It was time to try a tranny (real story no bull)
Yesterday I thought I was straight....ish!
I've only ever been with women and for years it was only ever women that I desired and intended to be with. That all changed when I went to college. I met someone I thought was a girl randomly waiting in a queue in the cafeteria. Her name was Naomi. She was quite tall, around 5"10 but was very slim and had incredible feminine hip structure. Because she was slim she didn't need breasts to seem like a convincing girl. She was very beautiful too with pale skin that showed she didn't like the sun much and a few evenly patterned freckles on her nose that added to her cuteness. I fancied her as soon as I saw turn around and look at me in the queue, she then turned and whispered to her friend about me it seemed which gave me confidence to speak to her. I got my signal to speak to her when she picked up a yoghurt whilst waiting and dropped it. I said jokingly I hope that wasn't the last one, I was going to pick one up myself and she laughed, a deeper noise than I expected to hear but a pleasant and attractive one nonetheless. I saw an opportunity to maybe get her number so decided to try and flirt a little. I mentioned her teeth were very white and that she had a nice smile, she joked that it must be all the yoghurt she eats and I chuckled and agreed. The queue became small very quickly and I didnt find the confidence to ask for her number before she had been served and left.
As I was served and left I saw her sitting with her friend near the entrance and near some friends of mine. I took the opportunity to sit near her hoping I would find the balls to ask for her digits. I did in the end only after my friends had left though! I approached cautiously and asked if she minded me sitting with her and her friend, they said yeah sure. Introductions out of the way and now actually being straight up face to face with this chick I notice she has too sharp a bone structure in her face and her voice is feminine but deep and seems strained as if she is struggling to keep her voice steady. I asked if the girls were dating concentrating my question by staring at namoi. But they were abit taken back by my question. The brunette friend who wasn't bad looking responded sharply, "I have but she hasn't" to which the beautiful pale skinned babe naomi scowled at her friend visciously.
I got the impression she didnt like me from that and said, "you dont look happy she just told me your available" and she replied, "no its not that its complicated". I said "a boy, she said no". I said "is it coz you like girls or something she said no and before she could say another word her friend said just tell him he seems like a nice guy. To which my earlier suspicions were raised even more, I asked are you a boy or something and she said yeah really quickly and left. I followed in disbelief that I was actually following but still my legs carried me after as she made her quick escape. I stopped her soon enough and asked why she ran she just looked down. I said i really think she is cute and at that very point I see my friend come out of one of the buildings near by. My heart suddenly sinks and I think what if people knew I liked a transgender boy I would be slated for the rest of my college life so without saying another word I pull my hood up and shout my friend leaving naomi confused as to why I did that.
I have regretted that decision so much since it happened. As college sucked anyway and I didnt see her or her friend after that. There were over 2000 people on that campus its no real surprise. Anyway. What that experience did do is opened my eyes to the fact some men who dress like women look damn good doing it lol. While browsing porn some time after I felt a sudden urge to click a link with a pretty t-girl and the rest is history. I have explored many different porn sites and have begun to become hooked on shemales. So much so, it got to the point where I needed to find out if I actually would do stuff with one.
I contacted a local t-girl who was in town for the week. I was so nervous just speaking to her on the phone let alone the drive there. I stop and call her to tell her im outside. the butterflies were too much at this point so I light a cigarette. She tells me where to go and gives me the code to her apartment block. I finish my fag enter the building and head up to her room. Im greeted by a latin beauty with small slim body no taller than 5"7. Her face is nice, quite feminine which is why I chose her. The lights are dimmed and she shows me into the bedroom and starts by taking off her jeans, asking me if I came from far. I stuttered and mumbled no not far and she sensed I was scared. I stood against the wall fully clothed just staring at the wall and she called me over saying dont be scared and sat down next to her on the bed.
She rubbed my leg and leaned in to kiss me, we kissed for a few moments before she felt for my cock and pulled it out of my jeans. she started sucking it while I watched her panties bulge as her piece started to grow as she sucked me. I asked her to take her panties off becoming less nervous all the time because she was so welcoming. Her cock was at least 8 or 9 inches long, it was thick but not too thick and it stood up hard as a rock without me yet touching it. She was a brazilian tranny with light skin and a bright pink cock head a very beautiful dick by anyone's estimation. I took a knee knowing this my test was coming. So far I had enjoyed my time with her but would I actually enjoy sucking her cock. I approached slowly meeting her eyes with mine as my lips pressed against her cock head. I started by flicking her balls with my tongue and working my way up her thick shaft. I got a whiff of her musky sweaty cock as I teased its shaft with my tongue. I then moved to her dickhead which smelled amazing as I rubbed it across my nose and became lost in her sweet scents. I then without hesitation stuck her fat cock in my mouth. I sucked slowly and felt even more turned on as she moaned a few times as her cock hit the back of my throat. I wanted to fuck her now so she asked if I wanted to do doggy or missionary, I said doggy and we got into position after she had put a condom on me with her mouth. I entered her little hole slowly and fucked her hard for at least 20 minutes. I told her I was going to cum and she said okay she will cum too. I then asked if she could cum in my mouth, she started by fucking my mouth with her fat dick and letting me lick and suck her swollen glans which looked like a strawberry lollipop it was so pink and juicy. she then pumped her cock hard while I sucked her balls and before she cum she let out a big moan and gave me 5 thick shots of her healthy sperm in my mouth and on my lips and chin. I had never tasted cum before this was a first, it was so salty and thick it almost made me hurl at first but then the saltiness made me even more horny as I jerked my dick and seeing her shiver and gasp for breath while I sucked the last drops of potent cum from her cock took me over the edge. It is official. I love trannies and that will definitely not be my last time seeing one. Heck after that I would marry one!
This was my first experience and first time writing a story like this so be kind and I hope you guys liked it
Re: It was time to try a tranny (real story no bull)
Quote:
Originally Posted by
Stubee94
Yesterday I thought I was straight....ish!
I've only ever been with women and for years it was only ever women that I desired and intended to be with. That all changed when I went to college. I met someone I thought was a girl randomly waiting in a queue in the cafeteria. Her name was Naomi. She was quite tall, around 5"10 but was very slim and had incredible feminine hip structure. Because she was slim she didn't need breasts to seem like a convincing girl. She was very beautiful too with pale skin that showed she didn't like the sun much and a few evenly patterned freckles on her nose that added to her cuteness. I fancied her as soon as I saw turn around and look at me in the queue, she then turned and whispered to her friend about me it seemed which gave me confidence to speak to her. I got my signal to speak to her when she picked up a yoghurt whilst waiting and dropped it. I said jokingly I hope that wasn't the last one, I was going to pick one up myself and she laughed, a deeper noise than I expected to hear but a pleasant and attractive one nonetheless. I saw an opportunity to maybe get her number so decided to try and flirt a little. I mentioned her teeth were very white and that she had a nice smile, she joked that it must be all the yoghurt she eats and I chuckled and agreed. The queue became small very quickly and I didnt find the confidence to ask for her number before she had been served and left.
As I was served and left I saw her sitting with her friend near the entrance and near some friends of mine. I took the opportunity to sit near her hoping I would find the balls to ask for her digits. I did in the end only after my friends had left though! I approached cautiously and asked if she minded me sitting with her and her friend, they said yeah sure. Introductions out of the way and now actually being straight up face to face with this chick I notice she has too sharp a bone structure in her face and her voice is feminine but deep and seems strained as if she is struggling to keep her voice steady. I asked if the girls were dating concentrating my question by staring at namoi. But they were abit taken back by my question. The brunette friend who wasn't bad looking responded sharply, "I have but she hasn't" to which the beautiful pale skinned babe naomi scowled at her friend visciously.
I got the impression she didnt like me from that and said, "you dont look happy she just told me your available" and she replied, "no its not that its complicated". I said "a boy, she said no". I said "is it coz you like girls or something she said no and before she could say another word her friend said just tell him he seems like a nice guy. To which my earlier suspicions were raised even more, I asked are you a boy or something and she said yeah really quickly and left. I followed in disbelief that I was actually following but still my legs carried me after as she made her quick escape. I stopped her soon enough and asked why she ran she just looked down. I said i really think she is cute and at that very point I see my friend come out of one of the buildings near by. My heart suddenly sinks and I think what if people knew I liked a transgender boy I would be slated for the rest of my college life so without saying another word I pull my hood up and shout my friend leaving naomi confused as to why I did that.
I have regretted that decision so much since it happened. As college sucked anyway and I didnt see her or her friend after that. There were over 2000 people on that campus its no real surprise. Anyway. What that experience did do is opened my eyes to the fact some men who dress like women look damn good doing it lol. While browsing porn some time after I felt a sudden urge to click a link with a pretty t-girl and the rest is history. I have explored many different porn sites and have begun to become hooked on shemales. So much so, it got to the point where I needed to find out if I actually would do stuff with one.
I contacted a local t-girl who was in town for the week. I was so nervous just speaking to her on the phone let alone the drive there. I stop and call her to tell her im outside. the butterflies were too much at this point so I light a cigarette. She tells me where to go and gives me the code to her apartment block. I finish my fag enter the building and head up to her room. Im greeted by a latin beauty with small slim body no taller than 5"7. Her face is nice, quite feminine which is why I chose her. The lights are dimmed and she shows me into the bedroom and starts by taking off her jeans, asking me if I came from far. I stuttered and mumbled no not far and she sensed I was scared. I stood against the wall fully clothed just staring at the wall and she called me over saying dont be scared and sat down next to her on the bed.
She rubbed my leg and leaned in to kiss me, we kissed for a few moments before she felt for my cock and pulled it out of my jeans. she started sucking it while I watched her panties bulge as her piece started to grow as she sucked me. I asked her to take her panties off becoming less nervous all the time because she was so welcoming. Her cock was at least 8 or 9 inches long, it was thick but not too thick and it stood up hard as a rock without me yet touching it. She was a brazilian tranny with light skin and a bright pink cock head a very beautiful dick by anyone's estimation. I took a knee knowing this my test was coming. So far I had enjoyed my time with her but would I actually enjoy sucking her cock. I approached slowly meeting her eyes with mine as my lips pressed against her cock head. I started by flicking her balls with my tongue and working my way up her thick shaft. I got a whiff of her musky sweaty cock as I teased its shaft with my tongue. I then moved to her dickhead which smelled amazing as I rubbed it across my nose and became lost in her sweet scents. I then without hesitation stuck her fat cock in my mouth. I sucked slowly and felt even more turned on as she moaned a few times as her cock hit the back of my throat. I wanted to fuck her now so she asked if I wanted to do doggy or missionary, I said doggy and we got into position after she had put a condom on me with her mouth. I entered her little hole slowly and fucked her hard for at least 20 minutes. I told her I was going to cum and she said okay she will cum too. I then asked if she could cum in my mouth, she started by fucking my mouth with her fat dick and letting me lick and suck her swollen glans which looked like a strawberry lollipop it was so pink and juicy. she then pumped her cock hard while I sucked her balls and before she cum she let out a big moan and gave me 5 thick shots of her healthy sperm in my mouth and on my lips and chin. I had never tasted cum before this was a first, it was so salty and thick it almost made me hurl at first but then the saltiness made me even more horny as I jerked my dick and seeing her shiver and gasp for breath while I sucked the last drops of potent cum from her cock took me over the edge. It is official. I love trannies and that will definitely not be my last time seeing one. Heck after that I would marry one!
This was my first experience and first time writing a story like this so be kind and I hope you guys liked it
not just liked it but loved it ...thanks !!
Re: It was time to try a tranny (real story no bull)
It's sometimes hard to find the right words to describe how hot and exciting sex with a Transgender girl can be. Your post did a great job of it. Great story.. thanks
Re: It was time to try a tranny (real story no bull)
What an exciting experience. I Iove stories like this.
Re: It was time to try a tranny (real story no bull)
