Shemales Porn Stories
Page 69

sailing baseball and TS dates

Shelly and I had been chatting online for almost two years. We had share a great deal of personal information and shared in each others personal triumphs and tragedies. She lived in Seattle Washington and I was in Oregon in the sl**py hamlet of Lewisburg. Often we had talked about meeting and each of use has passed close but not arranged to meet. My issue was long term relationships are always prone to fail and she was , by her admission , looking for someone closer to home as well.

I have a sailboat, a C-22 swing keel, and had for several years been trailering it north each year for tw... Continue»
Posted by sailor_brad2 2 years ago  |  Categories: Anal, Shemales  |  
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Craig List

Craig story for posting
She is yours for the tacking!! I have left my sissy chained to tree waiting to be used.
We begin begin your transformation from loving boyfriend to my precious Gumdrop the slut. I begin by stripping all your man close off of you and leaving them on the floor. I tell you have sexy you will be once we get all that ugly hair off of you. No man wants a hairy girl. You MUST also be very clean for the men you will service. They wont a slut but not a dirty whore. I will help you to become the sissy that you should be. I pull you into the bathroom. Scented water filled with ... Continue»
Posted by IamMistressAnne 2 years ago  |  Categories: Fetish, Shemales, Voyeur  |  
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My first crossdressed cocksucking (true story)

It happend few years ago. My ex gave me a "hall pass" to explore my sexuality although she didn't like me dolled up and looking like a cheap slut.

I was chatting for some time with this man on the IRC. He liked crossdressers, boys on the way to become fem sluts. He was mature, around 50. And he was also travelling through Europe.

One day, he caught me online and told me that he will be passing my town and stopping by in the hotel. I was supposed to meet him on friday night at the hotel. He gave me only one day warning, so i had to prepare the next day for the meeting. I didn't tell my ex... Continue»
Posted by kamislut 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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Final Episode of Roommate Stories

I brought Robert into my bedroom and stripped off my towel. I grabbed my bottle of lube from the nightstand and wet my pussy. Robert had his clothes off in about 5 seconds flat. His cock was completely erect and I didn't need to suck him to make him hard. He climbed into bed with me and proceeded to make love to me. Where Ed would mostly use me like a blow up doll, Robert was a sensuous and tender lover. He had experience with gurls and knew how to make one feel like a woman in bed. He would caress my legs and rub my asspussy while kissing me up and down my neck. He would also kiss, li... Continue»
Posted by rikki50 2 years ago  |  Categories: Gay Male, Shemales  |  
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More adventures with my Roommate

It was Saturday evening and I was dressed in my "maid sissy outfit" waiting for my roommate, Ed, to come home. I heard the sound of two male voices talking loudly outside the front door of our apartment. One voice was the unmistakable booming voice of Ed and I didn't know who the other voice was. The door opened and in walked Ed and another guy. Ed introduced us, he said, "Baby, this is Robert. Robert, this is Baby." Robert smiled and said hello to me as he leered at my stocking clad legs. Robert was quite different from Ed and I wondered about their friendship. Robert was in his late 5... Continue»
Posted by rikki50 2 years ago  |  Categories: Gay Male, Shemales  |  
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How it all began.....

It all started 7-8 years ago, coming home after a night out in the town and feeling horny...

My shoe's left in a heap by the door and a trail of kebab meat leading up to my bedroom, I knew that my happy wank time was about to commence. As soon as I got in my room my jacket was flung onto the floor, I was humming my favourite tune as I used my toe to switch on my computer. Man I was so d***k and turned on, just looking for something hot to get me hard and to blow my load.

The computer loads up and I'm already down to my boxers, sitting on my chair, one hand on cock the other on the mouse.... Continue»
Posted by shemalesearcher 2 years ago  |  Categories: First Time, Shemales  |  
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Settling in with my new RoommateHe

It didn't take very long for my roommate, Ed, to figure out that I was a submissive sissy slut. I think that Ed was basically a straight guy as far as his sexual orientation went but he liked the fact that, if he couldn't score away from home, a willing mouth and ass was always at home when he wanted it. Ed insisted that I wear at least a garter belt and stockings to bed every night. He said that he liked the way the garter belt "framed my ass" and he liked the way my stockings felt when I would wrap my legs around his waist. So, I would go to sl**p in my bed dressed in sexy lingerie and s... Continue»
Posted by rikki50 2 years ago  |  Categories: Gay Male, Shemales  |  
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The Host

Sunday...ahhh, my favorite day of the week. You see, that's when me, and a whole bunch of naughty, horny (and usually married!) men get together while their wives are away at church ;-) Now, whenever you are bringing 20 to 30 men together to gangbang a high heeled, crossdressing cumslut like me, one of the most important things to consider is discretion. I mean, what would all those prudish goody goody wives think if they found out what their husbands were doing with my warm, wet mouth and puckered lil asshole while they were reciting prayers and singing hymns!

Without fail, one of t... Continue»
Posted by cdsexslut 2 years ago  |  Categories: Group Sex, Shemales, Taboo  |  
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Allison and the Anatomy Teacher

Having recently turned 18 and exploring her sexuality with numerous hung black men, Allison the sissy boy slut was a senior in high school and going to her favorite class, Anatomy. Now, Allison is not a fan of the class as much as the hot older woman teaching it. Her name was Mrs. Ann. The anatomy teacher, Lisa Ann (not the famous porn star but did have an almost identical body) was an older woman but very fit, toned, and curvy in the right places. She was about 5’7, 130lbs, shoulder length dirty blonde hair, 34DD titties, and a bubble ass complimented by her toned legs and her preference of w... Continue»
Posted by AllisonCumms 2 years ago  |  Categories: Anal, Mature, Shemales  |  
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Finding a Great Roomate

I had just moved to the Great NorthWest and was lucky enough to land a job as a convenience store clerk working a shift from 8pm to 4am. Money was tight so I went to the classified to look for an apartment to share. I found one that was fairly cheap and close to my job. It was a two bedroom apt. and I would share the kitchen and common area with my roommate. I gave the guy a call and set up an appointment to see the apartment and be interviewed by him. I went to the address and rang the bell. The door was opened and there stood huge guy, well over 6' tall and I would say around 260lbs. H... Continue»
Posted by rikki50 2 years ago  |  Categories: Gay Male, Shemales  |  
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Sweet transvestite

Sweet transvestites from transexual transilvania.......sweet transvestites..... I don't know about you but I love Rocky horror picture show and in particular I really love that song, why you ask? well for starters it has to do with the fact that I myself am a transvestite a crossdresser if you will and yes I am still one even though I have not dressed in a couple of years, see the thing about being a TV/CD is that you will always be a TV/CD. No matter how straight you try to act, how many times you purge that feeling will never go away and it will creep up on you again and again, and this is b... Continue»
Posted by alex_boycd 2 years ago  |  Categories: Gay Male, Masturbation, Shemales  |  
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Fitting Room Fun

It’s about 8:45 at night and I am at this department store looking for some new clothes for the weekend partying. There weren’t too many people in the store, just an older married couple, a few employees, some teenagers, and a mother with her k**s. As I am headed towards the jeans/bottoms rack I notice a girl in some skinny jeans bending over. She had a cute little ass and a thin, slender body. She was pretty short about 5’4” with hair just down to her neck. I was about to walk up to her when suddenly she starts heading in my direction. That was when I noticed that she wasn’t a girl at all, bu... Continue»
Posted by pleasurenfun 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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Sissy gets creamed in Chicago

I spent last weekend with Marla in Chicago so she could catch up with some old friends. When we got there Friday night and Michael opened the door to his apartment, I could feel my cock start to get thick and harden up just looking at his handsom face and tall slender body. Once inside he offered to fix us some drinks while we made ourselfs at home. Marla and Michael were getting caught up since the last time they were together and every now and then I caught Michael trying to sneak a peek up my skirt, so I'd flash him a little peek now and then, which got my cock real hard and leaking out ... Continue»
Posted by slipn2panties 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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Allison the pool slut part 2

After using and abusing Allison’s white asspussy, and giving her a refreshing and kinky golden shower, Jay informed her that they weren’t done being kinky yet. He was not lying…

Jay’s hand gently grabbed Allison’s and pulled her to the house. Their intense poolside fucking had left Allison’s teen butthole full of warm seed and as she followed him inside it began to run down her thighs and her strappy stripper heels. “Go on up to my b*****r’s room and put on some of yo sissy stockings babygirl.” Jay commanded. Like a good white whore, Allison’s heels clacked on the hardwood floors as she did... Continue»
Posted by AllisonCumms 2 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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All His Fantasies Come True

It was a hot summer day in late June. Kris was headed off to a concert that featured all of his favorite bands. He arrived at the outdoor venue where the concert was being held and got in line to get in. While standing in line Kris started looking around. Two women caught his eye. They were standing together holding hands. Kris smiled at them and they smiled back. Kris had always thought that lesbians were hot, but he had never seen them in a public setting before.
Kris had a secret fantasy of having a threesome with two lesbians. He always knew that it was a long shot though. After standin... Continue»
Posted by sweetb84 2 years ago  |  Categories: Group Sex, Shemales  |  
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Spit roasted in an Adult Theater

One day I was feeling particularly horny from not having any satisfactory hookups in quite some time. So I showered and shaved my legs smooth and slipped on a pair of bright pink bikini thong panties. I put on a pair of sweat pants that I could easily slip off and just put on an old sweat shirt as a top. I then headed off to a popular adult theater a few towns north of where I live, about a 45 min. drive away. I paid the $10 admission, got my ticket and walked inside the theater. I immediately headed for the back row and sat down in the last seat next to the wall. Next to me on my left w... Continue»
Posted by rikki50 2 years ago  |  Categories: Gay Male, Shemales  |  
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Late Night In The Office


It was early spring in London, England. The sky was clear and sunny but there was a cool breeze coming off of the river Thames that caressed Mica’s bare long, slender legs as she stepped out of her sports sedan.
“Oh bugger, why in the world did I wear such a short dress today!” she said, cursing the unseasonable cold day while at the same time trying to hold the hem of her skirt from rising up her legs further then it already had.
Mica Doren started working for Thames Incorporated as a professional administration specialist right after she graduated from a local university, but back then... Continue»
Posted by heatround01 2 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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Exploring who I am

It took me years to realize what I was, and understand my sexual identity. My name is Rachelle Baxter, though I prefer Ray. I’m what you call a hermaphrodite; I was born an even mix of boy and girl, my facial features were even I have dark green eyes glowing red lips and an average size nose. My hair is girly, long, straight, and deep brown and lucked out with very little body hair. My torso and arms are big like a boy’s but slims down at my waist. My feminine legs are beautiful and my ass plump and meaty.

Before my birth, my mother and father had been informed I was going to be a girl.... Continue»
Posted by rachellebaxter 2 years ago  |  Categories: First Time, Masturbation, Shemales  |  
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Sissy payment in kind

My wife had gone away for the weekend to stay with a friend so I had the weekend all planned out. I couldn't wait to get home from work, dress up in my wives stockings and play with myself on Skype while an online admirer watched and played with himself. So there I was was wearing her black silky hold-ups bent over in front of my webcam with two fingers in my arse working my way up to the large dildo I had waiting when there was a loud bang on the door!

I panicked a slammed down the laptop lid and threw the dildo and lube I had out under the sofa. The banging on the door continued so I wen... Continue»
Posted by garystephens1981 2 years ago  |  Categories: First Time, Group Sex, Shemales  |  
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How I want fucked

I show up to my apartment after too many to find my new neighbor had a few, as well. She is doing better than me, but clearly hornier.

I bring her inside, light the candle, play some music and try and be sensual. Grab some drinks, and get ready for as little talking as possible.

The lights in my room are off, and she says to keep them off. She wants a back rub.

I don't even know her name yet, but I leap on without asking. Her shirt is off, her skirt is still on, as are her panties and bra. I rub the shoulders, I rub the neck, I kiss the neck, I kiss the ears. I lick down the b... Continue»
Posted by getdown 2 years ago  |  Categories: Anal, First Time, Shemales  |  
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