I basically lost my virginity because I got raped kind of..
I started cross dressing when I was just 12. I would wear my moms or sisters underwear to school and I would even wear my moms lingerie or nightgowns to bed. I loved the silky ones the most but any women’s clothes turned me on.
When I was 14 and in 9th grade, I was going pretty hard on the cross dressing. I would wear a pair of panties to school every day and even on cold days I would wear a bra underneath my big sweatshirt.
One day when I was a freshman I was in the locker room after school and two seniors walked in. These two guys were bullies but not the worst I had in those days. I assumed they’d just leave me alone but I thought wrong. They were there specifically for me. After some verbal abuse they decided to stand me up and push me around. When I lost my focus, one of them snuck behind me and pulled my pants down. He had grabbed a hold of my boxers that I wore over my panties, most likely by choice and yanked them to my knees, revealing my panties. They made fun of me and spread it thru the school. By the next morning everyone knew and I was at the very bottom of the food chain.
About a week later I noticed a car following me home as I walked along the sidewalk. I got scared at ran and unfortunately ran into a near by woods. I thought I had gotten away but suddenly two guys approached and it was the same two that had pulled my pants down. They had me trapped and alone.
“Please leave me alone.” I pleaded as they stared at me silently
“Get on your knees kid. You’re gonna take care of us.” One of them finally said
I protested as much as I could but I was out sized and out numbered so they shoved me to the ground.
“Get up on your knees! We’re not asking again!” The other guy demanded
I did as they asked for fear they’d beat me up and I wasn’t in any way trying to get hit. They both unbuttoned their pants and pulled out their cocks. They both had semi hard cocks that were about 7” long.
“You wanna be girl? Then we’ll treat you like one. Suck our dicks!” They demanded
The more and more I dressed in women’s clothing, the more I wanted to explore being with another guy. The Gods honest truth was, when they pulled their cocks out and they became fully erect, I wanted to suck them both! However, the joke about me going around school hadn’t died down yet and I really didn’t want to let them know I wanted this. I waited until they got impatient and began forcefully pushing their cocks in my mouth. That turned me on beyond belief! Again, I still pretended I didn’t like it. All of my acting kind of made it more erotic. It made me so hot having to guys force me suck their cocks! The more I fought it, the more turned on I got.
It didn’t take long before the first guy came in my mouth. As soon as his cum hit my tongue I realized I liked sucking cocks. As soon as he pulled out, the other guy shoved his cock in my mouth and shot his load almost immediately.
Had they pulled up their pants and left, I wouldn’t have been upset one bit. In fact I would’ve probably gone home, put on some women’s lingerie and masturbated as much as I could because I was as hard as a rock! They did not leave it at that.
“I’m not done with you freak!” One of the guys said “…keep a watch out.” He added to the other guy
He got down on his knees next to me and pushed me. I landed on my hands and knees and before I could even try to get up, he had pulled my pants down to my knees. He quickly put the tip of his cock against my hole, spit on his cock and pushed it inside my asshole. I cried out in pain and all that about being turned on and rock hard went away.
“What the fuck are you doing?!” The second guy asked frantically
“Making him a girl! Just shut up and keep an eye out.” He muttered “…cover his mouth, someone is gonna hear him.”
The second guy reluctantly covered my mouth with his hand and I screamed and cried into his palm. The first guy had a firm grip on my hips controlling me as he slid his cock in and out of my ass. After about 5 minutes of him thrusting in and out of me, he let out a moan, tensed up and hurled over my back pressing his mouth to the back of my ear. I could hear his moans and heavy breathing as his cum filled my ass. As he pulled out, he quickly pulled his pants up and they both ran away. I laid there for about 10 minutes crying. My ass hurt so bad!
I finally composed myself enough to stand up and pull up my pants. His cum still trickled from my ass and down my leg the entire walk home. When I finally did make it home I ran to my bedroom and cried for almost an hour. I made the decision to not tell anyone.
That night as I laid in bed, I started replaying the whole incident in my head. I started remembering how much I enjoyed their cocks in my mouth and the taste of their cum hitting my tongue. Suddenly I found myself justifying the whole thing and even thinking that if they had just been gentle, I would’ve really enjoyed getting my ass fucked.
The next day I convinced my mom to let me stay home from school. As soon as she left for work, I had the whole house to myself for 8 hours. I darted into my moms room and found my favorite clothes of hers to wear. A black silk one piece lingerie, and a pair of black stockings. I even squeezed my feet into a pair of her old high heels. After just laying in bed playing with myself for an hour, I removed all the clothes and put them away. I grabbed my moms vibrator and stared at it for a few moments. I wanted to know what it felt like when it went in gently.
I rubbed some lotion on the vibrator and pressed it softly against my hole. It wasn’t a penis shaped vibrator, just a silver wand looking thing. It slid in and I began pushing it in and out harder and faster until the vibration made me cum harder than I thought I could.
In the days after I would graduate to my moms dildos. Ever since then I have always loved cock in my ass. Those boys left me alone after that day in the woods but I kind of always wished they hadnt….