Shemales Porn Stories
Page 121

Norman and Anastasia

For the first time in my life, my uncle Norman was not pleased to see me. His s****r, my mother, had not heard from him in a little while and was worried so I had been volunteered to drop in on him and make sure that all was well. So here I am stood on his doorstep and he is peering round the door at me, holding the door open as far as he can to make sure that I can't see in but so that he can see me. He wears an annoyed look on his face. I am disturbing him in some way. It is then that all becomes clear. A voice speaks behind him.
"Who is that Norm?"
He turns his head so that he is speakin... Continue»
Posted by dasilva1672 10 months ago  |  Categories: First Time, Gay Male, Shemales  |  
4923
  |  
93%
  |  8

Tranny and Me Meet The MILF

This past Friday morning my phone rang. It was Chandra my tranny friend who I met and fucked some weeks ago. She told me that she had nothing to do this weekend and that her roommate was out of town and she was alone. I told her that if she wanted to get out of the city that she could spend the weekend at my place. She said that was a great idea and that she would be over in a few hours. When Chandra got to my place she was horney as hell. She dropped her overnight bag, dropped to her knees and opened my pants. She pulled out my cock and began to suck it really good. She was licking my balls, ... Continue»
Posted by adw276 5 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  
1799
  |  
93%
  |  4

Prison Ain't So Bad

"I can't fucking believe it, not too long ago, to this day, I was living a good life, I was drinking champagne with my girlfriend Alexis, not the brightest of girls but damn she had a nice body, that night we drank until we couldn't and fucked until the sun came up, now look at me, travelling on this bus heading to prison, all because I was stupid enough to commit fraud".

The bus pulled up at the prison and instantly the convicts gathered by the fence, I could hear them all screaming and yelling, even managed to hear a few things being said, "Fresh fish!", and "Welcome to hell!" were the on... Continue»
Posted by wherethewhitewomenat 1 year ago  |  Categories: Anal, Interracial Sex, Shemales  |  
3070
  |  
93%
  |  3

Mile High (caught in panties and pegged at thirty

Mile High (caught in panties and pegged at thirty thousand feet)

By Mikaho

Edited by g1dnshwrgr1 (many thanks!)

NOTE: This is my story and is originally posted under my profile on literotica.com. You can see it there under my same user name. Enjoy!

I boarded the plan and was taking my seat when I noticed the most mature of the three stewardesses. She was beautiful with a classic flair; her pencil skirt perfectly presented an hourglass waist, defined hips, and a round butt.

The image of her shapely form flitted around the edge of my thoughts as I started answering email on my... Continue»
Posted by Mikaho 3 years ago  |  Categories: Anal, BDSM, Shemales  |  
2575
  |  
93%
  |  4

My Boss Tricked Me

I work for a cell phone company. Part of my job is to travel to cell phone towers and fix any problems they might have. I enjoy it but am on call most weekends. Now I consider myself a man in public but at home I love dressing up as a slutty tramp. I love the feel of lingerie on my body. I had a few experiences with a man but it was mostly mutual masturbation. My crossdressing is a secret to everyone except the few I have met online.

Most Friday nights me and the coworkers go out drinking. Just a bunch of guys out having a good time. One particular Friday I got really d***k and my superviso... Continue»
Posted by sissysadie 2 years ago  |  Categories: Fetish, First Time, Shemales  |  
9862
  |  
93%
  |  10

My mother, my lover

Wow
I have no idea where to begin with this story. My mom came by yesterday while the k**s were off fishing on the lake.
I knew when she got here that there was one thing on her mind, and she was not shy about letting me know either. I was painting our daughters room when she came in calling for me, I knew just by seeing how she was dressed that my implant was in for a workout.

She walked into my bedroom and starts calling out " Baby mommy wants to play".
I walked into the room and saw that she was only wearing a smile on her face, both nipple rings, her tongue piercing, and on her toes... Continue»
Posted by Taboo69 3 years ago  |  Categories: Group Sex, Shemales, Taboo  |  
6414
  |  
93%
  |  9

Sally the seducer...


I had been chatting online with her for about a month and she finally
asks me to stop by. My butterflies are churning in my stomach, as I have
no real idea what to expect I have only seen tease pictures. You know
the kind, no face barely a body part in the picture.

I pulled up to the address she gave me and knocked on the door. I did
not think she was going to answer and this man answered the door.
"Hi, come on in. "I will be ready in a minute." I was
shocked the woman on the phone sounded female so sultry making me long
to touch her. He disappeared into the bedroom chatting with m... Continue»
Posted by NaughtyNshy 5 years ago  |  Categories: Gay Male, Shemales  |  
605
  |  
93%
  |  3

Domestic Bliss, caught dressing and my life was ch

As I mentioned in another story, I started dressing when I was around 11, at first in my older s****r’s clothes, she was just getting into her teens and had her first bras and stockings and I had my first thrill wearing them. There were just the three of us at home, Mother, s****r and I, father had long disappeared. Mother worked in the fashion industry so back in the 1950s/60s/70s when there were still the classical fashions being worn daily, she was always immaculate.

As I got older, I started to wear her clothes and then one day, my s****r, who was supposed to be out, walked in and cau... Continue»
Posted by antoniaf 4 years ago  |  Categories: Fetish, First Time, Shemales  |  
828
  |  
93%
  |  4

bookstore sissy slut

My name is dollie I love to be a girl and being very petite and pretty long black haired its easy for me too feminize. And until now I wouldn't go out, dressed up, sometimes a quick walk around or a short drive but nothing real. And one time in college I walked around the campus. Anyway I ignored all the signs being overly sensitive for a boy It should of clicked when I was diagnosed with disphoria. I knew I liked being girly but I really thought all teen age boys were like me. Always being a pretty-boy girls always came my way but they all end the same I get hurt because just like a girl ... Continue»
Posted by dcdollie 3 years ago  |  Categories: Fetish, Shemales  |  
1851
  |  
93%
  |  5

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 3 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  
1445
  |  
93%
  |  1

Straight, to Bi, to Gay, to Trans, to Straight (Pa

I don't want you to think we simply lived happily ever after. Nothing is that simple.

We've had our ups and our downs, and our ins and outs. We've had three major hurdles, so far. The first was me freaking out over the idea of having a boyfriend. As natural as it seemed to be with him, and as mind-blowing as the sex was, it was still a huge shift in thinking for me. The second hurdle was coming out.

The third was his affair. But more on that in a minute. As I want to talk first about coming out. Friends and f****y may say they support gay rights and all, and they may be fans of... Continue»
Posted by TransContinental 1 year ago  |  Categories: Gay Male, Shemales  |  
1724
  |  
93%
  |  11

working at a house

I'm fitting a kitchen at a couples house right now. They are both in their thirties. as I arrived in the morning they were waiting for me, they needed to go out and would be most of the day, to which I agreed to be fine on my own.
After about an hour or so I decided to look around in her bedroom. she had lots of sexy dresses, suspenders and stockings. I also found some lovely slightly soiled knickers in her washbasket. After sniffing and licking the gusset, I was getting very hot. I decided to dress up in her sexy gear. I put on her stockings, suspenders and bra along with the knickers I'd b... Continue»
Posted by tarajenkins53 5 years ago  |  Categories: Shemales, Voyeur  |  
1421
  |  
93%
  |  1

Oh,,,,,,,, so helpless

The ankle straps of her five inch heels connected by a short chain and secured in place with tiny padlocks. A virtually unnoticeable black cable secured around her waist held the shiny steel handcuffs that pulled her silken gloved hands behind her, leaving white glossy fingers resting on the very large white satin bow that in turn hung across and down the short black silky smooth skirts and numerous frilly petticoat layers of her French maid uniform. Zipped to the neck and edged in brilliant white lace frills, the locked bodice of her dress was clinging tightly over the uplifted bosom and cor... Continue»
Posted by maidtracie 4 years ago  |  Categories: Shemales  |  
697
  |  
93%
  |  2

First time with a shemale

I must have been 16 back in the day, but I always looked older so it didn't really affect anyone's judgement in the sex world that I had loved since I can remember jerking off for the first time.
I was walking the streets of Amsterdam that day, the Red light Disctrict looked like paradise on earth, all those hot hot girls smiling and telling you to come in...I don't even know how much they wanted, I didn't care, just walking in those tiny streets and seeing those creatures was more than enough.

There pretty much everything there, from the porn starlet straight from Poland to the big Colomb... Continue»
Posted by joelo 4 years ago  |  Categories: Shemales  |  
778
  |  
93%
  |  4

Sex in the Bar

Being a old Ex sailor it is no surprize to me that I am not shy.
I live in Thailand and worked there a couple of time over the years.
Down south near the Malay border there is a great little town where a lot of expats work and live.
I am a sociable guy and love a few beers with the boys/girls/ anybody who wants a drink.
We have a bar in one of the darkside of town where anything goes.
After dark or even during the day you can do anything in the bar.
Lady boys sucking you, young girls sucking you in teh bar besides your mates when their drinking. No shame no problems.

One day I was the... Continue»
Posted by xmas69 4 years ago  |  Categories: Shemales  |  
780
  |  
93%
  |  3

Duty Bound Part 1

Ever since c***dhood it had been that way; delicate in the extreme and a want of soft bright things. School had proved to be difficult; not being like the others. A fondness for the stricter teachers irked the boys; patently apparent differences alienated the girls. The developmental teenage years were no easier, though liberally minded parents allowed chosen apparel to be worn at weekends, making the desired route in life that little easier. The tortuous journey through to adulthood now accomplished, and independence achieved, indulgence in a preferred lifestyle beckoned.

Hannah glanced a... Continue»
Posted by midsummerman 4 years ago  |  Categories: Fetish, First Time, Shemales  |  
577
  |  
93%
  |  2

TV/CD adventures - going for ice, remember ID

It's amazing what high heels, wig, makeup, nylons, mini, etc can do for ya when going out in public.

Couple months ago I got me a room at Imperial Palace on the strip and I think the front desk caught on I was using the room for casual sex. I put up an ad on craigslist and gave out the room number. But setting up times and availability was difficult because I didn't have a computer in the room. So the front desk constantly was connecting me to "different" guys. After being drilled deep by 2 guys I decided to go for ice in my fishnet no panties slut outfit. My ass was gaped and sloppy... Continue»
Posted by vegasjful 4 years ago  |  Categories: Shemales  |  
192
  |  
93%
  |  2

A date with a straight college student

I had been chatting with this boy for a while when he finally told me his parents were out of town and he had his father's car. So we set up a date in the evening. I told him to pick me up by his car from somewhere. I was pretty excited, this jock was a very good looking guy with a slender athletic body type, brown hair/blue eyes. I always had a thing for blue-eyed boys. I was thinking about those whilst putting on make-up in front of the mirror and combing my hair.
I was a lil bit nervous when he picked me. He looked even much more handsome than his photos. Because he was lacking a web cam, ... Continue»
Posted by Slave4str8twinks 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  
1817
  |  
93%
  |  5

Jenny, Melissa and Me

I’m watching you on the screen, Jenny, as you pull down your pretty nylon panties with the floral prints and spread your legs. Your brunette hair hangs down around your lovely eighteen year old face, smiling as your labia open wide and you begin to rub your clitoris, all the while smiling, and gazing at me with yearning through your computer camera.
In front of my camera, so you can see me, I put on a pair of sexy pink panties over yellow nylon stockings and a pink garter belt. I put my hand under a sheer negligee and stroke my shaved cock and silky smooth shaved balls for you to see. I... Continue»
Posted by pantyboykristin 3 years ago  |  Categories: Fetish, Group Sex, Shemales  |  
591
  |  
93%
  |  1

Nice Sunday to worst sunday

Hello guys
Hope everyone doing great and enjoy my true story
Sorry again guys not very good English so grammar its not their

We all enjoy our Sunday especially now it’s NFL Playoff guys into games so am I
I just buy new big screen TV and love watching games at my on place.

As I woke up on Sunday late morning around 11:30 am still im in my sweet bouquet layered baby doll (nitie) making coffee and doing dishes get my coffee sit on couch watching TV my cell phone ring one of good all Spanish she male friend (Rosie) who was about to go out back to Mexico her grand ma was sick and she a... Continue»
Posted by shawn777 3 years ago  |  Categories: Hardcore, Interracial Sex, Shemales  |  
526
  |  
93%
  |  1