Sugar Match

Perry

"Excuse me, how much did you say it would take to get this fixed?"

I was standing in the basement of the two story brownstone I had inherited from my Grandfather. When I first found out he left me the house, I was stunned. I never really spoke to the man due to a falling out between my father and himself years before I was born, but I was grateful none the less.

And then I moved in.

There wasn't a thing in this house that functioned the proper way. If it wasn't a leaky roof, it was the creaky floorboards. If it wasn't the clogged bathtub, it was the heating element in the stove. Every time I scrounged enough time and money to get the first problem fixed, another one popped up.

Now, as I stand adjacent from the third plumber this month, he informs me that the continual flooding in my basement every time it rained would take over $3,000 thousand dollars to fix.

I was a college student with a crappy job at a coffee place. There was no way I could afford to pay that. I had already moved out of my old place to live here because there wasn't any rent and I thought my expenses would be lowered. Turns out I had just inherited another pain in the ass.

My Dad was super rich but I hated asking him for money. He would be more than happy to help me out but I really wanted to do this on my own. No matter how impossible it may be.

I turn to the plumber as he says, "Sorry, kid. I know that's not gonna be a fun hit to the bank account. If you can scrounge the money in time, I can get some guys in here within three weeks to fix the problem."

He hands me a card and says, "Call me in the next couple days and let me know if you wanna do business. Have a good one." With that, he climbs the stairs and let's himself out.

Turning around, I grab the wall with both hands and yell my frustrations out. I wish I could just sell the damn house but the conditions of the will stated that I had to live here for a whole year if I accepted it. I wish I could go back in time and have it inspected before I signed on the dotted line.

Walking up the stairs, I throw myself in a chair and try to come up with ideas on how to come up with $3,000 dollars in 3 weeks. Coming up with no ideas besides prostitution and selling my organs, I lay my head down on the table, preparing to have myself a big ole gay pity party.

--

Later on during my shift at The Tasty Mug, Teddy listens to my latest problems as we tag team a couple of large macchiatos.

"So if you happen to know a way to make a lot of cash in a very short amount of time, don't be afraid to holler at your boy." I finish, chuckling even though nothing about my situation is remotely funny.

Teddy gets a contemplative look on his face and then turns to me.

"I actually do know of a way to get your basement fixed but it's a little outside of the law."

I turned to Teddy and gasp jokingly under my breath, "Teddy, are you into drugs?" Teddy was a very small, innocent looking twink and I wouldn't believe his ass would ever be into anything that hardcore.

"Oh god no! I've never even smoked pot before! No, what I'm talking about is more on the lines of...sex work." Teddy's face blushed bright red as he stumbled across the word "sex". I'm not sure what Teddy was trying to imply with his vagueness but I wasn't turned off at the idea of having sex for extra money. I've always loved sex and I knew I wasn't that bad to look at. I wasn't quite the twink that Teddy was, but with my light curly brown hair, hazel eyes, and a slim, short figure, I definitely did alright for myself.

"Teddy, I need you to spell it out for me, honey. What kind of sex work are we talking here?" If he meant plain ole hooking on the corner, I would have to pass on that.

Teddy went quiet as he placed lids on to the coffees we finished and passed them over to our costumers with a smile. He came back over to me and we got started on the next orders. Finally he looked around for our boss before starting to talk again.

"Do you remember last year when I got into that accident and my car was completely totaled?"

At my nod, he continues.

"Well, I really appreciated you guys here at work raising money for me to get a new one, but it didn't really cover all the expenses I had. That's when I heard about an online service that pairs rich clients with boys who need extra money. I was matched with an older man named Thomas who paid all of my expenses in a monthly fee. All I had to do was be at his beck and call during designated hours. To do designated things," Teddy finished with a suggestive raise of his eyebrows. As understanding dawned on my face, Teddy's cheeks went red from blush.

My mouth dropped open as I stared at the still blushing Teddy.

"Teddy, are you telling me you were a sugar baby?!"

Teddy whipped around to looked behind us while shushing me and thumping me on the arm.

"Perry, shut your whore mouth! Jesus." Teddy calms down and continues on doling out portions of bean juice to strung out soccer moms. Again, he looks around and then continues.

"Yeah, Perry. For a very short time, I was a sugar baby. And it was actually really nice. I was matched with Thomas based on our common needs and personalities. We spent most of our time talking and comforting each other. And yes, I know what your about to ask, you skank. The sex was fantastic. He let me decide how frequently I would give it up and my pay was never based on our sex. I've since quit the agency but Thomas and I still meet up from time to time." Teddy finished. If it was possible, his face continued to grow redder. I would definitely have to ask him more about Thomas at a later date, but now I was too intrigued with this idea.

Listening to Teddy describe his life as a sugar baby made me extremely interested in becoming one myself. The way he explained it, it sounds like I could find a Sugar Daddy who was made for me and my needs. I actually really liked the sound of serving someone else too.

"Listen, Teddy. That sounds fan-fucking-tastic. What's the name of the agency you used to find a daddy?"

"Its called Sugar Match. You pay a very small fee and then take the questionnaire that matches up daddies to boys. You'll get matches based on how comparable you match with other daddies. Then when you start receiving matches, you get the option to message them. The service is all about the protection of the boys, so only you will see his profile and match first until you accept it. If you and a Daddy connect, you'll sign a contract with Sugar Match and then you become a free agent. When and what you and the daddy do is both your decisions. It's all very safe."

Mixing steamed milk with a decaffeinated French roast, I mulled over the information Teddy was relaying. I can't believe I was considering this, but as soon as I got home, I was absolutely going to sign up for Sugar Match.

--

Gordon

I rub my eyes as the ninth interruption of my work day finally leaves my office. My secretary, Carole, is supposed to field these inane idiots but she called in sick this week with the flu. I don't envy her job one bit. Just one day of being without her interference between me and them is driving me up the wall. I should definitely give Carole a raise.

Once more, my office door flies open and another person enters my office uninvited. I was about to lose my ever loving shit when I realized it was just Oliver.

"Jesus, Gor. You look like you were about to take my head off. Should I come bother you another time?" He jokes while taking a seat adjacent to me.

Oliver was my best friend and fellow co-owner of the software engineering firm we owned. We met in college some 25 years ago and came up with the idea of Hallow Enterprises; my last name is Hall and his is Fellows.

At the time we were two crazy kids with crazy dreams but now we run a Fortune 500 business and make millions of dollars every paycheck. I may sound cocky but I was proud of what Oliver and I have created here. Even if I was tired of that hard work sometimes.

"Nah, it's all good. With Carole out of the office this week, I've been harassed nonstop by people she usually holds back. It feels like I haven't gotten a single thing accomplished. I'd get a temp but I can't just trust anybody to take her place. You know how picky I am."

Oliver chuckles and replies, "You bet I do. I was actually thinking about your problem earlier and that's why I came down. My son is off of school for the summer and he's just working at that coffee place by the campus. He inherited my good for nothing Father's old brownstone and I know it's been putting a lot of strain on his finances. He won't let me help though because he wants to do it on his own. Which I really respect. So I was thinking that maybe he could come temp for you this week between shifts at the shop. He's worked for us before and is very competent. You wouldn't even need to train him."

I'd actually met Ollie's boy a few times and I've always been impressed with the kid. The last time I saw him he was fresh out of high school and interned for us during the summer. Of what I remember of his work, he was always polite and hardworking. If I was going to get any work done this week, my best option would be to have Perry fill in.

"You know what? I think I'll take you up on that. If he accepts, have him come in to the office tomorrow morning at nine."

"Alright, thanks Gordon. You're really helping me out here. You wanna grab drinks tonight after work?" Oliver stands up and stretches.

"I would, buddy, but I have a date tonight."

"Oh man, are you still trying Sugar Match? Have you really not found anyone good yet? And Didn't you have terrible luck last time?"

Oliver's insistent questions are referring to the match service I've been using to find a sugar baby. He was the one who told me about the site in the first place. In college we bonded over being some of the only gay jocks that were out. Then we realized that we shared a lot of the same tastes. And that included having younger men serve us for money.

Apparently he meet this wonderful guy a few months ago and they're basically seeing each other now. I was happy for him but I couldn't understand why I was having such horrible luck. The boy I met up with last time wasn't the least bit interested in what I needed. It ended horribly. I wasn't ready to give up hope though. Sugar Match continues to send me new matches everyday in hopes that I'll find the one.

"I know that last time was terrible but I'm not willing to give in yet. I've gotta give it a good effort before I fold."

"Yeah, I guess you're right. Well good luck tonight buddy. I'll text you and let you know whether to expect Perry in the morning."

"Alright, thanks Ollie. Take it easy, man."

Oliver walked out my office, shutting the door behind him. At this point, work wasn't going to happen for me. Instead, I decided to update my Sugar Match profile to make sure I was pulling in the right kind of guys.

What I wanted in a sugar baby was a submissive boy who was still feisty as hell. I wanted someone who'd do what I say but give me a little fight first. I liked a little resistance play with the boys I fucked. I also liked boys who enjoy serving. I wasn't deep into service oriented kink but I really enjoyed when someone wanted to serve and meet/anticipate all of my needs.

Finagling my answers to the questions on the site to better suit my personality, I submitted my profile and waited for more matches. In the mean time, I should probably get Carole's desk ready for Perry to possibly join me tomorrow.

--

Perry

When I got home from my shift that evening, I was all set to apply for Sugar Match when my Dad called with a job opportunity. He promised 15 dollars an hour for 35 hours so I would make over 500 dollars this week alone on top of my regular job. Even though it wasn't enough to keep me from applying to Sugar Match, it would definitely help me in my goal to fix my basement.

The job was to be the assistant to my Dad's partner and longtime friend, Gordon. I actually worked with Gordon a couple summers ago when I did an internship in Dad's office. Gordon was also part of the reason I realized I was gay.

With the body of a linebacker and the face of a model, even pushing 40, Gordon was the most beautiful man I had ever seen. He had olive skin and dark, close cropped hair that matched his closely shaven beard. He looked like he'd be more at home doing manual labor or professional sports than owning a technology company.

When my father asked me to take the job just for the week, I immediately said yes. I would never give up an opportunity to perve on the delicious looking Gordon.

Now that I had to be prepared for a 9-5 tomorrow, I didn't have time to set up a Sugar Match account at all. Putting that to the back of mind, I focused on what I was going to wear for my first day back at the office.

--

8:45 the next morning found me riding the elevator to Gordon's office with two coffees in my hands. One was for me and the other for Gordon. I was sent on a lot of coffee runs during my internship and his order was ingrained in my mind. Looking at myself in the reflection of the mirrored elevator door, I admired my outfit for a minute.

I was dressed for success in my tightest chinos and pressed, silk button down with a matching blazer. Walking off the elevator feeling like pure professionalism and sex personified, I made my way past the other office's on the floor and into Gordon's.

Since he wasn't here yet, I laid his coffee on his desk and made to leave the room. Swinging around to exit, I accidentally knocked a bucket of pens off his desk and onto the floor. Bending over the mess behind the desk, I quickly picked up the pens, trying to skedaddle before I was caught with my literal ass in the air.

However, that's not how destiny decided my morning should go.

--

Gordon

Walking off the elevator and onto the floor where Oliver and I conduct our business, I heard a commotion come from my office.

I quickly rushed in to see the most tempting and delicious looking ass I've ever seen. The ass in question was attached to a long pair of skinny yet muscular legs. Suddenly, the sexy intruder heard my entrance and spun around, a bucket of pens in his tiny hands.

It appears that the owner of the beautiful ass belongs to my partner's son, Perry.

Fuck me.

The Perry in front of me now was nothing like the Perry fresh out of High School. This Perry had clear skin and beautiful bright eyes. His body was also extremely slim yet fit and muscled. He may be here so he could keep people away while I could get some work done, but now I had a new problem. Now I wouldn't get any work done because I'd just be imaging his tight ass in those pants all day.

Breaking myself from thoughts of Ollie's son, I concentrated on why he was in my office with my pens in his hands in the first place.

Sensing my question, Perry burst out, "Good morning, Mr. Hall. I was just bringing you a coffee when I accidentally knocked over your pens. Forgive me for the intrusion."

Jesus. Not only did he bring me a drink without myself having to ask for one, he also submitted so fucking good. It made me want to see him beg for forgiveness while stuffed full of my cock. Keeping my voice as casual as I could, I responded to Perry before any silences could lapse.

"It's all good, Perry. And please, just call me Gordon. Thank you for the coffee, too, by the way. You're going to spoil me."

Perry blushed and moved to twist around me so he could exit. I grunted when he accidentally brushed his bubble butt across my hard cock. Unfortunately in this scenario, my nine inch, thick cock was too big to play it off as anything else. Perry coughed and stumbled towards the door, probably thrown off by feeling my bulge. Without looking me in the eye, he said,

"I'll let you get settled, Sir." With that, he shut the door and returned to Carole's desk outside of my office.

The immediate guilt set in as soon as he vanished from sight. What was I doing? This boy was my partner's son. He was completely off limits. I think my lust at the boy must be due to the fact that my date last night with the Sugar Match baby didn't turn out well at all. I was hoping that we would end up in bed at the end of the night but we didn't even make it to dessert. I was just too pent up and anxious, that's all.

Stealing myself against the raw lust I felt for the boy, I painted professionalism on my face and walked to the door.

"Ah, Perry if you have a minute, I would like to go over your duties this week."

Perry looked relieved that I wasn't going to bring up what just happened in my office. It appeared as if we both decided to remain professional.

At Perry's nod, I quickly gave him the run down of my schedule and how to access it on Carole's computer. I also briefly told him about the small tasks he may have to do for me here and there but he was very accustomed to how an assistant would function.

I realized that Perry didn't need anymore instruction about what was expected of him and excused myself to my office. Sitting down to drink the delicious coffee Perry procured for me, I refocused my attention on getting work done. For about three hours, I had the most productive work day since Carole had to leave unexpectedly. I was finally able to get some time to myself. Every once in a while I heard voices outside the door but Perry would swiftly deal with it. I couldn't be more thankful for him.

At Noon, a quick knock at my door preceded Perry's entrance. I smiled up at him as he made his way to my desk, sitting a takeout bag out of the way of my work materials.

I looked up at him in shock as he said, "I asked my Dad what you usually ordered and he gave me a few options. I went with the healthiest. I hope that's okay."

It wasn't just okay.

It was perfect.

If only Perry could teach the boys over at Sugar Match how their supposed to behave. Half of them say they are willing to serve me and be a true submissive, but most of those boys aren't mature enough to deal with what true submission is. They could learn a lot from Perry.

Sending Perry another smile, I say,

"You're definitely spoiling me now. I'll never want Carole to come back if your this good at anticipating my needs."

And I truly meant that.

--

Perry

Wow. What a morning.

After being caught by Gordon with my ass in the air and then accidentally brushing his cock on my ass, I collapsed at Carole's desk and almost died of embarrassment when I exited his office. There's no way he didn't realize my Texas sized crush on him now.

But then he came out to remind me of my duties and it really appeared that he didn't notice. Even though the bulge in his pants was way too huge to be anything other than a cock, I tried to convince myself it was his phone or the softball bat he keeps in his pocket for emergencies. It would be less embarrassing if it was anything else.

After he went back to work after speaking to me, I got to work taking notes on his meetings this week and keeping house. I had to scare off a few people along the way but by the time lunch time had rolled around, no one got passed me to bother Gordon.

Deciding that I like serving him his coffee this morning, I decided to get his lunch for him too. A quick call to my Dad had a chicken Ceaser salad with no egg on Gordon's desk in no time. Once again, the happiness I felt at serving him made all the awkwardness of this morning worth it.

Serving Gordon also made me remember that I had yet to fill out my Sugar Match application and profile. Sitting down to my own lunch, I got to work on filling out my questionnaire, excited to see what matches I would receive.