Schoolgirls and Schoolboys

(Disclaimer: This is a true story.)

This is a story about myself, my girlfriend Shannon, and one really, really hot crossdressing dude. Or girl. A note--I would describe myself as a straight guy, while she would describe herself as 75% straight or so.

The story begins back in December or so. Shannon and I are both in our early twenties, we've been dating for a couple years, and we have a really active, hot sex life. She's a gorgeous girl, constantly being hit on by guys, while I'd consider myself only average, so I do get a bit of a self esteem issue sometimes. Also, for as long as I can remember, I've had a fetish for schoolgirl uniforms. Something about the short skirts, pure white tops, and the innocent, youthful image gets me hard.

So one day Shannon comes to me and tells me she ran into an old friend of her's, Joey. Joey was openly bisexual and I met him once or twice a while back and didn't really remember him. She said Joey has started dressing like a girl and plans to eventually undergo hormone therapy and the like. Then she dropped a little bombshell that was meant to be a joke:

"He's got a thing for schoolgirl outfits."

My ears perked up for some reason. We discussed him for a little while and then she--again, jokingly--proposed the idea of a threesome. I immediately accepted. She thought I was joking back, but I told her I was serious. She got turned on at the idea and decided to ask Joey about it.

Two nights later, around midnight, Shannon arrives with Joey in tow. My apartment lights have been dimmed to semidarkness. At this point, I got my first look at Joey.

He was the most feminine looking guy I'd ever seen; had I not known ahead of time he could have easily fooled me into thinking he was a girl. He had long black hair tied into pigtails, all the hair on his body was completely shaved and his legs were waxed. He had piercing blue eyes surrounded by eyeshadow and this gorgeous, perfect smile framed by pink lipstick.

Shannon left us alone for a moment and Joey took this time to tell me he thought I was really cute. I could feel my face burning up and went to sit on the couch. Joey came over and sat on my lap. In the semidarkness he looked just like a girl in a school uniform, but I could feel the bulge between his legs. I nervously complimented him on how feminine he looked, and we slowly started to kiss.

I explored his warm, delicious, strawberry flavored mouth with excitement, pretending he was a hot girl, and my eyes would fill in the rest of the picture. Eventually, I felt like my cock was going to burst out of my sweatpants, and just in the nick of time, Shannon returned, giggling at us. I masturbated a bit as Joey pulled his panties off and started fucking Shannon from behind. After a little while he stopped, came over to me, and looked up at me with those big blue eyes. I closed my own and moaned as I felt him start sucking me off. After what seemed like only a few seconds I blew my load in his mouth.

Then he went back to nailing her. I loved watching her get off from another guy. But in the darkness all I could focus on was Joey's smooth, hairless, sweat soaked ass peeking from under his plaid skirt. In a lust-filled trance, I crawled over, pulled his ass cheeks apart, and slid my tongue in his hole. It wasn't my first time rimming, but it was certainly the best. He came, I came, she came, and everybody was happy.

He slept over and we woke up early the next morning before Shannon did, while it was still dark. Still in my lust-trance, I led Joey to the shower and turned it on. I got naked but told him to stay in his schoolgirl uniform. Then we got in the shower and I ran the soap all over his ass and smooth legs. I was so horny and couldn't stand it anymore. I took as much of his cock in my mouth as I could and sucked him off until he blew. Then I pinned him against the wall, shower water pounding on us, and began ramming him in the ass. It was the most arousing, hardcore anal of my life and I loved every second of it.

When we finished, he gave me a kiss and left. Shannon woke up and I told her Joey must have left in the night sometime. Our shower rendezvous would be our secret.