Shemales Porn Stories
Page 73

Shemale Public Bondage Fantasy

It was a chilly evening, I had arranged to meet him in the city centre. I was wearing a rather skimpy black dress, black lingerie and red high heels. It was my first time dressed in public like this. He was an average looking man, he shook my hand and kissed my cheek, and asked if I was ready. I affirmed, and then he led me to the park in the city. I noticed he had a small bag with him. He opened it and took out several pieces of rope. 'You know what we agreed', he said. 'Yes, I understand,' I nervously replied. I had signed up for an evening of public humiliation at his hands. He led me to a ... Continue»
Posted by barefoottransnude 2 years ago  |  Categories: Anal, BDSM, Shemales  |  
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Oh Joy Oh Joy

So its a Friday night and I'm ready to hit the town for a drink, I'm dressed to kill in a t-shirt and jeans not really looking for anything other than a drink. I walk to my local and order a beer knowing that some friends Will be here soon, well 3 beers later and still no-one is here i make a few texts and realise that they all are doing they re own thing tonight so I'm on my own till i spot a red haired girl at the bar, she seems to be on her own and she catches me looking at her and gives me a wink. I smile back and lift my drink and mouth to her over the loud bar would she like me to buy he... Continue»
Posted by mrspankytoyou 2 years ago  |  Categories: Anal, First Time, Shemales  |  
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My one and only experience with a tranny/shemale

One Friday night I decided to take a ride to Hollywood to check out adult theaters as i had always gotten my cock sucked at different adult movie theaters. As I parked my car on a side street i walked to this one particular movie theater I found myself at entrance and paid the 5 bucks to enter. as you all know, when you go into any movie house, its always dark and you wait for a few minutes for your eyes to adjust to the surroundings. i was standing near the entrance and looked around to find an empty seat. i always look to find one in the back near the isle, but they were taken, so i went... Continue»
Posted by 1superhornyguy 2 years ago  |  Categories: First Time, Mature, Shemales  |  
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Careful not to cum too quick!

I'm a 42 year old married bisexual guy, slim built, average height and shaved below. I've had a few encounters with other men but none dressed as a Woman. I've had fantasies for years about wearing women's clothes and make up. Unfortunately I haven't had much opportunity for either, that was until a few months ago.

After my initial encounter I took a little more time to plan my next step. I'd had time to reflect about my first time experience, some things had gone well some not so. Next time I decided I would plan everything a little better, making sure to do a better job on my make... Continue»
Posted by jimbo70xyz 2 years ago  |  Categories: Anal, Fetish, Shemales  |  
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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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