While Sissy talked to the group, Liz kept busy getting things ready for the bikini contest and more, and Sissy watched the group as new conversations began and smiles were abundant. "Excellent," Sissy said and then added, "Okay ladies, when you're ready, join us up here." As the women moved, Liz went to the back of the tables and worked her way forward passing out little score cards and pens with the resort name on them to the men.
Sissy had the five women lined up shoulder to shoulder and Liz stepped behind them and whispered loud enough to be heard that she was just going to attach number tags to the back of their bikinis. To do that, Liz slipped two fingers inside of the little waistband in back and the first woman twitched and said, "Oh."
"Sorry, these need to be fastened low and my fingers are probably a little cold. With that done to each of the women, Liz moved back to the side as Sissy said, "Okay men, from left to right, the ladies are one through five, and as you can see on your cards, you pick the most daring bikini first. If it's a tie, then give both numbers. Then below that, give your pick for overall sexiness, and guys, your name isn't on the paper so don't feel compelled to choose your wife for everything. Be adventurous. You can always lie to your wife and say you voted for her right?"
The room was almost quiet as the women watched their men and smiled, and three of them struck poses and held them, while the other two stood straight and rigid. "Okay now for your third vote, put down the number of the woman you'd most like to make love to other than your wife. That time the men looked at Sissy and Liz and smiled. They were very willing to get into that moment of fantasy. Liz collected the cards and put them in a neat stack on the little table next to her. "We'll come back to the results of that shortly, because we have another game to play. Ladies you can go back to your seats." Sissy reached behind the curtain and pulled the corkboard out with eight envelopes pinned up in two neat rows.
Then still nervous Liz took over and said, "Each of these numbered envelopes lists a prize to be won. Most are somewhere between silly and nice, and two of them are very nice prizes, and the best part is every couple will win a prize. Here's all you have to do to claim your prize. This couple closest to us, stand up for us. Now sir, your lady has a number on her bikini. All you have to do is find that number, retrieve it and match it to an envelope. Any time you're ready, find the number while we watch and wait." The woman was half blushing just from him staring at her chest before he turned her around and studied the back. He looked at Liz and Sissy and shrugged his shoulders in defeat until Sissy told him, "Oh it's there. Now no cheating miss, make him figure it out. Is it inside of her bra maybe?" The woman turned her head to look at Sissy in surprise as he turned her back around and stared at her breasts again He timidly pulled at the small piece of fabric and looked at her breast but found no number. Then he looked at the other side and again, no number just as Sissy said, "Miss tell him where it is."
"It's in the back Mark." He looked back there and then took a breath and pulled her waistband back and found the number, but it was down far enough that she was going to feel his hand on her naked ass.
"Oh get the number Mark, nothing is going to bite you," and the nervous and focused group laughed. He reached in and came out holding the number like he'd just caught a prize fish. "Great, show me the number lover." He held it up for her and she passed him the envelope. Tell us what you won for your valiant efforts Mark."
"A souvenir tee shirt."
"Oh, that's too bad. But that improves the odds of the next couple. You two, what's your first name sir?"
"Ken."
"Okay Ken, go for the number and we'll wait." Thinking the number wouldn't be in the same place that Mark had found his, he went for her bra and all but exposed her breasts to the group, but found no number. He licked his lips and looked at her so she told him, "Mine is in the back too Ken." He was less delicate so he hand his hand all over her round and slightly large ass until he found the number tag and pulled it out and held up number nine. Liz handed him the envelope and Ken read, "For the lady, a hundred dollar gift card to Victoria's Secret," and the rest of them applauded.
It went faster for the other three couples because now they knew where the number would be found, but the men still ended up feeling their woman's exposed ass and that's what it was really all about anyway. The temporary couples were leaning over their tables and whispering back and forth until Sissy held the cards from the bikini contest. Where is number five?" She stood up and Liz passed an envelope back to her saying, "You won the most daring bikini, and we can all see why. Very hot."
The woman opened her envelope and said, "Oh, how nice." Then she looked up and said, "I won a full massage and facial with Len, the masseur, here on the island and he comes to my cottage."
They applauded, and then as they settled down, the prize was given for the sexiest woman, but the one that was generating the most interest was who would win the one most voted the most desirable. "Number two, stand up and tell us your first name.
Sissy and Liz were a little surprised when the woman stood up. She wasn't the sexiest or the prettiest. Good shape yes, but not the best of the five. "I'm Janet."
"Congratulations Janet, your five male friends voted for you four out of five for being the most desirable." Janet smiled and with furtive glances at some of her friends, she quickly sat down again as Liz got the envelope to her. Janet opened it and put her hand to her mouth in surprise. "Oh wow!" Then she looked up and said, "I don't know if I can do that."
"Just promise us you'll try your very best for your friends. Tell us what you won."
"A three hundred dollar certificate at Victoria's Secret, but I have to model everything I buy for everybody here." All of the men stood up and applauded and cheered for her, and the women clapped enthusiastically.
"I know," Liz said smiling, "Maybe number nine, Ken's lady, will model her prizes with you to support you," and again the men stood up and applauded.
Liz added more envelopes to the corkboard and Sissy said, "Okay, this is the last test for tonight. How many of you ladies have gone topless up and down the beach?" Surprisingly only one hand went up so Sissy said, "Now that isn't good, Okay the plan is changed. We're looking for a brave woman to come up here and trade in her bra for a prize. That's right, we keep your bra, but you get the prize, to say nothing of the admiration of the men. Of course the one woman that had gone topless went up and forfeited her bra and chose her envelope. She held it up and said, "A souvenir tee shirt and shorts."
"Sorry, but I promise you there are nicer gifts to be given away. Who will join this brave and sexy woman." Another woman stood up and Sissy smiled and said, "Perfect our most daring bikini, come up here and claim a prize. The woman went up and facing her friends she removed her bra and handed it to Liz and chose her envelope and opened it.
"Oh very nice. A Waterman amethyst ball point pen, thank you," and she smiled at Liz and Sissy before she went back to her seat. Her table mate openly stared at her breasts and whispered, "Oh damn, I can hardly breathe," and she smiled as she basked in his effusive comment.
The remaining women were gaining courage as their friends exposed their breasts. A minute later the remaining three women went up, and though somewhat less than calmly, they surrendered their bras and got their envelopes, which didn't contain anything worth more than thirty dollars. Sissy quickly whispered to Liz and waited until Liz nodded and agreed with her. "Okay, we want to give all of you a choice. Rather than wait until Thursday, would it be better if we were to have part two of the entertainment tomorrow after lunch, keep it on Thursday or cancel it?" There was a rush of don't cancel it, and that was followed by having it after lunch on Tuesday. "Oh there is one thing you might want to know. We're going to up the games just a little, and guys, you can't escape the games. Tomorrow, the ladies get to have some of the fun." All five women rose to their feet and applauded. "Okay then be here at two tomorrow and we'll see what kind of trouble we can get into. Oh and ladies, be sure hubby...well or the man seated with you now, have them put sun lotion on your tender bits because the tropical sun could roast your nipples."
Liz and Sissy gathered their things, and leaving the corkboard behind they left and headed home. "Well, what do you think Sissy?"
"I think for a first time it was great. I can see where we need to rethink the timing a little and things like that, but I'm good with what we're doing. What about you?"
"I think they really enjoyed themselves, and I agree we waited to long to do this. Of course our next group might be a whole different story because if doesn't sound like they will be more than acquaintances."
"True."
"But they are having fun. We'll have to be careful with expensive gifts though unless we charge the guests more or build it into the cottage rates, but at least right now this is going to get the word out about us."
Mac was full of questions and hit the women before they could even close the door behind them, and for the next hour they talked and enjoyed wine. When he learned that Liz was topless he smiled and said, "Way to go honey."
She smiled and said, "Of course with Sissy's boobs right next to me I didn't have to worry about being stared at."
"You both dazzled them and you know it. I wish I could have been there to watch you two."
Liz kissed him and refilled their glasses, and then sitting down again she said, "Sissy and I learned a lot tonight. What works well and what we need to modify. Nothing we did was bad, but there's plenty of room for improvement. And it could get expensive so we need to talk about that at some point. Also, we'd like to have Didi with us tomorrow."
Sissy smiled and said, "You know, another pair of unfamiliar boobs and her cute smiling face as we torment the men."
"That's fine with me, so I'll leave all of that to you two to handle. Oh, and we're up to three couples for our next group, so if he can come up with two more, you'll have more entertainment to consider."
"I hope so, because we think they would be even more impressed with our little bit of naughtiness."
"I think you're right, and you'll have the anniversary celebration angle to work with."
Sissy smiled and said, "Oh ,and how that does trigger ideas."
"You may find comments after they are gone that will help you with your next show."
"We can only hope."
Chapter One Hundred Twenty Eight
Sissy, Liz and Didi spent the morning going over the plans, and they were at the dayroom by one. They were ready just before two including bottles of red wine and two glasses on each small table.
Right at two o'clock, Sissy tossed the curtain aside and popped into view, topless and wearing very tiny shorts, and the ten guests applauded her. Then Liz appeared and the applause continued, but when Didi strolled out with her breasts proudly on display, the men stood up in appreciation for a new woman to gawk at. "Hi everybody," Sissy said, "This is Didi, and she has agreed to add her help today. Unfortunately for Liz and me, she's also adding her good looks and her curves." The group was easy so they laughed at her little joke. "Ladies, we're glad to see you're still topless, but you know, this isn't exactly fair. There the guys sit in their baggy trunks, but hey, they can be topless too right ladies?" Five women clapped and the chanting started, take it off, take it off, until the men peeled their shirts off and tossed them aside.
"That's a little better. But look at you women all sexy in your tiny bikini bottoms and them in these ridiculously short shorts. But okay, we can let that slide I guess. First, we need you to trade partners again. Maybe hook up with different mates this time just to make this more interesting. But if anybody sticks with their spouse, somebody snitch on them okay?" This was all new to Didi so she was smiling and having fun watching the silliness slowly unfold.
"Great, now..." and she smiled at Didi and Liz before she said, "Yes, okay guys, all of you come up here. Let's get this show going right ladies?" and they clapped in agreement. Okay boys, go with Didi behind the curtain and follow her directions."
Liz stepped forward as they had planned and she asked them, "How many of you have gone naked on the beach?" No hands went up, so she asked, "Okay, how many of you made love to your hubby in a private spot in the moonlight?"
One hand timidly went up and then down quickly as Liz smiled and said, "Fantastic wasn't it? That is one of my favorite things to do. Okay, how many of you have put something in the computer for future guests?"
All hands went up and Liz and Sissy clapped and Liz said, "That's fantastic and I hope you scorched the screen with your thoughts. "Do any of you have any of those thoughts to share while we wait for the guys?"
One hand went up so Liz pointed to her, and the woman said, "I wrote quite a bit about yesterday's entertainment, and shared some intimate thoughts about all of that."
"Now that's what we're talking about, thank you."
From behind them Didi said, "The men are ready."
"Great bring them out Didi," and the five men lined up in front of Liz and Sissy still in their baggy trunks. Nothing was different so the women just sat there, as much in confusion as anything else until Sissy said, "Okay guy," she said as she put her arm around his waist and pulled him close to her very nice breasts. I need a volunteer and you're just handsome enough to be chosen. But I need a woman to...where is your table partner?" She raised her hand so Sissy said, "Come up here and help me out would you? We want to play a little harmless game. No prizes for this one, but stick with us. Okay...your name is?"
"Heather."
"I like that name. Okay Heather, kneel right in front of..."
"Bill."
"Thank you, kneel right in front of Bill," but Sissy continued to hold him close to her breasts and for good reason. Didi came forward with a length of soft rope and went around Heather and on around Bill's thighs three or four times. "Kind of pulls you pretty close to Bill doesn't it. Okay here's what we want you to do Heather. Pull Bill's trunks down as far as you can."
Heather looked up at Sissy to protest, but Sissy said, "Trust us, it's okay, really. Where is Bill's wife?" With her located Sissy asked, "Do you trust us enough to let Heather pull Bill's trunks down?"
"Go ahead Heather, it's okay."
"There you have it from the boss. Slowly pull down on...yes, like that Heather. Good, now all the way down to..." and the other women applauded as Bill's red trimmed and sexy briefs came into view. But now Heather's eyes were just inches from the bulge in the red pouch of Bill's briefs. "Great job, how do you like the view?" and everybody laughed including Heather's husband. "What do you think Bill, is this okay? Me with my naked boobs so close to you and Heather's exposed breasts all but touching your thighs. Oh my you two are so very close and your...oh, I see you do approve," and the now focused and almost nervous group laughed at her half truth. But Bill had grown and Sissy wasn't done.
Liz pretended to whisper to Sissy, and then stepped back as Sissy said, "Heather, what if we asked you to touch Bill, would you do it?"
Heather turned her head toward Sissy so fast that her face hit Bill's quite visible bulge and even Sissy, Liz and Didi cracked up as Heather jerked her head back in surprise. "Well that wasn't part of the show," and everybody laughed again. "I was going to ask you if you had the nerve to push against Bill with the top of your head. Now not your face again hon, just your head," and that caused another light response from the women. "I'll tell you what. Do that for us and you can pick an envelope from the board." Heather had nobody to turn to. Her husband was somewhere behind her and Bill's wife didn't seem to care. She bumped Bill, but Sissy said, "Oh, do better than that. Bill is really enjoying himself, but give him another firm nudge and rub your hair against him." All eyes were on blushing Heather as she pushed into Bill and moved her head around and Sissy took his hand from around her and put it on her breast. That was obviously too much for Bill because his erection was obvious as it stretched the red Lycra material right in front of Heather's face. "Great job Heather," and Didi slowly removed the rope. Then Sissy kissed Bill and told him, "You're doing great too Bill, very nice right ladies?" and they stood up and applauded him. He pulled up his trunks and Heather escaped back to their table.
Didi joined Sissy and said, "Okay that was great fun, but I think it's time for all of the guys to get rid of those ugly trunks. What do you think ladies?" The applause answered the question, so one by one, Didi knelt down and relieved the men of their trunks and all of them were wearing the same very small red and white briefs with the red pouch that was designed to accentuate the guy's man package. "Okay boys, go back to your tables and rest and enjoy the wine, and ladies, if you'll follow me," and Didi led them behind the curtain.
As Didi and Liz distracted the men, Didi told the women, "Here's what we'd like you to do. I'm sure you remember the numbers in your bikinis yesterday. Well we're going to do that again only a little different. This time the numbers will be in the front." Didi smiled as the five women looked at her like she'd just gone off the deep end. "It's up to you just how far you put the number down the front, but think about this. You're here on this expensive vacation in this private clothes optional resort, so you must have thoughts of doing things that you'd not likely done before. Now imagine that handsome guy you're sitting with...the guy that isn't your hubby, and it's his job to reach in and find that piece of paper. It's up to you, but I say low is the way to go. Remember, your husbands will be dipping into another woman's bikini so why not the same for you? I'll give you the numbers and just let me know when you're ready. Of course there will be prizes too, but for me I'd think the best prize would be having that man's hands and eyes down close to my coochie while your hubby was having a thrill with one of your friends."
It was fun for Didi to watch the women as they put the paper in their bikini and then would look at the other women to see what they were doing. Then they would reach in and move it lower and then lower again before they stopped.
"Okay, we're ready," Didi called out, "Here we come," and the women followed Didi out and lined up again.
Liz stood behind woman number one and asked, "What's your name?"
"Brianna ."
"Okay table mate for Brianna, come up here hon." He joined them and stood there with his bulge on display as Liz said, "Okay, this is like yesterday...well sort of. This sweet lady has a number hidden and you need to find it because that number is connected to a prize for each of you. Are you strong enough to hold onto her waist to support her while you go in search of her treasure?"
He was visibly nervous, but he smiled and said, "Damn right I am Didi."
Didi stepped back a couple of feet and said, "Okay stud, find the number."
Brianna 's husband was staring and not sure what to think about what was happening. He was getting hard as stone, but at the same time his emotions were all over the place as the guy's hand went into the back of her bikini. His fingers would peek out and then retreat, but her bikini was too small to hide much. That meant the number was in the front and that thought sent his cock into a flash of full growth, so the other four women had a good view of their friend's erection as he changed position and held on to Brianna as he looked down and saw her lips just below her little token patch of hair. He saw the number right away, but as he pulled her bikini forward the paper slipped just a little lower. He looked at Brianna and their eyes locked for just a second before she felt his hand touch her mound, and she looked past him at her husband as she felt fingers touch her lips and she reached for him for balance. His fingers danced and teased, but he really was doing his best to get that little scrap of paper between his fingers. He finally succeeded and held the paper out for all to see as he continued to hold Brianna close to him. Everybody clapped including her husband, but his applause was tentative at best.