Adam Loses a Bet Ch. 01

The last fall leaf fell to the ground as I packed up the last of my books into a cardboard box. I never read any of them, but my mom was adamant that I keep each one. Due to financial troubles, our packing and moving was delayed; we were moving to Seattle in the November chill. My little sister and I were the only two kids of a single mom. She's a hardworking, honest person, who never talks about her own problems. Everything's fine.

My name is Adam. I'm 5'5, I have long dirty blond hair, and can't grow a beard for the life of me. I often tie my hair into a man bun or just let it go wild. My mom likes my hair long; long hair means less on haircuts and hair product.

We weren't moving into the ghetto, but we definitely weren't going to a nice part of town. The school was old, and the sidewalks were cracked, but it was cheap, and we had family nearby. That was the only appeal to me, family. I was leaving my only 2 friends I had ever had back in Boise, and I wasn't as optimistic about my future social life. It was going to be rough.... or that's what I thought. That was all I thought about over the next two weeks.

After a million headaches, we finally made it too our new home. When I first saw my room, I cringed at the hot pink walls and all white furnishings. My sister was in a similar room but was substantially more excited. I never liked girly things. Ever since 1st grade I avoided them like the plague. This was probably to avoid getting laughed at, or something close to it.

Moving past the color, my room wasn't half bad. Lots of dresser space, a full-size mirror, and a personal bathroom. Well, if by personal you mean shared with your little sister; it was placed as a hallway between our rooms, with locks on both doors. As I looked out my window into the distant wall of the adjacent house, a glimmer of hope showed in my eye. "Everything's going to work out," I rationalized. If only I knew how wrong I was.

The next day I woke up early. I took extra time to wash my hair, brush my perfect teeth, and pick out my clothes. I drove to school both nervous and excited. I don't remember a single thing taught that day. But I remember the most important things. There's a cute girl named Amy that sits next to me in biology and a fitness club that's guy exclusive. I really needed friends, and what's more manly then fitness. I found a poster with a signup sheet. As I signed up, I was approached by a member. He was easily over 6', and obviously knew his way around a gym. He had brown hair, a sturdy face, and surprisingly kind eyes. Regardless, I was intimidated by his towering confidence. "What are you doing," he challenged.

"I'm signing up for 100x fitness club."

"Are you sure, it's rough."

"Yeah, I'm sure! I'm a pretty fast runner."

He looked me up and down, pausing halfway through. "What's your schedule like?" Almost instantly I responded, "I'm free anytime; I don't have anything after school, and I'm down for anything!"

"Anything?" he questioned.

"Anything."

He paused to think, "First meet is today after school, room 405."

"I'm there." That was an exciting exchange, maybe there's hope for my social life after all. The last bell couldn't ring any faster. The moment it finally rang I zipped out of class and started towards 405. After a few wrong rooms and a very helpful janitor I found the room. I stepped inside to see a decent amount of people. I joined the mass as I found a seat. Almost like clockwork, the meeting started right when I sat down. All our attention was turned to a harsh slap of a ruler. Looking up, the source was the same member I had talked to earlier. He began to yell, "My name is David, and I started this club. Let me be clear. This club only exists so we can have a room to ourselves for sluffing, or whatever we want. If you want to use the room during the weekend or on Tuesdays, you need to do 100 reps of any workout every day. Pushups, Sit-ups, Pullups, etc. If any of you tell a teacher or admin about anything that happens in this room, there will be consequences. Severe consequences. A tall dark and handsome guy stood up, "I'm Andrew, club president. If anyone needs workout advice, come talk to me, I'll take care of you." David cut in harshly. "Any questions!?" A cold silence filled the room. After a painful moment, a tired looking man raise his hand and said, "how will you know if we do our daily workout." David seemingly ran towards him and stretched out his arm. A crisp slap made everyone jump. The victim was knocked to the floor hard. He yelled, "you will never lie about that! We have an honor code. If we catch you lying in a spot check, you'll wish you were never born." Everyone got uneasy at the sudden intensity. 3 people got up and left. Following, Andrew stood and scoffed, "the weak are gone, everyone signs the disclaimer upfront and leave."

Everyone signed the short form and started to leave.

Just before I left Andrew called me out. He motioned for me to come over, and I slowly made my way over to him. He looked down on me. I thought I was going to be beat up or worse. Unexpectedly, his eyes softened, and he said, "Sorry about that first impression, you can call me Drew." He held out his hand invitingly. This threw me off; I didn't know what to do. I meekly shook his hand and introduced myself. His grip was stronger than my flimsy handshake. He looked at me compassionately and reassured, "I think we're going to be great friends. David was telling me about you. Did you really say you were willing to do anything?"

"Yep! I'm a fast learner and I love to run."

"Could you commit to 100 squats a day?"

"Easy. Is that all?" Drew paused in thought. "How about you try 200 and work your way up more by the end of the year." I immediately regretted trying to initially seem cool. Was that even possible? I wasn't in bad shape, but I definitely wasn't super impressive. Most of my fat collected in my thighs and butt, but I was still definitely skinny. All this doubt ran laps in my head while my mouth moved in rebellion. "Of course!" The voice in my head consequently screamed 'Why did I say that!!! That a lot of work!' A smirk appeared on Drew's face as David walk up. He snapped me out of my internal regret, "do you want to come by my place later and play some call of duty?"

"YES!"

"Cool, Drew and Bryan will be there to. Just make sure to do your squats before you come over." All my optimism and nerves were replaced in an instant with joy and relief. We exchanged numbers and I drove home a successful man.

Later that night at 6, I drove up to David's house. My legs were a little sore from doing squats, but I did them! I had to split them up into 4 groups of 50, but I did them. He lived roughly 10 minutes away from me in a nicer part of town. His house was huge; it had 2 floors and a swimming pool. When I rang the doorbell, I was greeted by a somewhat overweight black guy in expensive sweatpants and a generic Jersey. "Hi, I'm Bryan, you must be Adam."

"Yep, in the flesh."

"Cool, come downstairs we're just getting started." As I followed him downstairs, I noticed a lot of empty rooms. They were bare of furniture, pictures, and sometimes even paint. The basement was easily the nicest place in the building. It had a large 4k flat screen a two-person couch and an armchair.

David greeted me, "Aaaaayyyee, Adam's here! get him a controller." I was handed a controller and sat on the floor leaning against the couch. Nothing weird happened that night. Except I think David was playing with my long hair behind my back. We played until it was late, and then we all left.

I had done it. I had friends, my mom found a second job, my sister was always off on sleepovers, and my classes seemed easy, so everything was looking up. We followed a similar routine for the next month. We would go to school, play video games, talk about girls, sleep, repeat. It was just what I wanted. The only problem I had was how hard squats were. David taught me a few other workouts that would strengthen my glutes, thighs, and hips separately. He said they would help me with my squats for sure. The only problem I had was that I had to use machine in the unofficial girl's section of the school gym for some of David's workouts. Which was a little embarrassing, but the gym was mostly empty all the time. I could now do almost 130 squats without stopping. Everything was right and I was happy. I could count this as one of the best months of my whole life.

One day, while we were gaming, everything changed.

We had started making bets on games weeks ago. It typically would result in licking something gross, getting a handicap on the next game, or tell an embarrassing secret. But today Bryan brought a surprise.

"Yo! Check out what I found left in room 405," He said as he threw a black blob into the middle of the room. Since I was sitting on the floor anyway, I picked it up for everyone to see. They were a pair of distressed black booty shorts. Pretending to be disgusted by them I threw them at David. "Eww. I don't know where those have been," I said with disdain. David threw them back on the floor, and we moved on. Less than half an hour later they came up again. "You know Adam... I think those would fit you," Drew suggested.

"Yeah, never in a million years."

"Aren't you willing to do anything?"

"..."

"If you lose this round you have to put them on, deal?"

After a moment if thought I replied, "Deal." We were playing halo at the time, and I was obviously significantly ahead. No chance I was going to lose. However, all three of them exchanged a glance and leaned forward, clearly more focused. David camped right outside my zone and didn't let me out while Drew kept giving Bryan free kills. Quickly I went from undefeatable to in trouble. This went on till Bryan pulled ahead. I finally got around David and went right towards Drew for a shot at stopping him. Unfortunately, I was too slow, and time ran out. The screen went black and Bryan's character appeared on the win screen.

Everyone except for me went wild. After congratulatory high fives, the shorts were thrown my way. "Really, do I have to," I pled, "I don't even think they'll fit, they're shorter than my boxers." hearing that, David ran upstairs. After a moment of confusion, we heard him slam a door and run back down. "My mom works theater and keeps loads of costumes in our empty rooms. There's a few complete wardrobes just upstairs." He threw me a scrunched-up ball. I didn't even look at it. I begrudgingly walked into a nearby bathroom and locked the door. I unfolded the ball to find white cotton panties. I scoffed in disgust and threw them to the other side of the room.

After taking off my pants I held up the shorts to my waist. They seemed a little small but had some stretch to them. I slipped them up my legs and squeezed them over my butt. I was wearing a thrasher shirt that was a little small for me, so you could clearly see a little midriff. Normally I would just wear my pants high. I couldn't do that with these. I think the shorts were boostey because they gave me subtle curves. I never wore particularly tight clothes, so I never looked. My legs were like my face, hairless and smooth. Since I had bad eating habits, I never got definition from leg workouts, which were all I did. I had particularly thick thighs and a big-ish butt. David once pointed it out at the gym. He said girls like ours as much as we like there's, so I wore it like a badge of honor. The shorts showed patches of boxer all up the side. Additionally, a little flared out at the bottom. I rolled my eyes and relented. I stripped and walked to the other side of the bathroom.

Picking up the panties was weird. Stepping into them was weirder. Feeling the soft material run up my leg and around my waist was the weirdest. I wasn't exactly well endowed and was always too embarrassed to measure. My little member tucked in nicely to the delicate fabric. I looked into the mirror. They fit me perfectly, and really made my legs look... never mind. Feeling a need to hide my shoulder length hair, I tied it up and spun it into a man bun. I slipped the shorts back on a walked to the door. After a deep breath or two I opened the door and walked out. I was greeted with whistles, catcalls, and applause. My cheeks felt like fire. I quickly sat down, eager to move past this. "Do a little strut," David egged on.

"No way José, I can't even believe you convinced me to do this."

"Ahhh, come on. What's the big deal? it's just like walking."

"Whatever, let's just start the game." I stared at the motionless images on the screen. "We're waiting," David mused. After a deep throated scoff, I stood up and walked into the bathroom. I pulled my long white socks to just below my knee, of course to cover as much skin as possible. I heard music coming from the TV and knew that was my que. I threw open the door and started walking towards the couch. I swayed my hips like I had seen done in the movies. I don't know what possessed me, but when I was a foot away from the guys, I struck a pose. I pulled out my bun into a ponytail as I turned around. I stuck my butt out, pouted, brought my finger to the bottom on my mouth, and looked pleadingly at David. I then made my way back to the bathroom leaving a standing ovation behind. If I'm being completely honest... I was A LITTLE aroused and I don't know why.

I quickly sat down in my normal spot on the floor and we had fun like nothing had ever happened.

Roughly an hour later, we took a break. I started towards the bathroom to change out of the booty shorts, but Bryan stopped me. "What are you doing?" He questioned.

"I'm changing out of these; it's been a hot sec to long."

"No, no, no, the bet was a full day deal. You have to wear them all night."

"Woah, woah, woah, that's pushing it."

"Aren't you down for anything?"

"Yeah, it's just not a big deal if I take them off, right?"

"If it's not a big deal, then you won't mind keeping them on."

"Yeah but..."

"Do you want to go double or nothing?" I thought about that for a minute. "Sure; Easy!" I said with a fake confidence.

"Dope, we'll 1v1 after we eat."

Half an hour and 2 delivered pizzas later we were ready to rumble. I really got into this match. My palms were sweaty, my brain was running at a million miles an hour. I was slightly losing but I knew I could turn it around. I leaned closer to the T.V. and slightly stuck out my tongue. What I wasn't conscious of, my panties were tempting the eyes of everyone behind me. The guys leaned in. "He actually put them on," Andrew pointed out to David.

"I knew he would. Heck they look kind of good on him" David replied.

"Thanks for the view Adam!" It was at the point that I understood what they were talking about. I quickly sat up straight and pulled the shorts the little higher they could go. At that moment Bryan did a risky move and took the match. I couldn't stop looking at the win screen. Everyone burst out laughing... but me. "Have fun tomorrow, Bryan teased, "school's going to be such a ball."

"Wait. School?"

"Yeah, it's an all-day deal Adam." My world seemed both small and in danger. Why didn't I think of school?! I generally had spotless integrity, but this made me question myself. "Guys, I can't wear this to school! I'll be a laughingstock," I tried to reason.

"Well you made the bet, not me" responded David. A clear look of dismay toke over my entire person. An awkward silence filled the room...

...

*cough* *cough*

....

....

David interrupted the silence, "How about this, rather than booty shorts all day tomorrow, a full ensemble after school the rest of the week." Almost without any thought I quickly agreed. A terrible habit of mine.

The rest of the night was pretty normal, Outside of my clothes. Sure, there was a little teasing here or there, but that was to be expected. I drove home in my normal clothes, did math homework and slept like a baby.