Have any of you ever been caught masturbating by an authority figure, such as a teacher, coach, priest, or boss? If so, describe what happened. Was about 19 (long time ago!) and my family belonged to a swim club. They had these cabanas we rented for the season and shared with my friend's family. We...

Thanks for the responses, everyone! Wanklover: I, too, fucked my bed the same way with lotion or hair conditioner in a baggie up through high school. Mash2014: I remember the first time I heard my friends having sex in the next room just the other side of the wall; I came with her. Duke2000: Prince...

M or F? M Age? 61 First time you masturbated away from home? 15, on vacation in Florida First time you masturbated twice in a row? I was about 14 First time you masturbated together with someone? Never have First time you masturbated in presence of someone who was not masturbating? I was about 25. I...

I thought about bringing it back after I was done the first time for that very reason. Didn't want to push my luck though. It was a white bra so there was quite an obvious stain! LOL

From my early teens (over 40 years ago) I had a real thing for my best friend's mom. Beautiful woman with a great body. She often showed plenty of cleavage. Used to love laying in my room and stroking while thinking about her tits. Our families were very close and one day I go to their house to see ...

Going back a ways but here are some from the 1970's back in my teens:

Wonder Woman
Policewoman
Maude (when Adrienne Barbeau was on)
Charlie's Angels

Another point is with internet you find out your fantasy or kink isn't so unusual. When I was growing up I had a real thing for my best friend's mom. I fantasized about her in countless sexual ways and can't even begin to estimate how many times I masturbated thinking about her. Almost always I felt...

I fall in the "older" category now but when I was your age I found myself doing the same thing as far as older women are concerned even though I was totally in love with my wife and still am. One woman I often fantasized about was my best friend's mom. I actually told my wife and she was c...

Masturbation has been a taboo subject for most of the time. Most people tend to hide the fact they masturbate. When I was growing up, masturbation was something you didn't speak about and you hid the fact you did it. Men would be considered as if they were unable of having switch women. Women were ...

I imagine being back in my teens a (long time ago) and seeing my friend's mom wrestling against my neighbor from across the street. They start out in bra and panties but my neighbor quickly takes control and dominates my friend's mom. Stripping her naked and then straddling her face and make my frie...

Since I was in my teens (over 40 years ago) my go to has always been my best friend's mom. Over the years it has varied. Fantasized about her wrestling other women with her opponent dominating her and making her pleasure her at the end. I would say though that the one consistent and favorite fantasy...

Though I was reluctant to do so I shared my hidden fantasies with my wife about 6 months before we got married. I was hesitant because they mostly involved my best friend's mom and I knew this was someone who we would be seeing on occasion. The fantasies are varied and don't want to bore everyone wi...

I was at my best friend's house. I had a real thing for his mom and her 36D breasts. So she's there and she has on this light purple button down top with a few buttons unbuttoned. I saw that cleavage and I just couldn't help myself. So I say I have to go to the bathroom. Went in there and rubbed one...

As a teenager, how easily I got a boner. And how difficult to hide it at times. I hear you. In my teens I had real thing for my best friend's mom. Every time I saw her I'd get a bone and I know, especially during the summer while wearing shorts, it was hard to hide. Also, we belonged to the same sw...

I

1. What age did you start masturbating and for how many years have you been masturbating? About 11. Over 45 years. 2. How often do you masturbate? Few times a week. 3. How long are your typical sessions? Couple hours. 4. When did you last masturbate? Two days ago 5. When and Where do you usually mas...

I know a lot of us who are older utilized the Sears catalog in our youth. However I haven't seen anyone ever mention the old breast enhancement ads from back in the 70's. My mom used to get Cosmo back then and those ads were one of the first things I stroked too. Just curious if anyone else did.

Sitting on the floor in my room. I was about 11. Was looking at my mom's Cosmo magazine. In the back they had the ads for breast enhancements. There was one with Betty Weider in a leopard bikini that I was stroking too. All of a sudden all this clear stuff comes out of my dick. Scared the heck out o...

When I was younger I had many fantasies about my friend's mom. One in particular was by far my favorite. It involved her, myself and one of my neighbor's, a woman a couple years younger than my friend's mom. The two of them agree to let me watch them wrestle one another in a hotel suite. My friend's...

Oh yeah. I'm in my late fifties and I have very fond memories of the Sears catalog. JC Penney also. Always have been a boob guy and that always did the trick.