What the Heck is Anal Masturbation?

So, after I graduated college in the mid-nineties, I moved back in with my parents in my hometown in Northern Michigan for the summer to get my bearings before venturing out into the real world. My youngest brother at the time was attending a local community college and he was also still living at home. He had a small group of friends he liked to hang out with and sometimes they would get drunk together on weekends in our parents' basement. I never really partook, but I left them alone to do their thing. They would sometimes come upstairs and use the bathroom, so my interactions with them were minimal. 

His one friend, B***** was blond, lanky and athletic. He was actually a spitting image of my brother. He was probably the most engaging member of the group. Occasionally, he would chat me up. One summer night, the conversation took a decidedly sexual turn. He was visibly intoxicated and giggling to himself while standing in my bedroom doorway. The hall light reflected off his biceps. He was wearing basketball shorts and a wife beater.  Something was obviously on his mind. After the usual small talk, I finally asked:

-Hey, man, what's up? What's so funny?

-Have you ever masturbated anally?

-Uhm, what?! I laughed nervously, not sure where this was headed.

-You know... He blushed with a shit eating grin.

-Uh, I don't know actually, what the hell are you talking about? What the heck is anal masturbation, I asked trying to sound more intrigued than judgmental. It obviously worked, because he adjusted his swelling junk in his basketball shorts.

-You know, stick a finger up your butt while jerking off. He simulated jacking off with one hand while making poking motions at me with the middle finger of his other hand. 

-OMG. I laughed out loud, and said enthusiastically, -That sounds hot, but I don't think I'm that coordinated. 

-You should try it, man... it's intense.

-Sounds like a two person job. I laughed and stared directly at the bulge in his shorts. He was definitely sporting wood. But that was the end of it. He laughed and returned to the basement where he presumably continued to get shit-faced with my brother and his friends. For all I knew, they were all down there "masturbating anally." I thought about beating off, but I just lazily drifted off to sleep.

It was a few hours later when I was nodding off to sleep that I heard my bedroom door open and someone stagger into my room. I strained to focus in the dark, to see that he was back. 

Groggily, I said, -Hey, B***** the bathroom is across the hall. Are you wasted?

-Nah, he responded, coming closer. He was obviously full of liquid courage. -I was just thinking about what we were talking about earlier. I want to help you out. 

-What do you mean?

-I think you know what I mean, he slurred falling onto my twin bed. I slid over to give him room, while bringing my knees up. He actually wrapped is arms around them to steady himself upright. With one hand, he fumbled under the bad sheet. It was hot, my parents didn't believe in central air. A faint breeze from off of Lake Huron blew past us. I could smell beer and Jagermeister on him. He was breathing heavy. His one hand cupped my knee cap, and the other was still fumbling under the sheet for my boxer shorts. 

At this point I was raging hard and trembling a bit. B***** was mildly inebriated and all business. His hand gripped my boner which was sticking straight out of my boxer shorts. I laughed nervously, and lowered one knee which caused him to lose his balance and fall across my bed. His grip on my cock tightened as he steadied himself. 

-Are you for real, seriously? I asked incredulously. 

-Real as fuck, he slurred huskily. You need to experience this. It will blow your mind. Do you know about the prostate?

-I've heard a few things, I laughed awkwardly as I gasped. He was stroking me intently and I was starting to leak pre-cum. He had all of the intensity and skill of a drunken surgeon. 

I couldn't believe this was happening. He let go of my knee and slipped his hand between my legs and cupped my balls. He never let go of my throbbing cock, and with his middle finger he twirled it around in my pooling precum. I slid my ass up off the bed as he brought his middle finger to his mouth. He sucked on it for a few seconds, getting it nice and sloppy. I think my eyes must've been bulging out of my head, because he laughed a little as his finger located my asshole. Was this for real? His wet finger played with my butthole as he stroked my dick.

-I think the prostate is inside, I offered. I reached down under my bed and pulled out some lotion, which he grabbed out of my hand.

-You said you never done this before, he said accusingly.

-I haven't!

-You just keep this next to your bed, and never think to stick a finger up your own butt?

-No, I never gave it any thought before, I said truthfully. By now both his hands were slick with lotion. but one hand was gripped like a vice around my dick and the other was penetrating me. I writhed on the bed, shaking with complete horny desire. I could see his tenting shorts were straining to contain his stiffy. When I reached for it, he swatted my hand away. 

-No way, this is for you, you're always so nice to me, I wanted to do something for you, that you'll never forget, that will rock your world, he said grinning. You have a nice thick cock btw.

I gripped the bed as he finger fucked me vigorously working my prostate. I kept thinking he must've practiced all the time on himself, as he knew right were it was and what to do. I clenched my ass cheeks together and raised my hips off the bed as he drove his finger in deep and gripped my dick hard. He sensed I was about to blow, and didn't do anything more as I pumped into his hand slammed down onto his finger. 

I shot massive amounts of cum like I never had before in my life. It shot past my abs onto my neck and chest. B***** smiled approvingly. He loosened his grip on my dick and slowly pulled his finger out from inside me. He twirled it around my asshole a few times while I lay some what embarrassed and completely spent. He grabbed a sock off the floor and cleaned me up while giggling and commenting on what a mess I'd made of myself. My breathing returned to normal as I lay there. 

-Wow, was all I could say.

-Told ya' you'd like it. Hey, I really got to piss.

And just like that, he left my room without a word. I lay awake, half hoping he would come back and demand that I return the favor. And I never did find that cum soaked sock. I think he must have pocketed it and taken it with him.