Blind Date

He arched his back and cried out in pain, gritting his teeth as she bit her lip to withhold a deep moan.
Instead she lay down, pressing her breasts into his chest as her hands moved up to caress his hair, leaving her cock inside him, allowing his tight ring to adjust to her impressive girth.
"Shh, it's okay... It's okay, the first time always hurts, like any virgin... The pain will go away soon I promise, I promise..." she whispered softly into his ear, reassuring and calming him from the sudden influx.
She held him and spoke to him like that for a couple long minutes before pulling back a little and looking at him, hopeful.
He bit his lip, but nodded, closing his eyes and gripping the sheets in preparation.
She smiled and moved back up onto her knees, looking down and seeing for the first time where they were joined, the very tip of her thick cock vanished inside his tightness, it looked so good, so tempting, more than ever she knew he was the one, that he would spend a lot of time in his current place, not as a toy, or just a friend with benefits, but as her life partner.
Slowly she began to build the pressure back up, moving easier this time, her cock dominating him inch after inch as at a minuscule pace she fed herself into him, filling him, claiming him.
He gasped, whimpered and writhed, struggling to come to terms with just how tight the fit was and just how much cock she was urging into him, but he never told her to stop, never thought he couldn't or wouldn't do it, he could and he would, for her.
Claire chewed her lip watching him, gorgeous and wonderful, taking her cock like a star, letting her push forward until, to their mutual surprise, she had buried her entire python inside of him in one single, albeit slow push.
She didn't afford him as much of an acclimation period this time, instead pulling out, only to push back in, her movements solely orchestrated by the gyrating of her hips, her eyes locked on his expression, though he had his eyes closed, she reveled in the look of determination. She knew it wouldn't feel good for him, yet, but his sheer willpower in going through this minor ordeal for her pleasure was such a turn on for her that she found herself admiring and lusting after him more and more with each passing second, even as she finally sated those needs.