Lipstick & Stilettos (2 page)

“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.

* * * *

A
n 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.

“I’m enjoying this immensely. I just thought we would be more comfortable in my cabana where we can do a lot more.”

Desire sparked in his eyes. He pulled his fingers out and to her surprise he licked his hand right there in front of everyone. She didn't know why, but it turned her on even more.

“Lead the way,” he said when he finished. She practically jumped up from the table. She wanted this man more than she wanted any man. They left the dining hall and she led him down the path to the privacy of the cabana. There was no turning back now, not that she wanted to.

When they reached the cabana, she took the key out of her evening bag. She tried to insert it in the lock, but she fumbled with it and it nearly fell to the ground. He took it from her hand and unlocked the door for her.

Once inside with the door securely closed behind them, they wasted no time getting each other out of their clothes. She took his cock in her hand and stroked the length of it. He groaned and sank his hands into her long, blond hair.

As she was taking his cock into her mouth, she heard a sound outside the cabana. She knew it was Stacy, but nevertheless she paused for a brief moment. Blain must not have heard anything because he cried out for her not to stop.

At that moment the door flew open and Stacy walked into the room. She stopped and gasped. “I’m so sorry. I had no idea – “ She began backing out the door. The woman deserved an Emmy Award for her performance. When Jenna was about withdraw his cock from her mouth, Blain surprised her when he spoke up.

“Don’t go, Stacy. Close the door and get over here.”

Stacy did as she was told. When she was by his side, he pulled her to him and kissed her hard on the lips before sliding his hand up Stacy's tee shirt and cupped one of her breasts in his hand.

Jena was in a state of ecstasy. Watching a man kiss her best friend and fondle her breast, while at the same time she herself sucked his cock made her hornier than usual.

When he came close to coming, he pulled out of her mouth. It was then that Stacy, who no longer seemed ultraconservative, shocked her. She walked right up to her, and without hesitation, she kissed her full on the lips.

When she felt Stacy's tongue probing at her lips, she parted them for her and welcomed the invasion. Stacy's lips felt soft against her own. A heady feeling she had never experienced before came over her. She moaned and could feel her knees weakening. She probably would have fallen if it hadn't been for Blain coming up behind her and wrapping his arms around her.

She let out a sigh that ended in a gasp as his cock entered her anxiously awaiting pussy that was more than ready. Stacy stopped kissing her and took one of Jena's rosy colored nipples in her mouth and suckled it as Blain continued to pound his cock in and out of her pussy. She threw her head back and moaned.

She allowed her hands to slide up Stacy's shirt and to roam over the soft peaks of her breasts. She felt her best friend take a sharp intake of air right before a soft moan escaped her lips. Just hearing the impact that her touch had on Stacy, made her more bolder. She slid her hands down to the waistband of Stacy's pants. She bravely dipped her hands down them and allowed her fingers to enter into her awaiting pussy. She was surprised how slick Stacy was as she worked her fingers into the folds.

She continued fingering Stacy's pussy while Blain continued pumping in and out of her. It wasn't long before they were both crying out as their orgasms took them over the edge.

Stacy was soon crying out herself as she drenched Jena's hand. When the orgasm that was rocking Stacy's body and throwing her over the edge subsided, Jena withdrew her hand. While looking into her best friend's eyes, she licked her hand clean. When she finished, she kissed Stacy, allowing her tongue to explore the recesses of her mouth, the way Stacy's tongue had her own right before she had the most incredible sexual experience of her life. It was one she would never forget.

As soon as Blain got his breathing under control, he had Stacy out of her clothes. He instructed her to lie down on the bed. He told Jena to climb on top of Stacy so that her crotch was in her face.

Confused about what was going to happen, Jena was surprised when she felt Stacy's tongue dip into the wet folds of her pussy and begin to lick her all the way up and down.

She was completely mesmerized as she watched Blain sink his cock into her best friend's pussy which was still slick with juices. From this position she could see each stroke of Blain's cock as he plunged it in and out. Jena moaned, enjoying the sensations Stacy's tongue was creating as she ate her out.

When it was all over, the three of them collapsed in a heap on the bed. Their breathing was labored. This was definitely an experience she would never forget.

* * * *

T
he next morning when Jena awoke, Blain was gone, but Stacy was still there, snuggled close. Her head rested on Jena's chest as she slept.

Reality of the situation hit her like a ton of bricks. After last night, what would happen to hers and Stacy's friendship? Would they really be able to go back to L.A. and pick up on their friendship and their lives as if last night never happened?

Jena wasn't a lesbian. She loved men too much, but after last night, where did that leave their friendship?

The thought of not having Stacy in her life scared her. Stacy had always been there when she needed someone. She was a shoulder to cry on in bad times, and she was someone to laugh with during the good times. Who else would she be able to sit and eat a carton of Ben & Jerry's Chunky Monkey ice cream with after yet another failed relationship? A feeling of guilt washed over her. How could she have let things go this far? She had to admit though; she enjoyed it, but was it worth the price she might have to pay now? The loss of her best friend?