LITTLE BILLY

Last week I regaled another story of the time I lost my virginity when the clan and I were all telling of our "first time sex" stories over drinks for Pride. Well, here's another one from way back in the mid 90' when I lived in downtown Harrisburg with a housemate. We rented a four-story townhome right in the heart of the downtown. Now I don't know what it is with me and Prides, but something sexual always happens. My first ever gay pride I met two guys, a couple, and that ended up being my first ever threesome. This story was two years later. After the festival, everyone went separate ways home to rest before our big Pride party that evening. Not being a big napper then, and being newly living in the downtown, I thought I'd go have a few drinks and see what trouble I could find. It was hot, and sultry that day and I went on the prowl. So I go to a place called the Strawberry Lounge and to my delight there are a few possibilities. What do I do? I sit next to the one impossibility. He was super-hot, chiseled everywhere, major jock, killer smile... and looked like a young George Clooney when he was young, like on Facts of Life. But better than that, he reminded me of one of the hot jocks from high school I'd had a crush on, who was also out and slept with the other four out gay boys in school but me!  So anywhore, he looks at me, I'm looking at him...he is pulling up and down on the neck of his Rolling Rock bottle, and I'm rimming my finger around my cocktail glass. Finally, he says," What are you up too?" I says, "Oh you know, just looking for sex." I have always found the direct approach works best. Then he asks me what my wildest fantasy was. I said I didn't really have one. I just like to see where the day or night takes me. I then said, but you must have one, because you asked the question. And he said, Yeah, I do. When I was in grade school, I had a huge crush on my friend little Billy. One day I rushed to his house, and was greeted by his mother, we talked, and she told me to go right on upstairs, he was in his bedroom. But as I went up something felt different that day. I got to the top of the stairs and his door was closed with exception to a slight crack. I opened the door, and there was little Billy, on the bed, Fruit of the Looms and pants down around his ankles, bare butt up, humping a pillow. I said little Billy! He turned in shocked, red, and said well, buddy you caught me. I then started to walk over to the bed."  Well, I interrupt and say I guess you want to reenact this?  And I'm to be little Billy? He says..."Yep are you up for it? He looked down and saw I was. I finally said yes, I'm up for it, and better than that I live in a four-floor townhouse, and my bedroom is on the top floor, so your fantasy is going to be that much more authentic. 

So, I down my gin, give him my address and ask he give me a five-minute head start. I ran home, in, and took two steps at a time. He was going to get little Billy and I was going to get my fantasy of the high school jock. I unmake the bed, putting the humping pillow in place and pull off my shirt and pull down my jeans and Calvins. I start to hump the pillow when I hear the door open and shut, I hear him acting like he's talking to little Billys mother, and says Thanks Miss H, I'll go right up. And I'm thinking to myself, he really knows this script. I then hear him coming step by step up the stairs, he's close, then I hear the door opens and he says Little Billy! I turn in shock and red, but not from embarrassment, but from the running and the gins from earlier...and I say," Hey Buddy you caught me." he says "I sure did!" He then starts to walk toward me, and I can see he's majorly tenting. I reach out and pull down his jeans and his tighty whities and out pops a big, beautiful kielbasa sausage, and I want to say hold the bun, put the ketchup and onions on the side, and just as I lunge for it, he dribbles out, he pulls away, pulls up his tighy whites and jeans and says, "Thanks Buddy! Thats was hot...You did great!" I said "Thats it...THATS IT!" Thats what I wanted to say but was too flabbergasted to say anything. Why not just leave me $100 on the dresser why you're at it. He leaves, I hear him go down the stairs and out the door, while I'm lying there still hard and laying on the humping pillow. Mind you I also didn't hear him say goodbye to little Billy's mother on the way out, which I found rude. And then I'm like, this isn't the first time he's done this. This guy is in a rut.I also wondered how many other little Billy victims were out there. I wanted to go find them and start a support group! And what about me? I didn't even get my high school jock crush fantasy come to life. But....but I didn't tell him that did I?

 I learned a very valuable lesson that day. Never be afraid to ask for exactly what you want, you might just get it. 

Hey, it worked for him.