Exploring Possibilities Ch. 02byLaughingOne©
I was so turned on my my experience with the first man in the park, I quickly agreed when he suggested I place an ad to watch a stranger masturbate for me. Within an hour of placing the ad on Craigslist, it was flagged and removed (I still don't know why) but I already had more than fifty replies. I reposted the ad, and again it was removed, but not before I had about twenty more replies. Men, it seems, are more eager to reply to strangers, than women are. I was a little overwhelmed at first and I asked my first mystery lover to help me chose which men I should agree to meet. He did help, but a few that he picked were just too far away in distance to be realistic. A few got testy with me quickly when I didn't immediately respond (I had seventy people to reply to, and it took me a while). So between the few that never replied back, the few that were too far away, and the few that were struck from the list for being pushy or downright nasty, I had about twenty left to work with. Of those, if they sent a pic and just didn't appeal to me, I thanked them for replying but told them I didn't think they were what I was looking for. Eventually I made arrangements to meet three men, one an Indian, which, being a white girl and having mostly had white or black boyfriends, absolutely fascinated me, one a black man, and one a white fellow with interesting glasses.
Originally this one other man had replied to my posting, but he lives all the way in **** so I sorta brushed him off a little. An hour is a pretty long way to drive just to jack off for a stranger and I had plenty of other people replying to the post. He wrote back a while later that he couldn't get the idea out of his head, that he was so turned on by it, he was masturbating at home anyway, and he was really so excited, he'd be willing to make the drive to meet me after all. I was, in turn, extremely excited by his enthusiasm but we were having trouble figuring our schedules to make them mesh. Finally, at the last minute, we discovered we both had later that evening available so I sent him the address to the park where we met, and we set a time.
Anticipation kept me wet and ready all afternoon until finally it was time to meet. I drove to the park and waited... and waited... and waited. When I checked my email I saw not only had the poor guy gotten lost, but he had also gotten pulled over for speeding! Finally, about fifteen minutes past the time we'd set to meet, he pulled up in a little white pickup truck. Honestly, if I'd been through all those shenanigans to get to the park, I don't know that I'd have been in the mood to do much more than drink, but he got out of his truck with a smile. We shook hands but didn't introduce ourselves and he asked where we could do this. I asked him if he thought he could do it right there, at the cars and he replied with a sort of grunty kind of noise that seemed to mean no. He looked around at our surroundings, consisting of mostly soccer and baseball fields, but on the top of a little hill, there's a pavilion with bathrooms and a few picnic tables. Catching where his eyes were looking, I said, "Do you want to go up there?" He said yes, grabbed a messenger bag from his truck and we started to walk.
He was taller than me, by quite a bit, and was wearing a ball cap, dark long sleeved shirt, and tan colored shorts. He had a goatee but no mustache, and a very handsome face. His body reminded me of a friend of mine, someone I had desired greatly, who would never play with me because he was married and wanted to remain faithful to his wife. Anyway, that twinge of memory brought an even greater desire for him to me and I watched with hot eyes as he started pulling towels, lube and cigarettes from his bag. We talked a little bit while he rubbed his cock through his shorts. I was surprised to notice he was already hard. He further surprised me by shucking his shorts and sandals completely off before sitting on the table top. I was still standing with my hands in my pockets, trying to look cool and not totally shocked by his boldness.
He had a cock that every girl would want to have inside her, if she knows her body well enough. It was decently thick, about seven inches long, with a distinct head and a beautiful upward curve. When I saw it, I could only think about how it would stroke my Gspot while he thrust in and out of my body. He grabbed his lube, squirted a little on and started to rub himself while I watched from a little distance away. He asked me if I was gonna stand, so I sat. I asked him if I could touch him and he agreed. I slid closer, straddling the bench and started softly running my hands up the outsides of his thighs, down his calves, over his feet. Eventually I was brave enough to play with his balls a little. He was unshaven but his hair was so light, thin, and soft, it didn't matter. We talked a little while he stroked himself, and after a while, I took over.
His cock was very hard, maybe one of the hardest I've ever felt, and I loved the way the upward curve felt in my hand. At some point he lit up a cigarette and smoked a little while I continued to caress him. I remember asking him if he always smoked while he masturbated and he said yes. He ran his finger down the part of my breast that was exposed by my shirt and either I offered, or he asked, but either way, he pulled my top down a little to reveal my breasts to him. By this point, I had scooted pretty close. His leg was nestled nicely between my thighs, my hand was on his cock, the other on his ass. One of his hands was holding his cig, the other pinching and fondling my nipples. I was so turned on, I actually asked him if he wanted to have sex. He declined, saying he had a girlfriend and while he didn't feel guilty about what we were doing, he would if it went further. I accepted his answer but was extremely embarrassed I had even asked. It was so unlike me!
But my awkward question and embarrassment didn't ruin the mood for me, and it seemed it didn't really ruin it for him either. Eventually he pulled out this interesting looking masturbation toy. I'd never seen anything like it. It was a silicone tube looking thing, sort of light purple, but mostly clear with an opening on both sides. He slid his cock into it, added a little more lube and started sliding it up and down his cock. After a while I asked if I could try, and he let me for a while, but I could tell I wasn't experienced enough to really make it feel good and he took back control. We talked about how long he could last, how much time he had (I had a date later to have drinks with a friend), things like that.
He told me he wouldn't cum until I wanted him to, which a lot of guys have said that to me over the years but I find more often than not, it's not true. Excitement usually overcomes control and I hear a lot of apologies later. But for him, it was true. He would lie down on the table and stroke for a while, then sit up and play with my breasts and nipples, then lie back down. I played with his legs, balls and ass while he was laying down. He said he liked it when I played with his ass, but I always worry about my nails being too long and sharp to do more than softly run around a guy's anus. At one point he sat up and used his cock to tease my nipples and that developed into a quick titty fuck. I was excited by the idea of him cumming on my breasts but it didn't last long before he laid back on the table again.
Somewhere around his second cigarette, and the toy being used and discarded, used and discarded, he finally allowed himself to reach his peak. He was reclined on the table again and when he came, he shot his jizz high up on his shirt. I wanted to feel that hot creaminess on my hands so I put my hand on his cock and tried to get as much of his cum on me as I could. He came a lot, more than I expected, and I took a few seconds to savor the way it looked and felt on my hand before taking the towel from him and cleaning him up. I reluctantly wiped my hand clean as well and watched him as he dressed. We walked back to our vehicles together, hugged and said good bye. When I looked at the clock in my car, we'd be out there a solid fifty minutes. I could only think of how many times I might have cum on that luscious cock of his if I could have fucked him for fifty minutes...
He emailed me yesterday and asked if I had any girl friends who would want to watch as well. I don't but I told him if he ever wanted me as a second, I was SO into it. Oh, and he managed to make it home without getting stopped by the police again.