Masturbation

I've always had an interest in submission to women, but never really been able to make it real. I've been too shy.

My name's Len, and I am male, 25 years old. I'm not super handsome, but not ugly either. Just average. My cock is pretty impressive, though getting a girl to actually let me use it so she can appreciate just what I can do with it has sometimes been a challenge. So I work out, keep myself groomed and in shape, and I hit on women all the time.

If I can get a girl to actually sleep with me, she usually comes back for more. That's how I know I am pretty good in bed. That and the fact that the two girlfriends that I have had in my life that I would actually say were girlfriends, like a committed couple, were actually fairly good looking. I've done a few mildly kinking things with girls, always with their consent, like handcuff them or spank them. It's been fun, though in a couple of cases those girls didn't come back for more LOL.

That said, it isn't always easy to get a girl. The good looking ones insist on these strong nordic handsome types.

I've had a pretty rich fantasy life. Now... that sounds sort of pathetic when you get down to it. I mean, who wouldn't want to do it for real, rather than just fantasize. But really, what do you do when you masturbate? Fantasize, of course. And I've found I don't just fantasize about some girl or movie star, I have very specific fantasies.

Sometimes I think I have a masturbation problem, like an addiction. I masturbate at least once a day and usually twice. Consistently. Pretty much every day. Some days three times, when I don't have a girlfriend or a date. Maybe it was my upbringing but I can't stop jerking off and keep thinking I am doing something unhealthy. Like, an obsession or addiction or something.

I know, that's silly. I know it is silly. Everyone masturbates, and me doing it two or three times a day is just not that big of a deal. I think. I am pretty sure.

I always masturbate before first dates, so I won't have this embarrassing bulge in my pants during the entire date (I always get an erection around beautiful... uh... well, any woman roughly my age and not hideous). It also helps me relax a bit and not be so horny and obsessed. A bit more mellow, you know. Girls don't like it when you hit on them too hard.

Getting back to my interest in submission. Which is why I started writing this whole thing. The whole idea that I really fantasize a lot about women dominating me. Or... just controlling me, or even just doing things to me. I honestly am not entirely sure what it is, what my desires actually are.

So one thing I have done recently is fantasize about a woman hurting me, like doing some sort of punishment. And it made me wonder, just whether I really wanted to be in pain. OK, this is why I am writing this down in a journal, because it is weird and unexpected and it is sort of something I wanted to write about and think about.

My few experiments with D/s have always been mild and with me on top. What would it mean to have a woman actually taking me in hand. Punishing me. Would I like it? Would I pussy out immediately?

Hey, I realized there was absolutely nothing stopping me from experiencing a lot of what I was fantasizing about. I couldn't do all of it, but I could do some of it.

So last week I decided to try something.

I went to the kitchen, got two of those metal butterfly paper clips that are actually clamps-- you know, those black things with silver handles you squeeze and they open up then clamp down on the paper? Yeah. I got naked, went upstairs, stroked myself, then put one on my left nipple.

Holy fucking cow. That thing hurt like ... like... I dunno what. Holy shit. I took it off. Just crraapp. I'd seen plenty of porn with girls taking clamps to their nipples, and they didn't freak out like I just did and it made me feel like a complete pussy. So I tried again, this time leaving it on. Tears came to my eyes as I put the second one on.

I took them off after about 30 seconds. I couldn't believe this was the pain some of those girls went through. Like, they earned every fucking penny if this was what was happening.

I tried again. But this time... played with it a bit. And learned a bit lesson. If you clamp right on the nipple, the little protrusion, and nothing else, it's almost unbearable. If you clamp a bit more, back a bit and grab more flesh, it's more tolerable. It still hurts, but it isn't like holy fuck get this off. Later I checked out some porn sites and yeah-- almost always the clamps are grabbing a bit more boob than just the nipple.

The other thing I learned is that not very many people use those metal butterfly paper clip clamps. They are too stiff and hard.

Nevertheless, I kept those clamps on, determined that if those porn stars could do it, so could I. I masturbated while those clamps were on and I came like a bull. One of the best orgasms I have ever had. And then I took those clamps off and screamed and swore.

But I had done it. And the fact my orgasm was... fucking amazing, told me that maybe I did, in fact, have some desire to experience discipline and pain. Or... who knows.

After that I bought some clothespins. Yeah. Still hurt, like, real pain, but it's bearable. And the second and third times I masturbated with pain, I still felt the pleasure really intensely. In fact, the pain seems to lessen while I was stroking myself and completely go away while I was cumming.

So I proved something to myself. I could take it, I wasn't a wuss, and I might actually enjoy some of these activities.

Now, here I have to say that recently I have fantasized about this one girl while I masturbate. She's actually my next door neighbor. I live in a condo complex, and she had the condo next to mine. Her name is Katie.

Katie is this incredibly cute woman, a bit older than me; maybe about 30. But she looks young for her age and is gorgeous in a very professional, well groomed way. I think she's a lawyer or something. We say hi at times, like neighbors do. She's friendly, and nice, though she's totally out of my league. Still I take the time to be nice and try to be a friend or at least a neighbor.

And I happen to know that the way our condos are laid out, her bedroom is right on the other side of the wall from mine, and her bed is very probably pushed up against the same wall as mine, which means she is just a few feet away at night while I am masturbating. So, hey-- I can't help but think of her while I am stroking myself sometimes. Including when I was hurting myself.

I tried one other thing last night. One of the big classic things that domme's do with their submissives is pegging, at least in porn videos. Using a strapon on their man's ass, reaming them out. So, I have a left over dildo from my last girlfriend (a year ago we broke up... sigh... miss her...) and I pulled it out of the drawer, put a condom on it, and lay on my back with legs up. It wouldn't go in. Damn, I tried, but it wouldn't go in. Felt like it might be fun, but nope.

I got some mineral oil as lube and added it-- this time the dildo slid into my ass. Slowly. While I was stroking my cock. God it spread me wide. It felt a little like trying to poop the biggest log ever, but... there was also something really weird and erotic about it going in instead of out. It didn't hurt, though it was uncomfortable.

It did hurt a little when I pulled it out, which was weird. It's like my flesh was trying to grip the plastic rod in my ass and was being pulled out with the dildo. So I sort of moved it back and forth, in and out, without moving too much at the sphincter itself. I managed to get it in all the way, which was a weird sensation, filled all the way up my rectum into my colon, I think. Then pulling it back out actually hurt some, but I began to really pump it in and out.

And I came like a freight train. Cum spurt all over my stomach and chest, and a bit hit my chin.

All the while I was imagining Katie there, naked, the dildo strapped to her hips, thrusting it into me, her long hair hanging down, pushing it in and out...

Damn, I am getting horny again just writing this.