How a Rim Job Helped Me Realize I'm Trans

Cosmopolitan

03-06-2025

I was a 19-year-old gay man and I needed to get laid.The previous summer, I'd had the best sex ever: fumbling, sweaty, with a repressed Christian in a humid minivan. He'd clawed off my damp top and I'd breathlessly moaned, 'Suck on my tits.' We shared only a millisecond of confusion (I had no tits to suck) before the momentum of our lust propelled his mouth to my nipples. Initially, I chalked it up to nonsensical babbling in the throes of pleasure, but something about it felt right.
Unfortunately, I'd had only a few opportunities to further explore my newfound love of sexual feminization since then, calling my asshole a 'pussy' and my dick a 'clitty' when chatting on Grindr.
Enter that lifeline for rural sluts everywhere: Man on Business Trip.
According to his Grindr profile, Jackson* was 6'3", with shoulders as wide as a fridge and arms like swollen hams. With his towering stature and warm complexion plus an incandescent smile and a bald head, he resembled The Rock.
My heart pounded as my headlights illuminated the cheap lodge where he was staying. I followed his directions to a side entrance where he met me at the door looking, miraculously, even better than his pics. His dark eyes shone with kindness and his baritone chuckle reverberated through my rib cage as he described his profession and the presentations he had scheduled for tomorrow. He turned to guide me to his room, his T-shirt stretched taut like a canvas across the vast expanse of his back. The blood pounding through my ears nearly drowned out his voice as he opened the door to his room. 'My job always tries to put me up in ritzy hotels,' he explained. 'But I prefer these mom-and-pop places outta downtown. Better food out this way anyway.'
He waved me inside with one of his gargantuan paws as we performed that cordial ice-breaker conversation that precedes all hookups, particularly those between internet strangers. Meanwhile, I silently celebrated securing a rendezvous with a man so convivial and also physically massive, so visibly strong.
I'd always gravitated toward men who looked like they could break me in half before grinding my bones for bread. Their mass made me feel small, dainty, and safe—yet somehow, it also frightened me. So even as I casually commented on the room—with its peach walls and glass-block window, its smell of soap and dried flowers—I made mental note of any blunt objects I could use to defend myself if shit went down (as if I were some kind of twinkish John Wick?). And even as I smilingly accepted his invitation to lie side by side on the bed, Juju Chang's steady newscaster narration rang through my head: Tonight on Nightline: 'Grindr Gone Wrong'—a sadistic traveling killer and the stupid horny teen who went to his hotel.
'God, you're cute,' Jackson said in that deep voice.
I smirked. 'You too.'
Then we leaned together and kissed. Potential psycho killer be damned.
The softness of his lips and tongue clashed with his daunting stature—an arousing dichotomy. We rose from the bed, making out as we undressed. Dichotomy again: my slim, pale, hairy torso pressed against his smooth, bronze, beefy body. With one of his dining-plate-sized hands, he cupped my cheek and I moaned into his kiss. In one fell swoop, he picked me up and cartwheeled me in his arms so that his hard cock grazed my eager lips. I gasped as he began sucking my dick, his low groans of delight vibrating through me from root to crown as I began swirling my tongue around his pink head.
A few minutes later, he laid me down on the coarse floral bedspread and folded my legs to my chest, propping my ass up with a pillow so he could admire my tight little rosebud. He licked his lips like a cartoon character before diving into the feast.
A whimper escaped me as he began devouring my asshole with a methodical insistence typically reserved for dogs trying to get peanut butter out of a chew toy, my heart rate increasing every time that soft tongue pushed into me. He gently grazed his teeth across my ass cheeks and I shivered, biting my lip. My whimpers only increased, rising in pitch as he sucked on that bit of flesh where my hole met my taint.
This was peak.
'Just like that,' I sighed. 'Eat my pussy, Daddy.' He growled and sucked more fervently. My neck arched back and I cried out—not only from waves of novel pleasure but also from waves of gender euphoria as I saw myself: flat-chested and hairy, yes, but long-haired and somehow also feminine, enjoying a sexual position most commonly enjoyed by women receiving cunnilingus.
This hookup is anchored in my memory like an eye in a storm of dysphoria. It was the first time that I wondered—however fleetingly—if feminization wasn't just an enjoyable sexual practice but maybe an intrinsic part of myself.
Great sex can discombobulate you so thoroughly that you momentarily forget the performance of the self so many of us are usually putting on—in life and in bed. It can strip you down to your raw, authentic core. So we cry out, 'Oh, Josh!' when we were supposed to say 'Gabriel.' So we mumble, 'Suck on my tits,' when otherwise we'd have said, 'Suck my nipples.' And as we reach between our legs with trembling hands to caress the smooth head of the man eating our ass, we briefly think, This dude should be eating my vagina.
I didn't ejaculate in a masculine, staccato burst. Instead, I experienced one of the most intense orgasms of my life—wave after wave after wave, legs shaking in the air as Jackson's insistent tongue pushed me over the edge. I was so overwhelmed that I finally had to set my soles onto his shoulders and push him away to give myself a break.
Now, years later, as my bottom surgery awaits just months away, I fantasize about finding a guy as orally talented as Jackson to feast on my new pussy—the way it should be.
*Name has been changed.