The Bad Student

The Bad Student

Jason was asked by Miss Ryan to stay after class. It sounded to him like he had really blown it this time. He was a smart boy, but he liked to goof off in class too much and could be very disruptive. He spent more time trying to be funny than applying himself, and the semester was just about over.

Miss Ryan was a woman in her mid-30s. She had short black hair and wore black framed glasses. She was very attractive, but the joke going around class was that she was a butch dyke. Jason contributed to that rumor. 

He cleared his throat as he nervously stood in front of her desk. "You wanted to see me ma'am?"

She was grading one of the papers. "Yeah, I want to talk to you about your failing grade," she replied without looking up from the paper. 

"Failing grade? You can't fail me," he protested.

She looked up over the top of her glasses. "I most certainly can. But I didn't fail you Jason. You failed me."

"Look," he pleaded, "I'm not stupid. I can pass. We have a test coming up and."

She looked up at him, disappointment in her tone. "Of course, I thought you were smart, but you've proven to be quite dumb. Even if you passed the test with flying colors, you're still going to fail this semester."

"But I can't. I can't stay back a year. I graduate this year."

She smirked. "Not if you fail my class you don't. It is a requirement, and you're not going to make it."

"Please," be bagged. "Isn't there anything I can do? I'll do anything. "

Her right eyebrow arched, and Jason gulped as her look sent chills through his body. "Anything? Are you sure about that?"

He nodded. "Yeah, anything."

"Okay. I want you to come to my house after school. We can go over a few things."

"But, I was going to.' 

"You're going to come over to my house if you want to pass," she cut him off. "I'm only going to offer you this opportunity once. We need to go over your behavior and how it's affected your grade this year, and this is the only time I'm willing to give you. Otherwise, you fail."

"Okay," he replied nervously. "I'll be there. I promise."

She handed with him a piece of paper. "This is where I live. I expect you to be there at 4. Not a minute later, do you understand?"

"4," he replied haughtily. "I can't make it there at "

"You can if you want to pass this class. I'll be expecting you. Don't disappoint me."

He showed up at 3:55, and she opened the door before he knocked. She showed the hint of a smile. "Early? Well, at least you took this seriously. Maybe there's hope for you yet. Please come in."

He brought his books and held one of them up. "I figured you might want to go over the lessons from this semester, but I know the answers. I can."

She waved her hand and interrupted him. "Put those on the kitchen table."

As he was putting the books on the kitchen table, she shut the living room curtain. The room got a dimmer, but it was still light enough.

Jason sat on the chair at the kitchen table. "So anyway."

"What are you doing," she snapped at him? "Did I tell you to sit down?"

"No ma'am."

"Come over here," she ordered. He stood in front of her nervously. This was the first time he noticed what she was wearing. She wore a skin tight black leather outfit. There was some removable parts to the crotch area and the breast area, but they remained attached.

"So," he nervously asked, "what do you want me to do?"

"I'm glad you asked," she said with the hint of a smile. "I want you to strip naked for me."

"You what?"

She put her hands on her hips. "I think you heard me. Strip, now Missy."

"What? Do you want me to have sex with you or something? Is that how I'm going to get my grades up?*

She slapped him hard across the face. "Do I look like some kind of slut to you? Get naked now."

"Why?"

There was another slap across the face. "Because I told you to. Do it right now or get out of my house and accept your failing grade."

Nervously, Jason removed his clothes. He was embarrassed by the not very impressive four inch cock between his legs. It was starting to get erect.

She smirked when she saw what he had. "It's always the little ones that cause the most trouble."

"What?"

She slapped him across the face. "Answer me when I ask you a question. 

Otherwise, keep your mouth shut."

She grabbed a pair of satin pink panties that were sitting on the coffee table and handed them to him. "Put these on."

"Why?"

Again, she slapped his face. *Because I told you to. Now quit asking questions and do what I tell you."

Jason took the panties and pulled them up his somewhat hairless legs.

"Good girl," she smiled. She held a pink shirt that had the words Prissy Little Sissy in red glitter.

"No way," he protested before he saw her hand raised to slap him again. He took the shirt and put it on.

She grabbed a tube of hot pink lipstick and begin to apply it to his lips. "The other problem with you is you are a disobedient little boy, but I bet there's a good little girl in there somewhere, begging for direction."

"Miss Ryan, I'm not sure what's going on here."

She picked up a paddle that was sitting on the table. "The first thing you need to learn is your place. I'm going to spank you for every time I feel you disrupted me during this last semester. I figure about 50 times should cover it."

"That will hurt."

She laughed. "That's the point dear." She sat down in a chair in the living room and looked at the confused boy. "Why don't you bend over my lap and take your punishment." 

"You're not my mother," he protested.

She laughed. "That's the problem dear. Your mother hasn't disciplined you properly, and as a result she sends you to my classroom to disrupt my lessons for the other students, the ones who actually want to learn." 

He stared at her in disbelief. "I don't have to do this."

"You're right," she was growing impatient. "You don't have to. You can leave and take your failing grade. Maybe I'll see you again next year."

"This isn't right," he protested, starting to become resigned to his fate.

"Maybe it is, maybe it isn't." She ran her hand over the paddle. "In any case, it's what you have coming to you. Quit stalling and get on my lap."

Slowly and tentatively he walked over to her and bent over her lap. He felt her hand sliding over his pantied ass. He was enjoying the feeling as she teased him. "You know, really look cute in those panties. I think your problem is you really are a prissy little sissy. You just haven't admitted it yet." 

"I'm no sissy," he protested as he felt her paddle rubbing against his ass, dreading what was coming next.

She laughed. "You didn't fight it too much, did you? Slipping into a cute pair of panties and that shirt. And the lipstick." 

"I didn't have a choice," he protested. Still feeling her paddle rubbing his ass, taunting him with what was coming next.

She laughed. "Sure you didn't have a choice. If I had decided to dress you up in a pretty little Sunday dress and makeup, you would have done that too."

"No way," he started to yell when he felt the paddle come down swiftly on his ass. "Ouch, stop it."

"I've only just begun," she said in a stern voice, coming down hard on the word begun. "You disobedient little shit." The blows came down swiftly, and he had no idea how many she had delivered as he went from begging for mercy to crying.

She stopped. "You really are sorry, aren't you?"

"Please stop," he sobbed. "I'm sorry."

"I really want to believe you," she once again ran her hand gently over his reddening ass. "I really do, but you don't mean it at all. You just want me to stop." 

"Please," he sobbed. "I won't do it again."

"You're right," she said before the blows of the paddle began hitting his pink pantied ass again. "You won't do it again. Disobedient little bitch." The blows came swiftly again as he sobbed and begged for mercy.

She stopped again as the boy was crying uncontrollably and begging. "Please, I didn't mean to." 

She stifled a laugh, clearly amused by his demeanor. "You know what?"

"What," he sobbed?

I believe that was 50 swats.

He continued sobbing as she reached over to the table, pulling down his panties and rubbing a smooth ointment on his red ass. "I don't like doing this, but you left me no choice. Disobedient little sissies like you need to learn their place."

"I'm sorry," he sobbed, regaining his composure.

"Well of course, I'd like to believe you. Stand up." He got up from her lap.

"Your problem is you don't know how to behave when faced with a superior woman like myself."

He said nothing, still wiping his eyes has he watched her walk across the room. What was she going to do next? He wanted to leave.

"I've seen your type, and I've given them just what they needed." She smirked. "You think I am, what was is it you called me?" She paused for a moment. "Oh yeah, a butch dyke?" 

"I didn't mean it," he insisted.

She laughed. "Sure you didn't. You think, what? I don't strut around with long hair and wear dresses all the time, so that it makes me a lesbian?"

He shook his head "No."

"Well, maybe I do enjoy the company of women," she remarked as she gently stroked his cheek. His now uncovered cock stuck out at 4 inches "I do like men. Not little boys like you. I doubt you could satisfy a hamster with that thing." 

He blushed, and her next move surprised him. She removed the breast covering from her leather suit, revealing her cute and perky C cup breasts. His eyes got wider. This was the first time he'd seen a pair of breasts in person.

"Oh, you like that, do you?" 

He nodded. 

"You think you're worthy of touching them?" 

He looked at her, practically begging with his eyes, but he said nothing. "Go ahead," she encouraged. "Touch them." 

He held both of his hands up, just above her breasts before gently touching them. He wasn't sure what he should do next. Would she spank him again? 

She smiled approvingly at him, enjoying his touch. "They're nice, aren't they?"

He noticed how big her nipples were, gently putting his fingers on them and squeezing them. "Yes ma'am, they're beautiful."

"Beautiful huh?" She smiled even wider. She knew she had him right where she wanted him. "They're beautiful now? The butch dyke has beautiful breasts?"

He blushed, enjoying the feel of their breasts in his hands. "Kiss them," she ordered. "Go ahead. Kiss my beautiful breasts. Go ahead and lick my nipples."

"Are you sure?"

"I wouldn't tell you to do something unless I wanted you to do it," she snapped at him. "Do it." 

The teen boy did exactly as he was told, kissing both of her breasts multiple times before moving to her nipples. He licked her left nipple for a few moments before moving to her right nipple.

She let out a light moan. "Good boy." She felt him lick her right nipple, and then he got bold and began sucking it. She pulled away. "Did I tell you you could suck my nipples?"

"No ma'am. I'm sorry I just."

"You like to do things with your mouth, don't you?"

"What do you mean?" 

She smiled and walked over the couch, turning around and revealing her pussy as she removed the l crotch of her leather suit. 

He stood with his mouth open, shocked at what he was seeing. She gently ran her hand over her smoothly shaved pussy, putting a finger on each lip and moving her index finger into her sweet hole. She licked your lips and sat down with her legs spread. 

He stared at her, not sure what to do as she eyed him lustfully. "Well, don't just stand there, come over here and put that mouth to use." 

The sissy boy practically tripped over himself going over the couch. In moments, he was between her legs, staring right at Miss Ryan's sweet love box. He wanted to shove his face in there, but he waited.

"Well go ahead, show me how you use your mouth."

He moved closer, licking her most intimate place and kissing it as she moaned. "That's it, do more of that. You've never kissed a pussy before, have you?" 

"No ma'am," he responded before going back to licking and trying to do what he thought would please her. 

"Right there," she instructed as she ran her fingers through his hair. "Right there. Good boy."

He continued to lick and suck and kiss her pussy, enjoying his first experience, though it was not under circumstances he thought he would ever have in his life. How could he know a moment like this would happen to him?

He became very familiar with Miss Ryan's sweet love box as he gave her what he hoped was a satisfying oral experience. He breathed in her aroma and savored her sweet taste, licking her as she moaned and moved her body. She was having an orgasm, the first of multiples, but she didn't let him stop. 

In his excitement, he wasn't even stroking himself, but he felt certain he would cum at any moment. His little cock was on high alert as he enjoyed the taste of her sweet love fluids.

His jaw was getting a bit sore. After what amounted to over an hour, she stopped him. "Okay my dear," she finally said. I suppose you think we should have sex now?" 

He nodded hopefully. "Yes ma'am. I'd like to."

She laughed. "With that little thing?"

She reached over to the table as she stood up, and he realized that she had a dildo there. He never heard of strap-on sex before, but he was about to get an introduction to it. She put on a black harness with a pink dildo, not huge at about 6 inches and not too thick. 

Miss Ryan was skilled in the art of strap-on play, although Jason had no clue about her experiences. "We are going to have sex, my dear. This will clear you of your bad record, and it will earn you the passing grade you need."

He shook his head. "No way. I ain't doing that." 

She nodded authoritatively. "Oh yes you are. You're doing it because I tell you to, but deep down inside, you want it now." She ran her hand gently on his face, looking him in the eye seductively. "Admit it. Looking at me standing here, you want this in your tight bottom, don't you?" 

"No way," he protested.

She teasingly laughed at him. "Yes you do. Why don't you kiss it. Kiss my cock."

"Please don't make me do that, Miss Ryan."

"I'm afraid I have to, my dear. It's the only way you're going to learn. Do you have any idea how disruptive you were in my class?" She paused, giving him a quizzical look. 

"I've had to put up with you for the whole school year," she continued, "and you're lucky I let you pass the first semester."

"I didn't mess up that badly, did I?"

She nodded. "Yes, you did. I gave you C for the first semester, and you deserved an F. Do you realize how badly you screwed up the final test? Some of the answers were unbelievable. Did you even study?" 

"I did," he replied. "Honestly, I studied hard." 

"I remember you saying that. I remember looking at your test, thinking that maybe you're not as smart as I thought you were if that's as good as you could do."

He started to cry. "But, I tried. I really did."

"I know Jason." She knew he was genuinely hurt by the revelation that he wasn't as smart as he thought he was. "I took pity on you. I thought there was a decent boy in there somewhere, and how did you repay me? By being a little shit in my class for this entire semester." 

"Kiss my cock," she ordered in a loud, authoritative voice. "Now!" 

He nervously got on his knees, leaned forward and kissed her pink cock. "Wait a minute," she stopped him and reached for the pink lipstick. "Put some of this on and kiss it."

He reluctantly complied. Soon, he was kissing her cock again. "That's it," she said with a chuckle. "Get that lipstick all over it. Suck it. Suck it like a little bitch."

Jason felt thoroughly humiliated, but he didn't dare stop. He needed a passing grade. He didn't want to be left behind while all of his friends graduated. Without even being told, he bobbed his head up and down on her fake cock. It was almost as if he'd been doing this sort of thing for years.

She laughed. "And you want to say that I'm gay? You look like a little sissy fairy to me." 

He stopped and looked up at her. "I'm not gay. And you're not a guy. You're a beautiful woman."

She smiled approvingly. "Thank you for the compliment, my dear. Why don't you walk over to the kitchen table and bend over for me." 

"I don't want to," he protested.

"But I do," she replied with a devilish grin. "I want you to go over there and do what I say." 

He slowly stood up and walked nervously to the table, bending over. "He looked back over at her. We don't have to do this. I'm sorry. I really am."

"I know you're sorry, but you still have to learn a lesson my dear." She grabbed some lube that was sitting on the coffee table and went to the kitchen table, standing behind him. He felt something wet pushing against his tight hole and realized that she was sticking a finger inside of him as she began to loosen him up.

"Oh God," he moaned as he felt a second finger pushing into his hole. "This, oh God. It's going to hurt."

"Well of course it will hurt a little bit silly. It will hurt at first, but you'll learn to love it." After a few minutes of fingering his hole, she lubed her pink invader and pushed it against his sphincter. 

He yelled. "It hurts."

"Relax my dear, it will go easier that way. Just take it." Her persistence led to the dildo entering his tight ass slowly as he cried and carried on.

"Miss Ryan," it hurts.

"You'll get used to it," she assured him as she slid a couple of inches into his ass, knowing that he would adjust and get used to it. She started slowly at first, and when he began moaning instead of crying, she knew he was ready.

"Look at you bent over on the table. A little sissy fag taking my cock in your ass."

"I'm not gay," he protested. "You're a woman."

"Yeah, a woman shoving a pink cock up your ass," she chuckled as she continued to thrust inside of him. 

He continued moaning, feeling the pleasure and feeling something weird. He felt like he might cum from her penetration of his back door, and he certainly wasn't touching his cock. He didn't like this, did he? 

She grabbed his hips and picked up her pace. "Look at you, my little sissy bitch. Taking it all inside of you. How do you feel having all of my cock in your ass?"

"I'm not gay," he protested, feeling on the edge of an orgasm.

"Your mouth says one thing," she teased, "but your body says another. Not so tough now, are we?" She picked up the pace, working up a sweat and breathing heavily as she was giving it to him good.

After a few more moments of this, she pulled out, and he was almost disappointed that it was over. However, it wasn't over. She had him lay on the table on his back, taking his legs over her shoulders as she entered him again.

"You're not going to be any trouble again, are you?" 

He looked her in the eye. Was he enjoying this? Why did it feel so good? He didn't understand that with the right skills, a woman with a strap-on could give a man intense pleasure. Miss Ryan was such a woman. "I'm sorry, Miss Ryan. I was wrong."

There was something in the way he moaned those words that she liked. She knew she had gotten through to him, and he meant it. She leaned down and kissed him, catching the boy by surprise. He didn't know what to do, but her tongue went into his mouth and did all the work. 

She continued thrusting inside his ass, reaching down and taking his small cock in her hand as she began stroking it. The pleasure was almost more than he could take, and he didn't want to do what he was about to do. He didn't want to cum while being fucked on the ass, but it was going to happen.

Her words of encouragement would drive him over the edge. "Cum for me, my little sissy. Cum for Miss Ryan." The look in her eye came with a smile on her face as she continued thrusting inside of him while stroking his cock. Finally, he did it. He began shooting cum. 

it didn't go the way he was used to. It almost oozed out of him like a volcano, getting all over her hands, but it was an intense orgasm. The most powerful he'd ever experienced, even if all he had was masturbation experiences.

With her cock still in his ass and his orgasm spent, she moved her hand to his mouth. "Lick it clean."

"No way," he protested.

She frowned. "You've come this far, my dear. Do what I ask of you, and you won't be failing my class. Lick it clean."

He closed his eyes and began licking her hand, tasting his own cum for the first time. She chuckled. "That's it, lick it all like a good little sissy fag."

The words were humiliating, but there was still something reaching the deepest realms of his psyche. There was something about this experience that had moved him. He would never be the same again.

After cleaning himself up, he stood next to her at the door. "You can keep the panties and the shirt as a souvenir. In fact," she handed him the lipstick, "you can keep that too. A little memento of our lesson here today." 

"Miss Ryan, I'm sorry," he said to her as she opened the door. 

"I know you are," she kissed him on the cheek. "I forgive you. You just needed to learn how to treat a woman with respect."

"I will from now on. I promise."

Class was not the same for Jason over the last two weeks. He was no longer disruptive. He wanted so badly to say something to her, but he was embarrassed. On the final day of semester, as every other student left the class for the final time, it was just he and Miss Ryan. 

He stood at her desk, not even sure what to say. "Mitch Ryan, I, have a good summer."

He turned and headed for the door. As he was about to exit, he heard her voice. "Jason, do you like to do yard work?" 

"I've done it ma'am," he turned around. "Why do you ask?" 

She smiled devilishly. "No reason. I have things that need to be done around my house, and I think you might be the right person for the job." 

He looked at her, trying to figure out what she was really up to. "Okay. I'll work for you."

"Excellent," she said that she stood and walked over to him. "I'll be in touch with you." 

"Just let me know," he turned to walk away again. 

"Oh, and Jason, we can have a few more lessons. There's so much more I can teach you."

Her words sent a shiver of excitement throughout his body, but he didn't say anything. He didn't even look at her. He just headed out the door. The hard-on he had in his pants was the indicator that he knew he was looking forward to summer with Miss Ryan.