“So what did you think of your first real day of school?” Charity asked her when they finally got back to their room that night. After her shower Jessica had joined her friends for dinner and then they’d chosen (from a long list of possible activities) to watch the movie that the school was showing that night, Fired Up. The movie was very funny and not very sexual (although there was plenty of sexual comedy) and Jessica appreciated an evening of relaxation that didn’t include sexual anticipation, after the many orgasms she’d already had over the day.
“It was fantastic,” she said. “I already feel like I’ve learned so much. A lot of it seems like common sense stuff now that I stop to think about it, especially when it comes to heightening anticipation for a more satisfying result, but for some reason I just never thought of it that way before.”
“Yeah, it kinda blew my mind my first session,” Charity said, peeling off her clothes and getting into her nightgown for bed. “The basic stuff they teach isn’t really like teaching so much as demonstrating how good it can be if you take the time to do it right.”
“Yeah, exactly,” Jessica agreed, happy to slip between the sheets on her bed. The mattress was so soft and it felt so good to just lie down. Unlike last night she was completely sexually sated after the day’s activities, although she still glowed to think about tomorrow. She was nervous too, because she would have her first Anal Play class in the morning, but things had gone so well today, she just had to trust in the school and its talented Teachers that she would find tomorrow just as blissfully satisfying. “Basic Intercourse they didn’t even bother to give a lecture, it was just get straight into it… although that might’ve been because it was a one to one ratio of students to Teachers, pretty much, and I definitely appreciated the tutelage.”
Charity snickered. “You’re just lucky it happened that way. It doesn’t happen often with Basic Intercourse. With some of the other classes, definitely. Sometimes it just depends on what courses the Teachers that session are interested in helping out with. There were six of them in my Fellatio class today.” Both girls giggled. “We should probably try to sleep though, I don’t know about you, but I’m exhausted!”
“Definitely,” said Jessica. She would have liked to continue gossiping, but she knew that Charity was right. Tomorrow was going to be another busy day. “Good night!”
Justin and Chris argued late into the night about who would claim Jessica as a student in her morning classes for the week.. Finally they agreed that Chris would take the Basic Intercourse classes on Thursday and Friday and Justin would take the Anal Play classes. Privately, Chris thought that he’d gotten the better deal since the first two classes of Anal Play were all devoted to lectures and stretching, and he’d get to sleep with Jessica first. Privately, Justin thought he’d gotten the better deal, the taking of Jessica’s anal virginity.
The next morning Jessica woke up feeling absolutely delicious. Her body felt sated so sated from yesterday that she couldn’t possibly imagine even wanting to have another orgasm. But when she was in the dining hall, she saw that several of the Teachers were sitting and eating with students, and when she caught Mr. Winter’s eye she blushed and felt her insides tighten at the memory of the intense orgasms she’d experienced with him. That moistening between her panties was enough to being a slow build of anticipation that continued into her Self Pleasure class, the first of the morning. This time as she focused on herself, she also focused on the visual of Mr. Winter’s deep, probing gaze, his strong hands, and his thick cock. This visual was aided by the realistic dildo that she was using in class.
Leaving the class feeling very pleased with herself, the only toys she’d ever successfully masturbated with all been vibrators, she still felt very nervous heading to Anal Play. The few times her ex had tried it with her it had hurt so unbearably that she’d made him stop before it really went anywhere. According to Charity this was because they hadn’t stretched her properly, and she’d reassured Jessica over and over that no one was expected to have anal sex during the first two classes, in fact, she told Jessica, that’s why everyone had to sign up for at least three classes.
Walking into the room, she saw that this was quite a popular class for Teachers to help out with. Although there were ten students (here the girls outnumbered the boys, seven girls and only three boys) in the class, there was also a Teacher for each and every one of them. Mr. Winter was there, and as soon as she slid her eyes from him, she was held arrested by the gaze of Mr. Flood. He was staring at her with such intensity that she felt her nipples tightening and her cheeks flamed hot as she remembered how hot she’d gotten watching Mr. Flood whip Charity during the Light BDSM class demonstration, how she’d wished it had been her trussed up to the couch, open to his every whim.
By the end of next week, she told herself fiercely, I will stop blushing.
She was so involved in scolding herself, looking at the floor, that it wasn’t until she saw shoes standing right in front of her that she realized a Teacher had come to instruct her. Guiltily she looked up directly into the chocolate eyes of Mr. Flood.
“Hello Jessica,” he said smiling down at her with obvious delight. “I’ll be your Teacher for this class this week. For Anal Play you are assigned the same Teacher for each class, as each person’s body is different and so it’s best if the person working with you doesn’t need to get reacquainted with your body every class.”
Nodding, she felt a little numb. Although he didn’t say it outright, he was discussing getting intimately acquainted with her asshole, an area she’d never been comfortable with, and the idea of having someone intimately acquainted with it seemed both perverse and incredibly erotic.
All around the room were small leather triangles, the highest part about a foot to a foot and a half off the floor. Mr. Flood led her over to one and then stopped, looking deep into her eyes. Jessica blushed at his intense scrutiny. He turned her on a little bit but… she could feel her butt cheeks clenching. She wasn’t sure what she’d gotten herself into.
“You’re frightened,” he said, and it wasn’t a question, but Jessica nodded confirmation. He smiled at her, reassuringly. “Don’t be. This is going to feel wonderful.”
“How would you know?” she asked, a little rudely. Mr. Flood’s smile widened, to something almost mischievous and she felt her lips curving in reply.
“Anal Play isn’t just for women and gay men, you know,” he told her, his eyes glinting. Jessica gasped a little as she took in his meaning. He really DID know! “I’m not going to hurt you. We’re going to take this nice and slow. Have you had any experience with anal before?”
Jessica blushed very deeply and looked down, the memory of not being able to please her ex, the pain of him trying to push inside of her, cut deep. Maybe if she’d been able to do anal for him then he would have been more amenable to playing around with tying her up. But neither of them had been able to fulfill each other’s desires.
“Sort of,” she confessed. “But it hurt too much so I made him stop.”
“Then he wasn’t doing it right,” Mr. Flood sounded so confident, so self-assured in his assessment that Jessica felt a little bit of her anxiety unknot. “But let’s see if we can’t relieve you of some of your fear. Also, being scared is just going to make you more tense. You want to be aroused, so that your muscles are relaxed.”
Then he kissed her. He was just as expert a kisser as Mr. Winter had been, but his hands tended to roam more, rather than holding her. She clung to him, feeling his hard shaft beginning to swell, growing against her body as he ran his hands over her back, one reaching down to grip her ass, the other sliding up to massage her breast through her shirt. Remembering Mr. Winter’s instruction, she let her hands massage along Mr. Flood’s shoulders, digging in her nails a little as he thumbed her nipple and the pleasant sensation hummed through her body.
His fingers massaged her buttocks, pulling inch after inch of her skirt up until his fingers met bare flesh. Then he dug in, squeezing the tender flesh almost cruelly, and she cried out against his mouth in hot passion, pressing her hips against him and feeling his hardness digging into the soft flesh of her front.
Then he released her lips and helped her to bend over triangle. It was shaped so that her hips were held high in the air by the highest part of it, and that side was rounded not sharp so that nothing was digging into her, and her breasts and face pressed into the sloping side, leaving her ass and pussy entirely open and vulnerable to him. His hand pressed between her thighs, spreading them and taking away all pretense of modesty as he tucked the hem of her skirt up around her hips.
Another shiver of fear went through her.
“Relax,” he told her, “I’m not going to do anything yet. We’re still working on arousing you, until you want to have something inside of you.” Fat chance of that happening, she thought to herself, as long as he’s talking about my ass. Her pussy however… she’d be perfectly happy to accommodate him there right now, even though doggy style had never been her favorite position.
Resting his hands on the fleshy heart shape of her ass, he massaged the globes of flesh with his hands, spreading her pussy and ass crack open and close, over and over again. When she felt him gently blowing air over the heated, moistened flesh of her pussy, she moaned. She wanted his hands inside of her, not on her ass!
Justin couldn’t believe how responsive Jessica was, her pussy was a beautiful glistening flower, petals moistened by dew, and she smelled absolutely amazing. Tucked above this wonderful scenery was that dark virgin territory, a small pink rosebud that had yet to unfurl. He felt lucky, so very lucky that he’d be the one to introduce her to anal pleasures. Although he felt entirely scornful of whatever past lover had mistreated this adorable, tiny crinkled hole in the past and put her off of anal, he felt privileged to be the one to show her why she should give it a second change. And he couldn’t wait until he was easing his own hard shaft into the tight space.
Leaning forward, he let his tongue swipe up the center of her pussy, and was rewarded with a gasp and the delightful sight of her moving her hips up and down, begging for more. She was sweet on his tongue, like peaches and honey, and he was not at all averse to leaning more and starting to try and lick up all the moisture that was gathering at her center. It was a losing battle as the more he licked, the more she produced, but it was a battle he was happy to fit.
As her breathing started to change and she started to lose herself in the pleasure, the muscles of her butt relaxed, and the little bud nestled between her cheeks became easily visible without him having to use his hands to catch a glimpse. He brought one of his hands down from her cheek and began rubbing her pussy with it, as his tongue quested higher.
Jessica was lost in the sensation of having her pussy so carefully attended to. She’d never had anyone eat her out like this, from behind. It had always been lying on her back where she’d been able to watch, to grab his head, to have some control over the situation. The very vulnerability of her position was turning her on, if she was honest with herself. Not only was her pussy open and available to him, completely visible for his enjoyment, but her ass was totally vulnerable as well.
When he put his fingers on her pussy lips and began to massage, she thought she might come, but then to her shock his tongue moved higher!
“Oh no,” she gasped, completely shocked by this new development. Immediately she clenched her cheeks, almost horrified at what he was doing. She’d assumed that Anal Play would mostly just be able sticking things into her ass until it was ready for a cock, and that hopefully the precursors wouldn’t hurt and would make the final act less painful as well. It had never occurred to her that someone would want to put his mouth there!
But Mr. Flood’s hands pulled her cheeks apart, and she moaned at the loss of his fingers on her pussy. Her face felt like it was burning from embarrassment as his tongue flicked over her asshole, tickling the nerves there, and to her shame she felt her hips moving back against him the same way they had when he’d been licking her pussy. It felt good, she couldn’t deny that, but she still felt like she was doing something so completely wrong by allowing him access to that most private of places, letting his eyes and mouth feast upon her forbidden whole.
But then his fingers were back on her pussy and his tongue was licking her hole, and the combination amazing. Her hips started moving again and her muscles relaxed as she accepted this new debasement, unable to resist the pleasure that he was offering. As her muscles relaxed his tongue began to force its way into her hole, making her clench all over again at the new and unexpected invasion. Then two fingers began to press into her pussy and her body quivered, releasing his tongue, which he stiffened and began pressing into her again and again.
It was the strangest sensation, although from his enthusiasm he seemed to relish the taste. Then his mouth pulled away and she moaned again, protesting the loss, and then quieted as she blushed. Had she already developed a taste for such forbidden fruit?
Justin was very pleased with how quickly Jessica was advancing. She’d obviously been shocked by having his tongue placed on her backside but the shock didn’t last for very long and she was so responsive that he felt she was ready for the next part of the lesson. Pulling the lube out of his pocket, he slathered some on his pinky and then pressed it to her damp hole. For an anxious virgin his saliva wasn’t going to be enough, although perhaps one day she’d enjoy the slight burn of being penetrated with minimal lubrication, for now he wanted to make this as easy on her as possible.
He heard the slight sound of protest she made as the head of his pinky slipped into her backside. It was obvious that he wasn’t hurting her, but she obviously had some hang ups about anal sex, and the new sensation was probably not quite comfortable yet. But she’d get used to it.
That tight asshole flexed and crinkled around his pinky as he started massaging her pussy again. After a few moments her body relaxed, the initial bodily protest subsiding, especially under the expert assault of titillation he was pouring onto her eager pink pussy. As her body relaxed he started pressing a little more of his pinky in, and then pulling it out, and pressing it back in. Her body spasmed and adjusted, although he was sure that her protests were more mental; she was unused to this kind of penetration, but he knew he was being gentle enough and that his finger was small enough that while it might not be entirely comfortable, she wasn’t experiencing any pain.
“Oh dear,” Jessica pressed her face into the soft leather, her hands grasping the sides of the triangle. The finger in her backside was causing the most unusual fluttering feeling in her stomach. She couldn’t decide if she liked it or not, although her pussy was very pleased with the expert manipulation of his fingers. What made her most uncomfortable about the entire situation was that, not only did his finger not hurt, but it was starting to feel rather good to have it sliding in and out of her. Her body had almost immediately adjusted to the small intruder, and now as it slid slickly in and out, all the way down to the knuckles on his hand, she could feel her hips automatically humping back at him.
Moaning softly into the leather, she felt humiliated. She shouldn’t be enjoying this should she? This school was the first place that she’d heard girls talking about anal with pleasure, and it had disarmed her. Surprised her. But she’d figured that perhaps they were either all bluster and making it up, or that they’d liked the pain. Hadn’t she seen how much Charity liked pain with her pleasure? Jessica liked a little pain too, but the amount of pain that having her ex shove his dick into her backside had caused had been way beyond her sexy thresh hold.
Even when he’d asked her for anal, it had been in the way that someone asks for something they know they shouldn’t have. He’d wanted it because people aren’t supposed to do it, because it was a big no-no in their world of prim and proper. On the other hand, she’d come to a school for sex, so she couldn’t be that prim and proper, could she? The fact that she was now face forward on a leather prop, her ass high in the air while a finger dipped in and out of it as she moaned her approval definitely wasn’t prim and proper.
When he pulled his finger out, she almost cried out with the loss. Then he was back, and it was thicker. Her breath caught in her throat as two fingers began to push their way in, stretching her tight little hole wider. It was not quite comfortable, but it felt good, it felt right. Yes, yes this hole should be plugged, filled, used. Fingers pushed into her vagina and she started thinking about the menage trois class demonstration, the idea of having two men inside her body at once. When she’d thought about it before it had been with the idea of one in her mouth, one in her pussy, their hands all over her. Now, Mr. Flood’s fingers were mimicking a much more raw, much more dangerous sex act.
Her body tightened down with excitement, and she took her hands from the edges of the triangle and lifted her upper body a little so that she could put them on her breasts, pinching her nipples.
“That’s it,” Mr. Flood’s deep voice washed over her, his fingers pressing in and out of her pussy and ass in an unmistakable rhythm. Then he plunged deep and twisted them back and forth, making Jessica squeal with the thrilling sensation of having her insides stirred. Her asshole felt slick, moist, ready. Having fingers in both of her holes was dirty, heavenly, she felt a sensation of fullness throughout her entire lower body that she’d never experienced before. “You like my fingers in your ass, don’t you?”
Jessica nodded, gasping, “Yes.”
The admission shamed and freed her, even as his dirty words made her shiver with a thrill of defilement. Yes, she liked it, those digits digging their way into her secret places, wringing new sensations from her, plundering her body, opening it to a new world of raptures. For the first time in her life, the idea of having a man ease his hard dick into her tight ass turned her on. It would stretch her so much wider than these fingers, bury so much deeper, and the idea made her hot, hot, hot.
“Oh God,” this thumb pressed against her clit as he spread his fingers inside of her ass. And then she let out a wordless wail of ecstasy as the sensations splashed over her, her holes filled, she could feel her orgasm through her entire lower body, her ass and pussy both convulsing around the fingers that were filling them, the fingers that kept pumping mercilessly as her orgasm grew and grew.
Her hands squeezed her breasts automatically, her hips humping up and down as he relentlessly massaged her clit, shoved his fingers back and forth inside of her body. She buried her face into the leather and practically screamed her pleasure, the intense sensations wrapping around her body, lifting her high and then letting her fall into an exquisite agony of gratification.
Finally her hips fell against the rounded leather for the last time, and he gently massaged her pussy, removing his fingers from it but still keeping the ones in her ass. Jessica moaned as he continued to pump his fingers back and forth in her ass, his other hand wringing the last drops of pleasure from her orgasm. Her pussy felt swollen and sensitive, her hips jerked with each brush of her clit. Every nerve along her skin hummed with sensation. Releasing her breasts from the tight grip her hands had on them, she let her arms rest on either side of her face, submissively accepting whatever Mr. Flood wanted to do to her.
Author’s note: This is based on a dream I had when I was 16, but decided on a boarding school where the characters in this are 18 (my age) so it isn’t underage. Just to clear that up. And this didn’t actually happen, but it is based on a person (not their real name). I hope you enjoy this and don’t get bored because of this note…
Sitting in the back of English, I watched the balding teacher complain about the behaviour of our class. We were supposed to be learning about Of Mice And Men, but only 6 out of 30 people in our class did the homework, I wasn’t one of them. I heard a sexy chuckle from next to me. Kevin Malcolm. He was black with a bulky body, so built that his uniform always looked tight-fitting. He bullied me for being bisexual, but that still didn’t stop me from wanting to have sex with him. I would be so excited when he got up, so I could watch his perfect butt as he walked away, and he never wore his blazer which meant I got to see how toned he was through his shirt, and even see his nipples through the fabric. I didn’t love him, I hated him, but I just wanted to have sex with him ever since I moved to this school. I desperately wanted his dick, but never had the courage to do anything about it.
Being in an all-boys boarding school, Kevin didn’t get to hook up with girls very often. This was probably why he was so nasty to others, because he didn’t get to ‘relieve stress’. I watched him in class, we were sat together in the seating plan on a two-person table which was right at the back. Kevin always sat on my right, against the wall. I watched him with anticipation as I felt an erection growing in my trousers, I just wanted to have sex with him so badly. I was watching him not pay attention to the teacher, until I noticed his hand move to his crotch and start to rub himself. I heard Kevin slowly unzip his trousers, and looked down to see his hand inside his trousers. My heart was beating out of my chest at this point, and before I could stop myself I put my hand on his muscular leg. He turned to me in shock, but smirked slightly and let me move my hand to his crotch. I undid the clip of his trousers, and pulled down his plaid boxer-shorts. His manhood was beautiful; it was a normal length of 6 inches, but really thick. I looked at the amazing black dick and wrapped my hand around the shaft. Kevin let out a small moan and I started to pump my hand up and down his dick. I felt it grow in my hand, getting harder and thicker. I started to jerk him off a lot quicker, and felt Kevin thrust his hips towards my hand. I was panicking at this point, I had no idea what I was doing. I wanted to taste him, so I ‘dropped’ my pen and bent down to get it, and took his balls in my mouth. I then dragged my tongue up the shaft of his cock. When I got back up I started to milk him again, but did it quicker, and I felt Kevin tremble as he came. His cum sprayed underneath the desk and seeped down my hand. When he was well and truly milked, I pulled my hand away and licked the cum off my fingers.
Kevin stayed silent for the rest of class, and when it was over he stormed out of the room. It was the last lesson of the day, and everyone had to go about their daily activities until everyone had to go to bed. I would stay in my room to read my books, and I get to do this alone because the other person in my dorm is addicted to smoking, so he is always outside. I was reading a really good book, it was about a serial killer, and I got to the part where the main character was getting more developed when the door flew open, and I turned to see Kevin shutting it. He pushed me to the wall as I got up, and forced me to the floor.
“You fuckin’ fag.” He muttered as he undid his trousers, and threw them along with his boxers down to his ankles. I stared at his throbbing manhood as he grabbed me by the hair and forced his member down my throat. I gagged at first, but quickly relaxed into it. I wrapped my tongue around his erection and started to suck hard. Kevin was thrusting into my mouth, and my hands slowly guided up his legs, and rested on his big ass. As I cleaned his dick with my tongue, I squeezed his soft butt. He felt so good. I kept sucking his erection for a while, until I felt him tremble again, and I felt the warm, salty liquid drain down my throat. I swallowed every drop, mainly because my mouth was full. Kevin pulled his flaccid cock out of my mouth, and pulled up his trousers.
“You’re my bitch now. Don’t forget that!” He glared at me, and left the dorm. I stayed on the floor, and wiped the warm liquid running down my mouth.
Kevin would make me give him head almost every day for the next few weeks, but still treat me like shit all of the time. Every English lesson he would get me to jerk him off, and started to get more confident with it. One lesson he got me to give him head, and nobody noticed. One night he made me do something totally different from what he usually wanted. The person I shared a dorm with was asleep, and I was just about to go to bed, when Kevin opened the door. He looked at the other guy and gestured me to go somewhere with him. I followed him to the gym, where he opened the equipment-room and sat on the pile of mats. He threw off his shirt, and then his trousers.
“I want you to suck my asshole.” He said bluntly, but I could tell he was very unsure whether he wanted me to do it. Afraid of Kevin getting mad, I climbed onto the pile of mats as Kevin positioned himself on his elbows and knees. I hesitantly held onto his big and soft cheeks, I looked at his asshole. It looked clean, and smoothly hairless unlike mine. I placed my mouth between his cheeks, then licked the tender hole. Kevin shivered, and I poked my tongue in his hole. I managed to stretch my tongue inside, and swirled it around.
“Ugh… Just like that!” He panted, I felt him sweating slightly. I kept doing it, and Kevin began sweating even more. I kissed and nibbled at his sensitive asshole. He groaned even more.
“Jack me off as well!” He demanded, his voice quivered in pleasure. I took hold of his rock-hard manhood and started to pull the skin back and forth, the friction causing Kevin to orgasm very quickly. His cum spread across the blue mat, and as he let out a sexy groan I let go of his dick and pulled my mouth away from his asshole. He quickly pulled on his clothes, then glared at me like he always did.
“Now fuck off.” He ordered, and I rushed out of the gym. I never even said a word to him when he did this, I would only follow his orders like his little bitch.
I started to hate Kevin even more, but I enjoyed being his fuck-buddy. He inspired me to start trying to work on my own body, so I would go to the gym about 4 days a week. After a few months I was looking pretty good; my muscles were more defined I felt more attractive because of it. My own uniform was becoming tighter. Kevin was now getting me to perform analingus on him at least twice a week. In English class he would still get me to jerk him off, and sometimes make me perform oral sex on him. Kevin was being a lot kinder, because he would let my hands wander around his perfect body. One day after physical education, I was in the showers. Nobody else was in the showers because I always took longer than everyone else. The reason I got away with this was mainly because it was at the end of the school-day, so it was everyone’s free-time. I was letting the hot water cascade down my body, and just stood there contemplating life. I suddenly felt rough hands grab my shoulders and spin me around. Kevin Malcolm was holding me, totally naked. His throbbing erection was digging into my side, turning me on in an instant.
“Get on the floor, hands and knees.” He demanded, his sexy yet scary voice forced me to the ground. I could feel anxiety set in as I wondered what he was going to do. One hand grabbed my ass, and I felt something brush against my inexperienced asshole. I struggled slightly, and groaned in agony as I felt Kevin push his entire 6 inches into me. Kevin let out a sigh of relief, and pulled out, then in again. Kevin’s hips smacked against my butt as he fucked me. It started to feel good, despite the burning pain in my rectum. Kevin’s hands started to move up my back, and around to the front of my torso. They rubbed down my stomach, and grabbed my erection. Kevin started to jerk me off as he screwed my ass. Kevin let out the familiar groan after about 10 minutes, and spurted his semen inside me. I came in his hand, the first time I was able to when doing something sexual with Kevin. It felt so good, his warm hand squeezing my dick until it was dry. Kevin pulled out, and casually walked out of the showers as if nothing had happened. I stayed on the floor, recalling what had happened. For some reason I felt as though Kevin was a really sensitive guy. His hands were so gentle on me, and it felt like such an intimate moment where I didn’t hate him. Maybe Kevin wasn’t so bad after all. Maybe he was… A nice person. I couldn’t get it out of my head, he was totally focused on me during that, which made me think he was gay.
I decided to confront Kevin about this, so I decided to visit his dorm a few nights later. He was lucky enough to not have a room-mate, so he wouldn’t have to share a room. I pushed open the door, seeing Kevin’s room. Posters of hot pop stars were stuck to the white-washed walls. Clothes were strewn across the floor. And Kevin was laying on his messy bed, listening to music through white headphones. He looked up at me with a glare, but I could sense a kind look in his eyes. He stood up off his bed and threw his iPod onto his bed.
“What do you want?” He asked scornfully. I took a deep breath and laid it all out.
“I think you’re gay.” I told him seriously, and I was met with an evil look.
“No I’m not!” He demanded, grabbing me by the throat and pushing me against the wall.
“But… In the showers…” I garbled, but the grip around my throat tightened.
“I told you not to talk about it!” He snarled.
“You like me, I can tell.” I stated, readying myself for a punch. Instead I was met by Kevin smashing his full lips against mine. He opened his mouth and our tongues intertwined. Making out after a couple of minutes, I wrapped my arms around his neck, and ran my hand through his short, fuzzy hair. Kevin pulled me away from the wall, and lightly pushed us both onto his bed. Still kissing, Kevin pulled off his bed-shirt, just unbuttoning the shirt and it was off. I started on unbutton my own, and pulled my arms out of the sleeves. Kevin started to kiss down my rugged chin, gentle kisses down my body, until he reached the elastic of my boxer-shorts. Kevin pulled my boxers down my legs, and pulled his own down. Kevin pulled my legs over his broad shoulders, and licked my sensitive butt-hole. I shuddered at the immense pleasure, and he started to penetrate the hole with his tongue. I gripped the bedsheets, and almost yelled out in bliss when he pushed his fingers in one by one. The feeling was so good, and I could have came right then. Kevin move back to my face, and started to kiss me more. Feeling the head of his erection push against the opening of my ass, the feeling wasn’t as bad this time because of Kevin’s spit acting as lubrication. Feeling Kevin push further in, and grabbed his muscular arms, and started to massage down his back. Kevin was pushing into me, and after 10 minutes, I came in a pleasurable explosion of fluid and moans. Kevin reached his orgasm a minute later, and we collapsed next to each other. Kevin reached my face for one last kiss, I put on my clothes and left afterwards. Now I knew that Kevin was mine.
This is my first story, so please be gentle but honest in your criticism. Please also assume that all characters are fictional and above the age of 18. Any likenesses to real people are purely coincidental. I’m sorry this story is so long and boring, I’m just trying to give context and set up characters.
I gazed out the window and thought…nothing. I thought nothing. This class did more than just bore and confuse me, it made me will my brain to shut off so to not listen to my teacher’s boring lesson about logarithms. I didn’t understand but what did I care? I was a second-semester senior, already accepted to my dream university. I needed this class to graduate, but that didn’t mean I had to make an A. I was fine taking a C or even a D.
“The answer, Marie. What was your answer to number 7 on the homework?”
“Oh, uh, I didn’t do it, sir.”
“Fine. See me after class.”
Whatever. It’s not like he can call my parents, just a week after my 18th birthday and I’ve already exercised that freedom numerous times. I mentally scoffed and crossed my arms in apathy. And Mr. Jones was off, torturing some poor scrawny guy, who answered promptly about something to do with a change-of-base theorem. The rest of class was uneventful. Something about some guy named Euler taking the “natural” log of something. I was ready to leave, mentally challenging anyone to get in my way. I was going to get out of there with a clean getaway and no after class reprimand. Before I could even get up, Mr. Jones called me to his desk, perhaps sensing my evasion. I put my purse down with a sigh and slowly treaded to desk while the other students filed out with expressions of sympathy and encouragement. I shrugged back at them.
“That’s twice today you haven’t been listening!”
“I was listening!”
“Oh, really? What was the last thing I just said?”
“You, er, you were saying how you just wanted to compliment on my new haircut?” I decided that ditzy and flirty was the best path.
“No. I was saying that I don’t tolerate slackers in my class, Miss Adams. Look, I know you don’t care, but you could have pretended. I especially don’t understand why you would daydream in a class in which you’re failing.”
“Mr. Jones, surely I’m not failing. I must have turned in something. Wasn’t there a homework I turned in last week?”
“Yes, but that was late and counted as half credit. Even with exams, you won’t be able to raise your grade to passing.” He replied cooly.
“No. no. no. no.” I was playing my about-to-cry card, but it wasn’t working.
“Of course, we could arrange a deal, one that would benefit both of us.”
“Of course! What would you like me to do? I could clean your office or grade papers—”
“None of that will be necessary, Miss Adams.” He slide his fingers up in down a pen, making me hang onto his every last word. “I have another class waiting at the door. I don’t have much time to explain. The deal is I pass you and you let me fuck you however I please, whenever I please until graduation. You tell no one. If you tell, I’ll simply deny it and fail you. If you refuse, I’ll fail you. Decide now.”
My mind wasn’t racing. My heart wasn’t thumping out of my chest. I knew what I had to do. And I wasn’t the type of girl that let anything—or anyone— stand in my way of success. I really should have seen this coming. I was fit, albeit short, captain of the cheer team, a swimmer, and a big enough flirt that I should have been surprised that this was the only time I’d been propositioned like this. “Ok.”
“Good. Get under the desk.”
“Now. You start now. My next class can do group work so I can sit here.”
The bell rung and I knew his students would come in soon. I got under the desk. It was one of those large wooden ones that belonged in the office of a CEO. It had an empty space for his legs or, in this case, me. The students entered. Mr. Jones rose and got a sycophantic junior to handout busywork to the class. Soon they were in groups and talking more loudly than Mr. Jones would have normally allowed. He sat down and some rustling noises told me he got papers from his attaché to grade. I was confused as to what my current task was, but ambitious in knowing that I must please him to graduate.
“Marie. Don’t reply. Just unzip my pants, take out my dick and suck.” Mr. Jones whispered my instructions quietly but emphatically.
What was I to do? For all my bluffing and my choice of clothing, I was still a virgin. I don’t mean just didn’t ever fuck. I mean never been kissed and only learned enough (usually through porn) to make myself seem like an expert. I had been asked out, but never accepted. I just didn’t like high school guys. They were just boys. But, Mr. Jones wasn’t the kind of man to be kept waiting and I wasn’t the kind of girl to make him. I did as I was told. His dick, man, it was about as long and hard as I’d seen in porn but twice as thick, and everything about it—and him— seemed domineering and rough. My late nights of playing with myself paid off as I remembered what all the girls did in those videos. I began licking, long slow ones with the flat of my tongue until it was covered and shiny. I began kissing and darting my tongue out between my lips as he grew harder. I was pretty involved in my work until he grabbed my hair and growled, “I said suck, bitch, not fucking make out with it.”
I’d never been addressed that way and I was about to mouth off until I remembered my predicament. That’s not quite true, actually. I was about to mouth off until I realized how wet I got just from those words.
Again, I didn’t really have time to go down that path before remembering Mr. Jones’s impatience. I did like the porn stars and circled my lips just around the head for a while, licking the salty substance that I knew was precum. It wasn’t as bad as my friends said it was, but not as good as porn girls made it out to be. I soon tired of this and began to see just how far I could go down his shaft. I was ¾ the way down when I gagged. I began to pull away but I felt his hand move to the back of my head and force me to keep sucking his dick.
Sucking cock, I learned gets exponentially easier with time. I would use my hand on the parts I couldn’t reach with my mouth. I rotated from just the head, to the balls, to the underside, to deep throating (what I thought then was “deep throating”). I felt his dick twitch, and, every time that happened, he would push me off for a while. During these intervals, through which I assumed he was regaining composure and delaying coming, I flipped up my skirt and began playing with my pussy through my thong. I had never put anything in. I just liked playing with my clit. I soon smelled my pussy juices and he smelled them too.
Luckily, classes were short today due to our weird block schedule and the juniors exited to go to electives in 35 minutes. As soon as that one sycophantic junior girl finished bombarding him with questions and complimenting him on everything— including the way he arranged his pens— he growled at me, “suck harder, slut. Yeah, I smell you getting turned on by this. God, you’re such a slut. You’re sucking your teacher off just to get a passing grade, and you’re enjoying it. I have a couple hours until my next class and I’ll write you a note for the ones you’ve missed. I want to see just how you play with your pussy.
He pulled me up and pushed me to a sitting position on his desk, his body between my open legs. “Go on, show me or get out.” I was more than humiliated. If I weren’t so ambitious towards my life goals, I would have cried. In a break of character, Mr. Jones murmured approvingly, “I like that you’re shaved and this red thong. You’re such a slut. You’re a dirty whore.”
I opened my legs further and went under my thong to play with my clit. I closed my eyes and tried to pretend I was at home, in bed, watching some really bad acting and some really good sex. I was lost in the moment until I heard the unmistakable sound of scissors cutting fabric. I looked down to see him pulling my pieces of thong away. That was my last protection from him seeing directly at what I was doing, but I didn’t care, I was so close.
I blinked down at him. Why why why? I just wanted to come. I was so close. I felt like a petulant child who was so close to that cookie jar. He directed, “close your eyes and don’t open them until I tell you. Continue playing with yourself, if that’s what you call that.” I did as I was told.
I heard rustling and then the unlocking of an iPhone. Then my heart skipped a beat when I heard a series of those fake shutter sounds that the camera app makes when it takes a photo. I opened my eyes in horror. I grabbed for the phone and got slapped across the face. He jumped away. My face and ego were stinging from his slap. By the time he sat down again, I had recovered enough to be angry.
Before I could voice my indignation and contempt. Mr. jones spoke, “Marie, this is my insurance policy, just in case your future wasn’t enough. Refuse me, tell someone, and these will go all over the school and internet. Nod if you understand.
I nodded. “Good, I don’t like my whores to speak. Now you’ve had some independent fun with your pussy, I want you left squirming when you suck me off.” So I did just that. I got on my slut knees and used my slut mouth and began sucking. I wasn’t good enough, apparently, because he grabbed and started fucking my face. Then I learned what deep throating was. He told me to swallow his dick and I did, and it hurt a little, it was mainly just weird and uncomfortable. He came, shooting hot sticky jets in my mouth. I started to spit when he slapped me and told me to swallow.
When he was done, he told me I could leave. On my way out, he said, “I teach a class at 6 tonight the college across the street.” He told me the location and classroom and told me to be there at 5:45, because “you haven’t yet received your punishment for not doing your homework.”
Rachel couldn’t believe it. She had worked hard preparing for this psychology test. She had passed up more than a couple of social engagements just to put in extra time studying and she was certain she knew the material. As mad as she was, she had played it cool when she approached Professor Jackson about the score.
“Excuse me Professor Jackson, I would really like to discuss the test results with you.” she said softly as she approached the big desk as the rest of the students cleared the room.
“What seems to be the problem? I am sure you will tell me how I made a mistake in my grading, you students always do.” he said with bitterness.
“Oh! No sir!” she said feigning shock. “It’s just, well I really thought I knew the material and obviously I do not understand it at all because I cannot understand where I lost points. I was hoping that I could come by and see you tomorrow in your office to go over it. I am sure with a little bit of time with you one on one I will much better understand this stuff and be better prepared for the final.”
He was quite taken aback by this statement causing him to stammer over his response, “Umm…uh….yeah….yes, of course we can meet. I…umm…let me see….yes, I have classes until 3:30 tomorrow. We can meet at 4:00. Does that work for you?”
“Of course it does Professor Jackson. You are doing me a huge favor helping me out, I will do whatever it takes.” she said with a sly smile and then added, “To make the appointment I mean.” she then turned And walked out of the room.
That was all yesterday and Rachel had spent the day planning for her meeting with Professor Jackson, there was no way she was leaving his office without an improved grade. She had noticed the special attention he gave to girls in class when they wore certain outfits and she had strategically selected her outfit for the meeting. It was a pleated skirt that came to just above mid-thigh. She wore a nice form fitting white short sleeve sweater and had on a pair of black heels.
Rachel made certain she timed her arrival correctly, she did not want to be too early or too late and put the professor in a bad mood. She knocked on his office door promptly at 4:00 and heard the voice on the other side say, “Come in.”
As she stepped into his office she noticed he was sitting at his desk busy at work.
“Professor, did I come at a bad time?” she asked in a quiet voice. “I thought you had said today at 4:00, but I may have been mistaken.”
“What?” came his gruff reply and for the first time he looked up. Judging by the sudden change in his expression she was certain she had picked the right outfit. “Oh, I must have gotten caught up in my work and forgotten.”
“I can come back later if you want me to”
“No!” he almost tripped over himself saying it. “I mean it will not take but a couple of minutes to finish up. You can stay and make yourself comfortable.”
“Thanks.” she said and with that she sat down in the seat opposite him cause her skirt to rise a little and then crossed her legs causing it to rise a little more. He was staring intently at her and she just asked, “Don’t you need to finish that?”
“Oh, yes” he replied.
He had been working for only 30seconds when she spoke up. “I love your office! It is so masculine and mature. Normally I am just hanging out in the dorm rooms and all the guys have posters up of naked women and beer.”
“What?” he asked startled. As he looked up at her again.
“Naked women and beer! You know those cheap posters you get on the quad. It is nothing like your office, so elegant, mature and masculine. It really gives the feeling of a man who knows himself and is secure in that. I think it’s very sexy, I bet you really know how to take care of a girl.” she almost immediately buried her face in her hands’ “Oh my god! I can not believe I just said that.” behind her hands her mouth had curled into a devious smile. “I am really sorry I just broke up with my boyfriend and I am afraid I am a bit out of sorts right now.”
“it’s okay,” he said reassuringly, “I will take it as a compliment.”
“What’s that?” Rachel asked as she fixed her sight on an object on the highest shelf to the right of his desk. Truthfully she did not care what it was, it was the positioning she was most interested in. She got up and walked to the shelves stood on her toes and stretched her body out as far as she could making sure to lift her skirt as high as she could in the process. She knew he was looking and her plan was working perfectly.
He got up and was walking to where she was stretching, answering her question. She could tell he was craning his neck trying to get a better view of her ass. Just as he got near she “lost her balance” and fell toward him. As she expected he caught her as she feel against his shoulder. As he lifted her up she was pulled close to him so she could press her body against him. He was a good foot taller than her so even in her heels she looked up into his eyes.
“Are you alright?”
“Thanks to you.” she said as she put her hands on his shoulders and smiled. “If you had not been there I would have ended up on my hands and knees on the floor” as she said this she felt something twitch against her. “Are you alright, professor?”
“I am fine, why do you ask?”
“Well I have been nothing but a distraction since I arrived today. And now it seems I am creating other problems for you.” He looked at her in a confused way. “well it seems your test is not the only thing in this office that is hard.” and with that she moved her hand and began caressing his cock through his trousers. “Maybe I can make it up to you.” she cooed.
Rachel continued to stroke his hard cock through his trousers as she lowered herself in front of him so that the zipper of his trousers was right in front of her. She leaned in and took the zipper with her teeth and began to tug, slowly lowering his zipper all the while caressing and striking him. Once she had gained full access to inside his trousers she slid one hand inside. She looked up at him and her mouth opened and she let out a little gasp as hear hand found his stiff member and realized there were no more layers of clothes between her hand and his hard manhood.
“Professor! Your not wearing anything under here! I never would have guess you go commando.”
She then pulled his hard cock out of the fly she had just opened and began stroking his as she stared at it. There was a little drop of precum leaking from the head of his cock. Rachel leaned in and gently licked the precum. As she pulled away she made sure a string remained to connect her tongue to him all the while she looked him deeply in the eyes. He moaned as she did this. She then reached up and undid the buckle of his belt and quickly followed by undoing the button of his trousers. As she did this she let the trousers fall to his ankles. With his cock now fully free Rachel leaned in and begin to flick her tongue over the tip as she continued to stroke his shaft. With her other hand she began to fondle his balls as she lifted his cock slightly and let her tongue trace down the underside of his shaft. Rachel looked up and saw him looking down at her. With her eyes locked on his she began taking him into her mouth. She heard him moan. She continued to work her mouth up and down his cock as the stroked him with one hand and caressed his balls with the other. She moved further down his shaft with each motion and had his cock well lubricated with a mixture of her saliva and his precum. Rachel pulled away from him just to catch her breath a little and she looked up at him.
“Am I making up for the distraction?” she teased, but he did not answer he simply reached behind her head and pulled her mouth back to his cock. That was all the confirmation Rachel needed and immediately began working him even harder than before. As she pushed further down his cock she felt the tip press against the back of her throat. She held there just a bit longer and withdrew to catch her breath again. She then opened her mouth a little wider and pushed down, this time as she felt his cock press the back of her throat she continued to push. She felt his cock begin to slide down her throat and as it did Rachel reached under her skirt and began to play with her wet pussy. As she rubbed her clit she moved her head up and down sliding his cock in and out of her throat. She heard him moan deeply and he reached behind her head and began to push her further down.
She was so turned on it felt as though her pussy was leaking. She began to rub herself harder and faster. Soon she was so focused on rubbing herself that she had all but stopped working on the professor. Not prepared to let that ruin his time he began to slide his cock in and out of her on his own. He completely withdrew for just a second and Rachel was thankful as she needed a breather from the throat penetration, but the reprieve was short lived. Just as she had caught her breath and began sliding two fingers inside her dripping pussy he pushed his cock back into her mouth. He wasted little time and within a couple of strokes he had his cock back down her throat pushing deeper down.
His pace was picking up as he fucked her throat with both hands behind her her. His assertiveness was getting the better of her and as she rubbed her clit and slide her fingers in and out of her pussy she felt an orgasm wash over her body and let a muffled moan push through her throat. This must have been all the invitation he needed because as she moaned the professor pushed completely into her mouth. She could feel his balls against her lower lip and she loved the feeling. As much as she was enjoying herself she needed more. Rachel pushed back against the professor and managed to withdraw him from her mouth, but before he could object Rachel had spun around and was there in front of him on her hands and knees, skirt thrown up on her back and her bare ass and pussy up in the air.
Rachel looked back over her shoulder at him and said, “I need your cock in my pussy now.”
The professor did not need a second invitation and quickly took a step forward, dropped to one knee and began to line his cock up. He slid the head of it over her lips feeling how wet she was , he slowly slid the tip inside of her and then with one thrust he fully penetrated her, Rachel gasped as she felt him fill her. He begin immediately thrusting in and out of her slamming agains her ass each time. She felt his hands as he held onto her waist, it was not long before he had established his tempo and as sliding in and out of her well lubricated from her juices. She felt as he ran a hand up her back sending chills down her spine. He reached around and began to cup her breast, pinched her nipple. She moaned in ecstasy. As she steadied herself with one hand against his thrusts she reached between her legs and began rubbing her clit. The sensation of his thrusting and pinching coupled with her rubbing sent her over the edge. She shuddered as the orgasm took over her body.
Rachel collapsed forward, barely holding herself on her elbows as her face pressed to the carpet causing her ass to stick further up into the air. The professor took this as an invitation and withdrew his cock from her soaked pussy and she felt the head of his cock press against her ass. Rachel simply moaned as he began to slide into her. It had been so long since she had been fucked in the ass she forgot how much she liked it. As he stretched her she felt the juices begin to flow in her pussy once more. Once he had fully penetrated her he begin to slowly withdraw and then slide back into her. He was not matching the aggression he had before, whether he was being gentle for her sake or his she didn’t know, but she did know it was no good.
She looked back over her showered, ” Fuck me in the ass professor, fuck me hard. Fuck me like you mean it.”
This was all the encouragement he needed and began to thrust harder and faster. Rachel had gone back to rubbing her pussy as she felt his balls slapping against it. She was beginning to moan again. She could feel his cock deep inside her ass pounding and stretching. It was amazing and Rachel did not know how much more she could take, then she felt the professor grab her hair and begin to pull her hair. He pulled her head back and kept thrusting this was the final straw and Rachel begin to buck and felt her ass clinch around his cock.
Just as her orgasm subsided she felt the professor push deep inside of her one more time and she knew he was about to cum.
Immediately Rachel leaned forward withdrawing his cock from her and she spun around to take his cock into her mouth. Rachel had just closed her lips around him when she felt the first stream hit the back of her throat. The professor let out a deep moan, pushed her head further down and continued to pump his load into her. She did her best to keep up, but some began to drip from her mouth. Just as she thought she could not take any more he began to subside. Rachel ran her tongue around his cock and sucked as she withdrew. As his cock popped free from her mouth she wiped her chin with her finger and pushed his cum into her mouth and swallowed. Seeing just a little bit of cum oozing from the tip of his cock she suck the head back in and continued to suck him until he had no more to offer.
Fully spent he collapsed back in the chair and looked down at Rachel. She smiled at him and said, “Now, let’s talk about that test!”
“What?!” he said startled
“The test. The one on the psychology of manipulation. After all professor that is why we are her, remember” she teased. “Let’s see, positive reinforcement and playing the victim got me in here. Knowing your vulnerabilities and playing innocent got you set up for the seduction. I would think I have shown a pretty good grasp of manipulation. Certainly better than that D.”
The professor sat shocked. “Yes, but I can not just change the grade like that.”
“Come on professor, you got what you wanted, surely you can do something for me. Besides, there is one more method of manipulation I haven’t tried.” she looked at him coyly, ” Blackmail!”
“Ok fine. You have demonstrated a working knowledge of the material. I am sure we can work something out.
“Work something out?”
“Well you have demonstrated knowledge of this material, but what about next time? There is one other thing you have shown me today.” he said and a smile spread across his face, “You are much better suited for oral exams.”
Rachel smiled back at the professor. This class was going to be an easy A.