Eagerly, the sweet girl got on all fours, her head down at his penis and small pink tongue already licking their combined juices from his groin. Chad again wished that this wouldn’t be his last time with her, she was eager and willing to try anything he said, and her responses were amazing… some girls would put up a bit of a fight before cleaning him off afterwards, or would suddenly want to stop even though they knew part of the deal was their virgin ass, and then he’d have to go through the whole rigamarole of convincing them. Not Clarissa, she had the body and experience of an angel, but the heart of someone who was born to please men. Positioning her so that she had one leg on either side of his head, he rubbed her soft thighs and ass cheeks before dipping his finger into her pussy, covering it with a mixture of their cum. Rubbing the messy wetness on her asshole, he pushed just the tip of his finger into the tight crinkled light brown hole.
For a moment, her body tensed and she paused in her licking, but after her ass clenched and then released around his fingertip a few times she adjusted and started licking him again, now moving her mouth down to the wetness on his balls. As she sucked on of his balls into her mouth he started sliding his finger into her ass up to the first knuckle, when she didn’t even pause in her suckling he slid it all the way in. Moving it in and out a few times, he sighed happily as she sucked the other ball into her mouth and he could feel his arousal starting to stir again. He pulled the finger out as her mouth closed around his dick, gently sucking and caressing it with her tongue; he could feel his dick starting to harden with her encouragement as he slid two fingers into her back door. The tightness was incredible, but she didn’t resist at all as he worked the two fingers in and out of that stretched hole.
With his dick standing at full mast as she slid it down her eager throat, he added a third finger to the crinkled hole, and she moaned a little, her body wincing as the fingers burned a little in their journey. Still, nothing was actually feeling overly painful, he was being very careful in how he stretched her, and she could actually feel herself starting to get a little turned on as he slid his slick fingers in and out of her ass. This was the part she had been the most worried about, she’d always heard that it hurt terribly to have anal sex, and even Claudia had said that it had hurt her some, but she wanted it too. She wanted it badly, and the slight amount of pain was even turning her on a little. Her ass felt full, maybe a little uncomfortably so, but she felt dirty and naughty with her former teacher’s fingers in her ass and his dick sliding in and out of her throat; the whole situation made her extremely turned on and horny.
Pulling her mouth from his dick, she pulled her ass off his fingers and got on all fours next to him, looking back entreatingly, “Please, do it, please fuck my ass now…I think I need it.”
Those dirty words coming out of that sweet and rather innocent -if admittedly less so after the past hour – mouth, made Chad’s eyes practically glaze over with lust. Faster than he could have imagined, he was kneeling behind her, positioning his dick at her slightly stretched hole. Slowly, her ass stretched around the head of his cock and she moaned as the pain shuddered through her body… oh he was hurting her wonderfully. As he slid another inch into her slick back door she lowered her head onto her forearms, leaving her ass high in the air for him to plunder, as she panted and tried to adjust to the exquisitely painful invasion. He began to work his dick back and forth in her ass, slowly working inch by inch into the stretched orifice, letting her adjust as his dick traveled deeper into her brown hole. Whimpering, Clarissa pushed her ass back onto him, shoving the last inch of his dick into her so that the pleasant sensation of being painfully full swept over her completely as his dick was completely buried in her hot little hole.
Chad groaned and laid his body over hers, reaching his hands around to grasp her breasts as he moved his dick in and out of the slick hole; it was the tightest back door he’d ever been able to sink into… a lot of the girls wanted to be totally stretched out as he entered them. Clarissa seemed to revel in the discomfort and slight pain. As he pinched her nipples, she struggled to push herself back up onto her hands, wanting to be able to push back against him as he plundered her no longer virginal hole. She gritted her teeth and began ramming her soft firm ass against his body every time he slammed home, a new kind of pleasure sweeping over her as her ass was filled and refilled with his hard dick.
Using his arms, Chad leveraged her up so that she was at a 45 degree angle, holding her up with one hand flat against her stomach and the other buried in her pussy, rubbing her clit and stroking the wet folds with his fingers. Clarissa cried out as the position allowed him to burrow deeper into her ass, finding new areas to explore and stretch, her head fell back as she started squeezing her own breasts, pinching and twisting the tender nipples.
As yet another orgasm crashed over her, she started crying out obscenities, completely lost in the moment, “OH GOD… FUCK MY ASS MR. DAVID…. FUCK ME…. OH FUCK ME HARD!!!! CUM IN MY ASS!!!! OH GOD I’M CUMMING MR. DAVID!!!! FILL ME UP WITH YOUR CUM!!!!!!!!!!!!!!!”