Amy does a good job

Amy overcomes her natural disgust and takes your cock into her mouth as deeply as she can, her tongue circling the glans and flicking along the shaft. She uses her gag reflex to generate more saliva, with which she coats your member, continuing to slobber ardently until you tap her on the shoulder and say "Okay."

She immediately turns around and lies down, reaching back to spread her cheeks lewdly and reveal that her resilient anus has already closed again after your earlier reaming. You get on top of her and ram your dick back inside, grabbing the pretty waitress's hair to use as leverage while you pound her snug arsehole energetically. Amy starts to whimper and you turn her head to the side so you can see the tears of pain and degradation flowing from her scrunched-up eyes.

Despite her inexperience and soreness, the eighteen year old schoolgirl falls into a rhythm, bearing down and pushing back towards you as you enter her, then squeezing her rectal muscles to give you extra stimulation as you withdraw. After all too few moments, you feel yourself approaching the climax, so you pull out completely and this time the slim brunette doesn't need any prompting to turn and slather you in drool.

You continue to alternate between arse and mouth for some time, experimenting to find the angle of entry that causes the young woman the most discomfort and also that which gives you the greatest pleasure. Soon, however, you begin to tire as your advanced years catch up with you. In truth, you're a little surprised you've lasted as long as you have; maybe there's something to be said for taking your pleasure with much younger women. You start to thrust even more deeply and urgently, finally plunging down to empty your balls in the tanned teen's burning bum hole. You slump on top of her and slide back and forth a few times to make sure you're completely spent, before rolling your bulk off to one side, allowing her to breathe once more.

To your surprise, she immediately applies her mouth to your manhood a final time, cleaning any remaining traces of her spittle or your semen. She's very careful not to overstimulate you, in case you're too sensitive following your orgasm and you find yourself drifting off to sleep under her gentle ministrations.

"Excuse me, sir," she whispers softly after completing her self imposed task, "may I use your bathroom to clean up. I don't want to leak onto your bed."

You rouse yourself to reply. "Squeeze as much as you can out of your bottom into the palm of your hand and swallow it. You shouldn't leak much after that."

She looks at you as if you're crazy, but follows your instructions without demur. Not much actually comes out of her stretched arsehole and she licks it from her palm in one motion. For a moment, you think she's going to throw up, but she forces it down and then plasters a smile on her face while she thanks you for helping teach her about bum sex.

"I'm so grateful that my first time was with you, sir. If I'd had to tip a man like that without practice, well, things would definitely have gone badly for me."

"It was my pleasure, Amy," you reply, "—literally! But you came over here to have a chat about university life, not just have sex with me."

You're tired, but take your responsibilities seriously and spend half an hour discussing how she might prepare for a place at college and what she ought to expect if she secures one. You get the impression that she's quite shocked by how harsh and demanding the disciplinary system is, yet this only makes her even more determined to succeed.

Glancing at the bedside clock, you mention that it's probably a bit late for Amy to be cycling home on her own, but she says she can always get the night bus, unless you'd like her to stay the night.