Three for three

You squeak in terrified surprise, eyes widening as you feel a finger venturing into your asshole. You hadn't thought about anal sex much, mostly because you heard it hurt like hell from all of your girl friends who had tried it. Now, with your legs up in the air and the teenager leaning over you, there doesn't seem to be much of an option.

"Damn," he mutters, barely managing to squeeze in a second digit. "Maybe I should just break up with May. Now I get just how much of a whore she really is..." His fingers begin a surprisingly slow and gentle scissoring motion, gradually stretching your rear entry. He shifts his pensive gaze to meet your anxious one, breaking out a smile after a few seconds. "What do you say? Wanna be my girlfriend? And, before you ask, I'm not in high school. I'm nineteen."

You can only gape at him, unable to find your voice. Not that you have an answer to give him. This kid wants to just dump his girlfriend because he likes fucking you better? Talk about superficial.

Much to your surprised chagrin, you let out a disappointed whimper as he retracts his fingers. A chuckle rolls through his chest as he shifts to align himself with your last remaining virgin hole.

"You don't have to answer right now," he says, his smile clearly genuine. "I'm breaking up with her either way. Been thinking about it for a while. I just thought you and me could have fun together."

His hand clamps over your mouth simultaneously with his cock pushing into your ass, muffling the scream of shock and pain. He holds still, waiting for your breath to calm some and your muscles to relax a little before moving again. This stop-and-go process continues until, finally, you feel his hips resting solidly against your ass. Your eye twitches, threatening to roll with solely the sheer fullness you are experiencing. It feels so wrong having something go in your body's natural exit door, yet, the longer he waits to let you adjust, the more right it becomes. The pain starts to meld with an odd sort of pleasure.

Then, he moves.

His hand remains in place, muffling your moans and cries of pain as he pulls out and pushes back in. Despite the hurt, you find yourself enjoying it. Your nerves tickle similarly to when he took your pussy, sending shivers through you. Eventually, your arms find their way around his neck, pulling him tightly against you. He smiles, pecking your cheek softly as his speed increases.

After a couple of minutes, your eyes finally roll, your toes curling and abdominal muscles seizing up. Orgasm crashes over you as he hilts himself fully, trapping his dick deep within your bowels. Unlike before, he can't hold back this time. Another, smaller orgasm ripples within the waning first as you feel warmth blooming within your depths, a part of your brain recognizing that he is cumming inside of you.

As you both come down, he moves his hand, dropping his weight on top of you. For over a minute, both of you lay there gasping for breath. Your efforts are made easier as he finally pushes himself up, slipping his cock out of you once more.

"Fuck," he breathes, dropping back into the seat heavily. "That was seriously something else." A slight smile twitches at your lips. For some reason, the complimentary statement gives you a little sense of pride. "So," he begins again, voice getting stronger as his breathing regulates, "what do you say? Want to do this again sometime? This isn't the only perk of dating, either."

You hesitate, surprised to be seriously considering the question.