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My New Coach, Jesse	By : ShadowProc213 Category: +G through L > King of the Hill Views: 5954 -:- Recommendations : 0 -:- Currently Reading : 0
Disclaimer: I do not own King of the Hill or any associated property, I make no money from this writing.

Chapter List
- 1-My New Coach, Jesse
- 1
It took 'him' over thirty minutes to get ready in the morning. There should be a better explanation, but then again, most men don't keep long hair, or lipstick, or eye-liner. Nail polish just made that a whole new mess. But by the time he was finished getting everything ready, including tucking certain things away, and putting on the right type of dress, it was already thirty-eight minutes. Luckily, timing is everything, and he got up early so that 'she' could walk outside every morning as Jesse...
Long black hair, freshly painted fingernails; it was enough to make her prance the whole way to school. Which, actually, she did. After all, there are perks to living very close to your school, and one of them is that you never need to walk too far. Even on the first day of school, this still felt nice; and the first day of school felt like the right time to unveil herself. It took all summer to clear it with the district; and, standing at six-foot-four, there were few students who could actually hurt her in any meaningful way.
Getting inside, she immediately heard a commotion and, like everyone else, ran over to check it out. It was a few 'unattached', but very athletic, students, pummeling a little butterball freshman. It was a pity, too, since they could be really useful on most of the sports teams. Jesse looked over at one of the teachers, who just glared at the floor, knowing he'd likely be fired if he intervened.
Jesse took two steps in, and tore both attackers off this poor kid. "Hey guys. Feel like taking on someone your own size?" She taunted. When they both saw her, they gulped and shook their heads. "Good! Then stop picking on freshmen!"
As everyone was dispersing, the chubby freshman who had had been attacked walked up to her. "Why are those guys so afraid of you?" He asked.
"For one, they're cowards." Jesse giggled. "For another, I'm bigger than them. Now get to class."
When that kid was going through several different classes, until he hit Physical Education. Everyone was in the same outfit, except the teacher... It was Jesse, the woman who had helped Bobby earlier, and she was wearing much tighter versions of what all the students were wearing. There was a student who questioned this.
"Why are you in short-shorts? And aren't you a little young to be our teacher?" Connie demanded.
"The school loves saving money, and I this is only costing them five credits toward my graduation. They said I could pick my own uniform, as long as it doesn't feature any corporate logos. This was my uniform when I was your age!" The teacher answered enthusiastically. "Now, let's get to work!" With a big smile, she started ordering them through all of the proper drills. The only one falling behind was the boy from this morning.
When everyone was leaving, she took him off to the side. "Last class of the day. Headed home, Bobby?" She asked.
"Yeah-- how did you know my name is Bobby?" He asked, clutching his own sleeves.
Jesse held up the clipboard, showing a laminated sheet full of little photos. Each one had its own name and phone number. "They give us these charts, so we can fake remembering the students' names."
"Is this where you tell me I'm too slow, too fat, and I need to work harder?" Bobby asked, clearly already offended.
"You are, by a wide margin, the least healthy person in this class." Jesse admitted. "But I wouldn't just give you some hollow advice. I can help you."
"Aren't teachers supposed to stay away from students outside of school?" Bobby asked.
"That's something of a gray area. Watch this." Jesse pulled out a phone, though Bobby couldn't tell where it had been just a moment ago, considering the size of that outfit... and the shape of everything under it. "Hello, Mister Hill? I'm your son's Gym teacher. No, your son hasn't done anything wrong. I'd like to tutor him personally. My name is Jesse Louis. Alright, see you then!" She turned to face Bobby. "I'm going to meet your parents. Get into your street clothes, then just meet me at the first house across the street from this school."
"Do I get a say in any of this?" Bobby asked, still sounding offended.
"You get a say when you get in shape." Jesse smirked at him. "See you at my place."
When Bobby walked just across the street, and knocked on the door, he was invited in by the same woman who he'd been seeing all day. "Do you actually live in this house?" He asked. "Across from the school?"
"Yeah, it's going to make the driveway a nightmare for the next hour, but we've got a few ways around that..." She teased, leading him to an alley where a very nice car was parked. "Sneaky, sure. But there's no way that I'd risk playing bumper cars with those jackals."
"Why do you call them 'jackals'? Everyone at the school really seems to like you." Bobby thought aloud.
"They don't really like me, but because I'm a football player, gymnast, freestyle wrestler, and a self-defense instructor apart from the school..." Jesse listed. "When they found out something about me, well... let's just say there's a reason I'm going to spend my afternoon tutoring you instead of hanging out."
When they arrived at the Hill household, Bobby hopped out of Jesse's car, and then Jesse stepped out, much to the shock of Hank and Peggy.
"Um, is Jesse going to be coming along soon? He said he was interested in teaching my son." Hank asked, clearly very confused.
"I am very interested in teaching your son!" Jesse affirmed, taking a few steps forward. "Sorry about the heels, and the dress. I know that we're here to talk about sports, but I like to look my best whenever I'm meeting any kind of clients."
Hank still seemed lost. "But... I read that last season, you matched my rushing record. They had a picture. Your hair was a little long, but-- you had a goatee!!" Hank was actually yelling. He wasn't angry, just frustrated.
"Yup. I'm the exact same Jesse Louis, with a fresh new look. Fair warning though, Mr. Hill, I am still matching your rushing record for every year thus far, and I'm planning on breaking your record this year!" She was pointing in an exaggerated manner.
"But, you were a guy!" Hank half-sighed, honestly looking lightheaded by the whole thing.
"But I didn't LIKE being a guy. I do like all those sports I got involved in, and that's why I'm going to help train your son. I'm an athlete, and that's what he needs." Jesse managed to bark before Hank passed out.
Hank woke up a while later, on the couch, and stumbled into the dining room where the others were sitting. "So, you're going to get Bobby in better shape?"
"No, Bobby is going to get Bobby into a better shape. But I'm going to help." Jesse corrected as gently as she could.
"Help how? I am a real teacher, and I haven't been able to do anything with him in fourteen long years. What makes you think you'll be able to fix this like some magic bullet!?" Unlike Hank, Peggy really was angry. After all, she was Substitute Teacher of the Year! "What do you have that I don't?"
"Motivation." Jesse answered, and picked up her bag. "See you in class tomorrow, sweetie!" She said with a wink, then drove off.
"Can you believe that cross-dresser calling our son 'sweetie'? I have half a mind to call the school and--" Peggy wasn't actually cut off, she just couldn't think of a proper threat.
"Now, Peggy, this might be good for the boy. A few stress-induced psychological issues aside, Jesse seems like a great role model."
It took a few weeks of just increasing the basic drills, then it came to a very special challenge. They were at Jesse's house, and Bobby was finishing his basic exercises.
"Okay, Bobby. You've finished with all of the warm-ups. Time for something new. This one is called 'strip training'." Jesse instructed, taking a seat on her couch. "Plays just like strip poker."
"Why would I want to see that? You're a guy under there." Bobby reminded.
"Alright. Every time you fail to do the exercise, you lose an article of clothing. If you succeed, I'll show you some porn that you're not supposed to see." Jesse explained.
"What if I end up naked in front of you?" Bobby asked.
"Have a little faith in yourself. That won't happen." Jesse sneered, "And if it does happen, then that's a bridge we'll cross when we come to it."
Bobby always felt like he was missing out on some choice, but this one he took by the reins. "What's up first?"
"Twenty push-ups. Right hand only." Jesse ordered. It took just under a minute, and some visible strain, but he did it. "Good boy." She said, and tossed him a Sports Illustrated Swimsuit Edition.
"This isn't that great. I see more skin from Luann's friends in her pool." Bobby complained.
"Of course it's not great. The first thing I'm going to get from you is a sock." Jesse corrected. "Keep it up, and you'll be seeing much more exposed women in no time. Take three minutes to catch your breath and browse through the magazine." She just sat there and watched as his eyes got wide at the centerfold, then that slow sigh as he was clearly trying to suppress his small amount of excitement. "Thirty crunches."
"Augh!" Bobby failed at that, managing twenty-seven, far more than he'd previously been capable of. He pulled his sock off, tossing it off as he fell onto his back. Looking up at Jesse, Bobby saw a mild frown, and closed eyes. "Sorry. I didn't mean to do that."
Jesse inhaled deep, and actually savored the smell of this boy's sweat permeating this little cotton thing. She brought a hand up to her face, and hoped she'd hidden the fact that she stuck her tongue out, trying to taste Bobby's foot. Realizing that it mostly just tasted like cotton, she tried for her next instruction. "Fifteen push-ups. Left hand only." She saw Bobby struggling, and started ordering. "Do it now, or you lose your other sock." She barked.
Bobby did try, and he quickly failed. The body can only take so much, and he had already been put through the wringer before this so-called game had even started. "I don't think I can do this." Bobby said, gasping for breath, barely able to maintain his stance at all-fours.
Jesse stepped in and helped Bobby get up, and get onto the couch. When she sat down next to him, "Take a breather." She put a hand on his shoulder. "You're trying, hard, and that means a lot. You're just hitting a wall right now."
"I'm supposed to take off something else, now. Right?" Bobby asked, already taking off his sock and tossing it over where the other one had landed.
"So, we've been talking about fitness for a while..." Jesse trailed off.
"That's literally all we talk about. It's why I'm here right now. You're my gym teacher." Bobby said all of that, and only afterwards realized how hurt this person sitting beside him looked. "I didn't mean--"
"No. You're right. I'm sorry if you don't want to talk about anything personal." Jesse frowned. "Whenever you're ready, you just need to try the push-up challenge again."
"Before we get back to work, could you tell me what the school found out that was so bad?" Bobby asked.
"Sure. Get started, and I'll talk while you--" Jesse was caught off-guard as Bobby leaped to attention, starting in on the push-ups, "Okay, well, I spent most of my life unsure of my gender identity. I've always been more comfortable in girls' clothes, but I wasn't ready to risk telling everyone. I thought that here in Arlen, everyone would call me a freak. I came out to my parents about liking boys shortly after my fifteenth birthday, and they've tried to be supportive. I tried telling everyone the second part earlier this year. The school decided that they still need me around, but my friends decided it was best to just avoid me..." Jesse looked up, and she saw Bobby doing the one-hand push-ups as instructed. "How many of those have you done?"
"Forty-eight, forty-nine, fifty!" Bobby proclaimed, rolling onto his back afterward.
"I said fifteen, not fifty." Jesse commented.
"Your voice was so pretty, I wanted you to keep talking." Bobby teased as he looked up at her. She held up a playboy, offering it to him. "The magazines are a dumb reward. It's not like I could use them here anyway."
Jesse pulled her jersey off over her head. They may have been covered by a sports bra, but Bobby was being given a very good view of her breasts. "What do you think?"
"Are they real?" Bobby asked. It wasn't an unfair question, since even a lot of the girls in the school stuffed their bras.
"You did more than double what I asked, and I suppose that attitude should be rewarded." Jesse took off the bra, revealing two real, soft breasts.
Bobby got up and took a closer look, "These look really good for a boob job."
"It's not a boob job. It's hormone therapy. I must admit, I'm liking the results so far, and yet they haven't finished growing." Jesse laughed a little, now that Bobby was being more tactful. He started instinctively reaching out, "You can touch me if you want." She smiled at him.
Bobby took that offer, and ran a few fingers along the edge of her breast. "They're so soft..."
"I try." Jesse shrugged as Bobby was leaning further forward, and he fell heavily onto her. While Jesse could easily have carried his weight, Bobby landed in a rather awkward position. One hand past her head, with all of his weight on the couch; the other hand around her breast; worst of all, he'd fallen almost perfectly on top of her. His own cock had become excited without him realizing it, and it was against Jesse's, though they had their shorts between them to act as a barrier. Their faces were very close, nearly touching. "Are-- are you okay?" Jesse asked.
Bobby pressed his lips against hers for a moment, then parted. "I'm very okay."
"I thought you didn't want to be with a boy?" Jesse asked, checking that Bobby was certain of this decision.
Bobby reached down past the shorts, taking hold of his new friend's shaft. He gave it a few strokes, and saw the breathy near-moans it brought. "I don't wanna be with a boy. They're hairy, and annoying, and they tend to beat me up. You're none of those things." Bobby kissed Jesse again, and the pair wriggled from the couch onto the floor, not wanting to risk falling. As they went, the workout shorts were carelessly kicked into the growing pile of clothes. Their shafts were actually touching now, and it felt so good.
Jesse pushed Bobby off of her, "Do me a favor and stand up." She instructed. Jesse bent over in front of him.
Her ass was fully exposed, and her balls were hanging there. Even her rigid cock was dangling within view. Yet Bobby could only think to say, "What am I supposed to do?"
"You have a cock, a mouth, and ten fingers; get creative!" Jesse yelled enthusiastically. Almost immediately, she felt the boy's hands on the cheeks of her ass. Bobby was obviously still nervous about all of this, but he still extended his tongue, running it along the tight little ring of her asshole. Jesse moaned into the carpet, "That's it, Bobby! Make me your dirty anal slut!" She couldn't help taking her cock in one hand, and her breast in the other. Bobby was still tasting her from behind, his tongue now actually inside her, and tasting the pink flesh within. "Oh, god! I think I'm gonna--"
As she said it, Bobby flipped her over. It was kind of impressive, considering the difference in their size. Jesse let herself climax, spraying the semen all over her smooth belly. Bobby got on all fours and licked her clean, even sucking the last few drops from her now-flaccid member.
"Bobby, do you wanna fuck my ass?" Jesse asked, her soft expression returning as the post-orgasm haze slowly lifted.
"Sure." Bobby seemed eager, but Jesse grabbed his cock instead.
"I still want to train you, just like before. The only difference is, now there's a whole new set of rewards on the table." Jesse touched her hand to Bobby's cock. "Sound good?"
"The training sounds fine, but shouldn't we talk about everything that just happened? Like the fact that you just had sex with a student." Bobby mentioned.
"I won't tell anyone if you don't." Jesse gave him a wink, hand still where it was before.
"Alright. Let's keep it up." Bobby smiled at her.
- 1
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My New Coach, Jesse