Orgasm(s)! Multiple, that is…

Long considered the territory of women...multiple orgasms have been envied by men for many years.

Yet there is information out there about the elusive phenomenon of male multiple orgasms. Just Google it and you will find some cool YouTube videos made by a sexologist, and more than a few people trying to sell you the "secret" of multiple male orgasms.  There are a number of factors that purportedly come into play...perfecting the ability to delay orgasm, breathing, muscle control and practice, practice, practice. There are also people in discussion groups in various places on the internet that talk about it as well. Pretty much all these groups say male multiple orgasms have one thing in common - anal stimulation. This seems to be an important part of the formula. Not all men who can achieve multiple orgasms use anal stimulation, but from what I have been able to gather, more men who include anal stimulation in their efforts are successful. And the numbers are not too high anyway...perhaps because it takes dedication and time to achieve.

So...lucky me! I have a man who, in his younger years, took the time (a significant amount) and trained himself to achieve multiple orgasms by his own hand (and an Aneros toy). He had mentioned this at some point, not going into a lot of detail, other than saying it had indeed taken considerable time and he rarely did it now. I recall once when he had an orgasm with me stimulating his prostate with my finger while he was jerking himself off. He came once and never stopped stimulating his cock...and came again. That was quite exciting to see...and participate in. My man's cock is definitely my favorite toy to play with. We get along smashingly (sure, my man and I do - but I meant his cock and I).

The other night we were playing and I was in a definite teasing mood. I did just about everything with his cock for about an hour and a half without letting him come. I sucked it and fucked it and rubbed against it and licked it and wrapped my hand around it and jerked him off...and wouldn't let him come despite his requests. Only then did I start playing with his ass.  He was laying on his back with pillows behind him so he was partly sitting up. I opened him up with my fingers and used one of my smaller (6" x 1.25") dildos without the harness, just holding it by the base with my hand and fucking him with it. Sometimes I feel like fucking with the harness and sometimes I just like using my hands. He loved the feel of the dildo, but my finger on his prostate really made him tremble with pleasure, so I set the dildo aside and went back to the digital stimulation.  With my other hand I started to jerk off his raging cock. Though he wasn't tied up (what was I thinking?) he knew better than to interfere...he only touches himself with my permission at times like that.

Before long, he was ready to explode and he voiced those words I love to hear, "Mistress, may I come?" I think it was about the third or fourth time he had asked. Always said with a level of urgency, it's hard not to give him his orgasm when I first hear that because I so enjoy watching and hearing him come. But like I said, I was in a teasing mood. With prostate stimulation - he's always louder when he comes and often doesn't really remember what he said. But I do. Some orgasms are religious: Oh my God! Oh my God! Some orgasms are, contrarily, profane: Oh Fuck! Oh Fuck! Variety is indeed the spice of life, right? I love hearing his orgasms.

So I finally said yes. Barely 30 seconds after I gave him permission, he came, spurting a good amount of come onto his stomach. I didn't back off all the way and continued stroking him, but was careful not to touch the head of his cock much with my strokes. Having watched him jerk off, and having paid close attention, I know he continues stroking mostly the base of his cock for a while after ejaculating. So that's what I was doing. I'd stopped the stimulation of his prostate but not yet removed my finger. I'd been here before and was just about ready to stop all movement. But then...

"Keep going!" His words were a surprise.

I tightened my strokes on his cock just a bit and then stroked his prostate once as a test.  "Here, too?" I asked.

"Yes! Oh....Yes."

I resumed my rhythm and about 30 seconds later he had another full orgasm, with a goodly amount of ejaculate...again! A pool was beginning to accumulate on his stomach. Again I slowed my strokes...this time his words were even more of a surprise.

"Keep going!"

"Really?!" I had a little disbelief, I must admit...

"Really..." He was nodding. I was stroking...and actually starting to feel the burn in my forearm muscles on the prostate hand and my triceps from the hand that was still paying loving attention to his come-covered cock.

About 45 seconds later he had yet another orgasm, with the come dribbling out of his cock this time instead of shooting. And I would have bet that he didn't have a drop more come inside him! The combined total amount of come was impressive, indeed. Finally, breathing hard and a bit dizzy, he indicated he was done...laughing with joy at the mind-blowing experience he'd just had. It was incredibly erotic to watch...and to be in control of! So I gave myself a quick orgasm with a vibrator as he recovered - I was too hot not to! I mean...wow. I can only hear so many "Oh my God" moans before I just have to get off.

Holy Multiple Orgasms Batman!

Each time he had an orgasm, I could feel the buildup in his prostate just before. It would swell and fill with fluid and feel pretty hard and large. About the size of a walnut or just a bit smaller than that, perhaps. There were critical moments when I could feel him pushing down with his muscles...and that is explained in the youtube videos better than I can. So it was definitely a team effort...he had the past experience (specifically learned from these directions) and knew what it felt like...and I (apparently) did everything just right!

His hands never touched his cock the entire time. I have to say I was rather proud of my handiwork...next time I'm gonna tie him up!

6 Responses

  1. This is excellent! I just picked up, mere days ago, my first book on male multiple-orgasm and am happy to hear a real-life story from someone with experience. Anal stimulation is definitely part of the techniques this book espouses and they do add that, at the right moments, firm pressure on the prostate can help delay ejaculation and thus leave you ready for more orgasmic activity.

    I’ll take their techniques under advisement and practice as much as possible!

    You have, I must say, a very vivid erotic writing voice.

  2. Hey Joey – thanks for visiting, and for your kind words about my writing. You have a way with words yourself…Your blog has been on my RSS feed for a while now, I really enjoy it.

    The Aneros forum boards are also a great resource place for anyone wanting to learn about the various kinds of male orgasms, and the various ways to achieve them.

    Have fun practicing!

  3. My nieces husband was always trying to sell books on how to do this ,I talked with him and he told me how it works ,it is very hard to do , your have to exercise the muscle that shuts off the flow of of urine and semen ,its like the kiegle {sorry for spelling not sure of the word}exercises women do.I actually did this once, it takes a lot of concentration more so because men are disposed to just letting fly . its more a matter of timing when to clamp the muscle exactly as you orgasm if you do it right nothing comes out and you have an orgasm and can have another and another but it is extremely tough ,you women are so lucky, love your writing.

  4. This writing was incredible Ruby! I couldn’t have explained better how intense the experience is…but I’ll try anyway;)

    The first time I experienced multiple orgasms I was alone. It was also the first time I ever tried anal masturbation. I didn’t know how important the prostate gland was in the process, but discovered accidentally. I started out with common household objects, such as toothbrush and screwdriver handles, working my way from smaller to larger, and then back down to the smaller ones, relishing the feeling of being able to easily accept the smaller objects once I’d loosened myself up a bit. Finally, I went to my finger(s) for the advantage of a more accessible angle to an area that made my entire groin quiver. Little did I know this was my prostate, but I began stroking it quicker and harder, with first one, then two, and finally four fingers…

    At this point, I had to lay down on my back on the bathroom floor and had my legs up over my head while continuing to massage my prostate. I felt my cock throbbing as cum started to ooze out; I let my feet fall back to the floor, and stroked my dick with one hand while the other continued to massage my prostate, and within seconds my cock began to spasm and cum shot out all over myself and the floor. I couldn’t remove my fingers from my anus yet though. My prostate was throbbing and it felt so good I just kept stroking it. My dick was still hard, but extremely sensitive to the touch, so I removed my other hand from my shaft, and began to lightly rub the head with the tip of one finger in slow, methodical, circular motions. I could feel my balls pulsating, and knew there was more cum waiting to be unleashed. I ceased massaging my prostate, and inserted the comparatively tiny toothbrush handle again after having nearly fisted myself. Needless to say, it easily slid in as far as I wanted. I was still circling the tip of my dick with my finger, having read once that doing so while laying down caused intense orgasms, since the cock had to use all of its own muscles to force cum up and out of the shaft without the manual assistance of pumping the hand up and down.

    This turned out to be more true than I ever would’ve thought. After nearly 20 minutes of painfully teasing tip stimulation, and an anus that was rhythmically gripping and releasing the toothbrush handle, I felt cum rushing up my shaft and instantly grabbed the toothbrush to stimulate my prostate again. While rubbing the hard plastic against my prostate, and my finger still stimulating my tip, I had the most insane orgasm…there was no explosive force to this one, but it was much more forceful than the “oozing” that had been a precursor to my previous orgasm. It was as if my cock was pouring out cum. Juices just kept flowing up and out of my cock, streaming down and covering my shaft and pelvis. The whole thing lasted about 30 seconds and left me completely limp and exhausted, shuddering on the floor covered in my own cum. Amazing…

    1. Zeke – thanks so much for sharing your story of multiple orgasm discovery via prostate stimulation, wow! I really appreciate hearing this from the male POV and also appreciate the detail. As you can imagine, there are many men out there who would love to experience something like this. I have heard from number of men that a more rigid toy of some sort did the trick far better than a flexible dildo and let them pinpoint the best area for stimulation. I have also heard the guys over at the Aneros Forum talk about how they can feel their anus clench around the toy even with no penile stimulation. There is a wealth of information over there…including about multiple orgasms via prostate stimulation. Thanks again for sharing!

Leave a Reply

Your Source For All Things Pegging

Information and resources for anal sex, bdsm, strap-ons, intimacy, and female domination. Let Ruby know what you think! Leave a comment, register for erotica, or catch a webinar.

More Articles

Anal training cone pops right up

Podcast #303 Pops Right Up!

Pegging Paradise Podcast #303 Just when you wondered if you’d lost me… Another podcast pops right up! Information/Articles Equipment I hope you enjoy this podcast.

Read More »