Shemales Porn Stories
Page 12

Our naughty lesbian maid

Last summer my girlfriend and I went on holiday to the beautiful Greek island of Lesbos for two weeks of fun in the sun. I had a met Sasha a few months earlier at a club when I was out dressed as Tania. She was fascinated by my appearance and looks even though she knew that I was a slutty transvestite. Sasha was herself a free-spirited woman who was looking to meet other open-minded people so right from the start we hit if off with each other. We quickly got involved in a relationship and she completely accepted the male and female halves of my personality. So after a couple of months we decid... Continue»
Posted by lightwave40 1 year ago  |  Categories: Group Sex, Lesbian Sex, Shemales  |  Views: 3321  |  
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First time with a Shemale

First off this is a true story. I lost my virginity at a young age so sex is always been something usual for me. As far as how I lost my virginity... thats another story. I have always dated women that were openminded, bi-sexual and down right sluts. I have been in strange conversations and situations because of being soooooo "openminded", heres my story...

Bella and I were getting dressed for a night on the town. We had plans to meet a couple from a a website we were members of. So we were planning to have some fun after we had drinks and got them back to our place. In route... Continue»
Posted by trannincestluva 3 years ago  |  Categories: Shemales  |  Views: 3319  |  
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My transformation continued

I was made to feel sexy by my friend... and till to date i cannot forget that feeling of being wanted and being special.

That day in the tree house... my friend had a surprise for me. He said that i had smooth skin and wanted to feel it. He touched my face and stroked my soft hair. He lifted my chin and gently touched my lips. And I don't know what got into me. I opened my lips and sucked his finger. I closed my eyes and sucked his finger. I was doing this for about a minute or two when i heard his voice whisper into my ears - want to see something special? I instantly said yes.

I let go... Continue»
Posted by tran4mate 5 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 3313  |  
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My absolute ultimate fantasy

When I was growing up my pops had a auto repair shop out in the country right off the crossroad of two main highways we were never going to be rich but we were very comfortable When I graduated high school he gave me half of the business,so I could take over when he retiredThat first summer is one that has shaped my life all due to a Texas gal named amie Belle. When you are young and full of energy and wanting more out of life sometimes you can go a little overboard.Many mornings we would get to rhe shop and there would be a traveller broke down sl**ping in their car waiting for us .I bought a... Continue»
Posted by diamondave65 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 3309  |  
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My first time with a tranny

I had been looking at shemale porn for a while and dreaming of being with one. A few years ago I got away from work early and decided to have a few drinks. I was horny and soon looking at adverts in the paper when I stumbled across one for a ts hooker in the area. I called then number and the husky voice told me the address and to come in 30 minutes.

The next 30 minutes I was very nervous and took a minute or so before I worked up the courage to ring her doorbell. She let me in to her flat dressed in very little. Slightly taller than me, amazing breasts, big slutty shoes and an already erec... Continue»
Posted by ross80 1 year ago  |  Categories: Shemales  |  Views: 3306  |  
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SISSIES TRAINING PART 1

SissyIndy©

I responded to an ad on Craigslist from some guy asking for help to move some furniture. He was paying pretty well and, after I practically laughed at him for asking if I could lift the furniture, he agreed to have me over to get it done. We moved everything around for what felt like hours, often moving the same piece of furniture to what seemed like the same place it was originally. Finally he decided he liked the new arrangement, which wasn't that drastically different than how it looked when we started. Obviously exhausted, I sat down on the couch. He asked me if I'd like a Ga... Continue»
Posted by stig1963 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 3304  |  
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Fixing her computer

****d (sort of) by a Shemale!
By johnnyshemalelover


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 w... Continue»
Posted by leadpencil21 1 year ago  |  Categories: First Time, Hardcore, Shemales  |  Views: 3296  |  
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A Slut is born 3


I shrank back into the kitchen but Jim barked at me to stop.
“Where do you think you’re going?” he asked.
“Just back into the kitchen,” I replied, fear creeping into my voice.
“Not just yet,” he said “Why don’t you tell us all what you just did in the kitchen?”
“What do you mean, I was doing the dishes.”
“Don’t you dare lie to me, slut.” Jim thundered.
Really scared now, I answered “Well, Stan came in and held me down and fucked me.”
“So, you’ll fuck Stan but not the rest of us?” Jim said,
“What kind of host would I be if... Continue»
Posted by vosmou_vrot 3 months ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 3294  |  
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Loaning me out to strangers

My wife and her friend Tina were going shopping in Kansas City for the week end. I knew this meant that I would be with Phillip. Tina's husband and the man I can't stay away from his cock. This meant I would be dressing up like a slut and servicing Phillips cock the whole time our wives were in KC. I started getting ready even before Phillip called.
When he called I was already showered and shaved. Waiting for him to tell me how he wanted me dressed. Of course he said he wanted me dressed like a slut, but to dress for going out in public. This scared me. Public? What did he mean b... Continue»
Posted by firstknightd 7 months ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  Views: 3287  |  
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Once upon a time, I dated a Co-Worker...

It was summer and Dad had asked me to help him around his car insurance agency. Mainly I answered phones and typed in reports on the computer. Couple of nights a week, I would also vacuum, clean up and straighten the office a bit. Had the weekends left to go to the beach and hang out with my friends. Robert and Mayra still worked there, they had been with Dad for years. Both were appraisers, and were in and out of the office constantly. There was a new part-time clerk. Her name was Natalie, in her mid-twenties, a tall girl with long brown hair and hazel eyes. Chatty and friendly, I felt... Continue»
Posted by latinCharm 1 year ago  |  Categories: Anal, Shemales  |  Views: 3256  |  
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SHEMALE SURPRISE #3

i have just fulfilled one of my fantasies with the help of niki, who used to
be nicolas a male cousin of mine who is now living life as a shemale. i have
just swallowed a river of cum after sucking on my very first cock. being male
i have never thought of myself as being gay, and i still don't as i am not attractive to males at all. i love being hetero, but i do have an attraction for crossers or shemales.
my cousin niki and i were having our first tryst and after making niki cum
in my mouth she still retained her erection, prompting me to ask if would mind
fulfilling another fantas... Continue»
Posted by qrystofer 8 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 3255  |  
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A night out with my s****r

Following in from Shopping with my s****r - Please read my other stories first to set the scene.

Jane and I lie embracing on her bed, our naked bodies merging into one as we hold each other closely.

"What do you want to do tonight?" I ask

"I was thinking we could have a night out together, maybe a meal and a few drinks, see where the night takes us!" Jane replied.

"That sounds good to me, I haven't been out for a few weeks because of my exams."

"Well, I'll treat you to a nice meal and a bottle of wine on one condition" Jane offered with a devious smile on her face.

"Go on,"... Continue»
Posted by ukdan78 2 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 3253  |  
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My first time with a BBW Shemale turned into a thr

I was at the club on a saturday night and didn't really expect anything different to happen that night oh boy was I wrong, happily wrong. I was sittin at the bar gettin d***k as hell and this voice from behind me and says " hey big daddy can I sit with u ? " I look up and I see this fine, phat, thick, lightskinned woman lookin right at me. Me bein' a BBW lover and partial to light skinned black women she was a wet dream cum true.

I said sure u can sit here baby if u tell me your name. She says " my name is passion, whats yours daddy ? I told her and we start to chat about things we like an... Continue»
Posted by Champdick 1 year ago  |  Categories: Shemales  |  Views: 3245  |  
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Slut bi cross dresser

Party Surprise - First sex as a Crossdresser.
This is a work of Fantasy. I hope you enjoy.

Stephanie and I had been married a few years and enjoyed a reasonable sex life. She knew of my dressing and although she didn’t approve she indulged me now and then and we had sex when I was dressed or with me wearing lingerie. I think secretly she was jealous of my legs. She was a petite sexy woman and we were almost the same size but I still had my own stuff that I’d secretly obtained from eBay and op shops.

I didn’t consider myself bisexual, certainly bi curious at least. I liked watching guys ... Continue»
Posted by pesty 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 3236  |  
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Airconditioner repairman laid some pipe

I was literally bored to death when my mom went on a vacation, i was hoping that i was gonna enjoy freedom when mom's away but things got worse as i found out the air-conditioner wasn't cooling the house, it was the dog days of summer and i really hate this muggy, hot weather. So i gave a call to the place where we bought it and asked them if they could send someone to fix it. Like i said, the weather was terribly hot, therefore i was wearing a micro-mini short which was showing of my curves in a very revealing way. It was almost 4.00 pm when the doorbell rang. I was expecting the same guy... Continue»
Posted by Slave4str8twinks 5 months ago  |  Categories: First Time, Hardcore, Shemales  |  Views: 3235  |  
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Jeremy's Punishment

"Roberta, we need to talk." I said as my wife got into bed.

"About what?" She had her people magazine so I knew she didn't want to talk, she wanted to read.

"This is difficult, but I have to say it." I cleared my throat and looked for the right words. "I want your permission to cheat."

She stared at me for a moment. "Are you out of your fucking mind?" She asked.

"C'mon, be reasonable. I mean, how long has it been since we had sex?"

"That's all you ever think about --sex."

"Because I never get any!" I said. "Do you even remember the last time?"

"What about Halloween?... Continue»
Posted by sparkyking 28 days ago  |  Categories: Shemales, Taboo  |  Views: 3244  |  
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The Next Morning

I hadn't planned on getting d***k last night but what can I say? The mood was just right for it, me and Nicole are c***dhood friends and although we've branched out and built our own lives and become two very different people, we still find a way to make our friendship last throughout the years, you could say that she's my best friend, I've been there for her and she's been there for me and people like that seem rare to come-by these days so it's safe to say she means allot to me though clearly I meant much more to her because here was, waking up in her bed next to her the following morning.
... Continue»
Posted by RunandCummer 5 months ago  |  Categories: Fetish, First Time, Shemales  |  Views: 3232  |  
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Weekend retreat

When I go to work, I am in 'boy' mode. I certainly am not the most masculine person, and I am pretty certain that everyone knows my sexual preference. I often get mistaken for a woman even when in 'boy' mode. Whatever. I am who I am... deal with it :)

A few years ago my former workplace had a nice mountain retreat weekend. I love these retreats, not because I become closer to those I work with, but because they are so peaceful.

I arrived at the lodge on a Friday night and spent the next day communing with nature. My fellow workers were doing other activities, and I spent most of my t... Continue»
Posted by zaria_ts 7 months ago  |  Categories: Anal, Shemales  |  Views: 3229  |  
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My shemale boss part 2

Friday 12pm was here, I nervously knocked at my bosses door part excitement part apprehension ran through my body.

A clear come in could be heard from within by my boss Miss Jones so I went in. Ahh Rob right on time, take a seat and I'll be with you in a minute, she said.

I sat down opposite her desk whilst she continued to study her paperwork. Her black rimmed glasses were on the tip of her nose and with her finger, she curled her long black shoulder length hair. Through her glass desk I could see her tight black leather trousers she had on and black 5" heals. She had walked through my... Continue»
Posted by big_rob49 1 year ago  |  Categories: Shemales  |  Views: 3212  |  
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1st time with an angry Trannsexual

This is a true story that took place in bayswater London in June 2012.

I had often wondered what it would be like to have sex with a hot transexual girl. Finally with the help of the Adulwork website i was able to find some stunning TS girls available for meets in London. I chose a hot blonde brazilian beauty named Isabella. She looked amazing in her pics and her cock looked gorgeous. I had to meet her.

I emailed her, she gave me a number, and i called to arrange a suitable time to visit her.
I knocked on the apartment door and awaited a response. Moments later the door crept open and ... Continue»
Posted by kentcariblad 6 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 3208  |  
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