Holly's Croupier Strip

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Holly gets another chance to remove her clothes for a crowd
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If you read my first entry "Holly's First striptease" it will give you an idea how I try to work stripping into different situations.

The last time my lady friend Holly took her clothes off in public was as part of a private function evening at a local social club. Although it had been planned between her and my mate Rob, who was the compare for the evening, it was played out as though she was doing it on the spur of the moment as a sort of fill in for a stripper who hadn't turned up for the party. She always wanted to do it and everyone had a great time including me because we satisfied our sexual urges after her performance with a shag in her dressing room.

The next time she took her clothes off would be a little different. She was still a willing participant but the guys who were watching would be under the impression she was doing reluctantly.

Holly was working as a secretary for a decorating firm when she "performed" last time, which was around 6 weeks back. It was coincidental because the whole premise of her undressing was based on her being a secretary at the club who was persuaded to strip for a group of company employees (not her company). She was out of work at the time of the next adventure so the money would come in handy with the added bonus and excitement of removing her clothes in front of a lot of horny guys again.

The story started while I was having a friendly drink one night in the local pub with my mate Rob, the comedian/compare. Rob mentioned to me that he was still trying to get Holly to do professionally paid striptease on a regular basis but she always seemed reluctant, only preferring to do it under special arrangements like before under the assumption that it was unplanned. He mentioned that he had been asked to do an evening job as part of a casino night which took place after a sales meeting for a group of betting shop employees, around 20 of them. At the end of a day's meeting they would have a meal in the hotel then go to a specially set up room which had a roulette table, black jack table and a crap table. It would be loosely based on Las Vegas casino as they were all in the gambling trade.

Rob had suggested to the director of the company that Holly would be there, but in a capacity as a croupier, not an "entertainer". She'd be getting paid by the company but maybe a few extra gratuities would come her way as well. Rob would tell a few jokes before they started to play the tables, then one guy, who had been primed of what was to come, would suggest making a few special bets which involved Holly. The fun thing about it would be that only this individual would know about the bets, not even Holly or Rob. She knew she would eventually be getting her kit off but wouldn't know how it would be worked into the evening. After Rob had done his comedy spot Holly would arrive and work as the croupier on the black jack table, Rob the roulette and I'd do the dice. She once worked in a casino so she had some experience of black jack which meant she would look like she knew what she was doing. At some point in the evening the guy, Greg was his name, would suggest a different kind of betting game in which Holly would be the main participant.

The Gambling Evening The meeting was held on a Friday so no one had to worry about getting up early for work the next day. They could all leave for their respective homes after breakfast the next morning. The meeting finished around 6 o'clock and the guys went back to their hotel rooms, showered, changed and had their meal in the hotel restaurant. At around 8.30 Rob entered the restaurant and introduced himself to the group. He made small talk for minutes before asking them to join him in a back room where the gambling tables were set up. They came into the room which was quite plush, nice thick carpets, a bar, TV screen, roulette table, black jack table and for some reason a flip chart. I was there with Holly and Rob introduced us and explained to everyone that I was there as the manager of the agency who had supplied Rob and Holly for the evening. This was a lie of course but I had to wangle my way in some way to be able to see Holly disrobe later. Holly was dressed smartly but sexily in what I suppose could pass for a croupiers uniform in the fact that she wore one of those tight waistcoats that are considered to be part of the ensemble. Not exactly what you'd see in a Vegas casino, or even Blackpool for that matter, but it was certainly not obvious that she had dressed with the intention of taking off her clothes for our entertainment. Under the waistcoat she was wearing a long sleeved pink satin blouse which was buttoned to the top. Her black skirt was a tight fit and my guess was it was also satin, although I'm not expert, but it certainly had that look. Her gorgeous legs were covered in a glossy hose which was dark, possibly barely black and maybe a 10 denier appearance. Her ensemble was completed by a pair of high shiny black stilettos. No one in the room would guess that she had purposely come here tonight with the intention of performing a striptease for the lucky gents. Holly and I were busy setting up the gaming tables while the guys all sat down at the various lounge tables that were set around the room. I saw a few of them cast appreciative glances towards Holly but no more than that. When everyone was seated and supplied with drink Rob launched into his comedy spot. After around 20 minutes of jokes, a few risqué ones and several anecdotes he declared it was time to, as he put it, get down to some serious gambling. He basically let everyone choose which particular game they wanted to play and it was around an even split between the three games. At this stage in the evenings proceedings only Greg knew the plan for getting Holly out of her croupiers outfit, not even Holly. So it was going to be surprise to all of us. Of course, all the other guys were totally unaware of how we would be finishing the evening off so it would be an extra special treat for them. All three games started with small amounts of betting in chip form. This carried on for a while until a few guys who had been luckier than others decided to up the ante a bit and started to increase the stakes. Holly was working professionally throughout and giving no hint of what she may be doing later. Obviously some of the guys flirted a little with her although there were a few mildly suggestive comments during the black jack games, nothing more than you'd hear in a pub bar on a Saturday night and no one went too far. After about an hour Holly said she would stand down at the table for a short while to take a breather and the games on the other two tables carried on. She left the room to pop to the ladies and when she returned she took a complimentary glass of wine from behind the bar and sat down in one of the armchairs at the side of the room. By the time she had finished her wine it was about 25 minutes since she'd closed the black jack game. She announced that she would be starting up again if there were any guys who wished to try their luck again. She was also getting a little curious as to when she was going to get the opportunity to offer the more exciting services she was looking forward to delivering. It had been well over an hour and a half since everyone had been playing the gambling tables and she thought it was rather a long time to be waiting to get down to the real entertainment. She was still unsure in what situation she would be persuaded to undress for these gentlemen. She didn't have long to wait. Holly's announcement that the black jack table would be opening again was the opportunity Greg had been waiting for. Greg stepped away from the roulette table where he had been winning on a regular basis and stood in the middle of the room holding up a couple of handfuls of betting chips. "Ok lads" he said. "I don't know about you but I've had my fill of roulette for this evening, I have won a fair bit of cash tonight but I'm prepared to offer all my winnings up to gamble on some more interesting wagers" Most of the guys looked intrigued but slightly puzzled. He gestured towards Holly. "What if we ask our lovely hostess here a few questions about herself we could have a few little wagers on what she answers" Holly knew this was the cue for what was to come. She looked at Greg in a way that indicated she was unsure what he meant and then gave an expression of puzzlement. There was a general approval that hummed around the room and several guys nodded their approval, even though they weren't 100% sure what Greg had in mind. I got the impression they were quite prepared to go along with it as it involved the lovely lady who had been dealing the cards to them for the last hour or so.

"OK, that's settled then" said Greg.

"Excuse me". Holly piped up. "Do I have a say in this?. What sort of questions are you intending to ask?"

"Let me see" said Greg. "I've got a little list somewhere for just that I've been working on just in case things got a bit dull this evening".

He fumbled in his trouser pocket. "Ah, here it is". He scanned it for a few moments and smiled a cheeky grin. "Do I get to see it?" said Holly. "Wouldn't that spoil the fun?" said Greg. "Just be sure, that they are questions only you know the answers to, and all the guys here will be more than pleased to find out". Rob then butted in to the conversation. He obviously knew where this was leading much to his delight, but of course he had to be seen to be on Holly's side as he was the so called organiser of the party. "Come on lads, is this really fair to Holly. She's been working hard all night and now you want her to get involved with something that seems a little dubious if you don't mind me saying?" "Well, I understand you sticking up for her mate, but there are only a few simple questions. What harm can it do?" Said Greg. "I'm a bit uneasy why you won't let anyone see the questions" said Rob. "Wouldn't it be polite to let the lady decide for herself?" said Greg. He looked at Holly as if for confirmation. "I suppose it would be OK as long as the questions aren't too personal" said Holly. "What about I ask one then my dear, and see how we go from there?" Greg suggested. "OK then. One question and then I can see if I want to go on" said Holly. "What do I do now?" "Well, I'll stand ready at the flip chart and ask a question. Then the guys shout out what they think you'll answer, I write their suggestions on the chart and they put their money where their mouths are by betting on what you'll say, the winner of the kitty is the one who guess's right". Greg explained. "If the guys want to gather round in a semi circle, sit down where they can, you can stand in front of them". Greg moved and stood by the board, pen in hand. The guys all positioned themselves to Greg's left, some in chairs, some standing, and Holly stood in front of them so Greg was to her left, at an angle. "OK" said Greg, "If we are all ready, here is the first question". He held up the small note in front of his face. "This one is not normally something you should ask a lady, but here goes". I was sure most of the questions would be of the same nature. Greg continued "Holly, if you would be so kind and not too embarrassed, I would like the gentlemen to guess your age". Holly looked mildly shocked but half expecting something a bit more intrusive. "Well, it's a taboo subject for most ladies but I don't mind this time" She said.

She knew this was the beginning of the time during the evening which would eventually lead to her being asked to remove various items of her outfit but the first question didn't suggest what was to come. "Before you answer my dear, I need the guys to give me their guesses". Greg pointed out. Greg scribbled out the question on the flip chart then waited pen in hand for the predictions. "OK, let's hear what you think guys" Greg said. "But before you do, Holly could you please take £5 from every man. The closest to your age wins the lot". The group of men then proceeded to tell him their estimates at the lovely lady's age. Greg wrote them down. The estimates ranged from 23 to 30 with most in between. 27 seemed to the most popular as 6 of the guys guessed it. Greg surveyed the answers on the pad. "Well we have quite a few different guesses don't we, I wonder who is going to win the dosh?" He looked at Holly questioningly. "Holly, would you like to tell the gentlemen who wins the money?" Holly put her hand on her chin in a thoughtful pose. "Not one of you has the right answer gentlemen, but I thank you from the bottom of my heart for all of you thinking I was as young as you've said, but I'm actually 36". She told them. A chorus of disbelief went round the room. Slightly mocking comments such as "I never would have guessed" and "you look fantastic for 36". "As no-one actually guessed Holly's age correctly I think we should do a roll over" Said Greg. "Holly, are you up for another question if the guys add to the pot?" "Well, I'm not sure" said Holly. "The first question was pretty personal, although you did all guess much lower than my actual age which was very sweet of you. How can I be sure that the next question is appropriate too?" "I suppose you'll just have to let us know what you think of it when I ask it?" said Greg. "I suppose you're right" said Holly. "OK, then" said Greg, "I was going to ask you your vital statistics, and like most men, what is of most interest is the first measurement. I was going to ask in a slightly different way but first I need to confirm if you are wearing a bra?" "This is getting a bit naughty" said Holly, "But I don't see any harm really. As you'd no doubt expect I was anyway. You can probably tell from the way my blouse looks. So the answer to your question is yes, I am wearing a bra". "That's good" said Greg. "OK, for the next bet I'd like the guys to guess the exact measurement and cup size". "Getting very cheeky aren't you?" said Holly. "You think I'm going to give you the answer then do you?" "Well, if all these guys are gonna stake up some money, they'll need to know" said Greg. "I tell you what, let's see how much cash we get for the guesses and the guys can donate part of the pot to you to do with what you wish. You know a deserving charity or buy yourself a new dress or handbag"? "That sounds like a more attractive offer" said Holly. "As long as I have the final say when the money's collected". "OK" said Greg. "That sounds fair. OK guys; let's see the colour of your money". With that the men in the room dug into their wallets again and handed over their contributions to the pot to Greg. In total there was £150. "£150 my dear" Greg informed Holly. "If we say £75 to you and the rest to the winner, how does that sound?" "I think I would be prepared to divulge the size of my bra for £75 gentlemen" said Holly.

Greg then asked the guys for their guesses and wrote them down on the flip chart while Holly looked on with some amusement at what these men estimated to be basically the size of her tits! "Well Holly, we have a few differences in the cup size but only 3 for the actual measurement" announced Greg. "Would you be as kind as to tell us who is closest?" Holly stood in front of the chart and bent forward to study the list a little more closely. As she did the audience had a rather nice view of her tight skirt clinging to perfectly rounded derriere. Like me I'm sure most of the guys watching were wondering what delights lay beneath the tight black garment. Holly pointed to a number on the chart and announced that one particular chap had guessed both dimensions correctly. "This one is the winner, its Mike" She said. "My measurements are 36D". Mike stood up and Greg gave him his winnings from which Mike happily handed over £75 to the lovely Holly. A muffled round of applause was given to Mike. He sat down again and Greg turned to Holly who was still standing by the chart. "Well now Holly, that wasn't too embarrassing, was it"? Greg asked her. "You've made a nice little sum there". "I suppose not" said Holly. "How would you like to make a whole lot more?" he asked "It depends on what I have to do" she answered. "Just keep on answering questions really" Greg explained. "What sort of questions?" she replied. "Well... questions of a more personal nature" said Greg. "How much more personal can you get? You've asked a lady her age and now her boob size" said Holly. "I can think of a few more that would interest the guys" said Greg with a cheeky grin.

"How about some questions about your outfit?"

"What's wrong with my outfit?" Holly said questioningly. "Nothing at all my dear" said Greg. "It's just we'd like to know more about it".

"How much do you want to know?" "You can see what I'm wearing" Holly said.

"Forgive me if I'm wrong my dear, but we can't see everything you're wearing" Said Greg.

Holly looked slightly embarrassed and shocked.

"Whatever are you suggesting? She asked Greg.

"I'm suggesting, if you are willing to participate for even greater sums of cash, that my colleagues may like to place a few more slightly daring wagers" he said.

"Not sure if I like the way this is going, how daring do you mean?" asked the lovely Holly.

"Well, why don't I suggest another bet and you see if you are prepared to go along with it?" said Greg. "And if I don't?" she replied.

"Then we all carry on playing black jack or roulette and have a lot less fun" said Greg.

Holly though for a moment about the possibility of revealing, at least verbally, aspects of her outfit and then though about making what could be a tidy sum of money on the side.

"OK, I'll give it a go, but only if the money's right and in an effort to make the evening more enjoyable" she said.

"That's the best news I've heard all week" said Greg. "I'm sure this party will get a lot more interesting. OK let's see where we can go from here". He took a step back from Holly and looked her up and down.

"I've heard a few of the guys making some very complimentary comments about your lovely legs. I've seen them point to them and whisper things to each other. I wonder what they're whispering about?" he said to Holly.

"I'm sure I wouldn't have a clue" said Holly with a wry smile on her face.

"I think I can guess" said Greg. "They must be commenting on the exquisite shimmer that your hosiery is making, do you agree?" "Well I suppose they might be" said Holly "They do have this sort hi-gloss appearance. I prefer this type and they look really pretty" "I think they'd like to know more, don't you?" he asked. "Like what?" said Holly

"Well I'm sure we'd all like to know what's causing the lovely glossy appearance. In other words are you a lady that prefers to go for the practicality of tights or... the easiness of hold ups. Or, fingers crossed, stockings and suspenders?"

"You weren't kidding when you said more personal questions were you?" said Holly. "Do you really expect me to tell you what I have on under my skirt?"

"If you want to tell us what you have on then I don't think anyone here will object" said Greg. "I thought we were only actually talking about a bit of nylon aren't we, or were you offering more?" he said with a cheeky grin.

"No I only meant my...my..." she hesitated, trying to be a little careful not to divulge too much about the nature of her sexy leg adornment. "My hosiery, nothing else" She deliberately put on a flustered look but secretly enjoying the sexy conversation.

"Well if we can persuade you to tell us about all things nylon, then maybe there are other things we'd like to bet on" said Greg. "Isn't it worth it for a few quid? All you'll have to do is say which you prefer, no one will know if you're telling the truth"

"But that's it isn't it?" she replied, "No one will know, I could say anything"

"You wouldn't you really tease us like that. I'm sure you'd tell the truth wouldn't you?" said Greg. "Just let the guys have their guesses and see where we go from there, yes?" he asked Holly. "OK, I suppose so" she replied.