Masturbation scavenger hunt

One summer in college I went to live with my grandparents. I told my previous boyfriend (who I still on occasion fooled around with) that I was worried it would be a sexually frustrating summer. I happened to be very wrong about that prediction, but out of the kindness of his heart, and enjoyment of getting to have a hand in my sexual exploits, he made a game for me. The game consisted of 13 different places or ways I was to masturbate. If successfully able to accomplish 10 of them, he would give me a prize.

That summer ended up being filled with wild sex on the beach, in cars, bedrooms, hot-tubs and pools. I actually barely having time to cross off items on the list, what with my 8-10 hours of anatomy class in the daytime and my "anatomy classes" at night. I don't think I can recall all of the details about what each task entailed, but there certainly were some memorable ones.

I think the first item that I was able to accomplish was masturbating while driving. I'd never thought of doing it before, but quickly found it to be a pleasurable distraction while I was stopped at red lights. For the first time I was begging the lights to stay red just a little longer.

It wasn't long before I figured out how to cross off another item on the list - masturbating in class. Our chairs were barstool style and at the beginning of a test I placed an eraser on the chair, under my crotch and slowly rocked on it. This did not help my speed with completing the test, but it did make it more enjoyable.

Scanning the list of options, I remember thinking that the idea of using a non-sexual object for masturbating sounded like a good challenge. Sure I'd heard of vegetables for that purpose, but what if my grandma saw me sneaking my used cucumber out of the house, to the garbage and asked if she could put it in the salad that night. I decided against food. I grabbed 6 pencils from my backpack and put them inside a condom. It actually felt pretty good after being on a sex hiatus for about 4 months.

That break from sex was soon to end though and with it I was able to check off another item - masturbating with another person present. I rekindled a friendship with a childhood buddy during that summer and one night we went out for a drive to the coast. As we sat in his truck overlooking the moonlight ocean, sexual tension that had been building peaked and our lips met. Our hands eagerly groped. When his fingers started moving down my pants, I stopped him and said "let me show you what I like."

I unzipped my pants, interlaced our fingers and started playing with myself. It wasn't long before his fingers joined in. We took turns me leading with the tempo, position and pressure and him continuing when my fingers got tired. It was the easiest times I've ever had reaching orgasm with external digital stimulation alone.

The final memorable task was public masturbation to orgasm. I interpreted this to mean anywhere where someone might see me. And sure I'd done that already, but I tried to think of somewhere that would be somewhat embarrassing if I were caught. I decided on the bench on my grandparents' front porch. I sat there with a book on my lap and put one hand down my pants. Not more than a few minutes after starting the mailman walked up to deliver the mail on the porch. I stopped, said hi, fairly certain he hadn't seen anything. After he left I went back to the task and reached orgasm before anyone else came up to the porch, though several people did walk by on the sidewalk on both sides of the street. I'm pretty sure it would have been hard to tell what I was doing.

After completing items on the list and recounting the incidents to my ex-boyfriend he gave me the prize - a lovely CD (OK by Talvin Singh) that I still have and listen to from time to time.