This story contains characters over 18 years old and some hate speech. Please enjoy and stop by my profile for similar stories.
Favors: Part 1 Quarantine
"Dad, I promise i will get the money. I know, I should've learned last time. You know i'm good for it. I'll pay him back." Josh explained to his father. I often was involved in these talks over the years. Most of the time it was a "Yeah, dad i'm at Ash's house." in some form or another. I hated it when I was put in charge of my best friend.
I was raised in a 2 parent household. Both parents were loving and privacy allowing. I enjoyed living with them. They made me feel like i was a renter there especially when they made me pay rent for my room and utilities. I could brag to my cousin that i was an adult finally even though i didn't really have my own place. They had a nice swimming pool in the backyard that I've rarely used.
My best friend, Josh, is the typical straight white male enrolled in sports and was actually good at them. The one girl he has ever dated lasted 4 years and they recently broke up to explore other avenues in college. I was sorta jealous of him. Already lost his virginity to a hot girl, even though his break up is fresh at least he had one.
Josh was 6'2" and his muscles made him look like he was 28. He was only 18 and he'd been gambling to other classmates and coworkers on whatever he thought would get him more money. He was only 6 months older than me and yet he's not the brightest bulb in the batch. "Hey, man. My dad is being an ass again. I need to raise money. Got any ideas this time?" Josh asked.
"Onlyfans." I said. He scoffed at it searching on his phone how to get money fast. Being 5'7" and narrow waisted with birth giving hips, i could see that outcome would help us both. But neither he nor I were gay. I got up from my spot on the couch to get glass of water. My outfit today was a thin white wife beater tank top and thin silky basketball shorts. Which didn't hide the fact that i had a firm plump ass. My torso had always been slim and somewhat toned but my breasts were abnormally thick probably from a soy food diet and lack of push ups-i dont know.
"Bro! Why, are you so thicc." Josh moaned. I giggled. Since we were little he always said i had a girl butt. He's tried to grab it and slap it whenever he could but only when we were alone.
"Idk what you're talking about, bro." I teased. It must have hit him then.
"I need your help to get money to pay off my debt, bro." He belted out. I know how much pride it cost him to say that. But why me...why not a girl from school or from another state. "You're right. We need to make an OF together!"
"Why me?" I asked blushing. Coming back into the living room with the water.
"Because you're my friend. And it can earn you some money too. I read on reddit that femboys are the new craze and well... you're pretty femme." He elaborated. I was blown away and distracted that i didn't see where i was going and tripped over the coffee table making the cold water splash on my chest soaking it. I yelped and picked up my foot causing me to lose balance and fall back into Josh's lap. He tried catching me.
"Hehe sorry, bro." I smiled faintly.
"Get off of me, dude." Josh stated. I did and turned to him. My soaked shirt became see thru and my big aureolas were visible. "Bro, it looks like you have tits."
"Shut up, i do not." I stammered.
"Remember when you dressed up as a girl last halloween? If you could learn how to dress like a girl more often and we just put you on OF when you do we'd be rich!" He offered. The silence was deafening. I was searching his fuzzy bootstrap beard wearing, brown goofy eyed, muscle having-
"That sounds gay." I blurted.
His shoulders collapsed in defeat. "Well, I guess I'll ask another girl." I felt the guy's vibe sink and it made my own follow.
"Fine. But how do we do this?" I uttered.
"You really want to do it?" Josh asked. "Cuz you don't have to, just on my account."
"You're a friend. And besides you're the only connection i have to the outside. This lockdown has been nuts." I replied.
"Ok, let me go home and get a couple things. But uh, while i'm gathering things you should make sure you don't have any body hair and uh wash up." He instructed. And he left. He lives two doors down since we were kids which is part of the reason we became friends. I stepped into the shower and washed my body, thinking how am I femme? Is it my girlie breasts, my hips, or my face? I wear my brown hair to my shoulders, so maybe i can frame my hair to fit my face. Shaving my legs and ass and treasure trail and armpits. I didn't want to look girly but since I havent went to school or left the house really, would it be so bad. Plus, i know it's been at least seven months for Josh. It's probably because he just wants to get off and i'm femme enough. yeah, thats it.
"I don't know how to act like a girl at all anyways." I said brushing my hair. I borrowed some femme deodorant and perfumes to stash them in my room. I put on my boxers and with impeccable timing Josh burst thru the door.
"Hey! I tried finding my sisters clothes but I just found a few items before she got home." He was out of breath which explains why he was so fast. He pulled out a few items from his backpack. I went thru them then my eyes came across something.
"A pink two piece bikini?" I shouted holding them in my hands. Why am i hard suddenly.
"Yeah, I guess. I know you have a pool and you said your parents aren't back til next week. So we can have a day at the pool kind of vibe." Josh said. "Go ahead and try it on." At this point I knew i wouldn't look good wearing this stuff. But his hot sister wore this and i wanted to put it on just for that fact. I put on the top piece of the bikini and Josh's eyes lit up and almost bugged out. Somehow the bikini not only fit but it pushed my breast together making a soft cleavage look. "Bro, you have to complete the outfit right now. I'm gonna look up make up videos on youtube."
I turned away from him and slipped my boxers off and pulled the bottoms on. They fit and the thong piece set perfectly in my cheeks. If i'm being honest with myself the outfit made me feel girlie. "I don't know, man. Is this really okay?" I turned toward him. And he was literally drooling. Yep, he definitely needed to get laid.
"Your body was made to look like a femboy." He ran out of my room and in a couple minutes came back holding make up utensils. "Here put this stuff on and meet me outside!
I put on some mascara and lipstick looking at myself in the mirror being turned into a female type persona. I liked the taboo and I might be conceited because i wanted to fuck the chick looking back at me. I finished and met him by my pool in just my- his sisters- bikini. Being in public in just a two piece was different than being in costume and in public, I liked it. As soon as i stepped out on the deck I noticed that Josh was in his boxers and just standing by the pool. "How do I look?" I asked.
