A few years ago (I was in college) a close female friend asked if I would take her and her friend to a pool in a nearby town so they could take their lifeguard certification class and test. It would take a few hours and we could stop for a few drinks on the way home. I had nothing better to do, and liked hanging out with Nicole, so I said sure. Nicole is cute - a petite blonde, flat tummy, great ass and nice breasts. Her friend Kathy, though, was fabulous - blue-eyed blond, great tan, great body and very friendly. When we picked Kathy up, I fell in love. She was wearing short, faded cutoff jean shorts and a blue hooded sorority sweatshirt over her swimsuit. As drove, she peeled her hoodie off to reveal her little two-piece top and her great body. I dropped them off, watched (with what was by now a tremendous hard-on) them walk into the building, and promised I'd be back at the appointed hour. I was so horny, I really wanted some relief. I drove around for a while, but my horniness only got more intense. I stopped in an empty picnic area in a nearly local park. I was wearing loose, heavy sweatpants and a T-shirt, and I started to massage my hard cock through my sweatpants (no underwear). That felt great, and pretty soon I wanted to reposition myself and get more skin contact. Kathy had left her hoodie in the car, so I covered my cock with it and started to stroke. Her sweatshirt was real nubbie and soft inside and it felt fabulous. The thought that she wore it against those magnificant breasts made me even more excited. Needless to say, the more I stroked, the more I wanted to explode. But I didn't want to make a mess, and I didn't want to stop rubbing my cock with her sweatshirt. I knew if I came into her shirt, she would feel (or see) it when she put it on...and there would be no doubt where it came from. I was getting too close too fast, and didn't want to stop. Then I saw it - Kathy had cut the neckline of her hoodie to kind of open it up in front, and there was an opening on each side - near the drawstring - that might be just big enough to slide my shaft into the hood. The hood was smooth cotton on the inside (the part that would go next to her face) and the outside, and fleecy in between. I gently inserted my rock hard cock into the hole in the hood of Kathy's sweatshirt, and kept pulling the fabric down my shaft so that my head was deep into the fabric. It felt great - the hole was barely wide enough, so there was great friction on the base of my cock, and the fleece felt great on me, with the balled-up sweatshirt in my lap. I exploded in a few more strokes (I really wanted it to last) - and it was mess-free! I put myself together, put her sweatshirt near an open window so it would dry out before I picked them up, and drove off. When I did pick them up, it had gotten cooler and Kathy immediately took her sweatshirt, went into the locker room to remove her wet swimsuit and came out wearing her hoodie and cutoffs - with no idea what had gone on. The thought of her bare under her hoodie excited me even more, and I was ready for another round.
Another time, perhaps.