The Real Sugarbaby of Melbourne

This season on the Real Sugarbaby of Melbourne...

"You are stunning Whitney."

"What do you want from me, Randy?"

"He can't find out about us. If he does, my life is over."

The deep, guttural groans of Randy's pleasure - along with the sounds of his balls slapping against my ass - sounded throughout his bedroom as he continued to thrust into me, each stroke long and precise as he fucked with purpose. He had one hand gripped firmly on my hip while the other would occasionally strike my ass cheek, leaving my skin tender and red raw.

"Fuck yeah Whit," Randy groaned. "This is my ass."

I felt his hand slither around to my cock and, with some spit on his hands, he began jerking me off as he fucked me at a steady rhythm. I felt myself growing harder and harder in his hand, and it wasn't long before I let out a scream of pleasure and came all over his bedsheets.

"Tell me this is my ass, baby!"

"That's your ass, daddy!"

Hearing my submission always sent Randy over the edge. It wasn't long until he let out a deep groan and I felt him shooting his thick load inside me. He gripped both of my hips and continued to thrust in me, wanting to deposit each and every drop of his cum inside me.

"Oh baby." Randy leaned forward and pressed his lips against mine, his tongue entering my parted lips almost immediately.

He finally pulled out of me and rolled away, opting to sit on the edge of the bed. I crawled up behind him and began rubbing his shoulders with my sweaty hands, ensuring to pay extra attention to each and every muscle in Randy's muscled shoulders.

"Do you want me in here with you tonight?" I peppered Randy's jawline with kisses in between each word.

Randy shook his head and offered me a smile. A silent answer that needed no further prodding.

When Randy Myers and I had initially come to our sugar baby agreement and I had moved out of my family home much to the shock of my parents, I stayed in his bedroom with him for almost a full week. One day, I had gone out to lunch and shopping with my best friend Rachel, and came back to find that Randy had set up a separate bedroom for me in the time I was gone.

I understood immediately why he didn't want to share a room anymore. He was a man in very high demand and would often work into the dark hours of the night before retiring to bed for his five-hour rest. He didn't want to be distracted by me or to be accidentally woken by me when he spent every waking minute of his day working on his business and keeping all of his employees in line.

Truthfully I liked having my own bedroom, where I could shut the door behind me and put my sugarbaby duties aside momentarily. While many people would argue I don't actually have a job and have the easiest life handed to me just because an older guy found me attractive one night, they don't understand my role as Randy Myers's sugarbaby.

To the world, Randy Myers was dating Whitney Kross, a young man more than half his age, and they appeared to be the typical successful businessman and trophy husband couple. But in private, Randy refused to put any official labels on our relationship, and Randy was free to sleep with anyone else he wanted to. The catch was I wasn't afforded those same freedoms.

It was worth it though. On top of having access to Randy's mansion, all of his cars and his entire house staff, Randy gave me a weekly allowance that would range from $10k-$25k depending on how generous he was feeling, and I also had access to several credit cards in case my allowance had run out by the end of the week.

"Get some rest," I said to Randy after planting one final kiss on his lips. "Do you want to go out for dinner tomorrow night?"

"I have a dinner appointment already," Randy replied.

He did have a dinner appointment tomorrow night, and I completely forgot about it.

"You forgot," he said as if he had read my mind.

"I did. I'm so sorry, Randy."

"That's okay, baby. Don't forget you also have that photoshoot tomorrow."

Randy had set up a boudoir style photoshoot for me tomorrow to add to his private collection of photos that he kept only for himself. I had done private photoshoots for Randy before, but this was the first one where Randy explicitly wanted raunchier content.

"I can't wait for you to see what we come up with."

Randy got up from his bed and walked over to his study desk in all of his naked glory. While he was more than double my age, I did genuinely find Randy very attractive. He was around 5'9 in height and had salt and pepper grey hair that made him every part of the daddy he claimed to be. He had solid muscle definition that had slowly begun to fade with age, but he was still in incredible shape.

Taking that as my sign to leave, I got up from the bed and pulled up the sex-stained sheets with me. I dumped them in the upstairs laundry room and pressed the call button next to the door, which indicated to the housekeeper Gerard that Randy needed new bed sheets immediately.

I disappeared into my bedroom and fell onto my bed immediately, feeling the exhaustion of today's events.

On top of keeping a proper facade on when I was in public - because I just knew the media was out there to get me the moment I slip out of character - I was essentially a hole waiting to be used by Randy. He had a very high sex drive, and regardless of how busy he was, most of the time we fucked three or maybe four times a night. I did enjoy every time we fucked though. Randy was amazing in the bed and he definitely knew how to please me; he always ensured that I came first before he delivered the final blow.

I slipped underneath my blanket and felt myself drift off to sleep as soon as my eyes had closed.

I had taken my 2020 Tesla X to the studio which was located on the other end of Melbourne to me. My friend Rachel had offered to come with me for moral support, but I turned her offer down so she didn't have to endure watching me pose almost completely nude in various provocative positions.

The deep manly voice who answered me on the intercom buzzed me in immediately and I pushed through the door straight away. I took two stairs each step until I had reached the second floor where Symphony Studios awaited me. I pushed the door open with my perfectly trained Whitney Kross smile on my face.

"You must be Whitney!"

A man rounded the corner and my breath stopped at the sight of him.

He looked like a model that should've been in front of the camera instead of behind it. He was very tall at around 6'3 and had an athletic muscular build which was very apparent in his tight white t-shirt and dark blue ripped jeans that clung to the muscles in his thighs. He had long dark hair with flicks of blonde at the tips which he had tied up into a messy bun that really complimented his well-groomed beard and tanned, olive complexion. A hint of a smile flashed across his face as he approached me.

"Jack Underwood, I'll be shooting you today."

I reached out and took his hand in mine, and if I had ever believed in the old adage of 'sparks flying', that would've been it.

"Most first timers that come in here for these kinds of photoshoots always feel nervous around me, so I just want to let you know that you have nothing to worry about. You don't have anything I haven't seen before, and I just want to make you feel as comfortable as possible."

I was already nervous having to pose nude in front of a complete stranger for photos that only one man would see, but having to do it in front of this absolute Adonis frightened me.

Jack led me into the studio and began setting his camera equipment up. I placed my bag down on the floor and looked around at the simple studio set up. Jack had set up a red almost-velvet backdrop behind a deep burgundy couch that had a faux fur drape over it.

"The colour red promotes hunger and lust," Jack explained to me. "I thought it would be best for your needs."

I simply nodded and began rummaging through my things. Randy had purposely requested certain outfits for this photoshoot, including a skimpy pair of red cheeky panties with matching red stockings and a naughty cop outfit that didn't look like it would completely cover my cock or asshole, and also provided props such as handcuffs, a big fake lollipop, and red satin gloves.

"I'll leave the room so you can get changed." Jack smiled at me and I felt myself blush at the very sight.

I slipped into the red panties and stockings and kept my black Gucci t-shirt on before calling out to Jack. He returned back into the studio and I saw his eyes flash at the flesh that was revealed in my skimpy outfit.

"O-okay, if you want to get into position, I'll test the lighting for you."

I sat down on the sofa and elongated my legs across the cushioning, crossing them at the ankles. Jack took a few practice shots and looked at his camera screen in between each shot, making sure to adjust some tiny details on his end.

"That's perfect. We'll start with this, and if you ever need a costume change, just let me know."

I wriggled around uncomfortable in a few different positions that I thought Randy would like, but it felt as if I had held a breath in the entire time I had been here under the watchful eye of this handsome photographer.

"Do you want some with the shirt off?" Jack asked.

"Eventually," I muttered.

I rolled around onto my stomach and mounted the chair, sticking my ass out to the camera at an awkward angle.

"Do you mind if I help?" Jack said.

"Go for it."

Jack approached me and began examining the scene in front of him. He threw the faux fur throw away from the set and then began looking at me up and down.

"May I?" he said, biting his lip.

I nodded my head silently.

Jack placed his hand on the small of my back and gently positioned me, making the arch in my back more apparent and sensual. His fingers slowly grazed up my back and underneath the fabric of my t-shirt, pulling the hem up with him until it was in a makeshift crop top. I felt him get closer and closer to me as his hands ran up and down my legs to move them into position.

"Is that okay?" he whispered.

"Keep going..."

"Turn to face me," he almost commanded.

I whipped my head around to look at him and his face was only a few inches away from mine. I looked down at his full, round lips and silently urged for them to get closer and closer to me so I could kiss them.

"You are stunning, Whitney," Jack whispered.

Next time on the Real Sugarbaby of Melbourne...

"We shouldn't be doing this."

"I have never felt so attracted to someone like this before, Rachel."