Shemales Porn Stories
Page 3

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 9 months ago  |  Categories: Shemales, Taboo, Voyeur  |  Views: 8258  |  
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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  |  Views: 8026  |  
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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 7 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 7958  |  
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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 1 year ago  |  Categories: Gay Male, Mature, Shemales  |  Views: 7921  |  
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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 5 months ago  |  Categories: First Time, Shemales, Taboo  |  Views: 7916  |  
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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 11 months ago  |  Categories: Shemales, Taboo  |  Views: 7869  |  
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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 11 months ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 7784  |  
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Mom Loves Not Her Daughters

IT SEEMED LIKE the ideal time. Amy was at school and mom had gone to shop
about an hour before. I had waited purposely to make sure she hadn't
forgotten something so she would return right away.
I'd been thinking about it for a long time. I mean, I'd looked at mom
and s*s's stuff before. But that was only in the bathroom where they
sometimes hung things around or in the dirty clothes or even in the washing
machine if I had to load and unload it.
I went to s*s's room first. It was really pretty disappointing. I
mean, she had panties and one spare little training bra but that ... Continue»
Posted by BeeJay69 16 days ago  |  Categories: Shemales, Taboo  |  Views: 7756  |  
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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  |  Views: 7676  |  
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Shemale massage

It has been one of those long and stressful weeks. I’m in desperate need of relaxation and relief so I head over to an Asian massage parlor for a typical happy ending massage.
The girl who usually massages me isn’t available so another girl is suggested which I accept. I think to myself that she can’t be much different than my usual so I don’t care much. I just need a massage badly.
She comes out of the back from another massage and introduces herself as Jessica. I smirk a bit knowing there is no way her name is Jessica but I go with the bit and am happy as she is quite attractive and alread... Continue»
Posted by malesub01 1 year ago  |  Categories: Shemales  |  Views: 7594  |  
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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 pleasurenfun 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 7562  |  
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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 5 months ago  |  Categories: First Time, Shemales, Taboo  |  Views: 7542  |  
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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  |  Views: 7543  |  
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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: 7441  |  
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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 1 year ago  |  Categories: First Time, Shemales, Taboo  |  Views: 7370  |  
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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  |  Views: 7280  |  
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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 6 months ago  |  Categories: Fetish, Hardcore, Shemales  |  Views: 7154  |  
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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: 7100  |  
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Turned into Jasmine by BBC :)

It was just another warm Sunny weekday morning like any other in summer. My wife kissed me goodbye as she left for work, I took my usual pervy glance at her as she wiggled her hot behind out the door, I was setting up in my home office, ready for another day of working from home.

I listened to the car roll out the driveway then the gate closed, I started working through the usual emails and meeting requests.. I got bored of work after a couple of hours I decided to go into our bedroom and rifle through my wife's huge array of skimpy clothes and sexy Lingerie as we had just had a very steam... Continue»
Posted by JasmineSissyCD 1 month ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 7098  |  
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Horse Cock Girl 6


A few days after going to the club with Lucy and Scarlet, Amy was on her lunch break at work, thinking deeply. A lot of things that had happened or been said that night had stuck in her head and it had been bugging her since. Everything she was thinking about was to do with her relationship with Lucy and Scarlet.

She'd been thinking about something since even before the club: marriage. She loved Lucy and believed that Lucy lover her too. She was, however, wondering if, were she to ask Lucy to marry her, Scarlet might get jealous. Amy didn't want that, because both she and Lucy loved Scarl... Continue»
Posted by drew1207 13 days ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 7063  |  
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