Shemales Porn Stories
Page 66

Tranny's First BBC

Sitting on the lounge at my local sex club I was watching the guys go by. You get to notice certain guys going past trying not to look like they are checking you out on the sly (and vice versa) thinking how they can approach me.

Normally it’s just the usual crowd of guys but several weeks ago a big muscular type African guy in his mid 30’s kept going past me and looking at me out of the corner of his eye. After about his third walk past I gave him a little smile. When I could see him coming down the hall the next time, I got up and slowly walked around the corner into the next hallway so he... Continue»
Posted by kbking64 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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My First Kiss

This is a story in progress so please be patient.

My name is Denise Babcock. I am a longtime transvestite having begun cross-dressing when I was 12. I began to have sex with other boys shortly thereafter. But it wasn't until I was 18 that I shared my first kiss with a boy. Paul had been one of my closest friends all through high school and we stayed friends even after graduation. Often when we hung out together complained to each other about our troubles with girls. One evening he called me up to go hang out at a bar with him. His girlfriend had recently dumped him and he was a bit depresse... Continue»
Posted by DeniseTV 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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First Time CD In Public

Just got back from a Adult Bookstore with an arcade. Prior to going I had decided to dress in garter belt and hose, short mini skirt, bra and panties, with a see thru top. Put my sweat pants and t-shirt on over it all. Walked out of the hotel and into the car. Drove into the parking lot there were only a few cars there. Went in and proceeded to the arcade. Found a booth went in and locked the door. Put the card into the machine and found a hot she-male video. Took my sweats and t-shirt off leaving me in my outfit.

I must say that my heart was pounding and could feel my head throbbing.... Continue»
Posted by Bobcat_139 2 years ago  |  Categories: First Time, Mature, Shemales  |  
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Bet You Didn't See That One Coming


I looked down at my cell phone. The two way talk ID popped up. I shuddered.
"Hey baby, come out, come out, wherever you are. Be prepared, cause when I find you; You're going to find out that life is a bitch.!"
My God! What the fuck was happening to me?---------- I've created some kind of a monster! It was just a little joke. It wasn't even mean. I don't do mean. But here I am on the run!
The cell buzzed again. "Come on my sweet. Trina wants to play."
Lord help me! I might not last through the night! I have to be calm. I have... Continue»
Posted by vosmou_vrot 1 year ago  |  Categories: Anal, Fetish, Shemales  |  
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T V times

I had an amazing experience a year ago when I was on here previously , I became friends with a sexy cross dresser called Dark Angel; we messaged each other and arranged too meet when my husband was away .. well to cut a long story short we ended up in bed together both in stockings and heels . I am on my back with my leggs wrapped around angel whilst she is fucking me on top. Because we were alone I had left the door open, suddenly I noticed my husband standing there watching . I thought he was going to explode but he put his finger to his lip as to be quiet . To my amazement he pulled out his... Continue»
Posted by tiger061 3 years ago  |  Categories: First Time, Mature, Shemales  |  
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My shemale boss part 3

I was woken by the vibrating noise of my mobile and looked over at the time, the bedside clock said 1am. The caller I'D on the phone simply showed Bitch, naimly my boss Miss Jones, would she never leave me alone.

I answered the phone and still being half asl**p simply said 'yes'.
'Don't answer me with that tone Rob' she said. 'Sorry, but its one in the morning' I replied.
'Be a darling Rob and pick me up from the club, text me when your outside'. Before I could say anything she hung up.

I pulled my arse out of bed, slipped on some tracky bottoms and a t-shirt, jumped in the car and dr... Continue»
Posted by big_rob49 2 years ago  |  Categories: Shemales  |  
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First Time pt 4 by trans_love (Fiction)

It’s been a while since this happened but I remember it like it was yesterday.


If you remember reading previous posts, I was a brand new teenager, about 5’2” around 110 lbs or so… green eyes, long brown hair, small b cup boobs (thanks to granma’s estrogen pills) and a VERY fem ass!! I’m a transsexual male to female. I had just been introduced to group sex at an adult book store by my ex bf’s dad, James. Not too long after my last story happened, James felt guilty about what happened and stopped wanting to see me. So there I was, lonely again. I had met up with Brian again and realized he... Continue»
Posted by 1superhornyguy 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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shes the boss

This story is 100% true well as true as I can remember. This year I celebrated 40 years of marriage. I am 60 and she is young 68. We met on a mini cruise from UK to Europe. I say cruise but it was just overnight boat trip to Denmark a day there and overnight trip back. I worked in a factory and it was a works trip there. There was about 40 of us going. I was 17 and just started work there. She was 24 didn't work in factory but her mum did. I hadn't had much luck with girls and was very inexperienced, she on other hand had 2 c***dren one age 8 and one aged 5. She had got pregnant when she wa... Continue»
Posted by tvtv11uk 11 months ago  |  Categories: Fetish, First Time, Shemales  |  
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Found out and Sissified by Wife Part II

After our first encounter Karen began buying me more frilly girly things and making me dress up for her. Pretty soon after that she started putting some makeup on me and bought me a blonde wig. I really liked the way I looked all made up in slutty clothes and heavy makeup and she did too. Then we would sit in front of the computer and we would watch porn together. It started with femdom stuff, with the girl fucking the guy with a strapon. Then pretty soon it graduated to CD porn, with sexy CDs sucking cock and getting fucked. Pretty soon after that it was just gay porn, usually guys sucking ea... Continue»
Posted by smilinwillie2001 3 months ago  |  Categories: Fetish, Shemales, Taboo  |  
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Late Night BJ

A few nights ago I was feeling horny and desperate for something to wrap my lips around. Flicking through the pages of various sex sites I found out there was a dogging spot close to where I lived, feeling a little nervous I decided to give it a go and see if my luck was in. I went to my 'slut' wardrobe and picked out a cute outfit I hoped would get me some action. I'm a tall slim mid 20's tgirl and get passes made all the time from men in the street and clubs, I have that innocent looking going on quite well! I decided on a short pretty pink flowery skirt, cute little fuck me strappy shoes an... Continue»
Posted by SluttyTgirl 3 years ago  |  Categories: Shemales  |  
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a very hot encounter

I've had been feeling way too horny for days; masturbating every night to shemale porn. I've always loved transexuals. There's nothing better than a very hot body with a fairly large cock to be sucked and drained of hot cum. There's something even kinkier for me about a top shemale. I imagine that cock being inside of me, drilling my little tight ass while I go crazy kissing whoever is fucking me.

The weekend arrived and that friday y decided I was not going to go out and just tend to my restaurant business. I have this little tradition that whenever I stay in at the restaurant on a weeken... Continue»
Posted by feinor11 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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Brad cant go back

It was a foggy evening in the Town. Brad was walking beside the road that lead to a truck stop. He couldn’t help but wonder how the hell everything happend so quickly. Brad was 19 year old boy who seemed to be an ordinary c***d of an ordinary f****y. He was a dark haired skinny boy and had a bit of a feminine features. He was currently in no school as he was not admitted to any since he didn’t do well on the tests. He was living with his mother, enjoying the carefree lifestyle of a student who didnt go to any school. He had friends but no girlfriend; he never had a girlfriend. Yes he seemed o... Continue»
Posted by vacantwhore 1 year ago  |  Categories: Gay Male, Shemales  |  
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my HEAVAN

This dream is for my super sex goddess mistress HEAVAN123 i worship the ground on wich she toers over me on ,i kneel at her feet waiting for her permission to show me wild devotion to her super temple of lust.
This is for you my goddess---

I am your son in this dream i am a short young man of only about four feet six inches tall,You being my mother on the other hand are a towering stacked wonder of nature standing a full eight feet tall your bust thrust out huge like two massive beach balls thrusting against any clothing you wear stretching your dress so tight they would swing & sway heavi... Continue»
Posted by huge_cock_rules 4 months ago  |  Categories: Fetish, Shemales, Taboo  |  
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My first Crossdresser - Part One

When she walked in to the restaurant I knew I was in trouble.

It was the end of three long days at the convention and I was tired. I had come down to the NASCAR Cafe for a sandwich, mainly because it was the only bar in the Sahara that didn't have video poker...I lose a lot of money playing video poker. Well there I am with my beer and sandwich, and I glance toward the entrance just as she's strutting toward a table.

Convincing she was not, a crossdresser without question. But pretty, really pretty. And the way she walked, shit, I was getting hard just watching her. She wore a tight bla... Continue»
Posted by abend 4 years ago  |  Categories: Fetish, First Time, Shemales  |  
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Satin Tranny Bride in the Sun-Part 2

A blushing bride I was not. I was all woman. I stood transfixed as I looked at myself. I was in awe of the creature I had created. I had feelings I'd never felt before. I was horny, yes my cock was rock hard but I felt more. It was pure lust. I had a hole and I wanted it filled. I wanted a man inside me. I needed a cock inside me to make me his and I needed it now.

I was aching.

I was snapped from my trans by my phone. It was 11 am and Phil was parked in my driveway. I thought I'd be nervous but I couldn't get started soon enough. But I had to be patient and work my plan so I could ple... Continue»
Posted by SatincdAus 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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HERMAPHRODITE BLACKMAIL

I remember it as though it were yesterday.
19 years old, jut dropped out of college over a sex scandal
with my History professor.
I managed to find a good job in a high end boutique
because I was beautiful, sexy and could pass myself off
as classy, even though I was a cheap whore.
My boss was a perverted dominatrix and immediately
made me her plaything as a condition for my employment.
As long as I obeyed her and serviced her clients.
I was making very good money as a prostitute for rich perverts.
I found a fairly nice apartment, no penthouse for sure
but far from a dump.
I del
... Continue»
Posted by Utubeslut 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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16 ladyboys jerked off in front of me! live!

Just got back from Thailand and had a very special birthday present. A big party had been arranged for me at my favorite ladyboy bar and a “competition” had been secretly arranged for me.

Had a nice party with balloons, food, drinks etc then a midnight I was told that it was now time for my birthday present. The door to the bar was closed a chair was bought out and put against the closed door and I was told to go sit on it. Then I was blindfolded and a bib put on me. I could hear all the ladyboys giggling and moving about.

The blindfold was removed and I was greeted with the site of ... Continue»
Posted by toniparr 3 years ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  
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The Mechanic

My name is Bruce, I am one of those mobile mechanic chaps you call out when something goes wrong with your car. You get to meet a nice variety of people, some good some not so, with some very good looking ladies thrown in as well, which make it nice. A lot of the clientele are people you see a couple of times a year for a car service so you get to know some of them quite well.

I hadn’t had that much in the way of action for a long time. I had split with my wife a few years before and now I always seemed to be working. Anyway it’s not the most attractive of looks when you hands are covered ... Continue»
Posted by domestique01 3 years ago  |  Categories: Shemales  |  
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More adventures with my Roommate

It was Saturday evening and I was dressed in my "maid sissy outfit" waiting for my roommate, Ed, to come home. I heard the sound of two male voices talking loudly outside the front door of our apartment. One voice was the unmistakable booming voice of Ed and I didn't know who the other voice was. The door opened and in walked Ed and another guy. Ed introduced us, he said, "Baby, this is Robert. Robert, this is Baby." Robert smiled and said hello to me as he leered at my stocking clad legs. Robert was quite different from Ed and I wondered about their friendship. Robert was in his late 5... Continue»
Posted by rikki50 2 years ago  |  Categories: Gay Male, Shemales  |  
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Tgirl Hooker pt6

All my stories are from my experiences

If you have not read any of my Tgirl Hooker stories, I would advise you do as they will help set the story and you will read, she was no longer a hooker to me but more of a fuck buddy.

You may recall from my last story that the time before we met I was still bruised inside from the pounding my ass had taken from her monster cock. I loved the feel of Emma inside me and she had promised the next time she fucked me it would be a completely different experience.. and so it was!

I received a text from Emma "Hey Hun, fancy dinner tonight at mine? promi... Continue»
Posted by dirtydisco99 8 months ago  |  Categories: Anal, Fetish, Shemales  |  
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