Bridesmaid for Hire

by Chance Carter

  “Brad?”

  “Yes.”

  “I am starting to really like you.”

  “Thanks, I’m really liking you, too,” he says.

  “I think we’ll have some fun this week.”

  “Me, too. I’m glad you’re with me.”

  “Thanks.”

  They stay in a place of silence, not sure what is supposed to come next. Jane leans back in the chair and watches the clouds through the window.

  “What’s the craziest thing you’ve ever done?” she asks him.

  “In what way?”

  “Craziest, wildest, something so bold nobody would have thought you would ever do anything like it.”

  Brad is not sure if he wants to share that truth. He’s done a lot of things, and the last thing he wants to do is give her the impression he is some kind of player or that he’s dangerous. Money just provides a whole lot of freedom, and he’s let himself push his limits because of it.

  “Well, I don’t really know what to tell you. Craziest adventure or craziest sex?”

  “Well, now that you mention it, both.”

  “Ohh. Hmmmm… I’ll start with craziest adventure. I did a 24-hour binge one time where I travelled to Australia to swim with sharks, then went to Thailand to learn about snake charming, and then did a fire-breathing class on the beach. That was probably the craziest 24 hours of my life. And yes, alcohol and drugs were involved.”

  Jane’s eyes went wide open.

  “For real? You did those things?”

  “Yes, and I lived to tell the tale.”

  “Thankfully!” Jane says, still shocked. “I’m not sure now if I still want to hear about your craziest sex.”

  “Let’s just say it involved five women, five hours, and lots of fluid,” Brad says, not wanting to share all the details.

  He has banked on the fact that Jane probably hasn’t heard much about sex play.

  Jane put her hands up to her ears, shaking her head and smiling.

  “I don’t want to know,” she half jokes. “It’s too much for my innocent ears.”

  “Yes, I agree,” Brad says, smiling. “No need to know all the juicy details. Yet…”

  Chapter 16

  Jane leans back in her chair yawning, and tells Brad she’s going to take a quick nap. She covers herself in a blanket and curls up into a ball.

  Brad notices how sweet she looks, and replays their exchange so far. She is so easy to be with and clearly isn’t trying to impress anybody. He would never want to hurt her or make her feel uncomfortable.

  She reminds him so much of Kelly, and has to keep remembering that Jane is a different person. With Kelly, he’d just go over beside her, cuddle up, and hold her until she fell asleep. Then later he would play with her nipples until they were hard, tickling her clit until it stood up, then kiss her body until it was tingling.

  He’d stroke her pussy until it was all nice and wet, waking her up in the midst of a mind-blowing orgasm. He would do that all the time with Kelly, and she loved it.

  They’d had a great sex life and would fuck anywhere they got the chance. In the back of their friend’s cars was a frequent favorite. Or she would give him blow jobs at the office building owned by his parents, right in the middle of the executive boardroom. She’d even sneak him into her house at night where he’d come into her bedroom and they’d have the craziest orgasms while having to be totally silent so her parents wouldn’t hear them. He’d leave her in her bed, feeling raw and exhausted, with his come all over her belly and tits, while he sneaked back out the door. Somehow, they never got caught.

  Those times with Kelly were so special. They naturally fit together and trusted each other. They could go anywhere together and both knew they were made for each other.

  What he wouldn’t do to have that feeling again. That feeling of being completely relaxed with a woman, like playmates taking on the world and making it a shiny and happy place to be.

  He hopes Jane will be that to him. He wants to show her Paris and have someone paint her portrait. He wants to take her to Iceland where they get a private spa experience and have wild, passionate sex in the hot springs. Or he could rent out the National Art Gallery, so they can fuck in front of a Monet painting while covering each other in champagne and chocolate sauce.

  He wonders if Jane will ever be that wild of a woman. It could be even better with her than it was with Kelly, because now he had money to play with and no parents to sneak around.

  Jane tosses and turns in her chair. Brad clearly sees she’s having a dream, judging by the way her eyes are moving quickly around under the tender lids. Is it a good dream or bad? Is she dreaming about him? He can only hope, but can’t tell. She starts swaying and her head nods down to the side.

  Jane is lost in a place that feels like a different world. She is dreaming she is in a garden in the middle of the night, and is wearing only a see-through negligée. It’s all white and goes down just to the top of her thighs. She has white, satin panties underneath, and the cool breeze is flowing through it and up her body.

  She is walking around barefoot in the field, and she can feel the dew on her feet. It all feels surreal and magical. She is lost in this dream, but somehow doesn’t feel that way. She is looking for something and just going wherever she is pulled to go.

  She sees a water fountain and splashes water all over her body. In the reflection, she notices the presence of someone behind her. She is terrified and frozen for a moment, unable to run anywhere. She feels this person come closer and closer behind her. She wants to scream, but she can’t.

  Then she feels hands on her back, and at first, she is ready to run, or to fight, but then she realizes these hands are safe and warm.

  They are the hands of a man, and they are lifting up her lingerie and rubbing around her lower back. She has no idea who this is, and she doesn’t care.

  It feels so good to have a mystery man touching her. She can feel his breath on her neck, and his one hand reaches around to her right breast, massaging it to turn her on. Then his other hand reaches down her ass, and he starts playing with it in a way no one ever has before.

  She reaches down with her hand and starts stroking her pussy while he’s finger fucking her ass. Who is this man? Who cares? It feels so good. She starts moaning and getting wet in her dream. She looks in the mirror and sees that it’s Brad.

  She wakes up, startled, and wonders if Brad really is touching her body. She looks over and sees Brad is across from her. He hasn’t been touching her, but part of her wishes he would have been. Her panties are so wet, as if she came in them. She’s nervous, wondering if he was watching and knows she just had a wet dream about him.

  “Wow, I had the craziest dream,” she said, fishing to see if there was anything she should be worried about.

  “I noticed,” he said, not setting her mind at ease at all. “You were moaning a lot.”

  “Crazy. I think I need to go to the washroom to freshen up.”

  “I’ll save your seat,” Brad says and winks.

  He can smell her juices in the air, and based on her moaning, he suspects she was dreaming about sex. He’d love to take a chance and start something up in the bathroom with her while she’s still horny, wet, and out of her senses, but he wants her to come to him when she’s ready, and not feel like he’s pushed himself on her.

  Damn, she’s one sexy creature. I can’t wait to get a piece of her sweet ass.

  Chapter 17

  Brad is hopeful that she’ll be awhile cleaning up her wet mess and trying to compose herself. He unzips his pants and starts stroking his cock, barely able to contain himself. He is so hard, he’s ready to explode all over the place, and has been that way for so long. He wraps it with his hand and pulses up and down really fast, imagining it is Jane riding on top of him, her hair down, swinging with abandon all over her tits.

  He wants to grab her hips and fuck her back and forth, up and down, side to side, anything to get her all worked up and
to show her how he can pleasure her, and give her an idea of how much she turns him on.

  He thinks of her getting wetter and wetter, moaning and breathing so hard she can’t catch her breath, then screaming so loud the pilot can hear them, making him jealous knowing Brad is fucking her hard. He saw how the pilot checked out her ass, and that ass will be all his.

  Brad continues, imagining that just as he would be ready to come, he’d pull her off his cock, jack himself, and shoot come all over her tits and belly so it drips down into her pubic hair. Then he’d have her suck him until there was nothing left.

  With that thought, Brad comes all over his cock and it shoots over to the other side of the seat where Jane has been sitting.

  God, I wish I could just have her now.

  He hears Jane come out of the bathroom, so he rushes to put his cock in his pants, then wipes the seat down with soda water and his napkin while wiping his hands at the same time.

  Jane walks back over and Brad feels like he’s going to lose his mind at how horny he feels for her, even though he just jacked off.

  “So, how comfortable are you with dressing up?” Brad asks, trying to divert his deeper urges.

  “Well, I’m a ballerina, aren’t I?” Jane replies. “Ballerinas are all about dressing up.”

  “That, you are,” Brad agrees. “So, perhaps you won’t mind some of the things I’ll be asking you to do this week. Are you wearing the lingerie underneath your dress right now, for example?”

  Jane’s face flushes beet red, unsure of how she wants to respond, given she just had a wet dream with Brad in it.

  “Uh, yes, I am.”

  “Do you like it? The lingerie? Does it fit? Does it feel good?” asks Brad, fantasizing about how it looks under her dress.

  Jane feels her pussy heating up and squeezing again just from his words and tone of voice. God, he has some kind of spell on her.

  “Yeah, it’s a perfect fit, actually. I really don’t know how you figured that out, quite honestly. Especially the bra.”

  Brad imagines her in the bra, how it barely covers her nipples and outlines the contours of her breasts.

  “Let’s just say, my personal assistant has a good eye. She checked out your size when she went to the change room to meet you.”

  “Oh, so that’s how you did it! Clever. Very, very clever!” replies Jane. “What other tricks do you have up your sleeve?”

  “Not many. It’s really all my personal assistant. I can’t take any of the credit,” Brad smirks.

  “So, back to your question about dressing up,” reminds Jane.

  “Right. So, how comfortable are you with wearing different styles of clothing, maybe something out of the ordinary?” he asks, seeing how far he can take it with Jane.

  “Well, it all depends. I’m still a bit of a modest woman, but I did dress for you today, didn’t I?” remarks Jane.

  “True. Well, the reason I ask is because every day you will be given instructions to wear something. It may be underneath your clothes, or a dress, or anything else. I love to watch a beautiful woman wear different things,” he says, staring at her a little bit longer.

  Jane still can’t take in that he finds her beautiful. “Well, we’ll see, but it sounds pretty harmless. Though, you may need to find a beautiful woman somewhere,” she partly jokes.

  “Jane Bryden, what will it take for you to see who you are?” Brad shakes his head.

  He reaches for her hand to invite her to stand up. There is a mirror on the closet door. “Come. Take a look at yourself.”

  He stands behind her while they look in the mirror. He strokes her hair.

  “Do you mind?”

  Jane shakes her head gently to indicate that it is okay.

  “Jane, do you not see how beautiful you are. Your lips are delicate. Your nose is perky and precious. The outline of your face is just amazing.”

  He strokes the side of her face and Jane wants to nestle her head right into him.

  “It’s like you are a porcelain doll. Just perfectly precious. Simple. No airs about you.”

  Jane looks in the mirror at herself, as if for the first time. She sees a bit of what Brad is talking about and is stunned. She has never thought of herself as beautiful, not ever.

  Brad reaches down and lightly kisses her neck, then walks away so as not to pressure her. Tingles shoot up her neck and she wishes his lips would linger there forever.

  Chapter 18

  “Okay, so here is how it works,” Brad begins. “I will give you an envelope for our first day before we leave this plane. You will get one envelope for each of the seven days we’re together. All I ask is that you follow the instructions inside. For some days, there will be a piece of clothing I’ll ask you to wear, sometimes a bit more risqué than perhaps you’re used to,” he says, trying to ease her into it.

  “What does clothing matter, anyways?” replies Jane, pretending to not be as nervous as she feels inside. She can only wonder what he’s planning for her. A bikini? Black leather? A show girl’s outfit? Her mind is running wild, and she wonders how she would look and feel in each.

  “How bad could it really be? I’m used to a bit of performance, and we’re on vacation, aren’t we?”

  Jane takes a sip of champagne, realizing she’s almost willing to do anything for a million dollars at this point. If she’s tipsy, it may not even be that big of a deal if she sleeps with him. In fact, she’s starting to think she would like it.

  “And Jane, please know at any time, you can let me know if you’re uncomfortable. You know that, right?”

  Jane nods. “Yeah, I think I’m getting it, Brad. I trust you, for some reason.”

  “Good. That’s how it should be. And you know, Jane, I need to put it out there that I’m very attracted to you, and I hope we do get to be together for more than just as a business arrangement, if you get my drift, but I understand if you don’t feel the same way.”

  Jane is kind of taken aback, though she’s not surprised. They did kiss, there were sparks, and she’s been feeling his sexual energy since she got on the plane. She’s never had a man be this direct with her, ever, and she’s not sure how to respond.

  “Well, we will have to see, won’t we, Brad?” replies Jane, with a strange sense of self-assuredness. “We never know what the week will bring.”

  Brad likes this side of her. This virgin in her who is also confident in herself and kind of flirty, like she’s rehearsed her lines from T.V. shows.

  He gazes at her with a longing inside of him, waiting to see if maybe she would be open to even a kiss. He’s learned to never be forceful with women, or to make assumptions, instead waiting for that signal that shows she wants something more.

  He reaches out his hand, hoping she’ll respond to the invitation. She complies and he holds her small hand in his grasp.

  “You know I would never want to hurt you, Jane. You are very special, and I know you’ve never been with anyone before, so I don’t want to scare you away or make you do something you don’t want to, okay? It has to be something you want to do in your heart. Alright?”

  Jane feels his sincerity, and it makes her feel even more at ease with him. She takes a breath of relief, grateful that she doesn’t have to feel the pressure of performing for him. He feels her hand calm down in his, and it relaxes him as well.

  He strokes her hand to reassure her, making her feel safe, held, and comforted all at the same time. She loves his large hands. He is a man who takes care of so many important things in the world, but all he wants to do now is sit here and be with her.

  He lifts her hand and kisses it gently. “I’m really looking forward to getting to know you, Jane.”

  Jane smiles with a tenderness in her eyes.

  “I’m looking forward to getting to know you, too.”

  Just the way he touches her sends tingles up her arm and neck. She wishes he would kiss her hand, then make his way up her arm, then kiss, lick, and suck on her neck, going around and fi
nally kissing her on the mouth.

  Before meeting Brad, she had only been kissed once before, by Jimmy, that guy she worked with who lied about not having a girlfriend. He was two years older than her when she was only 15. She was working at the local restaurant and they were in the basement getting supplies. He claimed he had a crush on her, and she was confused but flattered enough to let him kiss her.

  They spent about two minutes playing with each other’s tongues and biting lips, as awkward as most teenagers are. She thought she was a special girl in Jimmy’s eyes, then found out the next day he had a girlfriend. She never trusted boys after that and just stuck with her studies.

  But with Brad, she really does feel what he’s telling her is true, and she would love nothing more than for him to woo her, put those gorgeous lips on her, and kiss her so deeply she can hardly breathe.

  After he kisses her hand, he looks up and continues to hold it.

  “I hope you will have the best time of your life this week, Jane Bryden. You of anyone deserve to have a break like this. You are one beautiful and unique young lady, and I want you to walk away knowing that with every ounce of your being.”

  Tears of joy and love start welling up in Jane as she is really beginning to feel how special she is.

  “So, here is the first invitation for tonight.”

  He hands her the card.

  She opens it and reads it out loud. “Go to your hotel room. You will notice a bag with a dress in it and a pair of shoes. Put them on and meet me at the hotel restaurant at seven sharp. Don’t be late.”

  “Well, that seems easy enough,” Jane comments. “I will accept your invitation,” she says, smiling back.

  “Wonderful,” Brad replies. “I am glad you will be my dinner guest.”

  Chapter 19

  They arrive at La Casa Cabanas, a gorgeous, small hotel on the edge of the turquoise sea where only high profile guests are allowed to stay. It has a strict, low-noise policy and people can hang out at the outdoor bar on hammocks sipping cocktails made from freshly picked fruit.