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Joan leaves Neal Friday night, and Neal wakes up Joan.
"Okay, that's enough. Turn around again and reach back and spread your cheeks for me. Press your legs tightly against the sofa and lean forward." Once again, he did as he was told.
Jeremy felt something slightly penetrate his ass but it didn't feel anything like what he thought a cock, either real or artificial would. Seconds later, there was a cool, rather pleasant sensation flooding him and the intruder was withdrawn. "That's Aquaglide," the professor informed him. It's for lubrication; otherwise what I'm about to do would be quite painful. You've got a really nice ass here, Jeremy. I'm going to really enjoy this and I think you will too."
The next thing he felt was something long and slender slipping inside, going in so easily it surprised him. Once it was there, it started moving around and spreading the cool sensation until the entire inside of Jeremy's ass was covered, even the puckered outside area. When the unknown object moved slowly in and out of him, he realized it was the professor's finger and she had been spreading the lubricant where it would be needed. So far, it hadn't been bad at all, and her finger, after she had started fucking it in and out of him, had actually given him a pleasantly erotic feeling. His cock stiffened slightly although he didn't feel very horny.
"Did that feel good, Jeremy," she asked. After he nodded his head she continued. "The next thing will be my cock and it might be a little painful at first, but I'll take it easy and try to make it hurt as little as I can. Keep your cheeks spread."
A hard, blunt object pressed intimately against him but made no immediate attempt to make penetration. Two other objects, the professor's fingers he realized, spread the sides of his hole apart and the blunt object slipped through the opening they had created. A jolt of pain shot through him as the dildo entered his formerly virgin ass.
"Uh," he grunted as he flinched, but he was pressed tightly against the front of the sofa and it was not enough to dislodge the intruder. The pain, he suddenly realized, had been neither strong nor sharp and it had lasted only seconds. There were still lingering memories of it but it had entirely disappeared and his ass felt more pleasant than painful from the head of the dildo that was lodged inside.
Hands were placed on his hips and he felt them pressing against him as the plastic cock slid deeper inside his ass. Although he was braced for another transient burst of pain like the one he had felt at first, there was none, only a strange warm pleasantness, combined with a cool feeling from the lubricant being pushed deeper into him by the dildo.
Jeremy felt the toy being slowly withdrawn. It paused for a fraction of a second and was driven into his ass even more deeply than it had been. It actually felt good as it surged into him and his hands tried to spread his ass cheeks to facilitate the thrust of the dildo. Once more it was withdrawn and once more it was plunged back in deeper yet. At that depth, the head of the dildo was massaging his prostate gland, and the wonderful sensation was completely new to Jeremy. He didn't know what to think about it but he knew it felt really good and he hoped the professor wouldn't stop too soon.
She didn't intend to stop until she had climaxed and she knew that wouldn't be soon. There were two dildos being used that day in her office. One was attached to her strapon and was working its way deeper into Jeremy and the second was the one that was held in the professor's pussy by the strap that went under her crotch. That one was made of plastic also and was covered with pyramids and stars and other molded figures that were designed to massage her many sweet spots. The main figure was the spur that would be caressing her clit once she was ready to cum and started fucking him faster. The professor was in no hurry, and hoped Jeremy wasn't either because she was going to enjoy a good, long fuck, whether he liked it or not.
He liked it.