Shemales Porn Stories
Page 11

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 2 months ago  |  Categories: Masturbation, 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 3 months ago  |  Categories: Anal, Hardcore, 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 why delay the fun!

After kissing me, his hands found my tits and pinched my nipples. ... Continue»
Posted by lornasababe69 3 months ago  |  Categories: Anal, Mature, Shemales  |  
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A Night At The Opera

I took my seat in the opera house looking...hoping...and aching to see if my companion was attending the opera that night. For the last two months, I and my wife had seats D2 and D3...and seated next to us were another couple. She was simply the most beautiful woman I had ever seen. Her beauty was amplified by my own dying marriage. My wife and I already had the divorce papers filed. Perhaps I was k**ding myself, but the woman seated next to us seemed to pay extra attention to me...and it was clear that her companion was bored and not interested in her. His loss...she had long blond hair...gre... Continue»
Posted by naughty_bi_interest 3 months ago  |  Categories: Anal, First Time, Shemales  |  
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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 3 months ago  |  Categories: BDSM, Fetish, 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 3 months ago  |  Categories: Fetish, Shemales, Taboo  |  
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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 3 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 3 months ago  |  Categories: Anal, Hardcore, Shemales  |  
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Dinner for Two

Dinner for Two

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 3 months ago  |  Categories: Group Sex, Interracial Sex, 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 3 months ago  |  Categories: BDSM, First Time, Shemales  |  
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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 3 months ago  |  Categories: Gay Male, Hardcore, 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 3 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 3 months ago  |  Categories: First Time, Shemales, Voyeur  |  
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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 3 months ago  |  Categories: Gay Male, Interracial Sex, 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 3 months ago  |  Categories: Gay Male, Masturbation, Shemales  |  
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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 3 months ago  |  Categories: Shemales  |  
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Spanish adult book store

A few years ago , when I was still experimenting with my Bi side , I went to Spain for a few days , walking round early one evening I chanced on a sex shop , .I went in and it was huge , I saw things that I hadn't anywhere else , I was in heaven.

Going further in there was a sign for theater so going through a door I found myself in the room with cubicles and little video players , I was pretty nervous but went and sat in one and started watching the films,
again the content was so sexy and new , to me , straight gay , lesbian but most of all it was the shemales, I was transfixed.
I wat... Continue»
Posted by jakuk 3 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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Halloween Night.

My wife has been at her mothers the other side of the country and will be for a few months, so I thought this would be the perfect time to go all out and see how convincing of a woman I could make myself. I bought hair removal cream, razors, new sexy lingerie, a sexy Halloween outfit, a wig and make-up. Naturally i received a few looks from cashiers, but I managed to smile and make a comment about how my wife's at work and leaves everything to the last minute.

As soon as I rushed home and got inside I began preparing even though it was still early, I knew id need extra time since iv never d... Continue»
Posted by RocknLoad 3 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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She spoke precisely, with authority, and though she no longer sounded vindictive her voice could still etch glass. She'd made up her mind, and when Cynthia's mind is made up there's nothing more to say. Now I had to make up my mind.

"That's how it is, Keith! My sweet disloyal husband! Your decision! You want this marriage to continue, we can get past this ... this thing you've done to me. To us. But you'll have to agree to one or the other. No more argument, no more floppy-eared, doggy-eyed pleading that you're so very sorry and it won't happen again and it was only sex and meant nothing, a... Continue»
Posted by lana100 3 months ago  |  Categories: First Time, Shemales  |  
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I now live in a cute, one bedroom house outside of Atlanta. My boyfriend, Daniel, owns it and invited me to live with him. We have dated for a couple of months and we have become close. We almost have not stopped having sex since we moved in. I am a little bit of a slut (or so I like to think) and he is always wanting to try something new.

After a few days things have gotten a bit normal. I heard his alarm, when he stopped it, he rolled over and wrapped his arm around me. I could feel his breath by my ear. I turned my head to him, he caught my lips quickly. Enjoying that kind of early morni... Continue»
Posted by bisubtaylor92 3 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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