Shemales Porn Stories
Page 3

The Next Day (followup to Day With Matt)

The Next Day

After my whirlwind day with Matt I was completely exhausted. I got back in my room and immediately headed for the bathroom and started to run the water for a bath. I glanced in the mirror and saw my face was still a mess.

There was dried cum in my hair and on my cheeks. I couldn’t believe my neighbor had seen me like that.

“Oh well,” I thought to myself, “perhaps it would lead to another fun day tomorrow.”

I stripped out of my clothes and peeled off my bra and panties and climbed into the piping hot Jacuzzi tub. I had poured in some of my favorite lavender bubble bat... Continue»
Posted by tiffanytvslut 19 days ago  |  Categories: Anal, Hardcore, Shemales  |  
  |  1

Crossing Paths

She was nervous, as time dragged on in the little out-of-the-way motel room. Jill’s sluttish-painted, shining blue-green eyes were fixated on the door.

Jill and Brent had met in cyberspace a long time ago and had travelled parallel paths. The mutual attraction and communication with each other was almost instantaneous and grew into an earnest relationship. But each knew that that a face-to-face meeting was impossible, as one of their mutual attractions to each other was their comprehension of wedding vows.

Thus, the subject was never broached betwixt them along that long paralle... Continue»
Posted by prairieFreak13 19 days ago  |  Categories: Shemales  |  
  |  5

New Year

"Let me get this straight. You want to book me for New Year's Eve at the stroke of midnight."


"But I have some killer party plans. How bout we meet earlier?"

"I'm sorry. It has to be midnight. I'll double your rate. Triple it if you cum inside me bareback at exactly midnight."

"All because of the silly superstition that whatever you're doing at the stroke of midnight on New Year's Eve is what you'll be doing all year long?"


"You know that's bull shit. Right?"

"Probably, but what have I got to lose?"

"Why me? Why not one of the other girls in town?"

"S... Continue»
Posted by Ber3 19 days ago  |  Categories: Anal, Gay Male, Shemales  |  
  |  1

Sissy's First Cock

Sometimes you've got a secret thats swollen up inside you and you've just got to let it out. From my earliest days I had an affinity for wearing ladies underwear. Living in a small Irish town this is not exactly something that is deemed worthy for public consumption. I tried telling my father once when a program came on television featuring a transvestite character about how that was something I liked to do. It was laughed off as a joke and I decided it was best left that way. In the end my parents didn't need the hardship and besides as I grew to understand it more there are thrills in secrec... Continue»
Posted by emmadeevine 19 days ago  |  Categories: First Time, Gay Male, Shemales  |  
  |  2



In total bliss with the surrounding warm sand feeling its way along the contours of my body as I lay on my back, my bum sinking into it forcing the sand to give way and conforming to my feminine figure. Feeling the sand compress forcing my lady junk to the sides like jelly testing the strength of my bikini. The sand occasionally absorbing the rare moment a droplet of sweat that runs down my inner thigh, down and around my bum just missing my other cheek to race over my tanning smooth skin. Now a part of the De Bakke Beach in South Africa on a really hot sticky day. I almost fe... Continue»
Posted by dirtyjenna 20 days ago  |  Categories: Anal, Interracial Sex, Shemales  |  

Dee Maple - My hot coach training session

It was my last year in high school, the magical summer was over, I still spend some time at casper house and especially enjoying my anal romance with ram who kept delivering amazing orgasms, feeling me up with his greasy cum and humping me day in day out when the f****y was out, he was doing my biding and i liked it, but still i needed someone to dominate me and make me feel like a true whore, an anal slut, a dirty cum filled bitch. As it happened a new coach was hired and we saw him during Monday at the gymnasium, he came in, one hand griping a basketball and another a large stick - hmm…

... Continue»
Posted by deemaple 20 days ago  |  Categories: Anal, Interracial Sex, Shemales  |  
  |  2

Blowjob in toilet mall :)

OK let me start with the begining :D
I was at work bored a little thinking at cock of course :D so I started to chat with guys on a gay site :D so I was talking and talking and ther was one guy 40 years old married that he said that he loves to do public sex or outdoor so I said shit mee too :D (I have on my profile description that I love gloryhole and sucking outside) thats why we were so in to the tal... Continue»
Posted by CUMdrinkerSISSY 20 days ago  |  Categories: Gay Male, Shemales  |  
  |  4

Sissy's First Orgasm

The first time I ever came I was wearing woman's clothes. I guess I was always destined to come to this. Even before puberty struck I found myself rustling through my mother's dresser looking for something soft and shiny to feel against my skin. There was a comfort there and while I still didn't fully understand it an excitement too. When I first discovered women it was still a pre internet age and pornography didn't go any further than the lingerie section of my mother's shopping catalogues. The first hint of cleavage and the female shape enticed me, but I was just as much drawn to the bras, ... Continue»
Posted by emmadeevine 23 days ago  |  Categories: First Time, Masturbation, Shemales  |  
  |  4

Dee Maple - The Principal Daughter - A

“Principle Jerroti will receive you know” looking sternly at me Rebecca the secretary pointed to the mahogany door with a opaque square window in the center, the initials G.M.Jerroti where inscribed on top. Gordon Mathew Jerroti was our dear principal and for some reason he arrange a meeting with me.
I was curious and scared, in 6 months we will graduate from and move on and this meeting was unexpected. I slowly opened the door “close it behind you” said Rebecca - Ok bitch i will i thought, didn’t like her attitude. The room was filled with sun light from the big open windows behind Jerroti ... Continue»
Posted by deemaple 23 days ago  |  Categories: Anal, Fetish, Shemales  |  
  |  2

My wife my fantasy true in a wedding party

First start off by describing my wife. She is 32yrs old a beautiful woman. 5'1" tall 110 lbs nice big ole' breast with a bubble butt, and very sexy calf muscles. I love her legs. She is some what of a conservative girl. Doesn't really show off her body much. But it is hard not to notice, when she has on yoga pants on! She is in every sense " a woman in the streets but a freak in the sheets."

As far as our sexy life I can't complain. She is always open to trying new things. As long as they're not to crazy, open to anal when in the mood, and loves to suck cock. She truly loves every inch of my... Continue»
Posted by hamgaycouple2015 24 days ago  |  Categories: Celebrities, Shemales, Fetish  |  
  |  3

Incidents in a cross dressers life. Part Two (A tr

My first "outing" was with a female fuck buddy. She loved sex. Any time, place, or person. Damn she was a great fuck buddy! She asked about any fantasies I had. I mentioned I always wanted to cross dress in pantyhose, panties, bra, and a great wig. We spent the afternoon shopping and found all of my needs and a great wig that matched my natural hair color. There is a nice pic of me labeled "first pic." in the gallery.

My nipples and cock were rock hard the whole time, especially while she dressed me. While assisting me with the pantyhose (I pretended I never tried on a pair), my boner was ... Continue»
Posted by williegirle 25 days ago  |  Categories: Anal, First Time, Shemales  |  

While you were sl**ping Helen

Oh my sexy little tart, on rising my cock did also anticipating fucking your sweet little cherry baby! Oh thank you for being my little whore and dressing up for your Lady Dera to fuck! Thank you for wearing your summer dress! I dream of lifting it up, pulling down your panties and sucking your little clitty before I fuck your pouty little pussy. I then stand up to kiss your sweet red lips and began rubbing your hard erect brest! I pull your top over your head and look at your sexy armpits while doing so! I rub them.look into your dreamy eyes and tell how sexy your armpits are and how they tur... Continue»
Posted by LadyDera 25 days ago  |  Categories: Anal, First Time, Shemales  |  

Mr. Jerkface

Alex was a class “A” jerk and I was done! I deleted all his emails and texts. I removed his contact information from my phone and took all the Teddy Bears and fake jewelry you bought me, and clothes he had at my place; put them all in a black trash bag and prepared to toss it down the trash chute. The whole time I was storming around, my phone kept ringing and I knew it was him.

Txt – “Baby I’m sorry”
Txt – “You always said you wanted to try a gangbang”

I kn... Continue»
Posted by MatureBrownMan 26 days ago  |  Categories: Anal, Gay Male, Shemales  |  
  |  2

I didn’t know she was a different kind of girl too

The Starship Peacekeeper was steadily cruising at warp one on a routine mission to a mining colony somewhere in the Black Eye Galaxy. Most of the bridge crew had taken downtime. Some sl**ping, some drinking, some pursuing their pet hobbies in the research facility.
I was so lucky to work for the Federation. Here I was judged solely on my ability to do my job and, aside from a few smirking nods from the captain, not on my tendency to put on a female uniform and ask to be called Sindy. Not that it mattered much. My role meant I was usually alone on the bridge, monitoring activity during the lon... Continue»
Posted by SindyBlondeCD 27 days ago  |  Categories: Anal, Shemales  |  

From the GurlTown files Maria

Calvin woke trying to turn on his back, only to find out he couldn’t. Maria quietly said, “where do you think you’re going” then added. “You forgot you knotted me last night”? They both laughed remembering that last night was one for the books.
The thought that today would be the start of taking the boys, they had fucked like a****ls. The boys, Jason, Eric, Charles and Roy had spent the summer and Winter had set in. They had spent summer outside enjoying the wilderness but the first snow dropped a foot trapping them inside.
Under the heat of the summer sun, she had accidently flashed and f... Continue»
Posted by GurlTown 27 days ago  |  Categories: Fetish, Hardcore, Shemales  |  
  |  5

Cockatoo Part 15

I woke to find Alex already up and talking with Nin. My shoulder was
still aching, so I swallowed a couple of painkillers with some orange
juice before remembering to ask Alex about Pao. She was improving fast,
and would be discharged either today or tomorrow. Alex wanted to stay in
Bangkok, but I told her to go back to Samui to be with Areeya. In the
back of my mind I had the idea that it would be safer there. I also said
to Nin that she should also return to recover for a few days, and then
she could come back fully rested. Nin was reluctant, but Alex agreed
with me that it would be ... Continue»
Posted by nikkiesilk 27 days ago  |  Categories: Shemales  |  

Bookstore Surprise!

One of my favorite adult bookstores was just outside of the town I grew up near. There were two of them, one on each end of town. This was the one that was most active [usually] and, I considered it the best. There was a low end motel across the road…no big surprise there and, another about two miles away. It – this bookstore - was the cleaner of the two choices and, if you’re gonna spend part of the night on your knees, a cleaner floor is a good thing…

Bookstore surprise.

This one seemed to have a better range of clientele; teachers and other professional people went there. I’d ... Continue»
Posted by swat412 1 month ago  |  Categories: Anal, Gay Male, Shemales  |  
  |  14

Sissy world chapter one the start of a new world.

It's 2019 things ain't the same anyone, near the end of 2017 there was a huge violent outbreak of a disease that is called the female disease. More and more females started getting the disease there is no cure for it at this moment in time if you have it you die, men seem to be immune to it. Only a rare female bl**d type can servive the disease. The few remaining females are all in a secret underground base and are being tested and used to keep the human race alive, so the world we know today is a mans world what does this mean you ask well I'm going to tell you.

The first month after all ... Continue»
Posted by blacklj 1 month ago  |  Categories: First Time, Gay Male, Shemales  |  
  |  3

Motel Magic Hour - Part 3

I must have drifted off to sl**p multiple times before I finally gave way to u*********sness. It was amazing that I was even able to achieve such a feat given that I could only breathe through my nose and my wrists and ankles were secured in steel cuffs and binding me to the chair they placed me in.

Lisa, the sissy who had been relentlessly ****d nonstop in front of me for an hour, seemed to have also lost consciousness, though her hips constantly, but subtly, rocked up and down on the wedge they had elevated her fuck hole with.

Cars came and went from the seedy motel. I could hear big ... Continue»
Posted by AniGirl81 1 month ago  |  Categories: BDSM, Fetish, Shemales  |  
  |  1

First time - "Stud's"

First time - stud’s.

A continuation story from “First time stallion” and “first time stallion - Black stallion”

It’s the dead of night, I’d been lifted out of a camper van by my black stallion that not more than 20 minutes ago had been having his way with me in my hotel room. My arms reaching up around his neck while he carries me, my body in an elongated V shape held at his front. His right arm under both my legs and his other arm supporting my upper back. His right hand squeezing into my black self-holdup stockings just above and behind my knees while his thumb I can feel seductively a... Continue»
Posted by dirtyjenna 1 month ago  |  Categories: Anal, First Time, Shemales  |