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Keeping an eye on Dean, she pulled open the second drawer from the top and fished out her surprise. A couple of months earlier, Dean had given her what he thought of as a prank gift - an exact silicone replica of his own cock. They had laughed about it and it had been sitting in her drawer since then. Until now. She fitted it to the harness, making sure it was secure before turning back to face the bed. Dean’s eyes flicked down, widening when he realized what was strapped between her legs. 

“Don’t worry, pet,” she smiled reassuringly, “I’ll be gentle.”

She climbed back on the bed, nudging his legs until she was kneeling comfortably between them. She guided him to hold onto his knees, pulling them down toward his chest. The position raised his ass, giving her full access, just the way she liked. With gentle fingers she pried the plug from him, letting it fall on the floor by the bed. She squeezed out a generous amount of lube, coating her fake cock with it until it glistened. Dean’s eyes were locked on what her hands were doing, apprehension and desire dancing behind the mossy green. 

He gasped in a breath at the feeling when she placed the tip of her cock at his entrance, leaning into it slightly. The heavy silicone pressed against him insistently while she sought his gaze. When she captured it, she cocked her head curiously.

“Last chance to back out, Dean,” she prompted him.

Dean shook his head, having to clear his throat before he could speak.

“Not gonna back out. I want this,” he managed, his voice a little strained due to the position he was in.

Nodding, she gripped the base of her cock to steady it, placing the other hand on his leg. With slow, steady pressure, she watched the replica of Dean’s dick disappear into him. Dean grunted when she breached his inner muscle, struggling to relax and having a difficult time remembering her instructions.

“Relax, pet, let me take care of you,” she coaxed him gently, feeling him respond to her voice.

When about a third of the dildo was inside him, she paused and pulled out a little before pushing back inside. Slowly, carefully, she fed the fake cock into his ass until her skin was flush against Dean’s. She rolled her hips gently, rocking into him, giving him time to adjust to the feeling. While he did, she watched him.

His eyes were closed, his head pushed back into the pillow. His hands gripped his legs so tightly, the muscles in his arms were already trembling with the strain. His face was flushed, the color spreading onto his chest, making his freckles stand out. His full lips were parted on slow, even breaths; moist from his tongue flicking out and wetting them between breaths. He was a vision.

Eventually, his eyes opened and sought hers. He nodded, then held his breath in anticipation of her moving.

“Breathe, Dean,” she coaxed him.

She waited until he had sucked in a breath, then pulled out just a little bit. He exhaled sharply at the feeling of the cock inside him dragging against his prostate. When he inhaled, she pushed back inside. They found a rhythm that worked, her hips rocking against his ass, the replica of his own cock thrusting slowly into and out of him, each thrust massaging his prostate. His face displayed his feelings clearly and she watched as the pressure built and built and built inside him. 

He began to relax into her thrusts, even moving to meet them. That was when she sped up, just a little. She would pull out perhaps half-way, then snap her hips forward to push back inside. Each time, Dean let out a little gasp when she hit his prostate. She kept up the steady rhythm, her hand wrapping around his cock that lay heavy on his belly. Stroking in time with her thrusts, she felt him grow hard in her hand, which was still slippery from the lube. Her fingers massaged his cock while the dildo massaged his prostate. 

Dean’s head fell back, eyes closing against the onslaught of stimulation. It was almost too much. His panting breaths sounded suspiciously like whimpers to her ears. She smiled. The point was to make him feel good, and apparently she was doing her job. 

Her hand sped up, two strokes for each thrust, palm swiping over the head on every third stroke. She added a swipe of her thumb to the sweet spot just below the head, making him whine in desperation.

“Feel good, Dean? You wanna come? Wanna shoot your load all over yourself?” She prompted him, her own breaths a bit labored by now.

Dean’s response was a groan that seemed to punch its way out of his chest, the sound filled with all of his need to reach his release. She sped up again, thrusting her hips against him, stroking faster.

“Come then, Dean. Come for me, like a good boy. You wanna be a good boy for me, don’t you? Come on, gimme everything you got.” 

Her words seemed to spur him on, pushing him closer and closer to the edge. Keeping up the pace she had set, she reached down and pinched his nipples, both at once, giving them a little twist.

Dean cried out hoarsely, white ropes of come falling on his chest and belly, while she thrust into him. His whole body trembled beneath her, coated in a sheen of perspiration. His skin was flushed, from his hairline to his solar plexus, his lips dry from panting. He had never been more beautiful.

When he finally calmed down, she carefully pulled out of him and coaxed him to let go of his legs. He was still trembling and breathing hard, his eyes half-closed with exhaustion. With a washcloth, she cleaned him up, then removed the dildo from the harness before snuggling up next to him. 

“Are you ok?” She failed to keep the worry out of her voice.

“I’m...fucking awesome,” Dean exclaimed as he let out a deep breath with a dopey grin on his face.

She laughed softly at his choice of words.

“I’m glad,” was all she said, one hand slowly stroking his chest. “Get some rest, then we can talk.”

“You stayin’?” Dean tried to play the question off nonchalantly, but his anxiety that she might not stay came through.

“I’m not going anywhere,” she assured him. Then she could not resist adding, “It’s my room after all,” teasing him.