Lipstick & Stilettos

by Young, Tarra

  Passions Ink Press Presents

  Lipstick & Stilettos

  Tarra Young

  Copyright © 2012 Tarra Young

  All Rights Reserved.

  It 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.

  * * * *

  “You 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.

  * * * *

  “Isn’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.”

  * * * *

  Jenna & 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 admi
t 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.

  “What would that be?”

  Jenna couldn’t believe that she and her ultra-conservative friend were planning to do this, which meant the two of them, would be having sex with each other. Maybe there was hope for her best friend after all.

  “At dinner I will approach him and lure him back to our cabana with me. When you see us leave, give us about ten minutes before coming back here. Pretend to accidently walk in on us. All you have to do after that is leave the rest up to me. Do you think you can do that?”

  “Consider it done,” Stacy said, and then she did something that surprised Jenna, yet excited her at the same time. She walked over to where Jenna was standing and kissed her on the lips to seal the deal. It wasn’t just a peck, either. It left her feeling weak in the knees and lightheaded.

  * * * *

  An hour later they entered the dining hall. Jenna was wearing the most seductive outfit she packed for the trip. She wore a top that not only showed off her off her midriff, but low cut enough to showcase her ample breasts. Her skirt was so short if she bent over everything would be exposed to all the prying eyes staying at the resort.

  She decided at the last minute not to wear a bra or panties. She planned to tease their prey with quick peaks of her well-toned body.

  They spotted the man in question seated at a table surrounded by women vying for his attention. This wasn’t going to be as easy as they originally thought. Some of Jenna’s confidence began to plummet.

  “Are you ready?” Stacy suddenly asked.

  “It’s show time. Wish me luck,” Jenna said, her voice revealing her lack of confidence.

  “Are you kidding me? Dressed as you are at the moment, you don’t need any luck. The guy would have to be blind or gay not to be attracted to you, and we both know after today’s show, the man isn’t gay. You’re a really hot babe.” Jenna was seeing a whole new side of her best friend she never saw before. She loved what she was seeing.

  “Let’s just hope and pray I don’t fall flat on my face and break my neck in these spiked stilettos.”

  Stacy laughed. “Don’t worry. Just do your thing. Those other women over there throwing themselves on him can’t hold a candle to you.”

  They found an empty table and sat down. All around them couples fed each other and kissed between bites of food. Jenna was surprised and taken aback by everyone’s open displays of public affection. She didn’t think she could ever be that brazen.

  Stacy jabbed Jenna in the side with her index finger. Jenna yelped. “What was that for?”

  “Don’t look now, but Mr. Hunky man himself is headed this way.”

  Jenna fought the urge to turn and look. An attack of nerves came over her. What should she say to him? How did her hair look? What about her makeup?

  “Quick!” she whispered to Stacy. “How do I look? Honestly?”

  “You look smoking hot,” Stacy whispered back. A blush crept over Jenna’s cheeks and slowly worked its way up her neck. It would take some time for her to get used to her best friend talking to her this way.

  “Hello ladies,” a male baritone voice said. His voice was strong and powerful and set Jenna’s nerves on fire; causing her to long to let him have his way with her right here and now on the table in front of everyone. “I couldn’t help but notice you ladies.” He turned his gaze to Jenna. “I have wanted to get better acquainted with you from the moment I saw you earlier.”

  It was definitely show time.

  She smiled her brightest smile. “Would you like to join us for dinner?”

  “I’d be delighted to,” he said, pulling up a chair and sinking down onto it. He was taller than she originally thought him to be. She figured him to be at least six feet, two inches tall, if not taller. Jenna always found tall me to be attractive. She couldn’t help noticing he also looked more muscular up close. “By the way,” he added, “My name is Blain Sanders.”

  Who was Blain Sanders? She heard that name before, but where? There was something familiar about that name, but she couldn’t quite place her finger on it. “This is my best friend, Stacy Patterson,” she said pointing at Stacy, and I’m Jenna Taylor. Do I know you? Now that I can see you up close you look vaguely familiar and I’ve heard your name somewhere before. Excuse me if I’m being too forward.”

  “No, that’s fine. Do you read Lipstick & Stilettos Magazine?”

  “As a matter of fact, I do. I’m a subscriber. I never miss an issue. Why?”

  “I work for them as a photographer. I’m here to get pictures for the follow up article that will be appearing in the August issue.”

  Recognition came to her. She knew now where she saw him before. Each month the magazine spotlighted one of their employees. They featured Blain in their May issue. The photo of him that accompanied the article did little justice to the man up close and in person. “The May issue, that’s right.” Jenna said with a smile.

  Stacy squirmed next to Jenna and said, “I hate to admit this, but I haven’t read a single issue of Lipstick & Stilettos.”

  Blain smiled in her direction. “I can tell Jenna’s has passed on some of the fashion tips to you that she read about in the magazine.”


  “And how can you tell that?” Stacy asked, her interest seeming to be suddenly piqued.

  “Because both you women look very stunning, which is what drew me over to the two of you.” They both flushed at his compliment. “I even noticed you checking me out,” he added to Jenna, causing the heat in her cheeks to rise even more.

  Jenna recovered quickly. She needed to work on getting this man into bed with her and Stacy. It needed to be here at this resort because back home she would never consider a threesome. Here she could let loose and then go home in two weeks. No one would know what happened at this place except for her best friend and she knew Stacy would never tell anyone.

  Jenna leaned forward, giving Blain a clear view of her breasts. She saw him lick his lips. Good, it was working. Now she had his complete attention. “Mr. Sanders – “

  “Call me Blain.” There was no mistaking the desire in his voice. He wanted her. His obvious attraction to her spurred her on.

  “Okay, Blain. You mentioned you couldn’t help noticing Stacy and I. What was it in particular that you noticed about me?”

  He leaned forward and whispered in her ear. “I noticed how hot you look in that outfit and that you’re not wearing a bra or any underwear, for that matter.”

  She could feel the heat of his breath on her ear and neck. It danced across her skin like tiny little flames. A liquid heat surged through her and settled between her legs as she instantly felt her pussy become wet.

  He placed his hand on her knee and slowly slid it up her leg. His hand trailed up her skirt and touched her patch of wetness.

  One finger slid into the slick folds of her pussy, and then another. He began to stroke her, building a fire within her. She squirmed and bit her lip to stop the moan that was threatening to escape from within her.

  “I’ll be back,” Stacy said, getting up from the table. “I need to use the restroom.”

  This was Jenna’s cue. She needed to get Blain back to the cabana and into bed with her. “Would you like to go back to my cabana with me?” she asked after Stacy walked away.

  “Why? Aren’t you enjoying this?” he asked as he continued working his fingers through her slick wet folds like magic.