My Therapist Called Me a ‘P*ssy’ so I Tried Anal Sex

After, I came out to my mom as trans.

By an Anonymous Boyslut

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Original illustration by Tara Savelo

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When I give myself the shot, I usually do it in the soft part of my stomach. It’s easier to grab a pinch of fat there below my navel than try to reach a buttcheek, twisting my body around like a statue of a Greek boy about to throw a discus. I want to be big; I want to be hairy. I’m nearly tall enough, and my body’s athletic, but after six months of T, my face is still as downy and soft as a baby’s bottom. (After a black-tie wedding in Manhattan a few years ago, I was at an afterparty at The Carlyle. Next to me at the bar, an older man waiting to order a drink looked at me in my tuxedo and said he didn’t believe I was old enough to be there. “What are you? Nineteen years old? Your beard hasn’t even come in yet.”)

Last week, with my baby’s bottom face, I asked my partner if they would give me my shot since it stings when I insert it in my stomach, and I can barely feel it when someone gives it to me in the ass. We were standing in our bedroom near the door to the bathroom, next to our waist-high wooden dresser. I had a small syringe in my hand filled with the amber serum and a couple of alcohol wipes.

“Alright, bend over, elbows on the dresser,” they said. 

“Oh that’s okay, I’ll just stand and pull these down.” 

I jutted my hip out slightly as I tugged down the waistband of my sweats. Leaning against the doorjamb, I pulled up my shirt from the side, then slid my sweats and boxer briefs lower so that the top curve of my butt was exposed. 

They repeated, this time firmer, “I said, ‘Elbows on the dresser.’” 

Meeting my gaze, they wanted to play with me. They started to push my spine down to bend me over the dresser. (We’d been together for seven years, and I rarely let them top me.) I stiffened and declined their bid, not wanting to play naughty doctor or whatever they had in mind. 

I was a bit cranky now and short, growing tight. “C’mon, just give me the shot. I don’t need to bend over; give it to me like this,” I said. 

Slightly deflated, they grabbed a small handful of my butt towards the outside of my hip and swiped it with alcohol. Just as they were about to insert the needle, I yelped and shouted, “No!” We tried again and again, but each time, I couldn’t take the pain. When I tried lying face down on the bed, still clothed except for my pants pulled down to my knees, the same thing happened. I couldn't relax enough to take the shot. 

I ended up giving the shot to myself a few hours later.

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The next day, I sat on the couch in my therapist’s office and told J what happened, how I suddenly became completely unable to take the smallest of pricks in my ass. J is forty or fifty or a gazillion with sandy curly hair and a short grayish beard. He mostly dresses like a therapist or someone playing a therapist (I mentioned this to him one day, trying to neg him about his cardigan. He responded that it was an “occupational hazard.”). 

We moved quickly through the arc of the 50-minute session, and so many pieces came into view at once. We talked about how I never let my partner initiate. We talked about how controlling and critical I can be about how they touch me, how they want to experience sex with me, and how I don’t let them set the scene or be playful in their own way.  

“You’re a pussy,” J said towards the end of the session, imagining what I might believe about myself if I risked anyone seeing me bent over and fucked from behind. This made me blink with recognition, a little stunned to hear him say this, but then I replied, “Yes, exactly.” 

After all this time being with my partner, having a strong bond, having sex with other people together, living together, etc., J wondered if I still didn’t trust them—or was having sex with my partner as if I didn’t trust them. 

"What if you could relax your grip and see what happens?" he asked. 

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Later that night, I asked if my partner wanted to join me in bed. We started kissing. For the first time in a long, it felt like we had possibilities. We just needed the courage to choose one. I impatiently tried to get their clothes off, but I also couldn’t stop grinding my clit on their thigh. I had one hand on their nipples, pinching hard, making their breath catch.

“I was wondering if you wanted to fuck me against the dresser?” I asked as my eyes narrowed. “I think I missed my chance the other day.”

They strapped up, cinched the soft black leather through the buckles tight across their hip bones for a snug fuck. Their cock for the night was my cock. The cock we bought together. (On the drive to LA, we had stopped in Oakland to get some pizza. A few doors down was a sex shop. As soon as we walked in, something caught my eye: a cock with balls and an anatomically-shaped head. We left the store three minutes later with the unmarked white gift bag.)

I stripped down, bent myself over the dresser, and waited—my legs spread apart—my back arched upward to present my holes. I could tell that they were excited about this turn of events, and by “they,” I mean “me,” and by “this turn of events,” I mean: I was aching to be fucked.