Getting Anally Fisted for the First Time Was Unexpectedly Perfect
Photo of Remy Black by Steven Thorn.


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Getting Anally Fisted for the First Time Was Unexpectedly Perfect

The idea of getting fisted for the first time was thrilling, nerve-wracking, and entirely sexy.

As a trans woman on dating apps, my quest for genuine intimacy is often bleak. I wade through a sea of chasers who share (a) secret cocklust and (b) an inability to see me as anything other than a sexual object who exists to free them from their mundane existences, by way of my transfeminine wiles and my “BBC” (big Black cock). As a power bottom, I’d wanted to explore fisting for some time, but hadn’t found a partner who didn’t objectify me, let alone whom I could trust to be patient and gentle.


I was about ready to delete the apps and enter a period of jaded celibacy when I met this guy named Malcolm on Grindr. His profile didn’t indicate a preference towards trans women. He sent face pictures upfront. Instead of asking me what kind of panties I wore or if I was “full-time,” he asked me about my favorite SZA song. My gender was never a point of conversation.

I decided to give Malcolm a chance, hoping the hour-long drive into the city wouldn’t be a waste of my time: When I wanted new playmates, I had to travel, since I lived in a secluded rural queer community in a holler outside of Nashville and wasn’t quick to bring outsiders to my sacred space. Lucky for me, Malcolm and I had instant chemistry. He was charming and Black, which was all I needed after experiencing constant racial fetishization from chasers, too. It was comforting that a partner could appreciate my Black body without making me feel exploited. He was a business nerd with a self-described dad bod—if Dad still played basketball with the boys and went to the gym regularly. He had a bald head, a bushy beard, and he looked like he could grill up some good ribs. He was an entire fucking snack.

As we got to know each other, Malcolm and I had outstanding sex—the only challenge was that he sometimes experienced performance anxiety which affected his ability to maintain an erection. I suggested that we explore touch that wasn’t centered around a hard dick. I taught him ways that we could pleasure each other using dildos, erotic massage, nipple play, and rimming, and it was really fun and intimate. After a few dates, we decided to do something special: fisting. That Malcolm was assertive enough to suggest it without knowing it was a secret fantasy of mine really turned me on. Though I was thrilled, I was a little nervous—one of my biggest reservations about fisting was that it would loosen my hole, which can sometimes happen after anal fisting. (I take a great deal of pride in my tightness, so much so that I have two daily alarms reminding me to practice my kegels.) On the day of our date, I decided I felt comfortable enough to have Malcolm over. I cleaned my room thoroughly, making sure all of my body oils and sex toys were on display, that I had plenty of clean towels, and that I’d smudged with Palo Santo. To prepare my body, I cleaned myself out thoroughly using my shower enema attachment, then took an Imodium to dry out the excess water. With a lube syringe, I injected my rectum with avocado oil, then stuck a butt plug inside me—the inside of the rectum is really absorbent and likes to be cared for just like the rest of the body, so sometimes I make suppositories with essential oils. It’s just a normal part of the way in which I care for my body. (Most people just, like…don’t clean or tend to their butt, which I find strange.) I did my moisturizing bottom routine (shea butter mixed with rose oil as a base, topped with avocado oil), made up my face with the latest FENTY, dusted myself with body glitter, anointed myself with some Florida water, and threw on a sleeveless T-shirt, black pearls, and black heeled boots. I looked sexy, but casual, I smelled like roses, my skin was smoother than a dolphin’s fin, and, when I removed my butt plug to release the avocado oil, I was pleased to see that my cleansing was surgical-grade. Perfect. I was ready to press play on my Azealia Banks fisting playlist. When Malcolm crossed the bridge into the hollow, he was thrown off that I lived somewhere so majestic and rural—we usually met in cheap hotels—and charmed by my choice of soundtrack (we both stan). While I was pleased with how considerate Malcolm had been to bring gloves, I was horrified that he’d chosen white. Not black, not blue— white, even though black latex is the glove of choice in every fisting porn I’d ever seen. (Straight people, I swear.) Before we started, I stressed that we’d need to take it slow, and that I’d guide him verbally. After we both felt clear about our expectations, we started kissing. I felt Malcolm’s devotion flow into me and sent it back to him as we fucked deeper and deeper until he asked, “You ready?” Even though he’d been pounding me relentlessly, I saw gentleness in Malcolm’s eyes. I was.


More experienced friends told me doggy-style was a good position for a first-time fistee, but facing each other seemed more intimate. I laid on a wedge-shaped sex pillow on my back with my legs pulled over my head and my knees by my ears. Malcolm put on a glove, and the whole process felt slightly surgical—I was reminded of those doctor pornos I used to watch as a kid as Malcolm injected me with an oil blend I concocted (black walnut, sweet almond, grape seed, avocado, coconut).

Malcolm very slowly inserted a finger, repeatedly asking if I was OK—which was adorable, since I’d just taken all eight of his inches for 45 minutes. I asked for more fingers and force, directing Malcolm towards my prostate. He had a little difficulty finding the walnut-shaped pleasure zone, so I told him to enter me as if he was trying to hit my belly button, which did the trick. Soon, he was vigorously massaging me with all five fingers in a twisting motion, sometimes angling upwards in a “come hither” gesture.

Getting fisted was nowhere near as painful as I suspected. Intense, yes—but not painful. We were very much working together, and it was incredibly intimate. He could feel my pulse; I could feel his bones. With his knuckles all the way inside, I wiggled to see if we could get wrist-deep, but my rectum was more of a maze than a straight tunnel. I remembered more of my friends’ advice: “You probably won’t get it all in the first time. Don’t force it.” Satisfied and feeling like I could use a break, I asked Malcolm to remove his fist. (I’m happy to report that his glove was as white coming out as it was going in.)


I was pleasantly surprised that, even after being fisted for hours, my hole quickly returned to its normal size, as I learned after we fucked some more. Knowing that I had just had 75 percent of someone’s fist inside me renewed my confidence in my alpha-bottoming abilities: I was able to relax completely, which allowed Malcolm to fuck me harder than I’ve ever been fucked. I’d never actually seen him cum—he’d made me cum countless times, but he’d never been able to reach climax. As the rhythm intensified, he grabbed my black pearl necklace as he used his free hand to jerk me off, and we finished together. I’ve had plenty of great power-bottoming experiences, but surely none as powerful as the time after Malcolm fisted me.

After we were done, I sparked up a Black and Mild and put on some Sarah Vaughan, and Malcolm and I talked about how our first-time fisting experience had gone for each of us. Malcolm said his hand felt an extension of my body. I’d felt like we were in a meditative trance, exchanging energy back and forth. It was beautiful. In the morning, we kissed farewell, hoping that our paths would cross again one day, since he was moving out of state soon after this date. (Little does he know: I’m a witch. I left my magic all over him that night—I’ll be seeing him again.)

Through my experience with Malcolm, I’ve experienced firsthand the healing space that is created through trust. Trust allowed me to invite Malcolm into my home and into the innermost parts of my body, and it allowed him to finally overcome his fears and insecurities and release himself inside of me.

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I always wondered what it would be like to get fisted. What would change? Would I recover? Would I ever be able to take dick the same again? I can now say, from the other side, that it’s just like before, except the fears that I once had have turned to desire—all that’s left to do is take a deep breath and go deeper.