“Mr. McCoy, I just have to start getting higher grades in your class if I’m going to get admitted to any of the best colleges. I’m acing every class but yours and I’d do anything to get straight A’s from you too.
“Anything? Do you really mean that?” His smile widened as he asked her that and lecherous thoughts swirled through his mind.
“Yes, I do. Anything. Anything at all. I would even be willing to have sex with you but I’m a virgin and I have to stay that way until I’m married. My parents are very strict and so are the mother and father of my fiancé. Even so, I would be willing to have sex with you but it would have to be some any way I can do it and still keep my virginity?”
“I’m quite sure we can work something out, Ruth. Suppose you come to my office after school ends today and we’ll see if we can think of something.”
Dennis McCoy already knew what he was going to be thinking of and he hoped Ruth would be as willing as she said she would be. She was about the hottest girl in the high school where he taught Geometry, with long red hair, green eyes and a few scattered freckles that enhanced her perfect ivory complexion. Her breasts were big and shapely too but neither they nor her face was Ruth’s main attraction. As he watched her walk out the door of his office in her long knit dress, he knew what was. He was a man who loved female asses and the body he was eying had a bottom that was as close to perfect as any he had ever seen, big and curvy with a truly delightful sway. He would talk with her after classes ended for the day but he already knew what he wanted to do to her later when her dress would be bunched up above her waist and she would be leaning over his desk.
Shortly after the bell rang ending the school day, Ruth returned to his office. Although inexperienced, she knew there was a way for a woman to have sex with a man without breaking her maidenhead, and she had done it, but she was naively hoping Mr. McCoy would not have thought of it. If he had, and he insisted on it, she would let him have his way with her because a first class college was so very important in her plans. She was willing to go that far but would still refuse to let anybody fuck her pussy before marriage and after the wedding, it would be only her bridegroom.
She needn’t have worried about her maidenhead because the lecherous Dennis McCoy had been thinking of only one thing since watching her ass swaying as she left his office earlier that day. The first thing he had done was to look up the sexy redhead’s date of birth in her high school records and learn she had turned 18 over a month ago. He had made sure he had a squeeze bottle of good quality lubricant because he was aware it would be necessary but had decided to pass on the condoms. He knew Ruth couldn’t possibly become pregnant from being fucked in her ass and he was confident she would have no STD or AIDS. The last thing he did before her anticipated visit was to put a roll of paper towels on his desk but otherwise clean off everything there so she could bend over it while he raised her dress and peeled down her panties.
Ten minutes after classes ended, Ruth arrived in Mr. McCoy’s office and was rather dismayed to see him there and not wearing his coat or tie. She had hoped he would have left already, thereby relieving her of her promise but, since he hadn’t, she was determined to go through with it. “I’m here,” she announced and turned around to lock the door and pull down the shade before sitting on the chair next to his desk. “Have you decided what you want to do?”
She expected him to want to be sucked off, which would not be that much of a problem to her. Although a virgin, as she said, Ruth had sucked her fiancé’s cock several times and it been rather fun. The young man had never done anything to reciprocate but her own fingers on her clit had taken care of her climaxes. She expected that would be what she was called on to do that day and started to go around the desk so she could get to her knees while the teacher remained in his chair and enjoyed her attentions. The only things she was concerned over were how long it would take and what his semen would taste like and whether or not he would expect her to swallow it as her fiancé liked her to do when he came into her mouth. Therefore, Ruth was surprised when he got up from his chair and guided her to a spot in front of his desk.
“Put your hands here,” he instructed her, referring to an area that was free of any clutter. “Lean forward and press your legs against the edge of the desk.”
Still wondering what was going to happen, she did as she had been told and watched as Mr. McCoy went back to the drawers of his desk, removed some objet or other and returned to stand behind her. She felt him unbuckle the belt around her waist, place his hands on her hips and stroke slowly downward until he reached the hem of her dress. Not until she became alarmed when he started to raise her dress did she say anything to him.
“Mr. McCoy! What are you doing?”
“I’m getting you ready to do what you said you would do.”
“But I can’t do that! I can’t let you take my virginity.”
“Don’t worry. I’m not going to get near your cherry.”
Ruth began to realize what the teacher’s intentions might be. Occasionally, she had heard an angry man say something like “Fuck you in the ass” to another man but she had never thought about that as even being possible. Ruth had also, while taking a shower, inserted a finger in her own nether hole and it had felt rather good but that was just a finger. She was certain the cock of the geometry teacher would be much thicker and longer and doubted it would even fit inside such a small opening the way he seemed to want. She had made a promise to him but had not known at the time what might be involved.
“Wouldn’t that hurt? I mean what I think you might be thinking about.”
“No. Well, just a little at first but it should feel good once we get going. If it hurts too much, I’ll stop but millions of people do it every day and most of them really like it.”
“Can’t I just give you head instead of that?”
“No. You made a promise to me and I expect you to keep it.”
“But I don’t want to do that.”
“Oh? Do you want to go to a quality Ivy League university or some other place equal to that or would you rather have to enroll at Podunk Community College? Because that’s the only place that’ll accept you with the D Minus you’ll get in my class.”
That gave Ruth something else to think about. Straight A’s would get her the scholarship she needed and admission to the best schools in the state – in the world even – with all the benefits that would be involved after graduation.
“Will you really stop if it starts to hurt too much?”
“Of course. I have no intention of hurting you. I just want to have some fun and I really think you’ll like it too. Gay men do and a lot of women like it better this way too.”
“Alright. Just tell me what I have to do.”
“For now, just keep leaning against the desk with your feet together.”
With Ruth doing what he wanted, Dennis finished raising her dress above her waist and gathered it so it would rest on his desk and be out of their way. Thinking he might need something nice to hold onto, he reached up even farther, unhooked Ruth’s bra and pulled it off to leave it draped over the back of the chair she had used briefly. He sat on that same chair and removed his shoes, socks, pants and underwear, grinning at his stiff cock when he finished. She was still wearing her shoes and sox but he didn’t worry about them. Naked below the waist, he stood behind Ruth and slowly pulled down her white cotton panties, taking his time about it because he considered the stripping to be comparable to the unveiling of a work of fine art.
With her panties off, he gazed raptly at the spectacularly beautiful ass he was about to fuck. It was probably the most gorgeous one he had ever seen naked, with her hips curving out from her waist and back in to merge with her thighs. The lovely cheeks were two perfect hemispheres that jutted from her back, curved around and down and back and slightly up until they met the backs of her legs. The skin covering this marvel may have been the most beautiful part of all, creamy white and unblemished, and Dennis could hardly wait to get his body pressed against her while he was plunging his cock in and out of this place of spectacular beauty.
But there was one detail that had to be attended to first. “You certainly have a beautiful bottom, Ruth,” he told her. “But I need you to reach back and spread your cheeks for me. And move your feet apart,”
She reached back with her hands to part the halves of the gorgeous globe and he gazed at the new glory – her lovely pink rosebud between the satiny white hillocks. When he reached in to open the pink bud, his hand brushed against the skin that was like Damask and lined the insides of those cheeks. She was so gorgeous, he thought of licking her but he didn’t want to take the time to do the thorough washing that would have been needed. Although distracted by her beauty, he concentrated on prying her open enough to insert the tip of the squeeze bottle of lubrication.
“Oh!” the sexy redhead responded as the cool liquid squirted into the place where nothing but her own fingers had ever been before. “That feels good. Funny but good.”
“I’m glad, Ruth. It’s supposed to feel good.”
After removing the nozzle of the bottle from her ass, Dennis slowly eased the middle finger of the same hand into the oily hole that had become much more easily accessible. Ruth’s body squirmed against the desk because the digit was going so far into her and felt even better than her own soapy fingers had while in the shower. So far, she was really enjoying her first anal sex experience but she was also aware that a man’s dick, at least that of her husband-to-be, would be much bigger than anything that had ever penetrated her before.
When he finished covering his cock with the lubricant, everything was ready. Dennis reached back between the teenager’s cheeks with the same hand, pried open a small opening again and moved closer while guiding his hard organ with the other hand. When he made contact between the tip and the tiny orifice that he was about to stretch, he stopped and rubbed the head of his cock against it to spread the lubricant better and to make the first shallow insertion.
“That still feels really good, Mr. McCoy. So far, everything has.”
“I’m glad to hear that. But the next thing I do will hurt just a little and, after that, everything should feel good.” Having said that, he pushed forward and the head of his cock wedged its way into the slippery hole before him.
“Oh!” Ruth gasped as she felt the thick invader squeeze its way into her ass. “Ahhh,” she continued as the small amount of initial pain immediately started to evolve into pleasure.
“How does that feel? Does that hurt?”
“Oh, no. Just a little at first but it feels great now.”
“Good.” Dennis thrust forward again and almost an inch of his cock burrowed into the place that was being so hospitable.
Ruth sighed in bliss and spread her succulent cheeks slightly farther, believing if the small penetration felt that good, deeper would be better. She was right in that belief. The hard shaft burrowed its way almost another inch into her, and the currents of joy rippling through her body more than doubled. She moaned loudly from the extreme delight she was feeling and her body started squirming against the edge of the desk. Wanting more, Ruth kept holding her soft, white cheeks spread as widely as she could until she felt a hand being placed gently on either of her hips.
From the way the teenager was acting, it was obvious she was getting as much fun as he was which made Dennis happy. He preferred the woman have a good time during sex with him and he knew the antics Ruth would soon be going through would make the fucking so much better for him. His cock was deeply enough inside her ass that he no longer needed to guide it so he used one of the paper towels to wipe the excess lubricant from his hands and placed them on her soft hips. He enjoyed the contact and would be able to pull back on them for leverage as he drove his cock farther into her.
With the next stroke, Ruth felt Mr. McCoy pulling back on her hips so she thrust her ass back to meet him. A wave of unmitigated pleasure washed over her body as his cock imbedded itself inside her and she groaned in bliss. The fabulous sensation of having her ass stretched and the adjacent channel crammed so full was like nothing she had ever known or even felt in her most lurid adolescent dreams. The horny teacher kept his cock in place while her whole body was writhing in joy and she was shifting back and forth from one foot to the other as wave after wave of intense carnal delight crashed through her body.
Finally, he slowly withdrew and Ruth felt a small sense of loss but that didn’t last very long. When she felt his cock surging back into her ass, Ruth was in such a hurry to have the hard giver of joy imbedded again, she fucked back to meet it. Once again, she groaned in pleasure as their bodies came together, this time burying his cock so deeply that his pubic hair was tickling the very sensitive insides of her ass cheeks. They stayed like that for over a minute while great breakers, not merely waves, of joy crashed through her whole form.
Dennis was having a great time too. Ruth’s extremely tight ass was probably the best place his cock had ever been and the movements of her body made the fucking even better for him. For this purpose, he had bought the best quality personal lubricant he could find and it was worth the small extra price. The oil had completely liquefied and he felt no friction as he plunged his entire shaft in and out of her, just the tightness and the massaging by her internal muscles.
Over and over, Dennis McCoy’s cock plowed into Ruth’s ass and she fucked back to meet every stroke. The pleasure she was receiving was excruciating but there was another feeling also mounting within her body. While sucking off her fiancé and, occasionally at other times, she had brought herself to a climax by fondling her clit and the new sensation was a little like that, except for being so massive those other times paled in comparison.
From the erratic movements of the teenager’s body and her sounds of delight, Dennis knew Ruth was getting close to coming, as was he. “Do you want me to play with your clit,” he asked.
“Yes! Please, can you do that? I think I’m gonna come any minute.”
Dennis reached around her hip and found her clit, which was so swollen with her lust it had crowded its way out from behind its protective hood. Ruth’s whole pussy was dripping wet from her juice and he scooped some of it up on his fingers, being careful to avoid making a penetration, and licked it off. The fresh honey was delicious and he repeated this several times, while hoping he might get a chance to eat her pussy during some future tryst in his office or elsewhere. After licking his fingers for the last time, he gently used his thumb and forefinger to squeeze Ruth’s clit between two folds of her inner lips.
He started slowly stroking the engorged morsel, in the same tempo as the thrusts of his cock into her and Ruth matched his pace as she rammed her ass back to meet him. Knowing they were both on the verge of coming, he started plunging his cock into her at a faster pace. Her movements became wilder; she kept shifting her weight from one foot to the other, as if in some kind of strange dance, and her upper body swung and swayed from side to side. Whatever her other movements, she continued to jam her ass back to meet the strong, deep thrusts of the hard cock in and out of her thoroughly fucked ass.
“Oh! Oh, my god, I’m coming,” the happy redhead sang out and Dennis was glad the walls were thick enough to muffle her voice.
Ruth’s movements were so erratic, he was also glad he could continue to press her thighs against the edge of the desk and use his arms to prevent her from falling to the side. He kept driving his cock in and out of her perfect ass until his own climax bubbled up and exploded, shooting a big wad of cum into her bowels. Dennis continued driving his cock in and out until he had ejaculated two more times and was through, at least for that day.
Before his last burst of semen gushed into her, Ruth uttered a subdued cry of ecstasy as she also reached her orgasm. Her muscles clenched and relaxed immediately after and her upper body sprawled across the desk. Dennis was right on top of her but he kept his hands splayed on the wooden surface to avoid putting too much of his weight on her young body. Their fucking was over but they stayed in that position for a few minutes to rest and catch their breaths.
Although they both felt bad about ending the connection, Dennis’s cock grew soft and he had to withdraw it from the gorgeous ass where it had given and received so many delights. There was still one more moment of pleasure waiting for him and it was ready to happen. Even with his cock no longer inside, Ruth’s ass remained dilated and, as he watched, his white cum, combined with the used lubrication trickled out, with some of it joining the juices from her pussy, and ran slowly down the insides of her legs. After he used paper towels to wipe off most of the trickle, it was time for him to live up to his part of the bargain.
“You will get close to perfect grades in my class for the rest of the year, Ruth, but here’s how we’ll have to do it. I’ll provide you with advance copies of the midterm and final exams and all the answers will be included. You can get grades as good as you want but I suggest you get slightly less than 100%, just to keep anybody from getting suspicious enough to say anything.”
“Thanks, I’ll do that. One thing though,” she added with a lascivious grin on her face. “Can I come back here a couple times a week to do more of the same thing for extra credit?”