The 65-year-old cock punisher

My mom 65-year-old friend that basically used me as her little play toy, the story of how it all started

My mom’s had a 65 year-old friend who was a flight attendant for her whole career. I always would take care of things at her house when she was out of town. She was a woman that was kind of old-fashioned, mostly wore thigh highs, or a garter with nylons. She had a few pair of pantyhose and a ton of sexy panties. Whenever I could I would always try to jerk off with her nylons. She had a picture book she made for her husband who was a pilot that had passed away of herself in sexy lingerie and in those nylons. When I helped her box up a bunch of his stuff to go to storage I made sure that album didn’t and I used to keep it hidden in her house so whenever I had the chance I would look at them and jerk off with either a pair of her panties, her nylons or the rarity a pair of her pantyhose. One week I was going over to take care of her house as usual. I went upstairs into her room found a nice pair of nylons slipped them over my dick and started jerking off with them. While I was jerking off her closet door was open and I could see a really sexy stiletto heel. I got up, grabbed her heels and put them on the bed and started licking them and sniffing them on the inside. Hadn’t really did this too many times, but man was it hot, I could still smell her feet and lotion she would use in the heel. I started jerking off harder and faster when I heard a voice say “I always knew you did this with my panties and my hosiery but never my heels !” I quickly stood up, turned around, and there she was standing in the doorway, pulling a suitcase, still in her flight attendant uniform. I stood there like a deer in the headlights hand grip to my dick with her nylon still on it standing next to a pair of her heels on the bed. I started to tell her sorry when she told me to stop and told me to sit down on her bed. I sat down, pulled nylon off and laid them on the bed. She asked me if I did this because I had an obsession for Women’s intimate, specifically panties and hosiery or was it specifically because she was wearing them? I told her it was a little bit of both, but she was really hot in them for someone her age. She sat there seem to accept the answers, and I told her that I would leave and that I wouldn’t come back and please don’t tell me. She assured me that she wasn’t gonna say anything and that I can continue doing what I do. I asked her like watching the house and she told me no she said I could use her panties and hosiery just the dirty ones. I said really, and she replied yes but I want you to finish in the pair of nylons you had on your dick. I was confused and said what. She told me again put the nylons back on your dick and finish jerking off. I want to see it. I sat there for a second and she picked up the nylon and handed it to me and said here I’m serious. So I slid the nylon back on my dick and started jerking off. She told me to look at her. As I looked at her, she lifted her screwed up, revealing she had a girdle on with a beautiful pair of black nylons. I could see if she was wearing sensible heels, but still looked hot in them, especially now that I could see her panties, her girdle and her nylons. She told me I could get on my knees and touch them which I properly did. She told me to jerk off faster and to make sure I let out a nice load in them. I asked her if I could kiss her legs while I did it and she said OK but not to let my facial hair snag too much on her nylons. I told her yes ma’am, and started kissing her legs vigorously masturbating while I rubbed the back calfs with my other hand . It wasn’t long before I told her I was getting ready to come. She told me to stand up, which I did and she she grabbed one of the heels off the bed and with the other hand immediately cupped and squeezed my balls a bit. She held the heel up to my dick and told me to cum as hard as I could in her nylons. She started massaging my balls while I kept . I told her I couldn’t stand it anymore I needed to cum. She stuck the heel over my dick AndI just shot load after a load into her nylons that were on my dick shoved into her heel. I came so much that I drenched the nylon and leaked out into her heel. I was done. I looked at her and she asked me if I had always wanted to do something like that and I told her absolutely. She immediately took her hand off my balls, grabbed the nylon and slowly pulled it off my dick. She told me to take the other matching nylon home with me and return it just as nasty as the ones she had in her hand. I said OK and left the house. After that incident, we started doing more things. It started out slowly at first, but gradually did more as I went into college. But those are stories for another day.