Shemales Porn Stories
Page 14

A dream comes true

This is a story that I made. The high school part is the real part in my life that happen, the rest of the story is part of my fantasy.

I was down on my luck, my girl left me after I left high school. We both almost liked the same things, we both liked the same video games, anime hated the Twilight series(ugh even typing it make me feel sick even if it is over) I tried moving on but it was hard but couldn't get her out of my head. When I was not thinking about her my head brings me back to her sometimes for the good time but usually saying "what did I do wrong?" even in my dreams she appear... Continue»
Posted by southwestwarrior 5 months ago  |  Categories: First Time, Shemales  |  
  |  18

The Wedding

The Wedding
Nikkie Silk
Part One
Trust me when I tell you I don't normally check the wedding announcements. I hate weddings. Ever since I was a page boy at my aunt’s wedding, when my mother made me wear a pale blue tuxedo. I was six, for God’s sake. She said I looked so cute.
Aunts and Uncles oohed and aahed at me as I walked down the aisle with the rings on a little satin pillow, but I hated it. You see, what I really wanted to be was one of the bridesmaids in their gorgeous frothy, frilly pink dresses. Even at that tender age I knew that I would rather be a girl than a boy.
There I’ve ... Continue»
Posted by nikkiesilk 5 months ago  |  Categories: Anal, Interracial Sex, Shemales  |  
  |  11

My naughty crossdressing phone call cum

So there I was, in my favourite black hold ups, 50 denier opaque lace tops, my 4 inch heel black ankle boots, and my silky feeking black satin bra and panties set. Freshly shaved, feeling very fem, home alone and horny as hell.

Id been enjoying some of my favourite x hamster videos, and my clitty was aching for attention, so I slipped my panties down my nylon clad legs and started to give it a gentle rub. The feel of my stockings against my skin was heightening my desire and it wasn't long before a red painted nail was slowly circling the entrance to my tight pussy. I slipped it inside and... Continue»
Posted by CharlotteSometimes 5 months ago  |  Categories: Masturbation, Shemales  |  
  |  7

Part 2 - My 1st experience with a "special la

So after a having a great night with Viviana...which included passionate kissing & amazing Blow Job. I couldn't wait to see her again...yet with my schedule, it took a few more weeks before she was able to come over. The following is the story of what occurred that very night.

Viviana arrived at my place around 11 pm. She was a cutie...she had on some tight jeans, a cute blouse and some boots. Just as with our previous visit. We sat down on my bed, catching up what we been up to since our last hook up. Of course, someway somehow this lead to a kiss...kissing...make out...freaky tongue actio... Continue»
Posted by socal805 5 months ago  |  Categories: Anal, First Time, Shemales  |  

First taste of cum for a Crossdresser!

I had never really been with another man before and I had always thought about it as I dressed up as a slutty girl and played with my little toys to orgasm. I'm a little tall at 5, 9 and with heels a monster! I have an average body, nothing feminine, but not out of shape and a nice big bubble ass.

Until that night. I had been sent to Dallas for a business trip and was super excited to dress up in my hotel room and play around! I played around a couple days in my room and just got dressed did my make up and wore my wig playing with my little dildo before passing out exhausted from all the... Continue»
Posted by sxyhispanic26 5 months ago  |  Categories: First Time, Gay Male, Shemales  |  
  |  11

My First Crossdresser

Only a few years back in my young 20's i discovered Craigslist. I had no idea something like that existed and was immediately drawn to it. After building up the courage to meet up with a few guys a couple times i found an add in the T4M section. I got instantly hard when i seen this girls pictures. A slim sexy girl with an ass to die for and a desire for Cock. After some back and forth emailing for a few days we agreed to meet in her place.

I went around to her place late that night when the coast was clear of her housemates about 1a.m or so. My heart was pounding and i was really excited, ... Continue»
Posted by James1989Hard 5 months ago  |  Categories: Anal, Shemales, Taboo  |  
  |  5

and the next time...

So...I had just had an orgasm like I had never experienced on my own before and Tom was now sitting on the bench in front of me, his hard cock pointing up and oozing pre-cum steadily. I also had at least 2 people watching every move I made through the gloryhole... My heart was pounding as I leaned in to work on this cock in front of lips parted as I grabbed the base of his cock and my tongue instinctively flicked the twitching cockhead in front of me taking the precum off easily in one quick swipe. It was sweet and sticky and I ter that I just lost myself in making Tom enjoy this. In t... Continue»
Posted by jnc4456 5 months ago  |  Categories: Anal, First Time, Shemales  |  

cd shazza chapter 3

Hi everyone I hope you all read chapter 1 and 2 because this will make a lot more sense if you did, I wish I was a little better at getting things down in words, these stories a part of my life I would not change but I am loving telling everyone about it the men and the women that I have had sexual contact with I hope you enjoy.
Fred was away for the week and I had a key to open up and feed the cat but more to the point I had a chance to be in Ruby’s bedroom as much as I wanted, I had to go to work but the evenings were mine all I could think about all day was slipping some sexy undies on tha... Continue»
Posted by cdshazza 5 months ago  |  Categories: First Time, Masturbation, Shemales  |  
  |  1

How I turned office newbie into sissy (Part 2) Tru

As soon as I got home after dropping T off I got set to work, booked a semi-local hotel, set my alarm and got an early night. Woke up at 7am with the hardest morning glory I've had in a long time. Was tempted to have a wank but thought I'd save my cum for my sissy. Sent T a picture of my cock and he replied "Can't wait Sir, I'm so excited but nervous". I didn't reply. So I went out early to buy some supplies, went to the local adultstore to buy an enema kit, lube, lace thong and small butt plug. Sent him another pic of the contents of my bag to another similar reply from him..

Anyway, check... Continue»
Posted by BritishPsycho 5 months ago  |  Categories: First Time, Gay Male, Shemales  |  
  |  17

Jessica meets Master M and Mistress V (Part 2)

Before reading you should read part one here: (if you haven't already)

Now we can resume:

As Jessica ate Mistress V's wet, cum-filled pussy Master M was looking on enjoying the show and watching his wife moan in pleasure. Once Jessica had cleaned up all of M's cum, she continued to eat out V's dripping cunt, until she once again felt Mistress V's hand tap her on the shoulder: "Sweetie, I want you to stop, but only because I need to feel you inside me, lets put on a good view for Master ok?"

With this, V encouraged J... Continue»
Posted by Want2BeTrans 5 months ago  |  Categories: Group Sex, Shemales  |  
  |  2

Life Changing Getaway

I was an ever eager worker at my company & climbed relatively quickly to a great position, but of course had far higher goals. I went to school, got degrees & certifications, even worked as a handyman to gain more experience to make me over qualified for almost all positions at hand yet every slot that opened up I got passed by so I went on holiday. A day here & there, maybe a week max at a time, but never planned a full month far away. For some odd reason I felt the desire to go to Texas, perhaps for some Texas Steak, or Texas air perhaps was always meant to end up there. After clearing the t... Continue»
Posted by multiplierx 5 months ago  |  Categories: Anal, Fetish, Shemales  |  

sissy and her Daddy - Chapter 2

jamie and Rich meet again

Huh? Don’t recognize that number – fuckit… let it go to voicemail. Probably someone begging for money. Monday mornings suck enough already, I sure as hell don’t want to be putting up with beggars. I gotta get to work on this proposal or my ass is grass!
Some time passes and the number rings again so I decide to answer it.
“yeah? who’s this?’
“Now jamie, is that anyway to greet your owner? I’m surprised you don’t have better manners. Nobody likes a girl with an attitude”
Oh Fuck….. damnit, I forgot all about…... Rich is sticking to his promise??
“ummm, hi Ric... Continue»
Posted by jamie_anne 5 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
  |  2

CD Road Trip: Nikki's Adventure

“OH” is all that escapes my lips as a cock slides in my ass but the only thing that crosses my mind is how ironic it is that I’m losing my virginity in a cornfield. I’m from fucking Indiana and of course my first sexual experience is in a cornfield. I mean come on, but you know I really don’t care because I’m finally getting what I have dreamed about for years. My jean shorts are on my thighs, my panties are pulled to the side, his hands are under bra grasping my tits, and my cock is dripping cum all over the blanket. This is probably where I should state that I’m a crossdresser. Hi, my n... Continue»
Posted by cdnicole66 5 months ago  |  Categories: Shemales  |  
  |  11

Sissy ghetto bitch!

4 ghetto guys was surfing on porn sites, looking at random sissy babe pictures when they accidently found a picture of someone they know. Like every album they clicked that specific one with a tranny dressed so girly with mouth open and showing legs. The guys had such a stone hard erection after watching all the pictures, they even said "I Would bang that sissy pussy 4 sure!" and everybody agreed. It was that guy from elementary school named C****. They started to chat with him, pretending to be the perfect guy to take care of his sissy needs and promised to give the sissy a noght to never for... Continue»
Posted by lauraslollipop 5 months ago  |  Categories: Fetish, Group Sex, Shemales  |  

My 1st experience with a "Special Girl".

Let me tell you something about myself. I'm your average Hispanic male. I can honestly say I'm not gay or attracted to men. In contrary, I'll truly get turned off by that scene. Im also turned off by hair/hairy skin and bad hygiene (who isn't... LoL). It's just not for me. Yet something about a cute shemale with a booty is something i cant resist. I found myself enjoying shemale porn. A cutie with a booty takibg it up her booty hole. My favorite scenes involve a passable tranny (Ts Foxxy, Sianna Grace, Ts Celeste, etc.) Wrapping her ass cheeks around a dick. Skip the scenes were shes getting a... Continue»
Posted by socal805 5 months ago  |  Categories: First Time, Shemales, Taboo  |  
  |  3

My Mom The BBC Shemale and My Wife, The Virgin

After the wedding, we didn’t move out from my mother’s house as my salary is not enough to cover our expenses and since my wife is also not working.
Mom allowed us to stay with her since she will be living alone if we move out.
I had no issues with this as I save my expenses and on an off without my wife’s knowledge I can suck mommy’s dick and be fucked by her. Mom is also looking forward to this encounters I suppose.
Her age is pushing 60 but she still looks attractive most probably to her testosterone production that delays her menopausal syndromes. She still maintains her cock size which... Continue»
Posted by yarracuda 5 months ago  |  Categories: Mature, Shemales, Taboo  |  
  |  3

shazza my first bi experiance chapter 2

Hi everyone I hope you read chapter 1 because you will understand chapter 2 a lot better this is a true story which some of you might be able to relate to.
I was a little confused with my little episode with Fred I wasn’t sure what I wanted I had wanked another man’s cock and I had let him cum over me was I becoming gay even though I had a girlfriend, Just thinking about it was making me horny I would have to talk to Fred but I felt sort of embarrassed I needed to collect my undies he was washing for me, I often used to pop in to see him to ask when my next driving lesson was or when we were ... Continue»
Posted by cdshazza 5 months ago  |  Categories: First Time, Masturbation, Shemales  |  
  |  11

Moving in with Jim and Candy - Part 5

Not long after the scene with the pool guy and Janice occurred, Jim was called out of town on business for a few days. A couple of days after he left, Candy and I were eating dinner and just chit chatting about things. It was getting late into the summer and college would be starting soon. Candy took a sip of her wine, "So are you going to try to keep working at the store while you're going to school?"

I shrugged , "I'm thinking about it. I already talked to the owners and asked them if I could have a couple of weeks off while I was getting used to the school schedule. They said sure. I'm g... Continue»
Posted by Mrtommyboy 5 months ago  |  Categories: Anal, First Time, Shemales  |  
  |  2

Owned and Bred

'When we meet, that's it, you're mine. And then I'm going to fuck ya and breed ya.'

So said Conor at the end of the last phone message before I traveled to Dublin to meet him. For the first time. Though I had known him for years in Internet chat rooms and numerous phone calls. But no, we had never met.

I had tried to - on two occasions. I had booked an hotel room in the city centre and he couldn't wait to see me and again he had said the same thing.

'When we meet, that's it, you're mine. And then I'm going to fuck ya and breed ya.'

Except we hadn't met. He canceled - at the las... Continue»
Posted by sissypansyfairy 5 months ago  |  Categories: Shemales  |  
  |  2

What would it Take??

What would it take, to entice a nice handsome black man into my life?
Maybe if, the first time we met in person, meeting him at the door, dressed in my shortest mini skirt, highest "cum fuck me heels",toenails done in a bright pink to match my fingernails, advertising my sissy attitude, my tanned legs encased in a pair of thigh high fishnets, and a top that pushed my little A cups up and out. My nipples, hard as steel, straining against the material, wanting to be the center of his attention..
With my "sluttiest" make up on.. lips with the brightest red lipstick, outlined to perfection. The ... Continue»
Posted by bobbie_lee48 5 months ago  |  Categories: Shemales  |