Shemales Porn Stories
Page 4

Sissy's first BBC

This happened awhile ago, i was 19, and i figure some people have asked me to write more so here goes =]

I was lookin around on craigslist... so i was horny and wanting it! Scrolling around and found a black guy who wanted some ass. No real specific requests, so i figured i may as well reply. In my town it is a bit rare to find black men who are down to fuck a sissy! I had sucked one BBC before while visiting North Carolina, sucked him off in a park which was great =] But that is another story and not nearly as entertaining.

So he replied back. Very little info. A pic of his cock... whic... Continue»
Posted by AshleyXmith 9 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
9392
  |  
100%
  |  16

Captured and Turned

HI, this story is fiction. I hope you like it.
-------------------------------------------------------------

I was confused as I found myself coming to consciousness. I say coming to because the last thing I remembered was having dinner with my friend Joe and his wife Stacie.

I was in a dark room and my vision was blurry. I felt restraints holding my arms behind me and I was in a wooden chair.

"What the fuck?"

More and more senses returned and I found myself fully conscious now. I was tied to a wooden chair completely naked with my legs secured to the chair's legs and my a... Continue»
Posted by kevinj631 1 month ago  |  Categories: Fetish, Gay Male, Shemales  |  
9377
  |  
95%

The First Time My Ass Pussy Was Fucked

There's something about having my ass pussy penetrated and pumped during sex that makes me feel more feminine sexually. Perhaps it is the fact that the entering of me, the taking of me, the domination and seeding of me, that feels so right for a gurl like me.

Not too long after I started living as a gurl openly, a neighbor of mine at the small apartment complex where we lived introduced himself to me. He spoke British English which I find so charming and a bit arousing. We got to talking and found out we both had a lot of similar interests and backgrounds. I lived alone in my apartment,... Continue»
Posted by kinkyjodigurl 1 year ago  |  Categories: Anal, First Time, Shemales  |  
9363
  |  
100%
  |  28

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 3 years ago  |  Categories: Mature, Shemales, Taboo  |  
9234
  |  
92%
  |  7

The new "Girl" On the Boat

I have mentioned in previous stories that my career was spent as a Captain of a high end 100' charter yacht working the waters of Alaska. It was a job that provided me many opportunities to 'play' with men, women and couples, most of them older, and all of them very well-off financially.

Passengers and crew had to sign agreements that I could inspect their rooms and belongings for any reason whatsoever, though I assured them it was very unusual for me to do so. For the crew, my main reason for conducting such inspections would be to check for i*****l d**gs.

But another reason for chec... Continue»
Posted by 1kaaboom2 1 year ago  |  Categories: Hardcore, Shemales, Taboo  |  
9189
  |  
93%
  |  6

My Uncle Wally's Sissy Boy Wife

Penned by: Miss Deborah (Debi) Leigh Johnson



One



I did not know what I could expect, as the Greyhound pulled into the
bus station. I did not know a whole lot in fact, as I was a rebellious
know it all, fifteen year old brat.

My parents were pretty good as far as parents went. I had not locked a
roof over my head, or enough food on the table, but I had always
resented the fact that my parents were not rich enough to give me
everything that I wanted. I knew in the back of my mind that this was
a pretty immature attitude, but what the hell, it was the way I
felt. I also di... Continue»
Posted by jayymie 2 years ago  |  Categories: First Time, Shemales  |  
9174
  |  
99%
  |  22

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 3 years ago  |  Categories: Gay Male, Mature, Shemales  |  
9005
  |  
100%
  |  12

My CD / Sissy story and 1st meet humiliation

I recently met up with someone to be a sissy slut for them and wanted to share what happened on my first meet. This is the genuine true story. I use the username indoblu on websites, but my sissy name is Holly so I'll refer to myself from now on as such. I'll mention my history as a sissy before talking about the meet up, skip the first few paragraphs to get to that bit.

I have always known I love girls clothes, lingerie, miniskirts, colourful sheer blouses , anything satin or lace, since a very young age. When I was 18, I finally had a credit card, and bought my own lingerie. I bought clot... Continue»
Posted by indoblu 1 year ago  |  Categories: BDSM, First Time, Shemales  |  
9007
  |  
99%
  |  51

Tranny Surprise Part 2

Things were off to a good start with Dani. We have been texting each other throughout the week just talking and setting up another date. We decided to go to the local fair I picked her up around 530 and she wasnt quite ready yet so she let me in hugged me and went back to finish her hair. I sat on the couch and played with her cats for a minute, she was back in no time and she looked great!

"Wow Dani you look really pretty in that sun dress." I said. "Thank you" she replied with a big smile.
We got to the fair and we went in we wa... Continue»
Posted by Entities 7 months ago  |  Categories: Shemales  |  
8951
  |  
93%
  |  12

Tranny Surprise Part 1

After being cheated on for months here I am alone in a bar having a drink. I dont understand whats wrong with me im above average in looks, im fit, im successful for my age. Its time I move on though and so far no girls ive dated have been worth a second date. As I look around the bar I see her.
I immediately start to stare. Looks like she was there with a couple of her friends. I order another beer and decide to scope it out for a little bit. I just couldnt get over how pretty she was. She was tall, thin, and had the cutest smile... Continue»
Posted by Entities 7 months ago  |  Categories: Shemales  |  
8939
  |  
91%
  |  13

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 year ago  |  Categories: Anal, Shemales, Taboo  |  
8903
  |  
100%
  |  9

The Making of a Sissy (Part 1)

It was the summer after graduation, and I was living with my mom who was recently divorced. She had been dating a lot during that period, which was kind of rough for me to deal with. I would usually give her dates a hard time, and to be honest I was completely unsupportive of her decision to be dating. Anyhow, I was up late one night watching something on t.v. when I heard her and her new boyfriend come home from a date. They were apparently somewhat d***k and making a lot of noise, but I just tried to ignore it. It wasn't much longer until I started to hear this moaning and rocking of th... Continue»
Posted by briantid8 6 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
8853
  |  
100%
  |  10

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 5 years ago  |  Categories: First Time, Interracial Sex, Shemales  |  
8837
  |  
85%
  |  22

Working Gurl

Working Gurl

My name is Danielle and I’m a working gurl . I started working in 1991 at the age of 20, my first job as a hooker was working out of an Adult Book Store North of Ft. Worth, Texas on I-35W South of the airport My boss was an older tranny named Jannice she ran the book store. On nights when she would call me in she would set me up in a booth in the video room. I never knew who or how many would come in to my booth. I was to service all that came to see me. Was I doing this for the money? Oh hell no I was in it for the cum. But the money was good too.
It was a Saturday night arou... Continue»
Posted by danigurl69rt 9 months ago  |  Categories: Anal, Fetish, Shemales  |  
8720
  |  
86%
  |  4

T Is for Teresa


It was when I was still living at home, or at least staying there in the college holidays, that Mum came home and found me and Jack Horton lying on the living room floor, naked, and giving each other sixty-nine. She knew I was gay, or course, but was still shocked. As was Jack.

After he'd dressed and left, literally with his tail between his legs, my mother and my father came into my bedroom together. Looking grim. I thought I knew what was coming, and I was in fact right.

"Terry, look. When you've l... Continue»
Posted by Batman_112 1 month ago  |  Categories: Taboo, Shemales, Gay Male  |  
8674
  |  
97%
  |  5

Sucking My first cock

It all started earlier this week, I had begun to watch a lot of sissy hypnosis videos and training videos, mainly ones from Polish Mistress.

Every time I watch these videos, I usually would just end up masturbating or going on Cam/Phone with someone. But, after watching a 35 minute faggot hypnosis video, I was completely under the spell of the cock. My inner-desire took over after that.....and well this is what happened.

After being completely hypnotized, I went online and luckily enough found a dom daddy type guy in my area in a chat room. I told him I had never sucked a cock before, a... Continue»
Posted by pantycum666 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  
8571
  |  
97%
  |  25

Met 2 s****rs with a secret

Synopsis: First of all, I want to apologize. I konw it's been a really long time since I posted anything. I just haven't had much time to write. However, I think you'll find this story worth the wait.

This story is about a young man who heads off to college in New Zealand and meets two beautiful s****rs. Before long, a relationship develops between our hero and one of the s****rs. Of course, if you've read any of my stories, you know there's more to this girl than meets the eye . . .

* * *

I want to get one thing out of the way before I start my story: I'm not gay. It's not a denial t... Continue»
Posted by drew1207 1 year ago  |  Categories: Fetish, Shemales, Taboo  |  
8531
  |  
100%
  |  5

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 3 years ago  |  Categories: First Time, Shemales, Taboo  |  
8533
  |  
100%
  |  4

Shemale Surprise

anal – shemale – transgender – transsexual – oral – pantyhose – first time – stockings – wedding – lesbian

"You can stay with Robert if you wish," Mary said on the phone.

I looked up from my laptop where I was pretending to be working when, in reality, I was reading, for the hundredth time, the brilliant novella 'Shemale School: a Teacher Seduced'. The story had created a new obsessive fantasy I had never even considered before: to be with a Shemale.

I even contacted the authoress to tell her how much I enjoyed it, and have since became one of her editors. I had just finished e... Continue»
Posted by naughty_bi_interest 2 months ago  |  Categories: Anal, First Time, Shemales  |  
8517
  |  
97%
  |  19

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 2 years ago  |  Categories: Anal, Masturbation, Shemales  |  
8427
  |  
100%
  |  5