What it feels like to masturbate as a trans woman

Writer Ana Valens gets intimate with gal pal about her ever-changing orgasms

Pleasure comes in so many beautiful forms, but for people that have, or are currently transitioning, it’s not as simple as a quick whizz with a sex toy – it’s a journey of self-discovery. One that can take time, focus and a whole new approach, according to Brooklyn-based writer Ana Valens. Here, she opens up about her experiences of masturbating as a trans woman, from how HRT has affected her sensations to the techniques that make her orgasm.

How have your orgasms changed before, during and after taking hormones?

My orgasms have changed a lot! Before hormones, they were strong but abrupt. I’d feel muscles contract in a pleasurable release in my pelvis, then they would disappear quickly as a mixture of relief and dysphoria as arousal washed through me (and out of me).

On HRT, orgasms are like a wave of pleasure, starting at my crotch and flowing through my body. When I come, I begin to quiver, and when I’m orgasming, my body thrashes around. I literally can’t control it. Afterwards, all that pleasure stays in my body, calming me down or even putting me to sleep. I like to describe it as an “afterglow” that lingers inside me.

Sometimes I can orgasm multiple times in a row, too, whereas there would be a refractory period before HRT – i.e. if I’m focused and in the right mindset, I can come again in an even deeper and more pleasurable wave. I’ve orgasmed as much as two or three times, one after another within an hour, and it’s incredibly intense.

Do different parts of your body have different sensations now?

Yes, definitely so! My body has become much more sensitive, specifically around my back and shoulders. When my play partners run their fingers across my sides or back, I start to squirm if they go too slowly. I never, ever had that experience before HRT. My breasts are also much more sensitive, to the point where just cupping them or fingering my nipples can be a huge turn on if I’m in the right mood.

How have your genitals changed?

It’s interesting as the changes are complicated. For one, just like the rest of my body, my penis (or “clit,” as I like to call it) is a lot softer now. It’s very sensitive to the touch and cannot sustain as much pressure or force. I can’t just jerk my bits up and down until I orgasm like I used to. I need to be really in tune with my body, how my genitals feel, how they want to be played with. During oral sex, for example, sucking motions are a total no-go, it becomes too painful too quickly.

I never have full erections any more, either. While I will get longer and slightly erect when I’m turned on from time to time, perhaps enough for penetrative sex, I simply cannot reach the full size/form that I used to before going on oestrogen. I’m perfectly fine with that, for the record. I think there’s something really attractive about trans women’s penises, how they’re both soft and delicate, yet prone to showing one’s arousal through growth and a slight hardening.

Lastly: Some trans women experience a slight atrophy with their penises after being on oestrogen for a prolonged period of time. That makes sense when you think about it: trans women on HRT are less likely to get random erections or become fully hard during the day while fantasizing, which means the penis will naturally shrink from relatively less use compared to, say, cis men on testosterone with a pretty active sex life. I suspect this has happened to me too – that is, I’ve shrunk slightly – but not by much. And it varies from person to person. I’ve been with trans women that have really small clits and others that are pretty big down there.

What stumbling blocks have you experienced when trying to reach orgasm?

I had to totally rethink the script about masturbating. Before HRT, I basically groped my penis and stroked it up and down until I came, even if I wasn’t in a very sexy mindset. Getting those few seconds of intense release from orgasming was the goal at all times. Now, headspace is everything. I really have to be ready, open, and connected with my body. I have to calm down, deprioritize orgasming as the end reward, and let my body lead the way and show me the signs. I didn’t realise all of that when I first started HRT, and I assumed I could just touch my clit the same way I did pre-HRT. I basically had to relearn how to masturbate from scratch.

What mental challenges have you faced when it comes to masturbation?

I’m a very anxious person by nature, in part because I have OCD and a form of traumatic stress disorder. So it can be very, very hard to calm my mind down and just be present. That’s honestly the biggest issue I have, and I’ve spent the past few years learning how to let go of my thinking and embrace my thoughts and feelings. It’s a work in progress, but mindfulness meditation helps a lot.

Otherwise, sometimes I become a little dysphoric during masturbation. But more than anything, the difference between a good masturbation session and a bad one is how willing I am to let go of my anxiety and just be present with myself, my body, and whatever sexual fantasy I’m having.

How about physical challenges?

The biggest challenge is just learning to listen to my body, manage expectations, and more intimately understand how my genitals work. Like I said earlier, I had to relearn how to play with my body. Learning more about the nerves inside and around my penis – and more specifically, why both the clit and the perineum should be touched during play, as they’re both connected to the same web of nerves – really changed a lot. For more info on that, Fucking Trans Women by Mira Bellwether is great.

Do your orgasms feel different, are they ever-evolving?

Hmm. I suspect the longer I’m HRT, the more powerful and intense they’re becoming. But I’m not quite sure. At most, I can definitely tell that my orgasms change based on how I masturbate, i.e. using a sex toy is a much more rewarding experience than lubing my clit and stroking myself until I climax.

What has surprised you about solo sex during your transition?

It demands your time and attention. All of it. You really can’t just mindlessly touch yourself until you orgasm. You have to be present with your body. Learning how to meditate and engage in mindfulness exercises helped me a lot in that regard. It basically taught me how to tune in to myself and figure out what I’m feeling and why.

Do you have a go-to way to masturbate now?

Admittedly, I’m still figuring it out. But my favourite so far is using a special masturbatory sleeve designed to stimulate the nerves within the penis, combined with a cock ring that stimulates both the base of the shaft and the perineum. Both amazing to orgasm with and just really pleasurable against my genitals.

Are there any toys/lubes/materials that have helped you?

I’m a big fan of water-based lube, which is affordable, easy to clean up, and means you don’t have to worry about damaging those nice silicone toys. I don’t really use it that often, though, unless a toy calls for it. Beyond that, I love kink, so anything related to BDSM helps a lot. Bondage tape, blindfolds, collars, just to name a few. That said, I’m more likely to use all of those things during sex as opposed to solo time.

What would you say to people going through what you went through? Any tips, words of encouragement, advice?

First off, I think it’s important to look at yourself in the mirror and really ask some difficult, introspective questions about your sex life. How do you think about sex? What do you want out of masturbating? Where is your head right now, and what can you do to change that? If you’re struggling to be present or enjoy yourself when you masturbate, then you may need to approach masturbation (and sex itself) in a new way. Therapy can help with that a lot, and there’s no shame in needing the guidance either.

Also, in my case, I had to mourn my relationship with masturbation pre-HRT. It was very easy and simple for me to orgasm, even if it made me feel dysphoric. When I first started HRT, I struggled to enjoy myself while masturbating, and I really wished I could experience that same easy release when I first transitioned. Now that I’ve been on HRT for a couple of years, I’ve put that part of my past behind me and embraced where I am now.

Now, I love masturbating on oestrogen a lot more than I ever did, it’s much more fun and rewarding because it feels right (and the changes to my body and orgasms are 1000x hotter to experience).

Lastly: I cannot recommend meditation highly enough. In mindfulness meditation, we talk a lot about “beginner’s mind”. That is to say, approaching day-to-day life with a playful, open approach, instead of trying to rigidly control your thoughts and feelings. That definitely applies to masturbation too. Staying open-minded, listening to your body, and being unafraid to explore yourself in new ways will unlock a lot when it comes to your sex life. Don’t be afraid to try new things, as long as you feel ready to step out of your comfort zone. Sometimes, a little push unlocks a lot of pleasure.

Oh, and before I forget: Have fun! Sex is amazing, as is masturbation. Take pride in having a body that you get to call your own and craft as your own, it’s a rare gift that not everyone gets.

Written by Claire Blackmore, @cla_ireb