Alan had me over his knee, and had progressed to spanking me bare-assed, with the pink satin dress that he had convinced me to wear; he had flipped it over my head, and the satin sissy panties were down over my butt-cheeks. Alan was administering the hardest bare-butt spanking I could ever remember. And here I was, almost 20 years old!
I started crying like a little kid. My erect penis and balls were trapped in the front of the satin briefs, pressed up hard against Alan's lap; my bottom was burning and I am sure it was beet-red. "Let it out, Billy, let it out!" Alan was encouraging me. I could feel the stress of the last week leaving my whole body as he wailed on me! It was the most amazing release. I cried and bawled and screamed each time he hit me.
Finally Alan started to slow down. He rubbed my bottom between spanks; then he would tease my inflamed ass-cheeks with the puffy panties or the slippery nylon of the dress material. He forced his free hand down under my hips and started to massage my cock through the thick satin panties. I was still wimpering but enjoying every minute of his attention! It felt GREAT, laying there in his lap.
I came close to orgasm several times but he would stop me by squeezing the base of my penis very hard; so hard it hurt. "Don't come yet, Billy." "Yes, sir."
A few moreminutes and he had me stand up. I was quite wobbly and felt dizzy. He steadied me and let me to his bedroom. Alan had me lay on his satin comforter as he removed his sweatsuit. I got to see him naked for the first time; he was in pretty good shape for a 50 year old! Slight paunch, nice build. I was quite excited as it was obvious what was going to happen next. Alan asked me if I had ever made love with another man before. Aside from a few hesitant experiences with my friends, I answered, "No, sir". Alan asked me if I wanted to be fucked. I said, "Yes, sir!". I was quite ready for whatever he wanted to do.
With that, Alan got on the bed and straddled me with his legs, me on my back. He pulled down my panties, teasing my cock and balls along the way. I loved the feel of the elastic of the bloomer-panties sliding down my thighs and over my knees, and the feel of a man undressing me! Alan kissed my penis and licked it, then proceded to give me my first experience with fellatio. He was great! Then he grabbed a tube of lube from his nightstand and put some on his finger, and raised one of my legs up and over, to bare my ass. I thought it would be painful; but he just massaged my rectum gently for several minutes and kept telling me to relax. I wanted him. I wanted to be fucked, to feel what it was like.
Alan kept working on me until he thought I was ready. Then he hoisted both of my legs over his shoulders and I felt his penis at my back door. I desperately wanted it. I had played with toys and loved it, and wanted the real thing. The dress was stimulating the hell out of both of us. Alan just kept working on my love hole with his hardness, encouraging me, telling me that I had to want it, and so on. Well I will tell you that at some point, his cock started to enter me and I had the most intense pain; Alan told me that was normal for "virgins" and to just relax. He waited until the entry spasms subsided, then pushed...
Oooowwwwwwww, owwww, ow ow ow oh...
I felt utterly helpless and enslaved to him at that point. I loved the feeling of being violated, fucked like a girl, and wondered at that point what complete emasculation would be like... don't know why, but I had a fleeting fantasy of Alan taking my balls. I think it was just the impact of the way he took me; the spanking, the control, all new to me. But I wanted more! I told him so too. He gave it to me. That horny guy hammered on my ass for a good fifteen minutes. Precum was dribbling from my cock all over my belly and the nice dress. I could not see him from the belly down because of the pink dress in the way. Alan started grunting and I could tell he was close. I wanted to please him so I clenched my ass muscles. He went nuts! I was being "raped" and I loved it. I started hollering "No, no, please"... that turned him on more and he just kept me mounted and bucking..."Daddy, don't!" I screamed in falsetto, just to see what would happen. Well that sent him over the edge!
As Alan came in me, I started to orgasm, squirting in the folds of the dress; I never even touched my penis! My orgasm actually started in my bottom and radiated toward the base of my penis, then up the shaft. I cried out again and again as Alan let me have it. He fucked the heck out of me as I came, under his control.
After Alan pulled out, he lay down next to me, spent. I rolled over, he threw an arm over my mid-section and we both fell asleep.
billy