Lipstick & Stilettos

by Young, Tarra

  “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.

  * * * *

  The 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?

  She didn't want to think about that. She climbed out of bed, careful not to wake Stacy. She needed a shower. Her muscles were sore from the wild night of sex she had just experienced mere hours ago. She stepped into the shower and let the water run over her. It felt good on her stiff joints and sore muscles. She was reaching for the shampoo bottle when she heard a sound. Someone entered the bathroom. Jena froze as she listened.

  The shower curtain parted. Stacy stood smiling at her. She looked Jena's body up and down appreciatively. She felt her body respond. How could she feel such strong guilt, and yet feel such a strong desire to be with Stacy in an intimate way again?

  “Mind if I join you?” Stacy asked seductively.

  Her body screamed yes, but she knew in her heart it was wrong. She was confused. What did she want? She knew she didn't want to have all this tension between her and Stacy.

  “Well-“ Stacy prompted her. In the end her mind won out. She couldn't allow herself to give into Stacy's advances until she knew for certain what she wanted. The last thing she wanted to do was hurt her best friend's feelings.

  "Stacy, don't take this the wrong way, but I'm going to have to decline.”

  Jena could see the sadness in Stacy's eyes and she nearly gave in and invited her into the shower. Stacy turned to go, but Jena stopped her.

  “Can we please talk about this after I get out of the shower?”

  “Sure,” she said.

  Stacy went out, closing the door behind her. Jena felt like dirt. She had just done the last thing she wanted to do. She hurt Stacy's feelings by rejecting her. How was she going to fix this without giving in?

  When Jena got out of the shower, she pulled on a big, white, terry cloth robe provided by the resort. When Jena went out of the bathroom, she found Stacy lying on her bed reading the latest copy of Lipstick & Stilettos she left lying on the dresser. How was she ever going to be able to tell Stacy the night before with her had been a mistake and it couldn't happen again, at least not until she knew for certain what she wanted without hurting her any more than she already did?

  She wasn't a lesbian and she never really thought of herself as bisexual either. She enjoyed her first sexual experience with a woman, but she still enjoyed sex with men. There were so many things she needed to sort out in h
er mind before she would know for certain about her sexuality and what she really wanted. She sat down on the edge of her bed.

  Then something occurred to her she never realized before. Was Stacy bisexual? She sure seemed experienced the night before as if she had done this sort of thing before. She seemed to know more about what she was doing than Jena did. She knew Stacy wasn't a lesbian. She had plenty of boyfriends, and she dated a lot of guys between relationships. She sat down on the edge of her bed facing Stacy. “Can we talk now?”

  “Yeah, sure we can.” She laid the magazine down and sat up to face Jena. Panic seized her. She hoped it wasn't too late to fix the damage caused by taking their relationship to an intimate level.

  What if it was beyond repair? She pushed the thought away. She couldn't be thinking such thoughts. She needed to fix things between her and Stacy, no matter what it took. That's all there was to it.

  She reached out and took both of Stacy's hands in her own. “Before I tell you what I need to, there's something I need to know. Are you bisexual?”

  Stacy jerked her head up and looked at Jena. She was quiet for a moment before she asked, “Do you want an honest answer?”

  “Yeah, we've always been able to be honest with each other before this.” Stacy looked reluctant, but finally answered.

  “Yes I am.” She looked away as if she were ashamed.

  “How long have you known?” Why hadn't Stacy shared this with her sooner?

  “For about five years now.”

  “Why didn't you tell me?”

  “I was afraid you would stop being my best friend. I still am afraid of that.” She could hear fear in her best friend's voice.

  “Never! I want you and I to be best friends forever.”

  Stacy turned to look at Jena. Surprise was written in her expression.

  “Really?”

  “Yes. Remember how we used to pass notes to each other in school and sign them off: best friends forever?”

  A smile formed on Stacy's face. “Yes.”

  “Well, when I signed my notes that way, I meant it.”

  “Why did you turn me away when I asked you if I could join you in the shower? Didn't you enjoy last night?”

  “I’m just confused about my own sexuality. I have to sort a lot of things out in my own mind. Don't take any of this personal. It's me, not you.” Shit! She remembered saying the last part of that to her last boyfriend. She never thought she would be saying those words to her best friend.

  Stacy squeezed her hands reassuringly. “I understand. No pressure.”

  There was a knock at the door. Jena wondered who it could be. She released Stacy's hands and got up to go see. It was Blain. “Good morning, beautiful. I was hoping I would be able to catch you before you went out today.”

  Jena smiled. She was still deeply attracted to Blain. She loved how the white shorts and tee shirt he wore fit tight enough to outline his muscular frame. She longed to run her hands over his chest, but she contained herself. “Good morning. Is there anything I can do for you?”

  “As a matter of fact you can. I came here to ask a favor of you.”

  “Just name it.”

  “Do you think we could go somewhere to talk?”

  “Just give me ten minutes or so to get dressed.”

  “I’ll be back then,” he said with a wink.

  He turned and walked away. As soon as he was out of sight, she closed the door and made quick work of getting dressed in a pair of shorts, a halter top, and a pair of flip flops.

  * * * *

  Fifteen minutes later Jena lounged out by the pool with Blain. She did her best to ignore the open sexual acts openly going on all around them.

  “So what's that favor you mentioned earlier?” she asked him once she situated herself on the lounge chair. She began rubbing sun screen over all the exposed areas of her body.

  “As you know, I'm a photographer for Lipstick & Stilettos Magazine.”

  “Yes, I'm aware of that.”

  “Well, the model we hired canceled on us at the last minute and left us in the lurch without ample time to get a replacement to fill in for her.”

  “That's too bad,” she said wondering where he was going with this.

  “I was wondering, and I hope you'll say yes, if you'll fill in for her.”

  “Are you suggesting that I model for you?”

  “Yes, it would mean a lot to me.”

  “I really am tempted to say Yes.”

  “Then you'll do it?”

  “As I said, I'm really tempted, but I have no training or experience in modeling.”

  “There's no need to worry. I'll walk you through it and tell you what I need you to do. Will you do it?” He quoted a salary that would replenish her savings account and more than pay for this trip. How could she say no?

  “I’ll do it,” she said after some thought.

  “I knew I could count on you. We'll get started on the photo shoot right after lunch if that is convenient for you.”

  “After lunch will be fine.”

  She looked up and saw a hungry look in his eyes. He got up, came over to her, and bent down to kiss her. Her body came alive under his touch. He lowered the weight of himself onto her. A soft moan escaped her lips as he began to explore her body with his hands.

  When his hands worked their way up to her breasts and began to stroke them, she realized what was happening and where they were. “No, Blain,” she said as she took both her hands and pressed firmly against his chest. “We can't do this out here in front of everyone.”

  He rose up and sighed. “Would you be more comfortable if we went to my cabana?”

  “Yes.”

  He stood and held out both his hands to her. She reached up and grasped them. He pulled her to her feet. He held her hand as they walked. It felt natural to be with him.

  Once they were in the privacy of his cabana, he led her over to his bed. He lowered her down before lowering himself on top of her. He nibbled her ear and worked his way down to her neck where he trailed kisses that felt like small flames licking at her skin. Hot desire flooded her pussy.

  She slid her hands up and down his solid back, before moving lower and adjusting them so that she was cupping his hard cock through the fabric of his shorts. She began rubbing it. He let lose a deep moan.

  She began moving her hands up until she reached the waistband of his shorts. Reaching her hand down his shorts, she reached in and pulled out his rock hard cock. As she began to stroke his cock, she felt it begin to throb beneath her touch.

  He stopped kissing her. “I think it's time for you to stop before I shoot my load.” She smiled a devilish grin as she continued to stroke it. “At least let me stand up while you kneel in front of me.”

  She finally let go of his cock and he got up. She stood up and knelt before him. She stroked the length of his dick before she slid it in and allowed him to fuck her mouth.

  Moments later when she sensed he was close to coming, she slid his cock out. When he came he cried out. It splashed all over breasts and in her face.

  He wasn't finished with her yet. He took her in his arms and lowered her to the bed. He covered her with the weight of his body. In one swift move he sank his cock into her pussy.

  He began to drive in and out of her. The man was an expert when it came to pleasuring women. She clung to him as the heat between them built up to a burning inferno. They both cried out simultaneously.

  Jena's body rocked with the most powerful orgasm she ever experienced. Where had the guy learned to fuck like that?

  * * * *

  “So what did Blain want?” Stacy asked an hour later when Jena returned to the cabana after making love to the man one more time. She needed to freshen up and get ready for lunch.

  “He asked me to model for him. One of their models backed out at the last minute without warning.”

  “That's wonderful news. Did he tell you what you are going to be modeling?"

  Jena realized she ha
d been so excited about the job offer she forgot to ask about the specific details such as what she would be wearing in this photo shoot.

  “No. I didn't think to ask.”

  “You better hope this isn't a nude modeling job.”

  “I doubt I'll be doing any nude posing anytime soon.”

  “How can you be so sure about that?”

  “The photos he takes are to be used in Lipstick & Stilettos Magazine.”

  “You are so lucky,” Stacy said with a sigh. “So when does this fantastic opportunity take place?”

  “I was thinking after lunch today.”

  “That works out perfect. I have an appointment at the spa today for an afternoon-filled session of pampering.”

  “After this photo shoot, I might just spend my evening there getting the royal treatment myself.”

  Jena looked at her watch. It was later than she originally thought. “I need to hurry and get ready to go,” she said as she rushed into the bathroom.

  * * * *

  When Jena and Blain arrived back at his cabana after enjoying a nice lunch in the dining room, Blain handed her a bag. “You can go ahead and change into that.”

  She opened the bag and pulled out the skimpiest bikini she ever saw along with the signature spiked Stilettos and shade of lipstick used by all the magazines models.

  When she turned to walk into the bathroom, he asked, “Where are you going?”

  “I’m going into the bathroom to get changed.”

  “You can change into it right here.”

  “Oh, okay.” She was nervous, but she didn't know why.

  “Don’t you think it's a bit too late for you to be acting all modest around me.”

  She giggled nervously. He made a point. She began stripping out of her clothes while Blain fiddled around with the camera equipment.

  She slipped into the bikini, slid on the Stilettos and put a coat of the shiny metallic red lipstick on her lips, the official trademarks of the magazine. He looked up at her a few minutes later. “Ready?”

  “Yeah. Where do you want me to stand?” She looked around nervously.