Shemales Porn Stories
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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  |  
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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 2 years ago  |  Categories: Anal, First Time, Shemales  |  
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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 10 months ago  |  Categories: First Time, Shemales, Taboo  |  
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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 1 year ago  |  Categories: First Time, Shemales  |  
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How My Life Changed

How My Life Changed Chapter 1

My wife Mary and I had been married for over eight years and I thought
our life was very good. She was an attorney for an important law firm
and rapidly rising towards a partnership. She made a lot more money than
I did in my job as a fast food worker. That didn't bother me as much as
it might have many men. We had a nice house and lived well. Mary is 28,
5'6", 120 pounds and had 38D breasts. She is a beautiful brunette with
brown eyes. I am 5'8", 140 pounds and used to taking orders from the
people I work for. As my wife gained more power ... Continue»
Posted by klammer 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
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First Blowjob

I pulled into the reststop needing to pee badly. As I walked into the restroom, I spoke briefly to a trucker, and went about my business. While I stood there peeing, he took a peek at my dick. At the time, I hardly even noticed it.

As we went to leave, he said he was going the same way as I was and would be monitoring his CB radio for reports on where cops might be. He then invited me to follow him. I agreed since I wanted to make good time. We drove for about an hour when he pulled over. I thought maybe something was wrong so I pulled over too.

He got out and walked back to my truc... Continue»
Posted by KaylaCD15 3 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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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 2 years ago  |  Categories: Masturbation, Shemales, Taboo  |  
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A Special Little Girl ( I did not write this )


"Your hair is getting so long now." The Mommy says as she smooths
Erin's wavy blond hair down. "I think we should take you to get it cut."

"No Mommy, I like it long."

"Before much longer it will start getting into your mouth when you eat.
It might get annoying. "

Erin thought a moment. His head down, hesitantly, not wanting to upset
The Mommy he says: "But, I like the way it feels when it's long."

"How does it feel, Erin?"

"It makes me feel pretty like you are Mommy."

The Mommy's heart warmed over. She likes it when her son says she's
pretty. I... Continue»
Posted by whiteshadowz 8 months ago  |  Categories: Fetish, Hardcore, Shemales  |  
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My First Time Dressed as a Girl (PT 3) (Consequenc

Well. I had written a follow up to ‘My First Time as a Crossdresser, PT 2” but Microsoft decided that the moment I attempted to upload was the perfect moment to update and erased the whole story, which means I had to rewrite the whole thing. So...

After I dressed in the schoolgirl outfit that Gunther had put out for me, I pulled my hair into a high ponytail and put on makeup emphasizing my eyes and lips without going overboard. I walked out into the living room to discover that Tracey had left and Gunther was dressed in a pair of slacks and a very expensive looking Cashmere cardigan. He s... Continue»
Posted by sbobbi66 4 months ago  |  Categories: Fetish, First Time, Shemales  |  
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My Girlfriend's Mother Has a Secret

A young man, 18, is caught spying on his girlfriends mother in her bedroom, and is taught a hard lesson. Characters: Tim, 18, Student; Susan, Tim's Girlfriend; and Julie, 44, Susan's Mother ;-).

Julie sat at her dressing table, preparing for bed; she brushed her long dark, which was one of the pride and joys. Normally, this would help her relax and unwind, but tonight, and on several other nights, she found that remained tense. She couldn't get over the feeling that somebody was watching her, for several days, perhaps a week; when she was alone around the house; she'd have an odd sensation ... Continue»
Posted by Asmarani 5 months ago  |  Categories: Anal, Mature, 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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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 11 months ago  |  Categories: Fetish, Hardcore, Shemales  |  
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My Big Sister

I must say I never pictured this event happening to me in my lifetime, I mean I'm a pretty well rounded k** living in a quiet suburban town. Nothing big happens here, and I'm not some guy that's always finding himself in trouble, so getting bent over and fucked in my ass was the last thing I really worried about, unless I was gay of course, which I'm not.

But no, here I am at eighteen years old, a grown man feeling his ass burning as I try my best to sit comfortably at my desk. As the instructor goes on and on I find my eyes darting back and forth around the room, making sure no one looked... Continue»
Posted by sparkyking 1 year ago  |  Categories: Shemales  |  
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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 8 months ago  |  Categories: BDSM, First Time, Shemales  |  
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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 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
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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 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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A Nurses Fantasy

This is a fantasy. Very, very Loosely based off of my experience at a hospital over my 18th birthday. Enjoy!




When I was s*******n I found myself in the hospital for a few weeks. It just so happened that I was going to spend my 18th birthday in the hospital and was really bummed out at first, but I soon realized that being in the hospital wasn’t all that bad. Though the doctors set strict rules, I found out that the nurses pretty much ran the show because doctors never stuck around, and were pretty much never even in the hospital after noon. I am a pretty charismatic guy and my person... Continue»
Posted by wedgietime 3 months ago  |  Categories: Fetish, First Time, Shemales  |  
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My First Time Pt. 1 - The Boss makes his move

I was stocking boxes in the warehouse at plastics company. This was my after school job, at 18, not bad at $10 and hour.
My boss, Bob walked in behind me. I could hear him fumbling around, moving boxes. He was always in and out, so I didn't really care.
I didn't look back b/c i just wanted to get my work done and go home.
I knocked down a couple boxes which spilled some of the box filler, I was so fucking embarrassed. But hey shit happens even when it's bad timing.
I instantly dropped to my knees trying to scoop them into the boxes before Bob said anything.
I was wearing tight jeans and a... Continue»
Posted by adampanties 3 months ago  |  Categories: Gay Male, Mature, Shemales  |  
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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 6 months ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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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 9 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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