Shemales Porn Stories
Page 81

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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Playtime Stories Ch 1.

1.

I am such a slut.
I was soft a few minutes ago after cumming hard, but now as I drive to my motel I’m getting hard again. I keep pulling my cock out of the side of my panties and rubbing the sticky head as I remember the man behind me gripping my hips and pumping my ass. Precum lubes my thumb work. My ass is a little sore and leaking lube after a hot slow fuck from an older Hispanic man who was a little too gentlemanly and a bit too small for my tastes. I fixed my makeup but I should have done a better job with my thick auburn wig. Although I just came and I got fucked like I w... Continue»
Posted by 6988slutty_rbckyy 1 year ago  |  Categories: Gay Male, Hardcore, Shemales  |  
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Tgirl fun

Because it was a little cold I went out dressed in a nice pair of tailored jeans, which show of my bum beautifully, black bra, lacy top and a really tarty shimmering jacket. I was wearing a lovely pair of ankle boots and was able to quickly slip out the front door of my house and into my car. It felt wonderful to be dressed up and driving through the rainy streets. People were able to look at me when I stopped at traffic lights but no one seemed to notice anything amiss. I wasn't able to park too close to Mandy's flat so had a longish walk before I got to her front door. I loved the sound of m... Continue»
Posted by TaniaHarvey 5 years ago  |  Categories: Anal, Shemales  |  
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Transsexual Son Daughter

Now I’m a 51 year old mother of one and watching my Daughter who’d been once my son putting on that very nice silk blue bra from Harrods department store and lift up her huge breast in to them made me so wet. Now seeing my son all now transformed and transitioned in to a beautiful woman but she’d still had got her manly bits now that didn’t harm anyone but boy did she look awesome and lovely all 5’9 of her slim size 10 with her rather large 46DDs which shed always wanted and her slim lines like a guy would say about a classic sports car.

Now as I was saying I am a 51yr with a son that had b... Continue»
Posted by 1superhornyguy 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 2 years ago  |  Categories: Anal, Fetish, Shemales  |  
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End of the Week

Ernest Gaines, known by most as ‘E’ or ‘Big’, bounded down the corridors of Presbyterian Regional Medical Center wheeling a patient towards discharge. It was shortly before 8:00 a.m. on Saturday which meant this was his final task of his shift. He made it to the waiting area and brought the chair to a stop as the elderly man peered out the window for his f****y.

“What’s going on,” a fellow orderly asked.
“Can’t call it,” E replied.
“I hear ya, man. You gettin’ off soon?”
“Yeah. Goin’ to the crib and chill. Got three in a row off.”
“I’d do that. But I got too many people at home to get a... Continue»
Posted by faggyboi 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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Peaches And Cream #1

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 ... Continue»
Posted by naughty_bi_interest 6 months ago  |  Categories: First Time, 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 4 years ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  
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xdresser foxxiroxxi fucked by daddys poker buddies

Well its all my daddys fault he made me dress up like a slut everytime he had a poker night to serve drinks and give massages the cheap bastard would not pay a girl to do it so he made me do it. I cant really complain but as after the first couple of times the awkwedness went away and I started to enjoy it when I got compliments and started getting better tips . My daddy was getting a bit annoyed and tried to stop me doing it but the players insisted that I was to be there waiter. This is when it all clicked into gear as it was my daddy who wanted this and now he cant stop it ,so I thought i... Continue»
Posted by foxxiroxxi 3 years ago  |  Categories: Fetish, Interracial Sex, 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 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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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 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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LOVE

I was work as a counselor for people with gender identification. One day a beautiful lady, Pham, approached me for an assignment related to her doctoral work at an university nearby. Her work was related with gender identification issues.

Our scientific bent of mind and approach to research enabled us to relate closely to each other. I would say that was an attraction. We met at least thrice a week for one year and all that we did was to talk and share notes on gender identification issues over coffee, tea, lunch and dinner. We spent days and nights talking about it over phone, at office ... Continue»
Posted by tran4mate 2 years ago  |  Categories: Shemales, Taboo, Voyeur  |  
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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 3 years ago  |  Categories: First Time, Mature, 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 4 years ago  |  Categories: First Time, Mature, 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 1 year ago  |  Categories: Fetish, First Time, 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 2 years ago  |  Categories: Gay Male, 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 2 years ago  |  Categories: Anal, First Time, Shemales  |  
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Owned sissy girl of dom couple Part 1

I met the mature dominant couple that I now call Mummy & Daddy on the internet. I am a 52 year old sissy who loves to be dominated, feminised and made to be a humiliated mincing sissy slut.
Their ad said they were looking for a full-time live-in mature sissy plaything. After we made contact they invited me to their house. I was instructed to bring any sissy clothes with me and to refrain from orgasm for two weeks prior to my arrival - a daunting task to say the least...
They answered the door together - he was a tall very masculine mature man in a suit, his trousers had a large bulge at the... Continue»
Posted by andrina62 9 months ago  |  Categories: Anal, Mature, Shemales  |  
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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 5 years ago  |  Categories: Fetish, First Time, 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 4 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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