Dan prepared for the evening with an air of confidence and arrogance about him. He was nearing the end of his senior year in high school and, as with many of his fellow classmates, he was feeling nearly bulletproof. He was already accepted to college and knew that virtually nothing academically, short of actually failing a class, could have any impact on him.
Oddly, as he seemed to care less and less about classes his grades stayed the same or seemed to almost improve. It was almost as if he had relaxed just enough to not get too nervous for tests or too worried of failure. As the year progressed he also had been getting rowdier and rowdier outside of classes. His fellow senior teammates on the football team and he had started acting up more and more in school. Nothing ever that would get them in serious trouble, but certainly trouble enough that they were becoming pains in the asses of some of the teachers and administrators.
The person they enjoyed bothering the most was Ms. Melissa Hayden. Ms. Hayden was the newly appointed vice-principal of the school. It seemed she loved going out of her way to be a bitch or a bother to some of the students. At times she seemed to unnecessarily come down on a classmate in what looked like nothing more than an effort to try and prove to everyone how tough she could be.
The feelings of Dan and his friends were no doubt amplified by the sexual tension they all felt toward Ms. Hayden. They all unanimously hated her, but there was no denying that she was completely hot. She couldn't have been anything beyond 35 but her soft, wrinkle free skin made her face look much younger. She was taller than many of the boys in school and probably would have been around 6' in bare feet. It was hard to judge her height because Dan had never seen her wearing anything other than tall, spike heeled shoes.
He and his friends suspected she wore the shoes to add to her height advantage over the students, but there was no doubt that the shoes added to her sexy appearance. She always wore very appropriate looking skirts that came down to her knees. They were never too tight, but were just snug enough to show off the perfect swaying of her ass and hips as she strutted down the halls looking for someone to bust.
Her tops were never very revealing, but she tended to wear silk tops that buttoned up the front. The way her top clung to her smallish tits and lean waist never failed to cause a reaction in Dan's cock despite his hatred of her. On many nights Dan stroked his cock thinking about how he would love to get under Ms. Hayden's skirt and fuck her until she begged for him to stop.
A few months earlier a rumor had run wild through school that Ms. Hayden only acquired her job by sleeping with various members of the school board. Dan was sure that it was a rumor as it seemed the story grew and changed every time he heard it. At first the rumor was that she had fucked the head of the school board, but by the time the rumor had grown she had let four of the members of the school board gangbang her until they agreed to give her the job.
Some of his friends had become regulars at Ms. Hayden's office after having been sent there either by another teacher or by the "queen bitch" herself after she spotted them doing something in the halls. There were a couple of guys that had so often been in trouble that she had made them her "assistants" after school as a form of detention. She usually had them emptying garbage cans or collating papers or other mind numbing tasks. Dan knew they only caused trouble so they could be with her after school. It was true they hated her, but the lust of an 18-year-old boy is far stronger than his feelings of like or dislike.
Dan himself had a few run ins with Ms. Hayden. Once, he had tried to sneak out of school one class early only to be caught by her. She had scolded him severely and kept him very late after school doing busy work as a form of punishment, but Dan didn't really mind as he took every opportunity to watch her walk or stare wantonly at her when she wasn't looking.
Now it was a Friday night and there were only two weeks of school left. He drove to school to attend what would be his final high school dance. The truth was that the dances themselves were usually pretty lame, but he and his friends often used them as a meeting point from which to start the night.
He parked his car and noticed that the light was on in Ms. Hayden's office. He wasn't surprised as she seemed to live at the school. She was at every dance and would often be seen on stage censuring the DJ's selections in music or out in the crowd separating couples who she thought were getting too "intimate".
This dance was perhaps even more lame than usual as hardly anyone actually showed up. The beautiful night combined with the end of school being so near apparently had everyone thinking of things other than school dances. Dan was getting ready to join some of his friends and leave when he made his way to the restroom.
He stepped out of the restroom and was immediately greeted by her overly stern voice saying, "Mr. Jenkins. I'd like to see you in my office." He stared at Ms. Hayden, dressed as crisply as if it was 8:30AM rather than 8:30PM on a warm, Friday night. He felt the familiar jump of his cock from his own lust.
"I, um, was just leaving," he offered in response as he tried to turn and leave.
"Now!" she commanded in a tone that made Dan stop and meekly follow her down the hallway toward her office. In the deserted hallway her tall heels made a loud click that echoed off the lockers. He tried to figure out what the hell she was doing and he couldn't help but stare at her ass.
"Sit down," she commanded after they stepped into her office and she shut the door behind them. Dan looked and saw one chair sitting in front of her desk and took a seat. He looked straight ahead at the closed blinds as Ms. Hayden began pacing and lecturing him. "Mr. Jenkins," she started, "I suppose you think I haven't noticed all the crap that you have been pulling lately."
Dan stopped listening to her and merely stared straight ahead as she continued her lecture. It was a couple of minutes later when he became aware of her presence directly behind him. The whole time she had been talking she had stayed either to his side or behind him so he hadn't really been able to look at her.
"Mr. Jenkins," she said leaning over close to his ear, "are you even listening to me?"
"Uh, yes," Dan answered unconvincingly.
"Really?" she replied. "Well then, why don't you tell me what I was just saying?"
"I...um...well...I don't know," Dan sputtered.
"Typical," she shot back. "You boys only know how to think with one thing. If you spent half as much time using your brains as you do worrying about your dicks you'd be brilliant."
Dan jumped and spun around to stare at her. Did she just say dick? His mind briefly fluttered with the various types of trouble he could cause for her because of her saying that.
She remained silent and stared into his eyes with a stern expression. She let him stare at her for a few seconds in silence before she said, "Oh, did that excite you? Did you like hearing me say dick?" She stared at him as if she expected an answer. Dan didn't speak so she repeated, "Did it excite you to hear me say dick?"
Her tone made it clear that he was to answer and he cleared his throat slightly before whispering, "Yes."
"Typical," she repeated before continuing, "turn around and face front, Mr. Jenkins. I didn't say you could look at me." Dan turned around and stared at the closed blinds again unsuccessfully trying to keep his cock from growing hard in his pants.
She remained behind him as she resumed her lecture, "I know how you boys think. I know that all you think about is fucking and getting in girl's pants. You'd be shocked if you knew how much I knew about you all." She paused and let Dan's mind spin as he tried to understand what the hell was happening. "Hell," she continued as she leaned slightly closer to Dan, "I bet you even dream about fucking me. Put your hands behind your back."
Her last two sentences were so shocking and had been spoken so quickly that Dan wasn't initially able to comprehend them and follow her directions. "Put your hands behind your back," she ordered again as he this time meekly followed her instructions.
By now Dan was so confused and excited he could hardly think. Was she coming on to him? Was he in trouble? What the hell was going on?
He jumped at the touch of her hands on his forearms. She nimbly maneuvered his arms behind him and the next thing Dan knew his wrists were locked in some sort of handcuffs behind him. In his shock he briefly struggled against them only to realize that not only were his wrists bound together but that he was also bound to the back of the chair. He heard Ms. Hayden laugh wickedly as he struggled.
The next thing he knew she was tying some sort of cloth around his head and his vision was totally blocked. She let him sit for a few minutes as she seemed to pace slowly around the room. He could only hear the click of her heels on the hard floor above his own excited breathing.
He heard her walk over in front of him and stop and he guessed she was standing directly in front of him. He gasped when he felt her hands at his feet. With the same quickness she had shown on his arms she moved both of his legs and Dan heard two quick clicks as his ankles were now cuffed similar to his wrists. He wriggled briefly but immediately found that his feet where tightly secured to the chair and he was totally trapped.
He heard her stand up and she quietly, but sternly said, "Now I expect you to remain silent. If you call out I will swear that I had no knowledge of this and it will be your word against mine. I will suggest that you and your friends were playing a cruel joke on me and you and your friends will be expelled. None of you will graduate and you will all have to delay college. Do you understand me?"
Dan nodded dumbly and then heard her footsteps move away from him and out of her office. He listened as they moved down the hall becoming softer and softer until he couldn't hear them any longer. In the silence of the office he again struggled to free himself but couldn't.
Dan had no idea how long he was alone in the office but guessed it was nearly 20 minutes before the clicking of her heels let him know she was on her way back to him. She entered the office and didn't say a word before she took hold of the front of his jeans. She deftly unbuttoned and unzipped his pants and, before Dan could really comprehend what had just happened, she pulled his pants and boxers off together in one motion. She rocked Dan from side to side working his pants off until she had them pushed down around the cuffs at his ankles.
Without a word or another touch she turned and left the office. He again listened to her heels clicking down the hall until she was so far away he couldn't hear them any longer. He was vaguely aware that they sounded different this time but figured that was due to his own heightened excitement and anxiousness.
He sat now with his heart pounding in his chest and his cock exposed to anyone who might wander by. What the fuck was happening? What was she doing?
When he heard the voices from outside in the hall he froze in fear. He could hear his friends walking toward the office talking about where he had gone. "Shit, look at this," his friend Mark said, "fucking Ms. Hayden left her door wide open."
Dan gasped in horror and he could feel his heart jump into his throat. That bitch left him like this and then left her door wide open! If his friends caught him like this there would be no living it down.
"We should go in and trash the place," Mark said. Dan knew that Mark often liked to talk big like this and he grew terrified when he heard someone, he guessed it was Mark, start to walk into the office.
"What do you think you are doing?" Ms. Hayden's harsh voice called out from the hallway. Whoever had been walking in froze and immediately turned and retreated to the hall.
Mark then weakly stammered, "I was just, I thought maybe Dan..."
"You thought maybe Dan what?" Ms. Hayden sternly said. "You thought Dan was hanging out in my office. You never, under any circumstances, have the permission to enter my office without my consent. Do you understand me?"
"Yes," Mark meekly answered.
"Good," Ms. Hayden said, "now as far as Mr. Jenkins. I don't know that it is any of your business but I saw him leaving a while ago with another group. Now, get away from my office."
Dan listened to his friends walking away quickly. How could they buy the story that he left with someone else? Hell, there wasn't anyone else there to leave with. Surely they would see his car in the lot and know he was still inside.
Several minutes after they left he heard Ms. Hayden enter the room again. This time she shut the door behind her and said, "Your little friend almost had quite the surprise."
She moved around her desk and Dan could hear some rattling. He heard her punch some buttons on the phone and sat listening to her side of the conversation. "Hi hun...Sorry about this but I'm going to be late...I know...I've just got a project I need to finish...I'll make it up to you...Love you."
Her footsteps moved around her desk and again stopped in front of him. She pulled off his blindfold and tossed it aside as he blinked a few times to get his bearings. When his eyes focused on her again she was sitting on the edge of her desk watching him closely.
He watched her pick up something off the desk and felt his eyes widen in shock at the sight of what she held. It was a fur covered paddle. The paddle itself was like one of the old fashioned ones with the short handle and flat end that teachers used to terrorize kids with in the old days. The thing that made this one different is that it was coated in a light brown fur.
She slipped off the desk and stepped close to him until his bare knee was between her legs. She reached out with the paddle and started rubbing the soft fur up and down his inner thighs slowly. Dan gasped and stared at her still unable to believe or understand what was happening.
The first time the soft fur rubbed against his cock and balls he involuntarily let out a moan. Ms. Hayden smiled wickedly at the sound and continued to tease his cock and balls until he was rock hard. "You know," she said as if she had just been struck by a random, amusing idea, "I bet your friend Mark wouldn't have been too upset to find you here. In fact, maybe I should have let him come in. I bet he would have loved getting on his knees and sucking your cock."
Dan's mouth dropped open in shock and he stared at Ms. Hayden dumbly. "Oh, so you like that idea, do you? I bet you'd love to watch your best friend suck on your hard cock. He'd protest some, but only to make you think he wasn't into it. Once he took that first lick he couldn't get enough. Hell, I bet that would look so hot my pussy would get nice and wet."
From seemingly out of nowhere Dan felt his cum exploding out of his cock as she rubbed the fur up and down his shaft. He stared wildly as his cum surged out and coated the paddle in addition to his own cock and balls. "What the fuck is going on?" Dan thought to himself. Had he really just been aroused by the idea of Mark sucking his cock? No, surely it was only made to feel exciting by his particular situation and by the touch of the fur on him.
Before he could think about it any longer Ms. Hayden said, "That was your free pass. If that happens again before you are instructed there will be hell to pay, do I make myself clear?" As she spoke she firmly whacked the padded against his outer thigh leaving a wet spot from his cum on his red skin as she pulled the paddle away. She made it clear to Dan that she intended to use the paddle if he didn't obey her. For a moment he envisioned himself bent, bare assed, over her knee as she paddled him.
She set the paddle down on her desk and began to untuck her shirt. Slowly, and with a crooked smile on her face, she began to unbutton her top. She pulled her top off and revealed her cream colored bra to Dan's excited, confused stare. The smallish cups had lace accents at their top and he stared wildly at her tits. He gasped in lust as she next reached behind her and opened her bra before tossing it behind her.
Her nipples seemed to immediately grow stiff once exposed to the air and quickly stood out tall and tight on her tits. They were definitely smaller than average given her height but their shape was intoxicating. Dan wished he could reach out and touch them but was quickly reminded of his helpless state. She smiled at his obvious lust and took a few moments to fondle her own tits teasingly. She pinched and rolled her nipples between her fingers until they stood out amazingly far.
She reached up under her skirt and first pulled off her stockings before doing the same to her panties. Dan knew she was now naked with the exception of her skirt and his cock had already started to rise. Ms. Hayden stared at his growing cock, still coated in his own cum, and mused, "Ah, so predicable but so wonderful."
With that she stepped even closer and lifted her skirt as she lowered herself down until she was sitting on his thigh. She was straddling his left thigh and immediately started to grind her hips back and forth rubbing her excited pussy over his leg. Dan groaned when he felt the wetness from her pussy.
She continued to slowly "hump" his leg until his cock was absolutely rock hard and his leg was getting wet from her juices. When she stood she looked at him as if she was deciding what to do next. Suddenly she put her foot on his chest and slowly began to push him backwards until the chair was leaning back on only two legs.
Dan stared at her long legs and excited tits until he felt the chair go past the point of balance and he started to fall over backwards. Fortunately the one carpeted part of her office was behind him. The thick throw rug did help cushion the blow on his head but it still hurt quite a bit as he came crashing down on his back. "What the fuck?" he said as the chair came to rest.
"Don't you swear at me, young man," Ms. Hayden scolded. "If you would prefer I could leave you like this all night. I bet Earl the custodian could have lots of fun with you tomorrow."
She waited to see if he would protest and when he didn't she walked over to him and then straddled his head. He lay looking straight up her skirt but he couldn't see her pussy under its shadow. As she knelt down on top of him she lifted her skirt so that by the time he felt her wet pussy pressing on his face her skirt was up around her waist.
He tried to lick and kiss her pussy but she initially didn't seem very interested in that as she instead began grinding her pussy all over his face. She shifted her hips and gyrated all over until his face was coated with a heavy layer of her juices and Dan was gasping for air.
He had seen pictures of "smothering" on the internet but hadn't ever given much thought to it. Now he knew exactly how the guys in those photos felt as Ms. Hayden pushed her pussy wildly all over his face only letting him gasp for air occasionally. The act was so exciting, so nasty, and so erotic that Dan was wildly excited. Coupled with that was the intense frustration Dan felt at having no control over what was happening. Somehow the frustration only seemed to heighten his arousal.
Finally, Ms. Hayden settled her pussy over Dan's mouth and he eagerly started licking and sucking at her. In truth, Dan had very little clue what to do when sucking a pussy but he was so excited that he simply began to lick and suck at her with a wild abandon. For a while he didn't know if she was enjoying it as she was completely silent but then he suddenly felt her body tense as she pressed down on him very hard.
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.
He rolled over to go to sleep and became aware of a dull throbbing in his ass from the thorough fucking he had received. He had to remain on his side as the long scratches on his back hurt whenever they contacted his sheet. Still, the dull throbbing pain he still felt only reminded him of what had happened. When he finally did fall asleep it was one of the deepest, most serene nights of sleep he could ever remember.
