1. My First Time With A Boy!


    Date: 5/4/2017, Categories: Anal, First Time, Shemales, Author: Ivygurl86, Rating: 100, Source: xHamster

    These stories always start out with "the summer after high school" or "my first semester of college" but it doesn't gravitate to the true experience felt when actually going through changes in your life....hormonal changes. So let's just say for the sake of this story, that I was a teen....and he was a teen, and a teen is 13-19 years in age. But none of that matters. What's important is that this time of my life was full of huge changes. Cross-dressing was not new to me at this point, and by now I had well broken into the habit of using my mom's make-up. I mean, every time I looked in the mirror, I saw a girl. But I didn't want this! I wanted to fit in like all the other boys. I got teased, picked on, and had major self confidence issues. "Fuck!!! Just grow some damn abs!" I would always think. My hips and booty were not right, and I was super embarrassed to ever show my legs. LOL I didn't even really grow hair on my legs. I thought "What's wrong with me? Why do I do this? Why do I feel this?" My mom caught me once, and it was tragic. When in school, I was always in band. I loved it and needed a serious outlet for all my energy...and I loved to wrap my lips around the mouth piece of my saxophone. Maybe that's how it all started. Maybe he saw me first. In either or any way, that's how I meet Robert. He and I became good friends right away. We meet each other in band because we were both a couple of goof balls. He played trumpet and I played sax. We sat fairly close....close ...
    enough to joke around all day. We became friends that would talk on the phone, hangout with girls, go to the movies, and have a blast as teens. But I also hung out with him all the time during the summer. My mom and step dad were divorced, so my mom and I didn't have much money...we lived in a small apartment in the "not so nice" area of town. Robert however, lived across form the park, park district office, and pool. His parents had money, thus a much nicer house so I had no problem going over there every day. I would come over, and we would scavenge through his dads cigarette butts to have some smokes....get high, and get d***k! Or maybe that's how it started. I can't deny that every time I saw Robert, I thought he was so hot. He was so athletic also and had super ripped muscles. But I was just some super skinny dork, that looked like a girl and no one liked. Why did he like me? This one particular morning was going to be special. When I arrived at Robert's house, he already a J ready and rolled. This is just what we did.....did I mention that we would watch porn together and jerk off...I mean best buddies right :-p But this was it! I started to realize that everyone in this world is a liar when it comes to pot and alcohol. That shit doesn't make you "black-out" and forget...Oh I remember every single time I have ever got d***k. There's no excuses. But it does give you "courage". And I was so fucking horny. Regardless of Robert or not, I just felt so femme inside that it was ...
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