"What's the most daring place you ever masturbated?"
Shannon and I had only been dating for three weeks but we already knew that we were both liked to talk frankly about sex, so this sudden turn in the conversation wasn't too surprising coming from her. We had just finished mutual backrubs and now were facing each other on the floor, lying in opposite directions and propped upon on our elbows, fondling each other lightly with our free hands. She gazed directly at me in her usual manner, showing both insatiable curiosity and a caring reassurance that whatever I said was OK with her.
I thought of a few spots, but quickly settled on my answer. "Well, several places actually...swing sets."
"Swing sets?" She seems compassionately amused.
"Yeah, it started with the one at the elementary school on 8th Street...."
She suddenly interrupted. "Wait, you did that in elementary school?"
"No no no, this was much later, at 18, it was summer and school was out, and this was near my house so I occasionally went there to swing and remember what it was like to be a kid. OK, so this one time I'm sitting down in my terry cloth shorts and realized how hot the seat was--I'm talking about the black rubber seats, we used to call them 'butt squeezers' because, you know...."
"They squeeze your butt when you sit in them," she finished for me, assuring me of her common experience.
"Right, so anyway, it was hot sitting in the sun, and I wondered what it would feel like if I touched it with my penis. The swings were in the corner of the lot, behind me was an alley behind a fence and some trees, and it was the middle of the day, so I was pretty sure I couldn't be seen easily from the back unless someone came up close, and I had a good view ahead of me of the rest of the small playground and the school, which was completely deserted. So I slipped it out the side and touched the seat and it was like wow, this feels really hot, and I got hard really quick." Shannon nodded, encouraging me to go on.
"I figured out that I could get more contact if I leaned forward so I could slip my penis between my pelvis and the seat, so it was rubbing along the top of my penis, and I could slide it slightly back and forth as I swung. Just the tip of the head was sticking out behind me, but I didn't think anyone could see that unless they got really close. It still probably looked suspicious because I couldn't swing very high, I was just sitting on it leaning forward and swinging a foot or two back and forth, I couldn't kick my legs back and forth much because I was sitting on my dick and balls, which was a pretty delicate situation."
Shannon's eyes gleamed with interest. "So did you cum?"
"Not the first time, but I came back several times and eventually learned to cum that way, although it was pretty messy since the head was sitting right under my shorts so I got a big stain right under my butt. It felt great though, so I did that a few times. Then later I figured out that I could sit farther back into the seat so my penis and balls were hanging free out the back, but were still pinched a bit by the seat. There wasn't as much contact, but it was really exciting, as well as scary, to feeling them swinging through the air, and this way I could also swing my legs almost normally."
"Did anyone ever see you?"
"I don't think so, but once I did that in the late afternoon and after a while I heard this car on the street on my left, I turned to look as I always did just to make sure no one was coming close enough to see--and suddenly this car turned into the alley and slowed down to turn into the garage of the house right behind me. And then I realized I didn't have any plan for what to do if anyone came close, except maybe to jump off, but I didn't do that. There was an older lady in the car and we saw each other, her window was down and she said hi or something."
"But she didn't see your dick?" She seemed incredulous.
"I don't think so, remember there were a lot of trees and bushes still, so while she could see I was on the swing I doubt she could pick up on the details unless she was really trying, and she was still moving. Still, I was really scared and said hi back, but just tensed up and stopped kicking my legs, I just held them forward and let the momentum move me back and forth, and suddenly after two more high swings going back I felt the cum pulsing out of me totally out of control, I couldn't see it of course but knew it was just flying into the air and onto the ground, and if that woman came out of her garage and looked at me she could see it, but the door shut and when I turned my head it looked like she just went right into the house. But I didn't go back there much after that."
"Wow, so did you ever do that again?"
"Yeah, occasionally I tried a few other swings if they were isolated enough, or really late at night, but I don't think I've done that since I was 20 or so."
She thought for a minute, then said "I'd like to watch you do that."
"Really?" I knew she was open to trying new things but this was a little kinky.
"Yeah. Would you do it for me?"