Well I ran into an old elementary school friend Billy. He and I go way back. We went to school together from second grade through sixth. I was in a local shopping mall when all of a sudden I heard a voice from the past. I turned around and there was my old classmate and best friend Billy. Now I hadn't seen him since the mid eighties. We talked for a bit and we chatted for a bit and I invited him over for dinner on Friday evening. He was really excited about getting together.
Billy and I were really close but we went to different schools after elementary school so we like many people drifted apart. In fact we would have sleep overs at our houses and have so much fun. The last sleep over was really a crazy one it was Christmas 1977. Billy came to my house and we stayed up all night. Playing records and watching television and talking about being in Jr. High School. Billy also brought over a collection of his fathers Playboy. It was around 11:00 pm and Billy got out the Playboys. I was so excited at new material and lots of it. I only had one of my brothers OUI magazines and had that memorized. I had been masturbating to it and the Sears catalogue for a good while.
Not sure how it came up but I believe that Billy started talking about how he masturbated to the Playboys. Being such close friends I had no trouble talking about it with him. In our fully finished basement which had a work room, a bedroom, complete kitchen, laundry room and then the family room with two couches that when you took the covers off doubled as beds. The lights were off except for the television. Billy and I stripped down to our underwear. He was on one of the couch beds and me on the other. We both ended up naked masturbating to the hot nudes in the magazines. Billy and I talked about what turned us on. I told him that I thought my masturbating was going to payoff to whoever I ended up with.
I wasn't embarrassed at all to reveal myself to him nor was he to me. Billy was taller than me now as I was taller than him up till sixth grade. I wanted to see his penis to see how I compared. I went to the work room and came back with a tape measure. He went first and he measured himself at just about seven inches. I then measured myself and the way I first did it I got six inches. Billy told me I did it wrong and he re measured me at five and half inches. Wow so Billy was bigger than me by one and a half inches. This was the start of my fascination with other men's cocks and comparing them to see how I measured up. This would be my first loss to a bigger guy. One of just many and I had better get used to it.
Billy came over to my bed and laid down at the other end with his magazine and continued masturbating. We talked about how much seamen we made. Billy asked me what if we did each other to make it more exciting. He said that it would feel really good if we did. He asked if I was afraid to do it. I told him that I would be ok if he was and only if he swore that no one would ever know what we did. He agreed to it and we spit on our hands and then shook on it. I then had a really great idea. In the spare bedroom down in the basement was a closet with a few of my sisters dresses and the dresser had panties and other under garments. I told Billy about my idea and he was really excited.
So I went in the bedroom and found this really sexy red sequin dress. I also found a full pair of panty hose control top. I put them on and also used some makeup and then put on lip stick and to top it off I found a pair of high heels I could squeeze into. When I came out of the bedroom Billy whistled at me. My hair was long then as was most guys in the mid to late seventies. I gave myself a shot of her perfume too. Then I laid down next to Billy and I started stroking his super hard erection. I was really turned on and my boner was hurting me pressing hard against the sequin dress.
I stroked him and he was really enjoying it and I could hardly wait until my turn that is if I lasted that long. Then he decided to stand up while I knelt in front of him and stroking his long hard cock. Now I have always been an ass guy loving to squeeze and rub or be rubbed. So I took my free hand and rubbed his ass. He really enjoyed it and he became harder if that was possible. I didn't think about anything other than what I was doing. I was so aroused stroking him and rubbing his sexy ass. Billy began telling me how hot I looked. He wanted me to bend over so he could pretend to hump my ass. He told me that my ass looked more like a girls ass especially in the panty hose.
He rubbed his long cock up and down my crack. Then I felt him pulling at the panty hose and he pulled them down. I felt his head poking my very tight hole. I told him no back door. He continued to rub it up and down my crack. Then Billy decided he wanted a change. He started talking about blow jobs and asked if I had ever had one. I said that I fantasized about it but never had it done. He told me that he watched his older sister blowing her boyfriend in their basement. Billy asked me if I would try and do it to him. I told him that I wasn't sure about it. Billy kept on till I finally caved in because he said he would do it to me. So there I was really exploring the possibilities with my best friend.
He told me what to do from seeing his sister. First I licked his long shaft and then I ran my tongue over the tip before taking him in my mouth. I never told anyone about what I did including my wife. Billy said he never told anyone about our experiment either. I got him a couple times with my teeth by accident and I was going to stop but he told me to keep going anyway. I did working on his sexy cock and had to stop several times cause I got hair in my mouth. Then without warning I felt him let go and filled my mouth. It was very warm and kind of sweet tasting. I gagged a bit but managed to swallow most of it. I ran and got a drink of orange soda to clear my mouth. Billy wouldn't wear the dress and he didn't give me head but he did rub my ass and get me off stroking me though. I wanted to finally tell about our night and this now leads up to the dinner on Friday night with my wife.
