I don't know how long I was out but when I woke up I could see a silhouette standing in the doorway of my bedroom. I could also hear murmuring from the bathroom, so it must be Derek in the doorway.
He was sipping something. I realized it was a beer.
He walked to the side of the bed. I could barely see him, but I could tell he was sporting a woody. I don't know why but my dick started to inflate when I saw his boner.
He sat the beer on the nightstand and just stood there. I had no idea how nervous he was, but I had a belly full of butterflies. Breaking this taboo was thought to be the ultimate betrayal of manhood. Maybe it wouldn't be as bad in the dark. My room was nearly pitch black.
Because he just stood there I patted the place next to me. I don't really know why. Instinct I guess.
Derek sat down. He didn't move. I guess he was nervous, so I patted his side, and he lay next to me. I guess I'd be taking the lead.
"Are you sure you want me to do this?" I asked, half hoping he would jump out of bed and run away.
"Yeah," he croaked. He sounded like Becky. A nervous virgin who just wanted to get the first time over with.
"Do you want me to just get it over with?" I asked.
"Yeah," he croaked again. "Please, I want you to do it."
Now he wanted me to 'do it'. Earlier he was saying he wanted me to fuck him. Being confronted with the reality of what he was asking me to do must have caused him to hesitate.
I reached across to the drawer in the night stand and he grabbed my head and started kissing me. I pulled the lube out while he was sucking on my tongue.
I broke the kiss and said, "Get on all fours." Derek jumped into position. I could see his butthole. It wasn't gross. I was hoping it was empty of fecal material. Bleh.
As I was having those thoughts the bathroom door rattled and the girls came out. I could only see their silhouettes but I could tell one was naked and the other was under a blanket.
The light came on blinding Derek and I.
"Hey!" Kyla said, "I wanted to be next."
"Turn off the damn light!" I shouted. It went off. "You can't be next. I'm sort of committed now."
"Can we watch?" Kyla asked.
It was such a ridiculous question I didn't answer but Derek said, "It's okay with me." That was a shock. It was really dark, so I don't know that I would be aware of Kyla's presence once I was, you know, in flagrante butthole.
"Okay," I said, "but no chatter! Got it? No comments."
"Scouts honor," she said. I could see Marti's silhouette floating down the hallway. She wasn't interested in watching me fuck Derek.
I opened the tube of lube and squeezed some onto my hand. I saw Kyla sit on the floor in the periphery of my vision: nothing but shadows. I rubbed my hands up and down my dick. Then squeezed some on Derek's butthole. He flinched, but unlike Amanda he stayed quiet. He was being stoic.
I stroked my dick and contemplated what I was about to do. I realized I better get it over quick or I would chicken out.
I got on my knees behind Derek and walked into position. I wanted to ask him if he had had anything in there before, but knowing Amanda she'd probably strapped on a dildo and fucked him with it.
I put one hand on his hip and the other on my dick and pushed it at his anus. When my dick head was against it I put my hand on his other hip and pushed gently.
I was afraid to push too hard because he was a virgin. At least, he was a virgin to having a dick in there. Then I felt his hand on my shaft, guiding me into him, just like a girl would do.
My dick head went in and he sighed. It was half moan, half sigh. I put a little more lube over my shaft and pushed. It went in a little easier than with Amanda. Probably because Derek wanted it so badly he was mentally more prepared for it.
I could tell there was a difference between girl butt and guy butt. It felt more crowded in Derek due to his prostate.
Each time I moved back a little and pushed a little more forwards, a little further each time until I could no longer see my shaft. Derek was moaning softly.
I bent down and whispered in his ear, my shaft all the way inside him, "Is this okay?"
"Fuck me," he said, in a normal tone that Kyla could hear.
So I did. I pulled out and pushed back in, and, like with Amanda, I couldn't thrust as fast as I wanted but after his butt got used to me it was easier. I got a pretty nice rhythm going.
I was doing what ‘fags’ do, I had my penis in a guy’s anus. I could feel my entire body blushing. The taboo of the business at hand made me paranoid and glad it was so dark. It made my dick feel bigger and longer.
Normally I would reach around and twiddle a girl’s bean, but Derek had no bean. I was thrusting faster and Derek was crooning and whispering ‘fuck me, fuck me.’ I reached around and stroked his penis while I stuffed his anus.
“Oh my god!” Derek said, “You’re cock is so big! It feels so good!”
That's a new one. I’d never had a girl say that while I was going at it. It made me feel good.
I could hear Kyla crooning now. She must’ve been masturbating while she watched me fuck her friend.
When your dick is in a butthole the sensation is different because there is pressure all around the shaft at the entrance, whereas with a vagina you don't feel pressure until you are in the canal. More of the shaft feels the friction.
I was thrusting and stroking when suddenly I felt Derek’s dick start to throb. He was going to climax. Trying to keep both motions going was a little like juggling. So I stopped thrusting and concentrated on stroking. When I stopped thrusting Derek started pushing back and forth, fast and hard and then he groaned while he squirted on my quilt.
When he was finished I put my hands on his hips and began pumping. With each thrust Derek seemed to get a little looser and in the end, when I reached the pinnacle, I was thrusting very fast and I could feel my balls slapping his balls and taint.
When the prelude to my climax came Derek could sense it and he started pushing back hard against me, then I exploded in his ass. It was like fireworks. It was the most intense orgasm I’d ever experienced.
Derek collapsed and I lay on top of him with my dick still inside him. We were nearly cheek to cheek. I moved in and out a few times until it was too sensitive to continue so I pulled out.
Kyla was really going at it on the floor next to my bed. Eventually she said, “Oh oh oh.” I think she just got her rocks off.
I yawned. I said, “I need a nap.”
“Me too,” Derek said.
“Typical,” Kyla said, “As soon as a guy cums he wants to sleep.”
I laughed. Derek and I stood up and I flipped back the quilt. I crawled under and he followed. I thought Kyla might join us but she clumped back to the living room where I could hear the TV.
