After moving from my first home, and loosing touch with my "cricket dud", I did not have another spanking until I was 20.
I had found a room with a man named Alan, who was divorced and in his 50's. We got along very well. I cleaned house in exchange for room and board (shared the food and beer expenses!).
We were having a few beers on a Friday night (drinking age was 18 then) when Alan brought up the subject of hobbies. I told him mine (electronics, music and swimming) and he told me that he collects uniforms, and asked if I would like to see them. I said sure and we went upstairs to his bedroom. He had a huge bedroom, light and airy and two large closets. He went to the walk-in and opened it. A light turned on automatically. I looked around for the switch, and then saw something that made my jaw drop; there was a huge collection of military gear in there on one wall; on the other was all pink, light green and white satin stuff! I started to get erect right there, just looking.
Alan brushed past me and started telling me about all his stuff. He said that it might sound kinda kinky and if I was turned off, that he would understand. Quite the opposite, I love satin stuff! and I had always loved snowsuits, overalls and insulated gear since I was a little boy. I was checking everything out, feeling all the different materials, and getting more and more horny.
I flashed back to my encounters with Cricket Boy. I thought, "no way, dude...". Alan was watching me to see what I seemed most attracted to. I turned to look at the satin stuff. There was this one pink, ruffled party dress in a real nice satin, not much lace but a large pink bow across the middle. "Can I look at this?" I asked him. "Billy, it's probably your size, you can even put it on if you want." "No way!" "Way! All I ask is that you wear undies with it."
I was floored. Should I? I didn't even know this man but wow what an opportunity. I was buzzed with the beer (and, ahem...some other substance I won't identify). "Sure, I'd like to try it on, Alan, if that's ok, you sure?" Dumb me. He told me later that he was PRAYING that I would put it on! Alan turned and went to a big chest of drawers. "Just one thing, Billy. You can't wear YOUR undies with that dress." I turned and saw him getting something pink out of the drawer. He laid it on the bed, which I just noticed had a satin cover on it, in dark blue. A real thick quilted duvet. "Uh... what are those?" Alan held them up. "Bloomers, Billy. They go with that dress and if you want to try the dress on you will need these too. It's all part of the scene, man!" Alan offered to step out while I got dressed.
I sat on the bed, alone. At first I was hesitant to do it, but kept flashing back to the spankings I got from Cricket boy. As things progressed with him, to humiliate me more he made me put on his sister's things during the game. At first I hated the idea, then it "grew" on me (sorry). So I somewhat reluctantly pulled off my sweats and undershorts, and decided to "get dressed".