Exploring Possibilities

Story Info
My first encounter with a stranger.
868 words
3.67
29.4k
1
0

Part 1 of the 2 part series

Updated 09/22/2022
Created 07/31/2010
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I went on Craigslist this morning to repost my ad searching for another woman to experiment with and I started browsing. I came across a posting from a man who was looking for a woman to watch him masturbate in a park. Although I'm not usually so bold, I quickly replied to the man and we exchanged a few emails. It turned out he was very near the same area where I happened to be, and we were both free at the same time and so it was decided we would meet. He named a quiet little park and told me what kind of vehicle he was driving so I would know when I saw him that he was the man I was looking for. It wasn't until I arrived at the park that it occurred to me I should probably let someone know where I was and so I contacted my friend, without telling him what I was doing, and asked him to check up on me within the hour.

Soon after I parked, a freaking hot, black convertible pulled up next to me. I looked over to see a very good looking man wearing sunglasses and a nervous smile. Neither of us had done anything like this before and so I'm sure I returned his nervous smile with one of my own. I climbed out of my vehicle and leaned against it while he remained seated and started to stroke himself through his shorts. We talked a little about why he placed the ad and why I answered it, but honestly, I was so excited and nervous by the idea that I was about to see a complete stranger's cock, I don't remember a word he said, except he said he wasn't sure he could get hard, he was so nervous.

He pulled his zipper down and unbuttoned his shorts. His cock was limp still but he was shaky so I knew he was excited and scared. It started to grow before my eyes and damn if that wasn't one of the most beautiful cocks I've ever seen. He was thick! And I bet when he gets totally hard he's a good 8 inches or more. He's circumcised and the head had a nice purplish color. And damn the man had a huge slit! I watched him lightly stroke himself with his fingers, and grasp and squeeze the base of his cock with his hand.

One of the things I tried to be clear about before we met, was that I was there to watch only and not interact but, once I saw him and that mouthwatering cock, I wanted to climb into the passenger seat of his sweet ride and taste him. He looked at me and breathily asked if all I wanted to do was watch. I was a little surprised so I asked, "You'll let me touch?" I know all the blood drained out of my head and straight to my clit because I was breathless and dizzy as I walked around the back of his little sports car and around to the driver's side before reaching in to gently stroke him. His skin was soft and I could see he was shaved and commando. It wasn't long after I touched him that he told me he was close to cumming. He asked me if I wanted him to finish and I thought maybe he wanted to do it himself, so I reluctantly slid my hand down to fondle and stroke his balls while he took himself in hand.

He stroked himself a few times more before his breathing got heavy and his jizz burst from his body in one big spurt, like a volcano. I couldn't tell if he spasmed more or only that one time, but it was a lot of delicious looking cum spread over the head of his cock and down his hand. He laughingly, somewhat shakily searched his pockets for a paper towel, cleaned himself up and we both smiled and gave nervous laughs. I don't remember what was said next, I was so excited and turned on by what had just happened. I walked around the back of his convertible again and climbed in my vehicle. I noticed I felt shaky and excited so I turned back to him and asked him if he felt like he could drive. He said he could and we agreed to be in contact with one another.

I drove to the nearest fast food place and bought a soda to help calm down and cool off before heading home to my children and soon after my phone vibrated with the notification of an email. It was him, thanking me and telling me how much he'd enjoyed what had happened... and teasing me about how I was not going to participate, only watch, but ended up touching and stroking him. He asked me if I would be willing to meet him again, for different naughty fun and I agreed. He's away on business now, but I anxiously await the time he returns and I can play with that lovely body of his with my hands, and hopefully mouth...

To be continued?

Please rate this story
The author would appreciate your feedback.
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Milking My Man, a Guide for Women How and why I milk my husband's sperm.in How To
Mark Gets Milked Friend's hot mom drains him.in Fetish
The Masturbatrix Ch. 01 Amy likes to make guys cum . . . a lot.in BDSM
Saga of a Chronic Masturbator Recollection of how I spent the 2020 Covid pandemic.in Toys & Masturbation
I Love a Handjob A journey through my past exploring my love of handjobs.in Fetish
More Stories