Masturbating to People You Know

[iammmd55]

Do people you know play a role in your masturbation fantasies?

At I3: Because rules and, that’s when I first began to fantasize.

My first fantasies were of my junior high crush. Before I’d just been concentrating on the pleasure. After seeing her in a leotard doing a gymnastics routine one day, masturbating that night was a whole new experience. I’d had a crush on her since 3rd grade, but it was only after I’d been masturbating for some time and then that gymnastics show that I’d thought of HER - or anyone - while “doing’ it.” And I was hooked! At the end of the year seeing her in a sleek one-piece swimsuit I added another version of her to my nascent spank bank.

Funny thing is, I never thought of doing anything sexually with her in these fantasies, just marveled at the memory of how she looked in that leotard and swimsuit. And her face, of course. A couple of my friends had crushes on her as well (I really now think SO MANY guys back then did) and admitted to masturbating to her, too, but I never asked them about exactly what they were imagining. We would just say like “i did it to —— again / last night / in the shower” finding, I think some comfort in our shared longing.

I did have another girl I began masturbating to that year, the 16-year-old sister of a friend. She was cute, attractive to me, but not beautiful. She was also a swimmer and a skier and had, what I thought, to be a fantastic body. We lived in the same neighborhood and I saw my friend & her frequently. One day my friend & i came into his house and I guess she didn’t know I was with him and she was just coming out of the bathroom after a shower as we entered the hall. She was standing side on to us just holding her towel before turning down the hall to her bedroom. We startled her and she said “Oh!” and then just turned and walked down the hall to her room. So I got maybe a 2 second side view of her slender body and small perky breasts and then a 4 second or so view of long legs, bare back, and tight, perfect butt. She was deeply tanned where her bathing suit hadn’t covered her and ass, pale & lovely, seemed to glow as she’d walked down the hall.

She’d never made any effort to cover herself and I guessed, after thinking about it later, but never asked my friend, that she just didn’t care if he saw her nude. I’d blurted out, quietly I’d hoped, when we went into his room “wow, —— is beautiful!” and he was just like “Yeah…,” but didn’t say anything else, and I didn’t either because I was suddenly concerned about how to hide the erection that I suddenly realized was tenting my shorts. We got the tools for the bike and left.

In bed that night as I got into masturbating I lasted only a little longer than my 5 -6 second viewing of ——‘s perfect, naked body earlier that day but not by much and came in the middle of only the third or fourth in-my-mind replay of her standing there then turning and walking down the hall.

A few days later when I saw my friend after school he point-blank asked me if I was jerking - off to his sister. I didn’t see any reason to lie, and knew he’d know I was lying, so I just said “Yeah.” I thought he was going to say “that’s gross!” or “please don’t” but he didn’t say anything. I didn’t have the guts to (or maybe without realizing it, I had enough sense not to) ask him if HE jerked off to her.

I didn’t see his sister for a couple weeks after that and my fantasies (if you can call a minds-eye replay or imagined scene measured in seconds rather than minutes a “fantasy”) were now culminating in a completely imagined view of her full-frontal nude. When I did see her in the driveway as she was on her way out as I was headed into their house one Saturday afternoon, I stopped and immediately apologized for catching her coming out of the shower that day, because I thought it was the right thing to do. She said not to worry about it.

That should have been the end of it. But I got kinda nervous and stupid and told her that she had a great figure and looked fantastic, getting a bit tongue-tied in the process. I mean, that’s actually the word I used “fantastic.” She smiled and said “thanks” and just kept staring at me. I didn’t know what to say then but neither of us was ending the conversation and she was just standing there with the car door open and I was trying not to think of her naked and suddenly thought maybe I should apologize for that, too because I shouldn’t have seen that.

But I wasn’t thinking of apologizing for what I was doing when I was thinking of her nude because apparently I just wasn’t thinking.

“It’s kinda hard now not to think of you nude.”
She didn’t say anything for a couple seconds.

“Ohhh… “ Then she looked like she was deep in thought. “You mean when you masturbate?”
She gave me a little smirk. I wasn’t sure how to respond and I guess suddenly looked a little uncomfortable.
“Yeah.”
“Well, that’s OK.” She smiled.
“Are you sure? Because I won’t do it to you if you don’t want me to.”
She kind of giggled. “You’re sweet. No, it’s fine if you want to think about me.”
“I don’t think about doing anything with you, I mean like having sex.”
“You don’t?”
“No. I know we’re not going to do that.”
“I haven’t had sex with anyone, yet.”
“Yeah, me neither.”
“OK well, what do you think about?”
“Just what you looked like nude… and in a bathing suit.”
“Really? That’s all?”
“Yeah. Well, I imagine what you’d look like nude from the front, too, but I never saw that.”
“And is that what makes you cum, imagining seeing all of me naked?”
“Oh, yeah!” I think I said that with a bit more enthusiasm than I should have and realized that just having the conversation with her was turning me on.

…

[wanklover]

I don't really fantasise nowadays but when in my teens my best friend had a gorgeous older sister who I would fantasise about when I wanked. I used to imagine what it would be like to stick my hard cock into her pussy and cum inside her or for her to be wanking me off. Now i'm old and have no sex life with my wife anymore I do sometimes think about her and a couple of other girl's I fancied when young.

[iammmd55]

I too definitely fantasized more when younger & single. Late 50’s now, it’s more a physical activity where I’m focused on the sensations.

Several friends’ sisters were entered into my spank bank over the years. Maybe oddly, I don’t think it was until my college years that I actually fantasized about fucking them rather than just about how attractive they were.

Curious, did your friend know you spanked it to his sister?

[mash2014]

Since I started masturbating at age 12, I have masturbated mostly thinking of girls I had crushes. Then I moved into women I didn’t know but I thought were hot. Nowadays, masturbate thinking of women I know, some crushes, others I think are hit, sexy. There is one who most of the times when she wears skirts I've seen her panties. She's not careful.

[mash2014]

I too definitely fantasized more when younger & single. Late 50’s now, it’s more a physical activity where I’m focused on the sensations.

Several friends’ sisters were entered into my spank bank over the years. Maybe oddly, I don’t think it was until my college years that I actually fantasized about fucking them rather than just about how attractive they were.

Curious, did your friend know you spanked it his sister?

One day I had been doing drugs, and I let my friend know that I masturbated thinking of his sister. Later, I felt weird about it. After that day he never made any comment about it.

[rathb69]

Definitely have, so many different women I can't recall them all. I have masturbated thinking about women I've had sex with, particularly one co-worker who I have many explicit photos of (taken by me, taken by her, and some by her husband). Another co-worker liked to watch me jack off, so I fantasize about her naked body, but especially those times I masturbated at her request or just because I was in need and she was encouraging.

When at work in my younger days, there were hot co-workers who got my blood flowing. I had a many a quickie jack-off session in a mens restroom stall after seeing pokie nipples, etc.

Also, when we were younger, my wife had a hot first-cousin who was slender with large breasts of whom we had a few sexy photos of (clothed). My wife knew I fantasized about her and even said if she walked in us having sex she wouldn't mind (it never happened). However, a few times I took out her photos and jacked off while my wife watched. Now I have photos of her hot, sexy daughter (starting as a teen) that I sometimes masturbate to.

There were also two guys from work that I fantasized about. One was rumored to have a large dick and I jacked off thinking about seeing it. Another guy worked for me and a couple times when talking to him in my office, I got a raging hard-on with him sitting on the other side of my desk. I never jacked off thinking about men at work, but did it later at home or did it while traveling in a hotel.

[iammmd55]

So, before you start thinking that I’m going to tell you about how I made it with my friend’s older sister… no of course I didn’t. She just smiled at me and I realized what I’d just said and started to get nervous but she just got in the car and went to do whatever she was going to do. We never mentioned it again and while I felt a little awkward around her the next couple times I saw her, she seemed fine around me so I stopped stressing about it.

Then it was, I thought, pretty cool because we had this little secret: I had seen her nude and was spanking it to her and she KNEW I was spanking it to her and didn’t think it was totally gross or that I was a creep for doing it to her and for a nerdy 8th grader, that was really something.

High school was a little different. The girls
at school weren't my friends. The girls in junior high hadn’t been either, but all through high school, I was aware that while others were, I wasn’t dating anyone, wasn’t going to, wasn’t one of the guys the girls would like. I didn’t really mind it, I wasn’t resentful or hostile, it was just we were in two different worlds. Awkward, nerdy guys weren’t going out with pretty girls and making out or getting laid.

But we were masturbating to them. In my class there was N., a slim, boyish figured, preppy, pleasant blond with an angelic face and brilliant blue eyes. P., olive skinned, black-eyed, with glossy black hair, a pixie-ish face and a great figure; and M. blonde, tan, curves in all the right places, and wild (junior year I learned she was fucking one of our young male teachers) who were the top contestants in my spank bank. My good friend, equally nerdy and also girlfriend-free, admitted to also masturbating to N. and I found that reassuring.

As before, when masturbating to these girls, it was only to images in my mind of their faces, them in swimsuits (which by the end of freshman year, I’d seen) or how I’d imagined they’d look nude. I was never doing anything with them, nor were they doing anything on my mind other than looking beautiful as I lay in the dark at night, eyes closed, pumping myself to climax with one or another of them.

[mash2014]

I went yesterday to the dentist. After I was checked my hygienist took over. She is a very attractive early 40s, wearing snug scrubs.
She sat at her stool and has always sat with her legs spread. On this occasion, I could perfectly see how her pussy was outlined. It was a beautiful scene. Her ass is perfectly round. I was extremely horny. I went home and all day long I was thinking of her beautiful pussy and a gorgeous ass.
After the wife went to bed, I pulled my pants Dian and started rubbing my cock when I started to cum. I hadn’t had a cum that explosive and quick in decades. I’m still wanting to masturbate thinking of her.

[iammmd55]

Home from college for the summer after both my second & third year, I had a pretty bad crush on my hygienist who was a tall brunette with a great figure and wore, I thought, particularly tight scrubs which showed off her fantastic ass. She was maybe 10-12 years older than me, married, but very friendly, flirty and touchy, resting her hand on my shoulder or arm, even my thigh at times as we’d talk before & after the procedure, and even sometimes during as she’d talk.

I didn’t quite know what to make of it. She was great looking older & married so I was a bit surprised but also turned - on. Had she been my age & single, I’d have asked her out, fulling expecting to be shot down, but I’d have had to.

Maybe she just thought I was “safe” - too young and she was married - and maybe she could just tell she got me going and liked that. Not in a malicious way, but in the “it’s nice to know you find me attractive” way.

She was a major player in my spank bank those summers who I’d come back to (no pun intended) over & over. I even went back to my little sister’s been - bag chair a few times, mounting it missionary style and wrapping my arms around it, humping it imagining I was on top of & inside her.

[spunkluvr]

I've wanked myself off so many times to thoughts of a particular work colleague. Always suit and tie at work but when he visited me at home one day he wore VERY tight jeans, and I could see his cock reached half-way down to his knee. I don't know how I restrained myself! I've dreamed of sucking him off for years.