Shemales Porn Stories
Page 3

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 10 months ago  |  Categories: Shemales, Taboo  |  Views: 7875  |  
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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 10 months ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 7778  |  
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Fucked by daddy's friend

This story was a fantasy of mine from when I was about 11yrs and still think of it happening now even tho the guy in question, is in his mid 60's

I'd be at home from school alone as my parents were at work. This is when I would go through my mums sexy underwear draw. I picked out a black suspender belt, matching bra and see through panties and some black seamed stockings. Luckily I was young enough to have a hair free body and was the same dress and shoe size as my mum. So I picked out a dress theat finished half way up my thighs but covering my stocking tops and a gorgeous pair of black 4"... Continue»
Posted by danny241976 29 days ago  |  Categories: Anal, Shemales, Taboo  |  Views: 7716  |  
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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 11 months ago  |  Categories: Fetish, Interracial Sex, Shemales  |  Views: 7628  |  
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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: 7591  |  
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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: 7563  |  
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school teen gay crossdresser first time sex

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 new 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 new 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 w... Continue»
Posted by allisontranny 2 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 7494  |  
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Sissy picked up in hotel

...
you are having a drink at the hotel lobby bar, another night in a hotel working away, sipping your drink thinking how you are becoming sick of the same boring hotel routine and looking around at the people checking in and out, the bar is relatively quiet for this time of night.

A girl walks up to the bar next to you and asks for a drink, you glance over and the first think you notice is her bobbed blonde hair, down to just below her jaw line, she catches your eye and you become more interested. You give her a quick look up and down, not really caring if she catches you out as you are ... Continue»
Posted by JasmineSissyCD 11 days ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 7476  |  
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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: 7474  |  
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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: 7421  |  
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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: 7391  |  
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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: 7296  |  
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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 4 months ago  |  Categories: First Time, Shemales, Taboo  |  Views: 7223  |  
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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 5 months ago  |  Categories: Fetish, Hardcore, Shemales  |  Views: 7163  |  
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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: 7130  |  
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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: 7087  |  
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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 10 months ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 7002  |  
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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 3 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 6932  |  
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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 2 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 6846  |  
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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 3 months ago  |  Categories: Fetish, First Time, Shemales  |  Views: 6846  |  
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