How to become a multi-orgasmic man

The truth from across the transgender divide

Boy, this is set to be a doozy.  But the things I have learned about my body, our bodies, and especially trans bodies since I began my own gender transition journey have challenged everything.  Kindly rewrite and reread the last sentence with the word ‘mind’ swapped for ‘body’.  Even more.  And finally, ‘emotions’, which are a holding space for the spiritual aspects of sexual connection.

With emotional connection, I have something approaching a constant.  As a man, or should I say a ‘male bodied person’ (probably, but it’s a clunker, so kindly indulge my misuse of self-gendering for the purposes of this post, as I think none of you would falsely pin on me the word ‘man’ at any point in my life, no matter how I manifested), I was already totally bound up in the emotional aspects of connection. Sex has always been about an emotional connection.

I will give you a negative example from my own life.  My wife is/was a gorgeous woman.  No red-blooded man would ever turn her away.  She is every inch to this day a babe.  She is witty, intelligent, self-possessed and she is drop-dead gorgeous.  I think that she’s hotter now than she was a year ago.  Divorce seems to suit her.  But fifteen years ago, the night that she told me that my sexuality disgusted her, she severed the emotional connection forever. And overnight, I lost all desire for her. I could still see that she was objectively hot. I could also at times find deep within me a feeling of sorrow that motivated me to give to her. Usually on her birthday.

A small aside. This wistful feeling is a very powerful emotion that mixes sexual hunger, desire, feelings of fleeting and fragile beauty, the ineffable divine. It usually travels with tears. If I find I can summon it when I am with someone, it is an almost overwhelming emotional feeling. What I don’t understand is why this magic is easiest for me to tap into and live in when I am with a Sex Worker. The anonymity, the barriers, the distance, the guard rails, make it a safe space to experience this. The irony that it takes a “stranger” to find emotional connection is not lost on me. But it is no less delicious for it.

Back to my wife. Okay, the sex already wasn’t great, so I didn’t miss it much, and masturbation fulfilled the release part for me, but the death of our marriage was born in that moment, when the most important reason to be together with someone—to be understood and accepted—was gone.

Fast forward to now.  As a trans woman, my partner prospects are much smaller than when I was a man.  I get this even more now.  If I dress in boy mode, or when I dress just half-way female, the looks and approaches I get are off-the-charts.  Many women, it seems, are turned on by effeminate, sexually ambiguous men.  And so, I am meeting so many women in ways that were never possible.  Star Child told me she thought I was ‘gay’, entering the long list of women who process a M2F transgender human as “straight” (in the sense that I am now a woman and becoming a woman as a tortured way of justifying that I am gay—and boy if this turns out to be true I will be very disappointed in me).  But I don’t believe her, I think that is convenient now because we aren’t romantic, but when she lured me onto her bed the first time I went over to her place, and before she knew my dick was dead, I think she processed me as a kinky man.  The first time we had coffee I told her that I was a slave to pretty women even before we sat down. A few weeks later she was in my house in Europe for a very extended stay. I’m just sayin’.

There has to be truth to the idea that women feel more comfortable around me because female energy is just less threatening.  As the only “man” in all of my dance classes surrounded by women who range in age from 20 to 56, I have become an adopted mascot.  None of them “know” I am trans, but since I tuck and wear really tight bottoms, and because I have small but visible boobies, I think they get it.  I also think that the subtle yet telling linguistic shift to the use of feminine pronouns for our group, “ragazze” meaning girls, when we are being talked to by one of the teachers, makes it clear.  [In Italian, even if there is a group of 100 women and there is one man present, the pronoun will shift to the male pronoun, which is default for mixed-sex groups, ie it takes the presence of one man in a sea of potentially thousands of women to turn them all into male-pronouned people…’ragazze’ would become ‘ragazzi’—plural is male no matter what].

As the author of this blog, I participate in a wide range of online forums as a client, as a sex worker, as an erotica author, as a witch, as a somatic therapist-to-be, and also as a trans person looking for insights and knowledge into the journey ahead.  Last night I went down a rabbit hole of intimacy, wondering how I will ever close the intimacy gap.

The human obsession of ticking all the boxes in a partnership means that by going cock-less I will be excluding the vast majority of the women who I would be attracted to and who I would hope would be attracted to me.  So while I might be the kind of emotionally available man they have always dreamed of, because I am not a man down there, or even between my ears anymore, I’m out.  Many trans people lament this and other issues of dating that arise for trans people, which is beyond the scope of this post.

But you know what? She can gender me male if she wants after I have had SRS, ie. up-cycled my whotsit into a vagina. I was joking with my kids the other day about how I look forward to wearing men’s clothes again, even boxer shorts, but only once I have had and healed from surgery. Would that make me a drag king?

Since I have spent most of my adult life in a world of sex that on some level always revolves around the cock, I have to do my part to make a life without cock one of joy for my future partner.  And ‘get a strap-on’ is not the idea, though I will surely use one and most likely do a better job with it than I ever did with my own apparatus.  No, I need to learn the art of pleasure in a whole new way. Of giving pleasure. The concept has never mattered so much to me. I used to just take it for granted.

As a client of SW’s, as someone who really enjoys that special connection which can happen when you strip away all the noise, and when you can come together with none of the baggage of real life and just be two bodies together, or just focus on the aspects of you which foster connection with aspects of her, you can get further, faster.  I wrote about a sublime experience with an FSSW.  It was a beautiful evening, haunting, and also very unexpected.  Most of it was spent getting to know each other, and I was blown away by how open she was in a world where openness seems utterly taboo.  I was also stunned that she kissed me, and found it such a tender and innocent connection.  She read me and connected with me as the professional in her is trained to do.  She also didn’t watch the clock.  I did, and an hour after our time was meant to be up, I apologized for staying so long, dressed quickly and left.  If it wasn’t such an expensive luxury, I would have been back many times.  But maybe it wouldn’t be quite as special.  I am saving to see her again. Jeff Bezos can fly in a rocketship–I’ll takethe feeling of being in her arms any day.

There is something I would like to do with her.  DATY.  I love this acronym.  Dining At The Y.  Cunnilingus.  Last night, the rabbit hole in question was with a group of sex workers who were discussing clients who ask to go down on them.  There was a lot of unfiltered commentary, most of it condemning men for wanting to do that, for refusing to use a dam (ie. protection), but more explicitly for thinking that they are allowed to give pleasure.  Or that pleasure will be felt.  I’m not criticising or judging any of those feelings.

Who is going to be a better teacher of how to please a woman than someone who makes a living having sex?  In my experience, who is cleaner and more hygienic than a woman who has sex for a living?  Who is actually going to taste better than someone who is fit and extremely body conscious, including about their diet, than someone whose financial well-being begins and ends with body care?  But reading these things makes me realise how delicate and respectful I will need to be to broach the subject.

[Note to those of you who love going down on your partner…try seeing if she is willing to eat dark grapes, like Concord grapes in the US or Uva Fragola in Italy…and see if she will eat a bunch of those 4-6 hours before going down on her…it will change the flavour in magical ways].

I do know of one SW who actually specialises in this area.  But I haven’t gone to her because she is in a price category that is off the charts for me.  I already thought I was actually working with the highest price bracket, and for what I usually do with an SW, I generally am…but this is a different order of magnitude.  I won’t rule her out, as it is hard to put a price on life lessons and personal growth.

But we will see how it plays out.  I haven’t written to her, because I am very discreet about putting that kind of thing into an email or other exchange.  But also because I wouldn’t want to give her the impression that I had placed a condition on seeing her.  I will see her anyway, and would rather discuss it with her in person, and plan to continue to see her when I can afford it, organised far enough in advance around things that I know she also really enjoys doing.

I can also see very clearly in my mind how I will ask her.  That I will knee before her and talk about it, my motives, my desires.  And make sure that she knows that if she is not interested in that, or that if it is too soon, then I will not lament. It is very intimate and personal. She might say ‘yes’ and might not…another SW I have followed for years but never seen waxed lyrical about a client of hers who just does this with her. She loves it.  And this action on my part, in submission, is a match to her mercy.  There is nothing which appeals to me more than a woman’s mercy.  Nothing in life which feels more sublime.

Why do I need this?  Well, I am not so experienced in the world of DATY.  Part of that is that my wife didn’t like it very much.  It made her uncomfortable.  But maybe it was me.  I do know that some women love it and others don’t.  But being ‘good’ at it, being ‘good’ at pleasing a woman, about touching a woman, as something akin to a lesbian, is really important to me in life going forward.  The giving of sexual pleasure.

Boy have I strayed from the topic posed in the headline!  The punch line to the question posed is this.  My libido is back.  I seem to be tracking the moon cycle with my body, so when the moon is full, I struggle to sleep, and my libido is through the roof.  In some ways this would be my period, which is not when my libido should be through the roof, but as a trans woman, some things are not the same.

Something else is going on which will get its own post.  I have switched endocrinologists.  So even though progesterone has kicked in for the past 6 months and brought my libido back, my new endo has taken me off of one of the two puberty blockers I was on, the one that suppresses testosterone production altogether, spironolactone.  My testosterone levels have been so low now for over six months.  My new endo believes in oestrogen mono-therapy, meaning using the natural sex hormones of the body to control testosterone.  So, we are watching to see whether taking me off of spiro leads to more testosterone.  In the meantime, to ensure my testosterone does not come back, she has doubled my oestrogen dose.  So, in case we forget, oestrogen is a sex hormone.

What is she doing?  Trying to get my levels to be as close as possible to a teenager going through puberty.  What’s happening.  My energy levels are skyrocketing, and I am as horny as fuck.  I am getting morning wood, erections when I am aroused…this used to be disturbing to me, but right now I am more like ‘hail friend well met’ about it.  For one thing, my apparatus is half the size that it was when I was a manly man.  Plus it used to get so hard I would think the skin was going to rip.  It doesn’t now.  In its plucked and denuded state it really doesn’t look like a body part from someone my age.

But psychologically, I don’t feel as disgusted by it.  I have been able to touch it and play with myself to orgasm more times in the past few days than I have done over a lifetime.  Literally, I masturbated with my hand three times in my entire male life.  Three times.  I did that in less than an hour two nights ago.  When I had an orgasm the first time, I thought, ‘oh, wow, that felt good’ but I also immediately saw that I was shooting blanks, and more importantly thought, ‘I want to do that again’.  The tip of my penis is being nourished as if it were what it is to become, a clitoris.  Nerve growth is increasing, blood flow is increasing, my body is already beginning to treat it like the part of me it will soon be.  Talk about sensitivity.

And so, one after the next, I coaxed myself over the edge.  It doesn’t feel the same.  The male orgasm has a moment of explosive ecstasy that is felt in sync with the pumping out of cum.  There is a bit of a burn (and men, you should know that if you pee just before sex your orgasms will be more intense).  But along with that extreme feeling of release comes exhaustion.  I still feel a bit of the pulsing sensation that accompanies the male orgasm, but it is much more diffuse in my body.  It is not just concentrated in my bits and bobs, but lights up my entire peri-anal area, my perineum, by rosebud, but also my inner thighs, my lower belly.  And my nipples, if they can feel the sheets on my body, or my skin more generally, everything is just lit up.  And what is weird is that I just get hornier.  I think not only, ‘I could do it again’ but more ‘I want to do it again’.  To stay in that space.

Just as my male apparatus became more sensitive after orgasm, so too does it now.  But because the starting point with the head of my penis being already what I would equate to the post-coital sensitivity of when it was a man-dick, I am geared up for the pleasure as pain which seems to accompany this new feeling.  I can’t go past three.  It is too much.  But I think I am going to have fun with vibrators.

All of this has gotten me to musing on the purpose of our bodies, the nature of pleasure, and how and why we like sex a certain way.  From an evolutionary perspective it makes sense for a man to grow tired after orgasm.  That he experience release and surrender, and perform the most submissive act of all, to fall asleep in her arms, is evolutionarily sensible.  And that the act of sex for her serve to only increase her libido, her energy, also makes sense.  I know men don’t like this, but it is true.  Our species is unique amongst the primates to value monogamy as much as we do.  My feeling is that this is a social construct designed to empower men.  The truth is that the species is best served by the promiscuous and empowered woman.

I dedicate my life and body to cultivating this kind of empowerment.  A woman with the freedom to choose, with options, without a strain of necessity, is the most intoxicating.  Right there in a nutshell is what makes a dominatrix so appealing to me.  She is symbolic of liberation in ways that speak to my core.  

So, you want to become a multi-orgasmic man?  Become a trans woman and maybe stop before I will, though I suspect that unless something goes wrong on the operating table, I will be more orgasmic than ever once I have crossed the bridge.

Post-script

Is there something wrong with someone who might do to their body what I have done to mine for pure sexual fulfilment? I think it seems a perfectly good reason. [I have others, don’t worry. Just sayin’].

Is there an emotional reason to why I am now post-orgasmic? Is there something about the male orgasm which has nothing to do with the physical nature of being ‘spent’ but where being emotionally ‘spent’ is somehow an evolutionary advantage?

Why am I asking these questions? Because if you make a lifetime habit of looking under the ‘wrong’ rocks, the rocks that others don’t think to turn over, then you find more gold.

Have a sexy weekend!