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 18th 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 24th. 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 24th 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.
"Would you be interested in coming back to my room?" he asks. Here it is. THE question. Holy shit, holy shit, holy shit! Before I can say anything he continues, "it's my anniversary weekend and my husband wants a hot young hook up as his gift. You're perfect." He drags his eyes up my long legs, stopping to stare at my shorts again.
I don't know what to say. I don't know what to do. I never imagined a threesome, let alone with two older married guys. One of which I haven't even seen. This guy is so hot, but he's probably old enough to be my dad. I've never considered older guys. I mean I'm only 18 and I've only had sex with one guy that is the same age as me. He was a swimmer on another schools team and we hooked up at a couple of events we competed in.
He stands there, still holding the button and vaguely I think about how slow the elevator is even without us holding it open for what feels like hours. He must realize this too because he finally suggests "why don't you come to my room now and meet Andy. Maybe that will help you decide. Either way, we have to let this elevator get going again."
I nod and step off the elevator. He follows me out, smiling that big beautiful smile again. "Thanks for coming with me. Please don't feel any pressure. You can leave at any time."
Shit, why didn't I even think about that. I could be walking into some bad shit and I didn't even consider it. I must look upset with these new thoughts, because he slows his pace and looks at me with concern.
"We can go down to the lobby and find a place to talk there if you'd rather."
I can tell he's trying so hard to not freak me out. I find my tongue and reply, "no that's okay. We can go to your room. I texted my brother where I was." Basically letting him know someone knows where I am. But it's a lie. I don't have a brother, it's just a bluff, but it makes me feel a little bit less nervous.
His room has a big double door. He slides his key card and the door clicks open. We walk in to the foyer, yes this palatial suite has a full marble foyer. I feel like the likelihood of me being murdered just got less, so that's good.
"Andy, honey, I brought someone to meet you" he calls out as he sets his phone and key card down on a table in the huge entrance. He keeps walking and I trail behind. We round a corner and come into a huge living room all decorated in creams and pink gold accents. It's pretty and too much all at one time. As I scan the room, another voice comes from the bedroom.
"What was that, Luke?" The man who was in the bedroom just now steps out into the living room and looks past his husband, to me, standing behind him. "What do we have here?" he says, while sizing me up like he's picking out the biggest, juiciest lobster in the tank.
"Behave." Is all Luke, the man I followed here, says. He motions me to a chair. I sit. He walks over to Andy and says "he's nervous enough as it is, please be nice." This isn't really helping my nerves. They both walk over the couch near my chair and sit side by side.
It's the first time I really get a good look at Andy. He's not as handsome as Luke, but he has an incredible body. They both have incredible bodies. Luke is a few inches taller and darker in every way. Andy is more average looking, other than his perfect body. His blue eyes are his best feature on his face, by far.
"I never asked your name" Luke says.
"Taylor, my name is Taylor, it's nice to meet you both." I have my hands on my knees, trying not to look nervous.
"You've probably figured out I'm Luke and this is my husband Andy" he motions to the man next to him. "It's our eleventh anniversary this weekend."
"Congrats," I smile and nod at both of them.
Andy cuts to the chase "How old are you Taylor?".
"I'm 18, I just graduated."
"I assume you have an ID?" he asks with an odd look on his face, like he doesn't believe me. I want to make a sarcastic remark, but I just nod.
"Do you want to see it?" Not wanting to reach for my wallet, like I'm in some weird job interview, even though I kind of am.
He wants to see it alright, and I don't mean my ID. Andy's eyes are glued to my package and he has a feral look in his eyes. It would be scary if Luke wasn't this beacon of calm sitting next to him.
"So Taylor, let me explain my offer from earlier in the elevator" Luke says. "Like I said, it's our anniversary and Andy wants to enjoy the company of a young man for the evening. I'll be here, but I'm only an observer. Watching Andy enjoy someone else is my turn on." He pauses, letting it sink in.
"So you just watch?" I say, at a loss for anything better to say.
"Yes. I also record it on my phone, but only with your permission, of course. The video is just for us, but we don't need to tape it if you don't want."
"Okay" is about all I can manage to say to express that I'm following along.
"Do you have any questions?" Andy asks.
"Yes, several" I finally get my brain back online and I realize I need to start participating in this meeting right now. This is the business before the pleasure and this is when I can decide if I want to continue. Once we start, it will be harder to ask for more info, I'd imagine.
"Tell me a little about you guys" I'm not sure what I'm expecting to learn, but I need to know something. Right? Before I can second guess my question, they both smile and start talking about themselves.
"We're both personal trainers and we own a gym in Indianapolis." That explains the bodies. Luke continues "I'm 44 and Andy is 40. This is our fourth year in a row that we've come to Pride for our anniversary."
Andy adds "We usually have my boy toy lined up before our trip, but our original plan fell through a few days ago." He looks at me, like he's waiting for my reaction. "Conner found out his wife was pregnant and he got cold feet. I tried to convince him to do it anyway. Babies are expensive."
What? Wait, were they going to pay this guy Conner? I didn't even think about money being exchanged either. I'm so out of my fucking depth here. I want to ask about the money, but that's a hard topic to bring up.
"We used Conner last year and he used the money to help pay for his wedding."
I look at Luke, who just said that. "Is Conner a prostitute?" I blurt out before I can stop myself.
"Oh heavens no! We met him online last year and he was looking for an experience before he got married. We became friendly and we offered him some money, as a wedding gift really" Andy clutches his non-existent pearls. "We stayed in touch and asked him to join us again this year. Her backed out, even though we offered him a large gift again." Andy smiles at me. He basically just explained he paid this guy for sex, but it was "just a gift". Whatever helps you sleep at night.
Luke looks like he's ready to get this conversation out of this dangerous territory, so he says to me "in the elevator you said you were having a slow night, so I assume that means you're not making much in tips, which is why I asked you to consider my offer to join us." He didn't say he was offering me money outright, but he sure seems to be alluding to doing just that. He continues on "I guess it technically is paying you, but we can afford it, and we want to show our appreciation, with a gift or a tip. You know, not an hourly rate thing, but a generous thank you gift."
He looks uncomfortable. I feel uncomfortable. Andy looks worried that plan B is getting cold feet. I say the first thing that comes to my mind, and change the subject "Do you guys do this often, or just for your anniversary?"
Luke looks relieved to move to a new topic, "just on our anniversary. I've offered to let Andy have his hook ups for other occasions like vacation, or whatever, but it seems to work best for both of us to enjoy this once a year. He gets a different cock and I get to watch him enjoy it. It's perfect for us." He looks really happy, so I'm not questioning it further.
"How big is your dick Taylor?"
I look at Andy, who's just asked that awkward question. I guess it shouldn't be awkward, seeing as though that's what is on the table, so to speak. "I'm a little over nine inches" I try to sound confident, but his eyes are huge now and it makes me nervous.
Andy twists on the couch and looks right at his husband. He's grinning from ear to ear. "I want him Luke." He sounds like a spoiled child at that moment.
"Honey, it's up to Taylor, not me" Luke says so lovingly, while he pats Andy's hand.
Andy turns back to me and I'm sure he's about to flat out ask if I'm in. Luke, always the voice of reason, stops him with a look.
"So, Taylor, that's basically what were looking for. If you're interested, we could get into further negotiations and we can write up an agreement that we can all sign, that breaks down what you're willing to do or not willing to do." He looks at me hopefully.
"Do we have to make it so businesslike?" I ask before I even realize I've had the thought.
"No, of course not. We really only need to discuss expectations and agree on a safe word."
The term "safe word" just about causes me to bolt. I'm a damn teenager, this is crazy. I'm not ready for safe words and contacts and "generous gifts". My apprehension must be plain for them both to see and Luke starts to back pedal.
"Taylor, are you alright?"
"Yeah, this is all more complicated than I thought it would be."
Luke leans forward slightly "it really doesn't have to be. I just want to offer you anything you need to feel comfortable, but it can have the opposite effect . I'm sorry." He looks so kind right now. "I guess the first question is, are you interested in having sex with Andy?"
I look at Andy. He's got a beautiful body and he wants me to top him. That would be easier than bottoming for a stranger. And Luke makes me feel comfortable. He'll be there the whole time and that makes me actually want to do it. I want Luke to watch me.
What?!?!? The realization that I'm considering fucking this guy to please his husband is crazy. I wish it was Luke I was going to fuck. He's incredible. He's hot and sweet and I feel at ease with him. It doesn't matter Tay! Snap the fuck out of it, Luke isn't on the menu. Do I want to fuck Andy? That's the only question.
An hour later, we're eating some healthy snacks and salad, which isn't my favorite because it feels like training season, but these guys are gym owners. I shouldn't be surprised we're not eating that deep dish pizza I never did get to deliver to anyone for a big tip for showing off my package. My plan went out the window and somehow I'm the "boy toy" for a married couple for the night.
Over the meal, we discussed our 'what we were willing to do and not willing to do' list. It all seems to lean in my favor. He wants to bottom for me. He wants to blow me. Some kissing and I can jerk him off or suck him if I want, but I don't have to. We agreed to no safe word requiring activities. Condoms are a must for anal.
We never discussed money again. I really could use some money, but it feels too weird to bring it up. I have a feeling Luke won't let me leave without a "gift", but I don't want to count on it, or expect it.
After the meal, I excuse myself to one of the three bathrooms in this ridiculously huge suite. I wash my face, my balls and my ass. I see a basket on the counter, stocked with toiletries so I brush my teeth. I stare at myself in the mirror for a few seconds. I'm doing this. Let's go Tay, you got this.
When I come out of the bathroom, there's some music on, floating through the whole suite. It isn't the music I would pick, but it's better than silence. I find Andy and Luke in the living room. Luke is in the chair I occupied earlier and Andy is on his lap, whispering in Luke's ear. They look really happy together.
Luke smiles at me and pats Andy's ass. "Let's move this party to the bedroom, shall we?"
Andy climbs off his lap and walks toward me. He grins and takes my hand. "I've never had such a young guy, you know. I've always wanted a barely legal romp and the big dick is a bonus." He leads me to the bedroom with our fingers entwined.
I look over my shoulder to make sure Luke is following. He is. I turn back towards Andy and I see the bed is enormous. I have the thought that we could fit four or five guys on this bed. My inexperienced ass is thinking about orgies when I haven't even gotten through this experience. Calm the fuck down brain.
We reach the edge of the bed and Luke walks past us to a big cushy chair in the corner. He easily hefts it up and moves it right to the end of the bed. He sits down. At dinner, I asked him not to record. He didn't even bring his phone into the bedroom. God, he's so fucking dreamy.r"
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Pub: 25 Mar 2021 07:59 UTC
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