Shemales Porn Stories
Page 18

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 6 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 6 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 6 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 6 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Choices

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 6 months ago  |  Categories: First Time, Shemales  |  
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Home.

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 6 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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Marinate with cum.. I mean love ;)

You see, I am a cum slut. I love to take cum all over my face. The more cum I can get the better. The place I usually go is a local adult movie theater with stalls in the bathroom. What are nice about these stalls are the glory holes. I love to suck cock through glory holes. There is something about sucking a cock from a total stranger that you can't even see. I have sucked a bunch that way, but I am beginning to want something more. I want a cum bath, a bukkake session. I want to be in a room with 10, 20 or even 50 guys with the sole purpose of having them all jack off onto my face. What foll... Continue»
Posted by CumLovingKitty 6 months ago  |  Categories: Gay Male, Hardcore, Shemales  |  
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How I Slowly Began to Change

Before long a rhythm had established itself between me and Stefan. He would regularly ask me if I had new pictures of me crossdressing, and I’d send him a few now and again to keep him happy. Occasionally he would buy me clothes, which would always come in the mail from some online shop or other. And frequently, at least once a week (and every time after he had sent me a ‘gift’ of clothes) her would demand I come over to his place so he could "show his appreciation of me”.

But as much as this felt like they had established themselves, I was also aware of slow changes. My crossdressing wardr... Continue»
Posted by tricked-sissy 6 months ago  |  Categories: Shemales  |  
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Blackmailed Crossdresser , part II

A few weeks after that first incident with Stefan where he had blackmailed me into having sex with him, I got a text message off him. I was a bit surprised, as we had managed to ignore each other in work. I was growing optimistic that this incident was behind me. Even though it was left me feeling violated and with lots of confused feelings about myself.

I was shocked to open the message on my phone and seen two pictures of him fucking me in the hotel! I was on all fours on he bed, in bustier, stockings and heels, with a wig on but visible to see.And he was behind me, obviously fucking me. ... Continue»
Posted by tricked-sissy 6 months ago  |  Categories: Shemales  |  
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Stefan's Blackmail

When I was about 19 I started to crossdress. I didn't have gay feelings or strongly identify as feminine but I felt strangely attracted to my older s****r's clothing. One day I tried on a skirt and I found this simple act feel so thrilling that at the next opportunity I tried on a two more things...a dress and and a pair of her jeans. I was always thin, especially when I was younger, and my s****r was only three yeas older than me, so I had little problem fitting in most her stuff. Actually the stuff at the back of her wardrobe, the stuff a year or two old that she didn't really wear anymore w... Continue»
Posted by tricked-sissy 6 months ago  |  Categories: First Time, Shemales  |  
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Being a good slutty Sissy

Being a good Sissy for my mistress

“Hey Martina. do you like what you see?” Samantha, a very beautiful shemale with tits size D, asks standing in front of me. A smile curls her lips as she strokes her 8 inch cock.

“Yeah, I'd love to play with a cock that big.” Martina says licking his lips at the sight of pre-cum dripping from the tip of her cock. I’m a 5 feet 11 tall sissy original called Mark. If I have to dress for my shemale mistress as a sissy gurl I call myself Martina.

“Well then, come and get it. on one condition. You're my pet until I'm satisfied.” Samantha says with a smile... Continue»
Posted by Arnie65 6 months ago  |  Categories: BDSM, Shemales  |  
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Sexual Fantasies 001

One of my sexual fantasies is what I call "f***ed anal orgasms" or "anal ****"

Everything starts with a date with a shemale scort. I arrive to her flat and a 185 tall woman, dark skinned and with a femenine figure, opens the door. She invites me to get inside with a toothpaste advertisement like smile and a long curly hair. She takes my hand and gides me to a room with a king size bed with black sheets.

She sits me in the bed and starts asking me
-What would you like to do, honey? Do you want me to start blowing you and then you fuck me in all fours? Or would you like a girlfriend expe... Continue»
Posted by Auspex 6 months ago  |  Categories: Anal, Hardcore, Shemales  |  
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Becoming Madison_CDs Daddy Chapter 2

"Madison I know you enjoyed that didnt you, you little faggot" I said as I reached the bedroom door.
" Yyyess daddy " he whimpered
" Tomorrow I want you completely shaven use your mothers hair remover and shave your cock dont let me down , understand ."
I shut the door and went to bed .
In the morning I went downstairs for coffee and waited.
I finished my cup showered then knocked on Madisions door and opened it.
He was there in his bed with his covers over his head.
I walked to the bed and pulled back the sheets.
There he was naked and smooth from the neck down his shaved cock laid ... Continue»
Posted by rabbit007 6 months ago  |  Categories: Anal, Shemales, Taboo  |  
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We met at the Gym

This is my first story. Feedback is appreciated.
When I woke up this Saturday morning I was hornier than usual, but I had to suppress my urges in order to make a 5:30am group fitness class. I put on my normal workout clothes, Gray/ White Stripe Shimera Boyshorts panties, Nike loose leg shorts, t-shirt, hoodie, socks and New Balance cross trainers. I like wearing the boy shorts for two reasons, one- they are very comfortable and two, sometimes I like to have my balls hang down on either side of the crotch. About 5:15am, I walked into the gym, swiped my membership card and walked past the r... Continue»
Posted by randy1stonez 6 months ago  |  Categories: Anal, Group Sex, Shemales  |  
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My New Lover!

I was still testing the waters a bit. I went out in my skinny jeans and just a t-shirt (I still don't crossdress in public at least not heavily, still uncomfortable), my slightly long hair makes me look very androgynous. I wear very subtle eye makeup as well, I am happy in my body, it suits being a guy for my job and a girl for my lover. I thought I liked him a little but by the time we made it back to my house, which was empty, an irregular occurrence, he had been very nice and hit on me a little. He complimented my body and my ass (not to stroke my ego but I love my ass, I get compliments on... Continue»
Posted by bisubtaylor92 6 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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We Met at the Gym

This is my first story. Feedback is appreciated.
When I woke up this Saturday morning I was hornier than usual, but I had to suppress my urges in order to make a 5:30am group fitness class. I put on my normal workout clothes, Gray/ White Stripe Shimera Boyshorts panties, Nike loose leg shorts, t-shirt, hoodie, socks and New Balance cross trainers. I like wearing the boy shorts for two reasons, one- they are very comfortable and two, sometimes I like to have my balls hang down on either side of the crotch. About 5:15am, I walked into the gym, swiped my membership card and walked past the r... Continue»
Posted by randy1stonez 6 months ago  |  Categories: Anal, Group Sex, Shemales  |  
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Chance Meeting at the Gym

This is my first story. Feedback is appreciated.
When I woke up this Saturday morning I was hornier than usual, but I had to suppress my urges in order to make a 5:30am group fitness class. I put on my normal workout clothes, Gray/ White Stripe Shimera Boyshorts panties, Nike loose leg shorts, t-shirt, hoodie, socks and New Balance cross trainers. I like wearing the boy shorts for two reasons, one- they are very comfortable and two, sometimes I like to have my balls hang down on either side of the crotch. About 5:15am, I walked into the gym, swiped my membership card and walked past the rows ... Continue»
Posted by randy1stonez 6 months ago  |  Categories: Anal, Group Sex, Shemales  |  
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Ashton & Terry

Mona Harris headed out of the door. She had both of her daughters in tow. It was going to be an all-day affair at the salon.

Terry heard his wife of three years start her white 2009 Nissan Altima. He waited for her to pull out of the driveway. He six-inch long, four-and-a-half-inch thick dick was rock hard. As usual Mona had given him no pussy. The six-foot-two, two-hundred-fifty-five-pound, dark-skinned, barrel-chested man got out of his bed. He marched down the hallway and into another bedroom.

Terry examined his cute, slim stepson asl**p. He walked over to the bed and ripped the black... Continue»
Posted by faggyboi 6 months ago  |  Categories: Gay Male, Shemales  |  
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NFL Season Opener

Marcus Phillips opened the door of his apartment. The six-feet-three-inch, two-hundred-fifty-pound dark-skinned man looked at the slim boi.

“Come inside,” Marcus ordered.
The twenty-six year old complied and said, “Yes, sir”

It was a Sunday – the second one of September. Marcus had asked the pussyboi to come over before the game. It was the season opener for the New York Giants. They were playing the Dallas Cowboys. The sissy boi switched inside. He was five-feet-six and weighed one-twenty-two. He had a caramel-mocha-latte complexion. The game started at 4:25 p.m. It was still early in ... Continue»
Posted by faggyboi 6 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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Another College Experience

My Junior year of college was definitely the most sexually active time of my life thus far. Granted, I just started my Senior year, but thus far, I haven't kept the pace that I did last year.

I started crossdressing a few years back and do it in public every now and then as I look pretty feminine when I get dolled up. I have made it a habit that every Halloween, I would dress as something sexy and girly.

Last Halloween, I had a plethora of costumes that I wanted to wear, but ended up wearing a sexy sailor's costume. It consisted of a very short mini skirt, a very low cut top, and a litt... Continue»
Posted by wattheef 6 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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