Shemales Porn Stories
Page 5

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 4 months ago  |  Categories: BDSM, Gay Male, Shemales  |  
8517
  |  
40%
  |  1

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 2 years ago  |  Categories: Anal, Masturbation, Shemales  |  
8461
  |  
100%
  |  7

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 1 month ago  |  Categories: Shemales  |  
8447
  |  
60%
  |  2

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  |  
8423
  |  
100%
  |  8

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 11 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
8322
  |  
89%
  |  7

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 2 months ago  |  Categories: Taboo, Shemales  |  
8102
  |  
93%
  |  5

My 1st experience with a "Special Girl".

Let me tell you something about myself. I'm your average Hispanic male. I can honestly say I'm not gay or attracted to men. In contrary, I'll truly get turned off by that scene. Im also turned off by hair/hairy skin and bad hygiene (who isn't... LoL). It's just not for me. Yet something about a cute shemale with a booty is something i cant resist. I found myself enjoying shemale porn. A cutie with a booty takibg it up her booty hole. My favorite scenes involve a passable tranny (Ts Foxxy, Sianna Grace, Ts Celeste, etc.) Wrapping her ass cheeks around a dick. Skip the scenes were shes getting a... Continue»
Posted by socal805 15 days ago  |  Categories: First Time, Shemales, Taboo  |  
8101
  |  
91%
  |  3

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  |  
8086
  |  
97%
  |  13

True story of an old man in the woods

I was just a young lad the first time i did any thing with another guy, i was still living with mom in the house she inherited from her father after he died in a small village that mainly had elderly people living in it.
There certainly wasn't any one my age about so contact with other youth's was limited to school.
Most of my time was spent playing alone or helping mom about the house, then some thing happened that was to change me for ever.
It was a Sunday morning and mom was home doing some house work, i was watching cartoons on the TV when she called to me to help her get the washing in... Continue»
Posted by fun_boy_fan 1 year ago  |  Categories: Gay Male, Mature, Shemales  |  
8059
  |  
99%
  |  13

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 11 months ago  |  Categories: Anal, Gay Male, Shemales  |  
8036
  |  
96%
  |  6

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  |  
8013
  |  
89%
  |  1

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 2 years ago  |  Categories: First Time, Shemales, Taboo  |  
7992
  |  
97%
  |  11

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  |  
7975
  |  
98%
  |  6

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  |  
7957
  |  
82%
  |  6

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 8 months ago  |  Categories: Gay Male, Shemales  |  
7944
  |  
91%
  |  2

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  |  
7914
  |  
95%
  |  4

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  |  
7906
  |  
84%
  |  9

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  |  
7886
  |  
96%
  |  8

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 9 months ago  |  Categories: Anal, Shemales  |  
7740
  |  
95%
  |  17

Scary!!!! my friend's mom has a dick!!!!

It happened last Sunday when I visited my new neighborhood Jack's house... They have arrived in the city a week ago from that day... Jack and his Mom(Aunt May). As we came to know aunty may was a single mother. She was a woman of 40-45 years with heavy tits and pale white skin. She looks like a perfect milf. Me and Jack has just completed our school so we were planning for some camping, hiking and mountain climbing. When I visited his house last Sunday then I came to know that Jack slipped from the stairs last night which cost him a fracture in his right leg. That was really surprising for us... Continue»
Posted by hunter043 19 days ago  |  Categories: Anal, First Time, Shemales  |  
7698
  |  
74%
  |  2