Ever since Ariana had dropped that bombshell on him last Friday, he had been avoiding her.  He knew he was wrong to do her that way, but he was so confused as to whether he wanted to give up his apartment and his two jobs to become a sugar baby…a kept man.  After his mom died when he was thirteen, his dad pretty much “checked out”, so he had to learn to do things for himself.  He liked being independent.

She had called him on Sunday, wanting him to come to her home for some fun and games, but he had turned her down.  Maybe I should have gone.  It might have helped me make a decision.  I am still in my prime, so do I want to tie myself down to one woman…especially an older woman?  I have to admit, she doesn’t act one in bed, he thought as a smile crossed his face remembering their sexual exploits.  He continued wiping the same area of the bar as he started to have a mental war in his mind about why he should or should not accept her offer.

“I think that spot is clean enough, Jake,” Rich said coming up beside him, breaking into his thoughts.  “Everything okay?  You’ve seemed kind of out of it the past couple of nights.  And I have watched you wipe that same area on the bar for ten minutes.  It is early, so do you want to go to the office and talk about it?  Charity can handle the bar.”

Jake looked up at his best friend, ready to take him up on his offer, but before he could, he saw the door open, and Ariana walked in.  She marched up to the bar and sat down on a stool, just looking at Jake, her fingernails tapping on the bar. Jake turned on his heel and went to make her a Scotch and coke, just like she liked it.  Rich looked from one to the other, and then it became somewhat clear to him what Jake’s problem was.  It had to do with this older woman, but he was not sure exactly how.  Without a word, he ambled away to the office.

“Are you avoiding me, Jake?” Ariana asked when he set the drink in front of her, grabbing his free hand.

“No, I am not avoiding you.”

Ariana stared at him, one eyebrow raised before saying, “I think that’s a lie, and I don’t like my sugar baby to lie to me.  That can get him in trouble.”

”Keep your voice down,” Jake whispered harshly, looking around to see if anyone was around. Thankfully, Charity was on the floor, Rich was in the office, and no one else was at the bar.

Ariana smiled before taking a sip of her drink, enjoying how uncomfortable he was acting.  It was going to be fun training him.  She could not wait to get him to her home and tie him to her king-size four-poster bed with silk scarves.  Just thinking about it made her panties damp.  They continued to stare at each other for a few moments before she stood up and headed to the bathroom.

“Hey, Jake, I need a pitcher of Margaritas with three glasses,” Charity said, coming up to the bar.  “Want to hook up after close tonight?”

Jake opened his mouth to say 'sure' when he saw out of the corner of his eye Ariana coming out of the bathroom.  “Not tonight,” he told her, watching Ariana approach the bar.  He saw her glaring at Charity when she leaned over the bar, giving Jake a good view down her shirt and of her ample chest. 

‘Okay then, your loss,” Charity said, picking up the tray and heading out to the table to deliver the drinks, passing Ariana on the way.

Ariana stepped up to the bar, picked up her drink, and downed it quickly.  “Later,” Ariana said, reaching out to grab his hand and put something in it before turning to head out the door.

Looking down, he realized that she had given him a red thong.  He felt a tug in his jeans as he knew what they meant. “Shit,” he muttered under his breath as he shoved them in the front pocket of his jeans before anyone could see them. Hurrying back to the office, he told Rich, “Taking a ten-minute break before business picks up.  Watch the bar.”

Before Rich could say anything, he was out the door.  Being early, there were not a lot of cars in the lot so it was easy to spot her car in the back corner of the lot by his truck.  He sprinted across the parking lot.  When he got close enough, Ariana moved to the back of her Mercedes.  Inching her skirt up, she leaned over the small trunk, spreading her legs, her pussy already dripping in anticipation of Jake’s hard cock taking her roughly.

As he slid between his large Ford F-250 and her car, he was already sliding down his zipper, working his shaft out.  Coming up behind her, he rubbed the head up and down her wet slit before he grabbed her by the hips and drove himself deep inside of her.  Ariana let out a moan as her inner muscles clamped tight around his cock.  Jake slipped his hand around the front of Ariana and began to rub her clit.  Jake could feel his balls starting to tighten as he began to drive into her harder and deeper, pushing her against the trunk.

Ariana fought back the urge to scream as her orgasm ripped through her body, causing her to tremble, bright lights flashing before her eyes.  Gripping her hips tight, Jake leaned forward, sucking on the side of her neck as he unloaded deep inside of her.  Jake kept her pinned to the trunk for several moments while he caught his breath.  As he pulled out of her, Ariana spun around, dropped to her knees, and licked him clean.  Jake tucked himself back in his jeans and zipped them up.  She grabbed him by the hair, pulling his head down to kiss him. 

“I will see you later,” Ariana stated.  “No arguments.”

She kissed him one more time and got in her car, pulling away while he just stood there watching her leave.  Shaking his head, he smiled and headed back to the bar just as several cars pulled in.  When he walked in, Rich just looked at him and smiled.

“Thanks,” Jake told him, taking his place behind the bar.

Rich glanced down at his watch and leaned toward Jake, whispering, “Better call Guinness Book of World Records because I think you just set one,” before he walked away laughing.

Jake didn’t have time to reply as a large group of people came into the bar.  For the rest of the night, he did not have time to contemplate his situation.  After the last customer left, he began the cleanup, anxious to get to Ariana’s even though he had to work the next day. 

When he was finished, he went to the office door, sticking his head in saying, “All done, and am out of here.”

“If you got a minute, come in and close the door.”

Jake wanted to tell him he didn’t have a minute but decided Ariana could wait.  “What’s up, Rich?  Anything wrong?"

"What’s got you so scatterbrained lately?” Rich asked, not beating around the bush.  “From your actions tonight, I would say it would have to do that woman - the one you did not bother to introduce me to...”

“Her name is Ariana and yes, it does,” he said.  Jake quickly gave Rich the highlights of the past week, ending with, “And she wants me to quit my jobs, give up my apartment, and become her….”

“Her what?”

“Sugar baby,” Jake said softly, feeling his neck and face heat up.  Slowly he raised his head, shocked to see Rich smiling and giving him a thumbs up.  “You don’t seem shocked.”

Rich took a deep breath, then said, “Going to let you in on a little secret.  I am Rachel’s sugar baby and have been for a little over three years.  It was the best decision I ever made.  Granted, I don’t think Rachel is as old as Ariana, but I wouldn’t trade my lifestyle for anything.”

Jake just sat there, staring at Rich.  He knew that Rich had met Rachel not long after Rich moved to Florida and that she had money, but he had no idea about their relationship except they lived together and Rich doted on her.

“I thought being a sugar baby meant that you were a kept man and was only there to please her? “

“For some, that may be true but not in our relationship. At home, that is my job to please her. When she had brought it up, I told her I was not giving up my dream of owning my own bar, so she helped me open this one.  Our relationship works for us and that is all that matters,” Rich explained.  “I think you should take Ariana up on her offer because she is one sexy woman.  And if you want to work, make that clear from the beginning.  Make sure the ground rules are set and you are both comfortable with them, or the relationship is doomed.”

“Thanks, Rich.  I am glad we talked.  You helped me make my decision,” Jake said standing up. “See you tomorrow night.”

Jake walked out the door whistling, anxious to see Ariana and tell her that he was taking her up on her offer as long as he could continue working at the bar.  He enjoyed working there, and he didn’t want to leave his friend high and dry.  When Jake finally found Ariana’s house, he stopped halfway up the drive and stared at it in surprise.  He thought she would have a huge house attended by hired help, but instead, it appeared to be a quaint beach house.  Being dark, he could not see much, but the size and shape of the house by the porch light and what he figured were solar lights. 

As he pulled up in front of the house, the door opened and Ariana stepped out onto the porch wearing a sheer robe.  “About time you got here, babe.  Now come on in and let’s celebrate your new role as my sugar baby,” she told him as he got out of his truck and walked toward her.