Sugar Match Ch. 01

--

It was near the end of the work day when Gordon called me into his office.

I walked in and sat in the chair across from his desk. Gordon smiled at me and said,

"Perry, you've done a phenomenal job today. I'm gonna go ahead and let you go home early. I was about to pack up myself because for the first time in a while, I got enough things finished I don't have to stay late. And it's all because of you."

Pride and pleasure swelled inside of me at Gordon's praise. I really couldn't wait to find a Sugar Daddy who loved my servitude as much as Gordon did.

Through a small smile, I replied, "Please, I'm barely doing anything. I'm just grateful for the opportunity to help out and make another paycheck."

Gordon's face took on a look of concern.

"Yeah, your Dad mentioned that the house you inherited from his father was giving you problems. If there's anything I can do, let me know."

A flash of annoyance at my Dad delayed me in responding to Gordon's offer. I didn't want to be mad at my Dad; I knew he was just trying to help. I didn't appreciate him talking about my personal business to his friends though.

I'm a very independent person and I couldn't stand for him to give me the money outright. It might seem like being a sugar baby would then be hypocritical but I see it as two people exchanging money for a service. I wouldn't call it "work", but I definitely feel more right about it than just taking the money from my Dad.

With a nod, I reply, "Thank you, Gordon. I appreciate that. I'll see you tomorrow, boss."

With a smile thrown over my shoulder, I return home to continue my search on Sugar Match.

--

Things had been quiet until about 6 PM in the evening when suddenly my phone alerted me to a message.

Sugar Match: You have a new match

Excited apprehension engulfed me as I quickly pulled up the app I installed on my phone with my Sugar Match account and quickly checked the messages.

I read,

You have been matched with a Sugar Daddy who meets your personality questionnaire with a 98% match. The match will not be notified of your information until you decide to make contact. Would you like to see your new match? Viewing a profile will also not notify your Match of your identity.

Wow. A 98% match. I quickly hit the "See Now" button and faced the picture and blurb of the Daddy I matched with.

Oh shit.

Gordon's strong jaw and intense eyes stared back at me from my computer screen. Confusion muddled the thoughts in my brain. I didn't even know he was gay, much less in the market for a sugar baby!

Indecision and interest warred within me. Should I click off and forget what I saw? Or should I feed my inner curiosity and read his profile?

On one hand, he was my boss for three more days and my father's best friend. It would be wrong. But on the other hand, we had a 98% match and he would never know we matched if I didn't want him to.

Deciding that there's no harm in looking, a few clicks took me to Gordon's profile. I quickly scanned his blurb describing what he wanted in a sugar baby.

"My ideal sugar baby is someone who can anticipate my needs. I would like someone who is a natural servant and submissive. In return, I would like to financially, emotionally, and physically support my sugar baby. This relationship would be a symbiotic exchange that benefits both of us. Though I tend to be more dominant, I like a boy who wants to fight me in bed, while still respecting my dominance."

Jesus Christ. I shifted on the couch while reading Gordon's profile, suddenly hot and bothered over his words.

Gordon was exactly the Sugar Daddy I was looking for. I already have experience in serving and pleasing him. I also love playing in the bedroom and the thought of pretending to be a reluctant submissive makes my hole clench in longing.

Wait. No. Starting something with Gordon would be a very bad idea. There's no way I could take money from my Dad's best friend and work partner by having submissive sex with him. If I crossed that line, there would be no going back. I would just have to find another Sugar Daddy that I matched almost perfectly with. It couldn't be that hard.

--

Gordon

After Perry left, I decided to take off early myself. As I was packing my briefcase, a ping came from my phone. Briefly looking at it before putting it in my pocket, I saw that I got a new match from Sugar Match. I wouldn't receive the name of the match unless he accepted. And I really hoped he accepted. Apparently it was a 98% match. I've never even gotten a match that was over 50% before.

Walking out of my office, I passed by Carole's desk to see the monitor was still on. I guess Perry accidentally left it up by mistake. As I went to shut down the system, I could tell there were some unopened tabs left up. Clicking over to exit them out, I paused when I read one of the URLs.

Sugarmatch.com

My mouth dropped open in shock. I quickly sat down and pulled up the page.

Not only was Perry indeed looking at Sugar Match, he also had an account and was still logged in.

Finding out Perry was gay wasn't the shocking part about finding his profile. It was realizing he was probably becoming a sugar baby because of his financial problems. If Oliver knew this, he would be crushed.

Even though I felt some residual guilt by discovering Perry's profile, I couldn't stop myself from noticing he received a new match today. Curiosity lead my hand as I clicked on the matches and looked at the man Perry would potentially be serving. Jealously tore at me as I looked at the bastard. Realization cut me to my core as the image loaded.

It was me.

If Perry matched with me, that means that the 98% match I was alerted to earlier...was Perry.

A barrage of emotions flowed through me. The first and foremost being want. I wanted to so badly to pursue Perry and ask him to consider this. I had been struggling so long to find someone near perfect for me and then he falls into my lap.

The only thing holding me back was Oliver. If Oliver knew I even contemplated paying his son for sex and submission, our friendship would be over. Still, my brain tried to rationalize a way I could try to still see Perry but there was just no way around the fact that I couldn't betray Oliver like that. I would just have to stay away from. No matter how hard that could be.

Suddenly, I realized that if Perry matched with me, he knew about my being a Sugar Daddy. He just didn't know that I knew we were matches. My brain hurt trying to keep up with rabbit hole we had fallen down in to.

I wonder what Perry would do. Would he ask me out, or ignore our match? I guess his decision didn't really matter since I would reject him anyways. Though it would break my heart to do it. I would just need to get through the next few days until Carole came back and then it wouldn't matter. I would deal with whatever he decided to do.

--

Friday

The last two days of work were the tensest they had ever been. Perry continued to be a wonderful assistant, realizing my needs before I did while keeping away employees who waste my time.

However, things between Perry and I were awkward. I was of course keeping my distance. But so was he. Considering I never got a message that relayed Perry accepted my match, I guess he was going the ignore route. Part of me was hurt, but I understood all too well why he chose this path. Neither of us wanted to hurt Oliver.

To make matters worse, on his lunch break the last few days, I could hear him talking and laughing on the phone with someone the whole time. Had he already moved on? Did he have a sugar daddy that wasn't me? Jealousy and hurt burned in my stomach everyday but I knew I had no right.

I was all set to ignore the situation as well since he was ending his temporary position today anyways, but an hour ago I got a call from Carole.

Apparently she was practically recovered from the flu, but now her children were sick. She barely took any of the copious amounts of vacation and sick time I gave her, so when she asked for the next week off to care for them, I quickly gave it to her.

Now I had to decide whether I should ask Perry to stick around for another week, or try to be without any help.

I knew immediately that I couldn't function with the second option. Keeping Perry around wasn't ideal since I still fought with my decision everyday to ignore the fact we were practically perfect matches, but I needed a competent assistant. Someone who was a natural servant. Perry was too perfect to let go. I had little doubt that he would say no.

It was lunch time when Perry came in with my a bag of food. He had been ordering me healthy options all week and today was no different. Walking in without a word, he sat the bag down and made to leave. I stopped him and asked him to sit down.

--

Perry

After I discovered Gordon and I matched almost perfectly, I decided that keeping my distance while I still worked for him was my best plan. I spent most of the time talking to Teddy about my situation and trying to keep calm. Today was my last day and it wasn't like Gordon knew we matched, much less that I was a sugar baby in the making.

Setting down his lunch for the last time, I went to leave when he stopped me. I sat down at his request and braced myself for his next words.

"So Perry, I'm going to cut right to the chase. You've been doing flawless work here for the past few days and I'm very impressed with your ethic. It turns out that Carole is going to be out another week and I still need an assistant. What do you say to staying on with me for one more week?"

There was no way I could do this another week. Everyday I looked at Gordon, I hated that I couldn't have him, couldn't be his sugar baby. I even tried to match with someone else but it didn't feel right. Which put me in a precarious situation financially but that was another problem.

Stealing myself for his reaction, I started, "I'm sorry Gordon, but I'm going to have to say no."

Shock filled his features.

"Really? But why? I thought we worked good together."

"We do, but I just can't work for you any longer. I'm sorry."

I made to get up and leave but Gordon stopped me at the door. He pressed my back into it while looking down into my hazel eyes with his, mouth set in a firm line. If he kept pushing, I knew I would break. Just the feel of his strong body pressed into mine made my cock start to harden. Looking up into his eyes, I whisper,

"This can't happen."

Understanding lights Gordon's face. He pauses and then says, "Can this not happen because of your Dad or because you ignored our match on Sugar Match because of someone else?"

I was stunned into silence. How did he know we matched? The site said he wouldn't be notified unless I released my information to him and I definitely didn't do that.

At my questioning look, he said, "You left account up on your computer the other night. I saw that you matched me. But then you never sent a message."

My shock starts to wan as I gather my thoughts.

"I'm sorry I never messaged you. I was just so shocked at finding out you were even on the sight. But when I saw we matched, I just knew I couldn't do that to my Dad. You don't know how badly I wanted to message you and see if we would work, but I couldn't betray him."

Gordon was nodding his head.

"I completely understand. Ever since you started working here, serving me like this, I started to want you as my own. Learning that we were almost a perfect match broke my heart because I knew I could never have you. Now I get jealous every time the phone rings and I hear you laugh. Because I know I could never be that person to you."

I close my eyes and lean my head against his chest. My resolve starts to weaken at his words. I want him with every inch of my being. I sense his eyes on me and look up into his steel gaze. His lips are right there. All I would have to do is lean up a little bit and I could have his mouth on me in an instant.

Gordon appears to read my mind because his head falls a few inches towards mine, and suddenly we're kissing.

--

Gordon

God, he tastes better than I ever thought he would. His little body wraps around me as I shove him into the door. Our mouths continue to meld around each other. Before this can go any further, I pull away and ask,

"Do you want this?"

Perry is a vision as he continues to pant against the door. His eyes are cloudy with lust as his mused hair sticks up around him. He nods and says,

"Yes. I want it. I want to serve you and only you."

His words light a fire in me. That's all I wanted to hear. Walking until our bodies meet once more, I whisper,

"That's a good boy. Strip for me, Perry."

Without a word, he quickly undresses until he's stark naked, pressed against the door. All thought fades as I take in his beautiful body, exposed only for me.

I caress my hand down his face until I grab his chin and yank it up to meet my gaze.

"If you want this to work, you gotta show me how good you can be for me. Show me how bad you wanna serve me."

I lean in to own his mouth, sweeping my tongue inside as I pull pleasured moans from him. Lifting Perry off the ground, I carry his lithe form across my carpeted office and set him onto the desk, never breaking our heated kiss.

When Perry's bare ass hits the polished, cherry wood, his legs immediately sneak up my hips to wind around my waist. He uses his legs to pull me closer to him while I pet his thighs with my hands. He shudders over and over every time I bring my hands inside his thighs, teasing the sensitive area near his cock and ass. The boy hasn't said a word in several minutes but I could tell just through his body that he was practically begging for my sex.

"Are you ready to submit to me, boy? You wanna serve me and do everything I say?"

"Yes sir", he nodded emphatically. His eyes were nearly blown out of his head with lust as his lips were swollen with our kisses.

"Hmmm. Well I think the first thing I wanna do is see how well you open for me. Lay down on the desk and hold your legs up and apart. Let me see that sweet hole of yours."

Perry whimpered before complying. He quickly went flat on his back while my hands caught his legs in the air, holding them up and spread wide.

At my gaze on his most private area, he clenched his hole just for my viewing pleasure. Through a groan, I shoved a finger into his mouth and watch as he soaked it liberally. Slowly pulling it from his mouth, I trailed it lightly down his chest and stomach until I reached his hole. When I applied the littlest bit of pressure, Perry let out a string of high pitched moans, begging me to put my finger in. Instead, I slowly circled his hole, changing direction every now and then, barely changing my speed. Perry eventually lost his patient and grabbed my hand to force my finger into his tight heat. Immediately, Perry's face betrayed his realization that he had in fact made a mistake.

"Now, now, boy. If you misbehave, I'll have to punish you."

With that, I took my hands of his body entirely. Perry was too busy complaining about the loss of my touch to be aware of the hand I swung back until it connected with his fat ass. His right cheek jiggled under my hand as he bucked on the desk and cried out. I hit him again in rapid succession, listening to his broken moans.

Even if this was wrong, the sight of a naked Perry in full submission was worth the outcome. I had finally found the perfect boy for me. Right under the nose of his father and my best friend.

Suddenly, the door to my office began to wiggle as loud knocks were heard from the outside.

"Gor? Its Oliver. I wanted to see if you wanted lunch but your door is locked. And have you seen Perry? He's not at his post."

Perry and I stared at each other in horror as I still had my hand poised in the air to slap his ass that was turning red from the force of my slaps.

I didn't know how to handle this situation. How would I explain Perry in my office with the door shut? How could he even get dressed in enough time that it wasn't suspicious?

I looked down at the boy who I got to call mine fore exactly six minutes. I silently said goodbye to him as I prepared to answer my best friend, not quite ready to face the consequences.