Another Lesson

"What's next?" I ask, still somewhat in a daze. "I don't know."

"Ummm, do you know anything about anal sex?" you ask coyly.

"An..anal sex?" I stammer. I wondered briefly when I would wake up, but if this was a dream, I think I'd be happy to stay asleep forever.

"Yes," you say. "Guys are always wanting me to have anal sex, but I've never done it and, frankly, I'm a little scared of it. But after today, I trust you. Could you teach me?"

My mind raced. There wasn't much I could do now, either physically or in terms of instruction. I didn't have any lube or toys here. On the other hand, the thought of having anal sex with you, a young, beautiful, sexy student, was more than I could handle. I couldn't pass that up. "Well, yes, I can teach you." You grin, but that grin turns into a frown as I say, "But not here. Not now. We will have to make some other sort of arrangement."

"Whatever you say," you reply grinning. "You're the professor." We arrange to meet at a hotel that weekend. I book a nice room and make sure I have all of my instructional materials ready. I get to the room almost an hour before we agreed to meet, I'm so horny with anticipation.

When you finally arrive, I can barely control myself. You also seem to be ready and willing, and we continue where we left off in my office. We rip each other's clothes off and I soon have you down on the bed, my head between your legs. Without the danger of being discovered, you moan loudly in pleasure as I bring you to what seems like an even stronger orgasm than before.

As you come down from your orgasm, I turn you over on to your belly and get you onto your hands and knees, your ass in the air. I get the lube I had brought with me and put some on my finger and some on your ass. You squirm at the touch of the lubricant. I gently rub my finger back and forth across your opening, letting you get used to the sensation. As I can feel you relax, I push my finger into you. You gasp and I can feel you tighten up again. I tell you to relax and soon you are able to allow me to move my finger back and forth. I can hear you start to enjoy it and my other hand pushes a finger into your pussy. I add more lube and slowly push a second finger into your tight ass. I again allow you to get used to the sensation before I start to slowly fuck your ass with my fingers. I add a second finger to your pussy and I can feel you get hotter as my two hands pleasure both of your holes. Your moans turn me on even more, my cock aching for release.

I remove my fingers and bring out the toy I had brought for the evening, a butt plug. I lube it up and tease the opening of your ass with its tip. I push it slowly in and hear you gasp with pleasure and pain as it moves past your sphincter and almost pops into place.

"How does it feel?" I ask. You take a moment to respond.

"Good, I think. Full. But it doesn't hurt. What do we do now?"

"I'm glad you asked," I grin and flip you over onto your back, spreading your legs. I thrust my aching cock into your wet pussy and we both gasp from the tightness and fullness of the experience. I can feel the plug underneath me as I thrust into you.

I'm so turned on that any thought I had to go slow flies out the window with my self control. I thrust into you hard and fast. My cock is twitching at the new experience, and your moans tell me that your pussy feels the same way. Soon I reach the point of no return and realize that I hadn't put on the condom I brought nor discussed birth control with you. But it's too late.

As our orgasms build, we both let out groans of ecstasy as my cum explodes into you in the most powerful orgasm I've ever had. The feeling of the plug under the shaft of my cock seems to stretch out the experience as each thrust pulls out more and more cum.

I finally collapse on top of you, completely spent, but knowing we're not done for the night. You seem to know it too. With your fingers in my hair, you put your lips right up to my ear and ask:

"What's next?"