Vice Principal

Her pussy started to quake around his tongue and she began grinding her hips roughly on his mouth as she moaned a long, lusty sound. She stayed over his face just until she finished cumming and then immediately stood up and looked down at him wickedly.

"Well, Daniel. It seems you are quite the eager student," she said.

She lifted the chair off the ground until he was again in the sitting position and then finally unzipped and removed her skirt exposing herself completely to Dan's gaze. He had never imagined that her body would be this hot even in his fantasies. She clearly worked out regularly as her body was toned and lean with strong looking arms and legs. Despite the fact that she was now naked she still wore the high heeled shoes further adding to her sexy appearance.

She looked down at his hard cock and then moved close to him straddling his legs between hers. For the first time she lightly touched his cock as she held it while she lowered herself down. When she came to rest on his lap she released his cock and he could feel it brushing against her periodically as she sat looking at him.

He tried to lean forward and kiss her but she leaned away until his restraints prevented him from going any farther. For a while she teased him by acting as if she was going to kiss him only to pull her mouth away at the last minute. This was driving Dan crazy and she knew it. She shifted her position and began to similarly tease him with her small, perky tits. She held them just in front of his mouth but whenever he tried to kiss, lick, or initiate any contact with them she pulled away.

He was so preoccupied with her teasing tits that he didn't even realize her slight movements. Before he even realized that she had moved he felt the tip of his cock brushing against her dark pussy hair. He let out a long, deep moan when she lowered herself engulfing his hard cock in her wet pussy.

When he was fully inside her she leaned over and put her mouth right next to his ear. "Remember," she said softly but sternly, "if you finish before I give my permission you will be punished." She stressed the work "will" in a way that was simultaneously exciting and a little scary. As soon as she uttered the last word she slowly began fucking him causing Dan to let out a deep moan.

As Dan was still moaning Ms. Hayden stopped fucking him and gave him a stern look. "I am not kidding young man," she said. "You either control yourself our I will really have my way with you." She grasped his chin and lifted it so he was looking directly into her eyes. His eyes were filled with lust and some confusion, but her eyes were cold, calm, and steely as she looked down at him. "Do you understand me?" she concluded.

"Yes," he whispered.

"Good," she said as she smiled at him wickedly. "Now you be a good boy and do as I say." She resumed her teasingly slow fuck as she lifted her hands up and put them on either side of his face. She ran her hands slowly up and down his cheeks before letting them slide down off his face and onto his shoulders.

Dan let a soft moan escape his lips despite his trying to stay silent. The way her pussy felt around his cock was beyond anything he could ever have dreamed. Her touch was stern but wildly exciting. He felt jolts of excitement surging through him starting at the points where her fingertips dragged over his skin.

She smiled devilishly and let her fingertips move down to his nipples. She circled them a few times and Dan became aware that his own nipples had become stiff. They certainly weren't stiff like the women he had watched in porno movies, but they were definitely tighter than he could ever remember them being before.

Her fingertips slowly flicked the points of his nipples and then her smile grew even wider as she grasped his nipples between her thumbs and index fingers. Dan began to moan but then quickly gasped in shock and pain as Ms. Hayden pinched his nipples roughly. He stared at her with wild eyes as she pinched him tightly and continued her slow fuck.

Dan yelped in pain again as she began pulling and twisting his nipples. Hearing his reaction almost seemed to encourage her and she began fucking him a little faster as she continued pinching and twisting his nipples.

At first Dan couldn't feel anything except the pain of her hands on his nipples. Slowly, however, that sensation dulled a little and he became very aware again of her slick pussy moving on him. As the sensation of their fucking came back into his consciousness he became very aware that it felt even better than before. She had changed her tempo but he knew that wasn't the reason it felt so much better. No, he knew that somehow the pain he felt seemed to amplify the pleasure.

After a short while longer she released his nipples and moved her hands up and over his shoulders until they were resting on his upper back. Dan realized that he might be able to reach her tits like this so he leaned his head forward and tried to reach her nipple. Before he could reach it, however, he became aware of sharp pains on his back.

He immediately forgot about her tits and groaned as he screwed up his face in the wake of this new pain. He looked up at her face but she seemed to be looking over his shoulder at her hands. Her long nails continued to slowly rake across his skin leaving long, red lines in their wake as she scratched him.

Dan again was flooded with the sensation of this new pain but as that subsided he again became aware of the intense pleasure of her pussy around his cock. As with before the shocking mixture of pleasure and pain seemingly intensified the sensation of their fuck.

Ms. Hayden continued raking across his back and Dan stared wildly into her face and at her lean body as it rode up and down on him. Before he even became aware of it, Dan felt his cum start to rise out of his balls. He groaned and struggled to control himself even though he knew it was hopeless.

He let out a loud moan as he started to fill her pussy with cum. Ms. Hayden looked surprised at first as his cum exploded into her pussy and then her expression quickly became stern and harsh. It was amazing to Dan how much different this expression looked on her face now. It was similar to the look he had seen from her dozens of times before when she was really pissed off about something. This time, however, that same expression smoldered with lust and sexuality. Dan stared excitedly into her face as he continued cumming.

When he finished cumming Ms. Hayden sat still for a brief moment and then said, "Are you all finished now, Mr. Jenkins?"

"Yes," Dan answered quietly.

"You didn't wait for my approval, did you? Well," she said as she got up off his lap and stood tall before him, "now I get to have a little fun." She moved around behind the chair and Dan felt her unfasten his wrists from the chair. They were still cuffed together but he was now able to stand up when she took hold of his shoulders and pulled him up. She repeated this with his ankles and left them cuffed together as she released him from the chair.

She roughly twisted him around so he was facing the couch and, before Dan could really get a feel for balancing in his ankle cuffs, she pushed him forward roughly toward the couch. Dan immediately fell to his knees and his chest came crashing down hard on the couch cushions. His instincts told him to try and break the fall but with his wrists and ankles bound there was nothing he could do other than yell, "Fuck!" when he hit the couch.

"Mr. Jenkins!" Ms. Hayden called out sharply. She didn't need to say anything else as it was clear from her tone that she was not pleased with his language. Immediately afterward he felt the sharp crack of her hand hitting his ass with surprising force. He cried out as the stinging and burning on his ass almost seemed to intensify as she pulled her hand away. "Anymore of that and you'll be sorry."

Dan tried to turn around and see what she was doing but he couldn't twist around far enough to see her. Judging from the clicking of her tall heels he guessed she had moved back over to her desk. He heard her open a drawer and then heard her rustling around. He tried to shift his weight so he could turn around even further, but before he could turn his head around she sternly said, "Mr. Jenkins, turn back around. You will turn around when and if I say so."

Dan did as instructed and stared straight ahead at the back of the couch waiting for his punishment. His heart was racing and he could feel the knot in his stomach as he waited for her. He could hear her moving around behind him and eventually he heard her footsteps move close to him and stop directly behind him.

He expected to feel the harsh smacking of the paddle on his ass at any moment. He fully expected that would be his punishment after her earlier teasing of him with the fur lined paddle. Or perhaps she would simply give him a bare handed spanking. His ass was still stinging sharply from her single smack and he wondered what it was going to feel like when she finished with him.

Instead he felt her hands brush against his ass before she reached between his ass cheeks toward his asshole. When her fingertips made contact with his asshole he immediately noticed the feeling of something cold and slick on his tight hole. Her fingers worked up and down over his asshole and Dan's mind raced with what was happening.

Her fingers moved away from his asshole and he immediately felt her move closely behind him. It was like she was getting ready to fuck him doggie style and then Dan realized that might be exactly what she was intending. He gasped in shock at the thought.

The next thing Dan knew he felt something else pressing against his tight asshole. He was about to open his mouth to ask her something, anything, but before he could say anything she pressed whatever it was firmly against his ass.

Dan felt his virgin asshole fight the intrusion for a few moments before Ms. Hayden increased the pressure and finally pushed the tip past his tight ring. Dan cried out in surprise and discomfort as Ms. Hayden continued her slow but steady penetration until she drove the full length of whatever she had into him. He could feel her thighs pressing tightly against the back of his legs after she finished filling his asshole. Dan had no idea what she had just shoved up his ass but it felt like he was about to be split in two.

After the initial penetration, the sensation wasn't quite painful but it certainly was uncomfortable as his ass was being stretched beyond any limits it had previously known. Just when it seemed like she would pause so he could adjust to the sensation she pulled nearly all the way out of him and then started to fuck his ass at a firm, steady pace.

"Ohhh God!" Dan gasped as the discomfort became more and more like pain again. He pushed his face into the couch and was overwhelmed by the sensation of her fucking his asshole. It seemed like his gasping and squirming only egged her on and she continued fucking him even a bit harder.

Ms. Hayden let her fingers drag over his lower back and ass as she continued to fuck him with the strap on dildo. She fucked him long and hard not really too concerned about his comfort or pleasure. She knew that he was young and would quickly adjust so she focused on the amazing feeling of control and power she felt as she reamed his virgin asshole.

It took a long while for Dan to get even remotely comfortable with his new situation. He gasped and groaned in discomfort over and over as she continued vigorously fucking his ass. It was only after what felt like a near eternity that he began to get adjusted to the feeling. Oddly, as the discomfort went away he realized that he found the penetration enjoyable.

He had never even thought of his ass as anything erotic before and never guessed it could be exciting. Slowly, his moans became less and less out of discomfort and quickly grew more lustful and excited. Ms. Hayden seemed to sense the shift also as she asked, "So, Daniel, do you like this?"

"Ugh, yes," Dan gasped in between her solid thrusts.

She didn't say anything but began to fuck him even faster and harder. Dan groaned and then gasped in shock when he felt her hand coming down roughly on his ass. She continued spanking him with her bare hand as she wildly fucked his asshole. Again, the mixture of the stinging pain on his ass with the oddly satisfying pleasure of whatever she had shoved up his ass was amazing.

After a few minutes of this Dan again felt the painful raking of her nails across his back. This time she slowly drew her nails over his lower back and ass. Dan cried out as she raked her nails over him. She continued alternating between smacking his ass and scratching him with her long nails for a while as she continued to thoroughly fuck his ass.

"Ohh," Ms. Hayden moaned in what sounded like pleasure, "Mr. Jenkins I could keep fucking your sweet ass all night. Would you like that Daniel?"

"Yes," he answered excitedly.

Time blurred for Dan from that point on. He had no idea how long she continued to fuck him, but he did know that she had to stop two times to reapply the lubricant. By the time she got done fucking him it felt like it might have been hours later. His asshole had now become completely adjusted to the situation and he eagerly and excitedly was able to relax and receive her fucking with growing pleasure.

Once he had time to adjust he couldn't believe how much he started to enjoy being fucked like this. The feeling of being completely controlled by her and being at her mercy further stoked his desire. She again started spanking him as they fucked and didn't stop until she was pumping his ass roughly and his ass was bright red and stinging him in pain.

"Just think Mr. Jenkins," she said wickedly. "If your friend Mark had decided to join us perhaps he could take a turn fucking you. I bet he'd love shoving that big cock of his right up your tight asshole. I bet once he got a feel of it he wouldn't stop until you were begging for mercy."

She pulled out of him so quickly that it took him a few moments to realize it had happened. He felt her hands on his shoulders before she pulled him quickly off the couch and dropped him on his back on the floor. He lay there and gazed up at his vice-principal as she stared back down at him. From the way his ass felt he expected to see her holding something huge, but instead he saw her wearing a strap on dildo. He stared up at her wildly and couldn't believe how hot she looked wearing the strap on. What surprised him was how small the dildo was. It was actually quite thin and probably no more than four inches long.

"You like that, Mr. Jenkins?" she asked glancing down at her "cock". He didn't say anything so she asked him again in a much harsher tone.

"Yes," he answered.

"Hmm, maybe you'd enjoy the real thing," she teased, "do you think you'd like that?"

"I, um, no," he said. It was clear from the disappointed and pissed off look on her face that wasn't the answer she wanted. Before she had the chance to punish him he added, "I don't know."

She dropped to her knees and then brought herself down until she was sitting on his chest. The small dildo was only a few inches from his face and he could smell the strong scent of his own asshole all over it. For a moment he feared she was going to make him suck it but instead she held still and continued to tease him. "Yes, I bet you'd like that Daniel," she began in a sultry voice. "I bet you'd like to have a real cock this close to your face so you could suck it. I bet you'd suck it like a pro. Mark would love having your mouth on him and you'd keep on sucking and licking until he shot his cum in your mouth." She paused and looked down at him. "Would you like that?"

He still didn't think so but there was something about her vivid description and the look in her face that somehow made the thing sound appealing in the heat of the moment. "Yes," he quietly whispered causing her to break into a wide smile.

"Yes," she hissed, "I bet you'd like to have him fuck your ass too, wouldn't you? You fucking little slut. I bet he'd love fucking that tight ass of yours until he filled you with his cum." She continued talking to him like this until it was clear that she was doing it as much to drive herself wild as to excite him.

When she had clearly driven herself into a frenzy she moved forward and again brought her pussy down roughly over his mouth. She was again smothering Dan and he eagerly began sucking and licking at her amazingly wet pussy. She started grinding her pussy all over his face roughly and it only took a few more minutes of this before she groaned loudly and started an intense orgasm.

She stayed over his face for a few minutes just enjoying the feeling of him squirming under her and the feeling of his mouth at her pussy. When she finally stood she took off the strap on dildo and tossed it aside. She looked down at Dan's naked body and just let her eyes move all over his helpless form. Her gaze finally stopped at his cock. Through the excitement of the fuck and then of sucking her pussy his cock had regained nearly all of its size and he lay yearning for relief.

"I guess you've been a good boy," she mused. "I think I'll reward you." Dan groaned at the visions of her fucking him or sucking his cock that danced through his head. Instead she knelt next to him and took his cock in her hand. She began to stroke him with a tempo that soon had him going wild. She easily kept him in control for a while longer and only seemed to let him lose control when she was ready for it. She cupped his balls with one hand and pumped his cock rapidly with the other.

It only took a few strokes like that before Dan cried out and started to cum. His cum flew all over his stomach and only when he was nearly done did some trickle out and run down onto her hand. When he was done cumming she lifted her hand to his mouth and began rubbing his cum on his lips.

"Taste it," she ordered. "Eat the cum." He opened his mouth tentatively and she shoved her fingers inside leaving all the cum that was on her hand inside his mouth. He swallowed it quickly as she looked down at him intently. "There now," she said, "that wasn't so bad was it? Trust me, the first time is always the hardest. The next time will be much easier."

She then immediately began to undo the cuffs on his wrists and ankles. When he was free again he immediately reached for his stomach as if to wipe off his cum. "No," she ordered, "leave it." He looked at her for a moment as if expecting something but she dismissed him by saying, "Now, get dressed. I think you know the way out."

She walked behind her desk and sat down in her oversized chair watching him get dressed. Before he left he opened his mouth to say something but couldn't think of what to say. Instead he simply turned to leave as Ms. Hayden said, "Have a good night Daniel. By the way, if you're thinking of telling anyone about this I would advise you to think twice. Anything you say will be your word against mine and I think we both know who would win that one. The damage your false allegations would do would severely hurt your admission to college, trust me. I would see to that."

He left in a daze and found a note from his friends on his car. He thought about calling them and trying to hook up with them but then he felt the wetness from his cum on his stomach and decided to call it a night. Instead he went straight home, stripped naked, and crawled into bed.

He could still smell her pussy on his face and could still taste the remains of her in his mouth. He ran his fingers lightly through the wet spots on his stomach and then absent mindedly brought them to his lips to taste them. The taste wasn't nearly as strong as it had been earlier but it still sent chills down his spine as it brought back the memory of her sexy body.