1. My Coworker Lily


    Date: 9/20/2017, Categories: First Time, Trans, Author: camay1997, Source: xHamster

    I’d worked with this girl Lily for the last four years. She was a 27 year old size four, 161.3 cm tall, with pale skin, long dark straight hair and brown eyes behind unstylish glasses. She was pleasant to everyone unless you didn’t take her rejection well; then she cussed like a drill instructor from the 1970’s. I’d seen her in action and never bothered to ask her out. Women our age aren’t attracted to guys who play videogames, drink beer, watch sports and read comics with their spare time. After a while I found out she was a fan of videogames and manga. So we grew to be friends. 29 days ago she came over to my one bedroom apartment to play Overwatch; her power was out due to construction. We played for two hours before ordering pizza and continued playing until it was delivered. We turned off the game to watch A Few Good Men and eat. She was sipping a Mike’s hard lemonade and clearly as bored with the film as I was so I thought I’d take a chance. I returned from the kitchen with my third PBR sat down and asked, “Why don’t you have a boyfriend?” “You know why.” She grumbled trying to pay more attention to the movie. “Yeah I know, ‘Guys can’t deal with them taking a back seat when the new issue of Magi - Labyrinth of Magic comes out.’ So you’ve said. But in the entire four years I’ve known you, you’ve never had a boyfriend. And I was just thinking, I could deal with a girl who loves videogames and can relate to my love of comic books so why don’t you and I go out? I’m not ...
    saying we’d have to do anything or be boyfriend and girlfriend or anything like that. We could just give...it...a...chance…” I’d had my eyes closed from “And I was just thinking” to “We could just give…”. Now that I’d opened them I saw her staring at me with an expression best described as flummoxed on her face. I start to back peddle but no coherent words come out. So I stop talking and let an awkward silence settle. After 155 seconds I was about to apologize when she said, “Oh, I thought you knew. I mean everyone else we work with figured it out and you’ve known me the longest. Lance, I’m transgender.” “Huh?” I replied. “I was born a boy and started hormones in my teens to become a woman.” “Oh. So do you still like have a penis and stuff?” I was so horrified I’d asked this I dropped the beer can in my hand. It landed upright between my legs. I picked it up and chugged it to stop any foam up as she replied, “Well, yeah.” “You’re just saying that to not go out with me, you’re a liar Lily.” I said thinking about how to change the subject when she stood up and pulled her black skirt down revealing teal cotton panties. She pulled those down to reveal a cute little dick beneath a groomed but thick pubic mound. I felt my uncircumcised cock enlarging in my grey boxer briefs. I licked my lips and asked if I could touch it. She nodded and I started stroking it, watching it get harder. It grew to 11 cm in length, and was the circumference of a US quarter. Without asking I had her cock in ...
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