Anal training

"Have you ever taken it up the arse, Amy?"

"N-no, sir." She reaches behind her back and presses her bum cheeks together nervously, as if she can somehow prevent an unwelcome entry that way. "My parents say good girls don't do that, at least not unless they marry a man who wants to."

"Well, Amy, as you've noticed, the tipping rules mean that from now on, girls are going to have to do a lot of things they wouldn't have before. This is one of them, but if your parents have forbidden it, we'll do something else."

"Oh, no, sir, I didn't mean that! When I told them what I was doing tonight, they said I should do anything you wanted, so it's totally okay if it's what you'd like."

"Absolutely. I think it would be wise for you to keep your bum hole clean and lubricated all the time from now on, just in case a man wants to be tipped that way and doesn't give you any time to prepare, but you can take a few moments now if it would help."

"Yes, sir, thank-you. The school nurse gave all the over-eighteen girls enemas this afternoon when the tipping rules came into ****, but that was hours ago and she didn't say anything about lubrication. I actually thought she was overreacting, because it seemed so unlikely anyone would want that sort of tip when they could have full sex, but maybe anal is more common than I imagined."

"For tipping, it probably will be, because as you say, good girls don't do it otherwise. If you go upstairs, the bathroom's first on the left."

"Erm, do you have any lube, sir?"

You think you saw some in the bedroom spanking cabinet, but the young waitress should learn to stand on her own two feet, so you reply that she can make do with soap suds and spit for tonight and maybe invest in the proper stuff tomorrow. She nods and trots off up the stairs, naked and carrying nothing except her ruler, with you following more sedately behind.

You originally intended to wait for her in the bedroom, but it occurs to you that watching her ablutions might be quite fun for you and embarrassing for her, so you continue to follow right into the bathroom. Amy goes straight to the vanity unit under the hand basin and after moving things round inside looking for something, takes out an enema kit which you didn't know you owned and places what looks to you like a quite large quantity of Castile soap and glycerol mix into the bag. She then sets it to fill in the basin, gets in the shower and, bending double, turns on the water and immediately directs the icy flow between her cheeks. She assiduously scrubs her brown puckered hole inside and out, using her fingers and the liquid soap you keep in the shower and finishes about the same time the water has warmed up to a comfortable temperature. She turns it off and reaches out of the shower to get the enema bag, which she hangs from the ceiling shower head, then washes the nozzle carefully with more soap, before inserting it slowly (and somewhat painfully) into the appropriate orifice.

"Oooo-ooh! It's cold," she says, rising up on tiptoes as she releases the flow. "Ugh, I'm cramping already." You can see the shudder running through her abdomen, which you think looks slightly distended, although it might be your imagination. The whole procedure is clearly very uncomfortable, bordering on painful, but it's soon over and she withdraws the nozzle, squeezing her cheeks together to keep the cleansing liquid within. The slim teenager takes a few moments to clean the nozzle again, legs shaking from the strain of holding the enema in place, before decamping to the lavatory and loudly and humiliatingly evacuating her bowels. She flushes and returns to the shower, flashing you a smile as she goes.

"Almost finished, sir. I'm sorry to keep you waiting."

That last phase involves a thorough rinse and a second lathering for lubrication, during which you notice that Amy is able to insert a finger entirely, without difficulty but not without discomfort.

You take a towel from the heated rail and use it to dry your guest when she steps out of the shower onto the bath mat. Obviously, she would be more than capable of doing this herself, but you quite enjoy running the towel over her svelte form.

You lead the tanned beauty to your bedroom and tell her to lie face down on the bed, legs wide, then shrug off your robe and climb on top of her, aiming your rampant prick at her tiny hole. You spit in your palm and smear the saliva over your shaft, then press the cock head against her puckered sphincter with your thumb.

"Bear down like you're on the toilet, Amy."

"Yes, sir. Ahhhh."

Amy groans as you stretch her wider than she's ever been stretched before, whether defecating or getting a medical check-up. She's so tight, it's almost a relief when your glans pops past the entrance and you're able to drive steadily into her virgin arsehole.

"Uuurgh. Ohhh. Nnnngh. Please, is there much left?" Her voice quavers piteously, her rectum having been left sore and irritated by the enema.

Looking down, you answer her concerns and are amused to notice that her toes are curled with the effort of not resisting your entry. "I'm about a third of the way in."

"Oh, no, it feels so big!"

"Don't worry," you reply, "it'll fit."

You wonder whether you ought to have her get up on her knees to make the angle of penetration easier, but decide to continue in the position which will give you the most stimulation, at the cost of greater hardship for the girl beneath you.

Finally, your hips reach her buttocks and you reverse direction, causing more moans. The second thrust is easier and faster—and much more painful for Amy. Hands on her shoulders for leverage, you begin to saw in and out, pounding her callously as she starts to sob, then howl.

"Do you need more lubrication?"

"Yes, please, sir," she gasps and you quickly pull out and use her hair to drag her face around to your crotch. The look of revulsion on her face when she realizes you mean to have her wet you with her mouth is delightful, but at the same time rather disappointing. Overall, you'd rather have Amy's genuine reactions rather than a pretence that she's not thoroughly hating what you're making her do, but other men may feel differently, so you decide to talk to her about it later. For now, though, you just want to alternate fucking her face and arsehole until you spend yourself within her, so you pull her closer to your prick.