What it feels like to have sex with 20 women at once…while a sea of men watch

On a tantric sex retreat recently I had 4 peak life experiences. When I say peak experiences I think that they might just represent summits that I have never found in my life before, possibly most people would find them the same.

In no particular order, the four of them were:

• The discovery that I can squirt, something I didn’t know was possible as a trans woman
• Having my vagina “de-armoured” and crying like a baby through most of it
• Being present with a woman while she had her brains fucked out by more than one person, and living it vicariously not just emotionally and spiritually, but also physically
• and the one that this post is about, having group sex with 20 women (and no, I didn’t count them, this is just a guess, but is +/- 2).

The retreat was very structured and professionally run.  And women don’t often relax sexually in spaces where men are present, unless there is a history of intimacy.  Of course, swinger parties and key parties are no. doubt different, and I have never been to either, even if I have been to sex parties.

Sex parties are a bit of a strange bird, as they are increasingly selective about who attends.  And of course that is a good thing for those in attendance.  You want vetting in terms of consent and behaviour and respect. But I know that many places will vet for other reasons, and I shudder to think that age, race, sexual preference, or other practices might be in play.

There was a vetting process that I went through to be on this retreat.  And as the only trans woman, I was the odd one out, but I didn’t feel as if I was a token.  Showing inclusivity.  I felt genuinely welcomed.

I was also not only not the oldest person present, but also not the only sex worker.  There was an FSSW (full service sex worker) there who was still seeing clients out of a brothel once a week who was in her tender mid-70’s.  But I loved what she did the rest of the week too—write children’s books.  Pretty amazing woman.

I had a bonding experience with a skinhead man who warned me about my personal safety in the Eastern Bloc, particularly Poland, where I am thinking of going later this year.  He was touchingly concerned for my safety.  “I may look like them, but I am not like them, even though I know what they’re like.”

Never in my life have I had to worry about my safety.  And yet, it is a new reality.  And it isn’t safety as a woman, it is safety as a trans woman.  Is it better to be raped or beaten and killed?  Or all three?  Or just jailed.  Or jailed and beaten?  This is reality for me.  I won’t hide. I don’t pass. But I won’t live in fear. I will take chances as freedom began with transition. And I will go where I want to go…and I don’t want to accept that a world has no place for this little patch of the kaleidoscope of humanity.

It is perhaps foolish, and at times I reconsider my thoughts of being a face out sex worker.  A face out trans sex worker in an era of facial recognition.  My fear is that I might be banned from travel to certain countries.  Or jailed. A primordial fear.  The insidious control of our freedom.

Back to the retreat.  There were roughly equal numbers of men and women.  I was the only lesbian there too.  Only one of the men was gay, but all of the women at least by the end of the retreat had had bi experiences, and several of the men.  In the case of the women, I don’t think it was dressed up as “sister culture”.  None of us needed the fig leaf.  The men did dress it up as being brotherly, and not being afraid of male touch.

I will say it now.  There were some conventionally gorgeous women on the retreat.  But all the women, regardless of age, shape, size, looks, were all gorgeous.  There were young women, old women, middle-aged women, and all of us had our charms and beauty.

One of the men, perhaps the most conventionally attractive, complained to me that one of the guys had let on that he was so happy to get to fool around with her because she was the “hottest” girl there.  She was really disappointed by that, as it was counter to the experience.  Can you see how different men and women are?

I ended up speaking to this man later, who was lamenting that he was not picked as a partner in a lineup, and how that hurt his feelings. “Pick me” culture is hard to escape.  Armed with the knowledge of what he was like from this woman, I shared with him that women can see right through his bullsh*t.  I was a bit miffed with him myself for when he was the last man standing, he refused to work with me on a particular exercise, claiming that he had no connection to me. Don’t pretend you’re woke when you are still fast asleep.

He made a speech that “sensitive guys” make to women about how important it is to have an emotional connection, thinking we don’t see right through the BS.  Many men clearly think women are stupid.  And some women, who are not stupid, ignore the comments, because they want the stability of a man, of a relationship.

I love that I can no longer offer to many women what I never wanted to offer in the first place, my masculinity.  I don’t have a c*ck, so I don’t have to even pretend to be a man.  I don’t know what I am either.  Part of my desire to be on this retreat was to discover this.  I guess that I wanted to explore my orgasmic potential, to find that elusive orgasm before the one year anniversary of my sex change.  Many important things took place on this retreat that are part of growing up.

And yes, I really do need to grow up…or maybe not, but I am growing up anyway.  And I am in no hurry.  The truth is that I am just one year into accepting myself as a woman, with a birthday of the day I came out of surgery…andhormonally I am still a teenager.  And second puberty will continue for me for another few years, just as it would for a natal girl.

My kids point out to me how much my behaviour resembles that of teen girls at times.  Its hard to be a daddy and a young girl at the same time.  I’d say I am navigating the chaotic mess pretty well.  Figuring out what it means to be female, to be a woman, is my life project.

On the retreat I was confronting things inside of me.  I nearly left twice.  The first night or first full morning, and on the day of vaginal de-armouring.  Those feelings will be the subject of separate posts probably, but in my stream-of-conscious mind, you never know when it will come tumbling out.

I mean, I was wondering, would I have sex with men.  I have just taken the “controversial” decision to be an escort, and not “just a dominatrix”…and it is clear to me that I am doing this for me, not for my clients or anyone else.  And chances are, that my clients are likely to include men who want to f**k me.  And I have set a price at which I am not only willing to do that, but at which I will enjoy myself.

But having sex with a man when no money is involved would be strange for me.  Like I actually want it.  And I don’t.  So, the money thing has to be there.  And I found myself not quite knowing how to deal with the men on this retreat.  And the fact is that the treat was essentially heterosexual, even if there was lot’s same sex touching.

But sex has always felt so grown up to me.  And there is something profoundly innocent about the female body, even in its full hunger and lustiness.  And this is what attracts me to women, to being a woman.  That I can revel in my own innocence.  That I can be in a world of touch, and caresses, and play, without having to f**k in a conventional sense, which feels so different.

And there is a part of me that is wistful when I have been making out with a woman, tenderly, gently, touching, exploring each other’s bodies, caresses, and then see her with a man, knowing that he scratches an itch that I will never scratch.  That’s a bit like what it is like to hang with straight women who walk on the wild side.  I prefer the company of lesbians or at least women who lean hard towards women.

Well, one evening things began by separating the men and the women into two groups.  They physically separated us too, with a wall of pillows going down the middle of the room.  And while the men were meant to touch one another in brotherly spirit, I didn’t really pay much attention.  Maybe none.  I was told later that they were mostly standing.  Oh. And everyone was naked.

The women, on the other hand, were in a messy pile on the floor, writhing gently, like snakes.  It was called “dolphin sex” which is an apr metaphor, and one I have used to describe the spiritual connection I have had with a dominatrix and a lover…it is evocative of how slip and writhe around one another as we bounce and prance through the waves.  I barely opened my eyes and I think I made out with, touched, and was touched by every woman there.  

What else did I notice.  We all smelled of pussy.  Funky, animal, divine.

And at one point at the beginning and perhaps on occasion throughout, I found myself bathed in a sense that those moments were everything that I had ever desired.  That to be with women, sexually, yet without agenda, and to be with such a diversity of womanhood, body shapes, personalities, and smells.  The smell of female desire, sex, hunger.  It was exquisite.  And it lasted for hours.

Somewhere along the line a lane was opened up between the men and the women, but it was a one-way lane only…the women could go to the men if they felt like it, but the men could not come to us.  I am aware of only one woman who crawled through to the men, and at one point was with seven men at once.

I had spoken to her the day before about her goals for being there, and it was to step into her “shameless slut” and to let go of her religious Catholic upbringing.  Such a common story.  But she was doing it in style.  I didn’t notice on the night, only heard about it during sharing the next day.

It was very late when I finally turned in, and found that as people generally slipped away I was in a profound, long mutual touching session with one person I found cute, and with whom I shared a police uniform fetish.  Yes, I think a woman in a police outfit is just about the hottest thing around.  She felt the same way about men in uniform.  She has been sending me seductive pictures of sexy cops ever since.

And so, what can I say.  To be in an open-ended orgy with 20 women has to be my definition of bliss.  Not least because there was no agenda.  Not least because there was no competition, no self-consciousness, no goal, no time limit, just gentle exploration.  It was beautiful.  Really, really beautiful.

For that experience alone, I would have enjoyed the whole retreat.  But there were other experiences, difficult ones, that were just as peak.  Only in different ways.

I did not meet my goal of an orgasm, but in a way, the pressure is off on the Tantric path, as clitoral orgasms are said to deplete our energy…and the goal is edge, constantly.  I was made for Tantra.  If that’s the rule.  I used to edge myself for days, weeks, months…so profoundly yummy.  

And I guess that’s what it feels like to be a girl who likes girls.  To live on the edge.  My favourite place.