Shemales Porn Stories
Page 61

Serving Waitress

This is the first “didi” story I ever wrote. It’s my deepest (and darkest?) fantasy. It probably needs to be rewritten at some stage because I think it’s been written too much by my male brain and not enough by my female side.

The story begins…..

My wife, Susan, one evening announced to me that we had been invited to a party at a new friend of hers. Victoria had inherited a fortune from her father and she lived in a mansion in the best part of town. It all sounded very exciting. Apparently she had these parties once a month. Susan said that we would go earlier as she had offered Victoria... Continue»
Posted by didi_galtier 4 years ago  |  Categories: Anal, First Time, Shemales  |  
  |  8

my gardner plowed me

My wife and daughter had left to spend a week with my mother-in-law in Brazil. So it was time to breakout my secret wardrobe. Having two women in the house made it easy to keep a sexy supply of clothes. Add a wig and some makeup, I'll soon be lookin pretty hot.

I started by shaving my body and taking a long hot bath in some lovely smelling bath oils. Just the thought of dressing up was making me wet. I dried off and went to get dressed. Being in a wheelchair made it take a long time to get dressed. I wasn't even going out but I wanted to dress up and maybe video chat with some hung studs, ... Continue»
Posted by cdaisy1 4 years ago  |  Categories: Shemales  |  
  |  4

Ladyboy DP for Thai Wife

I opened my eyes and lay still in bed, awake unusually early. I could feel the warm presence of Noi snuggled up in bed bedside me. She was sl**ping face down with her little bottom next to my right hand. I reached out and touched the warm butt cheeks of Noi's tight and shaped ass. I gave them a fond little squeeze and felt my cock stirring with desire.

Noi was your typical lovely pleasure loving Thai woman, very petite with a slender shaped body and girlish hips. She had lovely soft silky brown hair and a wonderful pair of red lips that were delicious to kiss, as feel heavenly wrapped arou... Continue»
Posted by sanpeesua 3 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  
  |  7

The Fuck that would never end

This is a short story k?
I went to Italy to visit my cousin Lance and he showed me around and some of the guys hit on me but when the day was over i layed on the couch and fell asl**p...
about 3 hours later...
I woke up on a stool tied up and saw my cousin nude infront of me with a HUGE COCK! and he said,"Well well....the fuck slave finally woke up..." I tried to speak but i realized that a gag was in my mouth i looked aroun i could only see Lance,the lightbulb,and darkness around me.
All at once 3 white guys about 7 inch each (not counting lance) all slapped their dicks in my face.
after... Continue»
Posted by FuckmyhornyAss 5 years ago  |  Categories: Anal, Gay Male, Shemales  |  
  |  8

Teen pussy of 18 years in bathroom stall masturbat

Certain noises merge from a closed bathroom stall door which you well know are only from a girl pleasing herself, so it was no surprise to myself, a shemale, who uses the girls room very discreetly, to hear such moaning 2 days ago in the bathroom stall of a store in the local mall. And since i jack my cock off in those stalls also and spurt my jizz, it is always a thrill to hear another girl moaning, even so slightly, with pleasure as she fingers her wet pussy. Thus, i literally stood next to the door and wham, it was not locked, guess she wanted to be watched, so i went in and she just smiled... Continue»
Posted by cumsquirter 5 years ago  |  Categories: Shemales  |  
  |  10

Shemale on wheels tour

Being a sexy naughty city girl like myself…I get allot of attention from the boys. I always enjoy getting the attention of the small town boys that are not used to seeing a sexy bitch like me roll though town. They jerk off to girls like me online all the time. But having me right in front of them sometimes makes them overwhelmed and easy targets and my prey… lol.

For me, I love sex. I enjoy the attention of men and I love being used by a man. But the biggest turn on for me is finding some dumb straight boy and wooing him with my big tits and dropping to my knees and having him give me a go... Continue»
Posted by tashajones 4 years ago  |  Categories: Anal, First Time, Shemales  |  
  |  18


Here I was, on a Sunday night, going in the club to have some fun.
After few hours of dancing and drinking, one pretty girl came and asked me to dance with her. Looking at her I saw that she`s not a "grenade" so I was thinking maybe I will have some fun tonight so we started dancing. After a while I started rubbing her ass, then I kissed her...OMG she was such a good kisser.
After she broke the kiss she asked me to come to her place and I was so excited that i took her hand and put it to feel my boner.
She gigled and we start walking to her place.
As soon as we arrived..i couldnt stop ki... Continue»
Posted by mercander 4 years ago  |  Categories: First Time, Sex Humor, Shemales  |  
  |  4

The Perfect Woman, Plus (Part I)

This is the 1st part of a 3 parts story. It is not mine but I hope you like it...

The week my girlfriend Monica broke up with me, I had to fly to New York City for a convention. I must admit, my mind wasn’t on business, and the first chance I got, I went to the hotel bar to drown my sorrows. The bar was fairly empty, which was O.K. with me, since I wasn’t really in the mood for conversation anyway. I was half-way through my first pint of Guinness when the cocktail waitress brought me another glass.
“Hey,” I objected. “I didn’t order this!”
“Relax,” the pretty brunette said. “It’s fro... Continue»
Posted by freegre 1 year ago  |  Categories: Anal, First Time, Shemales  |  
  |  4

First time out, first time fucked.

I was looking good even if I do say so myself. Six inch black platform heels, black hold ups, the obligatory little black dress, long red wig and my fave faux fur jacket. I felt sexy, I felt like a slut and I wanted the world to see me.

I hadn’t been out before but I had been building myself up for this moment for months. I had it all planned. Wait until dark, slip on my sweatshirt, tracksuit bottoms and trainers over my stockings and dress, stick my wig, shoes and jacket in my rucksack. I’d have to risk it in case anyone saw the make up but I figured it would be dark enough for no one ... Continue»
Posted by Shimmerts 4 years ago  |  Categories: Shemales  |  
  |  34

The best s****r ever part 5

Yes this is all true. please read from the first stories.

The next morning I woke up and we had all slept in our parents room and my cock was still in moms pussy while i had dads cock up me as well. Me and my s****r both went ownstairs and had a sandwich and another fuck before mom came downstairs to leave for work. When she came downstairs my s****r came in my mouth and I came in my moms mouth nd we swapped cum as she kissed me goodbye.

It is two years later now and we are all above age now so nobody could look down on us outside the f****y for having sex. I had taken a course in the lo... Continue»
Posted by horndogs 4 years ago  |  Categories: First Time, Lesbian Sex, Shemales  |  
  |  1

Willows transformation 1

Fern and I had been married for three years. Our sex life had become bland, routine, and, frankly, I preferred masturbation to the work it took to cum by intercourse. I was pretty sure that Fern felt that way, too. You see, my cock is, at best, 5 inches. My touch, or my tongue, on her clit seemed to be much better received than my cock inside her.

I've always been a cross dresser. I can remember being in first grade and wearing my older s****r's clothes and pretending I was on a date with a boy. Before we married I told Fern about this. She treated it as something that would go away once ... Continue»
Posted by stig1963 5 years ago  |  Categories: BDSM, Fetish, Shemales  |  
  |  2

Jason's Joy

Mum had asked me if I would look in on her half b*****r Jack. He hadn't been in touch for a couple of weeks and normally will contact his s****r twice a week. On a Saturday afternoon I would normally meet with friends in town. I call them friends, but I am a bit of a loner and I hang around the fringes of a group of lads. To get to Jack's house means crossing through town. Now that i have my scooter it takes no time at all.
I arrive at Jack's house and I find the curtains are drawn. No windows open despite it being a warm afternoon. I knock on the front door but there is no response. The side... Continue»
Posted by dasilva1672 3 years ago  |  Categories: Mature, Shemales  |  
  |  8

A night in Japan

I was traveling in Japan and had a free Saturday night
so I headed down to the area with all the night clubs.
I went into a couple before I found one that I liked.
There were naked girls dancing and other girls
wandering around flirting with you.

One girl caught my fancy, her name was Sindy. She was a
tall blond, I would guess from Eastern Europe or
Russian maybe. Sindy was topless and was rubbing my
crotch as I watched the girls and then asked me to go
into one of the private rooms.

We headed off and as soon as we were in there she had
my pants down to my ankles, pul... Continue»
Posted by vdub-guy 2 months ago  |  Categories: First Time, Gay Male, Shemales  |  
  |  2

New neighbour

A few days ago a new neighbour moved in my building.He lives alone and is an electrician. He is tall and handsome and is about 35 years old. Has dark hair,brown eyes and a body to die for. Since he moved in every time i see him or pass by him i get really horny and cant stop thinking about him.One day i came home and saw him sitting in the leaving room talking with my grandparents.I introduced myself and got horny as hell when he touched my hand. I instantly went to my room and waited for him to leave.When he left my grandparents told me he was here to fix some electrical problems in the kitc... Continue»
Posted by nikoletakurva 5 years ago  |  Categories: Anal, Hardcore, Shemales  |  
  |  9

Stop screaming whore you know you love it.

I made a horrible mistake.

I am usually so careful when meeting up with guys. I had been chatting online with a young guy in his early twenties for about a week and he seemed really nice. Like a lot of guys he was interested in meeting a Tgirl but I was bit hesitant as I prefer older guys. Mostly I meet up with guys at a neutral venue or at my place to have some control over the situation. Since he didn’t have a car I agreed to meet him at his place. Silly move on my behalf. I got dressed in my sexiest black skirt, black blouse , stockings, push up bra and black leather boots and went ou... Continue»
Posted by toniparr 5 years ago  |  Categories: Gay Male, Hardcore, Shemales  |  
  |  6

Turned my Mistress

I woke up, groggy, in a world of bright lights and fuzzy shapes. I couldn't move properly, my arms slopping about like sticks. I turned my head, trying to focus on the world, but it just slumped to the side.

'Good, you're awake,' Came a sultry voice.

I heard loud clicking and out of the corner of my eye I saw a hazy black shadow tower above me. My mind wanted to say, 'who are you?' But all that came out was a few slurred noises.

A hand ran its way along my body until it held my face, tilting it upwards. 'Don't worry sissy. We are nearly there; one injection to go.' With that, My le... Continue»
Posted by waraxe13 3 months ago  |  Categories: Fetish, Shemales  |  
  |  4

Angel and I share Laura

Laura and Angel had been friends since Laura moved to the area a few months earlier. They had met through work and became fast friends. Both Angel and I had been attracted to her since we had met her. She was 25, short only about 5 feet tall, skinny, but with lovely big tits. She had big brown eyes and mouse brown hair and a beautiful smile. Not only that but a lovely girl smart and funny. Angel had asked her to join us in a threesome but she didn’t want to as she was only interested in Angel not me. She asked if she would be interested in just letting me watch, but she still wouldn’t go for i... Continue»
Posted by onebaddaddy 3 years ago  |  Categories: Anal, Group Sex, Shemales  |  
  |  7

Jasmine in Hotel Part 2 - The Mans Perspective

From His perspective now..

So this is picking up from just having had Cum down your throat, leaving you lying on the bed with your makeup all messed up, your ass gaping wide and exposed and your hands tied behind your back......

I go and fix myself a drink... maybe a big glass of whiskey. i'm feeling satisfied and very macho, knowing that i've really given it to that slutty tgirl, in her sissy little latex dress and whore heels. I can't believe how cheap and easy she was, letting her garters and G-string show the way they did, her face all dolled up with bright red glossy lips and all ... Continue»
Posted by JasmineSissyCD 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
  |  3

Home alone, at last

At last, home alone for a while …..

So, I managed to have a whole day home alone. My life is quite complex with people arriving and leaving regularly, then there’s me being away for short stays whilst I’m working so being home alone can be difficult.

But the problem was that I was missing being naughty, so I planned a whole day for FUN !!!

I started advertising that I was available on two French contact sites a couple of weeks ago, lots of interest and messages but as usual, quite a lot of nonsense, fantasists or guys without the real interest in some serious action.

But one of the... Continue»
Posted by antoniaf 3 years ago  |  Categories: Masturbation, Mature, Shemales  |  
  |  2



Kate heard the bell ring from downstairs and dashed to the
mirror. The reflected image betrayed no flaws. The lipstick was
red and thickly applied, giving the pouting lips a playful glow.
The green eyes were right too-- the dark eyebrows thinly plucked,
the long lashes batting with plenty of body and dark promise, the
eyes themselves clear, bright and green as polished emeralds. No
eyeshadow though-- the Teacher thought that eyeshadow on Kate
gave a too-mature look and Kate was only sixteen. Cheeks were
smooth, with a complexion that was clear but for the inevi... Continue»
Posted by alexwd0 5 years ago  |  Categories: First Time, Shemales  |  
  |  1