Pleasing my doctor through self-pleasure

Disclaimer: this post discusses intimate details of the trans female sexual anatomy.

Does this qualify as clickbait?  I mean, most people have sexual fantasies involving their doctors.  Most women anyway.  I count myself one.

The biggest lesson of my day today is that I have been masturbating like a woman, a girl, since I first began. Began masturbating, that is.  Lots of explaining to do.

First, boys, at least any that I know, hold their erection in one hand.  They stroke themselves.  Some might use the second hand to join in the fun.  Maybe playing with the balls, but I think that most are one-handed operators.

I’ve never done that.  I can count on the fingers of one hand (hah!) the number of times I masturbated with a hand.

The very first time I got off I didn’t know what was coming.  The fresh, crisp clean cottonof my pajamas, just back from the laundry and hanging in my closet, was all that it took.  The sensation of the fabric on my skin made me, encouraged me to move my hips in a gentle way, moving, gyrating, gently pulsing until I came.

Today, under the watchful eye of a Tantrika, who was with me to teach me how to pleasure my new female body, to teach me how to masturbate surfaced these memories.  We talked at first, why I was there, and I gave her a taste of my journey, this entire blog in 1-2 pages.  I didn’t think I was emotional, but I still stood on the precipice of tears and gazed down into the purple expense of my own sorrow, teetering on the edge before turning away.

We began with the breath.  We followed with the first gentle touches of my body, my whole body, as a I lay flat on my back.  She asked me to bring in audible sighs, to connect to my inner purr, to express pleasure through gentle sound vibration, a moan.  

She guided me towards a practice of self touch.  Every so often she would touch my jaw and tell me to breathe and to release tension; or to let the energy flow into my legs, a message underlined by her gentle touch in my inner thighs; or up my belly, with a soft hand placed there.

She taught me to open my legs in a tantric way.  Soles together, legs open like a frog.  I placed my hands on my vulva and felt them there.  She taught me several hand techniques, showing on her body and watching as I repeated.  And I made myself feel good, really good, moaning on the futon on the floor of her sitting room.

It was a beautiful experience, made more so when she settled in between my legs and replaced my hands with hers.  I learned what I like.  She suggested I leave behind the vibrators for a while…likening them to a sugar high…and that we can become addicted, so it is better not done.  At least until I have taught myself to pleasure my body.

She asked me to say out loud what I was doing to myself, and when I see these words I felt a rush of pleasure, and the deeper breath followed.

“I am running the length of my fingers along the shaft of my clitoris.”

“I have my hand cupping my vulva.”

“I am teasing my labia with my fingers.”

“I am resting my middle finger at the entrance to my vagina.”

She explained that men move their hand when masturbating, but that women move their bodies, their pelvis, their hips, their whole bodies.  She guided me into this practice, and it was at this moment that I realized how this is how I always masturbated.  By moving a bit like a snake, slithering and wriggling across my bed.  It took me into head and body space I have always had, but have forgotten since going onto HRT almost three years ago, and later in surgery.

She had me gradually rest my finger on my introitus, on the opening to my vaginal canal.  

“Don’t push it in,” she guided, “let your hips go and get your finger.”  I did this.

She asked me to describe what I was feeling in my body as we went.

“I feel as if my body is a vessel of water, gently moving back and forth,” was how I described the sensation at the very beginning.  After, it was more about the specific sensation of touch, or of being touched.

She had me touch myself with my hand when it was my hand seeking and experiencing pleasure.  She had me touch my body again, this time with my body seeking and experiencing pleasure.  She asked me to observe the differences.  My hand went to different places, my body behaved and responded differently each way.

When my finger was inside me, she asked that I sway my hips so that my fingers, holding still, might wipe the inner wall of my vagina.  She asked how it felt.

“I am reminded of what my doctor wants me to do.  This helps prevent scarring and reduce the stiffness of scars.  It is important to massage the seam from where my vaginal canal meets my vulva.  My doctor would be happy.”

“That’s very good.  But I want you to create a different pathway.  That one is a therapeutic pathway, but this is a pleasure pathway.  Think about what is happening now, that you are doing it because it feels good.”

We did this wherever and whenever I was pulled by “Doctor’s orders” and pleasure.  

“This is a regular practice, not just one and done,” she said.

“I know.  My doctor wants me to do it every day when I dilate.”

“Me too, but instead of doing it after you dilate, or during, I want you to take your pleasure practice for 10 minutes before you start.  Every day.”

And that’s how we left it.  She will be co-facilitating a 5-day Tantric immersion that I am attending, but I will see her again in a month.  And I will see one of her colleagues in 10 days.

2024 was a big step for me in my body.  2025 will be a different step, but also in my body.  Only this one, in a strange way, seems more momentous.  For someone who spent their entire life avoiding touch, avoiding intimacy, I am called to Tantra, to my body, as it helps me to understand and live inside my skin in a more feminine way.  There is nothing more important.

See you on the other side.