Discovering a new sexuality as a transwoman: CONTENT WARNING

CONTENT WARNING: This is going to be an intimate dive into male-female sexuality. It will be explicit in nature.

Back when I was still burdened with functioning male genitals I used to believe women who said they could go months without sex or masturbating were lying. Being stuck in a sexually mature male body meant one thing, sex was quite frankly on my mind all the damn time. Based on conversations I have had with cishet guys and what we know from our sex-craved culture, yeah it musta been on every other guys mind too. It sucked by the way.

I was a virgin. A male virgin who grew up in a state with legalized prostitution. This meant I was surrounded by sex all the time. Nearly everyone I knew was either having sex, or watching other people do so on their computer screens. Yes, I did masturbate myself. I did it three times a day. My sex drive was insatiable. I hated it too. I was disgusted by it. Sure it felt good physically but inside I always felt bad. Not guilt for enjoying something that is absolutely perfectly natural. My guilt was enjoying “guy sex” and fantasizing about women in sexual scenarios. As someone who secretly wanted to be a woman, this offended me to my core. Yet come erection time I was right there not giving a shit.

I got started fairly early. I was 11 the first time I fingered a girl. She was, not 11 unfortunately. I chalked it up to kids being kids. It was, well as consensual kids can be. Legally speaking it was probably not but she was down so I did what she let me do. Jerking off actually came later. Not later that day later in life after I matured a little bit. Why was I compelled to do that particular deed that day? Honestly I’d rather not divulge that just yet.

I was 12 when I discovered if I rub things long enough something magical happens. And hey let’s be honest masturbating, like partnered sex, is magical. It feels fucking great. We all know that. What we don’t all know is how to control our urges or how to be respectful to others around us. That we have to learn. I learned to avoid social situations for a number of reasons. One of which was my extremely discomforting mixed feelings of sexuality. I didn’t want to be gay but I wanted to suck a dick. I wanted to be a woman but I also wanted to keep my functioning penis because it gave me pleasure to explore it. Let’s be real it feels good damn it.

So whenever I would hear a woman on TV tell a guy she could hold out for months if she wanted I either thought women don’t really enjoy sex, which made me feel sorry for them frankly, or they were lying to control men. In my mind there couldn’t be any other explanation for that. Once my sisters and other female friends confided in me their sexual pleasures I started to realize girls do like sex. Making friends with a lesbian girl taught me a lot about how much they can enjoy it, apparently more so than men allegedly. 

Now I previously stated my masturbatory explorations often included anal stimulation. I discovered I could have vastly more intense orgasms if I went to town in the back door first. Sometimes the ejaculation would just be the finale not the climax itself. Yes, I could climax without even bothering my penis. Not often but it would be done. I found this quite enjoyable to be honest. 

I started HRT one year ago last month. The first few weeks I kept on keeping on. Lying in bed, day-dream I was a girl getting nailed by some hot dude and fall asleep with wet, sticky underwear. Nothing changed. Then a few months in I started noticing my morning wood was gone. It took more stimulation and a great effort to get an erection. I could still finish but it was dry. Nothing came out. I rather enjoyed that to be honest because it was less messy. Then about 5 months ago it just stopped working altogether. I can rub but it refuses to get hard. I can kinda feel stimulation but I can’t climax that way anymore. And I couldn’t be happier!

Remember when I said I did anal stuff. Well since losing my male sex drive the first thing I learned is women were telling the truth. Sex is the furthest thing from my mind now. I am free to think about my writing or to work on a puzzle or even build a model kit and I am not doing these things to distract me from a nonexistent sex life, I am just doing things I enjoy minus the pressure to cum. 

It’s been great! I have met asexual friends online who shared similar stories of despising their male sex drive and being thankful once it was gone. I have no clue what it will be like once I get my bottom surgery and can have sex as a woman. I can tell you this, backdoor stimulation still gets the job done but like those women on TV, once every couple of months is more than enough to hold me over. I no longer need, or even want it, daily. Yes I say freed from the burden of male sexuality because ladies, it really does suck constantly trying to push sexy thoughts out of your mind 24/7. Is it okay to think about sex? Sure, as long as you do so respectfully. It’s even okay, perfectly fine in fact, to enjoy sex. As long as it is mutually consensual. 

What I learned beginning my journey to become fully the woman I always envisioned myself as is this, woman can and do enjoy sex, just in a vastly different way than men. Having experienced both I can tell you this, guys do in fact have the short end of the stick, lol. That being said. I am happier now with my sexuality than I ever have been before. And quite honestly as great as jerking off and ejaculating felt, I am glad I don’t have that burden anymore. It’s quite a relief for me. I can’t wait to see what it feels like once I have my female genitals. 

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Stephanie Bri

A transgender writer who also does podcasts and videos. If you like my writing please consider helping me survive. You can support me directly by giving money to my paypal: If you prefer CashApp my handle is @Stephaniebri22. Also feel free to donate to my Patreon. I know it's largely podcast-centric but every little bit helps. Find it by going to, Thank you.