Shemales Porn Stories
Page 3

Fucking my friend's little sibling

After a night out I stayed over at my friends sl**ping in the spare room. In the morning my friend had work and left without waking me but she told me the night before she had work and I could stay until she got home again.

Waking up in the morning I felt groggy and tired but one thing I did notice was I woke up with morning glory, I was rock solid and made a huge tent of the quilt. I needed to sort this out. I slid my hand down into my panties where it was stretching them and slid them off allowing my cock to grow to it's full size, I was so horny and instantly began wanking to hard and f... Continue»
Posted by shemalecharlotte 1 year ago  |  Categories: Masturbation, Shemales, Taboo  |  Views: 7566  |  
100%
  |  11

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: 7563  |  
98%
  |  11

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 pleasurenfun 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 7544  |  
100%
  |  11

Loved it in my ass

Hi all
It all started very innocently but turned into an obsession.
Me and my girlfriend (Karen) at the time had a perfectly normal if slightly boring sex life, wow was that about to change. One night we were at it and in the heat of passion she wanted me to fuck her arse which is something i had never done previously, at the time it would not have mattered what she asked i said of course and dutifully filled her lovely arse with my hard cock, it felt so tight and good that within minutes i was spraying her arse with my hot cum. She smiled a looked at me and commented on how good that was an... Continue»
Posted by blueone71 1 month ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 7499  |  
100%
  |  6

My Shemale Mom and Aunt



I'm 5 feet and six inches tall I weigh 135 pounds soaking wet with long brown hair. Mom and Auntie Karen are both 6'2" with huge breasts and long legs. I walked into the Den to see them watching some shemale porn together. I sat down across the room from there with trembling knees and tears running down my cheek on the right side. Mom said come and sit down next to us, so I crossed the room and sat between them they both kissed me on the cheek and said We have a confession honey.

Timmy I'm not shocked that you wear my underwear I just wish you had told me.
You see I guess I only have m... Continue»
Posted by sissytimmy 1 year ago  |  Categories: First Time, Shemales, Taboo  |  Views: 7365  |  
100%
  |  4

Black Man's White Pussyboy (sissy fucktoy for



Black Man's White Pussyboy

Story from the perspective of a white pussyboy who gets fucked and dominated by a couple of nigger bucks. He also meets another pussyboy but ends up getting fucked by everyone. Good dialog.

I let Jay into the apartment. He was looking for a one bedroom,
furnished place and had called about my ad in the newspaper. I hoped to
rent this place quickly, then I would be full and could devote my time to
some maintenance and repairs rather than showing places. I looked at the
rental application he had filled out just a minute earlier. From the date
... Continue»
Posted by ssspspb 8 months ago  |  Categories: Fetish, Interracial Sex, Shemales  |  Views: 7357  |  
100%
  |  21

High School Cocksucker Outted (another story)

When I was 16 I slept over at Kyles a lot. Mostly I slept over because he'd fall asl**p while we were playing video games and watching tv. It was up to me whether I stayed and slept or went home. Kyle is black about 6'2 and has a strong build. He has a white Mother (Molly) and a black father (Wayne). He has a s****r named Jazyln who just entered high school. She has her mothers facial structure and a tight little body with breasts that seem to spring over night to about a large B cup. She was sexy and I always had to be careful when I was checking her out. Once or twice I caught her coming out... Continue»
Posted by Msgrv32 10 months ago  |  Categories: Taboo, Shemales  |  Views: 7275  |  
81%
  |  6

After School Dick-tention

I was late for class. Again. I slowly opened the door to my classroom, hoping Ms. Peterson was absent. Just as I managed to open the door enough to peer inside the class, I saw her. She had her back to me, as she was writing down notes for the students to copy, on the blackboard. I couldn't help but admire her form. This was her first year teaching high school history, and she had no shortage of teenage boy admirers. She was tall, I don't know how tall she was bare foot, but in heels (which she always wore) she was taller than most in the school; faculty or student. If I had to guess, I would... Continue»
Posted by SlaveX 12 days ago  |  Categories: Anal, First Time, Shemales  |  Views: 7180  |  
100%
  |  2

Fun with the Mechanic

Last weekend, I had a date to go out to a bar with some other CDs in another state and a 2 hour drive. I would get dressed when I got to the motel. On the way I had car trouble, but kept driving to the motel. Told the girls who were already dressed that I couldn’t go to the bar or play because I could not relax knowing my car was having problems. I was so horny because we had set this date up a few weeks ago and I had spent the day trying on my new sexy short black dress and getting ready.

I left the girls at the motel and headed home with the car having transmission problems. On the ... Continue»
Posted by hotcdsub 3 months ago  |  Categories: Fetish, Hardcore, Shemales  |  Views: 7154  |  
100%
  |  2

Fitting Room Fun

It’s about 8:45 at night and I am at this department store looking for some new clothes for the weekend partying. There weren’t too many people in the store, just an older married couple, a few employees, some teenagers, and a mother with her k**s. As I am headed towards the jeans/bottoms rack I notice a girl in some skinny jeans bending over. She had a cute little ass and a thin, slender body. She was pretty short about 5’4” with hair just down to her neck. I was about to walk up to her when suddenly she starts heading in my direction. That was when I noticed that she wasn’t a girl at all, bu... Continue»
Posted by pleasurenfun 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 7087  |  
100%
  |  9

My Transformed Wife

"Sometimes I wish I just had a dick," my wife said, wincing and squeezing her heating pad into her abdomen. She said this at least once a month, when her period would bring on two or three days worth of cramps and bloating.

I grinned and rubbed her stomach, "If you had one, you would just spend all your time playing with it and peeing standing up."

She giggled and squeezed my cock through my pants, "That doesn't sound so bad."

We never said anything beyond this, but from the first time she had mentioned it, it sparked a desire within me that I had never known I wanted. I had always ... Continue»
Posted by drew1207 1 month ago  |  Categories: Fetish, First Time, Shemales  |  Views: 6877  |  
100%
  |  4

black man's sissy boy

I started jerking off to ejaculation when I was around 18. Once I started doing it, it was all I thought about, 27/7 it seemed like. I collected fuck mags and porno tapes wherever I could find them, to use as visual aids. Just looking at those sexy nude women being loved up by their hot men made my dick so fuckin' HARD! Because of that I was able to convince myself that I was normal, of course, in retrospect it is obvious that I was identifying with the women.

One day when my mom was at work, I was laying in her bed, masturbating. I got up and rummaged through her underwear drawer. The draw... Continue»
Posted by nicoleinberlin 1 year ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 6840  |  
100%
  |  10

Young sissy loses her virginity (true story)

So this is a true story about the 1st man that I ever met. I was about 13/14 years old and had been talking to a much older man over the internet. He was about 50 if I remember correctly.

I had been dressing in my mother’s underwear and dresses for a few years and found it so sexy, I had not considered myself gay or bi, I just knew I belonged in female attire, it made me happy and felt natural.

The thought of pleasing this man made me excited, terrified and scared, but very excited. I could tell from my little clitty. After chatting for a few hrs he wanted to meet me?

I had never me... Continue»
Posted by Subtvnicola 1 month ago  |  Categories: First Time, Shemales, Taboo  |  Views: 6790  |  
100%
  |  5

Boy gets Fucked by Shemale

This is the story of my first she male. I had always been curious about dicks. I had always been attracted to women and I loved to watch a woman get pounded by a big cock. But after awhile I realized that when I tried to imagine the porno, I always imagined myself in place of the girl. One day, when I was sixteen, I decided to see what it felt like to be a girl. I had never tried anal before (I could never bring it up to my girlfriend) but I knew I had to try something. So I gathered all the necessary tools and went into my room. I locked my door so my mom wouldn't accidentally walk in on me a... Continue»
Posted by ClassicCockx 8 months ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 6767  |  
97%
  |  18

FUCKING UNCLE BOBBY

The title of this story isn't really accurate as I wasn't fucking Uncle Bobby see Uncle Bobby was fucking me! He wasn't really my uncle he was just my mother's boyfriend but he lived with us so it was kind of like he was my Dad I really like him a lot he gave me lots of attention and took me places and gave me money for doing chores for him he really was a good guy! He had a boat and it was a nice one too he kept it docked at the Marina and one weekend he asked me if I wanted to go fishing with him well I loved to fish and I loved boats so hell yes was my response and we set out to go fishi... Continue»
Posted by laceysgirl 7 months ago  |  Categories: BDSM, First Time, Shemales  |  Views: 6709  |  
94%
  |  3

my wife make me her sissy slut

I married Jen when I was a successful high earning bachelor at the age of 30. She
was 25 at that time. 5'4" same height as me, 120lbs, petite blonde with
blue eyes, a set of DD tits and an ass to die for. I was short, skinny yet she was
attracted to me when we first met in a bar down town. Later on I found out that it
was Laura her friend who had told her that the porsche parked outside was mine.
Now, after 5 years of marriage, things were quite different. Things had actually
started going down hill after the first few months when subsequently Jen had clearly
stated that my 3 inches coc... Continue»
Posted by nicoleinberlin 1 year ago  |  Categories: Gay Male, Shemales  |  Views: 6676  |  
90%
  |  5

A Lodger's Leanings

By - Lucy Roberts

A Lodger's Leanings

I was brought up by my Mum as my Dad left us when I was very small.

Mum and I had a good relationship and, only having a female role
model, perhaps it wasn't surprising that I got into wearing my Mum's
clothes. At least that was where it started but as I entered my
teens I used quite a bit of the money given to me at birthdays
and Christmas to buy my own clothes.

By the time I was about 13 I was used to having the house to myself
while my Mum was at work. As well as being able to have friends over,
it gave me plenty of opportunity to ... Continue»
Posted by jayymie 6 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 6660  |  
100%
  |  5

Daddy's Girlyboy

I was alone in the house so I was indulging in my fantasy of dressing up as a girl. I had my long hair all straightened, full make up and my skimpy sheer black thong on with black stockings and suspenders with a tight lycra dress which showed off my very girlish figure. This was finished off with a pair of killer heels which complemented my shapely, smooth legs. Dad wasn't due in for a while yet and mom was away on business. I put some music on and was enjoying being the real me for a while.

I was dancing to my music and looking at myself in the mirror when dad came bursting through the do... Continue»
Posted by sexycock3 1 year ago  |  Categories: Gay Male, Shemales, Taboo  |  Views: 6646  |  
100%
  |  18

First Time - Surprise Shemale

I'm an eternal masturbator. I've always like wanking and playing with myself. At a young age I worked out that I likes playing with my ass hole, sticking things in it, walking round all day with something in it. With the advent of the internet I was like a pig in shit. So much porn to be had and so many things to see and do. One day I discovered the true beauty of the shemale. Wow. Gorgeous women, with cocks. Prior to this it had been women with strapons that got my attention, but this? Perfection. Then cam the webcam. I found a couple of sites where you could interact with such beauties and c... Continue»
Posted by hungrymanx 2 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 6638  |  
100%
  |  3

The Postman Always Rings Twice

After I moved away from home, I felt pretty good. No one could tell me what to do. I missed only one thing: The closet of my big s****r. Since I was 13, I regularly wore her clothes, especially the underwear. As soon as I was home alone, I went to her room, and started to try on her thongs, bras and stockings. At the same time I played with my little clit and sometimes I slid some vegetables into my boypussy.
I really missed these little dress-ups, so one evening I decided to buy some own lingerie. For the beginning I ordered a cute bra with a matching thong and a pair of thigh highs. I could... Continue»
Posted by notgeile_fickstute 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 6581  |  
100%
  |  6