Kayla Kaye Emerges Ch. 01

I swear we were not playing Truth or Dare. My friends Lenny and Quinn were hanging out at my place to discuss our upcoming 4th of July holiday weekend at the Queen's Landing Resort when Quinn dared me to spend the entire long weekend as Kayla Kaye. Before I could answer she defined the entire long weekend as from the time I stepped out of my front door for departure to the time we arrived home on Sunday evening. She claimed that she would check my luggage for "Kent Holtz" clothing if she needed to.

I looked over to my old friend Lenny for support. Lenny is a little bit of a freak, so he was laughing and giggling and telling me to accept the dare. As usual, Lenny was no help because he loves nothing more than to strain his neck muscles trying peek at what I might be wearing. I mean, show Lenny just a hint of a brightly colored waistband of bikini brief panties and he's trying to dry hump me. But let me be clear, I may allow Lenny to get his freak on, but I have never returned the sexual favors. I have never moaned once, so Lenny is the gay one, right? And if I pushed back once or twice it was just a natural reaction, so I'm good, right?

After I thought about Quinn's "dare" for a few minutes, I agreed to accept, but with a counter offer. My counter offer had all of all us going on an alligator spotting adventure as offered by the resort in a Duck Boat and that Quinn had to enter the amateur night at Sandi's Shady Shack up in town on Thursday night, which would be the night we arrived.

I thought I knew what I was doing because asking a 23 years old Greek Goddess to show off her body was almost a sure thing and Lenny was still giggling and trying to play with my waistband. Quinn quickly accepted but insisted that we invite our other friend Allison or Ali G as we call her because sitting in a Duck Boat wasn't her thing. She also added that I take her resort clothes shopping and that I get a wig because my spikey natural hair is just "alright" and I might be able to pull off something a little longer.

I accepted and called the game because these counter offers could go forever. Quinn sat back and smiled while Lenny, well, I think Lenny was trying to secretly rub himself off. Quinn agreed to discuss the weekend away with Ali G and said the shopping spree begins tomorrow, you know, two weeks in front of the holiday weekend.

Now, I liked that Quinn offered up Ali G as a back up for the gator spotting boat ride. Allison is a true Southern Belle 95% of the time and 5% where she remembers that growing up in the south meant outdoors activities and mud. Plus, as trendy as Quinn is, only Ali G is going to pull together a cute outfit to wear in a Duck Boat. And if I'm going to be Kayla Kaye all weekend, then I'm going to need as much "cute" as I can get.

And silly me, again, because Quinn wasn't finished with playing "let's make a deal" and she made it known that she and Ali G would take the main 3-bedroom cabin and that I could stay in Queen's Hut Left and Lenny could stay in Queen's Hut Right. This wasn't so bad because the three Queen's Hut cabins are connected with raised wooden walkways with a common deck area in the middle of the triangle and if the girl's boyfriends ride their motorcycles up for a night or two, then they might need the larger main cabin.

As I was sitting there thinking about Quinn kneeling down for Derek, I kept thinking about another possible issue with Lenny. He is wearing one of those medical boots right now and that little freak might stretch it out for another two weeks, you know, so someone has to help him all the time.

As we concluded our discussion for the last time, I made two mental notes. One, call Lenny's mom and ask her about how long Lenny really needs to wear that plastic boot and two, stop by the repair shop and let Derek know that it's really hot when the guy just pushing the thong to the side before going to town on that ass. Besides, if I'm taking Quinn on a shopping spree then we can get her plenty of thongs and a two-piece swimming suit for me.

And, here we go, Lenny just pulled the "my foot" card and claimed that he should lay down in my spare bedroom for a while and that he needed a fruit bowl and that he needed another bottle of water and on and on. LOL, Quinn smiled and said "good luck with all that" and walked out of the door. I called Lenny's mom to see if she would pick Lenny up and she said "good luck with all that" and hung up on me. Fine, but I'm keeping my PJ bottoms on. I also carefully laid out the deck of cards on the table so he could clearly see that he has used more than half of the deck already.

And if I didn't mention it, I lay there like a cold girlfriend when Lenny humps me. And even though I never complained when he reached around my front and stroked my little dick, he's the one who is gay.

But he is my oldest friend, so I spoon fed him some cut fruit, let him wrap his legs around mine and wiped the corner of his mouth after each bite. And I only allow him to let his cock out because I'm a little jealous. I mean, Lenny and I are both on the smaller side, but for some reason, he is blessed down there and I'm not. And when I say I'm not all that down there, I mean wearing female clothing was an easy transition for me. Well, that and my soft facial features.

After pampering Lenny for an hour and wiping up the mess he made in his boxers, he stood up and limped out of the door and said he would stop by in a few days. I reminded him that he couldn't back out of the gator spotting boat ride and that I did not just jack him off with a hand towel. He laughed and pointed out that I used a pair of my panties to "dry him off" and that was not the first time either. To prove that he was the gay one, I shoved the cum soaked panties in his mouth and closed the front door.

Over the next two weeks, we kept updating our plans, gained approval from Ali G to attend and picked up new resort style clothing. Why the hell Quinn needs a different pair of flip flops for each of the four days of holiday, I'll never know, but the two-piece swim suit she picked out for me was perfect. It was as modest as a Soccer Mom two-piece comes, but I can already see the forbidden tan lines forming.

And with four days to go, I did everything that Kent Holtz needed to do until after the holiday weekend and with three days to go, it was Kayla Kaye all day, all night and all afternoon. Well, dark spikey hair Kayla Kaye anyways because I haven't figured out the auburn wig yet, but Kayla Kaye came and went as she pleased for the three days before our departure. And it was good because I needed the practice.

I also discovered what I really liked the best and that's Denim shorts and high tops. Oh yeah, these be me and me be happy. What I didn't like was that you can't wear a garter belt and stockings with Denim shorts because I seem to have a thing for garter belts. I even wear them without stockings because I like the way the straps and the snaps bounce off of my thighs. And yes, I have jogged in place just to feel them slapping against me.

But now, it's show time. The day of departure. The four of us are driving to the resort in my SUV and I agreed that Quinn could drive with Ali G sitting shotgun, which put Lenny the Cripple and myself in the back seat. And just to jazz it up a little, Quinn had Derek and Ricky ride their bikes over to my house just before we left, meaning Quinn was putting Kayla Kaye on display for the guys so they wouldn't be shocked up at the resort. Which I didn't really mind because I have been practicing for three straight days and because of these Denim shorts. And by that, I mean I can wear shorter shorts than other crossdressers because of the lack of a package downstairs. The smaller the used pencil, the higher the hemline can be rolled.

It turned out to be a good decision on Quinn's part because the guys almost fell off of the motorcycles and their built-in kickstands were quite obvious. LOL, Quinn made another good decision to waste no time in packing up my SUV and shuffling us inside of it and the guys down the road. I have only been out of the house a few times as Kayla Kaye and I know I have gotten some looks, but today goes down in the record books as "boners confirmed" and that felt good. Now, I'm not saying I can hold a candle to Quinn, but look at the guys driving away, you can still see them and I don't mean them as in the guys.

The 1 1/2 hours drive was interesting, to say the least. First there was Quinn. Quinn firmly believes that her tits should be let out whenever possible and most people would agree with that because, well, look at them. And then there was Ali G, the pageant queen, the trim and proper Southern Belle. Well now, her eyes haven't left Quinn's boobs since the stop sign at the corner of my street. Again, no body blames her for that.

OMG and then there was Lenny, who asked me four times if he could rest by laying his head on my lap because "driving in a car" makes him sleepy. I said maybe later and then I reminded him that his medical boot was on his right foot today. I mean, for two weeks it was on his left foot, right? What the hell? I sadly informed him that one of the reasons Denim shorts look so good is because they fit every nook and cranny like the skin on a grape, which means they don't come off or down very easily. LOL, he quickly changed his medical boot to his left foot and asked me what a cranny was.

I told him to shut it because Ali G finally came out of her hypnotic trance long enough to pass me a medium sized brown paper bag from the Large Sized Brown Paper Bag shopping store. I knew it was my Duck Boat Gator Spotting camo outfit and I couldn't wait to tear into the bag. And tear into it, I did. And it was another record books entry for Kayla Kaye because I got a boner as soon as I pulled the camo high tops out of the bag. And no, the record book doesn't need to say how small my boner is, it just needs to say that there was one.

So, Ali G, who now walks on water to me, got me these whip ass camo high tops, a dark green pullover shirt, camo shorts, modest camo shorts mind you, dark green socks, a light camo short sleeve jacket and an army style hat. I'm telling you, if I could satisfy a woman, I would be all over Ali G and making her scream with delight. LOL, that is the funniest thing I ever thought of.

As soon as we arrived in the resorts parking lot, we made sure that the guests Quinn almost ran over were alright. The next thing I did was snap off a few photos of Ali G because her blouse was unbuttoned quite a bit and that belongs as a "first" in her record book. And then I quickly pulled my Denim shorts zipper up and fastened the button and wondered just how the hell that sneaky little Lenny managed to do that. Of course, right after that, we all told Quinn to put her tits away before we checked in. And of course, Quinn is on holiday and that's as far "in" as they are going for the weekend.

Like most upper end resorts, we were quickly surround by people who wanted to help us with our luggage. That's when Ali G, the sensible one, stepped in and sent four of them back to their girlfriends and families and had the two resort staffers grab our bags from the back of my SUV. She also chimed in when the staffer with the Carlos name tag grabbed my belt instead of my backpack. I didn't back away from Carlos and his grip, but I did ask if the resort had a wheelchair for Lenny, who was distracted by trying to figure out which foot the boot was supposed to be on, again.

The resort Manager, Lydia, came out and stated that her staffers would get Lenny safely to his cabin before "too long" and that we should proceed to the check in desk. Quinn reminded Lydia that Lenny has the Queen Hut #2 or in other words, "way over there" and asked what other services the resort offered.

"The Queen's Landing Resort is a full-service slice of paradise. Hot tubs, full body massages, meals from sun up to midnight, the Bar-Restaurant hut on the beach, sun bathing, the flat lake, a few things we can't say out loud and these coupons for amateur night, which I believe is something you may be interested in."

"What do the coupons get me, I mean us?"

"You can redeem them for a matching Queen's Landing Bra and Panties set which includes a logo crop top. You can redeem them in Gift Shop and Sandi's will comp all of your expenses, just as long as you wear the Queen's Landing clothing."

"Cool. What's the Queen's Landing fresh meat policy?"

"Well, I'm sure James already has your head shot posted in the "game room" by now and your goth friend has an invite for a personal tour of the grounds on a golf cart from Carlos. And if you give James another minute, he will have the red carpet on the front porch for the prude queen. So, how about a few introductions so I don't have to address you guys with lewd names and titles."

"It's about time. I'm Kayla Kaye, the statue is Quinn and this is Allison, or Ali G as we call her. So, it sounds like we have tonight covered at Sandi's Shady Shack, but what about tomorrow night? Quinn and Ali G's boyfriends will probably join us to get their dicks wet and I will be avoiding Lenny. Do you have any events planned?"

"We do. We have Fire Dancers performing tomorrow night right in front of the Bar-Restaurant hut between sunset and 11 pm. It's adults only because they aren't very good and have burned most of their little uniforms away. By the way, if you guys are from New Jersey and you live for hair spray and gel, please stay back as far as possible. I also see that your group has signed up for gator spotting on Saturday night. That's always fun and Captain Stan is almost finished with his rehab. There is a good chance that you all make it back to shore."

"Sounds great Lydia. We are all very excited. So, what should I expect during my personal tour of the grounds?"

"This is the time of day when Carlos makes his rounds on the Golf Course to make sure we don't have any gators just wandering around. We don't hurt them. We just chase them back towards the swamp. By the way, our stud staffers prefer our female guests to "wandering around" between the first and second Fire Dance show. There is a Boat House just to the south of the Bar-Restaurant hut. Go ahead Kayla Kaye, we will take care of your freaky little friend and we will submerge these two hotties in the best body oil in the state. I will personally see to it."

"Because you have a little freak in you?"

"Duh, I do now. Have you seen your friends? I will also meet Quinn at Sandi's tonight because, hey, her skin tone demands an "oiled up" look, am I right?"

End Kayla Kaye Emerges 01"

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