Learning to love the vagina, and my own eager anticipation of what it will mean to have my own

I remember in high school a classmate of mine, a boy, said how much he liked to eat pussy.  He accompanied this statement with a fairly graphic use of his tongue and held his hand as if it were an ice cream cone.  I was at once astounded by his comment, fascinated, but also disbelieving.  I thought, “you’re too young to make a gesture like that.”  I think we were 16.  You decide.

My first encounter with a vagina belonged to one of my early childhood best friends, the daughter of my godparents.  Never mind that many years later I discovered that my godfather and mother were thought to have extramarital relations.  Often when parents put children together we wouldn’t get on, because just because the parents liked each other, didn’t mean the kids would.  Whenever that happened it was a big bonus.  Anyway, she and I liked each other.  We got on well.

Even then, at the age of 5, most of my friends were girls.  One day, over playing at her house she took me into the bathroom with her.  Even then, girls led me around, and I acquiesced.  I already really liked obeying girls.  And that suited me just fine as girls developed faster, we know that, and so felt like natural leaders to me.  I guess she just took me into the bathroom because she had to pee and wanted company, or just wanted to show me something.

She pulled her shorts and panties down and showed me her vagina.  I just remember how beautiful I thought it was, how much more beautiful than my penis. Vagina envy is real.  I don’t remember whether I said anything, said what I was thinking or feeling, that it was nicer than what I had, that I could already feel what I didn’t have.  How in that moment I felt the powerful something that Freud never wrote about, vagina envy.  Why would he?  How could such a thing exist?

I was ashamed to show her mine, but I did because she asked.

I don’t know what the conversation was after.  I assume there was a conversation.  I was never invited over again.  I never even saw her again.  My parents never said anything.  Who knows if her parents ever said anything to my parents.  Who would in a stuck-up East Coast Wasp household?  We don’t talk about anatomy.

My dreams of having a vagina were born on that day into something real.  Being a ‘girl’ was already in me, but it was a concept, and until that moment, had not been made real.  On that day, it became real, and I have carried a little flame inside of me ever since.  Soon enough.  When I’m ready.  No matter what they say.

Not so long ago I sat in the car with one of my trans sisters.  She was rocking boy mode, going through a phase, finding it hard to let her out.  They told me that seeing me flouncing around NYC in a pink taffeta skirt was very uplifting.  Empowering.  “This is the skirt I wore to my first meeting with my endocrinologist.  This and 3” pumps.”  We do what we need to hey.  I was tottering around that doctor’s office determined to make it from the waiting room to the consult room to the blood test in those heels.  We laughed about the spectacle.

We met because we were introduced, and despite my respect and affection for the person making the introduction, I was worried that my new friend was really a gay man or was gay.  It is confusing when you are trans you know.  I think it is easier to say what you like.  That makes me gynophilic.  That makes them ‘mascho-phyllic’.  I guess that would be the word, though spell-check says it is a neologism.  Nonsense.  Could it be that there is no such word?!

I shared my feelings with them.  I was worried that we were being set up.  That I don’t like men.  That I worried that he likes men, that he was a gay man performing female for the male gaze. 

“I’m not gay,” they said.  “I’m a woman, and I like men.”  A cynical person sitting next to a soldier, a rather buff soldier at that, would have found this challenging.  I did not.  “I’m afraid.  Afraid of hormones.  Afraid of the future.  I haven’t started, yet.”  The operative word was ‘yet’.  And so it was.  The very next day they went to the doctor and discussed their dysphoria.  This is coming for them, and I am one to talk.  I had hormones in my refrigerator for a year before I took them for the first time.  Long-standing readers will remember the hesitation born in the words, “I love men,” uttered by ex-Mistress.  For in those days, I wanted to be lovable to someone like her, if not her herself.  Those words made me stop, pause, put on hold, take more time, gather my strength, resolve, know that what I was about to do was real.

We also talked about vaginas.  My new friend told me of their fear of the vagina.  Castration anxiety.  Does that exist in the trans male to female world?  I think of it as euphoria.  How many erotic stories have I written over the years about being castrated?  There was a domme who was interviewed who wanted to castrate one of her slaves more than anything, but she said, “I’ll have to wait until I am ready to retire because it is a career-ending move.”  I was always positively pre-disposed to her and hope to see her one day before she does hang up her whips.  But I regard castration as an act of total intimacy, accompanied by coos and cuddles, “there, there baby, all better.”

I have enjoyed having hard-ons in my life.  Even if I never wanted to touch it myself, the pleasure of being engorged, of feeling something against it, a nappy, a person, a vagina.  It has been a source of joy.  It was even better when accompanied by an anal plug of some kind.  Preferably big.  The warmth which emanated from the entire area, spreading up into my guts, so delicious.  I could lie still that way for hours, lost in the delirium of sexual sensation.

To imagine a vagina in that mix, stuffed, sated, aroused, aching.

I dated a Jewish girl in college.  She was so liberated about her body.  Not stuck up and prude, afraid to be naked, like I was, she made it her mission to liberate me.  I went to class between her legs, and learned to please her.  And sex with her was wild, always wild.  Hair pulling, scratching, slapping.  I was silent, contorting my body to connect with her, seeking to please her without thought, to simply be animal.  I emerged from our encounters covered in scratches and bite marks, panting, feeling as if I had wrestled with a wild cat.  She was filled with laughter and bubbles and would sing.  Her voice was glorious.

Her parents were psychoanalysts.  They were my entrée into the world of self-help.  I use those words in contrast to my involuntary childhood experiences with pyschiatrists and medication—this time, I sought therapy, my therapist, not the one my mother chose for me, and I asked them to help me.  Nobody but me.

Other women I dated didn’t have the same love for their own clitoris’s that she did.  Or for being eaten out.  Sex became mechanical, something we did and got over with.  The unmentioned one, my first truly long-term relationship, was the best of the bunch.  Beautiful, well put together, in fashion, a lingerie model, a gorgeous, life-loving woman.  She too loved sex.  She taught me about the back passage, and she loved it back there, and taught me to love it too.  Her father had become gay in middle age, and I wondered if her love of anal had something to do with that.  Circumstances of life had me leave her.  Perhaps I should have tried to bring her with me, but I didn’t, and she never forgave me for it.  She was a fabulous human.

Sex with her was very different.  It was never transactional.  Never about coitus.  It was about connection.  Touch. And we spent endless hours in her apartment on the Upper West Side, in the half light, caressing each other, arousing each other, kissing every part of our respective anatomies, touching each other inside and out, so gently, always so gently.  It was a dreamscape.  Sometimes, when I wasn’t prepared, she would send me to work in her panties.  She had a lot of them from work, and many of them became mine.  

She reminds me of the archetype, a certain kind of woman that I have been consistently drawn to.  My soul finds solace around such people, and I can identify who they are ever since I was a child.  They have always been pretty, though not conventionally so…some of my friends and family have remarked that my taste does not conform, but I think they are the most beautiful women in the world.  Put them in a room together and you would know them to be sisters, every last one of them, starting with their personalities, their spirituality, their energy.

A crutch that I fall back on in the thought of being a trans woman in bed with a cis woman is that in not having a dick, I need to be able to please her.  To think I am trading indifference to real performance anxiety.  But it’s true.  I want to go to cunnilingus school.

Unsurprisingly, there are such people out there.  I found one online who I really liked the “look of”.  I say that tongue-in-cheek, because the “look” I am looking for is a personality, not so much a physical thing.  A kind of lively energy, one that won’t be shy or nervous, but will be patient and teaching, indulgent, humorous, and mothering.  But also determined.  Determined to teach me how to please her.  I don’t know how many lessons I will need, will seek.

I didn’t contact this particular person because of how expensive she was.  I realise that escorts are a luxury.  But this is a different order.  Why?  Because of the intimacy.  If someone is going to allow you to pleasure them, they have to let you in.  It isn’t the same as doling it out.  This sometimes makes it difficult for me to be with an SW as ultimately, I crave intimacy, friendship, laughs, ease.  That said, I am very fortunate in those I have had the pleasure to connect with.  Very.

Am I like my trans friend, also afraid of the vagina?  If I am, it is an integral part of wanting one.  I feel as if the mysteries of the vagina, of the hold it has on life’s experiences and perspective, will only deepen once I have one.  And surely, my ability to love on without any encumbrance will be enhanced by having one myself.  I can’t wait to find out.