The Professor's Dildo

Jeremy walked down the hall to Professor Dugan's office, acting much more confident than he was feeling. He had just flunked his midterm exam and knew he had to improve his grade somehow. Besides the scarlet "F" on the paper that had been returned to him that day, the professor had written "See me about this" and Jeremy hoped he could talk her into raising the grade to passing. Even a D minus would be good enough. He would still be on academic probation and not have to drop out of college and he was having way too much fun to be willing to do that.

"Come in," was the terse answer to his knock on her door. "Sit down," was the next command as the professor pointed to a hard, wooden chair. For a few minutes, Jeremy sat there squirming while she read the papers in front of her, occasionally muttering something and writing in the margins. Finally, she set them aside and turned her attention to the nervous young man before her.

"You really blew it on the midterm, didn't you?"

"I'm really sorry, Professor, but I couldn't concentrate on studying or even sleep because I was so worried about my mother in the hospital and..."

"Cut the crap, Jeremy. You didn't study because you were out with some girl all night before the exam. Isn't that right?"

She was so absolutely correct that he couldn't say any more. All he could do was wish he had worked harder.

"So, what do you propose to do about it? I know you're on probation and if I turn in this score, you'll flunk out of college. You'll go home in disgrace and there won't be any hot college girls for you to fuck." As she spoke, the professor threw back her shoulders, causing her big breasts to thrust forward.

Jeremy stared at the professor, surprised at her choice of words and doubly surprised at the way she looked. Instead or her hair being in the usual severe bun, it was down to her shoulders in soft waves. Instead of the usual boxy blazer, she was wearing a soft knit sweater and, as her breasts moved under it, he realized she was not wearing a bra. "She's coming on to me," he told himself. "This might be my chance."

"You're right, Professor. I was out with my girlfriend the night before the exam and I was giving her such a great time, she wouldn't let me go."

"Is that right? Pretty good at fucking, are you?" Professor Dugan pulled down on her sweater, making her nipples stand out and moved her upper body, causing her unfettered breasts to sway enticingly.

"I've never had any complaints. Do you want to find out?"

"What are you asking me, Jeremy? Are you suggesting that if I let you fuck me, I should then give you a passing grade? Because that's the least that you'll need to continue being a student here?"

"Well, yeah."

"Why should I want to do that? I get it on with some of the hottest studs in town. Why should I want to spread my legs for a kid like you?"

"Then what's all this about, with the sweater and no bra and...and, all that? And all this talk about fucking?"

"I don't want you to fuck me. I want to fuck you."

"You? Want to fuck me?"

"That's right. You say you're pretty good at fucking? Okay, let's see how good you are at being fucked."

"But how? You're a woman and I'm a man."

"With this." She opened a bottom desk drawer and pulled out a device like nothing Jeremy had ever seen before. It looked like it was made of leather and it had some straps and a big, white thing that looked almost like a cock.

Suddenly, Jeremy realized it was a cock, but made of plastic or something, and bigger than his. A lot bigger. He had seen one of those things before too, or something just like it. It had been in a lesbian porno film and one of the actresses was using it on another woman. A cold shiver of dread went through him as he realized what the professor had in mind.

"I'm a man! I can't do that."

"Oh, yes, you can. Whether you do it or not is up to you. You have two options, young man. One is to walk out of my office and keep going until you leave the university, because you will be flunked out as soon as I turn in your test score. The other is to walk over to that sofa, take off all your clothes and kneel in front of it and be fucked in the ass until I cum. The choice is yours."

"But I'm not queer. And I'm not a woman."

"I assume you're a man and there's nothing gay about sex between a man and a woman. You might like it, you know. A lot of women do, and a lot of men. Not just gay men, either. The choice is yours, though, and you have to make it right now."

He realized she was telling the truth but Jeremy still didn't like the idea. He knew it was one of the things that gay men liked to do and women had been fucked in the ass in some of the porno films he had seen. They acted like it was fun but it might have been just acting. Whether they liked it or not, they hadn't been hurt by it and he was sure the professor wouldn't inflict any actual injury on him either. He still didn't like the idea, but he couldn't help believing a short period of discomfort, even some pain, would be worth it if he got to stay in school. Suddenly, he had another thought.

"You wouldn't tell anybody about it, would you?" He would have been mortified if word were to ever get out about his being fucked in the ass by a woman.

"Of course not. It would be strictly our secret, and just the one time, unless you want to come back for more."

Jeremy was sure he wouldn't want to come back for more but he was also sure he could handle it one time. "Okay," he said. "I'll do it." He stood up and walked over to the sofa.

First he sat down and took off his shoes and socks. His shoes had to be taken off before he could remove his pants but he wasn't sure why he took off his socks except he always did before having sex. Barefoot, Jeremy stood up, removed his shirt and started unfastening his pants, only to hesitate when he saw the professor looking at him.

"If you're bashful about showing me your cock, you can turn around to take off your pants and underwear. I'm just interested in your ass anyhow."

Jeremy took her suggestion and, when he was completely naked, he knelt on the floor, leaning on the vinyl sofa cushions. He wondered how many other young men had been here before him, doing the same thing he was about to do. Nobody had ever mentioned it to him and he certainly wouldn't tell anybody either. When he was in position, he spread his legs as he was told to do.

He couldn't see what was happening but he heard the desk drawer close and footsteps on the carpet. The slide bolt on the door was thrown and, seconds later, Jeremy felt the professor's bare feet against his legs as she stood between them.

A soft rustling sound came next and he saw her sweater tossed on the end of the sofa opposite from where his clothing was piled. He wondered what her breasts looked like and if he should turn around and see. Before he could decide, something else made of cloth landed on the backs of his calves. A few seconds later, one of her feet moved away briefly and returned, followed by the other one doing the same. He no longer felt the cloth thing against his legs, but he saw a skirt and panties added to her pile of clothing.

"You can look at me if you want to," she told him.

Jeremy twisted his head and shoulders around and saw a grinning face above a pair of large breasts with big, dark brown nipples. Looking lower, he saw a thatch of dark pubic hair. The professor hadn't yet put on the thing she was going to use on him.

"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. The dildo was actually a long cone, thicker near the base. With every stroke, the greater girth of the toy was stretching his ass wider, and sending strange and different pleasures coursing through his body. As the tip wedged in farther, it went where nothing had ever gone before, feeling like nothing Jeremy had ever felt before, but it felt indescribably good to him.

The best part, though, was the way the head and more and more of the shaft were indirectly massaging his prostate. The only thing he had ever felt that was as good as what the plastic cock was doing had been the best sex he had ever had with a girl. The fucking he was just starting to get from Professor Dugan was already more pleasurable than most of the fucking he had gotten from his girl friends. The dildo sliding in and out of his ass felt so incredibly that he started fucking back to meet it, fully aware that his actions would tell her that he actually liked it. Everything about what was happening was so great that he didn't care if his partner knew it or not.

Over and over and deeper and deeper the professor's dildo plowed into Jeremy's ass until it was completely imbedded with every stroke. She could feel her thighs pressing against his hands which were still holding his ass cheeks open. For some time, Professor Dugan had known that the young man was enjoying the fucking she was giving him, from the way he moved to meet her thrusts and from his involuntary moans of pleasure. Until then, her body had been upright and her hands had been holding his hips for leverage but that was no longer needed. She preferred a more intimate position so she put her hands on his shoulders and leaned forward so her mouth was inches from his ear.

"You really like this, don't you?" she whispered.

"Uh huh," Jeremy whispered back. He liked it even more when she leaned forward on him because he could feel her breasts pressed against his back and her hard nipples digging into him as she moved.

"Good. It's more fun for me if you like it too." She continued slowly stroking her dildo in and out of his ass while the toy inside her pussy moved around, caressing her most sensitive places and ratcheting her level of pleasure upward toward what she knew would be an ecstatic orgasm.

As the dildo continued to drive in and out of his ass, sending waves of pleasure sweeping through his body from every place it touched, Jeremy was also feeling a certain amount of distress. His cock had become extremely hard, so rigid that it actually hurt, much the way he sometimes lied to women about it hurting as a seduction ploy. He hadn't masturbated for a long time, not since coming to college where the women were willing and plentiful, but he badly needed to do it then. Unfortunately, he was pressed too tightly against the front of the sofa to have any room to pump his cock.

Professor Dugan saw what he was trying to do. It was the same thing as most of the other young men had wanted to do while she was fucking them with her strapon. "Do you want to jack off?" she asked.

"Yeah, but there's no room between me and the sofa."

"Okay, let's move back a little. You can put some of this on your hand if you want to." She gave him the bottle of Aquaglide

With the dildo buried in Jeremy's ass, they moved together, slowly backward until he had enough room to stroke his cock the way it needed to be stroked. She resumed plunging her toy into him and, after applying the lubricant, he began masturbating, subconsciously at the same pace as he was being fucked. It was too slow for him to cum for a while but it gave relief to his cock and added to the mountain of pleasure that he could feel building up inside him.

For a long time the professor continued fucking Jeremy's ass, feeling her own pleasure mounting until she knew her orgasm couldn't be delayed any longer. After noting that he was still stroking his cock she whispered a suggestion to him. "I'm going to start fucking you faster. Let's try to cum at the same time."

"Yeah. I'd like that too." Jeremy always tried to achieve simultaneous climaxes with his girlfriends and saw nothing strange about doing the same thing when he was the one being fucked.

Professor Dugan had been kneeling behind him and leaning forward on his back but she changed her position to make full use of the specially designed spur on the dildo in her pussy. She moved into a crouching position, her feet outside his knees and even with them. She appeared to be sitting on his hips while she drove the dildo faster and harder into the man below her.

Jeremy felt the change. He liked the faster pace and he matched it with the hand that was stroking his cock but otherwise he didn't like it. He wasn't being pleasured as much from the new angle because the dildo wasn't going as deeply into him. He corrected this by arching his back, presenting his ass differently to his partner so she could resume ramming her cock into him all the way to the face of the strapon. Happily, he continued along the path to ecstasy. She hardly noticed his adjustment. It didn't change what the other dildo was doing to her pussy and she was too close to her orgasm to care anyhow.

The pleasure radiating out from Jeremy's cock had been adding to his overall level but he could feel a sudden and familiar surge welling up inside him. "I'm cumming! He announced, and started moving his hand as fast as he could.

Her words practically echoed his. "I'm cumming," she cried out joyfully, as the spur on her dildo accomplished its mission. Everything felt perfect to her as she started driving her dildo even faster and harder into Jeremy's ass.

"Uh! Uh! Uh!" Jeremy grunted, taking as much pleasure as he could, yanking on his cock and thrusting back to meet the dildo that was giving his ass such a great fucking. "AH!" he cried as he climaxed, ejaculating heavily on the floor and onto the front of the sofa. One arm was still on the cushion and he leaned heavily forward as he relaxed completely.

"YES!" she cried as she climaxed ecstatically. All the professor's muscles also collapsed and she leaned forward affectionately on top of the man she had just finished fucking. The dildo on her strapon remained in place, sending out more thrills of pleasure rippling through Jeremy's body, but he was too satisfied to even care.

For a long time the two of them remained in the same position until she slowly got to her feet and cautiously pulled the dildo from his ass. He turned to her, smiled and exclaimed "That was incredible, Professor! I've never felt anything as good as that. I hope we can do it some more."

"Yes, but not today. We can get together again, at least a few times, and I surely want to. Next time you come to see me for this, why don't you call me Patsy? And let's make a special point to get together for a longer session just before finals. I'll see if you can earn a good enough grade in my class to get you off probation."

*

Thank you for reading this story. I hope you had as much fun as Jeremy and the professor did. I like writing stories on this site but I like it a lot more when I know that people are reading and enjoying them. That's why I always appreciate it when readers take the time to express their opinions by voting. Like most other writers on Literotica, I practically live for feedback, either public comments or email to me. Such comments help me to write more and better stories, and I respond to them whenever I can.