Shemales Porn Stories
Page 68

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  |  
  |  2

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  |  
  |  1

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  |  
  |  2

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  |  
  |  3

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  |  
  |  4

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  |  
  |  2

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  |  
  |  1

Cold flour


Kneeling on the cold, concrete floor beside the toilet, dressed in lingerie and wearing pink lipstick waiting for the door to open, my mind kept going around in circles to what led me here, wondering if I could have done anything different to prevent it.
I remembered sitting on the toilet, I looked at my bight pink nylon and white lace panties, resisting the urge to play with myself. They looked so lovely against my pale, shaved legs above the stocking tops and garter straps. I blushed slightly and smiled at what a dirty little pervert I was to wear lingerie under my stre... Continue»
Posted by klammer 4 months ago  |  Categories: Anal, BDSM, Shemales  |  
  |  2

Purchasing Panties and Finding Playmates

I've found a very easy (and fun) way to obtain the used panties of strange women. 

All of the thrift store chains around town carry used women's underwear.

I'll put on some synthetic fabric sweat shorts with no underwear and go shopping. A lil caffeine pill is probably bad for my k**neys and heart, but it sure gets me in the perv mood.

The first thing I do when I enter the store is look to see what cashiers are working, and I begin to scope out the youngest and cutest one they have available. Sometimes I don't manage to get a chick, and it's a dude. Still kinda fun, but I prefer to ha... Continue»
Posted by cumquarts 4 months ago  |  Categories: Fetish, Shemales, Taboo  |  
  |  2

The Covert Operative

“I love fucking your faggot asshole,” the tall, slender career military man announced in French.
“I love that big African dick,” screamed the toned effeminate bottom.
“Take it, slut!”
“Yes sir! Fuck me good. Fuck me like a girl.”
“You are a girl. My girl. Ohhhh, baby!”
“Yes, daddy! I’m your sissy girl. Fuck my ass. Fuck it hard.”
“Bitch,” he roared. “This ass is all mine.”
“Oh yes sir!”

Colonel Rodolfo Urikob slammed his generous ten inch dick into his pussyboi’s asshole. The sweat from his forehead streamed onto the smooth caramel-skinned boy. He plowed feverishly nearing ejaculatio... Continue»
Posted by faggyboi 3 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
  |  1

Jr. Prom 5

My Jr. Prom-5


Bob pulled up his pants and we went into the living room to play video
games on the big screen. We rolled around on the floor, sat cross legged,
played video games and talked like we always did.

After about 15 minutes, Bob was putting up a tent in his pants. I continued
to play video games and thought about what a turn on it was to know I was
making him hard. I smiled and could feel my pussy getting wet.

After about 30 minutes, Bob was having trouble getting comfortable. I
giggled, got up and got us some sodas. I wiggled my ass for him... Continue»
Posted by cire9691 3 months ago  |  Categories: First Time, Shemales, Taboo  |  
  |  2

Daddy's Little Sissy Cock Sleeve.

I stirred as I felt my bed suddenly shift with the weight of someone crawling up from the end and between my legs. I’d slept so peacefully, as I do every night when my Daddy Dom locks my wrists and ankles to the corners of my bed in leather lined steel resrraints, face down, with my little sissy pussy filled with his cock. He fucks me to sl**p, and keeps me covered like a security blanket till I’m soundly dozing, then he slides out of me and fastens the translucent pink plastic panties around my waist. He doesn’t bother with diapers… he used to, but he says he likes the way it looks when his c... Continue»
Posted by AniGirl81 3 months ago  |  Categories: Anal, BDSM, Shemales  |  
  |  5

Dream Date. Part 1

Part 1 Dream Date.....

Sitting along in a booth enjoying 18 yr old scotch, when I hear the clicking a high heels against the wooden floor. All the men and some of the women turn and take you in. You are absolutely one of the hottest women I have ever seen. Wearing a short blue demon skirt white top and very super sexy red heels, but it's not what you are wearing, it's your smooth sexy long legs that has my attention. I can see the envy in all the men's eyes. I ask you to sit and you ask if I've been waiting long, in which I reply you are well worth the wait.
This ... Continue»
Posted by pleasetv 3 months ago  |  Categories: Anal, First Time, Shemales  |  
  |  2

Fucking my first tranny - Fun times with Jennifer

This happened about a month ago, it was one of those days where I felt really horny so I had to do something about it and I just didn't want to fuck a woman this time. I've been really curious about trannies for a while now, I once fucked a friend of mine when were fooling around (I should write a story about him too!), but the combination of tits, smooth ass and a cock would always catch my interest and would get me really aroused every single time I thought about having sex with one.

A little backstory to this before we go any further...

Through this bullshit dating site I came across... Continue»
Posted by Sylf 3 months ago  |  Categories: Anal, First Time, Shemales  |  
  |  5

My Dirty imagination ;-) Chapter 1

I arrived on the doorstep of a huge house, feeling a little intimidated and small in comparison. As I knocked on the brass door a few seconds later a woman appeared at the door, mid 40s, tall, brown ei black hair in a pencil skirt and a shirt. With heels on as well she looked rather intimidating but smiled and said “oh you’re his present” I half smiled and nodded not knowing what to say. She invited me in, fixed me a drink of cider saying “its what all the young boys love isn’t it” and led me down into the cellar. She then told me she was going to get me ready, she asked me to strip from my bo... Continue»
Posted by CathyxXx142 3 months ago  |  Categories: Anal, First Time, Shemales  |  

A Super Panty Daddy Fantasy -- PART ONE

*From time to time I get so horny that I start looking for partners on CL. It has been years since I've managed to actually physically connect with someone that I found on there. This story is a fantasy of a scenario that I'd be very interested in playing out. Hope you enjoy.*

Scanning down the page on Craigslist, I was looking for ads for m4m, t4m, m4t, t4t, and especially mw4m / mw4t. I found a mw4t ad that instantly hardened my pantied dick. The sheer fabric stretched as I kept slowly teasing the underside of my cockhead through it.

"Looking for masculine panty daddy.

We are a... Continue»
Posted by cumquarts 3 months ago  |  Categories: Fetish, Group Sex, Shemales  |  
  |  2

The Passage of Lydia Part 2

Let me continue my tale ……..

I sat in front of the mirror and saw my pale face as a blank canvas but the array of lip sticks, foundation, eye shadow etc. filled me with dread, I’d watch my mum getting ready and the way her hands would wave our her face and then presto she was all glammed up.
I have to admit it was a disaster and my attempts made me look as if I had been beaten up. Dismayed I thought I would checkout the hat boxes on top of the wardrobe. Eureka! I giggled like a little girl when I found no hats but 6 wigs, and by the soft feel they were good ones. I was drawn to the shoulde... Continue»
Posted by fifebi 3 months ago  |  Categories: Fetish, First Time, Shemales  |  
  |  1

Pink Short Shorts

For Miniskirt-boy

It's a lazy Wednesday getting close to noon and I'm still lying in bed when Sammy walks in. She's cold. Summer has been pretty underwhelming this year to say the least. The sky is as dirty as the gutter and overflowing, rain hammering the windows.

'Hey,' I smile invitingly and she sees just beneath the covers that I'm still naked too. 'What are you doing?'

'I just came for my knee high socks, my feet are cold,' says Sammy, parading her ass and lean legs in those pink short shorts of hers. On top she's wearing a white pyjama top with pink polkadots, her... Continue»
Posted by dantheman1980 3 months ago  |  Categories: Anal, Shemales  |  
  |  5

Something different ....part 3

I looked in the mirror as the curtains behind me opened, my hands went to cover up the growing bulge in the dress i was wearing as i stared at the reflection of the woman who now stood behind me. Just been sorting through the racks and thought that this might suit you she said as she held out her hand towards me which held a corset. I turned a little making sure that my front was facing away from her conscious still of my bulge. I thanked her and took the corset from her and told her that it looked a little bit on the small size. She laughed and replied that it was a lace up corset so that th... Continue»
Posted by oldognewtrix 3 months ago  |  Categories: Fetish, Mature, Shemales  |  

Good ‘sheboiz’ shouldn’t be allo

This is the problem with sissies not locked in chastity. They love the girly clothes - mincing around in high heels and frilly dresses. They love the way they feel an look. It turns them on beyond belief. But most of all they live the way their useless appendages feel through the sheer nylon of their pantyhose or the soft, smooth satin of their panties. They can’t help themselves. Sissies ate generally lifelong, compulsive masturbators. Inevitably this will happen. Cum all over its pantyhose and But most of all they live the way their useless appendages feel through the sheer nylon of their pa... Continue»
Posted by klaramolka 3 months ago  |  Categories: Fetish, Gay Male, Shemales  |