Assume the position

Tori aligned the tip of her strap with Oliver’s ass but didn’t insert it yet. Instead, she took two lube covered fingers and started massaging his hole, swirling the gel around. Satisfied with the outside, Tori inserted a single finger, slicking him from the inside. Finding that Oliver’s ass easily accepted a single digit, she added another, working them in and out. After yesterday’s shower, the sensations weren’t completely foreign, but they were still new, and he stilled the urge to move his hips in time with Tori’s fingers.

Plenty of time for that… for now let’s just get used to her fingers. Christ, that feels so good.

Tori smirked at her submissive roommate. Satisfied with her preparations she wedged the tip of her strap into Oliver’s waiting ass, letting it rest there. “Like I was saying Ollie, assfucking is a different game entirely” Tori began to push forward with agonizing slowness, “go to hard, too fast- you’re gonna have a bad time.” A soft “ahhhh” from Olier told her that she could go on.

“You go in guns blazing and then next thing you know, mood’s gone.” She was more halfway through the six inches of silicon, intent on getting the while thing in. “You have to start gently Olle, let them get used to you.” Three quarters of the way there, Tori savored Oliver’s lidded eyes and shallow breathes. Who would have guessed that Ollie was such a good bottom? Always figured he’d be far more dominant in bed, Tori thought to herself.

Finally, Tori hilted the full length inside Oliver. Resting there and letting her quarry adjust, Tori idly started playing with Oliver’s shaft. Oliver’s cock, half erect already from the penetration, sprang to attention. “But the real skill of good anal little slut, isn’t going in-“she started withdrawing the cock “it’s coming out.”

Tugging on Oliver’s cock, Tori spent the next few minutes moving tantalizingly slowly. Every once in a while, she’d add a couple more drops of lubricating gel to the dildo, until it was gliding in and out of Oliver smoothly. She forbade him to cum, careful never to stimulate his aching cock too much. But once Oliver’s ass was easily taking the practice cock, she withdrew entirely. Confusion and disappointment washed over Oliver’s face, deprived of the wonderful feeling of being fucked.

He didn’t have to wait long, as Tori was simply swapping the dildo out of its holster for a much larger one. The rival of the suction cupped toy from their shower, it was twice the girth of the one Tori had just been training him with. The process started anew, but Oliver was never in any pain- Tori took every care to ensure she never overloaded or injured him. Oliver had no idea how long she’d been training his asshole; it could have been hours or still just minutes. He was in heaven from Tori’s edging, his hole clenching around the cock mounted to Tori’s beautiful body, dripping precum from light stroking of his cock.

Tori was impressed at how adaptable Ollie’s ass had turned out to be, realizing she was picking up a steady rhythm even with the much larger toy. Looking down at her roommate, she had only one word to say to him.

“Beg.”

Oliver instantly obliged, babbling out how much her loved her cock, how good she felt, how he wanted her to fuck him harder and faster, thanking her for fucking him. She’d been edging him for half an hour now, Tori was impressed he hadn’t cum ages ago. Well, time to fix that, she thought. Planting her feet, she started thrusting in earnest, the ample prep time letting her ram into Oliver with impunity.

“fuck fuck fuck unf fuck Tor fuck fuck god fuck unf ah fuck unf fuuuuck.” After obeying in silence for so long, Oliver’s slutty cries echoed out like music to Tori’s ears. Slamming in as far as she could go, she withdrew half way and slammed back in again. Oliver’s hips bucked, his back arched, his sweat drenched head rolling on the pillow as he was truly fucked for the first time. After so many repeated denials, he came without warning, his load bursting from him, one strand catching Tori in the face. Oliver moaned weakly, he felt like he’d been hit by a truck.

A laughing Tori dragged a finger across her cheek, and suckled the cum off it like it was a lollipop. “Fucking bravo Ollie, exceeded my wildest dreams with that one.” She carefully withdrew the toy from Oliver’s abused ass, and loosened the leather harness, letting it drop. With the clean hand she’d just sampled the cum from (she’d only used one on his ass) Tori scooped some of the still warm cum off Oliver’s torso, and slid her fingers in his mouth. Oliver eagerly sucked the ejaculate off her fingers, looking up at Tori, unsure of what was going to happen next.

Tori’s nude form mounted the bed, dropping down onto Oliver’s face. “You got yours Ollie, time for me to get mine.” Oliver could barely breath, his need for oxygen overridden by the need to pleasure sodden cunt crushed into his face. Tori’s hands caressed her sides, cupping her own breasts and teasing her pierced nipples. She rode him mercilessly, increasing her speed until she cried out in her first orgasm but rather than calming her climax served only to press her onward. Oliver sucked air through his nose, the sweet taste of Tori’s juices flooding his mouth. He raised his hands and grabbed Tori’s ass and as she prepared to dismount (for fear she was really suffocating him) instead moaned as Oliver pushed her against him even harder. A second orgasm wracked Tori’s body, a third, a fourth, each rolling and flowing into the next until finally she wrenched away and threw her body to the side.