Shemales Porn Stories
Page 2

GF And I's Threesome With A Shemale (True)





This is the true story of when my girlfriend at the time and I had a threesome with a shemale off Craigslist. Enjoy


At the time of this story which was a couple years ago I was dating a girl named Miranda she was sexy,funny and kind of kinky which was everything I looked for in a girl I guess. We had been dating for about five months and after the third months we had begun talking about having a threesome with another guy or girl because Miranda and I are both bi... Continue»
Posted by xXSecondCitySaintXx 1 month ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 9851  |  
96%
  |  6

My Boss Tricked Me

I work for a cell phone company. Part of my job is to travel to cell phone towers and fix any problems they might have. I enjoy it but am on call most weekends. Now I consider myself a man in public but at home I love dressing up as a slutty tramp. I love the feel of lingerie on my body. I had a few experiences with a man but it was mostly mutual masturbation. My crossdressing is a secret to everyone except the few I have met online.

Most Friday nights me and the coworkers go out drinking. Just a bunch of guys out having a good time. One particular Friday I got really d***k and my superviso... Continue»
Posted by sissysadie 6 months ago  |  Categories: Fetish, First Time, Shemales  |  Views: 9812  |  
92%
  |  6

A Visit to the Doctor

I hadn't been to the doctor in years. But after a minor health scare with a friend, I decided I should go and get myself checked out. I made myself an appointment with a doctor nearby for the following week and waited nervously to go.

I had been born a male, but for years I have been presenting myself as female. I was really passable too, the only problem was my, well, you know. Not many people knew of horrid past, and I wasn't going around screaming it from the mountaintops either.

On the day of my doctor's appointment, I put on pink lace panties that covered most of my ass, a matchin... Continue»
Posted by Bangbangtrain 9 months ago  |  Categories: Lesbian Sex, Shemales  |  Views: 9737  |  
100%
  |  14

Caught by Neighbor

Caught by Neighbor


- 1 -

It was a beautiful warm day, and I had it to myself. My wife Sam was interstate on business for the week, and not due back for another five days. For me that meant housework to be done, but plenty of time to enjoy my own space, and entertain one particular hobby. I smiled to myself, and not for the first time, I stopped in front of a mirror and pulled my tracksuit pants down, admiring the bright pink, silky panties that I'd been walking around in all day.

I'd been cross-dressing for many years before I met Sam, but it really wasn't her thing. So I tended to ... Continue»
Posted by Femluver 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 9608  |  
98%
  |  22

Sissy out of control in the toilet

I'd describe as a fit rough looking submissive guy. Recently love to dress in panties and stockings and get interfered with....

One of the first and hottest experiences was in a quiet public toilet. It was about 3.30 on a summer afternoon and I'd had no luck down a nearby cruising area - which was unusual as it was normally reliable. The lack of action was most probably down to feeling slightly inhibited by what I was wearing under my shorts.

As I entered the cottage (as we call public toilets in the uk) and judging by the scurrying that occurred I'd interrupted a scene.

I went in ... Continue»
Posted by skins4skin 1 year ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 9585  |  
94%
  |  18

Feminized my Mother

My Mother divorced my Father when she found him in their bed fucking a neighbor girl he was eventually sent to prison, ever since then she's been on this anti men kick. When I was 14 I came home from school and saw My Mother rinsing some dishes in the kitchen so I snuck up behind her and grabbed her boobs, she slapped me and said go to your room or else.

I awoke the next day ,took a shower, went into my room to get dressed and couldn't find any of my clothes, I knocked on Mother's door, she said "Come in dear" I asked where my clothes were she replied I threw them out your not going to en... Continue»
Posted by sissytimmy 10 months ago  |  Categories: Mature, Shemales, Taboo  |  Views: 9502  |  
64%
  |  2

Caught

This is how I got caught masturbating and lost my virginity to my stepmom.
I was still in High School but had just turned eighteen, and was still living with my dad and stepmom, Beverly. I was ashy kind in school and did not get many dates, this lead to lots of jacking off. I did not realize it at the time but not only had my dad married a transsexual, but Beverly liked to sl**p around. I later found out my dad, liked it and enjoy hearing her tell about a how she seduced strait guys.
So I was watching some porn on the internet when Beverly walked in on me. I quickly changed windows and made ... Continue»
Posted by raastible 1 year ago  |  Categories: Mature, Shemales, Taboo  |  Views: 9199  |  
91%
  |  7

A young cross dresser's first gay experience

I was just a young boy then, senior in high school, horny as hell and dreaming of my first gay experience since sitting in my s****rs red lace thong and white lacy bra and discovering the one porno in the house everyone kept hiding from me. I guess they thought my s****rs panty drawer held no interest for me......they were wrong.

It had been a great afternoon jacking off in my s****rs bra and panties and watching my first porno when it happened, I saw the most beautiful thing ever, Peter north titty fucking a hot blonde and cuming all over her face. I was besides myself I could not believe ... Continue»
Posted by alex_boycd 4 years ago  |  Categories: Gay Male, Shemales  |  Views: 9047  |  
98%
  |  51

Caught wanking in school

This was my first sexual experience as a shemale, I was still in school, I loved the girls in the school uniform, tight white shirts so thin it would show their bras through and tiny short skirts, some flared and some really tight too, I would always end up getting a cheeky view up some of their skirts and I couldn't help but stare as their tight bald pussies or their tight perfect little asses. I had to wear that uniform too and I always had to wear little panties to hide my big cock.

We had just finished a P.E (Physical Education) lesson and we had all come back to the changing rooms, as ... Continue»
Posted by shemalecharlotte 1 month ago  |  Categories: Anal, Shemales, Taboo  |  Views: 8884  |  
100%
  |  7

Fucking And Getting Fucked By Dads Shemale GF

My name is Lisa and I am sixteen years old. I live with my dad and in a pretty nice apartment but we did have a house until my parents divorced and my dad let my mom have the house. My mom was always really rude to my dad and he just let her do whatever she wanted. Well eventually she had sex with a guy at her work and when my dad found out he divorced her. I can tell that its affect him way more then me because to be honest my dad is way to good of a person for her. The only good thing I got from my mom was her looks. Long dark hair, blue eyes and a tiny body that's developing quickly. I get ... Continue»
Posted by xXSecondCitySaintXx 2 months ago  |  Categories: First Time, Shemales, Taboo  |  Views: 8804  |  
100%
  |  2

First Time Having Sex With A Shemale

Ok let's begin so I was walking down the street going to the store one day I saw a woman and her daughter moving into a house they had some heavy boxes that they need help with. At first I thought she was white girl but when I got closer to them they we're Asian becuase i only saw the back and they hair was long that it cover their face so i didn't get a good look until they ask for my help with the boxes and 50" inch flat screen T.V. they had so i said yeah i'll help you then she was like thanks a lot it's was a nice home for her and her daughter. So we finish moviing stuff into the house and... Continue»
Posted by TheGhost08 3 years ago  |  Categories: First Time, Interracial Sex, Shemales  |  Views: 8603  |  
85%
  |  21

fucking my b*****r

It had been a long time since I last saw my b*****r.he was actually my stepb*****r, but it didn't matter.we had seen each other naked a lot of times, but still he didn't have any sexual interest in me.but me, I wanted him to fuck me.I was pretty young back then but still I bad lost my virginity and already had 2 daughters.as my b*****r entered my house kt was 11 o clock and no-one was home.but very soon I came home, and after seeing my b*****r I gave him a big hug.this made my books press against him and as my legs were touching his cock I cud feel it growing.I looked at him and blushed, he th... Continue»
Posted by sexynithya123 1 year ago  |  Categories: Anal, Masturbation, Shemales  |  Views: 8404  |  
100%
  |  5

my twink brother

I came home early from work one day and didn’t know anyone else was home. As I walked up the stairs toward my room I heard noises coming from upstairs and as I got closer I could hear they were coming from my room. When I turned the corner at the top of the stairs I could see my b*****r’s best friend sitting on my bed, but I did not see my b*****r. That is until I walked a bit farther.
I stood back from the door a bit and watched the show my b*****r was putting on for Jason. My b*****r Steve was wearing my short black skirt and hot pink tank top, the red wig I wore on Halloween. Steve made ... Continue»
Posted by CB1996 6 months ago  |  Categories: First Time, Shemales, Taboo  |  Views: 8319  |  
100%
  |  7

First Halloween

I have always been a skinny boy and not much muscle tone. Very feminine and so my older s****r started dressing me when we were alone at the house. I didn’t mind and most of the time I liked it because it allowed me be free. I felt more comfortable dressed as girl. Last Halloween I decided that I would let her dress me up as a girl and take me to a party of a friend of hers.
She did my makeup and fixed the wig I wore. I chose a white button up shirt and a black pleated skirt. I wore white stockings and white platform heels. The heels made butt stick out just a little. The wig I wore was red ... Continue»
Posted by CB1996 5 months ago  |  Categories: Shemales, Taboo, Voyeur  |  Views: 8258  |  
100%
  |  8

My friend's new roommate and her surprise

So my friend Rebecca and I were planning on going to this bar for the evening but she called me and said she was running a bit late and that I should wait at her place and that her new roommate Shawna should be there to open the door for me. Rather, than wait in my car I went upstairs to her apartment like she suggested. The door was slightly open so I walked in saying hello; to see if anyone was home. I heard some noise in the kitchen so I walked over to check it out. It was Shawna cooking. She was actually a pretty cute girl. She was wearing a white tee shirt that just about covered her ass ... Continue»
Posted by lovingitman 4 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 7953  |  
98%
  |  5

My fucking f****y

I'm really proud of this would love some feedback


Why was I on all fours with my dad's cock in my ass and my s****r's pussy in my face? Well little did I know that my mom knew about my secret. She knew that I had been wearing her and my s****r's lingerie.

It started when one day I was home alone and wandered down to the garage to play around on the air hockey table. I got bored and looked around as we had a lot of stuff down there. Boxes were piled up on one side and I looked in a few of them and found something that made eyes pop open.

I saw a naked girl on the cover of a magazine... Continue»
Posted by 6270daniel 2 months ago  |  Categories: First Time, Shemales, Taboo  |  Views: 7879  |  
96%
  |  7

Discovery

"What the hell are you doing!!?" I heard my s****r scream. My eyes snapped open, my hand flying away from its grip around my cock. With our parents away and my s****r out I'd thought I'd be alone for the evening and decided to have a wank. Now Michelle had come home unexpectedly and discovered me. It got worse. "Are those my knickers you're jerking off into?" She screamed again. I nodded shamefacedly. "You little shit. I'm telling on you."

"Please don't Michelle; I'll do anything you want." I pleaded.

She looked down at my lap where her panties were still wrapped around my now wilting ... Continue»
Posted by sparkyking 8 months ago  |  Categories: Shemales, Taboo  |  Views: 7873  |  
100%
  |  8

Cumslut Husband



Cumslut Husband


Part 1 - An Acquired Taste

"So, honey, what did ya get me for my birthday this year?" Smiling, my wife sucked a drop of butter from her finger and told me "It'd better be good."

Uh-oh. I'd completely forgotten about it, and I think she knew it. Stalling, I snatched a piece of toast from her plate and crammed it in my mouth, mumbling incoherently around it.

"You forgot, didn't you." Crossing her arms over her breasts, she just sat there and glared at me. I tell you - if looks could kill . . .

"As a matter of fact," I replied, "I didn't." Thinking quic... Continue»
Posted by klammer 8 months ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 7789  |  
81%
  |  4

feminized by my mother


Feminized By My Mother
My mom was staying in as were Jen's parents so we parked on a dark road and made out while I fingered her. Her panties were absolutely drenched when I was finished, and she rubbed her hand inside them and used her pussy juice to jerk me off, I spurted all over my pants and she laughed.

"I hope your mom doesn't see." She said.

"Actually she probably wouldn't care." I said.

"Oh yeah? In that case we should just have fucked in your house then."

"I wouldn't push it." I said jokingly, but she ... Continue»
Posted by nicoleinberlin 1 year ago  |  Categories: Gay Male, Mature, Shemales  |  Views: 7678  |  
100%
  |  7

In Hose and Heels for Daddy

It was shortly after my 14th birthday when I made the decision to seduce my Daddy. I mean, all of my girlfriends were having naked fun with their daddies. I didn't wanna be left out ;-) After all, me and my BFF, Ashley, had been getting naked and having fun with her daddy for 2 whole years now...and with her b*****rs...and with her uncles...and with her cousins...and with her neighbors...and with her...awwww, shit...you get the picture ;-)

It was the morning after my first experience with my Daddy. I was camping out in my back yard and had told some guys to come over for backyard blowjobs.... Continue»
Posted by cdsexslut 2 years ago  |  Categories: Anal, Shemales, Taboo  |  Views: 7609  |  
98%
  |  11