123. Mischievous Mike and the Swim

I am sharing some of the events that Mike and Kayla shared with me regarding their trip to Florida together.  I previously shared their silliness at the airport, and will now share another escapade of theirs that I call, “The Swim.” 

I want to remind you of a few things so you understand a bit about what Kayla was feeling during these experiences.  You can learn more about her on Post 91 Undressing Kayla.  She is the admittedly “quirky girl” and shy, at least in groups – she has never been shy around us.  She is overly self-conscious of her looks, even though she is beautiful.  While she seems a confident and vibrant 22-year old around us, in many ways she is like an insecure 14 or 15-year-old when in public or especially when around people her own age. She has always been more comfortable around older people.  Throughout school her friends were always several grades ahead of her and today, her friends are all in their late twenties to early thirties (and then of course there is us).  I restate this to give greater context as to the impact the experiences I am sharing had on Kayla.

Mike told Kayla to purchase a two-piece bathing suit for their upcoming trip.  He said that it needed to be “skimpy.”  Mike knew that would be difficult for her.  I mentioned before she has been around my family for many years, even on vacation with us.  In any swimming activities she always wore a one piece.  Too shy and self-conscious to attempt the bikini.  

She bought one and tried it on for Mike and he told her to return it – not skimpy enough.  He even spanked her for not following his orders to buy something skimpy.  He called it “revealing but not skimpy” and sent her back to purchase another.  He was happy with the second purchase – low cut all around so there was both some cleavage action and had both some side-boob and bottom-boob action.  This link is a fairly good representation of the top.  The one she got had a little more coverage than that one, but, it gives you a good idea. It required frequent adjustment while wearing it to keep the boob coverage publicly presentable.  The bottom was skimpy too.  Small and tight in the crotch and, while not a g-string, it showed a lot of ass.  This link shows one that was fairly close to what her bottom looked like from the front (it wasn’t a g-string though).  

He asked her how she liked it.  Having to be honest she said, “I like it because it is what you want for me.”   He asked if this was something she would wear if he didn’t require it.  Without hesitation she said, “No, Sir, I would not.”   “Good, then I know for sure it is the right one for you,” he proudly said.

They went down to the pool as late as they could and the only people there was a table of what turned out to be college aged kids.  Mike told Kayla she wanted her to “flaunt” her body.   She made big sweeping adjustments to her top, and when she did she gave them an innocent and incidental  flash of her boobs – which they clearly saw as they were already checking her out. 

Kayla, being on a bold streak after the airport experience,  not only did that, but made eye contact with the group as she “adjusted” and said, “Oh, hello y’all.” 

Mike and Kayla were in the water at one end of the pool.  Mike embraced Kayla, wrapping his arms around her, and told her, “I want you to swim the length of the pool and when you reach the wall on the other side, stand up, wipe the water from your eyes, and then swim back to me.  She did so.  This time he told her, “Good, I want you to do it again, but I want you to have a wardrobe malfunction. I want you to lose your top just a few feet from me but keep swimming.  When you get to the other side, stand up again and give a bit of a shriek and yell, “I lost my top!”  I don’t want you to go back under the water and I don’t want you to cover yourself with your hands.  We will just ad-lib it from there.

She did as she was told and of course when she shrieked, the guys all looked over.  Kayla then said, “Where did my top go?”  One of the guys at the table pointed in the water near Mike, “there it is.”   The guys looked over at Mike and as he retrieved the top he said, “Well, you might as well get a good look before she gets it on.”   Undaunted, Kayla gave a pose and cupped her boobs together and said, “Well, if he wants you to have a good look, then let me make them easier to see.”   Mike then tossed her top, not to Kayla, but out of the pool near the table.  Mike said, “Go get it.”

The young men just laughed and looked over at Kayla as she had this surprised look about her.  One of the guys got up and said, “I’ll toss it to you.”  Kayla, knowing that Mike is purposely trying to embarrass her and feeling confident after her “win” over his last attempt to do so, said, “What’s wrong, you don’t want me to get any closer to you?  Just leave it and I’ll come get it.”  

With that she swam back to the end where Mike was. She told Mike, “Now would like me to lose my bottoms, Sir?”   Mike had played a few games like this before with her, but this trip was like “major league” play.  Yet this rookie Kayla really knows how to play this game.  She totally flipped the script and instead of Mike pushing her, she was the one pushing to see how far Mike would take things.  

Mike told her to leave her bottoms on and to retrieve her top.  In telling me this story Mike said he had Kayla leave her bottoms on only because he was concerned there could be kids coming in or it could cause trouble.  I slyly told him, “How convenient, Sir, are you sure it wasn’t the fact that you were simply the first to blink.  Sounded to me like Kayla was ready to go further.  I think she wins again.”

Kayla 2.  Mike 0. 

Kayla said, “Hell yeah  I won, and I even took it further.  Let me tell you about my victory lap!”  Turned out when she got herself out of the pool and walked over to her top she told the guys at the table, “Here’s a closer look.  Look all you want.”  She then took the top and sort of half put it on.  She  then asked one of the guys to tie it for her. She purposely let one boob hang out for some time before “noticing” she needed to tuck it in.   Once the top was secured she looked down and said, “Oh, you can barely see my nipple through this thing.”  With that, she stuck her hand under her top and tweaked both nipples for about ten seconds.  “There, don’t you all think that looks better?  Thanks guys. Isn’t Orlando fun?!”

She then went back into the pool and embraced Mike and laughingly said, “Sir, I will do anything for you.  Although I am full of embarrassment, I can always will myself to surrender to your will.  I am all yours and my embarrassment is not as important to me as my service to you.”  They stayed in the pool a little longer, and then got out and went over and talked to the guys for a bit.   That’s when they found out they were in college.  It was two pairs of brothers who were each other’s cousins Did I explain that clearly?  Whatever – not important to the story.

While Mike generally likes to win at these games, he was now even more motivated since he had  “lost” twice in a row.  Could he actually conjure up a public scene that could break her will power?  Of course, this is bounded by what is safe, sane, and legal, as well as her hard limits.  Other than that, it is only limited by Mike’s imagination.  Well, Orlando is the land of magic and imagination.  He had more in store for her the next morning. 

NEXT: 124. Mischievous Mike and the Room, the dance, the term, and the treat.