Shemales Porn Stories
Page 13

Abused as a tranny at a sex party with my mum

This story is a follow up to "Caught wearing my mother's stockings"

I decided to go to the party and be the tranny slut they were looking for. After all, it's nice to be wanted and I really would do anything to keep those photos of me dressed in my mum's stockings, private from my friends.

I've never had anything up my ass before, in fact I've never even had sex at all. This was going to be my first sexual experience. Unless you include being wanked off by my mum or kissing and groping fat girl, Stacey Williams at the school Christmas party. So the idea of being the centre piece at a sex... Continue»
Posted by petearch 3 years ago  |  Categories: Hardcore, Shemales, Taboo  |  Views: 3795  |  
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Caught by a neighbour in my s****rs clothes.

It was 10 o'clock on a Friday in late June of 1997. My parents were away visiting relatives for a few weeks. My s****r Kate had gone out partying with her friends for the night and wouldn’t be back till Saturday morning. Which left me all alone in the house.

For as long as I could remember I always loved dressing up in my s****r's clothes. When I was lucky enough to have a whole night with them out of the house, I usually went all out in my s****r's room. ??
I had been shaving what little body hair I had for years. I used to lie and tell anyone who noticed that a lot of swimmers and athlet... Continue»
Posted by kara_zor_el 3 years ago  |  Categories: Shemales  |  Views: 3775  |  
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My First Girly Cock

It was cold. I was running fast so that I could not get too wet by the falling rain. The streets were quiet, because everyone was inside. It was twenty minutes before midnight. I was nervous. It would be my first time I'd have sex with anyone other than a woman. I love women. I'm in love with them. I don't consider myself being gay, but I always had that ardent lust to be with a transsexual woman. I just couldn't get them out of my mind.

This passion started a couple of years ago, while I was surfing on the Internet looking for hot stuff. Immediately I felt something. That first time, when ... Continue»
Posted by jimpgr 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 3770  |  
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My shemale boss part 1

I knocked at my bosses door and on her reply went in. She was standing with her back to me looking out of the window and talking on the phone.

She failed to agknowledge me so I just sat down in one of the leather chairs opposite her desk. I looked at her as she stood by the window and perved over her black stiletto leather knee high boots and tight black leather skirt which covered her ass beautifully.

After about five minutes she turned to me, her black hair to her shoulders and her black shirt partly Unbuttoned showing off her cleavage, it has hard not to get a semi hard on as she move... Continue»
Posted by big_rob49 1 year ago  |  Categories: First Time, Shemales  |  Views: 3767  |  
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My 1st interracial threesome

I met a guy and he came to my hotel after meeting him on a social network site. He was 6'2 and around 225 pounds military man. We instantly hit it off when he came into my room and gave me a passionate tongue kiss. He then dropped his pants and I sucked his hard 7 1/2 inch cock, he then ate my sweet ass pussy until I couldnt take it any more. Then he topped me and gave me a huge load. About 3 weeks later, he said he wanted some more, I told him that I was super horny and always wanted a 3sum. I was house sitting for a friend and after we emailed each other for about an hour, he agreed to have ... Continue»
Posted by charlie39212 6 months ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  Views: 3763  |  
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What If My Mom Part 2

Peggy and Me

We all lay together for a while until Mom told us she had to get up, it was lunch time. We had not heard from Bobby or Dad and I was getting hungry. "You two just stay here, I will make some sandwiches. Back in a minute"

Just as Mom left Peggy rolled onto her side facing me, "That was so nice kissing your Mom.........., will you kiss me, down there?".

My feelings were still mixed up, but I did want to. I could show her what Mom had taught me. When I moved to get between her legs she stopped me. "No together, I want to suck your cock at the same time, you know".

Peggy p... Continue»
Posted by chchboy 2 years ago  |  Categories: Group Sex, Shemales, Taboo  |  Views: 3757  |  
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The mom who sneaks behind the door.

Hi im james and im 20 years old my mom is in her 50s with a larg rack big booty thin tight abbs and long smooth legs blue eyes and long hair aways weres pantie hoes and skirts and coresets and long red hair.
any way I was on my way home from school at night i got home mom was a sl**p i was on my lap top looking up porn watching this black chick lick a nother chicks ass hole i turnd all the lights off and started rubing my cock.
but as the black chick licked the other chick ass she moand so load some wan els came in will there eyes wure closed she was wearing a skirt and coreset.
she was bla... Continue»
Posted by gothicslave 1 year ago  |  Categories: BDSM, Lesbian Sex, Shemales  |  Views: 3753  |  
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He caught me in his wife's cloths

I do odd job's and I was about to do one for my wife's best friend Tina and her Husband Phillip. I went over and looked at the job. I told her it would take several days and that I could do the work while her and her husband were at work. That way I wouldn't be in anyones way. Well the first day of the job I showed up just before Tina left for work. Pillip was already gone. We chatted a while the she left for work. Tina is really very hot and I have wanted to fuck her for a long time. Sense i knew that was not going to happen I thought I would do the next best thing. I went stra... Continue»
Posted by firstknightd 4 years ago  |  Categories: Shemales  |  Views: 3752  |  
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My first encounter with a shemale!

I am a straight guy who had never strayed before.. however i had been having urges over shemales and started wanking to shemale porn every now an again online. i have always been interested with my ass being explored but i never found men attractive. with shemales it was different. they are beautiful, slender but also filthy at the same time. it seemed perfect

i had planned a europe tour some years ago and my first stop was amsterdam. after a few hours of roaming the red light district i was very horny and i soon found the 'blue doors'

in one of the doors was a gorgeous shemale from braz... Continue»
Posted by onceuponanas 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 3742  |  
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Meeting with the Boss

I arrived to work to find out that my boss wanted a meeting to discuss my future with the company. I wasn't sure if this was good or bad. My boss, Erica, is a very beautiful woman. She is hispanic with bronze skin. She resembles Eva Mendes and is about 5'7" tall, 130 lbs with great curves. She always wears tight skirts and blouses. I entered her office and she told me to sit. After talking for about 20 minutes I was thinking this is good because I would have been fired immediately.

She then asked me how dedicated was I to her and the company. I said very dedicated and that I love working he... Continue»
Posted by swordlvr69 2 years ago  |  Categories: Gay Male, Shemales  |  Views: 3734  |  
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foxxiroxxi gets fucked by a black bull at a costum

I was invited to a costume party by a good friend of mine named lexi , she has been my friend since we were k**s and knows i love to dress up as a women from time to time so she invited me and i accepted . The theme of the party was tight and short so unless you had the dress code on you dont get in . Lexi and i had to go shopping for new outfits to wear , we head straight to this dress shop that only has sexy club wear and dresses that only just cover your privates which was exactly what we wanted . Now both us were going to this party looking like two girls that wanted nothing more than cock... Continue»
Posted by foxxiroxxi 1 year ago  |  Categories: Fetish, Interracial Sex, Shemales  |  Views: 3715  |  
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Wife Shares Shemale

"Where are you?" Tara asked in a high pitched voice as if she was either excited or freaked out. "I'm at the boutique" I replied. "Ok I am coming by, something very important. I am so freaked out now and I will tell you all about it when I meet you. Will be there in half an hour see you." She hung up.

The phone call made me really nervous.I had reasons to get nervous if not get a nervous break down. Tara and her husband owns a few restaurants in different cities across the States. I have known Tara since 6 months now since she busted me from one of the restrooms of her restaurants. Well wh... Continue»
Posted by drew1207 4 months ago  |  Categories: Anal, Fetish, Shemales  |  Views: 3714  |  
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TV Beginnings - Caught by Neighbour

I started crossdressing at quite an early age, 'borrowing' items of my mum's underwear and furtively dressing in them when she was at work. As I was an only c***d, and mum and dad had separated, I had quite a lot of time to indulge my little hobby! I used to love wearing her tights, the sexy feel of them encasing my legs and cock, and the way they made me feel so girly when I admired my reflection in the long mirror in our hallway. I would also wear her big full-cut knickers and doreen bra, and complete this with a lace slip and a pair of strappy heels or mule slippers that I could fit into th... Continue»
Posted by sparkyking 25 days ago  |  Categories: Gay Male, Shemales  |  Views: 3718  |  
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It doesn't get any better than this!

15 years ago, I went into my older b*****r's room to grab a porno mag. He had stacks of them all over the place. I wasn't too choosy. I picked the magazine off of the top of the pile that was closest to his bed and went into the bathroom. My usual routine was to open the mag, find a babe, pull out my cock, and have at it. When I opened the mag, my jaw dropped and my dick got so hard, so fast it practically popped out of my pants! I could not believe what I was seeing! It was a gorgeous babe alright, but she had a BIG hard-on where her snatch was supposed to be! My cock was pulsing in my pants,... Continue»
Posted by bugaboobed 2 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 3702  |  
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TRAP

I was dating this 27 year old fox. And I was luvn it. You See Im 44 years old a lil overweight and I have a 5 inch cock! So you can imagine my surprise when I picked this little honey up at the bar d***k and the next morning she didnt want to leave!
The first night I got her home and we dove into bed Im 6ft 230 lbs with strong arms and long flowing hair We sucked each others tongues at first. I felt that tight body up and my lil boner was diamond hard. I got up to get her a liquor drink and I let my eyes feast upon this 5ft 8in beauty 115lbs of pure sin. She wore a size six shoe and had a bi... Continue»
Posted by playingroles 1 year ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 3693  |  
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this year Dr. visit

My Annual Dr'S Visit 2014

i guess I'll describe this years visit and if you like reading them I'll continue to describe my annual Dr. Visits. I've been seeing the same Dr. and his Nurse for about 4 years now. The first one was mostly normal however the last two previous ones have been kind of embarrassing for me and I wondered how this year's would be. I made my appointment and and as usual the nurse came to the waiting room and got me and took me back to the exam room. She had me go into the changing room to put on the gown . I took off my shorts and top exposing my bra and panties like ... Continue»
Posted by sissygirl 5 months ago  |  Categories: Gay Male, Shemales  |  Views: 3676  |  
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Bi male and anal sex

Thru out my adult sex life I have always enjoyed having my ass teased and played with. 
Then I started dating a woman whom loved to tease a mans ass with her fingers, yes fingers where she quickly got me use to taking 2 of her fingers. 
Then one night things changed. After a hot night of wild sex, she slowed things down before excusing herself. But before she left, she rolls me over on my chest, which to me means she want to tease my ass. I hear her in the bathroom , toilet flushes and I hear her returning to the bed, straddling my legs, she racks her fingers up and down my back before she l... Continue»
Posted by rogue-1966 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 3676  |  
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CD at truck stop with three men

Went to a truck stop last night after a party around midnight in my sexy short dress, got out and bent over looking at my tires for assistance. Gave a nice view to whoever was watching of my smooth white ass and sexy black panties with pink trim with half of both cheeks exposed. A nice older (63 yo) black guy (Ted) asked me from his truck if I needed help. We talked and then thanked him and asked if I could help him for helping me.

We walked over to his truck and got in his sl**ping quarters. Gave him some more intimate show of my nice ass, turned around, unzipped his pants and began ... Continue»
Posted by hotcdsub 2 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 3669  |  
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Letting my neighbor see me jacking off!

Yes, i am lucky to have a hot neighbor, a guy who likes to watch me when i am outside, in the yard or even geting into my car, it seems that when i go outside, there he is! So, why not give him what he wants, whether he knows that i am a shemale with a hot 7 inch cock, or as he might think, a girl with a wet, pink pussy. I know he jacks off to me, i did see him in his upstairs window last month, shades pulled up, jacking his big cock off as i wa outside in shorts up to my ass. He shot a load on the window and i know he knwos that i saw it all. so? My turn! Shortly thereafter, i went outside in... Continue»
Posted by cumsquirter 3 years ago  |  Categories: Shemales  |  Views: 3655  |  
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Unexpected friends CD fantasy

There really wasn't any planning to what had happened. Earlier that weekend, I had just felt this strange urge, so I decided to check online for something different to do that was new. Of course, I had done parts of this before, but most of them were separate in their operation. I had never done anything sexual with anyone, though I had posed, and the only time I had gone out as this was to see if I would be recognized. Maybe that was what convinced me to except his offer, as I somehow felt that I wouldn't be recognized by anyone locally.

So I had agreed to meet with a man at 8pm in a rathe... Continue»
Posted by RosalynLee3 6 months ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 3652  |  
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