Alex paced the dimly lit hotel suite, his heart hammering as the clock ticked toward midnight. This was his first time with a trans woman, and the escort app had matched him with Elena, whose profile promised sharp wit and no boundaries. When the knock came, he opened the door to find her standing tall in a sleek black dress that hugged every curve. Her eyes sparkled with mischief. "Nervous already?" she teased, stepping inside with confidence. "Most guys chicken out before the door closes."
Elena set her bag down and turned, sizing him up with a playful smirk. "First time, right? I can smell the virgin energy from here. Don't worry, I'll make it worth the sweat." Alex laughed, tension easing. "And here I thought I'd be the one calling the shots. You seem like you run the show." She stepped closer, her perfume intoxicating. "Smart boy. But let's see if you can keep up when things get hard."
They shared a drink, the conversation flowing with witty barbs. "So, bareback on the first date? Bold choice," Elena said, her hand brushing his thigh. "Most clients want the wrapper. You must be feeling extra horny tonight." Alex met her gaze. "I trust the tests you mentioned. Besides, I want to feel everything—your ass gripping me, no barriers." She chuckled, strong and unyielding. "Good. I don't do submissive. You'll fuck me, but on my terms. No switching."
Elena pulled him into a kiss, her tongue demanding as her hands roamed. Clothes fell away, revealing her toned body and the hard cock between her legs, already twitching with interest. Alex's own cock stiffened at the sight. "Like what you see?" she whispered, stroking herself lightly. "Don't get ideas—tonight, you're the one doing the fucking. My pussy's tight and waiting, but this cock stays out of you."
She dropped to her knees for a teasing blowjob, her mouth warm and skilled around his throbbing cock. Alex groaned, fingers in her hair. "God, you're good at that. Keep going and I'll cum too soon." Elena pulled back, lips glistening. "Not yet. I want you panting and hard inside me first." She stood, pushing him toward the bed, her strong presence guiding without submission.
On the sheets, Elena positioned herself on all fours, ass raised invitingly. "Lube up and slide in bare. Feel how wet and dripping I am for you." Alex complied, his cock pressing against her tight entrance. He thrust slowly at first, building rhythm as she moaned. "Deeper, damn it. Make me feel that hard cock stretching me." Their bodies moved together, sweating under the strain, her witty commands spurring him on.
"Faster—fuck my ass like you mean it," Elena demanded, her voice sharp even as pleasure built. Alex pounded harder, one hand on her hip, the other reaching around to stroke her cock lightly. She was panting now, dripping with need. "Don't stop. I'm so horny, but remember—no fucking me back. You came here to take me, so do it."
The pace intensified, skin slapping as Alex buried himself deep. Elena's strong frame pushed back against him, controlling the angle with powerful hips. "That's it—fill me up. I want your cum inside." He felt her clench around him, her own cock pulsing untouched as she came with a cry. The sensation pushed Alex over; he thrust once more and came hard, flooding her bare ass with hot cum.
They collapsed, bodies slick with sweat, panting in the afterglow. Elena turned, a satisfied grin on her face. "Not bad for a first timer. You followed the rules—no letting me fuck you. But next time? We might negotiate." Alex smiled, already wondering about the possibilities ahead. "You're stronger than I expected. This was just the beginning."
Elena traced a finger down his chest, eyes gleaming with promise. "Exactly. And I always collect on what I start."
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