Went to a video porn store wearing my panties and bra under my clothes and met a guy in the booth that was into spanking and he spanked me good. First with his hand and then his belt. It felt great in my satin panties.
Since then (below) I've really got into being spanked and caned while wearing my sissy clothes, and have now found a trustworthy fellow cross-dresser who enjoys doing it to me.
I'd put this ad in spankingcontacts.co.uk a while ago: "Mature and unconvincing crossdresser seeks gentle non-marking daytime (Mondays or Thursdays) spanking from friendly male, anywhere in London, as punishment for some very naughty thoughts which you may force me to tell you about." Got a reply from XX to say that, although he was a hetero spanker he was interested in meeting. We met for a drink and agreed on our scenario. I was to be a teenage boy at a boarding school, caught dressed up in matron's underwear in her bedroom and masturbating by him, the gym teacher. Over the knee spanking, first on pantied bottom, then on bare bottom, then bent over a chair. Agreed to meet again at his house.
I arrived at the station with a small bag containing a black bra, black camisole, black see-through nylon panties - French knickers, black lace-topped nylons, and a lacy blue suspender belt. Walked back to his house.
He showed me to his upstairs bedroom, and I drew the curtains. Old-fashioned room, with a mirrored dresser by the window. Another mirror angled to reflect that so that he could sit on a chair outside in the landing and watch me. An open box of tissues. I spread out my frillies on the dresser and he went out and put on shorts. I pretended to discover matron's bra and camisole, said to myself "I wonder what I'd look like in these", took off my t-shirt and put them on. Pulled off my trousers and pants, showing him my erect circumcised penis, and put on first the suspender belt, then the stockings (bending down to give him a good view of my buttocks and anus). Started to rub myself through the panties. I could see him in the mirror, pulling back the leg of his shorts and rubbing himself. Also circumcised.
He came in suddenly, asking me what I was doing. I hung my head and said "nothing, sir." He shouted "you dirty little boy, you're wearing matron's clothes and masturbating. You deserve a spanking". With that, he pushed me down over his knee and started to spank me - hard! - with his right hand on my pantied bottom.
After a few minutes he dragged me upright and pulled my panties off, then down on his knee again and more spanking, this time even harder. I could feel his erection against my stomach, and I'm sure he could feel mine against his thigh. He dragged me upright again, and then made me bend over a chair, with my hands on the seat. He pressed himself against me, still spanking me, and after another couple of minutes took of his shorts. I wriggled so that his erection was in my bottom crack but he wouldn't push any further even though I could feel he was oozing pre-cum. (By this point my panties and suspender belt had been ripped off me, and I was wearing only bra, camisole and stockings. He was dressed only in a t-shirt.) All the while I was "crying" and pleading with him not to hit me.
I whimpered, and asked "would you like me to suck your penis, sir?" "No, but I'll suck yours, boy", which he did. After a short time I sat down on the chair and he pushed his penis into my mouth and started thrusting, nearly suffocating me. I was very excited by this time, and I knelt down between his legs and took his penis into my mouth, stroking it with my left hand, and masturbating myself vigorously with my right. I could taste his pre-cum, and I very quickly came to orgasm, ejaculating in several copious spurts all over his feet and the carpet.
i have been spanked many, many times in panties (and fully dressed en femme)and i just love it! It makes me feel SO submissive and feminine to lower myself across a womanly lap and have my skirt slowly lifted. It makes me squirm just thinking about it!