oldest or youngest person you have masturbated with

[ilovetojilloff]

Oldest 40

youngest 17(i was also 17 at the time.)

[Ready_Lube]

youngest would have to be 19 when I was 18

Oldest would have to 33 when I was 20

[brnsinger]

The youngest i have masturbated with was when i was in my teens with a 14 yo (Same age as me at the time) and the oldest was recently with a 76yo neighbour and his wife

[Bellend]

youngest....early teens with a female cousin (she was a year younger).
oldest.... 37 y.o. guy. was 18 at the time.

[meagain]

youngest would be 14 when I was 14, it was the first time for both of us...oldest would be with a 58 year old women when i was 17...she jerked me off and then I rubbed her pussy until she came...i got hard again and she sucked me a little while it touched hear breasts..i finally came on her...then once a could of years later we did it again..only this time we screwed...

[FaceJacker]

The youngest... not sure I should post the age (what are the rules about that?!). It was the second time I had ever masturbated and she was a year younger than me, so that should give you some idea. But she wasn't actually masturbating, just observing, so not sure if that counts, although we did masturbate together when we were a little older.

Oldest... The only time I masturbated with someone significantly older than me was when I was in college, but she was only in her early 40s so not that big of a deal.

[jamiegirl]

Youngest....18
Oldest.....45

[hrnygrl2289]

Youngest 12 (when I was 12)

Oldest 29 (I'm 19)

[happystroker]

Well, in years only, my first buddy was when we were both ten. When I was sixteen I regularly had sex with a couple in their middle forties, thirty years older.

When I was just out of college, I masturbated with a man in the apartment, and he was in his late sixties, forty years older. I found it very erotic and I've had my eyes open since, but didn't discover anyone. Then a few years ago, I visited and "interviewed" some clients at their house (I'm an architect) to get to know them. They were in their late seventies and it turned out were totally into masturbation and very turned on by oral. We bonded that night! He was an incredible artist with his hands and tongue!

I frequently have interns who work with me, both men and women, and have enjoyed playing with a few of them. The youngest was a very pretty boyish blonde girl of twenty-two when I was forty-two. On a long drive home at night, in the darkened car, we talked about sex. She was pretty inexperienced, with only one boyfriend she didn't go far with, and two girlfriends. She asked lots of questions that finally I said I could best answer by showing! We went back to the office and I masturbated for a couple of hours. She lives with another girl now, but she really liked jacking me off, and I'm in love with her small, perfect breasts and pink nipples. So she comes by now and then, when her partner is on a trip, gets bare-breasted (or more), and gives me a hand-job.

I love to masturbate with other guys, and there are a couple of gay guys who belong to an informal professional group that meets at our office. They jokingly flirted with me and more and more I wanted to get naked with them, though I was worried because they're not very "discrete". One night after the meeting I went out with them to a gay bar, and ended up fessing up to my desires, which they were very happy to fulfill. We went back to their place and jacked off together. The youngest was seventeen. This got to be a regular thing after our meetings. One of the women who comes seemed suspicious, and I mentioned it to them, and that I was worried about my 'reputation'. They laughed and said that her hubby was a bisexual cross-dresser, so I shouldn't worry!