1. first time penetrated


    Date: 7/2/2016, Categories: Gay, Trans, Author: sissygirl, Source: xHamster

    Girls I have been thinking about how we all started. focusing on your first time a man took your virginity by penetrating you. How it came about and how you felt afterwards. In my case I was a senior in high school just turned 18 and was a bit feminine in my appearance and certainly didn't weigh much or present a very masculine appearance. I tried to be friends with other male students but seemed to gravitate towards the girls. I admired their clothes and how free they seemed to act, hugging their friends and each other. In the gym locker room I tried to be macho in an attempt to fit in but I couldn't help but notice how my dick was a lot smaller than most of the guys. my hair was longer and I kept it neat as possible. One time while in the shower one of the football players (John) looked over at me and asked me if I liked what I saw. I responded by turning away and concentrating on my shower. He came up behind me and said I had a cute girly bottom and he patted it, then walked away. I didn't think much more about it until one of the cheerleaders came up to me later, giggling a bit and handed me a pair of panties; saying that John had given them to her to give to me and that next time he saw me I better be wearing them. The next day in gym class John came up behind me and checked to see if I had them on and told me how cute they looked on me and that since I was wearing panties I must be in need of male companionship and he would see me after class. I was so scared and ...
    didn't know what to expect but waited for him after school and he grabbed my hand and took me into an empty classroom. told me to take my pants off and get on my knees. thinking I was going to be f***ed to give him a blow job I reluctantly did so. He took off his pants and quickly picked me up turned me around and pulled me against his cock, rubbing it against my panty covered bottom and kissing my neck. being stronger and bigger than me there wasn't much I could do except try to squirm away He then pulled them down and f***ed his cock against my anal opening and without much warning he f***ed it into me and I screamed in pain. He covered my mouth with his hand and said that it was what a girl should expect the first time and since I accepted the panties given to me I was now a girl. He continued to push his cock into me and just held me tight against him. He then fucked me until he came inside me and told me that now that I was a girl I should expect more in the future. I was so scared, sore and humiliated I just pulled my panties back up and found my pants and ran out of there. The next day in class the cheerleader came up to me smiling and saying John had suggested she ask me how my meeting went with John and was my pussy a little sore still? I was too embarrassed to respond and just turned away while she laughed at me and said welcome to sissyhood as she walked away. this was my first experience with a male and he occasionally would come up to me the rest of the year and ...
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