Shemales Porn Stories
Page 68

Mysterious Feminisation

After a few months of my ‘relationship’ with Stefan I realised that I had irreversibly crossed over the border between being a straight guy who liked to experiment with cross-dressing into being… well, something else. I am not sure exactly when this realisation hit me. Was it when I was pulling on a pair of tight girly jeans that I would pair with high stilettos and found I was not thinking how I might look in the mirror and how the clothes felt to me, but how sexy my ass would look to him? Or was it when in my day job I could still feel his cum still swimming around in my stomach from the nig... Continue»
Posted by tricked-sissy 11 months ago  |  Categories: Shemales  |  
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How I became Jayne The Crossdresser

It started in 1976,around August,I had just met John a guy my around my age,who lived alone near me. He wasn't shy to admit he was gay,and I was curious,and I told him one Friday after we got back from the pub about my interest. Before I knew it John & I had undressed & I had Johns cock in my mouth,sucking him off,& he soon quaked into an orgasm,cumming in my mouth so fast I gagged slightly before I managed to swallow most of it.John was keen to make it a pleasure for me & wanked me till I shot my jizz over his face & hair. This seemed to stir his dick & I watched as it hardened to its 6" and ... Continue»
Posted by tvluver2008 11 months ago  |  Categories: Gay Male, Masturbation, Shemales  |  
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Sissy's first BBC

This happened awhile ago, i was 19, and i figure some people have asked me to write more so here goes =]

I was lookin around on craigslist... so i was horny and wanting it! Scrolling around and found a black guy who wanted some ass. No real specific requests, so i figured i may as well reply. In my town it is a bit rare to find black men who are down to fuck a sissy! I had sucked one BBC before while visiting North Carolina, sucked him off in a park which was great =] But that is another story and not nearly as entertaining.

So he replied back. Very little info. A pic of his cock... whic... Continue»
Posted by AshleyXmith 10 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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The Surprise

A divorced man finds love unexpectedly.

My wife left me a few weeks after my fortieth birthday. She ran off with a coworker, leaving me with our condo in the city. Getting dumped was a wake up call for me. I joined a gym and began working out and eating healthier. I was never fat or anything, but I got really lean and cut and began to feel confident in myself.

My friends looked out for me, inviting me out to dinner and fixing me up with friends. Maybe I wasn't ready to date yet, because there really wasn't any spark with any of the women they were introducing to me. I wondered if ... Continue»
Posted by magas911 10 months ago  |  Categories: First Time, Mature, Shemales  |  
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Shemale Surprise

A married man is seduced and taken by a friend of his wife's.

"You can stay with Robert if you wish," Mary said on the phone.

I looked up from my laptop where I was pretending to be working when, in reality, I was reading, for the hundredth time, the brilliant novella 'Shemale School: a Teacher Seduced'. The story had created a new obsessive fantasy I had never even considered before: to be with a Shemale.

I even contacted the authoress to tell her how much I enjoyed it, and have since became one of her editors. I had just finished editing a gay cocksucking story that, althoug... Continue»
Posted by magas911 10 months ago  |  Categories: First Time, Shemales, Voyeur  |  
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Halloween..

Because I am a bartender even on Halloween, I had to work until 2:00am. Daniel works the total opposite; he came to visit me at work. All the staff was in costume. I was dressed as a witch, quite sexy I must say, it got me a few unsuspecting compliments. Apparently, I am rather passable as a witch. I was referred to as a girl a several times by people who aren't regulars, but who expects your bartender to be a 5'8", guy in a ruffled skirt, fishnets, corset, black lips and nails, covered in glitter.

Daniel hung around with me for a while then I lost him somewhere out in the party. He made a... Continue»
Posted by bisubtaylor92 10 months ago  |  Categories: Gay Male, Hardcore, Shemales  |  
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Submissive Sissy Jenny's First Cock

Submissive sissy Jennifer's first cock

There is a shy knock on your door. You open it, wondering who it can be. A stranger hands you the end of a dog chain, you can see that it leads to a red strap round his neck.
"I'm Jennifer, Sir" he whispers, softly & huskily. It becomes clear now - you remember the conversation on the web a few days ago. Not saying a word, you pull the stranger into your room with the lead, shutting & locking the door behind him. You slip the end of the dog chain over a coat hook behind the door. "STRIP" you command.

Jennifer slips off her coat - it was a co... Continue»
Posted by sissy_jenny 10 months ago  |  Categories: BDSM, First Time, Shemales  |  
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Dinner for Two


Dinner for Two
byWant2BUsed©


What can I say? My girlfriend and I have a gratuitous and fortunate sex life. Above all I am honest with her and she is with me, so when I told her I wanted to be dressed like a two bit whore and fucked with the largest "strap on" she would dare use, I was scared she would leave me. Instead we went shopping. The saleswoman at Victoria Secret must have wondered why we were buying the same thing in two different sizes. And as I looked back while my girlfriend was paying I noticed them both look me up and down and smile.

As time passed, my kinks became mo... Continue»
Posted by keripinkpanty 10 months ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  
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Made me a woman pt.1: intro (the first load)


My entire body is hairless now. Just finished shaving my long thick milky white legs. My toenails are painted black. My nails as well. I just shampooed my hair after dying blind for the first time. I had long hair, been growing it for over a year. It's below my shoulders, but now it's bleached blonde. Bimbo hair. It goes well with my green eyes. I admire them as I finish applying the whorish dark eyeliner and giving it that smokey eye look. Applying concealer, 3 different shades and contouring to leave no trace of a shadow after a close clean shave. Finally, the red slut lipstick. I look at ... Continue»
Posted by alexismorel 10 months ago  |  Categories: Interracial Sex, Shemales  |  
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Brian My Cruel Master

Brian my cruel master

*note this is fiction based loosely on fact


I met Brian early one Spring evening when I was 20.
I was out for a walk, no job, no school, just aimlessly
walking about.
He was standing there on the sidewalk of the
pleasant, tree lined neighborhood with a younger friend
so I walked up to them and introduced myself.
Hell, I had just moved into the area, I was bored and lonely
and wanted to make a buddy or two, nothing more.
The conversation went something like, “I live the next
town over and I saw you standing here and figured,
what the heck, you look l
... Continue»
Posted by yutubeslut 10 months ago  |  Categories: Anal, Hardcore, Shemales  |  
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Chubby legal male hooker

I guess one day somebody figured out that if it was legal to pay people to make porn, but not just to have sex, that the easiest way to 'legalize' prostitution was to have a camera running or take at least one picture at some point during the act. Since I am interested in all sorts of men this seemed like an idea with potential.

I started posting on all the free bulletin boards about my new 'business', Versatile Services. Catering to discerning gentlemen it would provide playful companionship and diligent attention. How do you like it? Perverted married guy who likes 69ing with chubby m... Continue»
Posted by cumquarts 10 months ago  |  Categories: Fetish, Shemales, Taboo  |  
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My Next Meeting with Master part 1

One day I received a text message from my Master, who had asked if I would be free in a week and half time, I text back to say yea I would be free and then he said good and asked if I would be free for at least two days. I replayed saying yes I would be free. So we had arranged to meet at his place at 830pm. He asked that I would bring with me the straight jacket, all my hoods, mitts, collar, whip and brand new padlocks that were still in a sealed case for him to open when I get there. Also that I need to wear my mini dress that is wet look and boots.
I could not wait for this day to come as ... Continue»
Posted by dallasrose 10 months ago  |  Categories: BDSM, Fetish, Shemales  |  
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Last weekend

I had arranged a meeting with a new gentleman lover.

I was excited about being naughty.

Knowing I was going to fulfill my craving with a big new cock to play with made me bulge in my panties as I drove to his place.

I arrived at my new friends place a little early.

He answered the door in a dark Tshirt and jeans that hugged him in all the right places.

There was a little chit chat, but we both knew what we wanted. He wanted to fuck me and I wanted to feel a hard cock fill me with cum.so why delay the fun!

After kissing me, his hands found my tits and pinched my nipples. ... Continue»
Posted by lornasababe69 10 months ago  |  Categories: Anal, Mature, Shemales  |  
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....just me being a slut

I whimper and moan with lust as your fat veiny cock slides in and out of my well trained slutwife asspussy.
i push my ass out to get as much of you into me as i possibly can, my cunt wants your whole cock.
you slap my ass with a loud smack "you lovely little whore, you cant get enough of my cock, can you?" you laugh while manhandling my body "NO, I want your cock all the time" I gasp from your hard and deep thrusts "I need to be filled all the time!" you yank my head back even further shove 3 fingers into my mouth and hold my mouth open not missing a beat plunging deep into my bowels. Your ... Continue»
Posted by bimbodollval 10 months ago  |  Categories: Anal, Hardcore, Shemales  |  
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Happy Trails

Once every so often, I go out of town to indulge in my crossdressing fetish. Nothing too fancy, just a reasonable motel within an hour drive. Just far enough away from the daily personal and professional grind.
Most of the time, this involves me playing dress up in the room and satisfying myself with my toys. Over time this has gradually progressed to a point where I have gone outdoors dressed up. The most recent event involved me enjoying a quick late evening dip in the hotel hot tub.
My most recent excursion was a step further for me. About a 10 minute drive from the hotel is a mixed use... Continue»
Posted by nikki_toyz 10 months ago  |  Categories: Masturbation, Shemales  |  
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The real me..

Finding the real me



I live in Perth, Western Australia and go to a place called Perth Steam
Works. It's a small building down a side street and not much to look at.
It's a place where Gay men can go, it's clean, discreet and unobtrusive.
I don't consider myself gay as I have no interest in men that is until I
am dressed. Is this the same for all like us?

I have been there a few times with the sole purpose of getting it off
with men. Normally I take all my gear with me in a bag and change there
but it's difficult because there are no changing rooms, or none that I
have seen, an... Continue»
Posted by klammer 10 months ago  |  Categories: Anal, BDSM, Shemales  |  
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Made me a woman pt.2: Degradation

I'm regaining my senses... im on my back, in my bed, im naked, i feel an around me, and heavy breathing next to me. My big black man was sweating and panting. im sweating, my body is shivering, and my ass is raw and leaking out his cum. His hands start running all over my body groping my tit, rubbing my phat ass. i can feel myself getting excited again and getting hard. he notices that so he spits in his hand and grabs me by the crotch. again his massive hand completely takes me and he starts rubbing me. i start moaning and gyrating my hips on his hand. he leans over and whispers in my ear "yo... Continue»
Posted by alexismorel 10 months ago  |  Categories: BDSM, Interracial Sex, Shemales  |  
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Introducing Jessica

Say hello to Jessica, she's 19 (at the time of this story) and very friendly.

The name I chose when becoming more and more of a sissy.

It was a quiet weeknight, and I was alone at home. Fresh out of the shower and sitting naked at my computer, online and chatting to lots of horny people.

After a while of chatting a while, some private chats were going on and getting hot and heavy. Some with new people, some with same people I've chatted before.

In this instance was someone I'd chatted to many times, henceforth known as John. We chatted often and about many topics, but mostly about ... Continue»
Posted by Want2BeTrans 10 months ago  |  Categories: First Time, Shemales  |  
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Meeting Mr Mac Muffin

Meeting Mr Mac-Muffin

Now it was like 11.30 pm Saturday night when I had finish work and was one my way home when i saw my old gurlfriend Loraine at the bus stop. Its like two years since we last saw each other so i figure hell why not an the bus would leave the terminal an 12 sharp . Since I always have a stash of clothes in the car, I pull into a park an pull out my girl clothes.
In less that 10 minutes I was a girl, my brunet wig was a little ruffle an some red lip stick made up my face . My homemade breast and pussy with my black lace panties took care of m... Continue»
Posted by hellpuss 10 months ago  |  Categories: Anal, First Time, Shemales  |  
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The Club and The Morning After

As we were leaving for the club I couldn't help but notice how sexy Linda and Kathy were dressed. Kathy was wearing a short black dress that seemed molded to her figure and nearly exposed her ass it was so short. Linda had on a pink, glittery looking dress that was flowing, short but not as short as Kathy's dress. Linda's nipples were visibly hard and both ladies were wearing high heels.

When we arrived at the club the doorman greeted Linda and Kathy like old friends, hugging and kissing both, then nodding to me and Henry. One could hear the music outside, but when the doorman opened the do... Continue»
Posted by trisexual69lvbbc 10 months ago  |  Categories: Fetish, Group Sex, Shemales  |  
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