My First Time
I'll never forget the day I lost my virginity as a cute crossdresser...
I remember I was 16 when I first started becoming interested in girl's clothes. When my parents would go out I would try on my mom's sexy panties and nylon stockings. They would fit right over my slender teenage body. I had always kind of been interested in guys but it wasn't until I started crossdressing that I started jerking off to gay porn. The idea of being fucked in the ass used to turn me on so much. I remember the first time I fingered myself and I came so hard.
I'll never forget meeting Brandon. He transferred into our school from France. I remember the day he walked into my classroom. I got so fucking hard in my tight red and black thong under my school pants. We quickly became friends as he was such a nice guy. It was on the week that my parents went away on holidays that I knew I needed him. We had arranged to go to my house after school before we would go to the movies. As we walked to my house I could feel my heart throbbing in my chest. I told him to chill out in the living room because I was just gonna go get changed but he didn't exactly know what I meant.
I had been saving this sexy tight black skirt for a while so I slid that on, it barely covering my ass. Then some silky red panties and black nylon stockings. I put on a sexy black bra before putting on my tight pink tank top. I looked so hot. Some black eye shadow and red lipstick and I was ready. I already had lengthy girlish brown hair so I looked perfect. I slowly strutted into the living room in my high heels.
"Wow!" Brandon let out.
"You like what you see?" I asked in a very girly voice.
"I'm what, silly?"
"You're fuckin' hot!"
I started to blush before walking towards him. I could tell he wasn't sure what to do but when I grabbed him by the cock, he felt very ready. I gently kissed his lips before he slid his warm tongue into my mouth. Our tongues intwined was so good before I slid to my knees. This was when Brandon went from this quiet kind sweetheart to this animal. His hard 6 inch cock staring at me, I slowly wrapped my lips around it before he grabbed my hair and started to face fuck me so hard. I loved it! Gagging on his hard cock. Tasting his hot sweet cum.
He pulled me up and threw me onto the couch. On all fours, he slid his hands up my skirt and pulled off my panties. Before I knew it, his tongue was in my ass. I couldn't believe it: My first rimjob! It felt so good. Having his wet tongue deep in my tight little shithole was so fuckin' good.
He asked me did I have any lube and I didn't. I felt so stupid! He spat on his fingers and whispered "well we'll have to make do" before sliding to fingers up my ass. I left out the girliest screech I ever could but I loved it. Feeling his fingers go right past my sphincter was too good and through my moaning I whimpered, "I want your cock inside of me".
I felt it poke at the door of my filthy asshole and I let him right in. He slid in all at once and I thought I was going to shit myself but then I realised that this was how it felt and it was amazing. He grabbed me by the hips and hair fucking me so hard. Streching my asshole more with every thrust. I began to cry from the pain but in a lustful way. I loved it. I loved being fucked like a 16 year old whore. My tight little shithole getting fucked and torn up by Brandon's hard cock! I screamed, "Fuck me harder!"
He started to thrust harder and call me a dirty fucking slut which I loved! He moaned, "I'm gonna cum," which was great cause so was I just then I felt it! That roasting hot rush of cum fill up my dirty bowels! I came all over the couch. He pulled out of me and watched as I slowly shit his cum back out of my ass. He slid his finger back into my ass dripping with his cum and made me taste it. It was so good.
Let's just say we never made it to the movie.