Shemales Porn Stories

New Neighbour New Role Part 2

'Wake up sweetie,' Said Vicky, rubbing my sore butt. 'Here, take your medicine and I'll sooth your pussy.'

She passed me another of the tablets that Mistress Jen gave me earlier.

'What are they for?' I said, swallowing the pink tablet.

'Conditioning. Besides, you promised Mistress didn't you?'

'Yes.'

'Now stretch out on your front whilst I soothe your hole. My it is so puffy and pink.'

I moaned as Vicky started rubbing lotion into my hole. 'It feels so good.' I said dreamily.

'It should. It's got clove oil in it.' Vicky started dipping her index and forefingers of bo... Continue»
Posted by waraxe13 1 day ago  |  Categories: Fetish, Shemales  |  
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2 years ago




I am a married sissy cd and my wife has known about my desire to dress since we were married. We have been married 10 years now. She hates my dressing and all of my sissy desires and wants nothing at all to do or even see or hear of them. Well one night I told here that I had to go out of town for training for work and that the training was only in the next state over so I could drive but still had to stay the night. She believed me so I booked a room at a local Holiday Inn Express and got all of my sissy/CD clothes, shoes, makeup, wigs, sex toys...etc together packed them in the miniva... Continue»
Posted by Krissy_Love_Sissy 2 days ago  |  Categories: Fetish, Shemales, Taboo  |  
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Me and Mrs (Mr) Jones.

My first business trip as a married man. My first sexual adventure.

So at the hotel bar around 2230 is not a particular hotspot on a Monday night but this did not turn out to be your average Monday. I had a excellent day with work smashing previous records and was feeling very good about myself so I sit on a corner table with a bottle of 1997 chateaux du pape and face the bar. I see the occasional person have a drink and leave whilst I fantasise about how they would approach me if this was reality porn. Then she walked in. As I observed her long legs, 1 bent at the knee leaning on the bar s... Continue»
Posted by nomatterhowhardyoutry 2 days ago  |  Categories: First Time, Shemales, Voyeur  |  
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Bathouse Fun. First Time getting Fucked.

I have always known I was bisexual since I was a k**. I have topped but never bottomed, I have attempted bottoming a few times. First time I was 16 my friend and I tried, we didn't have lube and I wasn't streached out properly. A few months ago I bought a butt plug which is 4 inches long and a 8 inch dildo. I lube every night and put the plug in and every other night the dildo. It feels good when I do so. A description of myself, I am a black male, 51, looks to be in my 40's. Slim 5'8, 140 lbs. I have a 8 1/2 inch uncut BBC.

Last night I go to the bathhouse, I was feeling extra horny. I pay... Continue»
Posted by iamcontent 2 days ago  |  Categories: Gay Male, Group Sex, Shemales  |  
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Cubicles heels and dirty men

It's 730am..Tuesday morning and I've just spent the last hour and a half inside a toilet cubicle. .x dressed and hooded with my favourite 2" diameter  dildo for company ..it was my fifth visit in the last 6 days.. This time what with it being so early I was alone throughout and simply laid across the toilet seat on my back which then made my stockinged legs reach vertically towards the toilet ceiling. .with my red soled black Mary Jane platform heels high above me I felt very dirty yet very sexy..my dripping ass ,stretched and beautifully ruined was feeling happy with what it had taken ..an re... Continue»
Posted by THE-HEELS-STAY-ON 3 days ago  |  Categories: Anal, BDSM, Shemales  |  
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“Friend”

University “Friend”

Finally I had earned a little more freedom. I was off out of my sl**py village and at university. I had a small flat in an apartment block all to myself in a nice enough part of town. I unpacked my clothes and settled down for my first quiet night in, but as I put a few of my more sexy items away, I changed my mind. I hopped in the shower and cleaned up my legs, arms and face. Everything else was kept smooth for ease. I let my now shoulder length hair dry off as I picked out an outfit. I decided seen as it was my first night in a new town that I should make a good impres... Continue»
Posted by klammer 3 days ago  |  Categories: First Time, Gay Male, Shemales  |  
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New Neighbour New Role

It was a hot damn day and my neighbour was out in her balcony with two of her pals, laughing, drinking and enjoying the heat. I'd just moved in next door and our balconies are parallel to each other, no private divider. At eighteen, these were my first moments of independence and I was loving being able to do what I want – a home to freely play with my boypussy. Although at this moment in time all I'd managed to do was unpack a couple of essentials - TV and console.

So yeah, I was checking them out in between haphazardly setting up my den and enjoying myself at the same time - what kind of... Continue»
Posted by waraxe13 3 days ago  |  Categories: Fetish, Shemales  |  
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Miss Kim

It was the middle of the summer, and Shirley, Marsha, JJ and her s****r Claudia and Claudia's two daughters were taking their annual 2 week vacation in North Carolina at her parent's house. This left me all alone, a bachelor again. Claudia lived in Northern Virginia and had driven down Saturday so that they could pull out Sunday morning. After they had left I spent the rest of the day laying around munching on snacks, sl**ping, and just doing whatever I wanted.

The week was going mostly the same way, I would get home from work, strip down to tee shirt and shorts. I would lay around enjoyin... Continue»
Posted by blkjack0718 4 days ago  |  Categories: Anal, Shemales  |  
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Be-cumming a School Girl - rewrite

Be-cumming a School Girl - Rewrite

From the time I was 5 or 6 I would sneak into the lodger’s bedroom after she had left for work. I would dress up in her lingerie and climb into her warm bed. It just felt so good wearing silky clothes which felt so delicate against my skin. I just loved to feel feminine. If anyone looked in I would pull the covers up to my neck to hide what I was wearing. A few years later I would be wearing my elder s****r’s panties and occasionally my mother’s when she was out. I guess she was suspicious because one day my s****r caught me out and paraded me in front o... Continue»
Posted by Sally5050 5 days ago  |  Categories: Fetish, Shemales, Taboo  |  
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THE HUNT: MORAL CODE pt 1

whats up everyone ! i just wanted to share another epic fender bender story of my interesting life and chronicle the events that have happened over the last 48 hours while everything is still fresh. i never write short stories.. i like to reminiisce about each detail as i remember it

life is like a box of chocolates.. you just never know what your going to get!!

first off... if you are reading this .. you can check out my profile page AZNSWAG, remember to read the requirements if you plan on adding me. i was an uploader but recently got the dreaded 3 strikes... Continue»
Posted by AZNSWAG 5 days ago  |  Categories: Anal, First Time, Shemales  |  
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The Tutor and Jenny (Part 5)

The Tutor and Jenny (Part 5)
by Claude van Feinbode

"I know," said Gina. "Fuck me, and you'll be a virgin no more"

My cock was already sliding in and out of Gina's tight ass. I couldn't see Jenny as she pushed her beautiful cock into Gina's wet pussy, but all I heard Gina say was, "yes…that's it…..slowly….look at your dick…just look at it as it moves."

I was on my back and I could only imagine the sight that Gina beheld. Two cocks pushing in and out of her. I was holding Gina's hips as she moved rhythmically to the tempo of two cocks pleasuring her. I took my ri... Continue»
Posted by ClaudeVanFeinbode 5 days ago  |  Categories: Group Sex, Mature, Shemales  |  
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Playtime Stories 15 - ABS Wildlife

As usual, a hot mix of real experiences and fantasy. The part that is fantasy would surprise you- ENJOY and Comment please!!

15 Playtime Stories 15 – ABS Wildlife

“Just another trip to the arcade” turned into a very memorable time. I was away on business at a convention and very horny. I hadn’t been able to indulge in nearly a month and a half. The first night of the trip I had been fairly lucky for a Wednesday. I had done a lot of cock sucking, but as a guy. Thursday afternoon I still had the itch – the itch to be a slutty gurl. I got out of the networking session at the bar n... Continue»
Posted by 6988slutty_rbckyy 5 days ago  |  Categories: Hardcore, Interracial Sex, Shemales  |  
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First Time Shemale Surprise

It was pretty late and I was well into my drink. God knows where my pals had gone off too. I was sat in a bar nursing a bottle of beer when this tall, sexy lady sauntered towards me, her black wavy hair bobbing with each step and her dress shimmering purple and gold as the dim light reflected off it.

She rested her hand on my leg and without taking her bold eyes off me said, 'Hi. I'm Jess. Drink?'

I was still fairly lit, but completely taken aback by her directness, I still managed to mutter, 'Sure.'

'Bobby – Two whiskies.'

We clinked glasses and she downed hers in one. Not wa... Continue»
Posted by waraxe13 5 days ago  |  Categories: Shemales  |  
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My New Trainer

transsexual – oral – anal – blowjob – workout

"So, do you need a spot?" she asked. Wisps of red hair, which had fallen from her pony tail, framed her face as she looked down on me.

"Ummm sure," I lied. The equipment at the bench press station where I was working out was designed to be used solo. With a quick flick of the wrist I could lock the bar into any safety position, if I had gotten into danger, but accidents do happen and you can't be too careful. Besides, I wasn't going to turn down help from the most beautiful girl in the gym. She also happened to be the only girl in the ... Continue»
Posted by naughty_bi_interest 5 days ago  |  Categories: Anal, Hardcore, Shemales  |  
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The Roommate Pt. 04

sissifcation – sissy – feminization – prostitution – fisting – anal – blowjob – transformation – spanking – domination

I swiftly walk across the courtyard, the taste of cock still lingering on my tongue. I glance across the area and notice it's mostly empty now that the morning lectures are over. I look for Jamal since he's one of the only people I even know, but he's gone too. I take my phone out to check the time and see that it's 12:16. I guess I sucked cock for longer than I thought, 15 minutes felt like only 15 seconds. I have 45 minutes to kill before I can meet with Mr. Gibbs,... Continue»
Posted by naughty_bi_interest 5 days ago  |  Categories: Anal, Fetish, Shemales  |  
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Gangbang at Ricks part6 home alone


Well we sit down, took a deep breath, Rick started to play with my Red worn out Bubble Butt , man it's sore Daddy, He said he had some lotion, made me get on all fours, asume the position, he ordered. He said how sexy slut cum pig sissy, slapping my tender bottom, then went to town both hand on my cheeks rubbing in the lotion, He said, if I pull that fat Butt plug out cause I was trying to poop it out, It was the new fat one, no way daddy said, slapped my wet red checks hard, we better be in the shower, not on the couch. That's a boom ready to explode boy, just relax, ok daddy. I did and Ri... Continue»
Posted by mrheat22 5 days ago  |  Categories: Anal, Gay Male, Shemales  |  
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Fucked by a mature woman after tennis!

This is a true story from a few years ago about my first time with Karen.

I'm a pretty keen tennis player, and have been all my life. I started attending a weekly roll-up session at my local tennis centre a few years ago with my ex, after we split up I continued going but mainly because of all the MILF's that went, and because it was during the day time, I was the only guy under 50, which meant I was generally the focus of all their flirting. Generally we would play a set or two of men's doubles and a set of two of mixed doubles before maybe grabbing a cup of tea before heading home.

Ov... Continue»
Posted by woorls 5 days ago  |  Categories: Mature, Shemales, Taboo  |  
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Captured and Turned

HI, this story is fiction. I hope you like it.
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I was confused as I found myself coming to consciousness. I say coming to because the last thing I remembered was having dinner with my friend Joe and his wife Stacie.

I was in a dark room and my vision was blurry. I felt restraints holding my arms behind me and I was in a wooden chair.

"What the fuck?"

More and more senses returned and I found myself fully conscious now. I was tied to a wooden chair completely naked with my legs secured to the chair's legs and my a... Continue»
Posted by kevinj631 8 days ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Restaurant Futa Fuck (Part 1)

"Did you want to grab something to eat this afternoon? My treat?" I said, eagerly awaiting Sar's response.
"Sure thing, Bianca! I have a lunch break at one. Wanna meet up?"
"There's a great Italian place not far from your office. Paradise Restaurant I think it's called. I've been thinking of trying it for a while." I lied. I had been there before, but I wanted her to feel like we were experiencing something new together.
"I think I know the place. I'll see you there soon."
"Sounds good!" I hung up the phone and let out a deep breath. Sara was gorgeous, with long ... Continue»
Posted by BiancaBigTits 8 days ago  |  Categories: Fetish, Lesbian Sex, Shemales  |  
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The Tutor and Jenny (Part 4)

The Tutor and Jenny (Part 4)
by Claude van Feinbode


My knees were a little weak as Rachel walked out of the room. I realized that I was keeping my guest waiting and I quickly dressed in blue jeans, black button up shirt with French cuffs, jacket and comfortable shoes. I splashed some cologne and walked out of the master bedroom.

As I walked down the stair towards the main sitting room I heard Gina and Jenny talking while music was playing at a low volume. I smiled and marveled at how Gina had the ability to make anyone feel at home.

"Claude," Gina said. "Its a... Continue»
Posted by ClaudeVanFeinbode 8 days ago  |  Categories: Fetish, Shemales, Taboo  |  
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