Shemales Porn Stories
Page 3

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 2 years ago  |  Categories: Mature, Shemales, Taboo  |  
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Tricked by a shemale

I was out with a couple of guys from work, Brian and Dave, and we were having some drinks at a local bar. I'd never been out with them before, but they invited me and I didn't want to be rude.

While we were having our drinks I had made some negative comments about gay men at one point, you know how it is, right? Just trying to make some conversation, but they hadn't said anything back, negative or positive, but they did exchange a look that I didn't think about until later... much later.

Brian ordered us another round and I excused myself to take a leak. All I remember after that was ... Continue»
Posted by kevinj631 14 days ago  |  Categories: BDSM, Gay Male, Shemales  |  
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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 10 months ago  |  Categories: Anal, Shemales, Taboo  |  
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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 1 year ago  |  Categories: Fetish, Interracial Sex, Shemales  |  
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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 4 years ago  |  Categories: First Time, Interracial Sex, Shemales  |  
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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 6 months ago  |  Categories: Fetish, Shemales, Taboo  |  
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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  |  
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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 1 year ago  |  Categories: First Time, Shemales, Taboo  |  
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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 2 years ago  |  Categories: Gay Male, Mature, Shemales  |  
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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 1 year ago  |  Categories: Shemales, Taboo, Voyeur  |  
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Date Night (femdom classic)

DATE NIGHT (femdom classic)
A wife turns her husband into a sissy slut who is f***ed to service other men and women.

Tonight was"Date Night" and as usually was the case, I'd spent
the day in a high state of anticipation. My wife, Chris, and I had
created the "Date Nights" several years ago to merge our divergent
sexual desires into a mutually satisfying relationship.

My sexual tastes ran to the more exotic side of the spectrum bondage,
f***ed oral sex, prolonged sessions, feminization and role
reversal were exciting fantasies for me. Chris playing the
dominant role was a... Continue»
Posted by ssspspb 1 year ago  |  Categories: Fetish, Shemales  |  
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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 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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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 11 months ago  |  Categories: First Time, Shemales, Taboo  |  
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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 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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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  |  
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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 1 year ago  |  Categories: BDSM, Fetish, Shemales  |  
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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 1 year ago  |  Categories: BDSM, First Time, Shemales  |  
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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 1 year ago  |  Categories: Shemales, Taboo  |  
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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 1 year ago  |  Categories: Taboo, Shemales  |  
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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 2 years ago  |  Categories: First Time, Shemales, Taboo  |  
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