MY FIRST TRANSEXUAL EXPERIENCE free porn video

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Let me start out by saying that I haven’t written in a while. I’ve had plenty of sex, but not many experiences worth sharing. I felt it necessary to share this one because this was my first “trans” experience.

I’m not gay.

This short story is about my coworker who I’m going to name “SEAN” for the purpose of this story. The person’s real name is obviously not Sean, but I don’t want to give away any real identities.

Basically SEAN is a transsexual.

I know we call transsexual men who change to women a myriad of names, but I don’t know what we call FEMALES WHO TRANSITION TO MALE. Sean had his/her breasts removed and had not yet had the operation to add a penis. SEAN worked with me for 3 years and I’m writing about the first time we had a sexual encounter – prior to my own marriage. We’ve had several, but the first was best. Though Sean would pass as a man (easily), I can’t bring myself to call Sean a male pronoun or a female pronoun after “knowing” Sean physically.

When I first met Sean, I believed Sean was a male, but there was always something odd about him/her. Skin was very soft. Neck was smooth – no Adam’s apple. Voice was very high pitched. Physically built small – not intimidating (at all) and was very active in the company’s Gay/Straight Union which is basically a way of ensuring a SEXUAL HARRASSMENT FREE ENVIRONMENT to save them from lawsuits.

When I first found out Sean was a Transexual, I was surprised, but not terribly shocked because I always suspected something wasn’t “right” with him.

Over time, I developed a sexual attraction to Sean. I’d notice Sean’s nipples stiffening in the cold A/C office and couldn’t help staring. I’d secretly savor hand shakes and physical contact more because of how “odd” it felt. I did let Sean know I thought he was “interesting”. We were very friendly with each other. We grew close. Sean knew I wasn’t gay, but also knew that I had some fascination with him.

I paid very close attention to and studied Sean who eventually started to adopt “feminine” behaviors around the office such as painting his nails and wearing a “man purse”.

At first I kinda felt disgusted and guilty about having feelings of desire for a transsexual, but eventually I made a move on it.


Sean, a few others and I had to fly out of town to Denver so we could attend a conference and we each got to partner up for a two bedroom suite.

Without belaboring the boring parts, I’ll just skip to the part where Sean and I had sex.

After a meeting in the convention center we retired to the hotel room.
We had just finished sharing a shower and we mutually cleaned each other with the soap and washcloths. Sean’s body was like that of a teenaged blonde – only minus the breasts. Sean allowed the public hair to grow to hide his own perceived shortcomings until he could afford to have a penile implant. I was essentially about to fuck a female who looked slightly ambiguous. (Imagine: Rachel Maddow with facial hair stubble)





I reached around Sean’s chest with my right arm – squeezing and toying with what remained of the breast – twiddling the nipple with my fingers. With my other hand I pulled down his/her pants to get access to his/her vagina. What awaited me was a hairy, unkept snatch…just the way I liked it.

Up till this point my penis was stiff, resting on Sean’s lower back, with obvious intent.

Sean didn’t fight me back as I positioned my penis head at the entrance of his/her hairy cunt lips. I have a long, thick circumcised penis. It already had a small amount of precum at the tip. It was hard, tightening the skin around my balls, throbbing and at this point, “demanding” to get inside Sean.

I slowly pushed inside. I enjoyed the tickling of the cunt hairs.

Sean moaned deeply, prompting me to start licking sucking on his/her neck.

My penis took on a mind of it’s own and started pumping deep and hard. I felt like I could cum almost immediately. It felt as if the sperm was fighting to get out and into him/her.

Sean still had female hips, although not much development. My hands alternated between different parts of Sean’s body as I penetrated him, but gravitated to his inner thighs so I could play with his swollen clit.

My pumping was so deep that Sean could barely take it . Not exactly fighting me back, but definitely trying to slow the rhythmic pumping motion, while trying to control the position of my entrance angle and squeezing my wrists – begging me to slow down. Sean’s eyes were closed, his/her back to me and I had her/him tightly in my grasp. I pumped harder, faster and deeper. That hairy cunt was squeezing my penis and rubbing it almost as tight as a fist.

I changed my grip on Sean to pull him tighter into my embrace. I pushed even deeper. Sean let out a few cuss words: “uuuuuuuuummmmmm"....."o shit”…”O fuck”… and some whimpering, but I didn’t let up.

the more she/he whimpered, the more vicious I thrusted. The harder I squeezed. I held his neck tightly like a tiger grasping a deer's neck.

And then there was my humiliating dirty talk into his ear.

“I’m gonna show you what being a man feels like”

“I’m gonna fuck you real good little boy”.

“Gimme that fucking pussy you little boy”

“I’m gonna pump your little fuzzy twat full of hot cum”.

“I’m gonna fuck you all night long little boy”

“You’re my little twink now”.

I pumped Sean so deep I could have impaled him.
He seemed to enjoy my sado masochistic comments and my punishment of his vagina.
Part of me wanted to make him feel powerless.

After a good number of deep thrusts, that tight pussy of Sean’s finally managed to take me for all it was worth. It squeezed the cumshot right up the girth of my pole and finally coaxed it out. I grunted and groaned in Sean’s ear as she breathed heavily and reached down to grab the head of my penis. The final few thrusts of ejaculation spurted enough semen into Sean to leave his underwear, pussy hair and the hotel shower wall stained with my DNA. “I’m gonna cum in your tight little twat little bitch”.

I partially creampied Sean, but he managed to pull me out and jerk the head of my cock while I was still spurting and cum kept shooting out in hot globs. I told Sean to get down and suck the rest. Sean didn’t even hesitate and was able to swallow the last few pulses.

Because of the hormones Sean takes, pregnancy wasn’t an issue. Her vagina is swollen and doesn't have regular periods.

I enjoyed working my cock into Sean nightly without condoms – completely un-afraid of an accidental impregnation. Part of me was a big disappointed I couldn’t impregnate him.

For the next couple days, we stayed at the convention center, I fucked Sean a few more times. I was never serious about Sean as a partner…only that the very thought of being in his tight punnany made me lose focus whenever the thought entered my mind.

Sean specifically wanted to live the life of a “man” and wasn’t interested in a male partner despite having let me fuck him. We remained fuck buddies for a while till Sean moved on to another firm.

I’m writing this specifically because recently I saw Sean at a professional development in Newark and when I saw him, I gave him a handshake and a secret groping about the buttocks. Still hasn’t afforded the penis implantation surgery. I was able to get him alone in the men’s bathroom where I gave him a deep tongue kiss.

The affection still exists between us, but I’m no longer able to simply have sex with him now that I’m married.

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I had been having fantasies for a few years before I decided to make it happen. I decided to create a profile on a men only site to see what was out there. Over a three month period I would check out profiles that fit what I was looking for. I wasn’t into anyone looking for a quick hook up. I was clean, healthy and curious and wanted to stay that way. I imagined that there had to be others like me looking for the same things. There was a lot that I had imagined over the years. Little did I know...

3 years ago
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Learning By Experience

Learning By Experience is a work of fiction. All situations and characters are fictional. Any similarity to persons living or dead is purely coincidental. It is a copyrighted work by Caitlin Rose. It may be archived at any site that does not charge a fee for access. Please obtain permission from the author before archiving. All other rights are reserved. This work contains descriptions of crossdressing and some mild sexual situations. If you think you might be offended, go...

4 years ago
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Light of Experience

Experience 1 It was a dark and miserable evening as she returned from work. The bus had not turned up and now she was having to walk home in the rain. She gave a sigh of relief as she inserted the key in the lock and opened the door. After turning on the lights and putting the fire on full blast, she went into the kitchen, poured herself a stiff drink and then settled down into her favourite chair before she flicked through the channels on the box. Her mind wandered through the events of...

4 years ago
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First Swapping Experience

I was very recently married when this evening took place and whilst that may be shocking to consider for some, we had such an enthusiastic and adventurous sex life with each other that, with hindsight, the events of this evening seemed to be a natural extension, I say with hindsight as the whole experience was arranged as a surprise by my wife....Annie is petite and dark haired with cascading brunette curls falling just beyond shoulder length, she has hazel eyes and a beautiful body with curves...

2 years ago
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First Dark room experience

I was in the army and on leave at the time and had gone on holiday with a couple of straight mates to Gran Canaria, to Playa del Ingles. the idea was we share a hotel room and spend our day's on the beach and nights drinking in the bars, which we did. But during the late evening of my third night there I "Got split up from my friends" I actually slipped away from them as I had had enough of looking at women!!I had found out where the gay bars were and went off exploring on my own. I checked out...

4 years ago
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Young girl extreme winter nudity experience

Introduction: Story about brave girl winter walk At first I have to start with me, that this project requires to give also self-experience. I have practiced winter nudity many years, but not regularly. There have been some pauses. I have been lucky to share winter nude walk with some girls, like here: http://www.nudeimagehost.com/viewer.php?file=56243058045088081241.jpg These are my photos and my car can be seen in two photos of these series. In previous winter I began from 1st January and then...

3 years ago
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First true cuckold experience

This is the true story of the first girl who really cheated on me.I had experiences before this. I highly recommend reading my first story posted on my profile.You'll have a lot more information, and will be able to get a better understanding of, where I am coming from.This is the first time a was a true cuckold.It was about 5 or 6 months after my experience with Celina, I had moved on a little but not really.I was still hanging out and skating with Colton and Christian(Who is Celina's little...

2 years ago
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Bus Journeythe longer experience

Hello every one this is Someour Mukh again sharing my experience with you all…if u reading my story first time then I must tell you that my height is 5ft 11in having a athletic body due to my martial arts training …and doing my engineering from Pune.as if I told you in my earlier story(if u have read that… Titled Bus Journey-the short fantasy) that I hope to meet that women again…whom gave me the first immense pleasure of touching the boob(or rather not say it first.. That’s a secret).I thought...

1 year ago
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Bus Journey the longer experience

Hello every one this is Someour Mukh again sharing my experience with you all... if u reading my story first time then I must tell you that my height is 5ft 11in having a athletic body due to my martial arts training ...and doing my engineering from Pune. as if I told you in my earlier story(if u have read that... titled Bus Journey-the short fantasy) that I hope to meet that women again...whom gave me the first immense pleasure of touching the boob(or rather not say it first.. that’s a...

Erotic Fiction
4 years ago
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First Experience Is The Best Experience

Hi, I am Sharath from heritage city mysuru, karnataka..This is little bit long story sorry for that.. Friends my name is sharath 26 yrs old.. I think there is no need about my body details since none of you guys are interested. The heroin of this story is my girlfriend sandya.. Friends when I was doing my final year engineering I felt very lonely since my most of friends are engaged and they were are all busy with them. So I thought to find the gf for me.. I opened the nimbuzz account in that I...

3 years ago
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Young girl extreme winter nudity experience

In previous winter I began from 1st January and then every weekend, but not only the coldest (4-5 Feb), from which I wrote main story later. Longest time was at 26th February 1 h 47 min and temperature in this day about -4-5 (23-25 F), but sunny. Feeling of cold is not the same every time. Generally it can be very different. But normally after some 30-40 minutes is the warmest moment, then you don’t feel any cold. After some 1 h – 1h 15 min body started to feel colder again, but not too much....

3 years ago
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My First Incest Experience

Hey, friends, I am back with a new indian sex experience. Thank you very much for liking my previous story “The dream-Swapna”. There are a lot more experiences in my office which I want to share with all the readers and as the characters are somehow related to each other, I will be narrating them as part of a Sex Saga starting from August 2015 till now. I thought of publishing my older works first. However, recently I have fulfilled two of my darkest fantasies. Hence, I do not want to waste...

Incest
3 years ago
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Laxmi Aunty Taught Life 8211 My First Experience

Hi frnds this is Kumar from Hyderabad working in an MNC. I am a big fan of ISS. I have been reading this ISS from last 2yrs. This is a true incident and my first story on ISS, so please comment on it and give feedback and mail me your experiences. Let me introduce myself. I am 25yrs old 5′ 7” tall and have a good gym physic and a good cock to satisfy anyone. This was happened in my age of 18 with my aunty Laxmi. She is well shaped lady with gud structure and massive boobs, little short in size...

Incest
2 years ago
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First Masturbation experience

I haven't found many stories like this (or maybe I just haven't looked hard enough) so I thought I'd do this.So this is a true story. Like true-true, or true to the best of my ability, none of that nonsense where people say it's true but more like "loosely based on a true story". Just thought I'd get that out there.Anyways, when I was much younger I had no idea how sex operated. I didn't even know what girls had down there for a good bit. I didn't know semen even existed. I had a very limited...

3 years ago
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First time experience

It was 1978; I was 18 years old at the time and was hitchhiking along a highway in upper Michigan in the middle of winter, late at night. A car stopped to pick me up after a few minutes of walking in the cold and I was grateful for the ride. I jumped in and thanked him for stopping, telling him I was headed for the cabins up the road a few miles. He was probably ten years older than me and we engaged in casual conversation as if we'd known each other for ages. After a few minutes we came upon a...

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