Time for the Boys: Masturbation Techniques

I never realized there were so many ways for guys to get off. I mean, it always seemed pretty straightforward to me: grip penis, stroke up and down, semen spurts out after a certain period of time.

Okay, I fib a little – that did seem to be the preferred method, as far as I could tell, but I did realize that every man did it differently, just as every woman has her own special method. In fact, this little factoid tripped me up when it came to me being willing to try to get a guy off with my hands – something that has happened few enough times that I can probably count the instances. It seems so particular that I know I’m going to do it wrong, so other than a little (or a lot) of foreplay, I don’t usually try to do it. I have helped. I’m not sure if it “counts” as masturbation, if my hand is on his hand as he strokes himself, or if it follows his hand in its glide up and down his shaft, over his tight, glistening head, and back down. It’s a delightful game though.

Still – insecurity on my part keeps me from really trying to get a guy off that way.

So, back to techniques. We know that every guy does it differently in terms of straight-up jacking off. Lube/no lube, fingers as opposed to fist, gripping it firmly or softly, long slow strokes vs short, pumping ones. And those things can all be switched up during the session itself as ardor rises and falls. It’s all such a mystery and a fascination for a person without a penis.  Really? I LOVE to watch and feel a man masturbate. Love love LOVE it. But that’s a topic for another post.

I thought I’d focus in this post on unusual or interesting techniques for male masturbation, as I did in my earlier post on female masturbation. I can’t attest to any of these methods, as I don’t have a penis, but some of them make me wish I did…

  1. Masturbation Sleeves There has been an explosion on the market in the past few years in male masturbation toys. I have known about fake pussies, strokers and Fleshlights  (one of the popular manufacturers) for some time, but until I started researching this topic, I had no idea the kind of variety there is in male masturbatory toys out there! Toys for women, sure…but for men? I was also (I am ashamed to admit) a little biased about the notion. Women can use toys, sure, but men?? That’s well…weird, isn’t it? I am pleased to say that I have seen the light. I’ve seen a lot of light lately, in terms of masturbation, male and female, my own and others’. But again – topic for another day (we have lots of days left in May!) I’m focusing specifically on sleeves here because this is the one toy that I had the opportunity to observe in use recently – and, having tried it, I am keen to try others. (Gateway toy?) I’m not going to try and rewrite the book on what and how with these toys though, since I haven’t seen many in use…I’ll just quote one of my favorite online sex shop’s description of them, and let your fingers and minds do the walking. (BTW, I do not endorse nor am I affiliated with any online retailer or manufacturer of toys. Any reviews or links are purely from my own experience and not an endorsement except inasmuch as I enjoyed the item or shop at the store.)


    From Adam & Eve:


“The most fundamental type of male masturbators, our collection of masturbation sleeves includes a number of strokers such as blow job stimulators, realistic options, and more.


Without any additional features, basic masturbation sleeves are anything with an opening and tunnel designed to stimulate the penis. The narrow tunnel is usually around five inches long and lined with pleasure nubs or ticklers to offer incredible sensations to the tip and shaft.


Masturbation sleeves are made from a wide range of material, but they’re almost always soft and flexible for optimal enjoyment. Most masturbation sleeves are also extremely stretchy to accommodate all sizes. Some options feature life-like styling, providing a very realistic experience.


Many masturbation sleeves are roughly hand-sized so you can easily tuck them away when not in use, making them a discreet, but immensely enjoyable, option for solo play. The portable size also makes them travel-friendly, as they slip effortlessly inside your bag.”


  1. The Plastic Baggie Trick I admit, this sounded really strange when I first heard about it. But then when I got to thinking…slippery, gliding wetness, locked away in a baggie that provides more gliding and no-mess clean-up! How cool is that? The friend that I heard about this from said that when he had been young, this was his go-to masturbation technique for that very reason. A little lube or spit, a sandwich baggie, and away he’d go. He said he could remember using this technique to hump into the crevasse between two pillows, imagining it to be the current flame of his young fantasies he was plunging into. Kinda hot, right? And best of all, when he was done, there was no “trace” of his nightly self-exploration left of his sheets, blankets or pillows.

  3. Two-Fisting I’ve done this with a man, as I’ve mentioned above, following a lover’s hand with my own as he stimulated himself. But have you ever tried it on your own? Using two hands, one stacked atop the other, for extra friction, extra grip? Another option for the two-fister is to grasp your balls and pull, caress or knead them, especially right as you’re about to orgasm. I’ve had my mouth of a man’s balls, and it is an amazing sensation to feel them pulse and contract as they get ready to explode. They move as though they were alive! Having recently played a little with CBT (cock-ball torture) recently, I can imagine for those that enjoy a little denial, grasping the testicles tightly just before you are about to cum might also be an interesting experiment…

  5. Tickling the Frenulum Okay, I found this on ‘net, so I can’t claim it actually works since I don’t know anyone who has actually done it…but it sounds so amazing I have to share it, in the hopes that I can a) convince V to play this way some time so I can hear about (or see) the results, or b) hear from someone out there who has tried it. If you do – share it with me! I’m a total whore for masturbation stories. You can read about the technique (and the many, many positive comments on it) here, so I won’t go into detail, but basically it involves gripping the penis lightly with one hand while stroking/rubbing the frenulum (the “v” spot just below the head of the underside of your penis) with one or two fingers of the other – and that’s it. No other stroking, rubbing or pumping allowed. Apparently this takes a long time to accomplish, with a lot of willpower not to just grip your cock and let it go, but from the comments it sounds like it’s time and effort well spent.

  7. Ice or Prostate Massage? I had a hard time deciding which technique to go for here. I’d heard about using ice while masturbating – the different sensations of heat, melting water and ice over the cock and balls making for an unusually stimulating session of self-pleasure – but then I ran across this video, and I swear it is hotter than any staged porn. Watching this made the decision an obvious one, because this video needs to be shared with the world. (But then, maybe I’m easy…I kinda have a fascination for V’s ass, and finding new ways to pleasure him is an ongoing quest of mine.) But wait! That’s not masturbation, right? Okay, right…but prostate massage can be a part of your masturbation sessions, either using your finger or a prostate massaging toy, such as the Njoy Pure Wand or the wide variety of massagers that Lelo offers. There are so many reasons to give it a try – don’t let society’s wrongheaded taboos on the activity hold you back. Want more information, recommendations or some fantastic how-to tips? Read Mr. Racy’s Guide to Prostate Play blog. I’ve already put a couple items on my “to buy and try” list for V – I’ll keep you updated on our progress!

That’s it for this topic for now, but I can imagine we’ll revisit it a time or twelve – and of course I’ll tell you all about it. Now go on over to the Molly’s Daily Kiss’s Kink of the Week and Kayla Lords Masturbation Monday meme check out the rest of the internet celebrating masturbation!



  1. Jim

    Very refreshing to see genuine and positive comments from a woman on this subject in a public forum. Many thanks!

    Especially good to see the word getting spread about the frenulum, a secret kept much too well in my younger days.


    1. Jade

      My pleasure! It occurs to me that if there was more open discussion on the topic in general, that discourse would be a lot more positive and affirming as opposed to shaming. We can only hope, and try to make it happen. :-)

  2. Molly

    We tried a masturbation sleeve once. It turned into an hilarious encounter but didn’t make him cum, that was my pleasure with my mouth in the end


    1. Jade

      I was shocked at how right this one was, Molly. I could *barely* get my finger into it. I have no idea what his cock must have felt like in there. I wonder if all the sleeves are like that? I’m pretty keen to get him a Fleshlight or something must to see…

  3. Kayla Lords

    We played with a sleeve once. It worked for him…but he also broke it, lol.

    As for the frenulum, I know it’s a sensitive spot, and it certainly gets him going, but I’ve never had the patience (nor has he, I think) to see if he can come with only that part being stimulated.

    We haven’t tried prostate massage but I know he wouldn’t mind.

    The rest was new to me. Thanks for sharing! :)

    1. Jade Post author

      Thank YOU for keeping a place in the net where we can talk about the topic & post the things that make us want to go masturbate, Kayla. :-)

      Re prostate massage, it is an incredible thing to do! I LOVE it and am so glad one of my partners did too. I’m working on convincing the other one… ;-)

  4. Modesty Ablaze

    Mmm . . . interesting (giggles!!!) . . . I shall have to ask some of my “friends”. But I wonder if they’ll admit to any of your discoveries! I’ll definitely be asking about the “Plastic Baggie”!
    Fun post!!!
    Xxx – K

    1. Jade

      The plastic bag was the one I was most surprised about. BUT ice now heard from several others who say they’ve done it! So it must be one of those things guys share in the locker room…lol

  5. sub-Bee

    I bought him a box of Tenga eggs for Valentine’s Day, I know that sounds odd but it was good fun using them together. They still aren’t as good as a hand but they do add a slightly different element.

  6. Davefan0609

    Wonderful article! Glad to see you again, Jade. Didn’t realize you were blogging again- glad I stumbled upon it and you are still alive and well! Ice- never!! the rest- well of course!!


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