Shemales Porn Stories
Page 12

Heather's Sissy

Heather's Sissy

My husband, Bobby, is standing with his nose in the corner, quietly sobbing, as he contemplates the ill-advised temper tantrum that he threw this afternoon. His sobbing is due to a very sore bottom, for which I take credit foróalthough to be fair, my favorite wooden paddle should also take some of the credit too.

I'm not sure what it was that finally sent Bobby over the edge today. It could be the fact that I arbitrarily extended his sentence of chastity for another month, or it could be that he was upset about the date I was going on this evening. However, the ... Continue»
Posted by klammer 4 months ago  |  Categories: BDSM, Fetish, Shemales  |  

The BOLD Steward

Hi All

Just a small recap of myself. I am a crossdresser from India and living ina joint f****y and all my crossdressing sessions are done when i am travelling and alone. So here is what happened on one of my work trips last week.

I had some work in the town of Raipur in central india. I reached by flght in the morning and checked in to my hotel. i had a shower and changed and went to meet my client. i got free with the first round of meeting in a couple of hours. i had lunch with them and was free around 3 pm. I had to stay there for 4 days so I asked my cabbie to take me to a place whe... Continue»
Posted by hornyboyind 4 months ago  |  Categories: Gay Male, Mature, Shemales  |  
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Jr. Prom 3

In the morning, I got up early and was so happy, I couldn't believe it. I
had sucked cock and been fucked like a girl. Not only that, I was so good
at it, my dad was proud of me.

I had a big smile as I walked into the kitchen wearing nothing but my night
gown. My dad was sitting at the table drinking coffee.

"Good Morning... How are you today?" I asked as I lifted my gown and
flashed him some pussy.

He just smiled. "I'm 38 years old and last night I fucked the hottest 16
year old in town. Not only that. I'm fucking a mother daughter team of the
two hottest women I know. I'm here... Continue»
Posted by cire9691 4 months ago  |  Categories: First Time, Shemales, Taboo  |  
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Jr. Prom 4

When his orgasm subsided, I leaned back against the front seat again and
spread my legs wide. I had a huge smile as I watched him lay back and
relax. He had a content, dreamy look that couldn't hide the satisfaction he
had gotten from our encounter.

I could feel his sperm gurgling around inside me while his fat cock was
still buried balls deep. The whole thing was so peaceful and so

I was so proud of what I had just done, I could hardly contain my
excitement. I loved being a girl and this is what made it worthwhile.

"So what do you think?" I asked cheerfully.

B... Continue»
Posted by cire9691 4 months ago  |  Categories: First Time, Shemales, Taboo  |  
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Jr. Prom

My Jr. Prom-2


When my parents came out I was still reading stories and wishing I could
suck somebody's cock. They went into the living room and watched TV until
noon when my dad jumped in his truck and went to the gun club to do some

After he left, mom came over and asked what I was reading. I told her what
they were and we sat and read some of them together. I was trying to hide
the fact that I was grinding my pussy into the chair. While my mom tried to
hide the fact that she was fingering herself. Neither one of us did a very
good job.
... Continue»
Posted by cire9691 4 months ago  |  Categories: First Time, Shemales, Taboo  |  
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Jr. Prom 1

My Jr. Prom-1

When I was 8, my f****y moved from Chicago to the middle of nowhere
northern Wisconsin. Soon after that, I met Bob. We became friends instantly
and have been best friends ever since. We're 16 and juniors in high school

He's a jock and a sports freak. While I'm a science geek and a book
worm. He was 6'1" and 190 lbs of muscle and built like a jock. While I was
about 5'8" and 125 lbs, with a fat ass. My mom was a nurse and my dad was a
carpenter. His dad was a farmer and his mom was a teacher.

Despite the differences, we hunted, fished and camped out quite often... Continue»
Posted by cire9691 4 months ago  |  Categories: First Time, Shemales, Taboo  |  
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i cant baleave i just fucked a shemale

I was at work and the express had hired a new sectary for me I asked her I said hey crystal can u get me my papers please from my printer cause I was writing and needed to save time crystal walked over and bent over a little she was dark black I mean real black she had thick legs big booty nice thin abs big lard tits long bl**d red hair red lips bright green eyes panties hoes on red thong red dress shirt black dress suit and skirt crystal said it ok to stair I said im not im working she dropped the papers and bent over to get them opps she said then I started really staring she said see I kno... Continue»
Posted by gothicslave27 4 months ago  |  Categories: Anal, Hardcore, Shemales  |  
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Bed side manner........

I woke early the next morning for my bl**d test and after showering dressed in a black soft cup lace bra, I now filled the 38B cup and resolved to buy some larger bras that day. I slid over my feminine hips a pair of matching hipster boy shorts and suspender belt. As I clipped on the suspender belt on the lace top stockings I mused on what outer wear I could reasonably get away with. i choose a very pale, almost off white with a tinge of pink linen shirt. It was loose fitting but when close to the skin became tantalisingly just see through. I then those a baggy pair of off white cream linen tr... Continue»
Posted by LaceTops4U 4 months ago  |  Categories: Fetish, Mature, Shemales  |  
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sissy caught by daddy

I was so scared ,Dad had caught me several times dressed up in my s****rs clothes but the last time he told me that the next time he caught me the punishment would make me never disobey him ever again,and that was less than a week ago.Now here I sit on the foot of my bed wearring my s****rs satin lace panties and bra,her stockings,heels and her favorite slutty skirt and top.I had skipped school just so I could dress up and had just finished putting on my lipstick when dad walked in and caught me.He laughed and told me that the school called him because they didnt believe the lame story I told ... Continue»
Posted by sparkyking 4 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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Caught by the Neighbor Crossdressing While Home Al

Do you know a crossdresser who got caught in the act?

This is a real life story of a crossdresser caught in the act!

This happened around when I was 15 yrs. old.

As my s****rs were off at college and it was just my mom and I at our apt. I was home from school as we didn’t have any school that day. But my mom was still at work. So I got myself all dressed up looking pretty. As I thought I will make it a girl’s day in. I decided to wear a pair of my mom’s dark navy pantyhose with one of my s****r’s jean skirts and a blue and white sweater with some black 3 1/2 heels.

I put my ma... Continue»
Posted by sparkyking 4 months ago  |  Categories: First Time, Shemales, Taboo  |  
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I'm coming home.........

The text from Mistress pure;y read, "I've missed you coming home Monday midday, rest of day off" It came in Monday morning. I had had an uneventful Sunday which had allowed me to complete some washing and house work.
Monday morning was relatively plain, with the exception of a letter from my doctor asking me to come in for some tests on the following day. I rang and made an appointment for early morning.
Mistress arrived shortly after noon. She looked tired and travel weary. I had dressed plain in a grey figure hugging skirt, Hold up stockings a plain white thing, low kitten heeled sling bac... Continue»
Posted by LaceTops4U 4 months ago  |  Categories: Fetish, Mature, Shemales  |  
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la révélation

Je n'avais pas encore 18 ans et je vivais une adolescence plutôt chaotique.

Entre les conneries d'un garçon de cité HLM, les petits vols (emprunts) de mobylettes et une situation scolaire catastrophique. Je n'étais franchement pas le plus épanoui des garçons de mon âge !

Toujours puceau, je ramassais râteau sur râteau de la part des filles qui m'aimaient bien pour la plupart mais comme copain pas plus. Il faut dire que j'étais le roi de la déconne et des bêtises et çà m'attirais une petite aura auprès de la gente féminine mais en tous cas çà ne m'aidait pas pour la baise.

Un samedi so... Continue»
Posted by panbagna 4 months ago  |  Categories: Shemales  |  

Thailand part 4

Relaxing with pizzas and beers, the afternoon seemed to fly by. My mates wife came back from the beauty looking much the same and when challenged undid her shorts and flashed both of us her completed hairless cunt whose lips were parted glisten with cunt juice and bending over showed us her newly bleached arse hole and oz fag painted nails which extended her fingers by an inch or so.
Walking to their room, she called for us to get off our backsides and take her out for dinner and party. I made my excuse that it’s a work day tomorrow and needed to organise a few things for next week. Bizarrely... Continue»
Posted by daveaverage 4 months ago  |  Categories: Group Sex, Hardcore, Shemales  |  
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It was Friday night and I had had a long week work sucked my boss is an asshole and I just wanted to go out and get laid! I got myself all dolled up brand new wig and it looked amazing with my hair flowing dark red it really brought out my green eyes I painted my all my nails ruby red and matched it with some glossy non smearing lipstick the expensive king that doesn't budge even if your sucking a huge cock and I was going to be baby if I had anything to say about it...My slinky red dress and matching fuck me pumps that were so high I needed to practice walking around a little to get my balan... Continue»
Posted by laceysgirl 4 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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Sucking cocks in DC

I stayed at a hotel in DC. I put an ad up on CL to give blowjobs (put a picture of me in a teddy up). I had several responses but I chose two. The first that showed up was a 6'3" tall black man!!!! OMG!

I let him in wearing the teddy. He looked me over, pulled me in tight and gave me an incredibly sloppy kiss! As he released me, he pushed me to my knees, I thought I was going to take his cock into my mouth right in front of the door! Instead, he walked over to the chair. He told me to shut the door but not all the way and crawl over to him. Of course, I did... leaving the door op... Continue»
Posted by vickiebicd 4 months ago  |  Categories: Group Sex, Shemales, Voyeur  |  
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Best sex ever

Oh my days, I just had the best sex of my life and it was with a straight guy. I was chilling in the park after work minding my own business (checking out xhamster on my tablet) and these two black guys came and sst down next to me; lets call them Big and Bigger. There are no other people in this part of the park, which is why I like it, and I think it a bit weird they have sat next to me, but I have been craving big black cocks recently so I don't mind. They were great eye candy both of them. Big then produces the stinkiest weed I've ever smelt and says he is selling. I don't smoke so tha... Continue»
Posted by sfred736 4 months ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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league of legends

Hi this is not a story but i had an idea i am 21 an bisexuali love shemales and i play league of legends on eune server why dont we add each other and play and chat ;-)
So you know if you like shemales or guys or you are a foot fetish lover and you play games lets add each other
Please DO NOT send me friend request if you are u******e.

Hi this is not a story but i had an idea i am 21 an bisexuali love shemales and i play league of legends on eune server why dont we add each other and play and chat ;-)
So you know if you like shemales or guys or you are a foot fetish lover and you play g... Continue»
Posted by iwannis95 4 months ago  |  Categories: Gay Male, Sex Humor, Shemales  |  

Thailand part 3

I woke up sitting on the couch, feeling like shit, my arse ring was sore and my cock was stuck to my belly with dried cum. (read part 2 to find out why). I looked around and saw the carnage from the night before. Sitting opposite in a chair was my mates wife, naked legs open and her cunt lips open and red from the pounding it had from the lady boi cocks. my mate was snoring next to me (a complaint his wife sited in the divorce papers) also naked.

The room was as hot as hell and I was sweating like I had just run 5k. On the floor was 1 ladyboi flat out and I wondered were the whore and the o... Continue»
Posted by daveaverage 4 months ago  |  Categories: Gay Male, Hardcore, Shemales  |  
  |  1

The passage of Lydia Part 1 Aunty Bev

Every time I get ready to transform in to my glamorous self I always give a silent thanks to my ‘creator’ Aunty Bev. I have a few minutes to spare so sit comfortably and I’ll share a tale with you ..

I wasn’t your average 18 year old, sure I liked football, music and all the teenage stuff but I always felt different, I was somewhat taller than the rest of my peers by a good few inches, 5’11” and fairly athletic build from playing rugby and swimming for my school. But I felt different something I couldn’t put my finger on until later but something that lingered in my sub conscious. I had h... Continue»
Posted by fifebi 4 months ago  |  Categories: First Time, Masturbation, Shemales  |  

Thailand Part 2

I woke up after the wank session hearing somebody in the apartment making coffee, I got up in my underpants and found my friends wife in her Brazilian type bikini behind the counter making coffee. This bikini did not cover up much and her heavy tits were just covered while her arse and cunt was split by a string. I could see her pussy lips spread by the string and I had the starting of a boner.

After coffee we went down to the pool and managed to get a couple of sun beds by the pool, she asked if I would rub lotion on her back and I worked my way from her shoulders, down her back to her bum... Continue»
Posted by daveaverage 4 months ago  |  Categories: Group Sex, Hardcore, Shemales  |  
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