By 
Asher* snatched up the panties I’d just taken off and put them on. Confused yet enthralled, I watched as he slid a foot into each leg of my silken underwear and pulled them up his thin, hairy thighs. The pink satin sat in peculiar contrast against his sinewy boy bod. Snapping the elastic band against his skinny hips, he gave me an impish grin like he was daring me to rip the fabric off him.
Never. Yes, Asher had shocked me by slipping on my underwear, but goddamn did he look hot in it. The tip of his cock peeked over the top like a shiny plum just begging me to reach out and grab it.
Let me rewind to explain how this case of carnal cross-dressing came to be—on our very first date, no less. We had matched only a few days earlier on a dating app—it doesn’t really matter which one, because they were all new terrain for me. I’d just started meeting men again after the end of a decade-long nightmare of a relationship and was eager for connection, but my dating muscle was out of shape.
I had a few false starts, the first with a man who wanted phone sex but hung up on me before I could diddle myself to climax. The second fiasco was in person with a guy named Jack*. But if I wanted Jack to jill me off, I was fresh out of luck. An aspiring but depressed comedian, he was on too much Lexapro to get it up. Next was a dude who showed up to our first date looking 20 years older than his profile photos. I like a Daddy as much as the next aspiring slut, but lying was a deal-breaker. Then came a man who was down for some Netflix and chill, but after Netflixing and chilling between his sheets, he began to cyberstalk me. I swear I found myself wondering what happened to the “fuck and chuck” guys of my younger years. Please, for the love of god, just ghost me!
I was close to folding up my dating flag and retiring to nights alone with my vibrator when Asher appeared in my spread. But should I swipe right on him? He wasn’t my usual type. With a slender frame, pale complexion, and jet-black hair falling over piercing blue eyes accentuated by a smudge of kohl, Asher looked like he probably still slept on a twin bed at Mom and Dad’s in a room crammed with vinyl. (He didn’t. He lived on his own, but his bedroom was chock-full of records.)
He was 23 years old, at least a decade younger than me, and I wasn’t exactly a cougar. I usually dated older guys who were a bit more...manly. Asher didn’t exactly strike me as someone who could wrestle a beaver with his bare hands. But maybe he could pleasure mine?
One of the last photos on his profile convinced me to swipe right. He posed in tight jeans barely concealing his huge bulge. The eyeliner brought out his features. Maybe I had a thing for androgynous men after all? I’d always drooled over David Bowie in his heels, just about any hair band from the ’80s (looking at you, Mötley Crüe), Harry Styles in his feather boas and pearls. A man confident enough to go a little femme with his clothing choices hinted at a radical streak he’d bring to the bedroom, right?
Fine, I’d talked myself into it. And with a right swipe and a few messages, we made plans to meet. Asher confessed he was only looking for a hookup. No prob. I’d just escaped a toxic relationship, and the last thing I wanted was to lock myself into another commitment. We decided that if we liked each other, we’d go back to his place after coffee. Clearly, the attraction was mutual; after a bit of flirty banter over our twin cappuccino orders, we did just that.
As we quickly undressed, I took off my panties—and that’s when Asher put them on. The move stunned me. But something about the way his thighs extended down from the pink satin triangle covering his stiff shaft left me surprisingly aroused.
I touched his silky bulge through the smooth fabric, noting the slipperiness of both the material and his cock—the fabric with its synthetic slickness and his schlong drenched in pre-cum. Massaging the wetness seeping through the front of my panties, I reached inside to fondle his dick. The act of reaching inside my panties on his body delighted me with its sheer incongruity. Countless men had carried out this action with me, reaching to search for my sluice. Now I was doing the same to a man in my panties! It was a mindfuck, one that excited me more and more by the second.
Grabbing Asher by the hips, I swung him around so his backside faced me. Seeing the thong butt-flossing his tight bottom, I thought about how different his muscled glutes looked from my own round, plushy derriere, the stark contrast turning me on. I turned him back around and, dropping to my knees, wrapped my arms around his ass, pushed aside the fabric to reveal his cock, and stuffed my mouth full of it.
Bobbing up and down, I tasted the metallic saltiness of his pre-ejaculate. I hawked up more spit to cover his dick and his shaft slid even more easily in and out of my mouth. As I continued to suck, I wrapped my fingers around the thong between his butt cheeks like it was the Ariadne thread that would lead me to carnal bliss. But I didn’t need any leading; I was already there.
Using the string of my underwear like a leash, I guided Asher to his bed. That’s when he tried to take them off. Not a chance. He’d put them on, and now I wanted him to fuck me in them. Really, I wanted him to do what other men had done to me, sinking into me while I still wore my underwear. I lay back on the bed, spread my legs, and pulled him to me. His sword slid right into my sheath.
When he was balls deep inside me—so deep, he tickled the apex of my vaginal canal—I reached my bliss point. Staring up into his kohl-lined eyes as he fucked me from above, I watched his sweat drip down to further smudge his eyeliner, giving him serious smokey eyes. Releasing hold of the thong, I clutched his flexed ass with both hands and, using his butt cheeks like a handle, I guided him to fuck me even faster. I’d thought that putting my panties on demonstrated Asher’s creativity. What it really did was unlock mine.
Within minutes, we both climaxed—highly unusual for me as I’ve often had trouble reaching orgasm with men I didn’t know very well. But something about the unexpected novelty of this strange little sexperience shook out all my inhibitions and made it possible for me to cum buckets, even during a first-time hookup.
Afterward, we relaxed in post-orgasmic bliss, and I finally let Asher take off my stolen thong. But as he handed it back to me, I realized it was now unwearable, the elastic stretched to its breaking point during our erotic calisthenics. I wouldn’t throw out this overworked undergarment though. It would forever serve as a memento of this experience. Anytime I needed to be reminded of how good app dating could be (even with all the bad), all I had to do was reach for the panties.
