26yo MTF Tutor X 22yo FTM Idiot

//for this gal's first submission, she is formally requesting your comments (both positive and negative)! help me get better at getting you off :) if you just want the sex, jump to Part 3 Chapter 2

Chapter 1/2: Introduction to Henry

He was a cute little thing, short, petite, with a naturally firm ass and a pale face.

It made his life hell. Perhaps if he'd been taller, stronger, more masculine, he'd always said to himself, maybe then he'd have an easier time being transgender.

He wasn't, though. His unaccepting parents and outright terrible school admin did nothing but remind him, day in and day out, that he was nothing more to them than some troubled little girl.

Come his senior year, Henry was desperately ready to get out this godforsaken high school. Unfortunately for him, getting into college would be next to impossible, as colleges don't tend to like applicants that get repeatedly suspended for four (4!) different bouts of attempted arson.

As previously said, he may have been a devilishly cute little thing, but like the devil, he was a bit of a troublemaker.

So what would come to him, then, but the admin mandated 3-month long tutoring sessions he was to have over the summer prior to his senior year.

Having been held back once already, and desperately failing his math classes, they (that is, everyone but Henry) decided that it would be best if little July (yes, his parents really named him July) would participate in a local college's mentorship program over the summer.

He felt this would bring him nothing but ruin - his time to be his own man, and finally spend some time away from the assholes in his school and the bigots in his family, was instead being annexed by some far away nerdy goody-two-shoes with nothing better to do but teach advanced algebra all summer!

What was truly coming his way, however, was the biggest asshole of them all.

Chapter 2/2: Introduction to Veronica

She was hot, and in the worst possible way. As much as she fucking hated living in Florida - and she felt she had quite a few reasons to hate it in the way she did - there was nothing more irritating to her than the heat.

She was tall, and big. At 6'6", she hulked over the other girls in her college classes - even the other trans girls. When she first went off to college she was terribly ashamed of this. She had, afterall, thought to herself many times how much easier it would be if she had simply been short and petite enough to pass as a cisgirl.

By her senior year, however, she had learned to love it. She had long legs and strong arms and big hands. All the sorts of things she'd felt bad for had, as it would turn out, proven to be quite beloved by her local lesbians. Oh they loved when she'd show up to the local lesbian bars and pick them up, one by one.

The attention she had gotten was intoxicating, and she had learned to love it. More than that, she'd learn to appreciate the (assigned) female body, and had learned how to... work with it. She'd even gone so far as to determine that any sort of bottom surgery was just not in the cards for her.

Afterall, if she wasn't going to get to go around and pick up the sexy, smooth, warm, hot young women around her, wrap her arms around their waists, pin them against the wall and fucking their hot cunts with her hand wrapped around their throat, then what was even the point of living?

And it was in this spirit of sexual liberation that the quite terrible news met her - in order to receive full credit for her classes, she would have to enroll in a summer program to teach troubled youth a variety of subjects. In particular, she was not to leave Florida for the summer (and spend it in NYC with her queer friends, as she had the past three summers). No, she was to head down to some small little town down in the swamps and teach some idiotic little girl how to make numbers go together. What delightful fun.

Chapter 1/3: The Outing of Henry (formerly July)

Henry, 3 months past his 18th birthday, had just met his new tutor barely a week before. She was, no matter how much she refused to believe it, totally cispassing.

In fact, he was amazed to learn she was trans. At first he was frustrated with her, this obvious hulk of a woman should clearly be out playing basketball or woman's soccer or some other thing. She should absolutely not be spending her summer in some hick town teaching high-level algebra to some troubled teenager.

Unfortunately for Henry (and fortunately for his libido), Veronica completely agreed. Although she had managed to avoid any outright bigotry from the parents or the teachers (the apparent absence of which had certainly confused her), she could tell these were not her people. More than that, this girl, the one who closed her eyes and wrinkled her nose everytime she called her July (which was, afterall, her name), was quite difficult to work with. No matter what she did, she couldn't get her to pay attention.

The critical moment, then, was on the first day Veronica called July a handsome woman. Veronica, of course, meant it as insult - the tutor had thought July simply didn't want to pay attention because she could coast through life on her obvious looks. So, as an act of humiliation, Veronica called July "the most handsome woman I have ever seen".

Henry, delighted with the obvious compliment, looked up with doe eyes and responded, quite eagerly, "You mean it?"

Veronica started at him, confused. She looked around his room, where they had been studying for two hours a day for the past week. Henry's room was... different. Clearly very different to his parent's home, at least. His mom hung Live, Laugh, Love in the living room and his dad hung a Thin Blue Line flag (of course emblazoned with a Punisher Skull) off the balcony. Henry's room, though, was... edgy? Veronica had thought that this was simple counterculture, but looking around, she had noticed that the only bit of color - that is, the only part of her students room that wasn't black or red - was a little crystal on the nightstand. A little, cloudy white crystal with bands of pink and blue painted both above and below the equator.

Fuck me, thought Veronica. She looked back at Henry, who himself was still looking at her with wide open eyes.

"Dude... are you transgender?"

Henry's skin flushed, the pink glow lighting up his pale visage. He tucked his hands into his pits and wrapped his arms around his torso, bringing his knees together as he lowered his head towards the ground. The tension of the moment poured through him, up from his chest and into his head, holding him firmly in place. His mouth was dry and aching, his eyes beginning to water...

"Oh, dude...." She looked at him, the little thing clearly not handling this well. I mean, obviously I'm right, she thought to herself, as she considered how to handle this...

Looking left and right, she put her hand on his shoulder, and gripped it tight. Henry would never forget the feeling of her strength.

Frozen in place, his mind now focused fully on the sensation of her strong grip. Terror ricocheted through him - was this a beating? Was she going to call him a slur and smack him around, the way his peers had taught him was the standard?

"Me too."

He looked up with shock. "What?" he asked, like an idiot.

She smiled at him, donning a wry little grin that she quickly put away, choosing instead to affect a more sympathetic appearance.

But she couldn't help herself! Instead she laughed out loud, smacking him hard on the arm and saying "Goddamnit dude, were you not paying attention to that either??"

Henry still stared at her, stoic and unmoving, his heart racing a million miles a minute and his brain moving like a frozen salt-covered slug.

"You are trans though, right?"

A simple question, she thought. It would lead to the most complicated situation of her entire life, and she would absolutely fucking love it.

Chapter 2/3: Henry's Self-Seduction

They did talk it out, ultimately, and she learned his name, pronouns (or rather, the set of them that this nonbinary mostly-a-boy-but-also-sometimes-other-things had taken to using), and lots about the details of his gender identity. He'd even begun talking about his sexual orientation, and had even begun to think about talking about his kinks, before she shut him down.

"Inappropriate." A single word was all it took; Henry shut down. She patted him on the back and encouraged him to keep speaking, and like a leashed dog, he followed her lead. "Just don't make it inappropriate, okay?" He nodded his head eagerly. The point was taken - Veronica and Henry could talk about things Henry couldn't tell anyone else... but she wouldn't let them talk about sex.

Veronica, although more sympathetic to Henry now, felt moreso maternal than friendly to him. His parents, afterall, had clearly dropped the ball, and for once in his life the young man had someone around who cared about him. Or at least, she could choose to be that person. And so she did.

She taught him math, and bits of science, biology, english, composition, hell even some spanish. She taught him everything, and she was quite the nun about it. She didn't tolerate deviations from the lessons, she would never allow for more than a single bout of back-and-forth repartee per lesson, and she would frequently take the long ruler and smack his hand if he started getting bored and doodling while she lectured.

More than that, she wouldn't even let him look away during the lectures. "Eyes to eyes" was her instruction, and Henry... well, Henry learned to love it. His big brown eyes would come to love staring at her, all lesson long. She'd turn her back and his eyes would drift down the definition of the rippling muscles along her biceps, triceps, across her shoulders and down her back. Her large, shapely ass would stand before him, teasing him all class long. And the punishments... Veronica never meant for this, but everytime she would slap his hand bolts of electricity would run through his body.

And the praise? Henry's first true fetish developed when she, finally, praised him. It had been a long series of lessons over the course of their first month together, and his hand - which had previously been stinging red from the swatting of the ruler - clenched as she moved her hand to his head. Some part of him still thought she'd beat him up, just like the kids at school.

Instead, she ruffled his hair and called him, in that beautiful sultry voice of hers, quite the "good boy". God, did he swoon. His knuckles went white and his knees clinked as they shot together, his pert little ass grinding into the seat as he squeezed his thighs against one another, stimulating him in the little way he'd learned to while listening to her teach.

He was dripping wet, and the hotness of his cunt was filling his small little room with an aroma that would forever remind him of Veronica.

Veronica, of course, was completely fucking oblivious. Yes, she was successful with the local lesbians in her college town, but they would literally run up to her and demand to be picked up and lifted into the air, literally fawning over her and showering her in praise. It is, afterall, quite hard to miss the sexual innuendo of a cute little lesbian asking you to fuck her raw.

This, however, cut deeper and required a bit more social intuition to figure out, and social intuition was not her strong suit. Eventually, though, Henry would make it quite obvious...

Chapter 3/3: Henry & Veronica Part Ways

It was months of that. Stern lessons and a teacher quick to anger, and a student that was in love with it. His desire only ever grew more intense, and she remained totally oblivious. She did notice how cute he was, but only in the affirming and kind way. She didn't let herself think any more of it.

4 years later, long after she had graduated and he had let these memories turn into regular fantasies rather than any concrete action, Henry and Veronica would come together again... in more ways than one.

In the time since then, Veronica had left the south and moved to the northeast, living in a little apartment with some college friends as they each tried to build out a career for themselves. She had ultimately managed to get her degree, and had been able to find a lucrative corporate job with it. It was boring, but at least well-paid, work; more than enough to get by, and just barely enough to make the little pseudo-leftist feel bad for not giving back.

She tried to donate money to charity, but found it totally unfulfilling - afterall, who really enjoys having to cut a check? Ultimately she took up volunteer work in her spare time, and it proved to be the perfect compliment to her ever-growing CV.

Her career, her wealth, and her personal life continued to grow. She only struggled at finding love, and the reasons for that are far beyond this little story. Suffice to say, she had finally (mostly) figured herself out.

The same was true for Henry. College had proven to be exactly what he needed, and he would be forever grateful to Veronica for helping him understand the value of a good education. He had, in the naivete of his youth, chosen to go to Veronica's alma mater, hoping desperately to run into her again.

Of course that had never happened, but Henry found himself in accepting circles and, for the first time in his life, with loads of friends and a genuinely comfortable social atmosphere. He even managed to lose his v-card!

Although he had changed a lot, he was still fundamentally, deep in his bones, in that ultimately unalterable way, a complete idiot. And although he had finally learned to take his studies seriously, and had prospered for it, he still had trouble in the one subject that always eluded him.

To finish his degree, he was required to take a class in advanced mathematics, one that built on the foundation of what Veronica herself had taught him.

As he looked for a private tutor to help him figure out what was going wrong with his homework, he found a little volunteer-based organization of people from around the country who would help little idiots like himself. In a moment of continuing naivete, he immediately thought of the last girl who had volunteered to help him, and dreamt of what it would be like to finally run into her again, now that he had come into himself...

On a lark, he submitted a request to the website, asking for help. He was required to write up a little biography for the volunteers to read on his application, and so he shot it out really quickly (and again using what Veronica had taught him).

He figured nothing would come of this, as even if she happened to volunteer for this organization, what are the chances she would see his post, recognize it as his, and then choose to take him on before someone else did? Henry assumed this would be nothing more than another little fantasy born out of the hottest time of his life.

Henry was wrong.

Chapter 1/2: Henry & Veronica Come Together

She knew it was him right away. Could it be more obvious? This cute little submissive had written the most desperate, pathetic post she had ever seen. And not on the merits of his asking for help, no that was normal (and even good, in Veronica's mind).

No, it was how he asked for help. It was how she knew it was him. In hindsight, Veronica remembered Henry as the cutest little submissive she'd ever met. After their months together, she'd finally taken to the BDSM community, and learned (just as much as she had come to accept her body) that she was no switch, no sub, and certainly no bottom. Veronica was a topping dom, and she fucking loved it. She knew what a sub was like, and she had always figured (after they parted ways) that Henry probably was one. For some time she even fantasized about it, briefly, before letting the guilt ruin it.

She had taken to browsing the volunteer website some nights, her hard 7" cock in hand, leaning back in her chair as her chest heaved with heavy breaths. She'd massage her hand up and down, gripping the shaft and pumping it as she gently teased the head, thinking about her cute little subs and their adorable, moon-eyed expressions. She flicked through the posts, thinking about each one of these college kids, always fixated on her perennial fantasy of finding some cute, dumb little sub and teaching them... well, teaching them quite a few things.

She had cum quite a few times to that fantasy. Little did she know, as she finally came across Henry's post, that he'd also been reclining his chair (or rather, laying in his bed as he typed the post on his phone), his fingers circling his clit and teasing his fuck hole as he arched his back, his firm, pert ass clad in skin-tight booty shorts as he grinded his cunt against his own hand, his mind deeply focused on the fantasy of finally coming across Veronica once again.

The post began with his name, and finished with his gender identity and pronouns (after insisting that his tutor be trans-accepting, of course). Veronica saw this and jumped at the opportunity - afterall, how many trans masculine Henry's in need of math tutorship could there really be? And her old college, even! Even if she was wrong, she could at least go visit some old friends.

So why not reach out, right?

Chapter 2/2: Henry & Veronica Cum Together

Henry's heart pounded in his ears. She was coming. His tutor was coming.

As she exited her cute little car, towering over it as she stepped out of it, his big brown doe eyes wandered up and down her body. Fuck she's hot, he thought to himself.

She was tall, of course, but strong too. Better than that, she was confident. She'd been confident, almost even arrogant, in their messages online. Henry had thought maybe she was flirting, but seeing her now, he was desperate to think she'd been flirting.

His eyes drifted down her body to her large, vascular hands and up her body to her broad shoulders.

Fuck... she's just my type he thought to himself.

Her beautiful body swayed back and forth, her ample bosom and wide hips betraying a body so curvaceous that Henry had to take a step away from the blinds and swallow hard, even reaching to a glass of water to clear his throat and help him settle his mind.

Should I change my underwear he thought, as he felt his grool wetting his tiny little panties.

Henry, ever the proud transman, had learned to love his petite, sexy body. His narrow shoulders and soft skin betrayed his inner beauty, his pert ass pushed out of every pair of pants he'd ever worn, and the boxer shorts were just uncomfortable. Instead, he took to crossdressing (so to speak), and had learned to have quite some fun in a pair of woman's panties and a loose little tank top.

Today, he wore his familiar little jean shorts, cut off halfway up his soft thighs, a pair of the thinnest, smallest blackest panties you've ever seen, and a loose black tank top that dangled over his shoulders. From the side, you could even see his protruding nipples and the ever-fading scar of a successful top surgery.

On his feet were simple short white socks, and on his head was the cutest, messiest mop of blackish brownish hair he could manage. Lucky for him, it was quite cute indeed - particularly when ruffled by a domineering trans woman.

Henry was certainly a cutie today, and Veronica was as handsome as ever. She was tall, in her familiar loose white polo shit (the sort she wore golfing with clients as much as she did to read at the local public pool), and a pair of old torn jeans, with the torn fabric betraying her thick, muscular thighs and wide, bouncing ass. Her biceps rippled under her shirt, and her strong (and remarkably) hefty chest filled out the rest of the polo.