Earning Pleasure The Hard Way

By Wheldrake, with my commentary.

When I began taking orders from My Lady back in 2012, I expected that putting some restrictions on my masturbatory activities would be fairly high on her agenda. However, she turned out to be surprisingly permissive on this point until just a couple of months ago, when she must have decided an invisible chastity belt would look good on her boy. Suddenly, my days of onanistic freedom were over, and I was only allowed to bring myself to orgasm if I fulfilled certain strict conditions.

[My interspersed remarks appear in italics like this. Celebration of International Masturbation Month (May) prompted the first set of restrictions. He had to request permission in advance, a system I found unsatisfying, in part due to differences in our time zones and email access.]

For June, the condition was that I needed to inflict some significant pain on myself, and send My Lady a report about the pain-infliction session illustrated with at least one photo, in order to earn the right to masturbate once to the point of ejaculation.

[My well-informed boy had told me that June 2 was the Marquis de Sade’s birthday.]

My Lady and I both thought that my report might make a good blog post, so it’s reproduced below – complete with a photo I took during the session, and with the little errors and infelicities that crept in as I typed.

 * * *

——– Original Message ——–

Subject:  Pain report

Date:  Fri, 13 Jun 2014 04:12:40

From: Wheldrake

To: Dilo Keith

The clamps are now nicely laid out on the desk by the computer, ma’am, ready to be picked up and applied to my tender scrotum and foreskin. I’m planning to report in “real time” over the course of a ten-minute session, like I did when I put the clamps on my nipples. Once again, the clamps are close to, but not quite at, their maximum tightness. I can feel a knot of nervous anticipation in my belly as I prepare to take the plunge. Scrotum first, or foreskin first? Scrotum, I think. It’s now 3:54 and I’ll start at exactly 3:55, for tidiness. Shit, I’m actually going to do this.

3:55. And we’re off. I’m already half-regretting the decision to put one on my foreskin, ma’am, because that’s the one that really hurts. The one on my scrotum is surprisingly bearable, and in fact I can hardly feel it at all. Perhaps that’s because the one on my foreskin is turning out to be so much of a distraction. I gasped in a way that I’m sure you would have enjoyed hearing when it bit down. Nevertheless, it didn’t hurt as much as clamping my nipples did last time.

3:57. The pain is now quite manageable, though there still a dull ache radiating from the foreskin clamp. I have to admit that I feel a bit of a sick twinge when I look down and see the metal biting into the most intimate parts of my anatomy. I’m sitting at the moment, and I guess I’ll feel more of the weight of the chain when I stand up to take photos. Let’s see what happens.

3:58. I’m now on my feet, ma’am, typing a bit more awkwardly. The weight of the chain is actually making the scrotum clamp hurt a little, though for some reason it’s not having much effect on the foreskin clamp. I feel like I’m getting off a bit too easy, so I’ll try bouncing up and down on my toes a bit.

 [Isn’t he delicious?]

4:00. Okay, that hurt, by shaking the foreskin clamp. I’ll take my photos, and then perhaps do a couple of jumping jacks for the grand finale. Whew. The foreskin clamp is still hurting, actually, and I’m also dripping. I’ll wipe that up before taking the photos.

4:03. Fluid wiped up, and photos taken, one from the side and one from the front. The chain was swinging a bit as each photo was taken, so it’s slightly blurred, but you’ll get the idea. My genitals are clearly and fully exposed, of course.

[I assumed he included the last sentence for the reason you’ll learn below. For the purposes of exposing him to readers and providing visual documentation, one photo is enough.]

4:04. All right, time for the grand finale. My foreskin is probably going to hate me for this…

4:05. Ow! Three quick jumping jacks, but yes, my foreskin suffered. It felt like it was tearing loose, and the chain really rattled, too. Time for the clamps to come off.

4:06. Removal wasn’t too painful, and it was a relief to see the metal jaws relinquish their grip. I’ll attach the photos, ma’am, and then proceed with whisky-drinking and general winding-down. I’m already looking forward to tonight’s orgasm, which will feel well-earned if I think back to those jumping jacks.

[He earned an additional reward for this performance.]

 * * *

The orgasm did indeed feel well-earned. Another consequence of that session, or more specifically of the photos I took, is that My Lady has now seen my penis – as have you, dear reader. She doesn’t seem to think her newfound visual acquaintance with what she calls my “boy bits” is any big deal, but I feel as though I’ve just surrendered one of the last bastions of my privacy and taken another significant step into deeper vulnerability and subservience. I’m sure many more steps still lie ahead.

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9 Responses to “Earning Pleasure The Hard Way”

  1. cammiesonthefloor Says:

    That was quite a letter you sent. Considering I find intelligence hot, I would be as turned on by the crafting of the words as I would by you doing the act itself. Well done.

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