It's late June in Chicago. It's the Thursday of Pride weekend. The hotels in boys town and downtown are really filling up, starting tonight. If you didn't reserve a room a year ago, you're not getting a room. A few of the boutique hotels in the loop are catering to the gay crowd this weekend, flying rainbow flags and using fancy rainbow lighting on their classy facades.
Those are the places I'm planning on working tonight. I deliver food and groceries for all the different apps.
This is my first time I really get to enjoy the Pride festival and the parade. I'm 18 this summer, just graduated from high school. I've got a nice swimming scholarship at a great school on the west coast and I need to make money this summer.
I'm tall and lean, the typical swimmer build. My hair is dark blonde and my eyes are brown. My skin is nice and tan since I swim everyday in my family's pool. It's a large oval, above ground model that my grandparents paid for when I started winning swimming awards in the sixth grade. Gramps is positive he's going to see me at the Olympics one day soon. Luckily I enjoy the sport and I appreciate their support.
I'm glad high school is over though. Being gay in a middle class Chicago neighborhood isn't the easiest thing. I know it could be worse, I at least had my teammates that stood beside me. It's mostly because I was the best athlete on the team, so they didn't really have a choice. I'm hoping the liberal school on the west coast will be different.
I mostly want to shed my nickname I got freshman year. The guys on the team call me Rudder. I can't stand it, so they persist. You see, I'm rather well endowed. It's quite large, even flaccid. And it barely fits in my speedo. So it bulges out in a huge ridge from the top of my suit to between my legs. It's my "rudder". Fuck them. They're just jealous and I'm pretty sure the guy that named it wanted to suck it.
This weekend, I'm using my rudder to my advantage. This thing is going to earn me some big tips. I laid out my clothes last night, focusing on my package. Tonight I'll be wearing a close fitting red t-shirt and a pair of grey shorts that are really tight on my thighs. My dick lays down the left leg, pinned in place by the tight fit. It looks huge in these shorts.
I'm imagining myself in this, delivering a deep dish right to your hotel room. My charming smile plastered on, my blonde hair falling over my tan skin and my big brown eyes. I pull my phone out to complete the delivery, making sure to draw attention to the pocket rocket area. Make sure he gets a nice eyeful. I'll head back to my bike and cross my fingers the tip alert on the app dings in the next few minutes.
I have the best outfits saved for Friday and Saturday deliveries. I hope those nights are even busier. I'm probably going to work right in boys town those two days. Balconies full of screaming gay men need sustenance and me and my big ol' cock will bring it right to their doors. Now fingers crossed I can pull this off and that it actually works. I could be totally delusional.
My first delivery of the night was chicken from a fast food place. The guy is fat and old. He can't see me beyond his focus on that huge bag of chicken for one. No tip.
The next few deliveries are normal neighborhood deliveries. One average tip and one larger than expected tip from the frazzled mom that had kids meals delivered. She never looked me in the eye, she was too busy checking out my bulge. She wasn't my target demographic, but a good tip is a good tip.
Finally I get a delivery of really good Japanese food to one of the fancy rainbow light hotels. The doorman waves me in and points toward the elevators. The doors are gold colored and polished to a mirror finish. I check myself out while I wait. I reach down and squeeze my meat, repositioning it in the reflection.
The elevator chimes and the doors slide open just as I release myself. Standing in the elevator car is a seriously gorgeous man. He's talk, dark and built. He looks up from his phone, smiles at me, and steps out. He goes about his business and I'm really disappointed that he wasn't there to meet me for this food.
I step into the empty elevator and push the button for the 18
th
floor. I arrive at the floor and find room 1804 at one end of the hall. I knock and I hear a muffled voice acknowledging me. A few seconds later the door swings open and a really cute ginger guy in a towel, stands there smiling back at me. He motions me to come in and gestures towards the table at the far side of the suite. I walk over and set down the bag. I turn around to head back to the door and he's just standing there watching me.
Another man comes in the door from the hall, using his key card. He's an older black man in a business suit. They don't look like they would be sharing this suite, but they start taking about the food and the younger guy compliments my perfect timing. I head to the door and let myself out. The elevator is taking so long to come back up to this floor, I start fucking with me phone. Those guys gave me a 30% tip. Hopefully it will get even better later tonight and the rest of the weekend.
I'm starting to consider taking the stairs down to the lobby. This elevator is ridiculously slow. I hear something in the closed elevator shaft and finally it arrives and the doors open. That same gorgeous guy that I passed in the elevator on the way in, is standing there. He smiles even bigger than last time. "I'm headed to the 24
th
. Are you heading up or down?" he asks. His voice is so sexy.
"Down" I say, "but this thing is so slow, I'd rather ride up with you and then back down from there than wait on this floor any longer." I step inside and he pushes the button to close the door. We continue up towards the 24
th
floor.
He turns his head and asks "how's your night going?"
"Pretty good, slower than I was hoping" I reply.
He nods like he understands. "We were going to order food, where do you work? Maybe you can deliver it to us."
What a nice guy. Hot and nice. Damn. I finally say "I work for a delivery app, so I have no control over what orders I get."
The elevator stops on his floor and I look over at him and he's looking at my crotch, rather blatantly. The door slides open and neither of us move. He keeps staring and I'm afraid I'm going to get a boner, which wasn't ever part of my plan. The door dings and starts to close with both of us still inside. This snaps him out of it and he jams his finger on the open button and the door slides back open again.
He finally speaks, "what time do you get off work?". This question catches me off guard. What is happening right now? Is he inviting me to come back for...............further inspection of my package? Holy shit, don't freak out, I say to myself.
"I can get off at any time" I say and then realize what I said and I blush dark red to the roots of my hair, my reflection in this dam elevator making sure I see my embarrassment from every angle. "Uh, I mean I set my own schedule. I can log out whether I want." I'm pretty sure my secondary explanation was unnecessary and only makes the first statement sound worse. I hope this elevator drops me to my death right now.
