Jayden and Claire

"Remove your underwear", he said as he reached out with the money in hand.

Excitement and confusion raced through her mind. She had too many ideas and not enough direction on how to proceed. Should she slide her pantie off right here or rush off to the bathroom and do it. If she accepted the money, which she already knew she would, she would be naked in his presence. Deep down, she knew that this was going to be the case. She also was enjoying it a lot more than she believed she could.

In a move that surprised her when she thought about it later, she took the money, took a step back and turned around. She slowly bent at the waist and lowered her underwear down past her knees. The bend accentuated her behind in such a way that she knew Jayden was reaction without needing to look back at him. At this moment, she felt powerful. She was controlling this moment with this tiny movement as she first lifted one leg then the other out of the remaining garment.

Jayden leaned back and enjoyed the show. This was something he had thought about for a very long time. He knew that one day he would get the pleasure of seeing her without clothing, but he was pleasantly surprised it happened this evening. If truth were told, he believed that she would have stopped with the first twenty for showing up. He also thought that she would have stopped before the bra. Jayden would have to ask how close she came to stop this before now. He knew that this might be the furthest she would go.

As Claire walked slowly to the restroom, she resisted the urge to look back. She wanted to know how focused Jayden was on her and her body as she strolled naked through his living room. She clutched tightly on her underwear to maintain her focus.

As she reached the bathroom, she threw her underwear on top of her clothes and put the money with the rest. She took her time looking in the mirror. She reacted with both confidences and with being unsure about herself. As most women do, she was noticing the things about her that she didn't like and started getting off balance. She started thinking some more and realized that she was standing naked in Jayden's house and only had seventy of the one hundred dollars.

"What more could he want from me?" She thought to herself. "There is a big amount of money left and I am already nude." As that thought raced through her mind, she heard movement from the other room. She took a few moments to compose herself before she left the bathroom.

When she returned, she noticed that the table was mostly cleared save for two glasses of wine. He had refilled his glass and when he noticed Claire returning, a little less sure of herself, he asked if she would like a splash more wine. She nodded in approval as she nervously bit her lip.

She sat down and nervously sipped as he sat back and relaxed. He took a big drink out of his before putting it down. The most unexpected thing happened. They started talking. What they talked about didn't matter much, but it was just like they would do at the coffee house or on the phone. Trivial stuff really which at first unbalanced Claire, but after a while, she felt as comfortable as she always did talking to her friend.

It was easily half an hour later when he reached into his pocket and put the remainder of the money on the table. Claire so lost in the conversation, she almost forgot that she was nude. It struck her that Jayden wasn't leering at her or looking at her in a way that made her feel uncomfortable. In fact, she was more comfortable before seeing the money than she had been in a while.

"This is the one that will most likely push you out of your comfort zone. So much so, in fact, that the money will stay on the table until you are done. If you fail to complete this, I will keep the money." When asked if she understood, she bit her lip before nodding that she did.

He continued. "Good," he replied. He pulled out his phone and set a timer for ten minutes. He sat it on top of the money without starting it. "Without making it much more uncomfortable than it already is for you, I will be very blunt in what I want. I will give you a few moments to think about it. If you agree, I will start the timer when you are in position. If not, go to the bathroom. You may shower before you get dressed if you want. I will remain, and we can hang out for the rest of the night."

"I want you to go to the middle of the floor, get on your knees, and with your ass facing me, I want you to tease, and perhaps please yourself for ten minutes. I won't give you any more instruction than that. I won't tell you what to do or how to move once you start, so this is your show. Do you understand?"

She bit her lip a little harder before nodding this time. Thirty dollars for ten minutes did sound wonderful. The little things she could do for herself would be nice. However, this was a level of intimacy that she didn't want to share with any but a select few. Part of her wishes she could think, "why not?", but that was so against how private she preferred this part of her life to be.

She also realized that if she knew this was going to be the endgame, she wouldn't have agreed to this at all. At this point, she was ahead seventy dollars and most of her screamed that she should take the money and run. There was a small part of her, however, that was excited at the idea. She wasn't attracted to Jayden, at least not in this way. The thought of revealing this private part of herself started to feel intoxicating. She only needed to be brave for a moment, because she knew that if she started, she wouldn't allow herself to stop; not until he earned the rest of the money.

Jayden poured himself some more wine and sat back. He knew of this dilemma with her. He had tried more than a few times to seduce her, and each time failed. This didn't stop him, however. Half of the fun of flirting is the chase. Even if she said no forever, he would probably still try.

But that wasn't what this was about. It was about pushing her beyond her comfort for his enjoyment. It was seeing what she would do for money and enjoying every bit of this experience. He sipped from his glass and relaxed a bit. He knew that getting worked up just before would make her more apprehensive. He did want her to be as comfortable as she could be in this uncomfortable situation.

As one song ended, and another started, she rose slowly and started walking away from the couch slowly. She was taking her time knowing that one way or the other, she would have a regret from this; either she would share this part of herself with Jayden (something she had never planned) or she would get dressed and miss out on eating well during her breaks at work for about a week.

She was halfway to the bathroom, sure that would be the best decision when her body began to ache slightly. She didn't know where this ache came, but she knew what it was. This was going to make the decision that much harder. She did enjoy this attention. Especially from Jayden. She wanted to be able to throw away her worries and doubts about what Jayden would think afterward and just begin. She didn't want the relationship to change with them, as any relationship seems to change at any inclination of a sexual relationship.

She wanted to feel Jayden wanting her. Wanted to see his unbridled lust as she put on a special show. Just for him.

She also remembered that it wasn't just for him. It was for the money as well. That would help. It would make this a bit more impersonal than intimate, even though he was asking for the most intimate of acts.

She slowly dropped to her knees as she got halfway to the restroom, spreading them slightly for balance as started slowly running her hands and fingers under her breasts. She heard the small beep from his phone as he must have started the timer. Claire had reached the point of no return.

She began cupping her breasts, teasing them as only she knew how. Anticipating her own next moves and getting lost in her mind as her fingers gently caressed her nipples. Giving them a gentle squeeze, a small gasp of pleasure escaped her mouth.

After a few moments, one hand slowly worked its way up her neck towards her face, caressing it before her fingertip reached her mouth. She gently pulled down her lip before licking the tip of her finger. The other hand started moving downwards, slowly over her stomach and hesitating only slightly before it made its way over her small mound. Instinctively, one finger shot a bit further down and teased her slit.

As one hand started to tease and rub just above her clit, she slowly started sucking her finger into her mouth. Claire sucked gently on her finger which seemed to send shivers down her spine. She slowly pulled her finger out her mouth and brought that hand back down to her breasts, using the wet finger to tease around the edges of her nipple, feeling it stiffen even more with the attention.

She spread her legs slightly for both balance and to ease her access. She felt her finger slide down her slit and enjoyed the release she felt building. When her finger reached the opening of her pussy, she started leaning forward, pushing her ass in the air. She was engrossed in herself that she barely heard the small gasps and moans from behind her as she focused on herself. She continued to lower herself so that she was supported by one hand while the other explored her enjoyment.

Jayden was pleasantly surprised. He knew that she was going to call it off before it got this far. Yet, he was so lost in the show that he almost forgot the reason she was there was to earn the money. For now, it didn't matter. He was experiencing the show that he had wanted to see for quite a while. He knew that he had to keep himself in check to make sure it wasn't weirder than it was already.

He leaned back on the couch and adjusted himself so that he was comfortable but made sure he kept his hand out of his pants. He started massaging himself through the fabric, starting to feel the familiar drops of precum easing out of his cock. Jayden stroked himself, keeping his eyes on the show, knowing that he would have to take care of his excitement when the evening was over. Until then, he was content outwardly stroking himself to the wonderful display.

Claire bent the arm that was supporting her so that she could lower herself a bit more as her legs spread, giving her more access to her slick opening. She pushed the tip of her finger inside and gave out a very audible moan. She didn't care anymore. She was lost in herself. Exposing herself as such gave her a bit more of a thrill than when she did this on her own. She knew that if it weren't for the arrangement that put her in this position, she would never be here. Yet, she hadn't remembered being this excited in a very long time.

She arched her back a bit more, losing herself as she pushed the finger a bit further inside her, working herself slowly with strokes as her finger would allow before slowly withdrawing it and rubbing the juices all over her lips. Taking the wet fingertip, she started rubbing her clit slowly, feeling it as stiff as she could possibly remember. This action caused a simultaneous arch in her back and gasp escaping her mouth.

She then pushed the finger back deep inside her pussy and felt even more wetness than she remembered having. Being exposed and showing this part of her excited her more than she could believe.

Lowering herself so that her shoulder was on the ground, it gave her access to her other hand. She used it to reach between her legs and give herself the double pleasure of outer and inner stimulation. The second she felt her finger inside her as the other one touched her clit; her legs began shaking slightly at the first small rush of an orgasm started. She continued to do this as wave after wave of pleasure washed over her. Finally, it started to subside. She had removed her finger from her pussy and started rubbing her slit with two fingers. She felt the tips of them next to her opening. She was ready to slide the fingertips in when the alarm sounded.

She hurriedly came back to reality and thought about her situation. She was on the floor, completely exposed and had experienced a few orgasms in front of her friend. Claire turned to look at Jayden and saw him leaning over to pick up the phone and shut the alarm. Returning to her full height from her knees, she felt her legs a little weaker than she expected, but finally made her way to stand. She kept Jayden's eyes in hers as she made her way to the bathroom.

She looked at herself in the mirror trying to decide what and how she felt. She knew that she shouldn't have done this. She tried to convince herself that she did it solely for the money and most likely wouldn't do this ever again in front of her friend. However, she knew that she loved being watched, especially by her friend who did care for her.

She slowly started to put her clothes on, still having the slight glow of sharing such an intimate moment. Not knowing what she was walking into, she left the bedroom heading towards the living room. The thirty dollars was on her side of the table as Jayden sat on the other side with a new bottle of wine and two glasses.

He poured himself a glass and offered her one. She sat on the couch and was taken aback by how nonchalantly Jayden continued conversing. He started talking about how one of his co-workers was trying to micromanage a project or something of the like. Claire reached for the glass and took a sip.

She knew what had just happened but was put off by the idea that Jayden brushed it off as nothing happened. They talked for what felt like hours when Claire realized she should get home.

As Jayden walked her to the door, he moved to hug her, which was admittedly awkward. However, he did whisper loud enough for her to hear, "Thank you for an amazing show. It is one that I will remember for a very long time."

When he said that, Claire immediately returned the hug and thanked him for a good evening.

Jayden walked out with her and both opened and closed the door for her. He stood there watching as she drove away. He walked back into his place and closed the door. It didn't take long for him to head to his bedroom and undress. He decided that he would clean in the morning. For now, he would lay in his bed and enjoy the memories of the evening.