One of my favorite masturbation stories is from 24 years ago when I was 14. I had no sexual experience whatsoever, had never even kissed a girl. But my buddy Rob was quite successful with the girls. He had gone steady with several and always delighted me and my buddies with tales of his exploits. He would finger-fuck these girls and then tell us about what they looked like naked, how their pussies felt, how many fingers he could get inside. Every time he told me one of these stories I would go home and jack off on the toilet seat thinking about him plunging his fingers inside some sweet young girl's pussy. And I would get a hard-on every time I crossed paths with one of his conquests.
One time he was going out with Elaine, a dark-haired beauty with olive skin who was one year older than us. He apparently had carte blanche with her pussy and I must have jerked off a hundred times picturing her naked and spread-eagled.
One day he invited me to come with him to Elaine's house to smoke a couple of joints. She lived with her dad and younger brother, who obviously weren't home. We went in the garage and smoked the joints and then went inside to watch TV. After a few minutes I could tell they were getting horny as their hands were all over each other. They excused themselves and went upstairs to Elaine's room, leaving me with the biggest boner I ever had. I started to feel sorry for myself and was so horny thinking about what Rob was doing to Elaine in the room. I decided to go to the bathroom to jack off. As I stood there stroking his cock, I noticed a laundry hamper with a bra sticking out of it. I opened it and saw it was Elaine's dirty laundry. I hit the mother lode: bras, panties, nighties, even some nylons. I grabbed one of her panties, put it to my nose and sniffed the crotch while I rubbed my cock. Then I rubbed my dick with her panties. I nearly shot my load but held off. But when I took her pantyhose and massaged my boner with them I lost control. I felt SOOOO! good, I shot several gobs of cum all over her nylons. I immediately panicked and thought about stuffing them in my pants and beating a hasty retreat. Then a strange feeling came over me. After I wiped my dick with her pantyhose, I placed them back in the hamper and left. For some reason, I wanted her to know that I had jacked off with her underclothes.
Here's the funny part: A week or so later, my buddy tells me Elaine thinks her brother has been jacking off with her undergarments because a pair of her nylons had what appeared to be dried cum on them. The poor little bastard must have took the rap for me.