Naughty Schoolgirl's AssbyBoxlicker101©
Classes had just ended for the day at the local high school, and Principal Benjamin Dixon was feeling horny and a bit out of sorts. He thought about Jennifer Brock, a tall female student with long blonde hair, a beautiful face and a terrific figure, and how he had spanked her with a ruler when she was caught smoking in school. She had suggested corporal punishment rather than expulsion and, since school records showed her to be 18 years old and legally able to make such an agreement, he had been more than happy to accommodate her. The spanking made them both horny, and led to their fucking while she was bent over his desk.
Since that day, Jennifer had returned several times, had admitted to unnamed acts of naughtiness and had been chastised the same way. After the first time, he saw no need to ask about the nature of those transgressions, because he considered them to probably be imaginary anyhow, and just something she made up when she wanted to be spanked and fucked. As his thoughts dwelt on her succulent bare ass and how he loved turning it red with repeated blows of his hand or ruler, he heard a welcome and familiar voice.
"Mr. Dixon, I've been a very naughty girl again, and I need to be punished."
He looked up and saw her standing in the doorway, head bowed and holding some books in front of herself, the very picture of contrition. He knew what she wanted, of course, and very much wanted to give it to her, but he had to stay in character, so it would be more fun for both of them.
"I've told you over and over to stop being naughty, Miss Brock. Now I'm going to have to punish you severely. You get in here and bend over the front of my desk so I can give you the punishment you deserve. Lock the door first."
Jennifer locked the door behind herself and otherwise did as she had been told, her smile a combination of contrition and lewdness in anticipation of the great sexual escapade she would be experiencing in a few minutes. When the sexy blonde leaned over the desk, the principal realized she was not wearing the standard school uniform, but wore the conventional white blouse and a short, extremely tight red skirt, which showed off her curvaceous ass.
"I see you're not wearing the uniform skirt. That's a rule you are breaking, and I suppose there are many others."
"Yes, Mr. Dixon. I have been a very naughty girl, and I deserve to be severely punished. Will you use your belt this time, please? I've been so naughty, I deserve to be punished with your belt, not just a wooden ruler."
"Very well, the belt it shall be." This was a reference to the wide leather belt he kept in his desk drawer for moments such as this one. "I'll have to take off your skirt first, because it's too tight to raise."
"Yes, Mr. Dixon. Please take off my skirt so you can whip me properly, because I am such a very naughty girl."
Eagerly, he unbuttoned and unzipped the non-standard garment and pulled it down to the floor, admiring Jennifer's lovely white thighs and the way her ass filled out the lacy black panties she was wearing. The penitent young woman scuffed off her shoes and raised her feet to allow him to pull the skirt all the way off and hang it over a nearby chair. The white bobby sox quickly followed. Her panties would also have to be removed but, before pulling it down to the floor as he had her skirt, Ben slid his hands inside the elastic waistband to fondle the incredibly smooth, soft skin he would soon be whipping. His cock was so hard in anticipation it felt as if it were about to tear a hole through his pants, so he opened his fly to let it protrude. The freedom provided much more comfort, and he hoped his stiff cock would not be in the way while he was meting out the punishment the blonde hotsy craved.
Once the wispy lingerie had slid down Jennifer's legs and been placed on the chair by her skirt and sox, Ben gazed at the truly lovely bottom he had been day-dreaming about. Her hips flared out beautifully from her waist and curved back in to merge with her legs, while her ass jutted out from her back and arched over and around, in two perfect, creamy-white hemispheres until they merged with Jennifer's thighs. Her ass was one of the most beautiful sights the principal had ever seen, and he tended to fantasize about fondling that pair of alluring cheeks almost as much as he did about whipping them.
When he folded her blouse up onto her back to get it out of the way, the horny principal got quite a shock. The naughty schoolgirl's succulent ass was totally bare and ready to be whipped, but she was wearing something he hadn't seen since peeking in his mother's dresser drawer many years ago. It was a Kotex belt, and he was not aware any of those things were still around.
"Miss Brock, are you in your menses?"
"Yes, Sir. I just started this morning, and I stopped and put on a clean pad just before coming in here. Is there a problem?"
"Well, there might be. You know what we usually do after I have spanked you or whipped you when you have been a naughty girl."
"Mr. Dixon, a few weeks ago, my father painted the front porch on our house. We didn't have any problem going in or out, though, because we just used the back door for a couple of days."
Ben smiled at the extremely erotic scene that comment evoked. "Very well, I shall go in and out the back door today. Are you ready for your punishment?"
"Yes, Mr. Dixon. I have been very naughty and I need a good whipping, along with whatever other terrible and perverted thing you decide to do to me."
He unlocked the personal drawer in his desk and removed the leather belt he kept there for times like this, along with condoms and a bottle of hand lotion, which he hoped would suffice for lubrication. The tool he would use in the young woman's punishment was about forty inches long and quite supple. It would inflict a great deal of pain when he struck her soft skin with it, and leave a bright red mark, which would fade completely in a couple of hours. He had no wish to inflict any injury on any of his students, or even leave any lasting marks, and he very much wanted to get his cock into that truly beautiful ass that was then bare and awaiting him. First, though, he wanted to give those luscious globes a good whipping.
Jennifer was looking forward to it too, maybe even more than the principal was. She had recently experienced anal sex for the first time and had climaxed even more often and more powerfully than she usually did from sex in the more conventional way. She was really eager to get Mr. Dixon's longer and , thicker cock into the same place, especially following the whipping she knew he was going to give her. In particular, she was looking forward to having him press his hairy body against her sore, red skin every time he drove that marvelous stiff organ into her ass.
Everything was ready for something both people would enjoy immensely. The sexy blonde student stood with her feet 18 inches apart, leaning forward with her hands on the desk and offering her ass to the man who would be turning it a bright red with his belt. That man was ready too, standing with his feet apart and the belt buckle clenched in his right hand and some of the leather wrapped around it.
"I have told you over and over to stop being so naughty!" he exclaimed, followed by drawing back his arm and preparing to swing the instrument of punishment forward. "Maybe this will teach you to be a good girl!"
The belt whistled through the air and landed with a loud "smack" on the young woman's right ass cheek, evoking a yelp of pain. The response was genuine; it really did hurt but, within seconds, a look of pure pleasure spread across her face. The second cut of the belt came about thirty seconds later and was on her left ass cheek, leaving a matching red streak, which contrasted beautifully with the creamy shade of the surrounding skin. It elicited another, even louder cry of pain. The principal knew exactly what he was doing - he would wait just long enough after one blow of the belt to allow Jennifer to fully enjoy the combined pleasure and pain before striking her again.
He continued like that, sometimes slashing her with the belt on one of those luscious hemispheres and sometimes on her smooth thigh. Alternating between forehand and backhand and once in a while stepping to the side so he could whip her across both succulent white cheeks at the same time, the lecherous principal turned the equally horny schoolgirl's entire ass and her upper thighs a bright red. None of his blows broke the skin, because he didn't want to inflict any actual injury which might be hard to explain, but all of them sent pain screaming through her body, which immediately evolved into a feeling that was close to ecstasy.
Jennifer was sobbing from the pain and pleasure being inflicted on her, and her body was writhing against the desk as the whipping continued. Besides her other erotic movements, her bright red ass was swiveling from her arousal, driving her feet, one at a time into the carpet. Mr. Dixon didn't stop until his arm was tired and both cheeks and the tops of the naughty student's thighs were almost glowing. He kept the belt handy though, because he thought he might use it some more to enhance their pleasure during the fucking they would be doing momentarily.
He quickly stepped over to the desk, picked up the plastic bottle of hand lotion, unscrewed the top and placed the open neck against the pretty pink hole he was going to lubricate. When Jennifer felt what was happening, she reached back and gingerly placed her hands on her throbbing ass cheeks to spread them to aid in her preparation. The principal squeezed the bottle and squirted some of the contents into her ass, with some of it running down the insides of her thighs. He sluiced that lotion up with his middle finger and carefully inserted the digit into the place he wanted to lubricate. The naughty blonde cooed with delight, even with that small penetration, and spread her cheeks slightly farther.
Carefully, wanting to be thorough and unsure of the lubricant he was using, Ben spread the lotion all around inside Jennifer's ass, as far in as his middle finger could reach. She was squirming in the pleasure from the pain radiating inward from her bright red skin and from the presence of the finger that was moving inside her ass. When the pleasuring digit was withdrawn, there was a slight twinge of disappointment at its leaving, but she knew it would quickly be replaced by something much longer and thicker.
Before that could happen, though, Ben Dixon would have to prepare the longer and thicker thing, first by putting on a condom, followed by more lubrication. When he was through with that, he reached with his left hand between the perfectly-shaped, blazing-red cheeks that made up Jennifer's ass and used a thumb and index finger to pry open her pretty pink rosebud.
"Very well, Miss Brock. I'm going to continue your punishment."
"Yes, Mr. Dixon. I'm really sorry I was so naughty." She bowed her back slightly to raise her hips and ass and give him a better target.
Holding her rosebud open with the same hand and guiding his cock with the other, Ben Dixon moved in close, steered the tip to the center of the cute hole being created and rubbed it to thoroughly spread the lubricant so he could begin the fucking. When everything was ready, he pushed forward and the head of his cock wedged inside, eliciting a sharp gasp from the sexy blonde. Seconds later, he thrust forward again, and almost an inch of the hard shaft burrowed into the tight, greasy ass that was presented to him so well.
From her ass as it was forced open by the thick intruder, the pain/pleasure poured through Jennifer's body, and she knew it would get even better as she was penetrated more deeply. She also knew the hands roughly fondling her painful red ass would give her even more of the same combination. From the whipping she had already gotten, she was highly sexually aroused and hoped to cum at least twice during her further "punishment."
"Oh! Oh! That hurts! That hurts!" she cried, but the principal smiled and kept giving her and himself more and better fun. If it had been really painful and she actually wanted him to stop, they had a code word for that, and Jennifer wasn't using it.
After the third thrust, Ben knew his cock was in her ass deeply enough that he would no longer need to guide it. He checked between the stretched opening and his cock by running his finger between them, looking for loose skin or any other potential problem. Finding none, he wiped the excess lubrication from his hands and placed them on the schoolgirl's soft, red hips, smiling at her sudden gasp of pain as he did so. By pulling back while thrusting forward, he drove two inches of his cock into the tight place that craved it. As he did, he felt Jennifer fucking back to take his cock as deeply into her ass as she could.
Jennifer was leaning over the desk and tightly gripping the opposite side when she felt the hard cylinder surging into her ass, with pleasure radiating from its path, and she rammed her body back to meet it. The big giver of joy burrowed more deeply into her, and she moaned blissfully, as her hips started swiveling, thrusting her feet down into the carpeted floor. Her hands clamped onto the far edge of the desk even more tightly and she continued fucking her ass back to meet more strokes of the cock that felt so good. She was continually rewarded every time she felt the hard shaft driving into her ass.
"Oh, that feels so good! Keep giving it to me. I want your whole cock," she pled with the man behind her.
Ben was happy to hear that, because he had no wish to give the beautiful and sexy student any less than his whole cock. She was very tight, especially for a shaft as thick as his, but the hand lotion was working surprisingly well and he encountered a minimum of friction. With a few more combined thrusts, he felt his pubic hair brushing against the insides of her ass cheeks and knew he had achieved the maximum penetration. Waves of pleasure were rolling over his body from where Jennifer's tight ass was squeezing and releasing his cock from the swiveling of her hips and all her other movements, so he stayed in the same position, immensely enjoying it, for over a minute.
Jennifer also reveled in the short interlude before the serious fucking began, maybe even more than Mr. Dixon did. His cock was by far the biggest thing she had ever had in her ass, much bigger than that of her boy friend, and she was receiving incredible pleasure from it. The opening was stretched much more than the young man had ever done, as was the attached channel. Every time she even twitched, and that happened frequently, powerful currents of joy rocketed through her body from her ass. In addition, the hands massaging her agonized cheeks and the legs pressed against the backs of her thighs that were red and sore, sent even more waves of bliss through her. She could feel her orgasm welling up inside, and she wanted very badly to cum and to cum again, at least twice that day from the combined whipping and fucking.
"Oh, Mr. Dixon, that feels so wonderful," she confided in the man who had just crammed her ass full. "I think I'm going to cum already."
"I'm glad to hear that, Jennifer. I like to see and feel women cumming. It'll be almost as much fun for me as it will for you. Do you want me to play with your clit?"
"Oh, yes, please do that. I cum so much better when somebody does that for me. It's so much better than doing it for myself."
Ben reached around the girl's hip, placed his hand against her Mount of Venus and squeezed his fingers between her and the Kotex. When he reached her clit, which was so swollen it had pushed its way out from under its protective hood, he gently squeezed it between two folds of her inner lips and started to stroke her there. She was wet with her juices, even though most of them had been absorbed by the sanitary pad she wore.
"Ooooo, yes! That feels so good. "But fuck me too."
Slowly, Ben drew his cock most of the way out of Jennifer's ass, paused and thrust it all the way back inside, fondling her clit at the same time. She let out a moan at the exquisite pleasure he was giving her and fucked back to meet him, with his entire shaft ending up buried in her ass again. Once again, he could feel his pubic hair tickling the soft insides of her cheeks. He stayed in that position for over a minute again, while stroking her clit, and reveled in the way the blonde hotsy was writhing against the desk in front of him.
Finally, he drew his cock most of the way out, paused and thrust it back into her ass again, while his hand remained busy on her clit. She moaned aloud as she fucked back to meet him again. The next stroke was the same, as was the one after that, and he continued slowly plunging his cock in and out until Jennifer had some good news for him.
"I'm gonna cum, Mr. Dixon. Keep fucking me. Please."
He was in no hurry himself, but he liked the idea of bringing the teenager to an orgasm, followed by another one. Ben Dixon was aware sex is much more fun for him and everybody else when all the participants cum at least once. He began pounding his cock into Jennifer's ass harder and faster, while her lush body thrashed against the desk in front of him. Once again, he was glad the old school building had been built of sturdy materials and had thick walls that would muffle her sounds of joy.
And the loudest one yet sounded. "Oh, god!" Jennifer cried out joyously as her climax began.
The man who had brought it about kept his cock buried inside her ass, while his fingers continued to caress her clit. Her lower body rocked from side to side while her torso rose and fell while her tremendous climax, better than any she had ever experienced, racked her body. She cried from the exquisite pleasure until the greatest wave of all inundated her body as she reached total orgasm. All Jennifer's muscles clenched, and she cried out ecstatically before relaxing totally against the desk. She would have fallen to the side but for the man who was standing behind her, ready to resume fucking her ass after she had caught her breath and was ready again.
"Oh, Mr. Dixon, that was wonderful." A few seconds later, she added "But I was a terribly naughty girl, and I need to be punished some more."
"Then you shall be punished more," he responded, while drawing his cock back so just the head was still inside the tight ring of muscles. After pausing a few seconds, he drove it all the way back into her ass, until he was pressing his body against her still painfully red skin.
Jennifer moaned loudly, expressing her happiness from the combined extremes of joy and agony and, after the principal drew back and thrust forward again, fucked her ass back to meet his second stroke. This one was even better, both for pain and for pleasure, and she let Mr. Dixon know how great it was.
"Oh, god, that feels good. Keep fucking me like that." Seconds later, Jennifer corrected herself. "I mean, keep punishing me like that. I deserve it because I've been such a bad girl."
"Yes, my dear, I shall keep punishing you until I believe you have been properly chastised." Once again, he slipped the fingers of his left hand between the top of the Kotex and her pussy and started stroking her swollen clit between folds of her inner lips.
The principal was too close to the naughty girl to swing the belt with any kind of effectiveness, but he could still use his hand. He drew his cock most of the way from her ass and started plunging it all the way back in, and this time his long, deep thrust was accompanied by a hard swat to her already sore cheek.
"Oh!" Jennifer cried from the sudden, intense pain. "Oh, yes, please spank me like that because I am so naughty."