This is a work of fiction, any resemblance to any actual person is entirely coincidental. This is an erotic story and is intended to be read by adults only.
"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.
Justin had thoroughly had enjoyed watching Jessica's slow turn from fear to a sexual awakening of her deepest, darkest desires. Her delightful ass was meant to take a cock, and often. The way it had gripped his fingers, her insides convulsing around them, trying to suck him further into her body, had told him everything he'd needed to know about what a fantastic ride she was going to be.
Now he just enjoyed her complete submission to him. He couldn't wait for her first BDSM class, she was a natural submissive and he was going to thoroughly enjoy showing her all the pleasures that he could give her. But that was for later, at the moment he focused on the pleasant feel of her asshole rippling around him as he continued to play with her body. Her steady breathing with the occasional hitches told him that she was enjoying it to.
"Do you know what a butt plug is, Miss Swift?" he asked, although he was loathe to part his fingers from her body.
"Yes," she responded back, so quiet he almost didn't hear her.
"I'm going to put one in you now. It's going to stretch you just a little more than my fingers are, and it might not be completely comfortable at first - like my finger wasn't, but it won't hurt and it's going to help keep you stretched and flexible. You need to keep it in at least for lunch time, and if you can keep it in for longer that's good but at the very least just until the end of lunch."
"Ok," her voice was rather muffled. She sounded hesitant, anxious, but not scared, and her ass was still relaxed, she wasn't clenching her cheeks at all. That was good.
Reluctantly he pulled his fingers from her grasping body. "Stay right here," he told her, "I'm going to go get the plug."
Every student got a new plug, and they'd be able to take it home with them at the end of school. He chose a medium sized one, she'd be able to handle it and it would help her out more in the end.
Returning, he found that she had done exactly as he told her to, and she was resting with her eyes closed. He caressed her butt cheek gently and her eyes flew open. Grinning down at her reassuringly he showed the plug. Her eyes got a little big but she didn't protest.
Kneeling down behind her again he spread lubricant over the entire length of the plug, and for good measure spread some more on his fingers and pressed them back into her ass. Her hole had closed up a little, but not much, and she moaned and lifted her hips a bit as he pushed his fingers back in. Yes, he thought to himself happily, Jessica was going to be quite the slut for anal sex by the time he was done with her. He let his fingers slide in and out of her accommodating hole before pulled them out entirely and pressed the tip of the plug to her.
Jessica felt completely wrung out, and a little anxious about the size of the plug that Mr. Flood seemed so excited about forcing into her tight crevice, but the thought did turn her on, and she could see that it wasn't quite as big around as a dick, so she should get used to the idea now. She was glad that it wasn't quite as girthy as a dick, now that she knew a little more about anal she wanted to feel a bit of a stretch when he took her cherry. And she was glad that she would have the same teacher for each of these classes this week, after all the wonderful sensations he'd made her feel today, she trusted Mr. Flood to make the popping of her anal cherry very erotic and very pleasurable.
His fingers quested deep inside her again, and despite her exhaustion she felt the stirrings of arousal deep in her belly as he plunged back into her depths. In fact, if he wanted to take her anal cherry right now, she'd probably just lay here and take it... and enjoy it. But after a few thrusts of his fingers he pulled them out and she felt something cool and hard at the entrance to her back door.
Slowly he began to work it in and out, it wasn't as flexible as his fingers but it wasn't so hard it was painful either. She did whimper a little as her ass began to stretch, the widest part of the plug was definitely thicker than his fingers. It felt good and slightly uncomfortable as her tight hole opened much wider than it was accustomed to, like an itch that hurt to scratch but felt satisfying too. He worked the plug back and forth, letting her hole get acquainted with the wider part before sliding back to the narrow, and then back up to the wider, pushing a little bit more of it into her body each time.
Finally her ass closed over the largest part and she let out a little cry as the plug settled snugly into its new home. Her ass clenched around it, and she panted as she tried to get used to the sensation of this hard object inside of her. Mr. Flood massaged her thighs and butt cheeks as she clenched her ass over and over... part of her wanted to expel it, but the widest portion wasn't leaving her body without help right now. After a few minutes of massaging and her ass grappling with the plug, it settled in and she was able to relax.
Mr. Flood helped her to her feet, and the plug moved inside of her. Although her skirt was covering her ass again, she couldn't help the flush that spread across the face as the plug shifted inside her with every movement. There was no forgetting that it was there.
"Thank you very much," she said, moving her weight from foot to foot as the plug twisted and jolted her insides a bit. She was having trouble concentrating.
"My pleasure," he responded. "I look forward to our next class tomorrow."
"Me too... ah," she glanced at the erection that was threatening to split open his pants. "Can I... would you like me to..."
Glancing down he saw the object of her intent. "No Jessica," he smiled his amusement. "Have you taken the Basic Intercourse class yet?" She nodded, not realizing that he'd memorized her class schedule and knew that she had, and had already talked to Mr. Winter about how it had gone. He leaned forward, his face warm against hers as he whispered in her ear. "Remember, anticipation makes consummation all the sweeter."