Shemales Porn Stories
Page 74

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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My Fantasy Meet

So what is my fantasy...well I suppose that being on this site is a bit of a fantasy in a way as I’m basically a straight guy who has become more and more turned on with the idea of wearing lingerie...then discovering this site accelerated the process and has made me more and more curious to actually meet another dresser like myself...I’ve also had plenty of hot times masturbating on c2c on here too and in doing so have graduated from wearing panties to stockings and now lipgloss, wigs, slips, pearls and heels...so I think that I am so ready to take the final step and actually arrange a meet.
... Continue»
Posted by Michelle62tv 2 months ago  |  Categories: Shemales  |  Views: 1177  |  
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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 3 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: 1176  |  
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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: 1174  |  
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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: 1174  |  
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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 2 years 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 1 year ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 1171  |  
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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 4 years ago  |  Categories: Shemales  |  Views: 1171  |  
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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 3 years ago  |  Categories: Gay Male, Shemales  |  Views: 1166  |  
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Relationship Counseling

“It’s been so long since I had your mouth on my dick,” crowed five-foot-nine-inch, medium build caramel-skinned brotha as he pushed down on the head of the sissy cock sucker.
“You like it,” mumbled the thirty year-old big booty flame.
“Yeah,” he replied pushing the faggot back down his eight inch tool. “You ready to feel it in your ass?”
“Mmhmm,” Jayshawn Terry.

The five-foot-ten-inch, one-hundred-seventy-pound host stood up and grabbed his admirer’s hand. He led the guest down the hallway to sole bedroom in his apartment. He hopped onto the bed and began gyrating his ample, fleshy derri... Continue»
Posted by faggyboi 1 month ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1169  |  
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The Lion, The Bitch, and the fucking Wardrobe.

I guess I have always been a sissy. I started crossdressing at a young age and it gave me such a wonderful feeling that I struggle to form the correct words to describe the way it makes me feel. It just felt right, and ohh so sexy! Like I said, I have always been sort of a sissy, and my father couldn't have been less plesed. I think he had his suspicions that I might be, uhhh... different before he found my lingerie and stilleto shoes, but once he knew for sure thats the first time he hit me. He made me promise, at pain of... pain, that I would never do any of "that faggot shit" again.
... Continue»
Posted by redk1 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1165  |  
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Joe, Chrissie and, Paula

) I don’t know why I need to get all dressed up, it’s you he’s coming to see.
I know, but I like to see you looking sexy and I’m sure Joe appreciates having a sexy woman watching.
Anyway, you finish off and I’ll make sure dinner is OK.
It would be the second time Paula had met Joe, the first time she was only there to take photos, not taking any part in proceedings.

How does that look Paula?
Yes, you look good, very tarty though, I can see your stocking tops
I know, but he likes me like this. Oh,Oh, that’s him now. Will you go?

Paula lets Joe in, greets him with a kiss and when he ... Continue»
Posted by chrissie28 4 months ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1165  |  
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My girlie fantasy part 2

A few days passed since my heavenly Halloween night with the wondrous morning after & I was so excited at the possibility of meeting up with the stud that took me like a woman again. Since I knew Halloween wasn't for another year I invested in a new outfit so to meet him in. I returned to the bar one week afterwards but he never showed, though several men hit on me I never entertained them at all. The bartender wasn't the same so I never asked if they knew my hunk or not. Disappointed I went home but was motivated to keep trying. Realizing I only had one new outfit I went shopping the ne... Continue»
Posted by multiplierx 2 months ago  |  Categories: Anal, Fetish, Shemales  |  Views: 1164  |  
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Working late

This story follows on from my last story “On the Road”

Working Late.

Dannielle had been woken by a call from Paul asking her to come into work early as they had some figures to go over. She knew what that meant, a quick fuck before work. As she was getting ready she remembered what those builders had said yesterday, the photos they had taken and the note they had left. “Wonder if they where actually going to come to her work and find her if she did’t get in touch” she thought as she got ready. It wouldn’t be that bad, she had fun with them and she loved Johns cock. “Bet they where just p... Continue»
Posted by danni1 4 years ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1164  |  
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A Walk after a Busted Date part 2 OR My First Day

A Walk after a Busted Date part 2 OR My First Day as a Hooker part 2

Toot-toot!

Crap that scared me! I wasn't expecting anyone to try to pick me up again. I thought it would have been a fluke. A one-off earlier with the k** and the handjob. Really?

Again? I can't say that I'm not flattered. I was, really. Gathering my nerves before turning to see who my next suitor was, I slowly turned without my legs shaking so much this time. Whomever was in the car, they would see me as fairly confident hooker walking the street.

Leaning on the passenger door of the Lincoln gave me a vie... Continue»
Posted by LeslieStone 1 year ago  |  Categories: First Time, Hardcore, Shemales  |  Views: 1162  |  
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A Different Kind of Woman pt2

My hands were at one and eleven o'clock tied to the bed, the beautiful creature that I was so infatuated with turned out to be a shemale and I was at her/his mercy. Tiffany was working her/his penis up my butt with precision all the while stroking my penis keeping me rigid hard. Each time I thought I was about to shoot Tiffany would stop long enough for me to calm down.
Tiffany had called some body named 'Joliet' and told her(?) to bring 'Bambi' with her(?). Tiffany was having her/his self a fantasy come true pumping her/his penis deep into my butt, all I could do was grunt and groan with... Continue»
Posted by d4david 3 years ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1161  |  
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A Sissy Slave for a Transvestite...continuation

Gwen took hold of my head and guided her penis to my lips and pressed her pre-cum oozing head against them. Gwen said tenderly, almost panting '...come now open those lips and let me in, we both are going to enjoy this...' Helpless and at her mercy, I opened my lips and allowed Gwen to slide her monstrous penile head and shaft into my oral cavity. Gwendolyn slid her penis into my mouth, her legs started to trembled as she gasp and took short quick breaths. She pulled her penis back slowly till only the head was still behind my teeth.

Gwendolyn gasp saying '...oh baby, yes that's just what... Continue»
Posted by d4david 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 1161  |  
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My First TV Cottaging Fun

My first time (And this is Genuine, I assure you)

I dressed under my normal clothes and took a rucksack with other bit's & pieces in and went to a nearby "Cottage" that had 2 Glory Holes, when I got there, it was empty, so I went in the middle cubicle, finished dressing: Stockings & Suspenders, High Heeled Lace up PVC Boots, PVC Basque etc.

I didn't have to wait long, the cubicle's then got occupied either side, through the peep holes in the door, I could see at least 2 other guys at the urinals.

Then I saw fingers appearing at the hole to my left, I looked through the hole on my rig... Continue»
Posted by uktvmaid 1 year ago  |  Categories: Group Sex, Mature, Shemales  |  Views: 1159  |  
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made me a slut.

I spent my time online since I was 18 watching tranny porn and crossdresser porn I really enjoy a mix of both especially with a big black cock in between I found a movie with a ebony tranny with a big cock and a white sissy gurl with a nice sized cock also... They got dolled up together and all of a sudden they were smearing each others make up on each others cocks... The things I saw that happened to that sissy was some of the hottest things I have ever seen... After this video I couldn't just go back to regular porn or continue searching online to watch videos, none matched up... So I starte... Continue»
Posted by reefermcrevolver 3 years ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  Views: 1152  |  
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