Shemales Porn Stories
Page 14

SHEMALE SURPRISE #3

i have just fulfilled one of my fantasies with the help of niki, who used to
be nicolas a male cousin of mine who is now living life as a shemale. i have
just swallowed a river of cum after sucking on my very first cock. being male
i have never thought of myself as being gay, and i still don't as i am not attractive to males at all. i love being hetero, but i do have an attraction for crossers or shemales.
my cousin niki and i were having our first tryst and after making niki cum
in my mouth she still retained her erection, prompting me to ask if would mind
fulfilling another fantas... Continue»
Posted by qrystofer 11 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 3274  |  
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My first time with a BBW Shemale turned into a thr

I was at the club on a saturday night and didn't really expect anything different to happen that night oh boy was I wrong, happily wrong. I was sittin at the bar gettin d***k as hell and this voice from behind me and says " hey big daddy can I sit with u ? " I look up and I see this fine, phat, thick, lightskinned woman lookin right at me. Me bein' a BBW lover and partial to light skinned black women she was a wet dream cum true.

I said sure u can sit here baby if u tell me your name. She says " my name is passion, whats yours daddy ? I told her and we start to chat about things we like an... Continue»
Posted by Champdick 1 year ago  |  Categories: Shemales  |  Views: 3268  |  
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Once upon a time, I dated a Co-Worker...

It was summer and Dad had asked me to help him around his car insurance agency. Mainly I answered phones and typed in reports on the computer. Couple of nights a week, I would also vacuum, clean up and straighten the office a bit. Had the weekends left to go to the beach and hang out with my friends. Robert and Mayra still worked there, they had been with Dad for years. Both were appraisers, and were in and out of the office constantly. There was a new part-time clerk. Her name was Natalie, in her mid-twenties, a tall girl with long brown hair and hazel eyes. Chatty and friendly, I felt... Continue»
Posted by latinCharm 1 year ago  |  Categories: Anal, Shemales  |  Views: 3254  |  
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Slut bi cross dresser

Party Surprise - First sex as a Crossdresser.
This is a work of Fantasy. I hope you enjoy.

Stephanie and I had been married a few years and enjoyed a reasonable sex life. She knew of my dressing and although she didn’t approve she indulged me now and then and we had sex when I was dressed or with me wearing lingerie. I think secretly she was jealous of my legs. She was a petite sexy woman and we were almost the same size but I still had my own stuff that I’d secretly obtained from eBay and op shops.

I didn’t consider myself bisexual, certainly bi curious at least. I liked watching guys ... Continue»
Posted by pesty 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 3252  |  
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A night out with my s****r

Following in from Shopping with my s****r - Please read my other stories first to set the scene.

Jane and I lie embracing on her bed, our naked bodies merging into one as we hold each other closely.

"What do you want to do tonight?" I ask

"I was thinking we could have a night out together, maybe a meal and a few drinks, see where the night takes us!" Jane replied.

"That sounds good to me, I haven't been out for a few weeks because of my exams."

"Well, I'll treat you to a nice meal and a bottle of wine on one condition" Jane offered with a devious smile on her face.

"Go on,"... Continue»
Posted by ukdan78 3 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 3244  |  
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Airconditioner repairman laid some pipe

I was literally bored to death when my mom went on a vacation, i was hoping that i was gonna enjoy freedom when mom's away but things got worse as i found out the air-conditioner wasn't cooling the house, it was the dog days of summer and i really hate this muggy, hot weather. So i gave a call to the place where we bought it and asked them if they could send someone to fix it. Like i said, the weather was terribly hot, therefore i was wearing a micro-mini short which was showing of my curves in a very revealing way. It was almost 4.00 pm when the doorbell rang. I was expecting the same guy... Continue»
Posted by Slave4str8twinks 8 months ago  |  Categories: First Time, Hardcore, Shemales  |  Views: 3238  |  
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a big suprise

Yesterday i came home from work telling my wife i have to make a few phonecalls and she should get in the shower and remove hair from her Body. I mentioned to clean all holes properly and make sure you dont take too Long.
I called 2 couples and two freinds, one of them male and a female that i use as a Sub every now and than. She has been tought by her ex husband to do all that been told with no Limits. i met her when she needed a mechanic to fix her car, we didn´t only take care of the car but that´s a different Story. We all agreed to meet up in 1 hour at our house, we live in the Country ... Continue»
Posted by hotdutch 1 month ago  |  Categories: Fetish, Group Sex, Shemales  |  Views: 3237  |  
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The Next Morning

I hadn't planned on getting d***k last night but what can I say? The mood was just right for it, me and Nicole are c***dhood friends and although we've branched out and built our own lives and become two very different people, we still find a way to make our friendship last throughout the years, you could say that she's my best friend, I've been there for her and she's been there for me and people like that seem rare to come-by these days so it's safe to say she means allot to me though clearly I meant much more to her because here was, waking up in her bed next to her the following morning.
... Continue»
Posted by RunandCummer 8 months ago  |  Categories: Fetish, First Time, Shemales  |  Views: 3229  |  
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Four Guys And A Shemale

My big br0ther enjoyed humiliating me when I was young.
There was this guy in school that picked on me all the
time, calling me "tits" and groping me in the hallways.
I couldn't complain because I was a known freak and
slut so I just tried to avoid him and his asshole
buddies. I was terrified of Donald and his three friends.
One Saturday morning when m0m was visiting grandma I
showered, blow dried and came down the stairs naked
because that was one of my b*****r Johnny's rules:
whenever m0m wasn't home I had to go naked or put on sheer
black stay-up nylons if he told me so that he
... Continue»
Posted by yutubeslut 1 month ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 3229  |  
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Weekend retreat

When I go to work, I am in 'boy' mode. I certainly am not the most masculine person, and I am pretty certain that everyone knows my sexual preference. I often get mistaken for a woman even when in 'boy' mode. Whatever. I am who I am... deal with it :)

A few years ago my former workplace had a nice mountain retreat weekend. I love these retreats, not because I become closer to those I work with, but because they are so peaceful.

I arrived at the lodge on a Friday night and spent the next day communing with nature. My fellow workers were doing other activities, and I spent most of my t... Continue»
Posted by zaria_ts 10 months ago  |  Categories: Anal, Shemales  |  Views: 3226  |  
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The Tgril Hooker pt2

All my stories are based on real life experiences.

As I left off.....

Emma pulled the toy out of me and said "I want you on all fours and ready yourself for a extra surprise...."

I was still blind folded and as horny as hell, Emma had so far made me feel amazing and I think due to being blindfolded it had almost given me double the pleasure and the darkness had added an extra thrill of never really knowing what was going on.

I got on to all fours like instructed and I could feel Emma behind me. Her cock was thick and long, maybe the thickest I had ever had and now I could feel it ... Continue»
Posted by dirtydisco99 24 days ago  |  Categories: Anal, BDSM, Shemales  |  Views: 3218  |  
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1st time with an angry Trannsexual

This is a true story that took place in bayswater London in June 2012.

I had often wondered what it would be like to have sex with a hot transexual girl. Finally with the help of the Adulwork website i was able to find some stunning TS girls available for meets in London. I chose a hot blonde brazilian beauty named Isabella. She looked amazing in her pics and her cock looked gorgeous. I had to meet her.

I emailed her, she gave me a number, and i called to arrange a suitable time to visit her.
I knocked on the apartment door and awaited a response. Moments later the door crept open and ... Continue»
Posted by kentcariblad 9 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 3211  |  
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My shemale boss part 2

Friday 12pm was here, I nervously knocked at my bosses door part excitement part apprehension ran through my body.

A clear come in could be heard from within by my boss Miss Jones so I went in. Ahh Rob right on time, take a seat and I'll be with you in a minute, she said.

I sat down opposite her desk whilst she continued to study her paperwork. Her black rimmed glasses were on the tip of her nose and with her finger, she curled her long black shoulder length hair. Through her glass desk I could see her tight black leather trousers she had on and black 5" heals. She had walked through my... Continue»
Posted by big_rob49 1 year ago  |  Categories: Shemales  |  Views: 3205  |  
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A Trannie takes her first big black cock

Sitting on the lounge at my local sex club I was watching the guys go by. You get to notice certain guys going past trying not to look like they are checking you out on the sly (and vice versa) thinking how they can approach me.

Normally it’s just the usual crowd of guys but several weeks ago a big heavy set African guy in his mid 30’s kept going past me and looking at me out of the corner of his eye. After about his third walk past I gave him little smile. When I could see him coming down the hall the next time I got up and slowly walked around the corner into the next hallway so he could... Continue»
Posted by toniparr 3 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 3197  |  
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Helping a friend

Anna has been working in my office for a year now. I have never heard her talk about a boy or girl firend. Anna is 5'7'', long legs, light brown hair almost to her waist, very pretty. I have always talked to her, had lunch, but she had never opened up until she needed some help.....

Anna had bought a house that needed work. A couple of months after she bought it, she was complaining that her sink leaked. I told her i had done odd jobs through out my life and i would be more than happy to check it before she called a plumbler. She told me to come over friday after work.

Friday came,... Continue»
Posted by edukateme 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 3192  |  
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I Disco

By - Tex Lee

I Disco

I discovered crossdressing in my early teens when I was once
using the bathroom I noticed my mothers red lipstick on the
bathroom counter. I opened the tube out of curiosity and
twisted out the red phallic looking lipstick and felt
compelled to put it on. I felt a strange and exciting sexual
arousal that I never felt before and soon was wearing
lipstick and masturbating every chance I got. Eventually I
started wearing my mom's and s****r's panties and bra, then
dresses, skirts and high heels. By the time I was 16 I
accumulated a nice little wardrobe of sexy... Continue»
Posted by jayymie 2 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 3188  |  
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Four in four hours - am I a whore? (Part 2)

So, I'd had my passing quick bj and the guy I blew has already sent me a message thanking me for what I did for him and asking me when I'm available again, perfect !!

From the quickie it took me a while to get to the hotel, called when I was in the car park, heels on and walked across the car park with more delicious feelings between my legs, I adore walking in heels and stockings, they're always so sexy. There was a couple going into another room and the guy did a double take and smiled, murmered a 'bonsoir' before he went into the room, I think I scrub up pretty well.

It was a budget ... Continue»
Posted by antoniaf 9 months ago  |  Categories: Group Sex, Mature, Shemales  |  Views: 3186  |  
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A little fantasy...

This is a work of fiction. It's a small window into a huge world of fantasy for me. Enjoy!

It was a wonderful day. Kristy had just moved into a new town and settled into a new job as an accountant for a local practice specializing in debt recovery and settlement. Kristy had spent the last 2 years in school and had finished to start life a new and on her own. She grew up under the yoke of her mother and older s****r. Kristy wasn't like other girls as Kristy was really born a male. At an early age Kristy displayed signs of being very feminine and showing interest in very feminine things. She ... Continue»
Posted by russianrabies 4 months ago  |  Categories: BDSM, Gay Male, Shemales  |  Views: 3183  |  
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The Studio and the Shemale

When the company I worked decided to relocate to the north of England, it was made clear to me that there would not be a job for me there and so the decision whether to move woth or leave was decided for me. The redundancypayment was extremely generous, as it should be, I had been with them since I left school. So now I had to find a new job and the decision was whether to stay in the line I was in or change careers, but With the redundancy payment as it was there was no rush.
Quite by chance I discovered that a photographic studio, which was literally a 5 minute walk away was looking for an ... Continue»
Posted by dasilva1672 3 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 3178  |  
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A Little Twist at My Last Massage ...... By BigSof

I have a really bad back from an auto injury several years ago and have been getting massages to relieve some of the discomfort I have. The problem with that is I, like so many people with injuries, have an addiction. I’m not talking about pain killers… I am now addicted to massages! Now I know some of you are laughing thinking I am trying to 'be cute', but I am telling you, I could get a massage right now and 1 hour later if given the chance I’d do it again, and again, etc. The overall feeling of serenity and calmness you feel is my addiction. Of course any time you get a ... Continue»
Posted by bigsoftee 2 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 3169  |  
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