tagTransgender & CrossdressersHis Teacher, The Transsexual

His Teacher, The Transsexual


Greg was late for class. He ran through the hallways. They were very particular about being punctual here. His health teacher especially. She was very focused on such things. Greg had been late twice this week. He couldn't help that his car kept breaking down. Ms. Sin was a real hardass and didn't accept excuses.

Greg had only started his last year of high school here after his eighteenth birthday a few months ago. He was worried about the impressions he was making. He got to the door of his health class and checked his watch apprehensively. It was 7:58. Greg pumped his fist in his victory. He wasn't late for his 8:00 class. He quickly readjusted his clothing after all that running and turned the knob to open the door.

Inside the room, all the kids were seated already. He looked over to see Ms. Sin had stopped reading out of the study book. He gulped, sweating from the energy he had just expended to run to class.

"I'm glad you decided to join us, Mr. Turner." Ms. Sin stood up from where she had been sitting on her desk and walked over to the class cabinet, carrying out a study book and handing it to him, "Take your seat now, Greg. Don't be late again."

Greg didn't argue. He walked over to his seat and opened his book to the page on the board.

"You're late again, G. This isn't Mr. Lee's fourth period. You can't be late for Ms. Sin's health class." Andy, his best friend, whispered from one desk over.

Greg hadn't been late. It was 7:58 when he walked through the door and the class didn't start until 8:00! He let it go though, nodding his head and looking up to listen to Ms. Sin's lesson.

Ms. Sin wasn't drop dead gorgeous in the Hollywood anorexic model. Still, something about her kept Greg's attention. It's not that she wasn't pretty. She was. She was also very intimidating. She stood close to six feet tall, a fact that was accentuated by the heeled shoes she always wore. She had long dark hair and a warm smile, complete with full lush lips, and the crimson lipstick she was fond of.

Not so hidden in Ms. Sin's blouse were her ample breasts. The black skirt she was wearing today stretched to snugly fit around her thick butt. Greg's eyes wandered from Ms. Sin's lesson to her smooth, muscled legs. She hopped back on her desk, facing the classroom, and crossed her legs. Greg's eyes struggled to see beyond the valley of thigh flesh into her skirt.

He felt a tap on his shoulder and looked over at Andy. "I never even knew we had a gland there, G. This stuff is sick. Why were you late anyway?"

Greg looked back over at Ms. Sin and saw that she had left her desk, she was turned away from them, writing something on the chalkboard. Greg looked at Andy, he whispered, "I wasn't late."

"Oh yes you were. Why do you think Ms. Sin warned you in front of the class?"

Greg was flustered, "I wasn't late. OK!" He said a little too loud.

The class looked back at Greg. Ms. Sin turned her head and gave him a stern look, which gradually softened.

"You weren't late, Mr. Turner? The classroom clock tells a different story." Ms. Sin sauntered down the aisle of desks until stopping at Greg's, she wrapped her hand around his wrist and lifted his watch arm closer to her eyes.

"Mmmhmm." Ms. Sin tapped on the glass face of his watch with her nail and then pointed at the classroom clock, "Your watch is a little early here, Greg." Her brow furrowed for a moment, "Hmm.. this is a good idea." She squeezed his hand and then released it. Ms. Sin walked back up to the front of the class, her hips sashaying.

"Class," She started, "Mr. Turner has brought up a good point. I want all of you to synchronize your watches with the clock on the wall. Don't be late for this class." Ms. Sin smiled. She added, "It is the most important one after all." Nodding in Greg's direction.

The class carried on in an usual manner. Finally the bell rang and kids started shuffling out of the classroom. Greg grabbed his books and headed out the door.

"Wait here a moment, Greg." He heard Ms. Sin call out.

Greg's feet weighed more than usual as he circled back to her desk. He knew that Ms. Sin was a disciplinarian and he didn't want to get on her bad side.

"Yes, Ms. Sin?"

"Oh, I'm so glad you stayed. Usually when I call out for kids to stick around, they're out the door already. It takes a lot of energy to haul them back here," She laughed. "I want to tell you..."

The bell rang again.

"I'll have my next class here in a minute and you shouldn't be late for another period. Go on. Just come by and see me after school. I'll be here." Her next class started pouring through the doorway. Greg nodded his head that he heard her and slipped out the door.

He asked himself, what was that about? Was she going to chew him out after school? Greg didn't have much time to consider the possibilities before he heard someone call out from the end of the hallway, "Turner!" It was Andy. Greg walked at a faster pace to catch up with his friend through the busy hallway.

"Hey G. What happened? I'm surprised to see you here. I figured Ms. Sin was gonna make an ottoman out of you."

"It's your fault!" Greg shouted at his friend, playfully pushing him, though he didn't feel like fun and games. He was just mad at Andy. "She wants to see me after school."

"Oh man. That sucks. I bet she wants to lay into you without kids walking in."

"You think so?" Greg muttered.

There was no answer. Greg glanced out and realized Andy had already walked away to catch his next class. Greg still had a few minutes to catch his class. Greg kicked himself into high gear and ran to his next class, making it just in time.

The hours rolled by slowly. Greg and Andy caught up at lunch and brainstormed over the after school meeting with Ms. Sin. Greg could always say he felt sick if he had to. His afternoon classes went by faster. Even an interesting science class couldn't take his mind off the incident in health though.

The final bell rang and while all the kids rushed through the building and out the doors, Greg walked slowly, killing time. Greg really did feel sick by the time he made it to the health class door. It read: Ms. Sin Room 96 Health Class

His sweaty palm wrapped around the doorknob and twisted it, opening the door. He walked in and saw Ms. Sin sitting at her desk. She was grading papers and didn't immediately acknowledge Greg. He closed the door, grabbing the strap of his backpack and dropped it off his shoulder. Greg exhaled loudly in case Ms. Sin hadn't heard him.

"Take a seat. I'll be with you in a minute." She didn't look up.

Greg sat at the desk directly across from her desk. He folded his hands together apprehensively while she marked something in her book. Greg couldn't help but notice that a couple buttons of her blouse weren't buttoned. They had been at the beginning of the school day. He tried not to look because he felt she would see if he did.

His eyes zeroed in on the cleavage despite his brain's wishes. It wasn't as if her tits were spilling out of the blouse. That wasn't it. Greg could see more than he had in the morning. That was what grabbed his attention. He wouldn't admit it, not even to Andy, but there was something about Ms. Sin which made Greg go wild. This was evident by the erection growing in Greg's pants.

Ms. Sin's eyes shot up to Greg's, "I'm glad you didn't pretend to forget to see me after school or fake sick, or something like that," She rolled her eyes, "You'd be surprised what some of these kids try. This is the way to make it easier on yourself."

"I don't understand, Ms. Sin. Am I in trouble?" Greg had a confused look on his face.

Ms. Sin smiled, "No, dear. Not at all. I didn't want to embarrass you by having this conversation during class." She stood up, walking over to him, "Greg. I like you so I've cut you some slack. But you have to realize, you can't be late to my class. You have to make an effort to get here on time and once you have, you can't talk to your friends. Do you know how disrespectful that is?"

"Yes. Yes, Ms. Sin. I'm very sorry. My car isn't reliable. I need to..."

"No," She cut him off, her tone more serious, "There are no excuses. Do you understand?"

Greg nodded.

"I'm an old-fashioned kind of girl. Respect is very important to me. You show me respect and I do the same. I'm your teacher and I demand your undivided attention in this classroom. Keep that in mind the next time you want to act out in class. You're dismissed."

Greg stood, his face red, and apologized again. He grabbed his backpack and shut the door to Ms. Sin's classroom behind him. He wasn't going to be late tomorrow.

Greg went home and spent most of the night doing homework. He chatted online with Andy but didn't go into detail about what happened after school.

It was the next morning already. Greg left early to make sure he was on time. He was one of the first kids at their desks in health class. Ms. Sin gave him a look, signaling that she saw he was on time.

Before long the bell rang and class started. It began with an assignment in the study book. Ms. Sin collected those, then put her piece of chalk down and rubbed the residue off her fingers. She walked through the aisles of desks slowly.

"This is health class. We do more than just busy work around here," Ms. Sin pointed at a study book on one of the kid's desks. "Knowledge is power, ladies and gentlemen. I teach the consequences of drug use. You learn the basics here about anatomy." Ms. Sin crossed past Greg's desk, her arm sliding over his back as she squeezed herself between the aisle.

"But we also talk about life, living healthy and relationships. We discuss issues of sex with an adult tone. I intend to use my platform here to teach you that knowledge is also tolerance. It's time to highlight the LGBT community. Do we all know what that is?" Most of the class shouted out in affirmative.

"The 'T' in LGBT stands for transgender. Can anyone tell me what a transgender is?" Ms. Sin asked the class.

Someone from the back piped up, "Isn't that those guys that run around with socks stuffed in their shirt and they wear wigs and stuff?"

"Let me explain. And don't shout out next time." Ms. Sin took a seat on top of her desk, "This is a very sensitive subject which hasn't been treated that way for many years. You're thinking of a crossdresser. He or she, however they choose to refer to their gender, may be gay or bisexual, but they're not necessarily a transgender. Transgender people are people who primarily identify with the opposite gender and decide to do something about that."

Ms. Sin crossed her legs, "That can mean male or female. Let's take someone born into a male body who identifies with feminine characteristics. When they decide to begin this process, they become transgendered or transsexual. They either take hormones and or get breast implants. They live as the opposite gender, in this case, as a girl. There are post-op and pre-op transsexuals. Post-op transsexuals have gone through sex reassignment surgery. Pre-op transsexuals haven't."

Ms. Sin crossed and uncrossed her legs again. Greg was straining his eyes to see in between her wonderful legs.

"There's also something called a non-op transsexual. We usually call these women shemales. They live as women and have augmented their breasts in some manner but also like the hardware they were given at birth. I'm going to be blunt here, class. They're ladies with cocks."

The class laughed at Ms. Sin's language and the serious nature of the discussion being boiled down so far. Ms. Sin laughed too and readjusted herself on the desk. It was then that Greg's leering eyes got their eyeful. To Greg's utter surprise, staring back at him was the head of a flaccid penis. It had to be six or seven inches flaccid, half of it sticking out of Ms. Sin's pink panties. It was the shock of Greg's life. Ms. Sin was a transsexual. A SHEMALE!

The class had quieted down from Ms. Sin's comment and she continued, "Shemales retain their cocks and have the same or an even greater appetite for sex than most men and women too. They enjoy using their penises as much as men do. A lot of shemales make dominant partners. Now I'd like to..."

The bell rang.

"Oh alright. Go on. Get out of here, class. No homework tonight!" Ms. Sin called out as kids started packing up for their next class.

Greg did the same, with a sinking feeling in his stomach. He knew Ms. Sin's secret. He couldn't believe his teacher was a shemale. All that time he had been drooling over and fantasizing about a shemale!

"Greg. Come over here. I want to speak with you." Ms. Sin looked over at him.

What? Did she know that he knew? A lot of crazy thoughts were flying through his head as he walked over to Ms. Sin's desk.

"What... What is it, Ms. Sin?" He looked at the floor.

"I want to tell you that I appreciate you being in class early today. I'm glad that you'll take instruction and follow my rules here. It goes a long way." She paused, "... Is something wrong, dear?"

"No. No, nothing. I just have to make it to my next class." He stammered, still not making eye contact.

"That's alright. Run along. I'll see you in class bright and early tomorrow, right?"

"Uh.. yeah. Thanks, Ms. Sin."

The rest of the day was uneventful. Greg tried his best to avoid everyone. So much so that Andy rushed to catch up with him after school.

"What's wrong, G?"

"Nothing. Just nothing."

"You've been wigging out since health class! Come on, what the hell is wrong? I haven't even seen you since lunch."

"I said nothing!" Greg snapped back.

Andy thew his arms up, "Ok. Ok. I'm on my way." He walked off in a direct direction and left Greg alone. Alone with his thoughts. How could he stay in Ms. Sin's class knowing what he knew? He couldn't even face her. This was the woman he had jerking off to for months! She had a cock! A big fucking cock.

Greg slept in the next morning. He resolved to miss Ms. Sin's class altogether. Greg got there in time for second period and tried to push health class out of his mind. That lasted until lunchtime when Ms. Sin found him in the lunchroom.

"Mr. Turner. There you are!" Ms. Sin walked over to Greg's table, leaning over him and putting her fists down on the table, "I thought you were going to be on time for my class this morning. I figured you were sick when you didn't make it at all. Imagine how surprised I was when I learned you had made it to school after all, and just in time for second period!"

"Umm... yeah. It was.. err... right! My car. I'm sorry...." He stared down at his lunch

"I've been a teacher for almost fifteen years. Don't insult me with these excuses, young man. This is a total lack of respect. I want to see you in my room after school. Got it?"

"Yeah... I do..."

"Be there, Mr. Turner." She glared down at him.

Greg muddled through the rest of the day, incessantly worrying about seeing Ms. Sin after school. The final bell rang all too soon. Greg knew what he had to do. He walked through the halls like they were his last steps, sighing heavily at the door to Ms. Sin's classroom.

Ms. Sin was sitting at her desk grading papers like the last time Greg was here. This time though she looked up immediately at Greg, "Have a seat, Mr. Turner."

Greg reluctantly threw his backpack off and sat at one of the desks. Ms. Sin quickly followed and surprised Greg by sitting on top of the desk where he had taken his seat.

She began immediately, "I'm a good judge of matters and I get the feeling that something is wrong," Ms. Sin crossed her legs, "Why did you skip my class today?"

Greg turned away and mumbled something which Ms. Sin couldn't hear.

"I want an answer, Mr. Turner." She told him sternly.

"I... I don't know. I just..."

Ms. Sin grabbed his chin and used it to aim his eyes at hers, "Look at me while we're talking." She chided him.

"I don't know the answer, Ms. Sin!"

Her grip on his chin got stronger, "You're lying to me, Greg."

Greg struggled to get up but Ms. Sin grabbed his shoulders and kept him seated in the chair. She was much stronger than him.

"Damn it. Why can't I get through to you! Why won't you tell me what's wrong!" She shouted at him, frustrated with the situation.

Burning hot tears trailed down Greg's cheeks as he struggled to push his way up, "I saw you yesterday! Ok. You know. I saw that you have... that you're..." Greg stopped struggling and dropped his head.

Ms. Sin's hands suddenly gripped Greg's shoulder so tightly that it hurt. "What! What did you see?!"

"You have a fucking penis! That's what I saw. The woman I've been jacking off to has a fucking penis!" He shouted back at her.

Ms. Sin became aware that they were still in school. She stood up without saying a word and opened the door to check if anyone was around. The place was deserted. She looked at the clock. It was 4:00. The teachers were all probably gone too. Ms. Sin closed the door again and locked it. Ms. Sin walked toward Greg's desk. She sat down at the desk next to him.

"Ok, so you know I am a transsexual. A shemale. Is there a reason you're avoiding my class? I don't see a problem with being a shemale. Do you?"

"No. No. I don't think so. I'm sorry. I didn't mean to you offend you. It's just... I don't know."

"It's just...? It's just... you've been masturbating while thinking about me?"

"Ms. Sin. I... I'm sorry."

"You don't have to be sorry for that, Greg. You've taken my class. You know there's nothing wrong with masturbation. It's quite flattering actually that you would think of me."

"I'm so confused, Ms. Sin. I was trying to catch a peek at you, and then... and then... I saw..."

"Hush sweetheart. It's ok. I understand what you're going through." Ms. Sin stood up and wrapped her arms around Greg, pulling his head into her chest.

"You.. do you feel confused now?" She asked.

Greg's head was buried in Ms. Sin's cleavage and he didn't make any effort to free himself. The big, soft mounds of flesh felt great against his face, even with her blouse on.

"Feeling this way is okay, honey." Her arms caressed his neck and back. She pressed her lips against his head and kissed him lovingly.

Greg's cock had grown in his pants. His cock was leading the charge when his hands reached around Ms. Sin's wonderful body and cupped her full butt cheeks.

"I could lose my job for this. I know you're eighteen but it's still unethical." She reasoned briefly. Her cock had stirred and scared Greg when it pressed against his chest.

Ms. Sin removed her arms and took a step back, her boner tenting her skirt. "It's ok, darling. Why don't we try something we're both sure to like?" She smiled.

Greg nodded his head but hadn't found his voice yet.

Ms. Sin kneeled down on the floor and pulled Greg's legs out of his desk. Her hands pressed against his thighs and finally started squeezing Greg's erection through his jeans.

"This is good, huh?" Her hands continued to squeeze him.

"Yes!" He squealed.

Ms. Sin chuckled, her nimble fingers finding the button and zipper to his pants, she slowly undid them until his erection was covered only by his boxers.

"What do you have for Ms. Sin?" She said in a husky voice, pulling both Greg's pants and boxers down his legs. His hard cock sprang free.

"Such a pretty one. I've got to have it in my mouth. Unless you're still confused?" She asked him knowingly.

"No! No, I'm not I mean."

Ms. Sin wet her full lips with her tongue before wrapping them around the head of Greg's cock. This was a new, wonderful sensation to Greg. Her tongue did a spin over his tip. She created a tight seal around his shaft and started to take it deep into her mouth. Ms. Sin didn't stop until her lips met his boyish pubes.

She had taken the entire length of his cock into her mouth almost effortlessly. Having every inch of his cock engulfed in her mouth was indescribable. The competing sensations of warm and wet and tight came together as she began to suck.

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bySugarandSalt© 76 comments/ 464789 views/ 650 favorites

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