English Literature...Oh My!

By: zebo85

Page 1, His favorite teacher keeps him after school; is he in trouble......

Once again, Jim was lost in thought.  In his last semester of high school, his thoughts were obviously about girls; actually women would be more appropriate.  He was in his English Lit class and Mrs. Sherman was looking even more lovely than usual.  All of his friends thought he was weird for thinking she was good looking as she was well, mostly ordinary.  She did little to change that description as she wore mostly long skirts and sweaters that covered her body, wore very little makeup and her hair was usually pulled back in a pony tail.    However, Jim saw something more.  He saw how her eyes twinkled when she smiled, how when she moved just right, the loose fitting sweaters displayed the sumptuous breasts underneath, how her light perfume made his cock lurch and then there was her lingerie.  On more than one occasion, he had spied a flash of her lacy slip and once he’d gotten a quick peek down her sweater when she bent over in front of him and saw a sexy purple bra.  She’d seemed to have noticed his eyes and she had smiled at him in a way that made his cock twitch.

Jim had given up trying to stop his obvious fetish for lingerie.  Ever since the time he was 15 and accidentally seen his sister’s friends in their silky night clothes at a sleep over, he’d been hooked.  The second time they were staying over, what he saw wasn’t an accident and the memory was still a vivid and fond memory.  His eyes glazed over as they looked down at his text book as he remembered it.  His sister was three years older, so the 18 year old girls were well developed and he couldn’t help but peek in through the basement window.  The most developed girl was Brandy and her breasts were full and beautiful in her light blue camisole.  The camisole must have been two sizes too small as it stopped well above her toned stomach and her breasts seemed ready to burst from the camisole cups barely restraining them.  She was wearing tap panties that gave him glimpses of her smooth skin so wonderfully close to her sweet little pussy.  It was all he could do to keep from stroking himself and it was lucky he didn’t as Brandy looked up and saw him staring in.  He was quickly gone, but to his surprise she must not have said anything as his parents didn’t come in and ground him for tom peeping. 

Later as the girls lay in the great room under blankets and sleeping bags watching a scary movie, he stealthily moved down to the basement.  His heart was pounding and he wasn’t sure what he was doing.  His plan if caught was to make a break for the laundry room which was next to where the girls’ stuff was, but the fear of being caught made it even more thrilling.  He was over near Brandy’s stuff when he spied a full slip that she must have had on under her school uniform.  It was light pink and lacy in just the right areas and he could smell her perfume.  His cock leapt in his sweat pants as soon as he touched the silky nylon and a battle for self control was quickly lost and he had his cock out and he slowly stroked the cool silky slip up and down his hard shaft.  He knew he wasn’t going to last long, but when he heard the sound of someone clearing their throat, he nearly fainted.  He dropped the slip and tried to stuff his cock back in his sweats when there was suddenly a hand on it.

He turned and there stood Brandy with the sweetest smile on her face.  He could feel her magnificent breasts pressed against his back and smell his perfume and he groaned as he started to explode.  She squeezed the base of his cock and held on until his cock stopped its spasms.  To his surprise she had stopped his orgasm and she cooed, “Can’t have that; I have plans for your big boy here.”  He swelled with pride at her using the word big and then she guided his hand back behind him and inside her tap panties and then into her very wet pussy.  It was his first touch of a pussy and again his cock started to erupt.  She stopped it again and giggled about how they were going to have to work on that.  She was obviously a hot one as even his inexperienced fumbling fingers had her gasping a moment later and moments later, her lips were searching for his and as she slipped her tongue into his mouth, she groaned and then climaxed. 

He was mesmerized by how she humped against his fingers and he’d read enough books to know about the clit, so he pulled out his fingers as her gasps started to diminish and when he found it and caressed it, he had to slap a hand over her mouth as she started to scream.  He was thrilled that he was able to get her off not once, but twice and it swelled his confidence.  She seemed more than a little surprised as well and when her voice returned, she asked, “Wow, that was a surprise.”  She added, “I need to get back to the movie, but let’s take care of this first.”  She started to stroke him with her hand, but he whispered that he wanted her to use her slip.  She giggled, but bent down to retrieve it.  When he saw her sweet ass like that he couldn’t control himself and he grabbed her by the hips and tried to slide his cock inside the leg opening and into her pussy.  He missed, of course, but she giggled again and said not this time.  She quickly wrapped the slip around his cock and started stroking.  His hands moved to her tits and she seemed very happy with his attention on her nipples.  He even bent down and sucked one through her silky camisole.  Moments later, he exploded.  Spurt after spurt of his cum splashed into her slip and she kept stroking him until she saw his release was complete.  She looked down at her slip and then frowned at him as she said, “What a mess”.  He watched in mesmerized silence as she brought the slip to her face and seductively licked his jizz off the slip.  The moment was interrupted when one of the girls yelled down asking Brandy what was taking so long.  He managed to sneak back upstairs without being noticed.  The relationship involved two more encounters that were incredible, but the second one was interrupted by his mother and so he was forbidden from seeing her again.  That had been three years ago and although his knowledge of girls had grown over those years, his obsession with lingerie had grown as well. 

His thoughts were interrupted when Mrs. Sherman called his name and asked him why he hadn’t turned a page in his book for several minutes.  He looked up and she seemed to be smiling under the stern look she was giving him.  She motioned for him to come up to her desk; something he was very reluctant to do as he had a massive erection caused by his remembrance of his encounters with Brandy.  She was insistent and he was sure that her eyes seemed to widen when she noticed the bulge in his navy slacks.  She pushed herself back from her desk and motioned for him to stand at the corner.  He glanced down and saw that her long skirt had buttons up the front and they were unbuttoned well above the knee.  He also noticed that a long black slip was visible in the opening of the skirt and his cock lurched as he thought of how nice it would be to feel it.  She slid her chair close to him and spoke so softly that he had to lean over to hear her.  She was chastising him for daydreaming in class, but his eyes were frozen on her slip.  She crossed her legs and he swore he caught sight of a stocking top and that threw him for a loop.  If she was wearing stockings and a garter belt under her plain clothing, he had an even deeper affection for his favorite teacher.  It was then that she said, “Where the hell is your mind at right now?”  He tried to look up at her face, but she was crossing her legs again and this time he saw the unmistakable glimpse of an emerald green garter strap.  He was trembling now and felt faint. 

He was vaguely aware of her saying, “Squat down so you can hear what I’m going to say.”  As he squatted, she uncrossed her legs and he noticed her knees widening even more as he leaned back against her desk for support.  In his almost delirious state of arousal, he wasn’t sure of what he was seeing, but he swore that her skirt and slip were now bunched at her waist and he delighted in the sight of the stocking tops of her nude stockings.  As his eyes traveled higher, he shivered at the sight of the creamy white skin of her upper thighs and the hem of the black slip was sizzling as a backdrop to the sexy green garter straps.  He thought it was odd that she wasn’t talking, but he couldn’t tear his eyes away from the wonderful sight so close to him.  His eyes were trying to take in everything at once and that’s when he saw her knees move even farther apart.  He looked up and had a clear view of the silky crotch of her matching green panties.  He desperately wanted to reach out and touch them and feel her silky pussy lips that were hidden underneath, but of course he couldn’t.  It was then that he realized she was talking.   He couldn’t quite understand it at first, but then he understood, “I understand that boys your age are obsessed with girls, but I can’t have my best student slacking off; I need your attention on me at all times…..do you understand?”  He was nodding his head because his attention was definitely on her right now.  He glanced up for a second at her face and noticed that she was smiling down at him and didn’t seem upset at all where he was looking, so his eyes quickly went back to her panties.  He was enthralled by the fact that her pussy was only an arm’s length away and then her panties became even more visible when she inched forward on her chair.  There was diagonal black lace running across the front and as she tilted her hips on the chair, he got an even better view of her panty crotch.  She started to cross her legs and did it so slowly that it seemed like time was stopping and starting.  As his brain processed the fact that there was a very obvious wet spot on her panties, the nylon gusset pulled tight against her pussy and he could see the distinct outline of her pussy lips just as the scent of her arousal hit his nose.  It was all he could do to stop from trying to shove his face between her slowly closing legs. 

He barely stifled a gasp and as her scent triggered a response to his body, she pulled her seat back so her legs were hidden from his sight.  She quietly told him to go back to his seat and as he stood up, just his boxers rubbing against his cock as he stood was too much and he felt his climax start.  He rushed to his seat and slid his hand against his engorged cock and he closed his eyes as he exploded over and over again.  He was glad he wasn’t wearing his khaki slacks as he was sure a wet spot would be forming and hopefully the blue ones would cover it better.  After his release was complete, he opened his eyes and looked around at his classmates closest to him to see if anyone had noticed what had happened.  Everyone seemed oblivious and then he glanced up at Mrs. Sherman.  She was smiling while staring directly at him and he wondered if she knew.  His heart raced at the thought. 

In his room that night, he wanked himself several times with a pair of panties that Brandy had given him when they had to stop seeing each other.  He imagined him and Mrs. Sherman doing all kinds of wonderful things to each other as he stroked himself.  He slept like a rock and awoke energized for a new day.  At basketball practice the next day, he noticed Mrs. Sherman talking to his coach and thought it was a bit odd.  He hadn’t seen her and he was quickly distracted by the tighter skirt and heels she was wearing.  It became obvious that he wasn’t paying attention when his teammate passed him the ball and since he was looking at Mrs. Sherman, it hit him in the face.  It attracted his coach’s attention and as he chewed him out for not focusing, he saw Mrs. Sherman smiling at him.  As she walked out, he started at her ass in the skirt, but he had to focus on practice and didn’t seem her look back at him as she walked out the door.  Late at practice, his coach made him run extra sprints for losing focus and as he gasped for breath he told him that Mrs. Sherman needed to see him before he left.  It was already pushing 6:00, so he wondered what this was about.  He certainly didn’t mind the thought of seeing her in that skirt again, but wondered if he was in big trouble. 

He knocked on her door before entering and when she turned to look up from her desk, he about fell down.  The customary sweater was absent and the blouse she was wearing was both low cut and sheer.  He easily saw that she was wearing something red under the sheer blouse and had a wonderful view of her cleavage.  She smiled and told him to shut the door and come in.  She quickly noted that he could have taken time to shower first, but she seemed to take a look at his toned arms in his practice jersey.  She pointed at a chair that she’d pulled next to her desk and he walked over and sat down in it.  She told him that she needed to finish something up and she turned towards the desk.  From where he was seated, he had a view straight down her blouse.  Without a sweater covering her, he took note of even fuller breasts than he’d even imagined.  His eyes moved up to her face long enough to realize that she was wearing noticeably more makeup and her ruby red lips looked fuller and softer than ever.  She turned to get something out of a desk drawer and in the process gave him a view down her blouse he would never forget.  Although he didn’t know it, what he saw was a red satin bustier and if that wasn’t enough, the bustier had only quarter cups and he saw the most beautiful and enticing hard nipple in his short life.  As she pulled the file out of the lower drawer, her eyes went to him.  It took him a second to pull his eyes away from the incredible sight he had, but he finally did and her eyes seemed to be twinkling at his embarrassment of being caught looking. 

She asked him to go get them something to drink and handed him some money.  Her eyes took a long look at the evident bulge in his practice shorts as he stood and quickly headed to the nearby cafeteria.  His mind was racing as he stood at the pop machine.  He couldn’t believe his good luck and was secretly thankful for whatever he’d done wrong.  His young mind didn’t even consider for a second that his teacher might be teasing him on purpose.  He rushed back to her room and when he turned around after shutting the door behind him, he nearly dropped to the floor.  She was pushed back from her desk, looking in the lower desk drawer that was closest to him.  Not only did he have another wonderful view of her tits due to her blouse gaping open, but her skirt was hiked up to mid-thigh and he could see the tops of her stockings.  They were shorter stockings as they were not even to mid-thigh and as she shut the desk drawer, he could see four blazing red garter straps as well as a silky red slip.  He walked over to hand her the pop and she made no attempt at fixing her skirt.  She swiveled in her chair as he walked around to take his seat and she sat there for a moment looking sexy as hell before finally speaking. 

She asked him what was wrong as his work and focus were completely unacceptable and that if they didn’t improve she might have to fail him and then he wouldn’t be able to play basketball.  He sat quietly with heart racing not knowing how to answer, but yet unable to take his eyes off the view of her stockings and slip.  She quickly took notice of his gaze and added that even now when he was in a great deal of trouble, he appeared to be preoccupied with her legs.  He felt faint when she gestured towards her legs and he simply nodded.  She demanded to know what he was going to do about it.  He was confused as his grades in the class had always been great and so he wasn’t sure how he was being threatened with being flunked and he finally said, “I’m sorry Mrs. Sherman, but I…..um…..I…..er….I guess I’m really distracted by you.”  She reached out and touched his knee and with a touch of humor in her voice said, “Oh Jim, what could be distracting about an old married woman like me…..It’s not like I’m young and sexy like that Ms. Newton that I hear all the boys talk about.”  She slowly crossed her legs and he got a flash of her red panties and he felt wildly uncomfortable.  He finally found his voice and said, “You’re right, a lot of the guys talk about her, but I’ve always thought you were the best.  So smart and sweet, but also so sensuously beautiful……I didn’t really know how hot you really were until I saw your slip and stockings yesterday and now what you’re wearing today, I can barely breath.”

She smiled and patted his leg before withdrawing her hand as she said, “You’re very sweet, Jim, and I’m sorry I didn’t realize I was affecting you.  It must be terribly uncomfortable for you, but you know we can’t do anything, right?”  His eyes moved up to hers and they seemed so inviting.  He nodded his head and she leaned over giving him another great view of her nipples and said, “I appreciate your kind comments as my husband doesn’t seem to notice me lately, so it’s nice to hear I’m attractive to a young man.  If you promise it will be our little secret, maybe I can help you out.”  His mind was racing at the thought and he quickly nodded.  She stood and slowly hiked up her skirt.  His skin was covered in goose bumps as it slowly moved higher revealing her sexy legs and stockings and the full view of the front of her vintage style high waist panties.  She turned and he gazed at how lovely her ass looked in them and then she seductively hooked her fingers in the waistband of her panties and slowly worked them down her legs.  As she bent to work them over her black pumps, he had a glorious view of her pussy.  Her lips were puffy and there was no hair to be seen.  She had to step awkwardly to work the panties off the second shoe and her lips opened up and her sweet pink pussy was on display.  He could see that she was wet and that was an incredible turn on. 

She finally turned around again and he noticed that her face was flushed as she let her slip and skirt fall.  Thankfully, they didn’t fall far and he could still see her creamy thighs above the stocking tops.  She sat back down and rubbed the silky nylon panties in one hand.  She finally looked up at him and said, “I’ve had some boyfriends that loved it when I would rub their cocks with my panties and slips, so I thought that……..”  He quickly said, “Oh my, yes, definitely yes.”  She smiled and said, “Jim, I can’t rub you, but you can take them to the bathroom if you promise you’ll bring them right back.”  His face fell as even though that was a great offer, he had been thinking of something more.”  She held them out and he reached out and took them in his hand.  The nylon was so silky and he could feel the gusset was damp.  His cock was throbbing and he wasn’t sure he’d even make it to the bathroom before exploding.  He stood and his legs shook.  She looked at him and said, “Please don’t get anything on them as that might be hard to explain.”  He nodded and started slowly walking towards the door as he shoved them in his pocket so if anyone was around they wouldn’t see.  He was almost at the door when she said, “Jim, hold on a second.”  He stopped and turned and she asked, “Didn’t I hear that you had your 18th birthday a week or so ago?”  He quickly nodded and she motioned for him to come back.

He wanted to take her and bend her over the desk and plunge his rock hard cock deep inside her pussy, but he stood by her chair and buzzed with anticipation as she seemed to eye his bulge that was only a few feet from her.  As he stood motionless, in a soft quivering voice she said, “Maybe you would let me watch you?”  He gulped and then nodded.  She reached out and yanked down his practice shorts and supporter.  His cock sprang free and she gasped and said, “Oh Jim, how nice…..you’re much bigger than my husband.”  Jim found that confession very complimentary and he sat and wrapped the silky panties around the base of his cock and slowly slid it up his shaft.  Her eyes were intent on his cock and he noticed her lick her lips.  He thought about how nice it would be to have her sweet lips on him, but he knew that was off limits.  She whispered, “Don’t go too fast”.  She then scooted forward so that one of her legs was between his.  He felt her silky stocking against his bare leg and found the sensation wonderful.  She then looked up at him and said, “You know, you probably can smell my pussy in my panties so maybe you’d like to hold those to your face and use my slip to stroke that beautiful cock of yours.”  She paused and added, “The only problem is that my slip is attached to my bustier and so we’ll have to be a little careful how we do this.”  He would have agreed to anything at this point and she stood, unzipped her skirt and hiked it well above her waist. 

He caught a glimpse of her bare pussy again and he had to grip his cock tightly to keep from exploding.  She noticed what he’d done and cooed, “That’s a good boy…..not yet, Jim, not yet.”  She scooted even closer to him and handed the hem of her slip to him.  He tried to wrap some of it around his cock, but it wasn’t long enough.  She tried to move slightly to see if that helped but frowned and said, “Wait, let me try this.”  She stood again and straddled his legs.  As she did so, the silky slip grazed against his sensitive cock head and he groaned.  In this position, he could easily slid some of the silky fabric on his shaft and she he did so and raised the panties to his face after she motioned for him to do so.  She asked if he liked her scent and he said, “Oh fuck yes, Mrs. Sherman, your pussy smells so good, I wish I could eat it.”  She giggled and said, “Jim, you know we can’t, but thank you for saying so.”   She changed positions slightly and he realized that her magnificent tits were only inches from his face.  He pulled her panties away from her face for a moment and as he tugged on the hem of her slip, she fell into him and he quickly sucked a nipple.  She sighed, “Oh Jim”, but pushed back against him to pull free and in doing so, her knees bent slightly and her wet pussy slid sensuously across the tip of his cock.   She gasped this time and slapped him playfully, “Jim, you must behave……don’t do that again.” 

Of course, he didn’t listen and so he tugged on the slip and this time focused on her other nipple.  She pulled back and this time, let the head of his cock press between her pussy lips and for a glorious moment, his head was inside her hot cauldron of wet slippery heaven.  He groaned and she rocked there for a moment before standing up to break the incredible connection.  In a voice he could barely hear, she whispered, “This is getting out of control” but instead of moving away, she pressed her nipple right into his mouth as she trapped his cock against his belly.  She quickly maneuvered his soft cock head against her clit and she rocked against him caressing her quivering love button with his cock.  It was agonizingly wonderful for him, but he desperately wanted his cock to be buried inside her.  He could tell from her groans that was she very close to climaxing, so a moment later, he grabbed her sweet ass, adjusted his cock and pulled her down onto him.  His hard cock slid deep into her pussy right as her climax began.  She threw herself back and with her hands behind him on his knees, she rocked back and forth as wave after wave of orgasm crashed over her. 

Surprisingly, he was able to contain his own orgasm and he relished watching this beautiful and wonderful woman embrace her pleasure.  Moments later her eyes flashed open and she had a momentary look of panic as she realized what had happened.  However, the sensation of his hard cock still being inside her caused her to quickly lean forward and right before she kissed him passionately she whispered, “Cum inside me Jim; fill my hot pussy with your seed.”  She rode him with long hard strokes but just before he exploded, he pulled out and slid his dick down the valley that separated her ass cheeks and she instinctively reached back and stroked him wildly until he exploded in the back of her slip.  She looked at him in surprise, but soon understood why.  He stood and lifted her up on the desk and then buried his face in her pussy.  Within moments of flicking his tongue on her clit, she cried out his name as she came again.  She finally pushed him away as she couldn’t take it any longer.  She finally crawled off the desk as she fixed her clothes and looked at him with eyes that showed she craved more.  She kissed him again and murmured, “I feel so naughty with your cum currently sliding down my ass.  Got enough energy to come over for more?”  He nodded and they arranged to meet at her apartment later.  He left wondering how much more lucky he could get……

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