We’d barely been home a week from vacation when my father said the worst, cruelest, most unfathomable thing in the world to me.
“Son,” he said, hands on his hips like some dumbass, hefty cowboy, “it’s time for you to get a job.”
I almost screamed.
Okay, I did scream a little bit. I also tried to slam my bedroom door in his face, but he caught it with the toe of his work boots.
“I’m serious,” he said, wedging his way past the door and into my room. “Now that you’ve graduated high school, you need to start earning money to support yourself.”
I was hardly able to stop him from coming into my room, weak and lanky as I’ve always been. So I sat on the opposite side of my bed, facing the wall and pretending not to hear him.
“Look at me.” I felt his warm, thick fingers on my shoulder. Reluctantly, I turned and met his gaze. “Your mother and I are happy to house you while you go to community college. We’re not asking you to pay rent or anything, but you need to earn your own money for other stuff. Food, clothes, all your little accessories.”
I spotted my box of scarves sitting on the ground and subtly kicked it under the bed. “I don’t see why I need a job all of a sudden,” I said with a huff. “You guys were fine paying for me when I was in high school. Now I’m in college and everything’s changed? That’s ridiculous.”
“That was my fault.” Dad sighed. “You’ve always been a… softer boy. I didn’t want to push you too hard, I wanted you to feel supported. Your mother thought I was coddling you, and maybe she was right. But no more–I want you to start looking for a job on Monday.”
“What would I even do?” I said, my voice getting slightly hysterical. “I have no skills.”
“Well–”
“DON’T say retail. I would rather set myself on fire.”
“I wasn’t gonna say that.” Dad gave me a small smile. “I was gonna say, you could always come work for your old man.”
I raised an eyebrow. “Working construction? Seriously?”
“Well, not exactly,” he admitted. “But we could use some more help in the office. Kathy could train you on the front desk, you could answer phones–”
“Hard pass,” I said.
Dad sat next to me on the bed and nudged me playfully with his leg. “You know, I worked for my dad when I was your age. It could be fun.”
He stared at me with those big, dumb, blue eyes of his, face stretched in a stupid, goofy grin. Just who did he think he was?
I walked over to the door and opened it, gesturing for him to leave. “I’ll figure something out on my own, thank you very much.”
Dad nodded. “Sounds good. I know you can do it, son.”
He gave me a hug, pinning me against his thick, beefy chest. I felt his scratchy mustache on my skin as he kissed my cheek and then he was gone, leaving me with a sick feeling of dread in my stomach.
“It’s completely unfair,” I whined, lounging on my stomach on the bed as my BFF Gibby offered words of comfort over the phone. “I mean, talk about moving the goalposts, right?”
“I don’t know,” she said, her voice a slow drawl. “Maybe it’s a good thing. You could save up a lot of money, especially if you don’t have to pay rent.”
“But what would I even do? Be a barista? I know that’s every gay’s calling, but I just can’t picture myself in that green apron and ugly hat.”
“Well,” she said, her voice tinged with the promise of something juicy. “There are other ways of making money.”
“Like what?”
“I may or may not know someone who made a ton of money selling feet pics online earlier this year.”
I sat up, my jaw dropping. “Gibby, you slut!”
She laughed. “You’d be surprised how many pervs are out there!”
“How much did you make?”
“Mmm, I don’t know. Like $20 a photo. Maybe $50 if I did something special like paint my nails or step on a piece of cake.”
I stared at my toes, frowning. “That’s like, nothing. Men are so cheap.”
“I had a lot of guys offer to pay more for more… intimate pics,” she said. “But that kind of weirded me out. It’s one thing to show my feet, but to go full-on sex worker… I don’t know.”
My eyes lit up. “Holy shit. Gibby, you’re a genius.”
“Oh God,” she groaned. “Why do you always take the exact opposite meaning of what I say?”
I giggled, ignoring her. “All this time I’ve been trying to lose my virginity by just giving it away. I’m such a stupid slut! I should be charging guys for the privilege of taking my cherry. I’ll kill two birds with one stone!”
“This sounds like a terrible idea, Leo,” she said, but I had already hung up. I grabbed my computer and googled “Gay Sex Worker Business Near Me High Earnings Hot Guys No Uglies.”
I was surprised at just how many sites there were for gay escorts. I sorted through various profiles, trying to get a sense of what people charged and how it worked. The most popular profiles all had perfect bodies and big muscles, and most of them were tops. There were plenty of twinks and bottoms on there, but they didn’t seem to get nearly as much traction, which worried me. I would do a lot of degrading sex stuff for money, but topping was a step too far.
I woke up the next morning to the sound of my dad banging on my bedroom door.
“Up and at ‘em!” His booming voice made my head throb.
I pulled a pillow over my head, groaning. “You can’t expect me to job search this early.”
“Leo, it’s 11:30. I’m home for my lunch break and thought I’d check on you. Now come on, it’s time to hit the pavement. You can take my car, just drop me off on the way and pick me up at 5.”
I threw on a pair of booty shorts and an oversized sweatshirt, but my dad turned me around and sent me straight back inside. “You need to look presentable,” he said. “That means a collared shirt and a pair of pants.”
I didn’t even know if I had such an ugly combination of clothes, but after a little digging in my closet, I found a floral button-down and a skin-tight pair of Levi’s. When I got to the car, my dad was beaming at me.
“You look great, son. I’d hire you in a heartbeat.”
I rolled my eyes but said nothing. After I dropped him off at work, I headed for the nearest café to do more research into selling my body to strangers online for money. The place was sprawling with people sitting at tables on their laptops, sipping lattes and working remotely. How funny that I was just like them now, in a way.
I set my bag on a table and headed for the counter, where a cute barista with a nametag that read Drew stood smiling at me. “Welcome in,” he said. He had bright white teeth and a wide smile, which stood out against his dark black skin. His hair was thick and textured, jutting out at every angle. He was hot as fuck.
“Hi,” I said, desperately wishing I’d worn the booty shorts. “What’s good here?”
He pursed his lips, then said, “Depends. What do you like?”
“Honestly? Something thick, creamy, hot…”
He grinned. “Like a latte?”
“Ugh, no,” I said. “I hate coffee.”
Drew laughed. “Well, that’s about 90% of what we sell here. But if you like thick and creamy, how about a hot chocolate?”
I stared at his lips, full and beautiful. God, what I wouldn’t give to feel them on my little pink purse. “Let’s do it.”
“Can I get your name?”
“Leo.” I raised an eyebrow. “Why, do you want my number, too?”
His eyes went wide for a second. He opened his mouth, then sputtered. “Um… it’s for the drink,” he said awkwardly. “You know, when we call it out on the end of the bar…”
I felt my stomach drop out of my asshole. “Right. Of course. That was just a joke.”
He smiled. “I mean, I’ll take your number, too.”
I smirked. Looks like this girl’s still got her game.
Once I’d nabbed the hot chocolate (and Drew’s number), I sat down at my table and continued my research.
To be honest, a lot of the escorting websites seemed kind of boring and, frankly, too much work. Selling my body was fine with me, but what I really wanted was a hot older guy to pay me money, give me nice things, and fuck me bareback. It wasn’t until I stumbled on a website for sugar babies/sugar daddies that it all became clear. Of course! This was my lot in life. I don’t know why it took me this long to realize it, but when you find your calling, it’s like everything falls into place.
I signed up for the site right away and started building my profile.
Name: Leo Wyte.
No, wait. I couldn’t use my real name. What if someone I knew saw my profile? That would be so humiliating.
Name: Leonard White.
Age: 18
Height: 5’5”
Weight: 120 lbs
Size: 4.5”
Orientation: Gay
Position: Sub bottom
Foreskin: Cut
Safe/bb: Raw is law
Body hair: Smooth
Hair color: Brown
Eye color: Brown
Style: Twink
Body: Slim and pale, like a porcelain doll
Race: White
Zodiac: Gemini
About me: Fun, flirty, sensitive, humble bottom. I’m lots of fun and a great listener. I’m a shoulder to lean and cry on. I’m the life of the party, the belle of the ball, and the boy of your dreams.
What I’m looking for: Hot sugar daddies who love to spoil their boys rotten and fuck them silly. Aged 35-75.
I know I was putting the age kinda high, but I figured if I got a real old guy maybe I could finagle my way onto the will or something. I searched through my phone for some of my sluttiest thirst traps, a few hole pics, one “business casual” look, and then added the photos to the site.
I finished the profile in a little over an hour, but I knew I couldn’t come home yet, so I spent the rest of the day shopping online and flirting on and off with Drew. He gave me free biscotti and told me some boring shit about a band he was in (I think they did Prince covers, I don’t know, I wasn’t really listening). I told him I would definitely come to see him one of these nights and grab a drink with him after.
As I left for the night, I vaguely wondered if I would give my virginity away for free after all.
Who knew? The world was my oyster.
“So, how did job hunting go?”
My dad was standing over the hot stove, his “Kiss the Cook” apron barely fitting around his broad chest. He stirred some red sauce in a pot on the stove while I sat at the kitchen table, nibbling on a Pop-tart.
“I got hired,” I said smugly.
“No kidding?” He turned to me, grinning. “Good for you, son. Where?”
“That coffee shop in the strip mall off I-95,” I said nonchalantly. “It’s no big thing.”
“Well, that’s great,” Dad said, adding a bit of salt to the sauce. He sipped a spoonful, then nodded. “I’ll have to come visit you sometime.”
My stomach turned. “Uh, I don’t think that’s a good idea,” I said quickly.
He chuckled. “What, you’re afraid your old man will embarrass you?”
“Yes, actually,” I said, leaping on the excuse. “I’m an adult, it’d look stupid to have my parents checking up on me at work.”
Dad threw his hands up in the air. “I know, I know. You want space, I hear that. I’m just proud of you, is all. I worked all through college at my dad’s construction company. I know how tough it is to balance work and school, but I think it’ll be good for you. Give you some responsibility.”
“Uh-huh,” I said, opening up another Pop-tart.
“It’s all part of the college experience. Speaking of which, I’ve got my reunion on Friday.” He grabbed a handful of pasta and tossed it in a pot of boiling water. “It’s at a hotel downtown. Mom and I will be gone all night so you’ll be on your own for dinner.”
“Jesus, Dad, I’m not totally helpless,” I said, my mouth full. “I’ll just order Grubhub.”
He sighed, then walked over and ruffled my hair. “I really am proud of you, Leo. You set your mind to something and you worked hard to achieve it.”
Despite myself, I blushed. I felt a weird, warm, fuzzy feeling in my chest as Dad went back over to the stove and finished cooking dinner. It was kind of nice, getting validation from him. Lately we’d been at each other’s throats so much I’d forgotten what it was like to feel close again. Sure, he didn’t know I was selling my pussy to old dudes for a bit of spending money, but what he didn’t know wouldn’t hurt him. He was right–I was supporting myself for the first time. A little scary, but all new things were.
The next day I dropped Dad off at work and then drove over to the coffee shop to check for updates on my profile.
“Good morning,” said Drew when I walked in, flashing me that bright white smile. He’d put little golden clips onto his locs, which made him look even hotter than the day before.
“Hey Drew,” I said, leaning on the counter (if I had tits he’d have gotten a great view of my cleavage). “Looks like you survived the rush.”
“Barely.” He had a sexy smirk on his face like he knew we were both thinking about anal.
“Did you miss me, or do you only think about me when you’re frothing milk?”
He laughed as he wiped down the counter. “Looks like you’re in a good mood today. What can I get you?”
“Surprise me.” I shot him a playful smile. “I trust your taste.”
He chuckled softly. “That’s a tough one. I mean, you hate coffee and you don’t strike me as a tea kind of a guy.”
I laughed gaily. “You’re so silly. I’m willing to take the risk, trust me.”
He nodded, then turned and started making something behind the counter. I set myself up at my usual table and opened up my computer to see if I’d gotten any matches. Surprisingly, the selection was abysmal. I had less than ten total matches, half of which were from scam profiles asking me if I wanted to make $10,000 a day working remotely (why the FUCK would you hire a sugar baby to do remote office work? We’re dumb as shit). The rest were pretty poor as well. A man with a yacht in Florida? Too far. Another who wanted a “strict companion” and listed “obedience” as a priority? Mkay, no thank you. I could barely stick to my own rules, let alone anyone else’s.
Fuck, was this what I had to work with? Maybe I should give it away for free after all.
“I hope you like something sweet.” Drew set a large iced pink drink on the table in front of me, then handed me a straw. “Take a sip–I wanna see what you think.”
I popped the straw in the drink and took a swig. It was sweet, like strawberries and cream. “Fuck, that’s delicious.”
He grinned. “Figured you’d like it. It’s pretty popular with, uh… boys like you.”
I batted my eyelashes. “Oh, you mean cute, sexy guys with great taste, killer legs, and no plans on Friday night?”
Drew licked his lips, then laughed. “You got me there. Want me to take you out?”
I took another sip. “Hmm. I thought you’d never ask.”
The bell above the door rang as another customer walked in. “Why don’t I text you when I’m off and we can work out the deets?” asked Drew.
“I’ll be waiting,” I said sing-songily before turning back to my computer.
I spent a couple of hours wasting time on TikTok before checking my matches again, but still no one new. I was just about to reload the page when I felt a firm hand clamp down on my shoulder.
“Working hard?”
The sound of my father’s voice nearly made me jump out of my seat. “Dad? Wh-what are you doing here?”
He slid into the seat across from me, sweaty and covered in a thin sheet of dirt from work. “I wanted to visit you on your first day! So, how’s it going?”
I quickly closed my laptop. “It’s fine. I’m–I’m on a break.”
“Roger,” said Dad. He nodded his head toward Drew, who was ringing someone up. “Some cute co-workers, huh?”
I blushed. “I guess.”
“Are they friendly?”
“They’re fine,” I said, my voice tinged with annoyance. I looked over at Drew again, then at my father.
He raised an eyebrow. “Maybe I ought to introduce myself–”
“No!” I said, a little too loudly. “I mean… please don’t embarrass me.”
“Can I at least get a drink?”
I sighed. “Fine. But don’t tell anyone you’re my dad.”
Dad chuckled. “All right, son. Be right back.”
I watched him saunter over to the counter, his large work boots clunking with every step. It made my stomach sink to see Drew’s eyes light up as he approached him at the counter. My dad tipped his hat, then pointed at the menu. They were too far away for me to hear what they were saying, but from their body language, I could tell things were a little friendlier than just barista and customer.
Dad said something that made Drew laugh loudly. I rolled my eyes and buried my face in my laptop. I couldn’t believe I was watching this play out in real-time. I tried to distract myself with the Sugar Daddy website, but my lack of matches just made me even more depressed.
When I looked up a few seconds later, they were gone. I looked around and spotted Dad following Drew toward the back of the café.
“What the hell?” I said to myself. I turned around, craning my neck to see the two of them slipping into some back room just a couple of yards from where I sat. I got to my feet, arriving at the door just as it closed. When I tried the handle, it was locked.
My heart raced. He couldn’t be doing what I was thinking he’d be doing, right? In less than five minutes? That had to be a record. I put my ear to the door, but I couldn’t hear anything. Then, faintly, I heard a low groaning sound, followed by a clanking metal sound. It couldn’t be… was that my father’s belt hitting the ground?
“Oh, fuck son… that’s it…”