The Real Sugarbaby of Melbourne

Previously on the Real Sugarbaby of Melbourne…

“I just want to hold you close to me for a bit…”

“I want to feel you inside me…”

“Sleep with me tonight, baby…”

I slept with Randy almost every night, so his request didn’t take me by surprise. But it was when Randy stopped me from undressing myself for the second night in a row that I realised he wanted me to actually spend the night in his bed with him.

Randy snored peacefully behind me, his arms wrapped tightly around me. I was struggling to fall asleep, however. For starters, this was the first time I had slept in the same bed as Randy in a long time; and I couldn’t believe that I had spent the day christening every single inch of Jack’s house with him and ended up in the arms of Randy Myers.

A sense of dread and guilt came down on me. I was snuggled up with a man that adored me despite how unconventional our arrangement was, only hours after giving every inch of my body to another man that I was inexplicably infatuated with.

My hands gripped onto Randy’s and squeezed them tight. I let out a sigh and tried to shut out my thoughts. After all, I really enjoyed being wrapped up in this man’s warm embrace.

I was awoken by Randy getting up out of bed to get ready for his day. I rolled over onto my back and sat up as I watched him shift around the room.

“Good morning, Whitney,” he beamed at me.

“Morning Randy,” I greeted him.

He rushed over to me and kissed me on my forehead before returning to find the rest of his suit.

“Come here,” I ordered him.

He put his arms through a blue shirt and walked over to me, his defined abs and tight chest showing in his unbuttoned shirt. He stood in front of me while I helped him button up his shirt, which was an action that was way more intimate than it should have been.

“Did you sleep well?” he asked me.

“I did. You were the most perfect personal heater, Randy.”

He smiled at me, the salt and pepper in his well-manicured beard almost sparkling underneath the light. I took the time to appreciate the rugged masculinity in Randy’s face, from his strong jawline, to the lines in his forehead and next to his eyes that represented the hard work he had put in over the years to build his empire.

In the middle of all my duties as his sugarbaby and private fleshlight, I sometimes forgot just how attractive Randy was. And even though he could be abrupt and blunt with me sometimes, he was kind and caring and very generous.

“What are you thinking about, Whit?” he asked me, snapping me out of my thoughts.

“Just appreciating the man that you are, Randy Myers.”

I stood up to do up his top buttons and flatten his collar like a good sugarbaby should.

“Very handsome,” I declared.

Randy smiled and pressed his lips against mine gently.

“Let me take you out to a nice dinner tonight,” Randy said. “If you don’t have any other plans, of course.”

“I’m all yours, babe.”

“I’ll send a car for you at 5:30, okay?”

Randy kissed me once more before picking up his bag and walking out. I fell back down onto Randy’s bed and sighed.

Before I even realised what I was doing, Rachel had answered my phone call.

“Three days in a row, Whit?”

“I’m so confused, Rach,” I began. “I spent the day with Jack yesterday and it was so great, but then I come home and Randy is being super sweet and romantic, something I had never witnessed before. It’s confusing me.”

“Okay, okay, that sounds like a shit show. Let’s start off with Randy. How do you feel about Randy?”

“I know it just seems like I like him for his money, and trust me it would be easier if that were the case, but I really do like him. And he’s also hot as shit.”

Rachel paused. “And what about Jack?”

I let out what felt like the 500th sigh that day. “I really like him, Rachel.”

“Have you ever tried talking to Randy about changing the terms of your relationship? Maybe he’d be okay with you seeing other people.”

Now that I thought about it, I had never once questioned the terms of our agreement. I always smiled and complied because I knew at the end of the day, Randy was paying me a salary to literally do nothing.

“He’s taking me out to dinner tonight, so I guess I could try bring it up then.”

My phone vibrated, signalling a call from none other than Jack Underwood.

“I gotta go Rachel. I appreciate your wisdom as always. Have a good day!”

I quickly hung up and answered the call that was waiting for me.

“I was just thinking about you,” I said, maybe sounding a bit too eager.

Jack chuckled, and I could picture that sexy smile of his. “Should I be worried or flattered?”

“Definitely the latter,” I said. “Is this a personal or a professional call?”

“I’m hoping both. I have your photos ready, and instead of emailing the link to you, I was hoping I could show you in person.”

With the possibility that Randy could be fine with me seeing Jack, I eagerly accepted his offer and quickly got dressed. Half an hour later, I was pulling up next to the curb in front of Jack’s house for the second day in a row.

Jack blew out a breath upon opening the door. “You are breathtaking, Whitney Kross.”

He took the words right out of my mouth as I drank in the sight of a shirtless Jack, dressed in nothing but a grey beanie and a pair of navy briefs.

Without a word, I took his hand and he pulled me inside of his home, planting a sweet kiss on my lips. He led me into his study where he had his three monitors set up with his computer. Jack sat down on his chair and began clicking on his mouse.

“These photos are so beautiful, Whitney.”

Jack pat his left thigh and I immediately sat on his lap, his free arm quickly circling around my waist. I looked at the screen in front of me and Jack began scrolling through the photos he took of me in several provocative poses and in skimpy outfits.

He stopped on a photo of me in the red panties with my black t-shirt on. There was no sexy pose here; no bedroom eyes in the photo. It was just me sitting on the couch, mid-laugh, my eyes lighting up as I no doubt was staring at Jack behind the camera.

“This is my favourite photo of you,” he explained. “I get why someone would want the sexy photos with your hips sticking out – and don’t get me wrong, I appreciate those as well – but this is my favourite. You look so beautiful, so natural, so yourself here.”

After all these years of being with Randy, I wasn’t sure that a man could ever make me feel like this. This feeling of butterflies rapidly flying around in my stomach; this feeling of being absolutely smitten with someone and wanting to spend every waking moment with them.

I looked over my shoulder at him and his hazel eyes met mine. I leaned down and kissed those sweet, full lips of his.

“These are great,” I said.

“I’ll have these sent to Randy by tonight.” Jack’s smile disappeared at the sound of Randy’s name.

“I know Jack. I’m trying to figure it out as well. But I really enjoy being with you, and I don’t want it to stop.”

To convince him that my words were true, I kissed him once more, this time more passionately. I felt him smile against my lips before he scooped me up in his arms and carried me to his bedroom.

“You are driving me wild, Whitney,” he whispered as he laid me down gently on his bed.

Dressed in a beige pair of slim-fitting chinos and a thin, white linen shirt, I followed Randy into his favourite restaurant, the Jade Tiger. I had my expertly practiced smile on my face as I walked through the field of onlookers, staring at Randy Myers and his boyfriend half his age.

We took our usual table in the exclusive section of the restaurant in the back corner where we had our own dedicated server. Glasses of white wine were already on our table by the time we sat down.

“Mr. Myers, Mr. Kross, it’s lovely to have you here again,” our server greeted us. “Are you after the usual entrees and mains today, or would you like the menu?”

Randy always ordered for both of us, and truthfully I was fine with it. I always enjoyed whatever he ordered me.

“The menus please,” Randy said.

I looked at him in shock as the server disappeared to grab us a couple of menus.

“I figured you might want to try something else, something that you may like without my opinion clouding your judgment,” he said nonchalantly.

This new Randy was sweet and he was considerate and whether he was conscious of it or not, he was offering me more freedoms than I was used to. Looking into his eyes that I felt hadn’t left me since we sat down, I could see the obvious change in him just with the way he stared at me; regarded me with such adoration, as if he was seeing me in a new light.

I couldn’t leave him. If it were strictly for the money, then I would’ve jumped ship already. I had put enough away into my savings that I realistically could live without a job for a few years. But I really cared for this wonderful man sitting in front of me; the one who knew what kind of loafers I liked, or how I liked my toast in the morning.

But I couldn’t give Jack up either. Jack had woken up something inside of me that I thought had gone since my last true relationship ended six years ago. Every minute I spent with him I was overcome with a raw passion and fire that could only be tamed by him.

I couldn’t give up either of them. Not now.

The idea that he might be okay with me seeing Jack had crossed my mind. While Randy had made it clear he was allowed to fuck other people, I had never actually seen or witnessed him do it. Maybe he’d be okay with it if it was something that wasn’t around him.

“Do you see anything you like?” Randy asked me.

“Randy, I want to talk to you about something,” I said, completely disregarding the menu in my hands.

“That’s actually why I wanted to take you out to dinner tonight.” Randy smiled at me. “I wanted to talk about something with you that I think you might really like.”

Could this man read my mind?

“What’s up, Randy?”

“I want to change the terms of our relationship,” he replied. “I appreciate the person that you are, Whitney, and I’ve really taken you for granted for the past year or two, and I want to change that. I haven’t seen anyone other than you because I have no interest in anyone other than you. We don’t have to put a label on it, but I want to be exclusively yours like I know you’re exclusively mine. No more open relationship. No more individual bedroom. Just you and me, together. What do you think?”

Next time on the Real Sugarbaby of Melbourne…

"I think I'm in love with you, Whitney."

"I never want to lose this feeling..."

"I'm torn. I'm so torn."