MY FIRST TRANSEXUAL EXPERIENCE
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 **********”.
“Gimme that fucking pussy you **********”
“I’m gonna pump your little fuzzy twat full of hot cum”.
“I’m gonna fuck you all night long **********”
“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 ******* 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.
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 **********”.
“Gimme that fucking pussy you **********”
“I’m gonna pump your little fuzzy twat full of hot cum”.
“I’m gonna fuck you all night long **********”
“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 ******* 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.
8年前
