100 Things to Try When I Have a Vagina

The words "hot trans summer" in pink and orange gradient.

Hot Trans Summer‘ is a series of essays documenting the complicated pleasure of being trans, curated by our trans subject editor Xoai Pham.


Of all the unexpected changes I encountered during my transition the most surreal had to be transforming a part of my body. I began my transition in 2018 at the age of 31. If you’d believe it, until then I hadn’t the faintest notion of my identity. I was relatively happy in my body and felt myself a satisfied, sexual person even before surgery.

In hindsight, it was all a little formulaic: privacy, porn, and pleasure. I would engross myself in the pleasure those women must be experiencing. Only later would I realize it wasn’t that I wanted to be with those women, I wanted to be them.

Before I endured my surgical crucible, my excited energy inspired me to start a list: 100 Things to Try When I Have a Vagina.

The entries were mundane at first.

1. Wear a bikini bottom without worry.

2. Ride a bike. (I had hoped for relief from squashed testicles, but I didn’t realize quite how connected I’d be with anything I sat on!)

3. Try a ‘rabbit’ vibrator. (It turned out to be a quick favorite!)

While many of my entries were things I would literally insert inside me, I soon realized others were yearnings to experience pleasure with my new body in the open:

13. Sex on the beach!

29. In a tent!

33. In the backseat of a car!

Heck, even #35, in a public restroom, stands out to me now as less sexual, and more about the freedom to connect with others.

By some miracle, my originally scheduled date fell between waves of COVID. Before I could even get to #69, surgery was upon me. I’d get my chance to finish by a frightful and ironic doctors’ order: two months of celibacy.

My journey in the year since has been full of joyful surprises and serendipitous discoveries. While I don’t have room to share them all, I hope you enjoy a few of the 100 Things” I’ve tried.

6. Find my G-spot, 7. And make it sing.

My new experience of penetration was something entirely different from what I experienced before. As swelling faded and my pussy healed, clinical requirements to frequently dilate eventually led to feelings of sexual fullness. Even without movement, it just felt good to have something inside me. (Which is a bonus, as I would spend nearly 12 hours a week in such a state during early recovery!)

17. “Go Fuck Myself”

One of my most pressing concerns leading up to surgery was preserving my former anatomy. Despite my best efforts and multiple attempts, I wasn’t able to “clone” myself.. It had been over a year on hormones. and my self-confidence had taken a dip. My sexuality was starting to emerge–I knew that I desired a feeling of fullness, but only wishful projection and a prescription for Viagra would have to suffice.

As luck would have it, I met a local caster with experience making custom intimate molds. I’ll never forget the experience of a stranger slopping and corralling casting mud over my genitals until it hardened into an amorphous blob. The mud was cold, earthy and grey. We made inconspicuous small talk, all while I desperately tried to squeeze out any last bits of courage my soft, feminized member could muster.

After my surgery, I received my clone, and I was immediately struck by how alien it looked. “Did you make any alterations?” I inquired. “No, it’s a perfect copy of your former self.” I rushed home for time alone. It was striking to experience myself, finally comfortable in my own skin.

4. Have a clit orgasm

You should know healing is a spectrum, not a set of milestones. This was made clear to me after three months, when I discovered that what I thought was my clitoris was in fact just its hood. As my swelling diminished, I saw her peeking out and I quickly learned the difference! There beneath lay the most gorgeous little nub, shiny and taut like the tissue of my glans I remember from before. She was now outstandingly sensitive, and masturbation became an exercise in control.

Where before I could give in to my pleasure and ejaculate quickly, the feeling of orgasm now took time and patience to achieve. My efforts would be rewarded. What once felt like a splash, was now a raging tide. Instead of rushing out of me, I felt that same hot ecstasy wash over me from head to toe, feeding my soul.

??. Squirting!?

The most dubious item on my list was squirting. I’d heard it was possible, but I tried to temper my expectations before surgery. Never did I expect to have my own experience to contribute.

Little did I know, my sexual awakening would present a whole myriad of new orgasms to me, two of which included squirting!

I spent hours pondering “what, where and how”. Although I no longer had testicles, coming to an orgasm left me notably wetter and sweetly odorous. As it turns out, I still possessed fluid-producing tissues, further enhanced by years of hormone therapy. Having been satisfied I wasn’t alone in my experience, I settled that it didn’t really matter, physiology was fascinating and it was a joy to explore. Not only does my body produce ejaculate (thanks clit!), but it was possible to squirt-squirt with just the right stimulation (thanks G-spot!).

101. Love Thyself

Most strikingly, COVID and “100 Things” gave me the space to develop a relationship with myself. At the outset of my journey I was searching for somebody to love. I spent countless hours trying to figure out who I needed to be for someone else. Isolation directed me inward, and in solitude I was forced to reckon with the possibility of loving myself both inside and out. I learned to spend that same time on myself and suddenly felt myself steady against life’s ebbs and flows. Finally, I could thrive. Finally, I saw me.

This can not be overstated: learning to love myself first and foremost was one of the most important lessons I learned undertaking “100 Things.”

Everyone’s transition is different, but I know for me July 1st, 2020, was the day mine was complete.

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5 Comments

  1. Before I had surgery a decade and a half ago I too would dream of all the things I would do. It took a while after the operation for sensation to return, and I don’t have much of a sex drive anyway, but when it did boy was it amazing finally feeling pleasure from sex. Apart from how wonderful it can be to have a vagina and to experiment getting to know my clit, the absolute best thing was something you might not think of and which I still think of everyday. And that’s the comfort of having your body match how you preceive it in you head. Every time I take a shower, or bath, or go swimming, or visit visit sauna, or sleep with someone, or go to the loo, I’m just overwhelmed with the calm and joy of having a body that just feels right. Best of all, lying in bed naked with fresh sheets over me, and not feeling the slightest hint of dysphoria, utter bliss.

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