came on my face.
One day we came to my place after a night out in town and he was d***k,so i decided to try to seduce him. He sat on the sofa in the leaving room while i was changing i... Continue»
Posted by nikoletakurva 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 1181  |  
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shemale fantasy - i've read before and dream

I repair computers, often "on site"--in people's homes. I got a call from a woman asking me to come to her house to fix her PC. She told me her name was Shandra. We made arrangements for me to show up there Saturday afternoon.

I showed up at the appointed time and was surprised when I saw her--she was taller than I am (I'm 5'11", she had to be at least 6'2") and fairly stocky. She looked like she could kick my ass in a wrestling match, but had an unmistakable femininity.

Her hair was dirty blond and loosely curled, and her face was quite beautiful. She was wearing makeup, but it was und... Continue»
Posted by shikzaid 1 year ago  |  Categories: Shemales  |  Views: 1179  |  
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My first TS (Part 1)

I know most of these stories are often full of cliches and often I debate how true they actually are. So now that I have experienced one for myself, I thought I would give this a shot.

So, after spending the last few months planning and searching for ways to put my ultimate fantasy to the test: to meet and f*** a TS/ crossdresser, last week the dream finally became a reality. The person in question was a tall, pale TS called Chantelle and whilst she lived down in London, it was a trip I had to make. HAving shared pics and steamy chats, the time had finally come to meet up and act out what w... Continue»
Posted by geoff_lovemachine 2 years ago  |  Categories: Shemales  |  Views: 1176  |  
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Night out

My wife knew that I liked to dress and would often help me. Usually it just consisted of dressing up and watching TV or maybe having hot sex. Once she had me dress and took me for a drive to the park where she made me walk around and pose for pictures. She’d also take me to the local thrift stores where we’d buy new things for Michelle. In bed we’d often talk about me dressing up and going someplace in public like a club or show. It seemed to make us both hot and the sex we had afterwards was fantastic.
One weekend we had to go to Providence for a friends wedding. My wife told me she w... Continue»
Posted by MichelleSEmass 2 years ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1175  |  
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nigger's white sissy boy


I started jerking off to ejaculation when I was around 18. Once I started doing it, it was all I thought about, 27/7 it seemed like. I collected fuck mags and porno tapes wherever I could find them, to use as visual aids. Just looking at those sexy nude women being loved up by their hot men made my dick so fuckin' HARD! Because of that I was able to convince myself that I was normal, of course, in retrospect it is obvious that I was identifying with the women.

One day when my mom was at work, I was laying in her bed, masturbating. I got up and rummaged through her underwear drawer. The dr... Continue»
Posted by nicoleinberlin 1 year ago  |  Categories: Interracial Sex, Shemales  |  Views: 1175  |  
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Little cock convention

Little Cock convention

They came from all over the nation to downtown LA convention center. It was the "Little Cock Convention" I watched as men from all races and status came in. Sometimes they came with their wives,friends,Mistresses,lovers, or even their boyfriends. I was on Guard duty and
walking the convention hall. Looking at the cuckold porn, sheepish looking bulls up on the Auction block, Penis extenders,pumps, and all the other crap that came with this convention. I looked at some over eager wives and husbands pawing at some "bulls" and walked over "Ex... Continue»
Posted by sinfultictac 4 years ago  |  Categories: Hardcore, Sex Humor, Shemales  |  Views: 1173  |  
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My Frist time with a tranny

My Frist time it was back when AOL frist came out. I was in a miami chatroom and I met a tranylicous. We Started to chat. I remember going to the profile on the side of the message window and I found out throu pics what a tranny was. I must of been 13 at the time or so. She gave me her address. it was not to far from Downtown so I head over to meet her as I smoked a joint. She had a nice apt, pretty empty She had just moved from Ny. After a little chat we had that helped me relax She came closer to me and we started to Kiss. I felt my bl**d rush threw my body I could feel my ear tingle. She w... Continue»
Posted by lucifer696 2 years ago  |  Categories: First Time, Shemales  |  Views: 1173  |  
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#2 - Nikki Gets Satisfied

It was about a week later and I had heard very little from the guy I had met up with. I thought he wasnt interested and was actually thinking about deleting him from my phone when he txt one morning to tell me he was going to be free during that day if I was free and that this time he had condoms. I took a while to think about it and told him he could come over to mine and we could have fun from where we left off last time. He seemed very pleased by this and requested what he wanted me to wear if I had it so I teased a little and told him that he will find out when he gets here to what im wear... Continue»
Posted by Nikki_93 2 years ago  |  Categories: Anal, Shemales  |  Views: 1173  |  
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Fantasy fuck

Sitting in the toilet cubicle I have been horny all day my cock is semi hard and I run my finger over the eye as pre cum oozes from the slit, I taste it's salty flavour as I strain the p*o out mmm wish there was something going in rather than out! There is activity in the next stall and I see some flesh through the gloryhole as someone sits down, with my cock stiffer than ever and my heart beating I look through to see a beautiful tranny pull her satin panties down and strOke her cock her fingers wiggle at the hole as a invitation, so I go for it and place my erectiOn through the hole , wow ho... Continue»
Posted by kawa696969 1 year ago  |  Categories: Anal, Shemales  |  Views: 1173  |  
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Rendezvous with Cheryl

Pulling up to the motel my cock was already rock hard just thinking about Cheryl. It had been a few months since my last trip to Baltimore and I so wanted her. We had met on craigslist about a year ago and rendezvous a few times. Now it is kind of a regular thing whenever I am traveling through. Cheryl always grabs a room at this seedy super 8 and then text me the room number. Cheryl looked so sexy today she had dark brown shoulder length hair that curled at the end, nicely lined eyebrows, long and dark eyelashes, her cute cheeks glowed matching her light pink lips. Two long earrings dangled f... Continue»
Posted by iheartm2f 7 months ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 1172  |  
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Michelle's Big surprise repost

My Surprise Encounter
This story is fiction and did not really happen and was only a dream

Hello My name is Michelle I live in upstate New York.
I am a 42 year old Female and ,I am Bi-Sexual which means to some of you that don't know that means I like Women and Men. I am 5'9 160 brown hair and brown eyes with 40 DD breasts. I am half Dominican and half Irish.
Well any way here is what happened in My dream last night.
I started out like any other night seriously boring. So I talked My boyfriend Mark into going out to eat At My favorite ... Continue»
Posted by dirtylatina4u 6 months ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 1172  |  
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Dirty Tranny gang bang

Deep breath Charlotte, step into the night air and strut your stuff girl.

This is what I was born to do; I snuggle into my short white fleecy coat as my 5” platform heels click on the pavement. Glancing down I can see my shapely stocking clad legs and, the all important, ankle bracelet glitter in the light reflected from the street lamps.

It is not quite 8 pm as I walk the short distance from my hotel to the pre-arranged meeting place just outside the pub near Tower Bridge.

Two men walk past; mid thirties and well dressed, they have both been looking at me for some time,... Continue»
Posted by charlottekerscot 2 years ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1171  |  
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transvestite in trouble 4 - the internet porn quee

Bright light filled the room, waking me from my unconciousness.

so bright it took a while for my eyes to focus. When they did the first site i saw was myself, in the wall sized mirror opposite me, strapped to the chair. It was me only now i had masses of long blode hair, tied up in 2 pigtails, loads of black eye make up and long false eyelashes, and big bright red lips. A new ball gag in my mouth, I was wearing a pink latex basque, white stockings and red slutty shoes, 6" heel with a 2" platform. I had on no panties, my cock was now locked in a heavy, metal chrome device, and there was som... Continue»
Posted by hornyTVluvr 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1170  |  
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Young Sissy Ch. 01

Author's Note: This is a follow up to The Young Master series. You can start here if you aren't interested in Belle's misadventures as spoiled young man turned out by his own sissy slave and eventually enslaved by his step-father, but it does introduce a lot of characters you'll read about in this series.

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I don't know how long I was under...days, weeks...who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck with needles, filling me with horribly persuasive dreams of a beautiful new body. I tried to imagine myself as a... Continue»
Posted by bi_hengst 3 months ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 1173  |  
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unnecessary roughness

Some years back, I was on an overnight business trip. I would often crossdress in my motel room to entertain myself and practice looking sexy. I could pass as a real woman from a distance but not so much up close. I'd been strutting around in a short a****l print dress and platform heels, admiring myself in the mirror and occasionally walking around outside my room in the motel parking lot. There was a convenience store/gas station next to the motel, and I kept walking over toward it, daring to be seen by people filling their tanks, etc. Late that night I decided that I just had to go over to ... Continue»
Posted by dana213 2 years ago  |  Categories: Gay Male, Shemales  |  Views: 1165  |  
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She wanted to Watch!

Everyone knows I'm bi and a Transvestite. I don't dress as much as I wish but I do go out two or three times a week. When I'm not dressed up I tend to hang at a straight redneck bar thats about two blocks from my house. They all know both mark and Kristy there and most are nice to me and respect me because of the respect I give to them.

Well yesterday I was in after work for a couple beers and Cindy the bartender and Lisa wanted me to do some drinks with them. Orange Crushes, wow I didn't want to get d***k cause I had plans for Kristy to go out clubbing. But after encou... Continue»
Posted by kristygurl 3 years ago  |  Categories: Shemales  |  Views: 1168  |  
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My imagination was becoming equal to reality

After the tour , which by the way was really great , I sat down facing the bed that stood where a maid was busy spoiling . Someone down on a bench There were several people watching and suddenly I felt something against me arm. I had no idea that there was a glory hole , apparently I was sitting . A good spot It put a nice big cock from the glory hole . I’m going to suck it nice and himself was there even hornier from . Someone came to stand that was nice to ‘ t play with his cock . Now I had two splendid. I continued with particular hand at the 1st and took 2nd in my mouth . I was able to tak... Continue»
Posted by nathalie-daniels 22 days ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 1164  |  
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Five year plan

Five year plan

After many years you find yourself falling into a routine five years had passed and out of those 1826 days I had spent only 2 ½ Days out of chastity less than 1 hour a month when you are locked up for so long frustration takes on a whole new meaning simple tasks become a nightmare because you can’t stop thinking about tits cocks ass and pussy so Mistress Isabella gave me a task that took me a long time to perfect my task was to have a full orgasm in chastity and this is how it started.
My normal routine would start in the morning get washed dressed put my face on go down on... Continue»
Posted by Sissy_Kara 4 days ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1170  |  
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