Be a Sugar Baby
Expect the good life
- Jacqueline

"Jacqueline, love, did you hear me?" Dustin, my millionaire sugar daddy for the weekend asked. I was in my bikini, relaxing on the lounger as the man put his phone away. "Sorry, must be the heat. Do you want to go back inside the villa? I think I'm baked, I need to cool off." I replied peeling my eyes away from the soothing landscape of the shoreline.

I love tropical beaches and Maui has a beautiful shoreline and exquisite beachfront villas. I would love to go to Fiji or Maldives but I took what I was offered, the guy looked like he was one foot away from a board meeting. So, I settled for Maui and honestly I can't complain, I was loving the private beach, lush landscape, and the array of tropical fruits available on the kitchen island.

One afternoon sex later, I left him dozed off in the master bedroom while I skinny-dipped in the villa's private swimming pool. My body hummed in content, my mind relaxes, my eyes were spoiled by the late afternoon view of the surroundings.

Three lazy laps later I decided to rest and lounge by the pool cooling off in the late afternoon air. Covering my body with the sheer beach cover-up dress, I rest my back to the pool sofa. I took my Kindle, put on my buds, and play my smooth beachy jazzy playlist. My other hand reached for another margarita mix our butler just put on the table.

That was one of the highlights of being a sugar baby for me, the freedom to travel without worrying about anything and obviously the perks of having intimacy. I love being taken care of, I love their little sweet endearments and I know I'd be getting pampered without having to think about doing the wrong thing, screwing up, or worried that I might be disappointed by any man.

In my sugar baby world the men love me, they shower me with money, gifts, and affections, and honestly what more can a girl want, right?

Wrong, turns out I'm a greedy bitch who dreams of that special someone. But I kept my fantasy locked in a box, I know it's impossible. I've seen it happen to my mom and kick myself in the ass when it happened to me and my supposed to be single older man a.k.a. my college professor at my freshman year.

I took another sip of my drink and continue reading my Kindle. All of these toxic romantic novels, I should really stop reading them. But I can't, somehow they're my guilty pleasure. Sometimes I think that I'm a masochist who likes to torture myself with the idea of the impossible.

Being a romantic suck!

It was getting dark when I decided to get back into the house, Dustin was all dressed up telling me to hit the shower. "Jacqueline, baby, go freshen up, get change. We're going to the Ritz for some drinks, turns out I need to do some networking while vacationing." He gentlemanly helped me into the house, rubbed my cheek, and put his lips on mine.

"You tasted like a very seductive tropical liquor," he hummed after breaking our kiss. I let out a fake moan and that made him smile sheepishly, telling me we don't have time, his colleagues are already waiting for him. I let out a whiny pout, he chuckles and pecks my cheek saying there's a gift for me on the bed.

Gifts, money, affections. They're all a done deal with my sugar daddy. I smiled and thanked him while I left him to take a quick shower, rinse out the pool water, and go get ready for him.

The lounge on the Ritz was not that packed, it was an upscale hangout place after all. For most who come to Maui, I expect to search for the local hangout place to taste the local life that they offer. I'd do that if I was here with my college buddies but I'm with a rich older man who had finer taste in life, so I put my arm on his and be the eye candy that I was paid for.

I was in the skimpy designer dress that he bought me, I toned it down with my Tory flats and a small leather Gucci sling that only fit my phone. It didn't take long before his buddies find us and look at me appreciatively.

"Dustin, glad you can join us, and who's this beautiful lady?" the man to my front held out his hand for me and I let him kiss my knuckles and giggle flirtatiously from his wink.

"This is Jacqueline, my date." He introduced me to two of his colleagues and I let them talk shop while I sipped on the fruity cocktail. Again. It felt like I'm pickling my insides by now, but I'm only in Maui until Sunday, cause he has an important board meeting by Monday. So, I'm hydrating my body with tropical liquor. I'll get my coffee diet back when I arrive back in the city.

Dustin's hand was on my naked thigh throughout dinner and I let it stay while I gave him my adorable smile, making him kiss my naked shoulder over the spaghetti strap dress. I was wearing nothing underneath and he had his suspicion. I can already see the bulge on his pants and it made me bite my lip, thinking he's going to pound me so hard once we get back in our bedroom.

Benji, my roommate, said that I'm a nympho for being a sugar baby for over three years now, but I just laugh at him. I told him that I was liking the attention and closeness without being actually close to any men but he waved my excuse as if he didn't believe me, as if he knows that there's more to it.

That man can see right through me, sometimes he amazes me.

"They're smitten by you." He put his lips on the back of my neck when we were waiting for our driver to take us back to the villa. He was standing behind me, his hand was to my waist feeling my ass, and groan when he finally finds out that I was naked under the dress.

"I can have that effect on people," I said smugly and he laughed, pulling me back to his front feeling the print of his dick over the thin material of my dress.

"Damn, I can't wait till we get back at the villa. But uh..." Dustin hesitated, but he continues when I asked. "Those guys were asking if we'd like to join them. I mean, I told them I asked but... do you think you'd like it?"

I know where the conversation was heading and it's not like I don't enjoy a good threesome or in this case foursome but I find the sharing and making sure everyone was content and equally satisfied always lead to an extra effort from my side. The sharing has always been too much, though I like them, I always keep them to a minimum.

And making excuses has been great so far so I went with that. "Darling, I really do like having you all to myself, all those groping... I'd rather have you all to myself."

"Yeah? you sure?" he asked again wanting me to be certain.

"Dustin," I turned to face him, put my arms around his broad shoulder and pull him down for a smoldering kiss which ended the second our car arrived in front of us. I took his hand and he laughed when I tugged him into the back seat of our rental car, a bit too rushed.

"Eager now?"

"Mm...hmm..." I wrapped my finger around his neck keep him still and shower him more kisses.

"Fuck, Jacqueline, you make me feel like a fucking teenager all over again. Sit, love, I need to text the guys, they're actually waiting for us in their hotel room."

I put on my horny face and let him text his so-called colleagues while my hand rests on his upper thigh. The trip to the villa didn't take long and I let out a shriek when he abruptly carry me inside the house, caveman style.

That night I was giving him one of my best performances, he climaxed a couple of times until his legs trembles and he slumped back to the bed. I rest my head on his sweaty chest, let him take in our intimacy, and enjoy what he paid for.

The nice thing about the sugar daddies is they rarely treat us like a human sex toy and that made me stay this long with the agency. A couple of more years, then I'd probably adopt cats, lots of them, and retire with a nice chunk of the retirement fund and be the nice little old cat lady.

Until then...