Cindy\'s Night Out

Chapter 1

 

Cindy looked at her reflection in the mirror one more time before she went out.  She was wearing a low cut top that hugged her breasts and showed off a far bit of cleavage. Her skirt was short, so short that she would have to be careful how she sat. She had finished off her outfit with stockings and a pair of super high heel shoes.  It was not how she would normally dress; in fact, she had never worn anything like it before. She had gotten sick of sitting home alone every night and decided that she was going to do something to change that.  She had just begun her annual vacation, and was determined that she was going to use the four weeks to change her life. She picked up her bag and ran out to the honking cab so that she would not have a chance to change her mind.

 

Cindy saw the cab driver look at her and give a low whistle as she carefully got into the back seat. She could see herself in his mirror, almost not recognising herself with her extra makeup and died red hair.  “Where to love?” She realised the driver was talking to her and gave him the name of a club she had overheard some of the girls at work talking about. She had no idea what kind of club it was, but decided that for tonight at least, she would not be the kind of worrier she usually was. 

 

“Club Blue please, I think it is in the city.”  Cindy realised that she should have at least looked up an address, but she hoped the club was popular enough that the driver would know of it.  “Club Blue hey, I guess that explains the outfit, though I would have thought that leather would have been more appropriate.”

 

Cindy wanted to ask him why, but then remembered her decision not to worry about little things, so just smiled and turned to look out the window. The trip into the city only took about ten minutes and soon he was pulling up in front of the club. It looked like a typical club, with bouncers out the front and people in groups talking. She hoped that they would let her in, not knowing what kind of dress code they had. Paying the driver, she walked on slightly unsteady legs up to the entrance.  One of the bouncers asked for some ID and then asked if she was alone.  Cindy was a bit puzzled by this but said yes.  She was surprised to find one of the men taking her by the arm and leading her inside.

What she saw almost made her want to turn and run, but she couldn’t with him holding her arm. “Just wait here,” he had told her, and for some reason she did. She was standing at the entrance to the club and could see many people inside, but they were the kind of people she had only ever seen on the Internet.  Some girls were wearing almost nothing and some had collars around their necks.  She looked in one corner and saw a girl kneeling between the legs of a man dressed all in black, his hand resting on her head.  She was just about to see what would happen next, when she was startled by a man’s voice.

 

“Good evening, my name is Charles and I have been told that you are all on your own tonight. I am here alone too, so if you like, I can show you around the club. It can be a bit daunting the first time you visit, especially if you are alone.”  Cindy was mesmerised by the man talking to her, not only did he have the sexiest voice she had ever heard, he was very handsome too.  Like the other man, he was dressed all in black, with what looked like leather pants and a soft silk shirt.  His hair was also dark and he had soft brown eyes that seemed to gleam at her.  He wore no jewellery apart from a ring on one finger.  She suddenly realised that she had been so busy looking at him that she had not answered him yet.

 

“My name is Cindy and yes, that would be very nice, thank you.”  She had tried to sound confident but thought she had sounded more like someone responding to an offer of a cup of tea or something. He had not seemed to mind however and held out an arm for her to take.

 

Charles had been intrigued when the bouncer had come and told him that there was a young woman wanting to enter the club.  He had told him that she was all alone and did not really look like she knew what kind of club it was.  Charles had come along tonight just to look around and see if there was anyone he might consider taking on as a sub or even just to find someone looking for a little fun.  He had had a regular sub that had liked to play on weekends, but she had recently been offered a fantastic job in another city, which she had of course taken.  He missed her, but was also excited about the prospect of being with someone new.  He liked finding out what a sub liked and didn’t like, and with his previous sub he had been starting to find that they knew each other too well.

 

When he saw the girl, he was a bit surprised, as she did not look the usual type you would find in Club Blue. He thought that she had a pretty face, which for some reason she had hidden under a thick layer of makeup.  He liked her body under her clothes, though he would like to teach her the difference between sexy and slutty if he had the chance.  He could see her attention was taken with something in the corner and looked to see a woman servicing a man.  He saw the flush on the girl’s face and again thought how out of place she seemed, however he didn’t want her trying to navigate the club on her own.  When he had spoken, he had recognised that look that most woman got around him.  She had taken his arm and allowed him to lead her into the club.

 

“Cindy, can I get you a drink, perhaps a wine?” He could see her staring around the room, definitely seeing things she had never seen before.  He caught the eye of one of the drink waitresses, Cindy wide eyed at her clothing or rather lack of it.  All of the waitresses simply wore a collar with matching ankle and wrist cuffs and a small black g-string.  He saw Cindy look the girl up and down before turning away when the girl looked at her and smiled.

 

“Cindy, do you know what you want to drink or can I just get you a white wine?”
When she still did not answer he ordered her a wine and a scotch for himself.  He told the waitress they would be over on the couch and lead a still staring Cindy over to sit down.

 

Cindy sat down on the couch, trying to take in all she could see around her. She saw a waitress walk up with two drinks and suddenly she had a glass of wine in her hand.  Without thinking she almost drained the glass in one hit, needing something to calm her nerves.  She heard Charles order another glass before the waitress left and she put her glass down on a table, embarrassed at her behaviour. She turned to look at Charles for the first time since she had entered the club and saw that he had a grin on his face.

 

“I think you are lucky that I was here tonight, or you might have not make it out in one piece.”  Cindy just smiled but her former self started to emerge and worry about what he meant.  “Tell me, how did you know about this place. No offence, but you don’t really seem the type.” “Some friends told me about it, and as they were unable to come tonight, I though I would check it out myself.” She hoped that he would leave it at that, but he seemed intrigued by her choice of clubs.  “What did they tell you, these friends of yours?”

 

“Well, not too much, just that it was a cool place and really interesting. Tell me, Charles, what do you do?” She knew she was changing the subject, but hoped he would let her for now.  “I run my own company, we help small businesses set up websites.  What about you, what do you do?”  This was a question she had thought she would be asked and not wanting to say she was a boring office worker, she had decided on a more interesting career. “Oh, I work in the movie industry. I help to cast actors and find locations, that kind of thing, though I am on a break at the moment.”

 

Charles thought there was something not quite genuine about her answer, but again he let it go. They talked for a few more minutes, before the music stopped and the curtains opened indicating that the show was about to start. Charles was interested in seeing Cindy’s reactions, as he knew tonight’s performance was meant to be quite extreme.

 

Cindy saw the curtains open to reveal a big stage, with something that looked like an old fashioned set of stocks sitting in the middle.  A man wearing nothing but a very tight pair of leather pants appeared on the stage pulling something behind him.  Cindy was shocked to see it was a woman, her hands tied to the rope he held.  Cindy could see she was naked and that she had something attached to her breasts. She was vaguely aware of Charles moving closer to her, his hand coming to rest on her knee.  Her inner voice was telling her to brush his hand away, but her mind was too taken with what was happening on the stage to listen to herself. 

 

Charles could see that Cindy was completely captivated by the show, and decided that this was an opportunity too good to miss.  He moved his hand onto her leg and noticed that despite a brief glance down, she was ignoring him.  He moved his hand up her leg and then down to her inner thigh, feeling the soft skin above her stocking tops. He could feel her breathing becoming short, though whether it was from him or what she was watching, he wasn’t sure, nor did he really care. He allowed his other hand to reach around her and sit on her breast for a moment, before slipping it into her bra when she did not move away. 

 

He started to rub her nipple inside her bra and was not surprised to feel the nipple grow under his fingers.  His other hand was still stroking her inner leg and he even thought she had moved her leg a bit to let him get better access.  He moved even closer to her, expecting that at any moment she would push his hands away or worse still, run away from him.  He was aware of a few people around him looking at what he was doing but for the most part, all eyes were on the stage.

 

Cindy could feel Charles’ hands on her, but still she did nothing but stare at the scene in front of her.  The man had forced the woman onto her knees and had secured her into the stocks, her body side on to the audience.  She had been able to see that she had some kind of clip on each breast and had tried to imagine what she must be feeling.  When the man had knelt down and placed what looked to be big ball bearings onto the clips, Cindy had not been surprised to hear the woman moan in what had to be pain.  All the while, she could feel a growing sensation in her pussy, as Charles continued to gently manipulate her body.  She felt him move his hand that had been stroking her leg and start to rub her pussy lips through her panties. The feeling made her gasp, as his fingers sent small shock waves through her body. 

 

She was about to say something when the man on stage picked up what looked like a whip and hit her with it.  The woman screamed, her body jerking in the stocks.  The man dropped the whip and picked up what to Cindy looked like a red table tennis ball with some straps attached.  He again knelt before the woman and lifted her head by gripping her hair in his hand. As her mouth opened, he pushed the ball in, letting her head drop as he tightened the straps.  He then used her hair to raise her head again, looking to be checking the fit of the ball in her mouth.  He dropped her head down once again and moved to pick up the whip, proceeding to whip her all along her back, bottom and upper legs.  With her mouth now blocked, the woman’s screams were muffled.  Cindy wondered if she should just run out of the club while she had the chance, not wanting anything like that to happen to her, but she felt like something was holding her to the seat.

 

Charles knew that Cindy was not really aware of what he was doing, but he could feel that her body was.  He had moved his fingers to rub her pussy through her panties, not surprised by how wet they were. He heard her soft gasps as he rubbed her, knowing that this time it was definitely him she was responding to. Her body tensed as the scene on the stage intensified and he prepared to grab her if she decided to run off.  It was not that he wanted to keep her here against her will, but he did not think it would be a good idea for her to be alone in the club and especially not the surrounding neighbourhood. He decided to give her something else to think about and moved her panties aside to allow his fingers to enter her pussy. 

 

This time her gasps were louder and he felt her body relax a bit under his fingers. He gently rubbed her, feeling her moisture on his fingers. Working his way further into her, he suddenly stopped, feeling her resistance.  He wondered that she could still be a virgin but he had the proof right there, at his fingertips.  He withdrew his fingers slightly, not wanting to hurt her, and moved up to rub her clit. 

 

Cindy had felt Charles’ fingers move to enter her pussy and felt a warm, tingling sensation spread through her whole body.  Her breasts felt heavy and the hand on her breast felt like it was part of her.  She was aware of him moving deeper into her and then stopping. She had thought for a moment that her virginity had tuned him off, but when she felt him rub her clit, she forgot all thought.  Cindy even lost focus on what was happening on the stage as she felt her orgasm approaching.  Though she had not had much experience with men, she had become fairly good at bringing herself to orgasm.  She had to admit, though, that she had never felt anything as intense as she was feeling now.  She was about to cum when he abruptly removed both of his hands and stood her up.

 

Charles could tell that she was close to cumming and didn’t want her first orgasm with him to be so public.  He knew the club kept rooms for members to use, and as he could see that most people were intent on watching the show, that there would be no trouble finding an available room.  He could tell that Cindy was confused by his actions and moved her quickly to the area of the club where the rooms were.  He used his member’s card to enter a room, and sat her down on the couch inside.

 

Cindy did not know why he had stopped what he had been doing or why they were now in another part of the club. He had sat her down on the couch, but when he had turned to shut the door, she had panicked and moved to the wall at the back of the room.  What had she been thinking, letting him touch her the way he had been before? What did he want now?  For all she knew, he wanted to do the same thing to her that was still being done to the woman on the stage. When he turned around to look at her, she could see his surprise that she wasn’t on the couch.  Expecting him to come for her, she moved back further into the wall.  When he simply moved to the small fridge and pulled out a bottle of wine and two glasses, she still did not move. She watched as he poured out the drinks, placed the glasses on the low table near the couch and moved to sit down. 

 

Charles could have kicked himself, he had succeeded in doing the last thing he had wanted to do and that was to scare her. It would serve him right if she demanded to leave right away. When he had turned to see her not on the couch, but standing looking like a frightened child, his first instinct was to hold her in his arms, but he knew that would only serve to frighten her more. So, he had tried to act as if everything was normal and poured them both a drink. Now that he was seated and sipping the wine, he could see her start to relax and even find enough nerve to come and take the other glass.

 

He knew that he had to take it slow and decided to let her make the first move. As time went by and she said nothing, just sipped her wine and looked at him over her glass, he knew that he would have to be the one to break the silence. He tried to think of what he could say that would not scare her even more and hopefully keep her with him for a bit longer.

 

Cindy sipped her wine, still not sure what was going on, but starting to calm down a bit as Charles made no move to approach her.  She still was not sure if she was comfortable being in a room alone with him, but she felt that she was in no immediate danger. She sat down on a chair opposite the couch and continued to sip her wine.

“Cindy, I am sorry if I scared you, believe me that was not my intention. I had only thought to take you somewhere more private as I was sure you didn’t want everyone to see you cum.” At the mention of her near orgasm, not only did she feel herself blushing but became aware of her pussy throbbing.

 

“I can see by your blush that you remember what happened out there. If you like, we can take up where we left off, or I can arrange to take you home.”  Cindy considered his options, the old, sensible Cindy screaming at her to go and go now, but she had never felt like she had before and knew that she would regret it if she didn’t stay for at least a little bit longer. After all, she had left home determined to make a change in her love life.  The throbbing in her pussy also helped to make up her mind to stay, her body crying out for more.  “Charles, if you are willing to spend more time with me, then I wish to stay and… and well…finish what you started.” Cindy was not used to talking about sex, especially in connection to herself. She saw Charles smile and ask her to stand up.

 

“Cindy, I need you to trust me and do what I say, do you think you could do that? I promise that no harm will come to you.”  Charles knew that he was taking a risk in asking her to trust him so soon, but he could see that he needed to take control as Cindy obviously had little experience. He actually liked the fact that she was so innocent, his mind running over all the things he could teach her. He was pleased to see her nod, her eyes showing some feint remnants of her earlier fear, but nothing more than he would expect to see in a situation like this.

 

‘Good girl, now I need you to stand and remove you shirt and skirt.” Charles waited while she took another drink before standing and starting to remove her shirt.  He could see she was embarrassed but this did not stop her. When she had her skirt off, he asked her to come and stand in front on him.

 

Cindy moved to stand in front of Charles, trying to cover herself as she stood close to him. She had bought new underwear and thought the see-through material sexy in the store, but now she wished she had her old sensible ones on again.   She could feel his breath on her stomach as he moved forward to examine her.  He gently took her hands and moved them to her side, tracing the line at the top of her panties.  She gasped, feeling a shock go through at this slight touch.

 

“Cindy, you are so beautiful. Now I want you to sit on the couch, with your legs spread and your bottom at the edge.” Cindy saw him stand up and she moved to take his place, sitting just as he told her to. She felt the cool air on her panties and knew that they must be soaking.  “Good, now remove your bra and place your hands on your breasts.”  Cindy followed his instructions, again feeling her face flush.  She felt him lift up her feet and remove her panties and then her stockings one by one. She tried not to think of the view she was giving him and just let her body relax. It felt strange that she was letting a man she had only just met touch her, but it just felt so right.  Cindy shivered as he ran his hands up and down her legs and closed her eyes to make the feelings even more intense.

 

Charles saw her body revealed and marvelled at how beautiful she was. He told her to start to squeeze her breasts, while he lowed his mouth to taste her pussy. He saw that she was not a natural red head, her pubic hair a mousy brown colour.  Using the back of his hands, he gently moved her knees out wider and used his tongue to burrow between her pussy lips. The sound of her moans reached his ears and he knew he had hit the right spot.

 

He sucked and used his tongue alternately until he sensed her orgasm was close.  Charles lifted his head to see her eyes half shut and her head moving side to side. “Cindy, Cindy! I want you to pinch you nipples.  That is right.”  He saw her pinch her nipples, making them stand up even more than they had been.  Charles lowered his head and found her clit, sucking it into his mouth.

 

Cindy felt the jolts through her body as first she pinched her nipples and then as he sucked her clit into his mouth. She could feel her orgasm building up to one even bigger than before. Suddenly, her world exploded, her body jerking uncontrollably at the most incredible orgasm she had ever experienced.  “Well, that was a beautiful sight.  Now, there is a shower here if you would like to freshen up before you decide what you want to do next.” 

 

Cindy was aware of him talking to her, saying something about having a shower, but her mind was still trying to come to terms with what had just happened to her body.  She felt him help her to her feet and lead her into a small bathroom. He turned on the shower and returned to the main room.  Cindy stepped into the shower, loving the feeling of the water on her skin. Without thinking, she let the water run over her head. Too late, she remembered her fancy hairdo and makeup. Knowing it was too late to save either, she relaxed and let her body enjoy the sensation of the warm water. She allowed her mind to relive the feeling of his mouth on her and that wonderful orgasm.  Cindy thought she could hear the sound of Charles talking, but was enjoying the shower too much to worry.  Turning off the shower, she dried herself with the softest towel she had ever felt. It was not until she looked at her reflection in the mirror, did she see how the water had ruined her makeup.  She had just begun to wipe away the worst of her running mascara, when she heard Charles voice behind her.

 

“Well, I am sure that feels much better and don’t worry too much about your makeup, the club keeps everything you might need in the drawers.  However, please don’t use so much this time, I would rather see your pretty face than a pile of makeup. When you are ready, I have taken the liberty of getting you some new clothes that suit the club better. Of course, you may wear your old clothes if you wish,”

 

At that, he left, not giving her time to respond. When she turned to see the dress he had hung on the door, she thought she had never seen anything so beautiful. It was dark blue and made out of the lightest of materials. She knew it would sit perfectly. Eager to try it on, she quickly redid her makeup, being careful not to use too much, but still more than she was used to.  She saw a hair drier on the wall and dried her hair, letting it fall naturally around her shoulders.  Once she was satisfied that she no longer looked like a drowned rat, she turned to put on her underwear, suddenly releasing that they were nowhere to be seen. She was just about to ask Charles where they were, when she spotted a bag hanging with the dress. On closer inspection, she could see that he had also provided her with new, very expensive looking underwear. 

 

She put on the bra and panty set, noting that though they were very light, they fit her perfectly.  She saw he had also provided her with new, silk stockings, and loved how they felt on her legs. When she pulled the dress over her head, she couldn’t help but stare at the image she saw in the mirror.  The dress exposed just as much skin as her previous outfit, but instead of making her look like a hooker, this dress made her look like a model. It skimmed her body while still showing off her breasts and hips in a feminine way. 

 

Charles stood in the doorway, watching Cindy looking at her reflection in the mirror.  He was amazed at the change in her, her hair and makeup looking much more natural and the dress was as prefect as he thought it would be.  “Cindy, you look stunning! I just knew that dress would suit you. Here are the shoes to match. Now, come and sit down, so we can decide how to best spend the rest of the night.”  He saw her sit, a curious look on her face.

 

“I know you are wondering about the clothes. The club provides many extra services for long-term members, including access to a range of clothes.  Now, this will finish off the outfit rather nicely.”  He held out what looked like a velvet choker with a sparkling blue gem in the middle.  He moved to fasten it onto her neck, stepping back with a satisfied look on his face.  Cindy could feel the choker on her neck and was reminded of the collars she had seen many of the women in the club wearing.  She was about to comment on this, when Charles started to speak again.

 

“Cindy, I have enjoyed my time with you so far, as I hope you have too.  I would like it if you would consider coming home with me tonight.  Of course, we can just spend some more time in the club and I’ll make sure you get back to your home safely. You don’t need to answer now, but just know that it would make be very happy if you were to agree.”  He could see her mind going over the possibilities and was glad that at least she wasn’t saying no right away. 

 

“Charles, I am not sure what to say, you have been so kind to me. The clothes, your company and, well, you know.  I will certainly think about your offer.”  She saw him smile and was pleased that he was not doing anything to pressure her. “Charles, this chocker, it reminds me of what many of the women in the club are wearing.  Does this mean the same thing?”

 

“No love, your choker is for show but for many of the woman in the club it means that they are slaves.  The collar showed that they have a master or mistress.”  Charles saw her go pale, and realised he may have given her too much information.

 

“Slaves, what do you mean they are slaves?”  Cindy felt herself go weak at the thought of people owning other people, and remembered all that she had seen before she had been brought into the room.  “Love, I have scared you again, I just keep forgetting that all this is new to you.  What if I arrange for you to talk to one of the women in the club, so you can see that it is not as bad as you are obviously imagining it to be?  Remember, we can leave or I can send you home whenever you want to.”

 

Cindy looked at Charles, the honesty she could see in his eyes convincing her that she should at least stay for a while. “Ok, I will stay for a while.”