And claimed

Tori’s jaw hung open, trying to piece together the evidence before her. Oliver stood up the gears of his mind spinning wildly. He’d always thought his roomie was gorgeous, but had never really thought about fucking her. Facing each other, Oliver’s real cock pressed against Tori’s fake one, Oliver knew how he wanted to claim his victory. “Tor, you wanna fuck me in the ass?”

Tori’s expression morphed into a wicked grin, she leaned up and planted a kiss on Oliver’s lips, one hand grabbing the back of his head and the other groping his ass. “Oh Ollie I would love to. Give me a sec to swap this thing out, I have a much better one- Lie back on the bed.” Oliver dutifully obeyed, tilting his head up to watch Tori’s ass as she swapped out the strap on. When she turned around and padded back over to him she’d replaced the comically large pink dildo for a much more sensible jet black cock slightly smaller than Oliver’s own manhood. Oliver’s own cock had shrunk to half mast, but as Tori cupped his balls he felt himself hardening again. Moving quickly and efficiently, Tori applied lube to the dildo and Oliver’s exposed asshole. “Lift your legs up like a good boy Ollie, gonna do you right.”

Swinging his legs up, Tori placed them over her shoulders, teasing the narrow tip of the stap-on to Oliver’s waiting ass. Unlike the night before, Oliver didn’t have the benefit of **** to relax him so he did his best to unclench. Tori started off gently, working the tip into Oliver’s ass before transitioning into slow, shallow thrusts. After Simon’s claiming of his anal virginity the night before, Tori’s toy was hardly a challenge.

Oliver grinned at Tori “That all you got?”, but before she could fire off a snarky reply Oliver wrapped his legs around her and drove her all the way in. Oliver groaned in pleasure as the fake cock rested snugly inside him “ohhh goddamn, that feels good.” Tori wrapped a hand around his cock, her thumb smearing the dripping precum around “Ollie Ollie oxen free, want me to speed things up do you?”

It was Tori’s turn to act without waiting for a response, drawing the strap on nearly all the way out before plunging back in. With practiced ease Tori railed into him, her hips rolling in a steady rhythm- stroking his cock on the half beat. Oliver knew he couldn’t last long and tried to grunt a warning, but failed as cum erupted from him, one rope draping itself over Tori’s tits.

A wolfish grin on her face, Tori withdrew the dildo and unfastened the harness as Oliver lay on the bed panting “you made a mess Ollie, next time warn a girl, I wanted to finish you in my mouth.” Oliver chuckled weakly “Sorry Tor, anal’s still really new to me, I didn’t expect to cum that fast.” Sitting up, he pulled her close and licked the errant cum from her breasts before looking up “I know that was my prize for winning the bet, but friends don’t let friends not cum.”

Tori shrieked in surprise as Oliver threw her on the bed with ease. The strap-on and harness lying on the floor meant that Oliver had an unobstructed path to Tori’s cunt. He didn’t waste any time, latching on to her clit as two fingers teased her outer folds. Tori grabbed his hair and writhed under him as he began pumping the fingers in and out. Within moments Tori clamped her thighs around Oliver’s head as an orgasm ripped through her body.

Sliding up the bed to lie next to Tori, Oliver kissed her the side of her head, trailing down her neck and onto her shoulder. “We definitely…” Tori whispered, “have to do this again.”