Shemales Porn Stories
Page 5

Rent due

I was desperate. It was the fourth time in the past six months I was late with rent. When I told my landlord he just looked at me. He told me he would give me one more week to come up with the money if I sucked his cock. I quickly refused and he just laughed. “Fine”, he said. “Rent in full by this evening or the eviction notice will be on your door in the morning.”
I gave in immediately, really had no choice. I started to get on my knees and he laughed again. “Oh no, Princess” he chuckled, “I want you all dressed up and pretty.” I blushed. When he had come to do some repairs a few weeks earli... Continue»
Posted by keripinkpanty 10 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Miss Allison goes gardening

Miss Allison goes gardening
I was in the kitchen having my morning coffee I was wearing my micro shorts really show of my big ass and had my low cut tight tshirt no bra my huge tits and thick nipples tight against the fabric and my tennis trainers I was going to do some work in the greenhouse and old bill from next door was going to give me a hand
As I finished my coffee there was a knock on the back door it was old bill morning miss Allison morning bill you ready yes bill he was just wearing a pair of shorts and trainers he said it was going to be hot today as we went into the greenhouse I... Continue»
Posted by allison1969 12 days ago  |  Categories: Shemales  |  
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Aunt Jenny's Perverted Futa-Cock


Sex has always been a taboo topic in my f****y. My Mom, Judy, was strict about enforcing a 'No Pornography' ban in the house, and on the rare (but still far too often) occasions that she caught me masturbating...She never told me not to, but the tone was clear: she disapproved.

My Aunt Jenny, on the other hand, was (and is) the opposite of my Mom. She loved sex and didn't care who knew it. My friends even found a few old pornos that featured her on the internet and made copies for me. (My Mom had inst... Continue»
Posted by Batman_112 1 month ago  |  Categories: Taboo, 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 3 years ago  |  Categories: Masturbation, Shemales, Taboo  |  
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Home.

I now live in a cute, one bedroom house outside of Atlanta. My boyfriend, Daniel, owns it and invited me to live with him. We have dated for a couple of months and we have become close. We almost have not stopped having sex since we moved in. I am a little bit of a slut (or so I like to think) and he is always wanting to try something new.

After a few days things have gotten a bit normal. I heard his alarm, when he stopped it, he rolled over and wrapped his arm around me. I could feel his breath by my ear. I turned my head to him, he caught my lips quickly. Enjoying that kind of early morni... Continue»
Posted by bisubtaylor92 9 months ago  |  Categories: Anal, Gay Male, 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 2 years ago  |  Categories: Anal, 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 1 year 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 2 years ago  |  Categories: Anal, First Time, Shemales  |  
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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 2 years ago  |  Categories: BDSM, Fetish, 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 2 years ago  |  Categories: 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 2 years ago  |  Categories: BDSM, First Time, Shemales  |  
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Birthday

It was supposed to be the best day of my life...and maybe it was, but
definitely not in the way I planned.

My 21st birthday...my first day as a man, as a true lord of the Manor...my
first day as a Master. I was so nervous I threw up my lunch. Not very
manly, I know, but just the thought of having my very own sissy to play
with had me teetering between the giddy excitement of a k** right about to
open the biggest present under the tree, and the stark terror of officially
being a man in my step-father's eyes...how could I measure up to him? I
felt destined to disappoint him...and I did... Continue»
Posted by klammer 3 months ago  |  Categories: BDSM, Gay Male, Shemales  |  
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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 2 years ago  |  Categories: Taboo, 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 2 years ago  |  Categories: Shemales, Taboo  |  
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Making of

THE MAKING OF JANE

Jason H. was a small boy who had suffered from heart problems as a
c***d and had not been permitted to play the "rough games" other boys
his age played. At age 11 he was finally given a clean bill of health
and allowed to be a normal boy, but he was shunned by the other boys
because he didn't know how to play football or baseball or basketball
or any other active sports. Whenever, the other boys had to pick
teams, Jason was always the last one picked due to his lack of skill
and small size. This hurt him greatly, and he always avoided being
put in the position... Continue»
Posted by klammer 7 months ago  |  Categories: Gay Male, Shemales  |  
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Back to School

Back To School
Nikkie Silk

I was so excited. This was going to be the first day at my new job. I had recently been appointed as the receptionist and administrative assistant at the local Elementary School. I set the alarm to wake me up early, so that I could get ready and make sure I would be on time. I was excited but also nervous. I had yet to meet my new boss, Mr Michaels, the Principal of the school. I had been hired by his deputy, so I would be meeting him for the first time today.

The State had just enacted an affirmative LGBT action hiring program. This meant that as a pre-op tr... Continue»
Posted by nikkiesilk 8 months ago  |  Categories: Anal, Shemales  |  
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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 2 years ago  |  Categories: 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 1 year 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 pleasurenfun 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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Summer transformation Part 1

My jaw hit the floor as I read the first email I ever received from John. My mind twisted, heart raised, and my pussy pulsed repeatedly.

A week earlier I had posted an ad on craigslist... One of those late night d***ken fantasy ads where you spill your darkest desires, wake up the next morning and think "wow... I really am a pervert!" My ad was placed M4M, M4MM, M4MW, and T4M. I wrote:

" 18 year old looking to experiment. 5'5", 170, naturally smooth. School is out so I have lots of free time, super horny all the time, looking to learn. Discretion is a must, can`t host, love mature ... Continue»
Posted by archerfan88 7 months ago  |  Categories: First Time, Shemales, Taboo  |  
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