Lipstick & Stilettos

Passions Ink Press Presents

Lipstick & Stilettos

Tarra Young

Copyright ©
2012 Tarra Young

All Rights Reserved.

      
I
t was a hot summer day in Los Angeles and Jenna Taylor was still pounding the pavement trying to find a job. So far she wasn’t having any luck. She let out a deep sigh as she sat down on a park bench to rest.

       She flipped her long blonde hair out of her eyes and let out a breath of exhaustion. She stretched, feeling relief throughout her five foot seven-inch frame as some of the tension eased up.

The day was a waste. She applied to every computer tech job she could find and was told she was either over or under qualified. If only she could find some middle ground.

Giving up on the newspaper she pulled from her bag, she sat it down. She scoured every opportunity with no results. Opting for a better read, she pulled the latest issue of Lipstick & Stilettos out of her canvas bag. She flipped it open to the middle of the magazine.

There was a layout for a new island resort in the tropics. The name of the resort was in big bold letters at the top of the page:

Ocean Breeze Resort & Spa

This wasn’t just any resort, either. It was a sex resort. That was what she and her best friend, Stacy Patterson needed.

When was the last time either one of them got laid? It was been ages ago.

They could both use a vacation, too.
Should I?
she wondered. It wasn’t as if she needed to report to work in the morning and Stacy had some vacation time she would lose if she didn’t take it soon. It was common knowledge Stacy’s boss had the hots for her. It wouldn’t take much for Stacy to convince him to let her have some time off. All Stacy would need to do was wear that hot little number Jena herself wore to the office Christmas party and Stacy’s boss would be putty in her hands.

Jena laughed at the thought as she dug through her bag for her bank book. She pulled it out and opened it to view the balance in her accounts. She hoped there would be enough funds to cover the trip. There was only one way to find out.

Jenna looked down at the article and scanned it until she found a toll-free number for bookings. She took her cell phone out and dialed the number.

Twenty minutes later when she clicked it off, reservations were booked and airline tickets were purchased for both of them. “Ocean Breeze Resort & Spa, here we come,” she whispered. Now all she needed to do was convince Stacy to go with her.

* * * *

“
Y
ou did what?” Stacy sputtered as she nearly choked on her lemon raspberry iced tea later that day at a small café on Rodeo Drive, her short strawberry blond hair bouncing on her shoulders.

“I made reservations for you and me at a tropical resort. We leave day after tomorrow.”

“Are you out of your mind? I can’t be running off to God knows where. Hello?  Have you forgotten? One of us here still has a job.” Stacy’s tone laced with irritation, but underneath she heard a hint of curiosity.

“C’mon Stacy,” she pleaded. “You know your boss has the hots for you. He gets a major hard on whenever you’re both in the same room together. You can get him to let you have some time off.  Besides, you have some vacation time coming.”

“Okay, Jenna, I’ll talk to him and see what he says. That’s all I can promise, though.”

“I swear you won’t regret this, Stacy. It will do us both some good. Do you remember that dress I wore to my office Christmas party last year?”

“Yeah, what about it?”

“I’ll let you wear it when you go talk to your boss.

Stacy rolled her eyes at the thought.

“There’s no way in hell I would be seen in that dress,” she said at last. “It shows way too much cleavage.”

This was exactly why she couldn’t tell Stacy Ocean Breeze Resort & Spa was a place people went when they wanted to get laid.

A couple days later, they were on a plane heading towards their vacation of a lifetime.

* * * *

“
I
sn’t this exciting?” Jenna asked, before taking a sip of the iced tea the flight attendant just handed her.

“That all depends on one thing. You never did tell me what kind of resort this is. Where did you find out about this place anyway?”

Uh-oh! There was no way she could tell her it was a resort for people who wanted to have discreet sex or that she found it in Lipstick & Stilettos Magazine. If she did, there was no doubt in her mind, Stacy would turn around and catch the next flight home as soon as they got to the airport without giving the place a chance. “Let’s just say when we leave in two weeks, you will be very satisfied and feel extremely rejuvenated.”

“What do you mean by that? Why do I have a feeling you’re not telling me everything about this place?”

Jenna grinned slyly at her best friend. “Just trust me on this one. You’ll thank me later.”

* * * *

J
enna & Stacy stood looking around the resort. She couldn’t believe they would be staying in such a luxurious place for two weeks.

Barely clad men and women lounged around the pool. Some couples were making out as if no one were around to see them. One woman took her top off as she allowed a muscle bound man to lick and suckle on her breasts. Jenna suddenly felt aroused as she took in the scene.

Men dressed like Chippendale dancers walked around with trays. They weren’t selling food or drinks. Instead there were condoms on them and the men were passing them out to the guests. She never saw anything quite like this.

She suddenly heard her best friend gasp, but it soon turned to a low moan as she parted her lips and her tongue darted out to lick them. She followed the direction of Stacy’s gaze. A woman was kneeling down in front of a man giving him a blowjob right out in the open. Next to them was a woman on a lounge chair. Another woman straddled her as they kissed. Jenna never saw anything as erotic as the scene playing out before them. She was glad to see her best friend enjoying the show as much as she was.

Soon the man let out a low, guttural groan and Jenna could tell by the expression on his face it was all over. As if to prove her right he withdrew his cock from the red head’s mouth, and pulled his swimming trunks back up. Jenna couldn’t help noticing he was still rock hard. The woman got up and gave him a quick kiss on the lips before walking away with a smile on her face. She reminded Jenna of the cat who swallowed the canary. The man himself was extremely endowed and his cock stained against the fabric of his trunks. What she wouldn’t give to have her turn with him. He was the sexiest man she ever laid eyes on with his dark wavy brown hair.

He rose to his feet. Without warning he turned and caught her watching him. Her mouth went dry as her eyes the locked with the most incredible blue eyes. He winked and then blew her a kiss before walking away. All Jenna could do was stand there and watch his departing back.

“Earth to Jenna,” Stacy’s voice penetrated her thoughts as she waved a hand in front of Jenna’s face. “What’s come over you?”

“That man has. If it’s the last thing I do, I have to have my turn with him before we leave.”

Stacy chuckled. “Good luck! Now can we go find our cabana? I want to talk to you.”

Jenna realized it was time to face the music. She reluctantly followed her.

* * * *

“How could you do this?” Stacy demanded once they were in the privacy of their cabana they would be staying in.

“Why are you so upset? I knew you would react this way once you learned what type of place this was.”

“Leave it to you, Jenna. I should have known you would pull something like this.” Stacy threw up her arms and then let them slap her sides as they fell.

“C’mon Stacy, I’m sorry, but you really do have to admit you were enjoying that little show out there as much as I was.”

“Yes, but that’s not the point – “

“Can’t you just relax and enjoy this vacation?” she said, cutting Stacy off. She stood and began to unpack.

“Well, I guess – “

“You need to get laid.” She cast a devilish grin at her best friend.

Stacy laughed as she picked up a pillow and threw it at Jenna. “Speak for yourself.”

“At least I admit it,” Jenna said as she bent to pick up the pillow and tossed it back at Stacy, “especially if it’s that hunky man we saw out there who is doing the laying.”

Stacy laughed as she bent to pick up the pillow. She placed it back on her bed.  “You really do have it bad for that guy, don’t you?”

“Well of course.”

“Are you serious about having sex with him?” Curiosity laced her tone.

“Yes.”

“Oh my freaking God, really?” Stacy asked in disbelief; her eyebrows arching. She quickly looked away.

“Are you saying you don’t want to?”

Stacy froze and slowly turned to look at Jenna. “Are you suggesting we both have sex with the same man?”

“Why shouldn’t we? We’re only going to be here for two weeks. It’s not as if we’re going to see the man again after we leave.”

“At the same time?” Stacy asked quietly.

“What do you mean?”

“Are you suggesting we both have sex with this man at the same time?”

Jenna thought about it for a moment. She never thought about a threesome before. It was new territory she wasn’t sure she wanted to venture into. “Well, maybe – “

“Oh – “ She couldn’t help but notice the disappointment in her best friend’s expression. Did Stacy want to do this? What would it hurt? If she was going to explore this side of her sexuality, she couldn’t think of anyone better than her best friend to venture into the experience with.

She turned to Stacy who busied herself with unpacking her clothes and putting them away in one of the dresser drawers. “We’ll do it,” Jenna said at last.

Stacy stopped and turned to face Jenna. “We’ll do what?” she asked in confusion.

“We will have a threesome with that hunky man,” she said with more confidence than she felt.

Stacy’s face lit up in a grin. “Are you serious? How are we going to do that? What if he’s not into threesomes?”

“Trust me. Most men fantasize about having wild, passionate sex with two very sexy women at the same time. He’ll jump at the chance.”

“But how are we going to get him into bed with us? We can’t walk up to the man and ask him to come back to our cabana and fuck us both.”

“I have a plan that might work.” Jenna waggled her eyebrows mischievously.