Shemales Porn Stories
Page 9

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: 3766  |  
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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 2 years ago  |  Categories: Hardcore, Shemales, Taboo  |  Views: 3761  |  
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Tina trap

A few days after he fucked me so masterfully that day, my friend's older associate invited me to visit him at his apartment. I wasn't sure what to do. Originally I had only had been with the one guy and now he seemed to be passing me on to his business partner. When I asked him about it he told me that he was OK with it. He had done this before: found a young guy and then introduced him to his older business contact.
So I had been used all along. I was just currency.
But I had liked how Mack - the older man - had fucked my ass. And I didn't want to NOT be fucked any more.
I accepted Mack'... Continue»
Posted by dlcalguy 6 months ago  |  Categories: Fetish, Group Sex, Shemales  |  Views: 3762  |  
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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 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 3746  |  
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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 1 year ago  |  Categories: Group Sex, Shemales, Taboo  |  Views: 3741  |  
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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 1 year ago  |  Categories: Gay Male, Shemales  |  Views: 3730  |  
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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 2 years ago  |  Categories: Shemales  |  Views: 3711  |  
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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 1 year ago  |  Categories: First Time, Shemales, Taboo  |  Views: 3706  |  
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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: 3706  |  
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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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My first tranny

I had never been with a tranny before and did not plan on being with one at all but you never know what will happen. I had a bad day, I had been in meetings all day with new clients in another city. I decided to stop for a drink or two before going back to my hotel room. I found this bar that look interesting so I went in. There were lots of beautiful women there so I thought that maybe I would get lucky and not have to be alone tonight. I went to the bar and ordered a drink and checked out the room. Like I said there were lots of beautiful ladys there but one caught my eye. She was not too ta... Continue»
Posted by wildbill975 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 3673  |  
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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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A busy Friday night. [CD/Gloryhole/neighbor]



I had been looking forward to this weekend for a month. My wife was going to visit some friends in NYC, and I was staying home, by myself. Yup, just me and all of my favorite things, like stockings and panties, and sexy little outfits. The torture was finally over, and the Friday she was to leave, arrived. I was still at work when she called me to tell me she was on her way up rt. 95. I wished her safe travels, and told her I would talk to her tomorrow.

I immediately left work, and headed for my car. I was so excited that I practically ran out of the office. I was going to indulg... Continue»
Posted by pbg732 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 3650  |  
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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 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 3645  |  
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becoming Rachel

I was about 15 when i found a bounty of porn magazines and female lingerie in the park near my parents house. Without thinking at all i grabbed it and took it home. that night after getting horny reading some of the porn magazines I tried on some of the stockings and silky lingerie. it was the sexiest feeling i had ever felt. they seemed like a natural fit for me, as i had a slim and somewhat girlish figure.

Over the next few months i regularly played with myself while dressed up and reading the mags. but after a while, without the magazines, imagining I was a girl, with my legs spread wi... Continue»
Posted by rachel_cd 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 3644  |  
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Me and my part time job

I was always doing part time jobs to help the f****y with the bills, I was the youngest of 10 k**s ,but the only son. As I was walking home from school one day This guy asked if I was looking for a part time job that he had to clean out his basement and garage I was very very happy to say yes I'm always looking for extra money he asked me to come in. The Large house had a lot of antiques in it, The man "James" introduced me to his wife "Diane". We went into the kitchen for coffee and what they needed me to do then she kissed her husband and went to work.

James said that the junk was going t... Continue»
Posted by sissytimmy 7 months ago  |  Categories: Gay Male, Shemales, Taboo  |  Views: 3635  |  
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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 1 year ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 3635  |  
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The Girl? Next Door

A knock at the door, it was her of course! She came in and look a little d***k too, we sat and talked for a short time. I was wearing shorts and she noticed that my dick was slowly get a semi just checking her out. Thats when i noticed her hands go down on to my shorts where my dick is, she looked at me licked her lips knowing that i wasn't very experianced told me tonight she would be boss, i eagarily agreed. She took my pants down and while kisses me was rubbing my cock up and down, wow this felt amazing the way she moved on my cock was almost as good as me, she wet her finger and while... Continue»
Posted by ts_lover69 3 years ago  |  Categories: Shemales  |  Views: 3629  |  
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SHEMALE SURPRISE

while in our early teens my cousin nicolas and
i used to look at porno mags and videos up in my
tree-house which was quite a ways from any other
structure. during these sessions nic and i would
whip out our young hard-ons and whack off to the
images of naked women and men of all ages. we got
together to do this about once a week and discuss
the sexual escapades we may or may not have had
with girls we went out with during the week. a week
after nic had graduated (i was still a junior) he
came over to the tree-house and said
he was leaving for the city "to find himself."
when i... Continue»
Posted by qrystofer 9 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 3621  |  
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sissy blackmailed by teamviewer and exposed


my fantasy about being blackmailed and totally ruined

watch out this could happen to you

im a sissy faggot I live in st Louis mo im in the closet no one knows i dress in femine clothes I was married when I was 20 and straight after a year I caught her cheating on me , we only had sexy 3 times I couldn't get hard with her , I was allways thinking of men, masters, tops, at home I stole her panties bras high heels lip stick, and would dress around the house, after the divorse I got the house and I started to wear panties to work everyday and shave my legs smooth , somedays i wear stocking... Continue»
Posted by sissypattie 23 days ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 3615  |  
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