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She said this is the first time she has “socialized” with any group involving men in ten years. Well Susan and I hit it off and we began spending a lot of time together. Still after a month I was not getting laid, not even a blow job. One night I “broached” the subject and Susan bowed her head and began crying. She blurted out “I haven’t been with a man in ten years, I’m scared, and I just don’t know what to do with a man anymore”. Well I’m not a jerk, I really liked her and I told her take her time. After all I can screw any one of five different women every other night. All I got to do is call a GILF and say “come over” and these old sluts will be in my driveway in ten minutes with a condom and lube in their purse. Well the next night the Singles Group was having a dinner and dancing event at a nice hotel in town. I went to pick Susan up and knocked on her front door. As I kind of expected Susan answered the door in long white silk robe, white thigh high nylons with full make-up,. I think a previous girlfriend had bought them for me when it was all the rage for guys to be in skinny trousers, it was one of the death knells of that relationship as there was no way I would have worn them, but now they might really help present me in the right way.Pulling the top over my head and down over my chest, the padded bra did a good job of making me look like I had something there, although it wasn’t much. And when I pulled up the jeans I was surprised at how well they fit. They were tight but not uncomfortably so, and very snug around my ass, I did have to re-arrange my junk a little in the panties as the jeans needed to be pulled up quite high to avoid being too misshapen around the crotch.I applied some simple makeup and mascara, put on my mask and grabbed a bag to leave. I was nervous about stepping out and looking like a girl, but I knew with the mask on it would act as my shield. It hid my face shape and with only made up eyes peeking out over the top, I couldn’t.
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