16 comments/ 168846 views/ 73 favorites The Professor's Dildo By: Boxlicker101 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. The Professor's Dildo Ch. 02 CAUTION: This is a story of a woman using a dildo to perform anal sex on a man. It is entirely consensual, and both parties enjoy it, but if this sort of thing disturbs you, I would suggest you not read it. * Jeremy smiled as he strode down the hall to Professor Dugan's office, anticipating the fun they were going to have. The final exam in her class was the next day and he was on his way to earning the highest grade possible, besides having another great time. Three months ago, Jeremy never would have thought it possible, but having her fuck his ass with her strapon had already given him some of the most fun he had ever had with a woman, and he was really looking forward to that day's session. The sad part was that it would be the last one of the spring semester and, after that day, he would have to do without the incredible pleasure for over two months. He hoped to enroll in one of her classes in the fall, and enjoy another five months of having his ass getting regularly crammed by her, but it was still a long period of doing without. Jeremy knocked on the door and entered when he was told to do so. The professor smiled at him and leaned back in her chair, thrusting her breasts against the thin material of her jersey. The garment might have been the same one as she had been wearing their first time together. "Hello, Jeremy," she greeted him, and got up, bolted the door and walked over to stand in front of the sofa that stood against the wall. "Hi, Dixie." Jeremy had called her by that nickname during their sessions ever since their second time together. She had been leaning over him, her hands squeezing his shoulders and her succulent breasts mashed against his bare back. Jeremy was ecstatic, from her hard nipples scraping back and forth against his skin and, best of all, her big plastic cock driving smoothly in and out of his well-greased ass. He had whispered to her how good it felt, and addressed her as "Patsy", which is her actual name, and the one she had suggested he call her when they were getting together in her office. "Jeremy, why don't you call me Dixie, when we're in the office and I'm fucking you like we are now? That's what my special friends call me, and I like to think you and I are becoming really special friends." Jeremy didn't know exactly what a "special friend" was, but he assumed it had something to do with her using her dildo in his ass, and he wanted that to continue regularly. During their first session together, right after Jeremy had flunked the midterm exam, the professor asserted her authority and was demanding. She introduced him to the pleasure of her dildo in his ass and changed his grade, but she hardly even let him see her nakedness. During subsequent meetings, in which he fully cooperated and it was obvious they were both deriving immense pleasure, Dixie softened a great deal. She was still in charge, but their meetings had become more like trysts between lovers, each giving pleasure and receiving it. With the door secure, he was ready to remove his clothing and kneel in front of the sofa in the usual way, but she stopped him. "Tomorrow is your final exam, and you've already got an A-plus, but this will be our last time together, and I want to make it special. It'll be more fun for me and more fun for you too." "Sure, Dixie. What do you have in mind?" Whatever it was, Jeremy expected to enjoy it, and he wanted her to enjoy it just as much. "Do you like to eat pussy?" "I love it, especially with a really sexy woman. Like you." He had no need to flatter the professor, and he wasn't. In class, she usually concealed the fact with clunky suits or floppy sweaters, but he knew Dixie had a great figure, with big, firm breasts, topped by large, dark brown nipples. Her waist was slightly plump, in a very sexy way, and her hips and ass flared alluringly. Besides her sexy body, Dixie's face was quite pretty, with a generous mouth, clear skin, and big, brown eyes. In the classroom, she wore heavy glasses to look more professorial, and her dark brown hair was always tightly pinned up in a tight bun. When they were together in her office, however, the glasses disappeared and her hair fell across her shoulders in soft waves. All in all, she was one of the most attractive women he knew, at least in her private persona. "That's good, because my pussy is badly in need of being eaten." Dixie unbuttoned her skirt and pulled down the zipper but stopped and stared at him when Jeremy didn't also start undressing. He quickly took the hint and stripped off all his clothing. In little more than a minute, the professor and her favorite student were both naked, and she was lying on the sofa, her head resting on the arm and one foot on the floor, ready for him to go down on her. Jeremy was not quite bold enough to kiss her face as he would have with a girl friend, but he was delighted to cup her succulent breasts in his hands to kiss and lick her nipples. They were already erect, and the tiny bumps and ridges felt good on his tongue as he alternated between them, licking either one, a few strokes at a time. He also enjoyed Dixie's murmurs of pleasure, so his tongue continued fondling her big nipples, until she started breathing faster, and said "That's good. Now suck them." He drew one of her luscious breasts into his mouth and sucked, while his tongue continued caressing her areola and erect nipple. As Jeremy's mouth moved back and forth between the lovely twins, Dixie's upper body squirmed on the sofa, thrusting the succulent globes into his mouth. He continued with her delightful breasts until she was ready to have him move lower on her body. "That's great," Dixie told him. "You really know how to use your mouth. But now it's my pussy that needs you." As she spoke, she pushed down on his shoulders until he ended up kneeling on the floor. Dixie sat up, spread her legs and slid to the edge of the sofa until he was between her thighs. She raised her legs and, when Jeremy moved forward, draped them over his shoulders. This was the first time he had gotten such a close look at her pussy, and it was in keeping with the rest of her beauty. In the past, he had seen a dark brown triangle where her legs met, but now Jeremy could see that her pubic hair was not as thick or as dark as he had thought. Her slit was clearly visible, and it had been pushed open by her engorged inner lips as they blossomed and, at their apex, he could see her clit peeking out from its protective hood. Her brown hair framed the swollen dark pink of those inner lips and, between the labia was her love hole, shiny-wet pink with the delectable juices that were bubbling out. The aroma of those juices drew him forward and he licked them off where they had trickled onto her crotch. They were as delicious as any he had ever tasted, and his tongue sluiced them off and into his mouth. When they had all been swallowed, he buried his face in Dixie's beautiful and fragrant pussy and started licking one of her swollen inner lips. As good as her pussy had looked and smelled and tasted, the best part was the spongy feel of the lip against his tongue. "Oooo, yeah, that feels good. Keep doing that; I love it" she urged him, looking down her body at his blonde hair and blue eyes. They were the only part of his face that was visible. Jeremy was glad to keep doing that. Her pussy was one of the best he had ever eaten, and he took pride in the way that Dixie's body responded to what he was doing. After his tongue had slowly cruised to the end of the inner lip, Jeremy briefly drew his head back. He saw that her clit had pushed its way out slightly more but it was still too early to concentrate there. He moved his face back to where he had started, devoured the fresh juices that Dixie had produced, and started licking her other lip. She didn't say anything but, from the way she was moaning in pleasure and the way her pussy was squirming under his face, Jeremy knew that Dixie was really enjoying the gentle caresses of his tongue. When he reached the end of the second lip, he looked up to see how she was reacting. Her eyes were closed and a blissful smile was spread across her face. Her head was rolling from side to side on the back of the sofa and her sexy body writhed from the intense pleasure she was getting, while her luscious breasts swayed enticingly. "She's getting ready to cum," Jeremy said to himself, seeing the movements of her body and the way her clit had completely pushed its way clear of its protective hood. He wasn't ready yet, though. Before bringing the professor to her orgasm, Jeremy wanted to prolong their mutual pleasure even more. After feasting on all the nectar that had been produced, he started thrusting his tongue against the edges of her pink love hole, relishing the juices that spurted out. Alternating between the sides, he probed the rim of that delightful place, and explored under her inner lips. Dixie's pussy was fucking up against his face as she implored him to suck her clit and make her cum. He would, but first he squeezed his tongue into the source of the nectar he had been savoring. The aroma and the flavor of her pussy were at their most intense, especially when he flicked his tongue up and down, indirectly stimulating the base of her clit and producing a fresh gusher of her delicious juices. "Yes! Yes! Suck my clit!" she implored him. Her whole body thrashed on the sofa before him. Withdrawing his tongue and moving his face up slightly, Jeremy opened his mouth to engulf that succulent morsel and started sucking on it. His tongue caressed the swollen sides and top. Dixie's became even more vocal, begging the young man to keep sucking her clit, and her pussy seemed to be trying to wrap itself around his face. He immensely enjoyed both responses, and kept sucking and licking. "Oh! Oh! I'm cumming, Dixie blurted out. Her hands seized the back of Jeremy's head and jammed her pussy up into his face, while her thighs squeezed his temples. Her ass rocked back and forth and side to side as she continued cumming until she climaxed, her back arching and ramming her pussy against Jeremy's face for a final time. After her orgasm, Dixie's hands released his head and she totally relaxed on the sofa, an even bigger smile bisecting her face. Greedily, Jeremy licked all the fresh nectar off her legs, crotch and pussy, even sucking it out of her bubbling pink hole. After he had devoured it all, he continued kneeling on the floor in front of the sofa. Jeremy had greatly enjoyed eating the professor's pussy, but now he was looking forward to what he had gone there for in the first place. Dixie was looking forward to it too, but she needed to rest for a few minutes. "That was great, Jeremy," she told him, still smiling broadly. "You really meant it when you said you had no complaints from women." That was a reference to their discussion the first time he had come to the office, when he had thought that she wanted more conventional sex with him. "I need to rest a bit after that. You really made me cum big time. While I'm catching my breath, how about getting out what we're both looking forward to using? You know where it is, don't you?" He knew. Jeremy went to the desk and opened the bottom right drawer. A plastic bottle of Aquaglide was there, along with the strapon dildo that had given him so much joy over the past few months. As he carried them over to where the professor was waiting, he realized there were two new dildos attached to it, the one that would be going into his ass and the other that Dixie would have in her pussy. I've made some changes," she told him. "Your dildo is longer and thicker and the end is more tapered so it'll slide in better. There are some pleasure bumps too, but I don't know if you'll notice those. Mine is the same except it has a spur for my clit. I don't think it'll feel as good as your mouth did, though." She arose from the sofa. "Help me get this on, please. Stand behind me and buckle the straps. She reached under her crotch to insert the dildo in her pussy. "You ate all my lubricant. You should have left some inside me so I could get this thing in more easily." "I'm sorry. It was so delicious, I couldn't resist." "That's okay. Just thinking about how I'll soon be fucking your beautiful ass is getting me wet enough anyhow." Seconds later, one hand at her crotch to hold the dildo in her pussy, Dixie stepped closer to him so he could buckle the toy around her waist. When she turned and faced Jeremy again, she smiled at the look of anticipation on his face as he gazed at the new dildo that she had ready for him. He could see it was much bigger than the other had been, at least eight inches long and thicker in proportion. He was eagerly looking forward to the immense pleasure of feeling Dixie easing it into his ass, followed by driving in and out, stretching the whole channel it would be filling, and massaging his prostate. "Okay, you know what to do now." He knew extremely well, and Jeremy got on his knees a short distance from the sofa and leaned forward to rest his arms on it. He had to be far enough from the front of the sofa that he could masturbate when the need became overwhelming. Before starting, Dixie rested her hands on his smooth, white buttocks. "I really do like your ass, Jeremy. It's nice and smooth and just the right size, a bit plump, but not fat." She slid her hands around so her fingers were fondling the insides of his ass cheeks. "You don't have a lot of hair back here like some guys do, either. I like that." Her hands left his ass and he heard the faint, squeaking noise of the Aquaglide being opened and, although he had not been told, Jeremy reached back and spread his cheeks apart. The neck of the bottle penetrated his ass slightly, and he felt the cool, pleasant sensation of the lubricant gushing in. This was followed seconds later by the even better sensation of Dixie's middle finger squeezing inside him and spreading it all over the sides of his ass, as far in as she could reach. The next thing would be for Dixie to spread more of the Aquaglide on the dildo that would soon be bringing so much joy to him. Jeremy's hands were still holding his ass cheeks apart when he felt two fingers, one on either side, pulling apart the sides of the hole that was about to be stuffed so full and so pleasurably. The next thing he felt was the tip of Dixie's new dildo pressed against the tiny hole they had created. The more tapered end worked perfectly; with a slight push, he felt it wedge inside his ass, all the way to the ridge around the head. Incredible pleasure rocketed out from around the point of entry. To Jeremy, the initial penetration was one of the high points of being fucked, but only one of several. Everything about taking this woman's dildo in his ass was more fun than he would ever have expected. He and Dixie still held his ass open and, with another push, an additional inch of plastic cock was inside, sending fresh waves of bliss crashing through his body. Fantastically good as it felt to him already, he knew the best was still ahead. It felt almost as good to Dixie, and she also knew the best part was still ahead. She loved fucking young men like Jeremy, both from the feeling of power she got from it and because of the attraction that men's asses had always held for her. After the third thrust, when she no longer needed to hold his tight hole open, Dixie allowed her hands to once again roam over the smooth, hairless contours of her current favorite. Jeremy's ass was probably the best one she had ever fucked, and she really hoped she would be able to persuade him to take one of her classes in the fall semester. Dixie much preferred fucking male students who were in one of her classes because that gave her some leverage she wouldn't have had otherwise. Even if, as with Jeremy, she didn't need it, she still preferred to have something to hold over them, as well as having a way to repay them for giving her fun. The dildo inside Dixie's pussy wasn't giving her much fun yet, but that would change after she had started driving the other one all the way in and out of Jeremy. Her steady back and forth movements would make the toy move inside her, and the spur would massage her clit. She had allocated two hours of her time to the session with Jeremy and very much hoped to use it all. He hoped to spend a lot of time in his current position too. Her next thrust, besides stretching his ass farther open and giving incredible pleasure to his rear channel, started to massage his prostate. Jeremy knew it was sometimes called the male clitoris, and the immense joy he derived from the contact gave him an idea of how happy it made Dixie and other women when he fondled or licked their clits. Waves of pleasure crashed through his body from his prostate as it was caressed by the pleasure bumps on the new dildo. They were joined by other, even stronger waves that throbbed from where he was getting so wonderfully stuffed and from his ass that was being alternately stretched and released as the dildo plunged in and out. Dixie's new dildo, being so much longer and thicker that the old one, was giving his ass the best fucking it had ever gotten. It felt so good that Jeremy, as usual, became impatient to get it all the way in. He spread his legs a bit more and moved his face closer to the sofa cushion while arching his back downward. This elevated his ass slightly, giving Dixie even better access to where he wanted her dildo. Besides the changes in position, on the next stroke, when he felt the plastic cock surging into him, he thrust his ass back to meet it, taking it in even deeper. Dixie chuckled at his reaction to her toy, which was how he usually responded. "You really like what we're doing here, don't you? I'm glad, because it makes it more fun for me too." Like most people, the professor enjoyed any kind of sex a lot more when her partner was also deriving pleasure. And Jeremy was deriving immense pleasure, so much that he didn't even interrupt his moaning and whimpering to agree with the woman who was giving it to him. With every stroke, her new dildo drove into him deeper than the previous toy had ever gone. Its thicker base spread his ass open wider than it had ever been stretched, producing greater waves of bliss that reverberated throughout his body. Even the molded bumps on the shaft, designed to stimulate the sweet spots inside a pussy, massaged his prostate gland in ever-changing ways, sending multiple swirls of delight, mingling with the other kinds of pleasure her plastic cock was giving him. With every thrust, the new toy plunged deeper and deeper into his ass, bringing him ever closer to ecstasy. Finally, the entire dildo was lodged inside, saturating his body with more pleasure than he could have ever thought possible. He felt Dixie's thighs pressed snugly against his and her hands on his hips, and he knew she was prepared to begin the deep strokes and slow, steady fucking they both wanted so much. Before she started, though, the professor leaned forward, squeezing his shoulders with her hands and mashing her succulent breasts against his back. She whispered into his ear. "This is great, Jeremy. I'm glad you like it so much too. I hope you can take one of my classes in the fall semester, and we can do a lot more of this. A couple of times a week, even." He couldn't answer out loud but he nodded his head. He would do anything or say anything to keep his ass crammed full of that wonderful plastic cock, today and for as long as he could manage in the future. Since he was not a serious student, and was attending college mostly for fun, he would arrange his schedule to include one of Professor Dugan's classes. The sure honors grade he knew he would receive, even without ever cracking a book, helped him decide, but mostly, it was the amazing pleasure he wanted to keep getting from her dildo. The Professors' Dildos CAUTION: This tale is about two women fucking a man in the ass with dildos, and has an interracial aspect. All the participants are willing and all are over 18, and they all enjoy themselves, but if these kinds of subjects bother you, you probably shouldn't read this story. * On the first day of the fall semester, Professor Patricia "Dixie" Dugan eagerly scanned the list of students scheduled to be in her Social Studies class. It was her last class of the day that semester and she was searching for one name, that of Jeremy Jones. He had promised to enroll in the class and she fervently hoped he had kept his word. Dixie had extremely fond memories of him from the previous year and, and she smiled to herself when she saw it Professor Dugan stood up. "Mr. Jones?" "Yes, Professor?" As he responded, Jeremy rose from his seat in the back of the room. She was glad to see his smiling face, although she was much more interested in his ass. As she thought of the fun things they had done together the previous term, the professor could feel moistness collecting in her pussy. "There seems to be some kind of glitch in your registration. Can you come to my office when you have a chance, and we can clear it up? My new office number is on the syllabus I will be passing out." "Okay, Professor. I'm free for the rest of the afternoon after this class ends, and I'll come to see you then." The thought crossed his mind that he expected to do some really good cumming in her office, and that the professor would too. "Good. I'll see you there after class." She smiled at his double entendre, agreeing with it and hoping nobody else would catch on to it. Professor Dugan passed out the schedules and other necessary papers to Jeremy and the others. She was eager to see him again and, since nothing much ever gets accomplished on the first day anyhow, she dismissed the class after talking to them for a few minutes about her expectations and requirements, including what she expected them to do in preparation for the next class. Jeremy would be very happy to join the professor in her office. He also had memories, maybe even more pleasant than hers, of what had transpired there. He remembered her body extremely well, with her large breasts and shapely ass and delectable pussy. He remembered her surprisingly pretty face with her big, brown eyes. More than anything, he remembered her new dildo. It was longer and thicker than the first one she had used, and he had gotten some of the greatest pleasure of his life when she put it on and gave his ass the longest and best fucking it had ever gotten. He waited a half hour before starting to look for the professor's new office, giving her plenty of time to get there and do whatever needed doing to prepare for him. Jeremy hoped she would have the same sofa there, the one he had leaned against while kneeling on the floor and reaching back to spread his ass cheeks. It took him a few minutes to find the right place and, after knocking on the door, he thought he heard two voices inviting him to enter. When he walked through the doorway, he saw the new office was larger, and the professor's desk was right in front of the entrance. "Hello Dix...Professor Dugan," he greeted her. Jeremy had suddenly noticed another person, seated behind a desk by the far wall. The woman he had come to see had combed her long brown hair out of the tight bun she had worn in the classroom, and had taken off her boxy suit jacket. Jeremy wasn't sure, but he believed she had also taken off her bra. Even though she looked almost ready to start giving his ass a workout, he thought he'd better be careful in front of the new and unknown person. "Hello, Jeremy. I'm still Dixie to you, at least in here," she responded. "And this is Professor Sarah Black of the Women's Studies Department. We both hope you'll be calling her Sally." Jeremy looked at Professor Black. She was a tall, very pretty young African American woman, with big, brown eyes, a clear, milk-chocolate complexion and short, black hair. Sally stood up and smiled prettily to acknowledge the introduction and he saw she was wearing a red jersey and blue jeans, both filled out very sexily. She smiled and greeted him by his first name. Professor Dugan continued. "Because of staffing changes, I had to move from my old office to share one with another professor. Sally and I are old friends, and we arranged to share this one. Although we are in different departments, we have similar interests. In fact, almost identical interests." Sally smiled even more broadly. "This is what she's talking about, Love." She reached into her desk drawer and pulled out a bottle of Aqualube and a strapon, almost identical to the one Dixie had worn a few months earlier, except that it had a big, black dildo protruding from the front. Dixie continued. "That's right. Anyhow, what we would like is to take turns with you, doing what you and I enjoyed so much the last time we were together in my old office. You don't have to if you don't want to, and it won't be held against you. If you prefer, Sally will leave and you and I can do what I think you came here expecting. Or, I can leave, and you can get better acquainted with Sally and her strapon. Or, you can turn around and just walk away, but I'm sure you came here for some more of the good fucking we shared last year." Jeremy looked at the two women, and the choice was a no-brainer. Just from the sight of the big plastic cock protruding from Sally's toy, his ass was twitching in anticipation. Especially, he had noticed the molded pleasure bumps and remembered what those on Dixie's strapon had done for his prostate gland. His cock was already getting hard from the thought of two beautiful women taking turns fucking him, maybe a couple of times each. He hoped he would have a chance to eat the pussy of the one who wasn't behind him, pleasuring his ass with her dildo, and wondered how to broach that possibility. "Ladies, it is the primary fantasy of every red-blooded American boy, including me, to have a threesome with two beautiful and sexy women. Let's do it! Who goes first?" Dixie got up and went over to the door to bolt it and pull the shade over the window. Sally also got up and Jeremy joined her in the middle of the room, where she hugged him. After letting go, Sally slipped around behind him and squeezed both his ass cheeks in her hands before hugging him again, this time from behind. She definitely was not wearing a bra. "I'm sure you remember the sofa from my old office," Dixie pointed out, smiling at Sally's proprietary actions and hugging Jeremy from the front. When that embrace ended, all three of them stood, contemplating the sofa and thinking happily of what they were about to start doing on it and in front of it. Dixie continued. "I hope you don't mind, but we were pretty sure you would pick the threesome, so Sally and I flipped a coin before you got here. She won, so she gets to fuck you first. I hope you can eat my pussy while she's doing you, though." Sally grinned and walked behind Jeremy again and resumed fondling him. One of her favorite sexual activities was fucking a man in the ass with her strapon, and Jeremy seemed to be perfect for it, short, rather chubby, with blonde hair, soft, fair skin and blue eyes. If she had placed an order with Central Casting, she would have asked for a young man who looked exactly as he did, and she expected to enjoy fucking him as much as her friend had described. "Dixie has told me you have a really great ass. It feels pretty good but I can't really tell, with all these pants and things you've got on." Correctly taking that as his cue, Jeremy stepped over to the sofa and started undressing. First, he sat down and took off his shoes and socks and set them on the floor in front of one end. Standing up again, he removed his jacket and shirt. Just as he was starting to unbuckle his belt, Sally put her hands on his to stop him. "Let me, Love. I won you, fair and square, so I get to take your pants off." She unbuckled his belt, unfastened the button on his waistband and unzipped the fly of his pants. Slowly and sensuously, Sally pulled the outer garment down to the floor, and knelt to pull the legs around his feet. Still kneeling, she smiled up at Jeremy, who was wearing only his jockey shorts, clearly showing his cock, which was stretching the fabric as he avidly thought about what would soon be happening. Instead of idly watching Sally undress the man they were going to be sharing, Dixie started matching her actions with her own clothing. She quickly divested herself of her white blouse and hung it over a chair back. As Jeremy had expected, she was not wearing a bra. She had certainly been wearing one in class but must have removed it after she returned to her office. As he admired her luscious breasts, she smiled at him and unfastened her skirt, but paused before removing it. "I hope you like what you're seeing so far. You know what else I have for you." Jeremy knew, alright. He had eaten many pussies and hers was one of the best. There had only been the one time, at their last session the previous semester, and all summer long he had been hoping for a chance to bury his face in the same soft and delightfully fragrant place. As he watched, Dixie let go of her skirt and it dropped to the floor, leaving her completely naked. Apparently, she had removed her shoes and stockings and all her undergarments while waiting for him to join her and her friend. As Jeremy watched Dixie undressing, Sally got to her feet and stood off to the other side. Smiling lewdly, she crossed her arms in front of herself and took hold of the bottom hem of her jersey. With a quick motion, she peeled it off over head, letting her luscious breasts bounce as the thin material ceased restraining them. "You like these?" she asked, cupping the twin beauties in her hands. Jeremy grinned and nodded his head, and Sally smiled again. "I have more to show you too." Deftly, she unbuttoned and unzipped her tight jeans and pushed them down to the floor. After stepping out of them, she kicked the pants aside and stood before Jeremy, as naked as Dixie. He realized that both women had taken off their shoes and stockings and all their undergarments while waiting for him. Sally sauntered around behind him and held her lovely naked body against his back, hugging him around the waist and pressing her hard nipples against his skin. Jeremy loved the sensation, but he knew they would feel even better when he was kneeling in front of the sofa and Sally was leaning over him with her big, black dildo plunging in and out of his ass. "Let's see what you're hiding under here, Love." She thrust her hands down the front of his jockey shorts and fondled his cock, which was erect and straining to get free. Sally reached in further and held his balls gently in one hand and wrapped the other around his erection. "Mmmm, nice big cock," she murmured. She released the stiff object of her admiration and separated her hands, moving one across each of his hip bones and around and down until they were cupping his smooth, plump buttocks. From there, she moved her hands together until they met, and used them to spread his ass cheeks. Her fingers moved to between the soft hemispheres and gently fondled the very sensitive puckered area there. Shivers of joy shot through Jeremy, from the soft touch of Sally's fingers and in anticipation of the fucking she would soon be giving him. She wasn't through yet. Jeremy felt the tips of two fingers -- probably her middle ones -- at the sides of the hole that was the object of the women's lust. They spread the sides apart and the one on the right pressed against the opening that was being created. He was sure what Sally wanted to do, and he bent forward to help her finger gain entrance to his ass. The tip wiggled there briefly before pushing its way inside, followed by more of her digit, up to the second knuckle. He smiled and cooed his delight. Giving the young man a small sample of the greater pleasures he was soon to enjoy, Sally's finger fucked in and out of his ass a few times. Loving the sensation and wanting more, he squirmed and thrust his plump buttocks downward, as if trying to induce her pleasuring finger to penetrate him more deeply. "You were right, Dixie," Sally said to her colleague. To Jeremy, she added "Dixie said you had a really great ass, Love. Smooth and soft and hairless, and she was right. I can hardly wait to get my cock inside you." Sally withdrew her finger but continued to caress the insides of Jeremy's ass cheeks for a few seconds before taking her hands out of his underwear. She put her thumbs back in the waistband and pushed down, working the elastic around his cock, which had gotten even harder as a result of Sally's fondling it and finger-fucking him. Once the shorts had cleared his ass, she let them go. They fell down around his ankles and Jeremy stepped out of them and kicked them in the direction of his shoes and socks. All three of them were equally naked and looking forward to a wonderful afternoon of sex. Once she knew Sally's foreplay had ended, Dixie walked over to the sofa, sat down, and scooted forward so her pussy was hanging over the edge, ready to share pleasure with Jeremy's mouth. He knelt on the floor and walked on his knees to where her legs were spread and waiting for him. From what she had seen and heard already, and what she knew she would be seeing and hearing and doing, Dixie was in a high state of arousal. She raised her legs and, when he leaned forward, placed them on the young man's shoulders. He responded by wrapping his arms around her thighs until his fingers met in her soft pubic hair, and leaning forward to lick up some of the fragrant juices that were trickling out of her pussy. They tasted even better than he remembered. "Have fun, kiddies. I'll be right back with The Big, Black Bull," Sally remarked, as she walked over to retrieve the Aqualube and her strapon from where she had left them on her desk. Holding the toy so the dildo was bouncing up and down in front, she stepped into one leg hole, then the other, and pulled the straps far enough up so the other dildo, also big and black and covered with pleasure bumps, was just touching the lips of her pussy. After playing with Jeremy's ass, Sally was extremely wet, her juices running down her thighs, so she reached between her legs to push the tip of the dildo inside her pussy. With it started in place, she pulled the straps the rest of the way up and adjusted the clit spur so it would be in a position to do her the most good. The toy was not imbedded all the way inside her, and the spur was not yet against her clit, but they would be adjusted when Sally began fucking Jeremy. The toy had come equipped with two spurs, but Sally had removed the one from the dildo that would be fucking Jeremy. She pushed his legs wider apart and knelt between them so she could prepare his ass. Dixie saw her colleague's preparations but Jeremy was looking away and concentrating on the pussy in front of him. He drew his face back to gaze on it, finding it to be truly a thing of beauty, surrounded by soft, curly brown hair, and possessing lips that were swollen with lust and blossoming through her slit. The blossoming petals surrounded her adorable pink hole that he knew to be the source of those delicious juices. At the upper end of her engorged lips, he could see her precious clit, also swollen, and pushing its way out from under its protective hood. After admiring the sight, aroma and taste of Dixie's pussy, Jeremy was about to bury his face there, when he felt Sally's hands spreading his ass cheeks and her voice interrupting his thoughts. "Quit hugging Dixie's legs, Love, and reach back here and open your ass for me. The Bull and I are about to give you the best fucking you have ever gotten." Although he was reluctant to delay eating a pussy as lovely as Dixie's, Jeremy was also eager to get Sally's big dildo imbedded deep inside his ass. He released his hold of the legs that continued to frame his face and reached back to spread his ass cheeks as Sally had requested. His tongue continued caressing one of Dixie's delectable pussy lips, but he concentrated more on helping Sally with what they both wanted her to do. The first thing he felt was the familiar neck of the bottle inserted in him and, immediately after that, the equally familiar rush of the cool lubricant. This was followed by Sally's finger inside him again, but this time she was behind him and could drive the digit all the way in to her knuckles. She took her time spreading the Aquaglide, fucking her finger in and out of his ass and giving him a better foretaste of the extreme pleasure that he knew would be following momentarily. Sally had applied the lube to her dildo right after putting it on and, with Jeremy ready, she once again put the tips of her middle fingers on either edge of his ass to pry open a small hole. She pressed the tip of the dildo against the opening being created and, with a firm push, the head of The Big Black Bull wedged inside Jeremy. Waves of intense pleasure washed through his body from the place of entry, and he murmured happily. It had been almost three months since he had felt a dildo spreading open the rim of his ass, and it felt even better than he remembered it. Best of all was his knowledge that the pleasure would quickly become much greater. It became better immediately. While he and Sally held his ass open, she gave another thrust, and almost an inch of thick plastic cock plowed into him. He moaned from the incredible pleasure the toy was giving him and, the next time he felt Sally's dildo start to burrow deeper inside, he thrust his ass back to meet it, taking in almost three more inches. Besides stretching the opening and the connected channel the way they hadn't been stretched in too long, the molded bumps on the shaft of the toy were starting to massage his prostate gland, saturating his body with a new kind of delight. Intense pleasure throbbed through him from the path of the dildo, making him writhe in bliss. As wonderful as it already was, he wanted more. "Give it to me, Sally. Give me all you've got." He arched his back downward, raising his hips and presenting an even better target to the woman who had started to fuck him. His ass squirmed in front of her, helping Sally do what he wanted, which was what she very much wanted also. She laughed at his eagerness. "You really like this, don't you? That's good because it makes it even more fun for me." With her hands on the young man's hips for leverage, Sally thrust forward again, and again and again, until almost the entire length of her big dildo had found a home in Jeremy's very hospitable ass. She ran her hands all over his cheeks again, including the smooth insides, and leaned forward to grip his shoulders and press her erect nipples against Jeremy's back. "I really love your ass, Jeremy. We're gonna have us a lot of fun today." Sally put her hands back on his soft, white hips and began to fulfill her prediction. While his ass was being crammed full of the plastic cock, Jeremy had paused in eating Dixie's pussy. After the dildo started surging all the way in and being slowly withdrawn, only to plunge back into him again, his tongue returned to fondling the swollen labia before him. Her pussy was squirming in front of his mouth so, to keep her in position, he once again wrapped his arms around Dixie's thighs. As wave after wave of three kinds of pleasure inundated his body from where Sally was working her toy, a fourth kind, delighting all his senses, swirled outward from where his face was pressed against Dixie's marvelous pussy.