Shemales Porn Stories
Page 82

Riding the Lakefront-Chapter 2

August 13, 2008...8pm....Rec lot...Irving Park Rd...Chicago lakefront bike path

The event that actually changed my life began when I needed to piss about 6:30pm while on my bikeride. Tightfitting bike shorts were worn because of the padding in the ass area. But had I worn a pair of shorts with a zipper, none of this would have happened. Had I not worn a zippered tight biker shirt with my 48D tits showing, this might not have happened. But, it also was extremely hot and to be zipped up would have been ridiculous. 95 degrees, humid...typical August summer late afternoon/evening. Even a... Continue»
Posted by titsR4abuse 3 years ago  |  Categories: BDSM, Interracial Sex, Shemales  |  
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Sissy slut training ends in 3 BBCs final chapter

Well after getting fucked in the car park on the front of the limo by the driver my arse is ready to be fucked by my three black bulls.I have been waiting a long time for this and now I am ready for to be fucked like a slut my arse is Gunna get stretched to it's limits by these black studs cocks .The limo pulls up outside the apartment and my heart starts pounding so hard with excitement I can't wait .We go upstairs and as soon as we get in the door I'm sorounded by all the guys they are kissing me on the neck and in the mouth they take turns stiking there tounges in my mouth .But misstress x... Continue»
Posted by foxxiroxxi 2 years ago  |  Categories: BDSM, Interracial Sex, Shemales  |  
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First Sissy Fuck Part 3

With cum leaking out and slowly dribbling down the inside of her thighs, she kneels and starts to take long and slow licks up the length of my wet cock. Then she teases the tip with her lips and slides a finger into my ass.
The feeling is delicious.

'Good girl' I say 'Let me take off the cage'

I sit on the edge of the bed and she stands in front of me with her sissy cock level with my face, I can smell a mixture of sweat, cum and perfume, I can see veins pulsing as she is obviously very aroused, and there is a bead of pre cum on the tip. When I unclip the cage her cock springs out and ... Continue»
Posted by honestjohn1962 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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Aint a woman that comes close to you

Angie slipped in the room for our occasional discreet encounter. This time she was dressed as a hot MILF wearing shoulder length blonde hair, dark red but lightly painted lips, trimmed dark eyebrows, lightly dusted eye shadow and rosy painted cheeks. She wore a pearl necklace with a white dress that covered her arms and stopped at her knees with nude colored hose and white heels. She wore two diamond rings that highlighted her freshly manicured fingers. “You look so sexy today” I whispered in her ear as I brushed her hair back and tasted her shoulder with my lips. She turned pressing her lips... Continue»
Posted by Zeffer1 3 years ago  |  Categories: Shemales  |  
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She dresses him like a slut

My cock was as hard as it could get when Jaime came in the room. I could feel the moist pre cum rub on my thigh. Carol had made Jaime up to look like a total slut. Jaime had dark brown shoulder length hair, thick shades of blue that ran from the drawn on black eyebrows to her to long black eyelashes and around the bottom of her eyes, her lips painted pink with a thick coat of lipstick. She wore a tight black strapless cocktail dress that just covered her sweet spot with black nylons that had a thin dark stripe down the back stopping at her sexy black high heels. “Suck his cock now” Carol barke... Continue»
Posted by Zeffer1 3 years ago  |  Categories: Shemales  |  
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I posted a craigslist ad.

8 years ago I began crossdressing again and playing with toys. After playing one day while watching videos online I decided I wanted to take the next step and be with a man again. My holes craved it but the butterflies in my stomach had stopped me before. Afraid they would do it again this time I got dressed as slutty as possible and put up an ad on craigslist with a photo of me dressed and spitroasting myself with toys. Pic required I put in the posting. I was amazed at the responses and how many people couldn't read or just saw the photo and replied without reading. I didn't think it w... Continue»
Posted by bibottomboi 4 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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TV loving cock

Sorry I didn't keep you posted on Saturday night, but I was sorta busy being my usual slutty self. Story to follow:

I talked to a guy on megaphone. He works as a night security guard at a big office building on the edge of town. He is there all by himself in this huge, mostly vacant building, in a safe area, so there really isn't anything for him to do but set around and be horny. So he was looking for someone to come over to his job and get nasty.

Naturally I was just the girl!

I'm all dressed up in one of my hottest outfits and looks, so I jump in the car and race over. It takes m... Continue»
Posted by jenn1 4 years ago  |  Categories: Shemales  |  
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My step mom turned me into a sissy slut for dad

When I was in High school I would spend the summers with my dad and step mom. She was so hot and always dressed sexy, They were always very playful about sex, not like my mom and step dad. I loved the atmosphere.
During the week they would work all day and I would have the place to myself. I would always go into their room and see what I could get into. I found some picture of the 2 of them nude. Well after that I was always in their room jacking off to the pictures of my step mother naked. Little by little I would find other thing to help with my fantasies. I got into her dressed and wou... Continue»
Posted by firstknightd 3 years ago  |  Categories: Shemales, Taboo  |  
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My first threesome.

My lover and I just finished sucking each off and were laying next to each just talking and he ask if I had any fantasy's and I said I like dressing in lingerie. He went to his closet and came out with a black bra and panty set along with a full black slip. He asked if I would put these on and I was up so fast I tripped and fell to the floor. I didn't think I made any noise and started to get dressed. He went into his bath while I was dressing and then his bedroom door open and in step his step mother. I didn't know what to do but stand there in the lingerie. She just smiled at me and wa... Continue»
Posted by billieearls 3 years ago  |  Categories: Gay Male, Mature, Shemales  |  
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A recent dream

The following is a note that I sent to my girlfriend of 20 years about a dream that I recently had:

My dream started out with you kissing me goodbye as I left in the car for some conference in a big city. I wasn't fully aware of where I was going other than that I was going away for a couple of days. When I arrived at the hotel and checked into my room, I put two suitcases up on the bed, which was strange. I stood there wondering why I had two pieces of luggage. I quickly opened the suitcase that I remembered packing which had my toothbrush and change of clothes for the day. It had bee... Continue»
Posted by sleeplessone4u 2 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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My sissy son by his dad and lover Part 5

Well...what a few months it's been since i/we last spoke to you.Many things
have happened,some of them great,some fantastic..some not so good,best tell you!

Lucy and i are in love,no two ways about it,we found out how to change her name by deed poll(to legally change your name in the UK)So she's now,legally..Lucy Alice Andrews and she wears a matching wedding band and engagement ring like mine.I wear just the band when we go out together,as i said..she passes for a woman no problem.So people just think i'm a guy with a younger/sexier trophy wife,(which in a way is right!) She dresses as Lu... Continue»
Posted by chocandres 3 years ago  |  Categories: Anal, Shemales, Taboo  |  
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My night of first times!!!

I was sitting in the bar with my friends when she walked in. Black short dress, low cut neckline. I can see the garter straps holding her stockings. I think that is what caught my attention first. I had seen garters and stockings in movies but never in real life and her legs looked great. I couldn't keep my eye off her all night. I had to seem like a stalker with my eye's, I wasn't paying much attention to the conversation at the table with my friends she was lust at first sight. I had to make a restroom trip and when I walked out she was standing there. My heart skipped a beat and my stomach ... Continue»
Posted by Trudru 4 years ago  |  Categories: Shemales  |  
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Daddy's lil bitch

As a young boy growing up I always had a fetish for dressing up like a girl. When I was 20yo I had my first experience with an older man, Tony a man in his 70s. I met him through a phone chat line and we seemed to hit it off right away. He told me that he would buy me some clothes and lingerie to wear for him when we met. So after a couple weeks of phone chat I mustarded up enough courage to meet him face to face.

When I arrived at Tony’s house he greeted me with a warm hug and kiss. Tony was a very handsome man, stood about 6’ tall and clearly looked like he took good care of his body. He ... Continue»
Posted by aznfemboi 3 years ago  |  Categories: Gay Male, Mature, Shemales  |  
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So you know women...

I was in another state in an extended stay motel for spring break. The girls were hot and the guys were hotter, I did not know which way I would go on this trip.

I had noticed two females that seemed to be daughter and mother, they would come in early morn and stay in their room. The young girl was close to my age and very light skinned, the one I thought was her mother was some what darker and had a heavier build.

One morning I was returning from an all night party and was just a little bit d***k. I saw them as they pulled in and the elder of the two ran from the car saying someth... Continue»
Posted by d4david 2 years ago  |  Categories: Anal, Group Sex, Shemales  |  
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Ladyboy orgy in Thailand

During one of my many nights in the sleaze capital of the world Pattaya, Thailand I was at a certain ladyboy bar all dressed up in my sexiest outfit that the “girls” had ask me to wear in as I had shown them some pics of me dressed. Not that I could ever hope to compete with any of them!

Chatting away with one of the girls a German guy came over to us and said that he having a “party” up stairs and if we would like to join him and his friend. I assumed he just meant the girl from the bar and told them to have fun and she went off with the German guy. Just as they went threw the door lead... Continue»
Posted by toniparr 4 years ago  |  Categories: Gay Male, Group Sex, Shemales  |  
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POP GOES THE CHERRY

POP GOES THE CHERRY

I recently read a delightful account of a young gurl loosing her virginity to a f****y friend. Got me thinking about loosing my own virginity.

First, you should know, my mother made me a sissy. She took great delight in dressing me as a little girl, thinking back I can not remember when she did not. We lived in the country and most of the time growing up I played outside with my dolls in dresses. The only time I wore little boy’s clothing was when f****y visited or I went to school.

Everyone in town knew I was a very sissy acting little boy. I was bullied a ... Continue»
Posted by littleoralvee 3 years ago  |  Categories: Shemales  |  
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Halloween fun

Here's an interesting story that happened to me last Halloween, hope you like it. Last October, a local bar had a Halloween costume contest. Since I had nothing better to do (I'm too old for trick or treat) I decided having a beer and checking out all the silly costumes would be fun. I sat near the bar and almost immediately a sexy, slinky brunette caught my eye. She was wearing a light blue dress, black seamed stockings, and dark brown "fuck-me" pumps. After a short time I went over and said hello. She was smart and funny, and we really seemed to get along nicely, but with the loud musi... Continue»
Posted by throbbinghardboner 3 years ago  |  Categories: Gay Male, Shemales  |  
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Chronicles of Amy, Episode 1: The Beginning

Amy is a part time transvestite who enjoys to dress very sexy and go out and have some fun. So a few years ago, on a Thursday evening, she was sitting in her favourite cafe, looking at the poeple passing by, flirting with some attractive males, who were charmed by her appearance. She was wearing black fishnet stockings, 4 inch black leather high heels, a miniskirt that was barely covering her perfect ass and a white, very tight top. The cafe was quite full and so basically the only free seat was the one next to Amy. She was enjoying another bit of the chocolate cake she had ordered before, so ... Continue»
Posted by SweetAmy 4 years ago  |  Categories: Hardcore, Interracial Sex, Shemales  |  
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Chrissie's New Client

I run a small investment consulting firm. Very small, actually it's just me. It's really just a cover business for what I really do which is to service my male clients clandestinely.
There are an average 20-25 active clients. They are all successful proper business man, many of them you would classify as professionals.
They are all referrals and have been carefully screened. Most of the men are straight but just like a girl with "something extra"occasionally. There are also some who I suspect are Bi-sexual. I don't really cater to the overtly gay community.
That's for no particular reason ... Continue»
Posted by chrissieCD 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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Cheri

My name is Cheri, I live my life in lace and satin. I have always loved the way those materials feel against my soft skin. I have shoulder length red hair and bright green eyes. My friends used to call me Charles but about 12 years ago i had this epiphany that i felt out of place as a man and one night while I was out at a club with some friends, I realized that being a woman felt... I don't know, right,
to me I guess. It's been a long road but I'm so much happier now.

The first time anyone ever found out I had a dick after that was about 10 years ago. I went to a new doctor for some ant... Continue»
Posted by LadyShi 4 years ago  |  Categories: Anal, Shemales, Taboo  |  
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