Shemales Porn Stories
Page 59

supermarket tranny

It was a typical Saturday morning. I was at the grocery
store doing my weekly food shopping. As I was perusing
through the vegetable section my eyes caught sight of a
a very attractive woman. She had long dark brown hair,
pretty face and a nice body.

I worked my way over to her and checked her left hand
for a wedding ring. She had none. I made some remarks
about the slim pickings the supermarket had. She and I
quickly engaged in conversation about cooking etc.

We walked around the store side by side picking our own
groceries an just having a good time. It was time to
c... Continue»
Posted by rickk1 1 year ago  |  Categories: Anal, First Time, Shemales  |  
  |  7

What is it about a womens bulge

A very attractive women once bumped into me in a very crowed club in Mexico City, I turned to say excuse me. I was speechless at her beauty. She was wearing a short skirt, garters below the skirt and knee high boots. She just stared at me and with out saying a word she bumped me again. I felt something different something firm and it moved it was very intriguing. I kept looking at her and without saying a word I couldn't move, I wanted to say something and I couldn't. She slowly put her arm around my waist and she slowly rub her crotch on my leg. I was frozen standing there looking at this gor... Continue»
Posted by ilgreek 1 year ago  |  Categories: First Time, Shemales, Taboo  |  
  |  2

that's how I want my gf to cuckold me D:

That's a question I got ask:
Would you rather cheat or be cheated on? And what would be your fave scenario?

That was my reply:
What kind of a sub-sissy would I be, if I would want to cheat on my mistress? ô.o

Fav scenario huh?
Hope at least one person will read the whole story… It took me so long :o

I would like her to tell me about some guy that’s in her class. Let’s call him Dave.
She always complains about what an asshole he is, and how he tries to hit on her everyday. But one day she just stops talking about him.
After two weeks or so I ask her about him, and if... Continue»
Posted by Vivien_Lynn 1 year ago  |  Categories: Fetish, Gay Male, Shemales  |  
  |  7

Julie bent over her desk for Sarah

Sarah: You never let me bend you over a desk anymore

Julie: I’m bottomless.

Sarah: *Slides her hands around your hips and squeezes your butt*

Julie: *Giggles and squirms, rubbing you with her legs as your hands grip her bare ass*

Sarah: *Massages your backside slowly, her cheek rubbing against your thigh as she lightly kisses at the other*

Julie: *Brushes her fingers through your hair with one hand and lifts her shirt up with her other, letting you see up under it*

Sarah: Mm *Lifting herself up a little as she purrs, still grasping tight at your bare bottom, tilting up her he... Continue»
Posted by noin007 1 year ago  |  Categories: Hardcore, Lesbian Sex, Shemales  |  
  |  1

Nate and his tranny neighbour: Part 3

Nate and his transsexual neighbour part three, as always hope you freaks enjoy and let me know what you think ; )

Nate woke up thinking about his last two encounters with his hot big-dicked neighbour. Having never had much experience with woman to having the hottest sex he could hope for was a dream come true. However as he slowly stroked his hard morning wood he realised he had yet to fuck Jez, her gorgeous tight ass in lycra was a vision to behold. Wanting nothing more to feel her pretty asshole clench onto his teen cock as she begged for more. Quickly he decided to try and seduce her to... Continue»
Posted by BiTwinkxx 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  
  |  7

Prostate Milking, Endless Orgasms!

if she wanted breasts."

"Oh no. That's the amazing part. The more I dressed him the more feminine
he became. By now I'd moved him her and her clothes into the other
bedroom. She wasn't happy with that but we came to an agreement; I'd milk
her once a week and she would sl**p in the other room with all her
female clothes. I'd even started teaching her to flirt with a guy although
I didn't tell her what I was teaching her or why. She really was becoming a
real woman. She'd grown her hair and I taught her makeup, had her ears
pierced, got her some jewellery, even got her some bra inser... Continue»
Posted by moekoes8 1 year ago  |  Categories: Fetish, Masturbation, Shemales  |  
  |  1

''What's a man to do''...

After a long week in work I didn't really feel like going to the party we'd been invited to.
My wife said ''We have to go and you never know who might be there''.
I agreed reluctantly and showered and changed and we headed off to the party.

Now at this stage I must tell you these are no ordinary parties we attend. We're part of a group of people that like to play. Yes it involves swapping and doing kinky things with other naked people.

We arrived a bit late and so some of the guests had already shed their some of their clothing.
A few topless women sipping wine with men with bulges ... Continue»
Posted by guru6969 1 year ago  |  Categories: Anal, Fetish, Shemales  |  

Helping a gurl out

Just to explain a few things, we live on an island in the irish sea between Britain and Ireland. T-gurls are rarely heard from, nevermind seen for fear of negative comments.

Vikki was a t-gurl that my wife (K)and i met via a swinging site and had played with on a number of occasions. She would visit the island with work and when done for the day would indulge in meeting anyone who wanted to fuck her.

Vikki arrived on the island on the Wed and we met her on the Saturday. As this was our 3rd meet with her we had all got quite familiar with each other and enjoyed a very sexy evening togethe... Continue»
Posted by ManxTightslovers 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
  |  5

My Parents Had Gone Away on Vacation

My parents had gone away on vacation for a week. I was thrilled!

On my own for a whole week, free to do whatever I liked. And truth be told, what I liked was being nude, as well as dressing in women’s clothes. The first day they were away, I began enjoying my newfound freedom.

I am very slight of build, feminine really. My body is hairless save for in my crotch.

After dinner, I decided I wanted to enjoy myself nude. I turned off all the bright lights in the house, and left on a few lights that were dim. All the blinds in the house were open. I stripped off all my clothes and walke... Continue»
Posted by ssup28 1 year ago  |  Categories: Shemales, Voyeur  |  
  |  6

Pai-chan’s long walk home

School-gurl Pai-chan took the short-cut home from school, through the Sakura sweet smelling woods one Friday after class. The trail went past an old hut and as she approached it, a masked man jumped out from behind her, grabbed her by the arms and slipping a ball-gag into her mouth, d**g the sexy gurl into the hut.

There was a dirty, stained mat in the hut and her a*****or threw Pai-chan onto it. He lit a cigarette, his eyes glinting through the mask as he watched her struggle uselessly against the bonds.

“No... Continue»
Posted by tuckpussypeachpie 1 year ago  |  Categories: Fetish, First Time, Shemales  |  
  |  6

Deflowered at 17...Part 1 (ENGLISH VERSION)

Many friends, some of them curious and excited by my (recently discovered) Polaroid pictures made at the seaside (with stockings) when I was 17 years old, asked me to tell the story associated to them. Someone also pointed out, "but if in one of your stories you talk about your first man -see story “my first man”- after having been “initiated” by a trans, then who was actually your first man? "
First of all, let me say that I can assure you that my stories are not fancy, they are absolutely true. I can change some details, names, situations, ... but I do not not invent anything. Anyone who... Continue»
Posted by AngelicaTrav 1 year ago  |  Categories: Fetish, First Time, Shemales  |  
  |  6

Jake and sexy Tgirl Amanda were next on our "

So after we went out with Pete and Becky all day
Jet Ski's, Diving, and sneaking off for some impromptu blowjobs or a quicky, Alex and I decided that we'd ask Pete and Becky if they'd mind if we brought Jake and Amanda into our group. We described them to them, and they were hooked.

That evening at dinner Alex took it upon herself to make the first move. She sent over some drinks, and they came over to our table and that's where this story begins.

Amanda asked if we were swingers, when I spoke up and told her that even better than that, we're all bi swingers. Her jaw dropped and he... Continue»
Posted by SpicySide69 1 year ago  |  Categories: Anal, Group Sex, Shemales  |  
  |  6

Male to female transgender. Had no idea!

This is a true story. This was a time in my life where I was sort of a bitter person. This story is geared more about the things that led up to my encounter. This was a result of a series of events led up to this point in my life. Let's begin with the basics. I was in the military. I enlisted because I had one full time job and two part time jobs and still had trouble making ends meet. I was seriously overworked and my wife refused to get a job. So logically, I weighed out my options and decided to enlist into the military. It would be one full time job with a slew of benefits. Once I graduate... Continue»
Posted by fortworthfitness 1 year ago  |  Categories: Anal, Shemales, Taboo  |  
  |  25

Vicky's Pink Diary 03

So here I am waiting for my Uncle to come home for his tea, wearing Donna's knickers! Vicky's wardrobe is quite sparse, due to having just one locked suitcase hidden under my bed. I'm lucky that my stepmother is roughly the same size as me, and a total slut! Probably the only thing I like about Jenny is her clothes, she dresses like a girl half her age, and I know for a fact she shags around. I know my friend Sean has had a few narrow escapes from my stepmother. Then one day when I ask him about the way they smile at each other, he owned up. So I now know that they have fucked, I finally got i... Continue»
Posted by sparkyking 1 year ago  |  Categories: Gay Male, Shemales, Taboo  |  
  |  2

Vicky's Pink Diary 04

My head is spinning now, and as my uncle slowly pulls my panties down, I close my eyes dreading my fate!

I watch as he pulls my case out from under the bed. He takes a key out of his trouser pocket and unlocks the padlock.

"My god, how long have you had a key?!"

"Vicky, surely you remember losing a key a little while ago. It fell out of your jeans when your stepmother pulled them out of the washing machine. She didn't notice, but I did. Now I don't want to bring the other you up, but I did wonder why you would have a key in your jeans."

I knew I'd lost one of the keys, but I ne... Continue»
Posted by sparkyking 1 year ago  |  Categories: Gay Male, Shemales, Taboo  |  

Old man fantasy

I have always been aroused by horny old men,I always wanted to be exploited by a group of old horny men until one day when i got this job that required me to take care of a 66 y.o gentleman.
He seemed so nice and since it has been my passion to serve other men i accepted the job without thinking twice.Things went well and we got along just fine..he was really funny and we became close friends very fast.
One day he called me and told me that he must speak with me face to face so that he can share a problem that he had for years with me,I rushed over to his place worried that something may hav... Continue»
Posted by cutecdkiss 1 year ago  |  Categories: First Time, Mature, Shemales  |  
  |  7

Gary's Dressup Sissy

When I was a teenager I lived next door to a guy named Gary. We were friends for years but drifted apart as he was 3 or 4 years older than me, so when he discovered girls I didn’t see him for a while. However, one summer he and his then girlfriend had a fight, so being at a loose end he would invite me over to watch movies and play video games.

One day we were watching a movie, when Gary suggested watching some of his dad’s pornos. I eagerly said yes. So for a few days we would watch porno from about 10 am till 4 pm when his mom came home. His dad seemed to have hundreds of movies. One mov... Continue»
Posted by palmorr 1 year ago  |  Categories: Anal, First Time, Shemales  |  
  |  16

Caught and made into a sissy slut

It was for real this time. No fantasy. Reality. I was dressed up in red: fishnet stockings, g-string, and a babydoll. I was wearing a metal chastity cage that was pulling my clit down, and it was a clit, it only half filled the cage. I had a new cock too - a black face dildo which was double-ended. In my new role, I had to jerk it as I was fucked in my pussy and I was being fucked. She had fucked me so hard that I was completely submissive to her, sucking on my gag with wild abandon, a true sissy slut.

It had started earlier that day when I had been caught jerking off to a mixture of cuck... Continue»
Posted by andygone 1 year ago  |  Categories: Anal, Fetish, Shemales  |  
  |  2

The Lady Inside by loyalsock

I looked at the sinuous curves of her body. The long legs, the curling hair. She was built like my fantasy, every inch of her in pale ivory and inky black. Her pumps hugged the delicate curve of her feet—the arch and the heel. Her dress matched in deep crimson and swung light and silky around her narrow hips and broad back. I stared, unsure if what I was seeing was real or just Hollywood smoke and mirrors. When she turned to me and smiled—lovely white teeth glistening behind her red, red lips—I almost fell backward. I was beginning to think she was a mirage brought on by the heat of the Mexica... Continue»
Posted by loyalsock 1 year ago  |  Categories: Anal, First Time, Shemales  |  

Nothing Else Matters 1 by loyalsock

About a week had passed since the incident with Casey coming by my work place, trying to blackmail me, by telling my friends I was dating a transsexual. I had talked with Christina about the whole situation, and she had been able to calm me down and help me relax. I had been so pissed off at first, that I couldn't even think clearly at the time. But with Christina's help, I was now seeing things a little more clearly than before, and I had even come to a decision of how I thought I could solve the problem without being f***ed to sl**p with Casey as she was demanding.

I would let everyone I... Continue»
Posted by loyalsock 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  
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