Alan led me over to the sofa and sat me down. He offered me another beer. This time, he brought it to me in a glass. I sipped the beer as he asked me questions. "Have you ever done anything like this?" "No." "Does it feel good?" "Yes." "What does it feel like?". I commenced to tell him exactly how I felt, in that pink dress and panties. "Like a damn sissy," I said. "Drop the 'damn', and tell me again." "Like a sissy!".
"Billy, tell me about your sexual experiences." I stammered, not sure what he wanted. "You mean all around, or with guys?" I hit the nail on the head. "Guys." I told him about Cricket Boy and our spanking sessions. He was obviously stimulated. I saw his erection growing in his sweats. He asked me if I would like to re-live those sessions, with him. I thought about one second, and then said, "Yes!" I was squirming on the couch like a little girl. Everytime I moved, the satin panties got me even hotter than before.
Alan asked me if he could touch me. "Yes." He had me stand up in front of him. He told me that I would have to get used to a man touching him, not a boy. I stood there, still squirming around in the dress. I loved this! Alan started to straighten the dress and the bow in front, re-arranging it, turning me around and flattering me. "You look great, Billy." I was ecstatic, stoned, and horny. It was like a sexual Alice-in-Wonderland but for real!
Alan had me lie on the couch, face down. He pulled up an ottoman, so that he was sitting beside me. He lifted the skirt, slowly, up the back of my legs, rubbing it on my electrified skin as he went. He got to my buttocks and rubbed them through the skirt and panties. I was starting to hump on the couch, first to get my privates re-arranged, then for the pleasure.
Alan got the dress up over my head in back. I was exposed, except for the satin panties. He gently rubbed and kneaded my buttocks, asking me if I liked this, or that. I answered mostly "Uh huh". Alan told me to start using "Yes sir, or no sir, and please sir". I just wanted him to continue, so I did. He told me he was going to spank me now, and my cock jumped big time! He slapped his hand across one of my plump cheeks. "Smack!" It didn't even hurt, but I felt it. He did it again, and a third time, then asked me if I was OK. I said, "Yeah". "Yes sir," he reminded me. "Yes SIR". He continued. "I will now spank you harder, for dressing in girl's clothing, Billy." "Yes, sir." With that, he nailed me a good one! THAT one stung! Right through the slippery satin fabric onto my ass-cheek, direct, man-to-man. I suddenly remembered that MY DAD HAD NEVER, EVER SPANKED ME as a kid! How odd I should think of that.
Alan continued working over my butt. After a while, he reached over with both hands, and gently worked the waist band of the panties over my now-red ass cheeks. They burned, but the satin felt wonderful. I thrust my bottom up and down, as he bared it. I knew what was to come! "I will now spank you bare-bottom, Billy, but I want you over my knees." Alan got up and motioned for me to sit up. I did, then he sat on the couch, and I lay down across his lap. I felt his hard erection through his sweats instantly. It got harder and throbbed as he again bared my butt from the dress. The satin fabric was cool and very stimulating on my sensitive butt-cheeks and he made the most of it, teasing me with the hem of the dress and the elastic of the panties, playing them up and down my reddened butt. I was quite wet in front of the panties by now.