The neon lights of Las Vegas danced in my eyes as I sat in the dimly lit hotel bar, nursing my whiskey. I was in town for a business conference, but the night was young, and I was feeling restless. My gaze wandered over to the bustling crowd when a familiar face caught my eye. She was sitting at the end of the bar, sipping a cocktail, her red lips curved into a playful smile. I recognized her from the dating app we’d been chatting on earlier in the day. Her profile name was Stef, a stunning woman with a body that could make any man drool.
I walked over, extending my hand. “Devin,” I said, my voice low.
She looked up, her eyes meeting mine, a spark of recognition in them. “Stef,” she replied, her voice as smooth as velvet. “You’re just as handsome as your photos.”
“So,” Devin said, flashing a grin. “It’s great to finally meet you in person. You look just like your profile picture.”
Stef smirked and took a sip of her drink. “Thanks. And you… kind of look like yours.”
Devin let out a nervous chuckle. “Yeah, well, I might’ve used a photo from a few years ago.”
“How many years?” Stef asked, raising an eyebrow.
Devin shifted in his seat. “Okay, so the iPhone I took it with is now considered ‘vintage.’”
Stef shook her head with a laugh. “At least you didn’t send me a picture of a yacht and pretend it was yours.”
“No, but I did rent a jet ski once. That’s kind of the same thing, right?”
“Only if you didn’t fall off,” she teased.
Devin hesitated. “Define ‘fall off.’”
Stef laughed and shook her head. “I had a feeling you were trouble when your bio said, ‘Professional Risk-Taker.’”
“Hey, that just means I ordered the seafood buffet here once and lived to tell the tale,” Devin said with a wink.
Stef raised her glass. “To survival, then.”
Devin clinked his glass against hers. “And to slightly outdated profile pictures. Sorry about that, by the way.”
“Don’t be, I prefer this more distinguished mature look. I like an older man.”
As they drank, the slot machines behind them erupted into a chorus of jingles, as if giving their chaotic life choices a round of applause.
We chatted for what felt like hours, but it was actually only around thirty minutes in and she suggested we continue our conversation in my hotel room.
Once inside my suite, we fell into each other’s arms, our lips meeting in a hungry kiss. Her mouth was soft, her lips full, and she tasted like fruit and desire. I explored her body with my hands, tracing the curves of her hips, the swell of her breasts. She moaned softly, her body pressing against mine.
“You’re so fucking hot,” I growled, my hands roaming down to her ass, giving it a firm squeeze.
“And you’re so handsome, daddy. I can’t wait to see how you’re going to make me feel like a woman, daddy.”
The true meaning of that statement didn’t hit me til a few moments later when I watched, as she revealed her body, her soft skin, her perky breasts and to my surprise an erect penis hard and straining against her lace panties. Ahhhh…”Feel like a woman” …ok, I get it now. Hmm, me being a bit more mature than my pictures represented didn’t feel like quite as big of an omission now.
“Oh wow,” I said, speechless, “You’re a….”
But before I could continue and potentially stick my foot in my mouth she interrupted said “Your turn,” her eyes never leaving mine as she unbuckled my belt and slipped my pants down. My cock sprang free, already rock hard. I was into this. It was a surprise, but I was into it.
She licked her lips, her eyes gleaming with desire. “Mmm, you’re big,” she purred, her hand wrapping around my shaft.
I groaned, my hips bucking at her touch. “Not as big as you,” I said, my eyes on her cock, my hand replacing hers.
She laughed, her hand joining mine on my cock. “Let’s see about that,” she said, her mouth capturing mine in a fierce kiss.
We rubbed our cocks together, our bodies pressed tightly, our moans filling the room. The friction was intense, our pre-cum mixing, making our cocks slide easily against each other.
“Fuck, Stef,” I groaned, my lips moving to her neck, sucking and biting.
She gasped, her hips moving against mine. “I want you inside me,” she whispered, her hand leaving my cock to slip between her legs, rubbing her own.
I groaned, my cock aching with need. I pushed her back onto the bed, her legs falling open, revealing her hard cock and her smooth, wet asshole. I licked my lips, my eyes on her, my cock throbbing.
I positioned myself at her ass, my cock poised at her entrance. I spit on my hand, using it to lubricate my cock, then slowly pushed in. I could tell she had prepared for this, her asshole was tight but felt as easy to penetrate as a pussy.
She gasped, her body tensing, her hands gripping the sheets. ” Fuck, that’s big,” she groaned, her body relaxing into me.
“You can take it,” I said, my voice rough with desire. I began to move, slowly at first, then faster, harder, my cock sliding in and out of her tight ass.
She moaned, her body moving with mine, her own cock rock hard and leaking. “Faster,” she gasped, her hands reaching down to stroke her cock. “Fuck me harder, Devin.”
I did as she asked, my hips slamming into hers, my cock pounding her ass. The room filled with the sound of our bodies slapping together, our moans and groans of pleasure.
I could feel my orgasm building, my cock throbbing with each thrust. “I’m going to cum,” I groaned, my body tensing.
“Cum in me,” she gasped, her own body tensing, her cock pulsing in her hand. “I want to feel you cum inside me.”
With a final thrust, I unloaded a huge load of cum, my cock pulsing as I unloaded deep inside of her ass. She moaned, her body convulsing as she came too, her cum shooting out onto her stomach.
We collapsed onto the bed, our bodies slick with sweat, our breaths coming in ragged gasps. I pulled her into my arms, our bodies pressing together, our hearts beating as one.
She never said anything further about how I hadn’t realized the nuances of her gender identity until her clothes came off, but I imagine she had a sense of how things would unfold from our conversations and the way we connected at the bar. Besides, neither of us had been completely forthcoming that night—I was a little older than my profile claimed, and she was a transwoman. But in the end, it was a night worth remembering—unexpected, exhilarating, and utterly delightful.