Study Buddies

I've been working on several different stories at once, and just finished this one, which is one of three I'm working on about being feminized. Hopefully more to follow soon. Standard disclaimer, all characters portrayed are age 18 years or older.

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THWAP! The towel snapped against my bare ass cheek like a firecracker.

"Ouch!" I yelped in a surprised, shrill tone. I instinctively placed my hand against the spot where I felt the sharp pain, I could still feel my fleshy right ass cheek still jiggling from the impact.

I glared up at the three members of the varsity baseball team who had just come into the locker room to find me changing after gym class. One of them still clutched a gym towel in his hand like a whip. As they laughed and ogled my naked rump, I quickly finished pulling up my boxer shorts and jeans.

"Damn, Casey!" The oaf with the towel said. "Not only do you look like a girl, you sound like one too!"

This elicited a fresh round of laughter from the three of them. It always did, ever since freshman year when Billy Douglass -- then a popular sophomore on the football team -- came into the locker room after gym and remarked loud enough for every other guy in class to hear that I had a "bangin' ass."

Now, I was a senior, and after four years of being made fun of by the jocks about my admittedly girlish figure, graduation could not come quick enough. Three more weeks, I muttered under my breath as I zipped up my jeans.

"Hey!" A fourth, familiar, voice came shouting into the locker room. "Leave Casey alone."

That was when I caught the eye of Derek Taylor as he marched into the locker room. Like me, Derek was a senior, and we grew up a few houses down from each other. Unfortunately, the list similarities ended there.

A quick way to describe Derek would be to say that he was everything that I was not. Captain of the baseball team, he was tall, a few inches over six feet, and had the type of ripped, muscular build that girls and moms alike must picture in their minds when they masturbate. Suffice to say, he had no problem getting laid, or so I'd heard. It seemed like he was talking to a new girl every week.

"Sorry about them, Casey." Derek said as he walked towards me. "They're animals."

As he passed behind me, he put a hand on my shoulder and gave it a gentle squeeze. It was a familiar gesture, he'd done it a dozen times over the years in situations just like this, when he'd walked into the locker room or the lunch room and found someone picking on me. He'd tell whoever it was to back off -- which was generally enough -- and then he'd give me a possessive squeeze on the shoulder as if to say 'he's mine, don't fuck with him.'

Derek and I weren't friends, really, but he'd always been nice to me and he always stuck up for me. Like most high schools, bullying was commonplace at ours, and I was commonly the recipient of it.

Sometimes they teased me about my size, at 5'5" tall and 130 lbs I was one of the smallest kids in school. Other times, they teased me about being a nerd; aside from having a perfect GPA I was also on the debate team, the math team, and the chess team. Most of the time, however, they teased me about the same thing those three assholes cackled about after whipping me with a towel.

I have a...I guess some might say...thick ass. I don't just mean that I have some junk in the trunk. Beyond the bare minimum of physical fitness required to pass gym class, my workout regimen was non existent, so, yes I did have some junk in my trunk. But it was more my... I guess you'd call it my shapeliness that caught the attention of the bullies and jocks.

As much as I tried to hide it by wearing intentionally large and baggy jeans and t-shirts, I had a perfectly round, thick, pear-shaped butt that most girls would be jealous of. Also, I was scrawny up top and slender at the waist, giving me the appearance of lady-like hips. Finally, I had practically zero natural body hair except for my pubes and a fine, almost invisible coat of hair on my legs and chest.

Ever since I made that first freshman-year mistake of stripping down for gym in front of Billy Douglass, my ass had gotten me plenty of attention. Unfortunately, it was the exact opposite kind of attention I desperately wanted. It was perhaps my greatest disappointment that addition to being an effeminate nerd loser, I was also a virgin.

And I don't just mean that in the strictest sense of the word. The truth was, I was a high school senior, three months past my 18th birthday, who had never so much as kissed a girl. It's not that I wasn't into girls, I very much was. I'd spent lots of time thinking about girls, had a few crushes, and even once came close to kissing Becky Stevenson before I panicked and walked away. Alas, the only lover I'd known in my life was my own right hand.

Everything would be different in college, I told myself. Once I got to the big State University -- where I'd gotten a full-ride academic scholarship -- with an almost infinitely larger student body, I would find somewhere to fit in. I would find something to be popular for. And, most importantly, I would find someone to fuck me.

Two more weeks, I muttered under my breath as Derek and the other three jocks left me alone in the locker room. Only two weeks of school left, and then I was off to be the man I was meant to be.

_______________________________________

"What a bunch of jerks." Scott huffed as we sat across from one another at the lunch table later that day.

Scott Connors was my best friend. Well... he was kind of my only friend. I met Scott freshman year on the first day of Chess Club and we hit it off pretty much immediately. Kindred spirits, Scott and I were two hopeless nerds desperate for female attention.

Though he was also a massive brain like me, Scott looked more like a wrestler or a football player. He was taller than me, which isn't saying much, just under 6'. He was also heavier. When we met, Scott was a full-on pudgy kid, but in the past few years he'd taken up going to the gym and managed to thin out a bit and now only carried a few extra pounds around his mid-section.

"I've been trying to get you to come work out with me." Scott said, taking a bite of his sandwich. I had just described my humiliating encounter in the locker room.

"Why?" I asked. "It's not like I'm going to bulk up instantly and be able to defend myself."

"True." Scott shrugged. "But if you put on some muscle you might look a little less like a girl."

"Once we're at college it won't matter." I assured Scott. "The university is huge, there will be no shortage of women for us."

Like me, Scott had also gotten a scholarship at the state university. In fact, we'd gotten our acceptance letters on the same day and had made it the plan that we would room together. Ever since then, our focus had shifted away from trying to get laid in high school, to dreaming about how we'd get laid at college.

"I've been thinking." Scott said, putting down the crust of his sandwich. "We've been so confident that we are miraculously going to be having sex with women once we set foot on campus."

"Because we will." I scoffed.

"Maybe." He said. "But, we've all but given up hope of losing our virginity in high school. Don't you think we should at least try to do that before we graduate? If college really is going to be a wonderland of sexual activity, it would be good to go in at least knowing what we're doing. Don't you think?"

I had to admit, he had a point. I knew very well from my own handful of near-encounters with women over the past four years how quickly the panic of inexperience sets in and ruins everything. I still cringed at night when trying to fall asleep and the memory of running away from Becky like a little bitch flashed across my mind.

"You're not wrong." I agreed. "But there's only a couple weeks left of school. How the hell are we going to accomplish in two weeks what we haven't been able to do in four years?"

"I'm just saying." Scott said. "We should at least give it a real try and not just throw in the towel. Maybe there are two girls somewhere in this school who are just as eager as we are to gain some experience before heading off to college."

"Like who?" I asked, skeptically.

Together, we scanned the crowded lunch room for any sign of a pair of such desperately horny females as Scott described.

"What about Janet Armstrong?" I asked as my eyes landed on the large, cherubic form of one of our fellow Chess Club members across the room.

"She'll crush you under her weight." Scott said.

"Don't be a dick." I chastised him. While Janet was admittedly fat, we both knew what being bullied felt like and I tried to avoid doing it to others as much as possible. "And I didn't mean for me, I meant for you."

"You want me to fuck Janet?" Scott said incredulously. "Big ole Janet?"

"You're big." I pointed out. "I know you think you're this big hunk now that you lost a few pounds, but you're still a chubby kid at heart."

"I mean..." Scott said, and I could see him reconsidering as he eyed Janet across the way. "She does have some big tits."

It was just at that moment that Janet turned and caught us both staring at her. Immediately, she lit up into a big smile and waved at Scott.

"Look at that, she's into you." I said, egging Scott on. "I'd say it's a done deal. Get to work on her."

"Okay." Scott shrugged. "Maybe you're right. Maybe I could fuck Janet. But what about you?"

Unfortunately, this was a much harder issue to solve. Whereas Scott was just as much of a nerd as me, he was at least tall and big, which was enough for some girls. No girls went for short and scrawny with a nice fat peach ass.

"I don't know." I sighed.

"What about Becky Stevenson?" Scott offered. "She was into you for a while. Didn't you almost make out with her?"

"Almost." I said. "Before I pussed out and ran way like a child."

"Maybe you can salvage that?" Scott said. "She's probably your best bet."

"Yea." I said, trying not to sound as defeated as I felt. "I'll think about it."

_______________________________________

"Hey Casey," I heard Derek's voice for the second time that day as I was walking home from school. "You need a lift?"

I turned to see Derek creeping along side of me in his jeep. Lots of kids in school drove their own cars to school, but not me. Honestly, I didn't need one. The neighborhood Derek and I lived in was walking distance from school, and I didn't mind the walk.

"It's cool." I said with a wave. "Thanks, though."

"Come on." He said with a bit of finality, like he'd already decided for me. "Get in."

He stopped the jeep and I climbed up into the passenger's seat. Once I had my seatbelt on, he sped off down the street towards my house. He didn't say anything along the five minute ride, just masterfully worked the stick shift with his strong, hairy arm and masculine hand. I remember watching his hand work the knob and thinking of all the girl's bodies he'd touched with it, and how much pleasure he must have brought them.

"Listen." He finally spoke when he pulled to a stop in front of my house. "I have a huge favor to ask you."

"From me?" I froze halfway out the car door.

"Yea." He said, then placed his hand on my thigh as if to hold me in my seat. "I need your help."

Even after I settled back in my seat to hear him out, he kept his hand on my leg just above the knee. It struck me as a bit awkward, and the longer it rested there the hotter I could feel the heat of his palm against my fleshy thigh beneath my jeans.

"What do you need?" I asked.

"You took Mrs. D'Angelo's calculus class, right?" He asked, looking me in the eye.

"Yea." I said, shifting my gaze away from his direct stare. For some reason, the way he looked at me made me feel exposed, seen, observed. "I had it last year. I got an A."

"Of course you did." Derek said with a laugh. "That's why I need you."

"I'm not going to help you cheat." I said, swallowing hard as I thought I'd figured out what he wanted.

"No, no, I don't want that." He shook his head. "I just need you to tutor me. If I don't get an A on the final exam next week, I'm not going to pass the class. And if I don't pass this class..."

He let the rest of his sentence hang in the air.

"You'll lose your scholarship." I said, remembering that Derek had gotten an athletic scholarship to a Division 1 school.

"Yea." He said matter-of-factly. "So, what do you say, Casey?"

I took a moment to try to think of a good reason to say no. Truthfully, I didn't really have a good reason not to tutor Derek, other than I didn't really want to. I needed to focus on trying to lose my virginity. I quickly felt pangs of guilt about this, though, as I thought about all those times he stood up for me when I was getting picked on.

On top of that, another very good reason to help Derek out popped into my mind at that moment.

"Okay." I said. "But you have to help me in return."

"Help you?" He furrowed his brow. "Sure, with what?"

"You have to get me laid." I said.

He laughed. "I can't get you laid, Casey. Girls don't just do whatever I say."

"Sure seems like they do." I joked.

"Funny." He said, and then chewed his lip as he thought of something. Then, a big smile crept across his face. "I'll tell you what. Maybe I can get you laid, maybe I can't, but what I can do is coach you."

"Coach me?"

"Yea." He said. "You tutor me, and I can teach you everything I know about getting with girls. Hopefully, by next week I'll be passing calc and you'll be getting yourself laid."

"That's a deal!" I said and reached down to squeeze his hand where it sat on my thigh.

In response, he squeezed my thigh. I would have been too embarrassed at the time to admit that this sent a little chill of excitement up my leg. I'd never had anyone touch me like that, guy or girl.

"Awesome." Derek said with a smile. "So, can we start tomorrow after school?"

As I walked away from Derek's jeep towards my house, a renewed sense of hope crept over me. Like Scott said, I had all but given up hope at getting laid in high school. However, with someone like Derek coaching me on how to get it done, I might actually have a shot. Maybe Scott was right, maybe we did have a chance.

Just before I went in the front door of my house, I turned to glance back over my shoulder at Derek sitting in his jeep watching me. He smiled and waved, and a gave him a little wave in return before going inside.

That night, I sent Scott a text to tell him about my tutoring exchange with Derek.

"That's awesome!" Scott replied. "If a guy like Derek can't help you get laid, then no one can."

"Lol." I wrote back, trembling with excitement at the promise of sexual fulfillment that lay ahead.

"Maybe you can show me a thing to two." Scott wrote. "Help me out with a few pointers."

"Maybe." I wrote back.

___________________________________

Derek also gave me a ride home in his jeep after school the next day, only this time we went to his house so I could walk him through the first few chapters he needed to know for the calculus exam.

At first, he didn't really seem to be able to grasp any of the concepts and I worried that helping Derek get an A might be a taller task than I'd anticipated. After a couple hours, though, things finally started to click and he was able to complete the set of practice problems with only a few mistakes.

"That's enough for today." I said after I finished reviewing his work, making marks with a red pen where ever there were errors like I was his teacher. "You won't remember any of this if you try to cram it in."

"Fine with me." Derek said, standing up from the kitchen table to stretch. "My brain hurts. You want a beer?"

"A beer?" I wasn't sure I'd heard him correctly.

"Yea, I like to reward myself with a beer after a hard practice." He said. "You drink beer, don't you?"

"Absolutely." I lied, I'd never had a beer in my life before that.

Derek grabbed two cans of beer from the fridge, cracked them both open, and handed me one.

"Your parents don't care that you drink?" I asked, trying not to grimace at my first sip of the bitter ale.

"Not if I do it at home." He said. "They're realists, they know I'm going to drink regardless of what they say. So, they just want me to be safe."

"That makes sense." I said, gulping down more of the frosty beer and immediately feeling the effects as my brain and limbs buzzed.

"Okay, now it's your turn." Derek said.

"My turn?"

"Time for your first lesson." He said, then walked out of the kitchen. "Come on."

I took my beer and followed him upstairs and into a bedroom at the end the end of the hall. He opened the door and we walked into a large room with purple walls and a collage of boy-band posters over the bed.

"This isn't your room." I laughed, feeling a little tipsy.

"No." Derek chuckled. "My older sister's room. She's away at college."

"Oh." I said. "What are we doing in here?''

"Lesson one." Derek said, and shut the door, locking us in the girly room. "If you want to get laid, you need to think like a girl. And if you want to think like a girl, you need to understand girls. How they think, what the feel, why and how they do the things they do."

"I see." I said, not really sure I was following. But, Derek was an expert in the opposite sex as far as I was concerned, so I trusted him.

"Here." He said, and crossed over to the dresser.

He opened the top drawer and rifled through piles of pink and purple, lace and frills. Finally, he pulled something pink from the drawer and tossed it to me. I almost dropped my beer trying to catch it, but when I did and I held up whatever it was, I saw that it was a bra. Pink lace.

"What am I supposed to do with this?" I asked, laughing. It was the first bra I'd ever touched, and just the sight of it sent blood rushing into my cock. Must be the beer, I thought, because I was suddenly very horny.

"Put it on." Derek said.

"Yea, right." I laughed.

"I'm not joking." He said, and looked at me with a serious intent.

"Really?" I asked. "Why?"

"Like I said." Derek explained. "You need to understand girls. How best to understand them than to do what they do?"

"But how will putting on a bra help me..." I started, but Derek interrupted me.

"Just do it." He said sternly, and I could tell he was losing patience.

Without another thought, I put my beer down and fumbled with the bra, examining it. Trying to make sense of how it should go. I located the two shoulder straps and started to slide my arms through.

"Wait." Derek waved at me to stop. "Here, you need to take your shirt off first."

"Oh." I said, thinking this made sense. "Okay."

So, I pulled my t-shirt off over my head and dropped it to the floor, so that I was shirtless and feeling a little exposed in front of Derek. He watched me as I slid my arms through the two straps and pulled the garment tight against my chest. I looked down, seeing the pink, lacy cups settle against my small, pudgy pecs, covering my nipples.

"I'll help you with that." Derek said, and went around behind me to clasp the bra around my torso.

As he did so, I felt the bra tighten around my ribs, and the cups suctioned to my chest. Then, I felt Derek's hands on the skin of my shoulders as he adjusted the straps. I shivered as he first touched me, but then took a deep breath. I was lucky to have him helping me, I thought, I never would have thought to try this on my own.

"It fits you pretty well." Derek said as he came back around to face me. "It even looks like you have some perky little tits. My sister's tits are small, so it looks perfect on you."

"Thanks." I said, and felt my cheeks get warm. Then, I realized I'd actually thanked him for his compliment. "I don't mean thanks, I mean... thanks for helping me. You know, with getting laid."