Tom was too nervous to sleep. He miserably flopped down on his bed and tried to close his eyes. Tomorrow was a huge day! He’d be meeting a Senator’s daughter! Just as he was drifting off, he heard his mom’s voice.

“Tom are you ready for tomorrow?”  She sounded just as nervous. Well she had been trying to find him a suitor for a while. While his mom was well off and well connected, she wasn’t a politician. But if Tom married a Senator’s daughter, Senator Felton could help launch his mother’s political career.

“Yes mom!” Tom yelled back down.

“Then sleep well. You’ll need to be well rested for tomorrow.”

Tom drifted into a fitful slumber. That night, he dreamed about painful memories he had tried to bury long ago. Memories of his first.

He had started school at 8, the year most boys were considered fit for instruction. Like all boys, he studied the four basic subjects: cleaning, cooking, procreating and pleasure. Based on his entrance exams and his mother's influence, he was accepted into St. Judith’s, a local prestigious private school. His core classes taught him the art of preparing and maintaining his future wife's house. And of course how to make sure he gave her strong daughters. He learned how to wash dishes, sweep floors, and to best ensure conception. Tom excelled in each subject and earned top marks.

However, he only enjoyed his pleasure classes. From introduction to cunnilingus to understanding erogenous zones, Tom quickly outpaced his classmates, much to his instructors' delight. By the time he was 12, he was learning with boys two grade levels ahead. And when he was 16, he had completed his curriculum. His teachers all agreed that he was the finest male student they’d ever seen. However, his mother was not ready to see him leave. A well-educated man usually married above their station.

When his mother spoke with the headmistress, she informed his mother that it was quite impossible for Tom to study with females, even at the lowest grade level. While St. Judith's provided a progressive education, a man learning with women was unthinkable.

Tom's mother laughed, and explained to the headmistress that she would never dream of sending Tom to study with females. She simply wanted him to continue his education until he was 18 like all of the other boys. After much debate and promises of a sizable donation, the school hired a teacher to tutor Tom individually. She was 16, but was a prodigy. She graduated summa cum laude at Harvard and had written one of the foremost works regarding the instruction of men in female pleasure. Her name was Elizabeth.

When Tom started the 10th grade he was surprised to find a young, thin blonde sitting at his teacher's desk. She wore thin-framed glasses and a tight pencil skirt. Although she was twice Tom's height, she her black peep toe pumps made her even taller. From her red lipstick to her crimson painted toenails, she was a Goddess.

She smiled down at Tom and said, "Hello Tom. I'm your new tutor Elizabeth. You will be studying the art of female pleasure under my individual instruction."

Tom could barely form words but somehow he muttered, "I'm Tom" and shook his tutor's hand. Although they were the same age, Elizabeth's hand could easily cover Tom's, making for an awkward handshake.

"So Tom," crooned Elizabeth, "why don't you show me what you've learned so far?" She spread her legs and peered down at him expectantly.

Tom was floored. He had completed oral exams with his previous teachers, but never on the first day and never on a teacher...like her.

"N-now?" Tom stuttered.

"Yes Tom." Elizabeth lectured her dumbfounded student. "How can I know where to begin your instruction without evaluating your progress?" She tapped her pump impatiently. "Hurry up, I don't have all day"

Hands shaking, Tom shuffled towards his teacher, her blue eyes studying his every move. He fumbled with her skirt, fingers struggling to hold the oversized zipper. As he removed her skirt, Elizabeth lifted her legs, allowing Tom to pull the heavy garment off. He had better luck with her panties, which were lacy and light.

Tom stared in awe at Elizabeth's womanhood. Sighing, Elizabeth reached down and led Tom towards her. Tentatively he pushed his tongue against her, and buried his nose against her skin. Although his teaching had been extensive, every woman was different. He was too nervous to hear Elizabeth's moans as he filled his mouth with her clitoris and sucked. After what seemed like an hour, he felt her flesh spasm, and a trickle of liquid ran down his face. His collapsed to her legs, exhausted.

She tilted his head upwards, off of her long legs and up to meet her eyes. Although they had just met, Tom felt as though she knew everything about him.

"You're inexperienced, but it's a start. We have a lot of work to do Tom." She looked down at him clearly unsatisfied. However, she didn't seem disappointed. She seemed…hungry. "That's all for today. Here is your textbook, read pages 1-50 tonight. They'll cover the basics."

Tom nodded, clutching the book she had handed him. He looked it over and was shocked to see Elizabeth's name on the bottom.

"It's my book, but it's been edited for male readers. The female version is much more dense. And don't forget your tongue exercises!"

"Tongue...exercises?" Elizabeth talked so fast! She came from female academia, where conversations easily outpaced male thought. While Tom was smart for a man, he couldn't keep up with natural female cadence.

"You've never done them? Well they're detailed in my book." She wagged her finger at him, lecturing, "Females are difficult to satisfy. If you're going to keep your future wife happy, you'll need a strong tongue!" She sighed. "I hope you are a good student Tom. You have much to learn. Now head to lunch, and after we’ll study female anatomy."

Tom stumbled out of the room, exhausted both mentally and physically.

Over time, Tom began to perform to Elizabeth's exacting standards. While he had learned about the five female erogenous zones, Elizabeth taught him the best way to stimulate each area.

He learned how to accept a woman's kiss and signal he was ready for more. Elizabeth had small nipples, but he learned how to stimulate them until they filled his mouth. His oral education continued in both the clitoral and the anal regions.  And Elizabeth taught him that one of women's biggest turn-ons was sucking their toes. Tom's favorite learning experience was running his tongue over her perfectly painted toenails.

"Now Tom who was the President who acquired the Louisiana Purchase from the Queen of France?"

"Um...Martha Washington?"

"Tom you know that's not right!" Elizabeth looked concerned. "Tom, you've been distracted," Elizabeth lectured, dangling her flats. "It's been taking you longer than usual for you to make me cum, and you haven't cleaned my desk properly in days"

Tom's eyes were on her dangling feet. He had painted her nails blue yesterday, and as her perfect milky sole balanced her flat on her toes, he was praying for just a glimpse. He watched her foot move back and forth, filling his field of vision.

"TOM!" Elizabeth slapped her flat against her foot and snapped Tom back to attention. Suppressing a smile, she shook her head. "Tom it seems like all you can focus on is my feet. Very well then, show me what your learned in the last week."

Tom leaped out of his desk and knelt before her. She loomed high above him and her legs seemed to stretch for miles. "Remove my shoes Tom and kiss my feet.” Elizabeth commanded. “Your future wife will expect this, it's the first step in most foreplay."

As he admired her blue toes, Elizabeth leaned over him and whispered, "Don't they look lovely? You did do a good job painting them. Go on, I know you want to kiss them."

Tom needed no further encouragement. He bent down and started by kissing each of her toes. He then massaged her sole, starting with gentle circles and finishing by licking them from top to bottom. He loved how she wiggled her toes as he pleased her. As Tom took her toes in his mouth, Elizabeth half lectured, half moaned, "Tom, you're going to have to meet with me after school. We need to make sure you pass the end of the year exam."

Tom would have said yes, but his mouth was full with Elizabeth's toes, he simply nodded.

"Goooood...next week after you...drop your books at home, have your mom drive you back...so we can continue…your education" At this point Elizabeth was so wet Tom could smell her scent, even from the floor.

"At least I can please her like this" he thought.

When Tom told his mother about his after school education, she told he that it was a delightful idea and she would be happy to drive him. The next Monday, Tom returned to his classroom at 5:30 for his extracurricular education.

Elizabeth was sitting on her desk waiting for him. She had changed into a tight sundress with gorgeous white wedges. She looked incredible.

Elizabeth raised her eyebrows and asked, "Are you alright Tom?"

With a start, Tom realized he was staring. He muttered, "I'm fine" and moved towards his seat.

"Not there Tom" Elizabeth chided. She pointed to the ground in front of her feet. "I need your full attention"

Tom sat and tried his hardest not to stare at her feet dangling in front of him. He lasted a full 30 seconds before he snuck a peek.

"Now Tom, explain to me the physical and mental differences between men and women. If you get this right, we can move on to something more interesting"

"Women live much longer and age much slower than men.” Tom recited. “Women usually live to be 150 years old and ovulate their whole lives. Women also keep their beauty until their final years and never get wrinkles or grey hair like men. Women grow to a height between 6 and 6 and a half feet tall, where men usually don't live past 50 and rarely grow past 3 feet.”

"Very good Tom" Elizabeth began to slip her feet in and out of her shoes. As she noticed his eyes beginning to drift she chided, "Stay focused Tom!"

"What?" Tom looked up, "Sorry Miss Elizabeth. Women are much more in touch with their emotions. They can control them much better than men and women think much faster. Women learn quickly and easily outpace boys their age. Men are prone to making poor decisions and are not able to participate in most female conversation"

Elizabeth clapped her hands and smiled, "Excellent Tom! Just a bit more."

"Most men have the cognitive abilities of a 7-year-old female. Even the most intelligent men can't understand a basic lesson in the female fifth grade. Women mature around 12, and usually marry their first husband by 18. Oh and women have high metabolisms and lean strong muscles, which gives them their lithe, beautiful frames" Tom's eyes started to drift along Elizabeth's curves. Focus! "Men have denser frames which means that while women can easily overpower them, women don't break men's bones during intercourse."

Elizabeth smiled and quipped, "I like the way you're thinking Tom. Now I want you to practice your oral technique." She spread her legs and Tom realized she wasn't wearing panties. He lifted his head through her dress and began his assignment.

"Yes Tom, yes Tom, yessss" Elizabeth pulled his hair as he felt her legs contract around him. Her vagina was so wet, he was afraid his head would slip into her. In less than ten minutes she came. As he felt her body shake, Tom tried to pull his head away. Elizabeth felt his reluctance and pushed his head closer. Her fluids washed over him, filling his mouth and soaking his clothes. Tom began to stop, but she cried, "Keep gooooing". His hair was soaked but Tom continued to stimulate her clitoris. She came again, but allowed him to pull his head out of her dress as she writhed in pleasure.

"Mmm well done. You've never made me cum twice before. Now for extra credit, can you tell me about female orgasm while you clean up after me?"

“Ok Miss Elizabeth” Tom said meekly. “When a woman is stimulated sexually, she produces two fluids. The first is a clear fluid that serves as a lubricant. The second fluid comes gushing out when the woman orgasms. It is clear and sticky and has a distinct scent. The amount of ejaculate depends on the intensity of the orgasm, but can be anywhere from a trickle to a liter.”

“Very good Tom!” Elizabeth smiled as he wiped up her fluids. “I knew you were a hands-on learner!”

 
The next day was the same. Elizabeth would ask him about the day's lesson, and then he would give her oral sex until she was satisfied.

After school that Friday, Tom found Elizabeth waiting for him in a tight black dress that perfectly accentuated her curves. She had her hair up and had traded her glasses for dark red lipstick. Her stiletto heels made her nearly three times his height. Tom’s head barely reached her thighs.

"Good evening Tom. I apologize about how I'm dressed but after our lesson, I'm heading to the club with some old friends from school." As she spoke she adjusted her bra, capturing Tom's full attention. "Do you like it?"

"Y-yes Miss Elizabeth." He took a deep breath, "B-but your toenails aren't painted" He couldn't believe he had said something so bold.

Elizabeth smiled. She studied her feet, as if noticing the lack of color for the first time. "Tom, would you like to paint my nails? It's about time you learned to multitask."

Tom sprung out of his chair. She handed him a bottle of black polish and unzipped her heels. The brush was big for Tom's hands but he didn't mind. "Now Tom while you work on my nails, can you tell me about a man's role during sex?"

"Umm...sure." This wasn't what they covered in today's lesson. Tom struggled to remember the lectures from his intro to intercourse years ago. The intoxicating smell of the nail polish and Elizabeth's feet made it hard to concentrate. He had finished her right foot before he remembered. "A man cannot become fully aroused on their own. However there is a supplement to help. There are two variations, which usually come in a pill. The first is a stimulant that increases arousal in men. The second allows for fertilization. The pills are only sold to women, to prevent misuse by men."

Talking and painting had taken a while but he had finally finished her left foot. The polish dried quickly as Tom looked up at Elizabeth's piercing blue eyes.

After a while, she laughed. "I'm impressed you remembered! And my nails are perfect!" She leaned down to give Tom a kiss on his cheek. While Tom struggled not to faint, she continued, "I think you're ready for something new."

She reached into her purse and showed him a tiny green circle. "Tom do you know what this is?"

Tom studied it "I'm not sure Miss Elizabeth."

"Really? You just told me so much about it! Have you ever been with a woman Tom?"

Tom froze. She couldn't possibly be suggesting what he thought.

She raised her eyebrows and lectured, "Tom if you want to please your future wife, you need to know how she wants to fuck you."

"But Miss Elizabeth" Tom protested, "None of my other teachers did this"

"None of your teachers got this far in your education. Besides Tom, don't you like me?"

She pouted as she ran her hands up and down her tall, sexy body. Tom watched as she played with her breasts and ran her fingers over her hips. Her hands caressed her thighs, stopping for only a moment to flick across where her legs met.

She had turned Tom on before but never like this. He couldn't think or fight anymore. He simply knew that he needed to be with her.

He felt his hand reaching up to hers, moving on its own. She smiled and closed her hand with a snap. "Not yet! If you want your first time to be special, you have to work for it." She pointed at her newly painted toenails. "You know where to start."

Tom bent down and started kissing her feet. He could feel her looking down at him, urging him on. As he sucked on her toes she started to moan. Her scent wafted down and Tom knew from experience that she was ready for more.

He began to move up her body. He kissed every inch of her towering pale legs and bit her thighs as she moaned above him. As he attempted to pull up her dress, he felt her strong feminine hands lift him up into a warm kiss. Her lips covered his and her tongue forced itself down his throat. She left no doubt as to who would be guiding this interaction.

As she broke away for air, Elizabeth removed her bra and loosened the straps on her dress. As it slid to her waist, she shimmied out of it. Her movements nearly made Tom fall off her lap, but it was worth the risk to see her full feminine glory.

Her breasts, as bigger than his head, sat right in front of him. Small pink nipples begged to be teased. Tom only had to suck on them for minutes before she whispered, "Tom I'm ready".

Her long fingers placed the pill in his waiting mouth. As she pulled them back, Tom sucked on each one. Elizabeth smiled and Tom quipped, "See? I have learned something." Elizabeth didn't say a word. She reached down, ripped away his clothes and pinned him to the desk. Tom began to worry about coming home naked when he felt his blood rush downwards. Then he forgot everything but her.

As she watched him grow, Elizabeth whispered, "I knew you'd be big enough to fill me" as slid herself onto him.

She felt incredible. He had heard men describe sex as losing oneself inside a woman. Tom now knew what they meant. Elizabeth felt warm and wet and he wanted to give all of him to her. As she rocked back and forth on top of him, Tom was mesmerized as her breasts moved. On instinct, he pressed his face to them and sucked her nipples. Elizabeth started to moan louder. She pushed up with her legs, nearly slipping off of him, and then brought herself down, engulfing him inside of her. As he'd been taught, he bucked his hips each time she slammed herself down into him. Her body was heavy and he knew he'd have bruises the next day, but pain was part of sex for men. Elizabeth wriggled on top of him, straining to pull every bit of him into her body. She moaned, "Tell me how bad you want to be mine"

Tom could barely breathe. Every time she came down, she drove the air from his lungs. In between gasps, he said, "Elizabeth take me. All of me. Make me yours"

She dug her nails into his chest, arched her back, and screamed. He felt her fluids wash over his naked body. He breathed a sigh of pleasure and relief only to have it driven out of him as she pushed down even harder. She said, "I'm not finished with you yet Tom." She kept going until sweat and cum covered both of their bodies.

When she picked him up, his mom didn't even ask why he was naked. She just smiled and said; "It's about time"

The next two years of his education flew by. The after school meetings moved from the classroom to Elizabeth's apartment. Under her expert instruction, Tom passed his final exam with flying colors. During his oral exam, he made her cum within minutes. His mom beamed when he made the headmistress cum even faster. They all agreed Elizabeth's instruction had been well worth their money.

After his graduation, he went to Elizabeth's his classroom one final time to get his things. Elizabeth was waiting for him, sitting on her desk as always. "Hello Tom. Congratulations! You were fantastic today. I think the headmistress may be inviting you over to her house very soon."

Tom smiled, "Thanks Miss Elizabeth! I couldn't have done it without you!"

She shrugged, "You were a good student. But you know, I think I deserve a thank you." She looked at him expectantly.

Tom already knew what to do.

After they had finished making love on her desk, Tom laid his head on Elizabeth's chest. "I wish I didn't have to graduate" he sighed.

Elizabeth stroked his hair. He felt her pause, and take a deep breath. "Tom, I'm leaving for grad school"

He looked up at her in alarm. "What?"

"I'm studying for my master's degree in education. I got a full scholarship to Stanford. I'm leaving tomorrow."

Tom couldn't move. What was she saying?

"What I'm trying to say is…that this is goodbye Tom"

"Take me with you!" Tom pleaded. "You can keep teaching me!"

"Tom, men aren't allowed in Stanford’s classrooms, unless they’re test subjects. And I've taught you everything you need to know." Elizabeth smiled. "I have to move on Tom"

Tom's heart dropped. "Elizabeth you're my first. You've been my life these past two years. I LOVE you!"

Elizabeth sighed. "Tom I care about you. I truly do." She shook her head, "But I can't split my time between you and my degree. I had to choose. I'm sorry Tom."

Tom held back tears. How could she do this to him?

"I didn't tell you until now because you had your final exam and you had been doing so well! I didn't want you to be distracted." She pulled him close and kissed his head.

Tom's breath came in short gasps as he held back tears. He needed something to hold on to. A final memory of her. One last passionate kiss.

He leaned in, but she drew her head back and gave him a wolfish smile. He felt her long fingers run through his hair, and then she drew his head downwards. In those seconds, Tom's little mind began to race. Perhaps she wanted one last time. But she had already taken him. And then told him she would be leaving him. Forever. This wasn't about goodbye sex. This was about power. She wanted him to pleasure her. Not for a class, not to win her love, not even as a goodbye. She wanted him simply for her pleasure.

He was crushed. Had she ever cared? Was he only her trained tongue? He felt betrayed, yet somehow he wanted her even more. And the more he thought about it, the more he realized it was romantic in its own way. After all, the first time they truly met was when he placed his head between her thighs.

So as her soft yet insistent hand pushed his head downwards, he allowed her to guide him, as she had that very first time. She came almost as soon as his tongue touched her labia. His teacher held his head in place as she soaked him again and again in her fluids. Like a good student, he continued as the orgasms rolled through her. By the time she was finished, Tom was soaked through and he could only taste her sex. As she wiped away sweat from her flushed cheeks, she sighed, "I taught you well"

Tom looked up at her, tears in his eyes. He leaned in, pleading, begging her for a goodbye kiss. She smiled, and her lips pressed against his. As she enveloped his mouth, Tom flicked his tongue against her lips, one final plea. At that moment, Tom would have been her student, her test subject, whatever she wanted. He just wanted to be hers.

He could feel her smile through their kiss, as if she heard his thoughts. For one moment, Tom dared to hope. Then her smile faded, as she pulled her lips from his. She walked through the doorway, but not before blowing him one last kiss.

He tried to block out the memory, but the final pieces came rushing through. He remembered crying on his mothers lap as he told her everything. She smiled at his naïveté and told him matter-of-factly that although Elizabeth was the first girl to break his heart, she wouldn't be the last.