Best Bet I Ever Lost

"Just push it" my mind told me. "This could be amazing!"

My finger hovered over the button of Kaye's apartment. Why couldn't I push it?

As I tried to answer that question, my mind did one of those sequences where an unbelievable amount of prior events flash by in an instant. Probably similar to what they say happens as you die, your life flashes before your eyes. In this case, the past 8 hours flashed before mine.

:::::::::::

It was another long flight across almost the whole country. From L.A. back home to Atlanta, nonstop. Close to 5 hours. Well, it would give me a chance to finish off that Tom Clancy book I had been trying to finish for what seemed like forever.

My boarding pass said that I was in the middle of a set of three seats, but the flight was so short notice that I had no choice. Maybe the window seat holder won't make the flight! Yeah right, that never happens. I do prefer to read by natural light when possible.

When I got to my row of seats, the window seat was still open. Great! There's hope! I planned my slide into that seat once the cabin door was closed, which was still about 10 minutes away. My normal optimism kept me from getting too settled in. Why settle in when I'll need to settle in one seat over in a few minutes, right? I could feel it. This was my day. I was gonna get lucky.

My mind went back to the office, wondering how they all did without me there for the past two weeks. I didn't get any calls, and only one text. And it was a silly question from Chloe. If she would have just checked with Connie she would have had an answer. And probably a much better one than I could give.

I'd only started there a little over a year ago, right after I retired with 20 years in the military. I was so lucky to have Connie working for me. She could do my job easily, why they slid me in an office to supervise 11 women I have no idea. That kind of thinking should have gone out the window back in the 50's. My position should have been Connie's. She's so bright. So sweet. So genuine.

And so young.

I like to think that she looks at me like a father figure, but there is something unsettling about the whole situation. At least on my end. Shit. I want her, I might as well admit it. But I can't. I would only be bad news for her. Chloe once told me that Connie sometimes looks at me with 'that' look, but that's just Chloe being Chloe. She's such a gossip, and thinks everybody should be involved with somebody. Since both Connie and I both presently aren't, well, two birds, meet stone.

There can't be more than one minute left now. It's gonna happen. I think the stewardess, oops, 'flight attendant' is going for the cabin door. Wow, old habits die hard. Through the first 15 to 20 of my 39 years on this earth, they were simply called stewardesses.

Wait, what's this, the door didn't close. Is there someone else? Nope, just another stew, er, screw it, stewardess. I recognize the 'look' but this one is an allstar! I hope she's covering my part of the cabin! Her 'look' gives off a more down to earth vibe, than most, ahem, 'flight attendants' did.

But what a minute. She doesn't have the same 'wings' and other flair on. It's just a navy polo similar to what the crew has on that threw me off. She's a passenger, and, heading my direction. Nah, it couldn't happen. I tore my eyes away from her ever increasing presence.

"Wow, I can't believe I almost missed this flight. TSA is insane at times, you know? I hope they got a good look at me with their scanner, they made me stand in it long enough. My roommate would be pissed if I didn't make it home, she took off work today to come get me at the airport."

"Ummmm..." Wow, great job Griff. Make that first impression unforgettable. "yeah, I've been hung up with them before too. This trip though, no issues. I'm sorry you did."

"Oh don't be sorry, it's not your fault." Then she looked directly through my eyes to the back of my brain. "Is it?"

"Ummm..." Suddenly she gave me the warmest devilish grin I had ever seen. "Gotcha!" She quickly held out her hand, "I'm Kaye. Looks like you'll have to put up with me all flight!"

"I'm Griff, and nice to meet you. There won't be any blood or contusions involved will there? Any ritual sacrifices or anything?"

"No Griff, well, unless you want there to be!" I loved her subtle, smoky laugh.

"Well, sounds good to me." Mr. Clancy was now not even an afterthought. And natural window light is really way, if you think about it, way overrated.

Lucky indeed!

More small talk for awhile, where I'm going, what was I doing in L.A., then this:

"So, I see no ring, and no trace of where one might have been but had been removed because of a trip away from the wife and opportunities for some 'strange' ..... are you single?"

"Wow, please, don't sugarcoat it, just ask me direct! And funny about the ring comment. I bet someone such as yourself probably gets that a lot, getting hit on by married guys pretending they weren't. Sounds like you have the routine scoped out, and can weed through those kinds of guys."

"Well, thank you for assuming I get hit on a lot. Because to be honest, I do. But there aren't enough approaches from young, witty, good looking guys like you."

"Hah! Young? Please. And I won't even touch good looking. Witty? Sure, I'll take that and thank you. How old do you think I am?"

"Well, I hope this doesn't insult you but, 30? 31 ummmm-ish?"

"You're right, you said I was in for it. You should have added 'gotcha!' to that one."

"I'm serious, that's how old you look to me. The shape you're in makes that even more obvious in my mind. I KNOW guys, trust me. OK, fine how far off am I?"

"Try 39." I had thought about taking some liberties and shaving off a few years to get into those 'mid-thirties' but decided better of it.

"No way, ohh, I get it, you're getting me back! Gotcha Kaye! But really, how old?"

I quickly realized that no matter how hard I protested, documentation would finally be required, so I pulled out ID and showed her. She just sat there shaking her head. "I'm sorry, but you absolutely do NOT look that old. You have really taken good care of yourself! I'm impressed!" she said with a gentle clutching of my forearm. Electricity shot through me when that happened.

She wasn't the only one, I was impressed by her understated beauty, and also with her spirit, her enthusiasm for life.

I was also thanking myself inside for the decision I made to take my buddies suggestion to do the P-90X program while I was goofing off those last few months in the service, while I used up all my months of leave before my retirement took effect. It had been brutal at times, but it had also transformed my body into shape that it had, well, never been in.

I was also glad that my sister told me 10 years ago to quit with the tanning beds and to moisturize, moisturize, moisturize! Because apparently I didn't look Close to my years. But I was surely too old for...

"Kaye, now that we know how old I am, how many years did it take you to get to this incredible level of 'age-dar' that you possess? (as I rolled my eyes, followed with a wink) Gotcha!"

"Griff, if that's your slick way of asking me how old I am, I won't fall for it. But I'm 25. And I told you that because, well, I wanted to, not because you're slick."

"So what do we do now Griff? You know any good jokes? Card tricks? Do you do impressions?"

"Well, all my best jokes are old, Impressions, ummm, no. Were you serious about cards? Not a trick, but I learned Gin Rummy a few years ago, and really took to it. But I am always ready to hone my skills some more. Helps me win some bets at times."

"Sure Griff, I know Gin Rummy. But I hope I don't drag down such a professional as yourself. Let's do it."

Kaye unbuckled her seat belt and I got another lightning bolt through me as she brushed my arm as she stood up slowly.

I instinctively looked at her ass, as I always do when presented with that view. Hers was incredible. Her khaki's were glued to her it seemed, but no VPL.

Heh, where did I first hear that? VPL, the visible panty line. Who thinks of these things?

But that's one of my favorites. That along with DSL's. DSL's could very easily be taken as degrading, but it is also incredibly descriptive.

Kaye started down the aisle to find some cards, and I watched every delicious step. About two steps in she casually looked back, and by the time I realized it and forced my eyes north, she already had that 'oh you are SO busted' look on her face.

She returned with the cards and we continued our light (and sometimes not so subtle) flirting as we played. Sadly I beat her easily, but even though I lost an opportunity to sharpen my skills, I wouldn't trade the time verbally sparring with her with so much innuendo for the world.

Kaye said "I can't believe my luck, this shouldn't be happening. I am so much better than this, I'm serious."

"Oh Kaye, of course you are" as I rolled my eyes with a concluding wink and a smile once again.

"OK big guy, you ready to put your money where your mouth is?"

"Kaye, quit while you're behind. Please, because I love your behind. Yes, I know, I was busted. Guilty!"

"No, I'm serious. I can do this. Let's bet. Unless you're scared..."

"Kaye..."

"No, what are the stakes?"

"Ok, loser has to haul the winners luggage out to their car, or taxi, or whatever they may have. I'll be taking a taxi, so that's where you'll have to haul my gear to."

"No, that's small time. Let's make this worth it. Loser has to be the winners slave for a day. 24 hours from the end of the game."

"Huh?, what are you saying?"

"I mean the loser has to do whatever the winner says."

"You serious? What if the winner wants the loser to do something illegal?"

"Well, of course I won't get you arrested Griff, that wouldn't be showing much southern hospitality now would it?"

"Oh, I'm gonna be on the losing end of this? Ok, you're on sweetie, and I'll try to be nice."

:::::::::::::::::::::::::::::::::::::::::::::::::::::::::::::::

So I was eight hours into my 'service' to Kaye, as she told me she wanted it called, and I was afraid, and excited, about what the next 16 hours might bring.

When it comes to Kaye, I had unfortunately discovered that she was a Gin Rummy hustler, just like those pool sharks you hear about, the ones that sucker you in by letting you win in the beginning then crank it up when it's really on the table. She bagged And tagged me.

I pushed the buzzer. "Hello?"

"Kaye, it's Griff, can you buzz me in?"

"Sure Griff. But remember our agreement? First I want you to go down to the corner magazine shop, and ask for, and bring me up something."

"OK, what can I get you?"

"A Playgirl magazine."

"Ummmm..."

Kaye gave me that amazing laugh again, "I'm kidding, they don't even print that anymore silly! Come on up, 6C. Gotcha!"

Kaye had the door cracked, but I knocked anyways, out of habit.

"Come in, we've been expecting you!"

"We?"

"Yes, Griff, this is my roommate Amber."

Amber was somewhat taller than your average girl I would say, maybe 5' 8" or so? She also had what appeared to be very large breasts, at the moment somewhat covered under long dark brown hair, and a set of hips that you would just want to instinctively grab a hold of. Although very young, maybe 20 or 21, she was all woman. To me she was a throwback to old Hollywood.

"Hi Amber, nice to meet you."

"You too Griff."

And with that, Amber went to what I assumed was her room.

"So Kaye, what doom are you going to lead me too?"

"Oh, I have plans, you won't believe them. But stand still for a moment, you have a spot by your eye."

I reached up to swat it away, but Kaye stopped me mid swipe.

"Let me get it." She reached up towards my eye, then slid both arms around my neck and pulled me in for a kiss. A kiss unlike any I had had before. She took charge of the kiss, appropriately, as I was the slave. Her tongue pushed, danced, parried and relented in a wonderfully intricate and erotic way. I felt silly for thinking this, but all that I can think of is "this girls been kissed, and has kissed, a lot, before."

I very unservantly swooped her up into my arms and carried her to the ... bathroom.

"Smooth, Griff. One more door down the hall please."

"Oops" I said with a sheepish grin as I continued on. I went to lay her down on the bed, but somehow she ended up pulling me down.

We pulled each others clothes off in a flurry. She pinned me down and guided my already hard cock into her already dripping snatch.

After a few minutes of strokes, I asked her to turn around, for a little reverse cowgirl action.

"Why?" she asked. "Because I need to see that ass!"

"Too bad slave, my party." Kaye said as she reached behind her and grabbed my balls, paused for a second, and then squeezed them with authority.

That was all I could take as I shot load after load of cum into her as she came at the same time.

I stayed hard for as long as I could, and Kaye kept gyrating on me, using my hardness and came twice more, the second time after she turned around to give me the view I wanted so desperately to see, and before my penis finally plopped out of her with a 'thwack' on my upper thigh.

She laid down beside me, put her head on my shoulder and gently played with my nipples.

"See, I told you you wouldn't get arrested."

"But you might, I think you killed me. Or my penis at least."

"Oh yeah, that." And with that she slid further down, and looked at my package, studying it.

She gently lifted up my balls and weighed them in her hands.

"Damn your balls, ... they're HUGE! I thought something was different when I squeezed them, and I was right! Holy shit! Do me a favor, go get my camera, this I have to record!"

"No, Kaye ....."

"Slave! Go get my camera!"

I paused, well, it wasn't illegal. It wasn't the first time they'd been photographed anyways, and with the same reaction too. Way back in the middle 90's, probably around the time Kaye was five, I had posed for nude pics for my girlfriend Kelly.

I had taken pics of her a week before, and she wanted to do the same to me. Who was I to object? A whole roll, 20 pictures were taken.

Back then before the mainstream digital age, we had to use film, and then get the film developed. Little did I know that Kelly took her friend, you know, that one friend that your partner always seems to have that usually tries to get them to do things that you wish they would rather not do?

Well Kelly had a friend Karen, and Karen took her to the drugstore to pick them up after a few days wait.

Kelly told me that when they got back in the car that she let Karen look at them one by one as she, while pretending to be writing a note to her landlord, wrote down what Karen said, to tell me later. Kelly always had embraced and been entertained by my nudist kink.

The one comment that sticks out to me to this very day was: "my gawd, his ball's are ... HUGE! Not that they hang real low or anything, they're just, just HUGE. Did you starve him from sex for a month or something?" Kelly said, no, they were Actually properly drained just about an hour prior to the photo session, as a matter of fact.

I suddenly liked Karen when I heard that.

"OK, where's the camera?"

"On top of the fridge."

I rolled out of Kaye's bed and reached for my pants.

"Uh, uh, no, go like that."

"Kaye..."

"No, you're right. What was I thinking. Come here."

I walked over to the edge of the bed as she reached into the night stand and pulled out a ribbon of some sort, which she then tied around my dick and balls.

"There. Now go. And if Amber is out there, don't let that stop you."

I peeked out, and could see Amber sitting on the couch, typing away on a laptop.

I gulped and quickly walked towards the kitchen.

Amber stopped me halfway. "Griff, you didn't play her in Gin Rummy did you? She's a shark!"

"I know, I know... so I'm not the first, eh?" as I kept walking briskly towards the kitchen.

"No, but you're the ballsiest, I must admit!" Amber said as she giggled.

Kaye took her pictures, and then pulled me in for round two, which thankfully lasted much longer, boosting my "performance pride."

We laid in bed basking in the heat of what we had just shared, when Kaye asked: "Oh, was Amber out there?"

My face gave me away.

Kaye said "I like to do that, to give her a show. She's painfully shy."

"Well, for someone so shy, she didn't look away much, at all. In fact, she stared! No, not really, but she did take it all in."

"Well, good for her. You didn't mind too much did you Griff?"

"Honestly, no, I should probably thank you. I actually have a bit, well, more than a bit, of an exhibitionistic streak in me. So letting an almost absolute stranger, a cute young lady like Amber see me, pretty cool. Thank you." I then lightly kissed Kaye's forehead.

"Griff, first off, I love men with brazilians like you have. Secondly, do you have a fuuuuun night ahead of you. But before we get to that, let's go shower, and see what comes up..."

After session #3 in the shower, we both got dressed. We got in Kaye's car, with her still not telling me what service I was scheduled to perform.

We drove in silence for a few minutes, then Kaye finally said: "Griff, today has been amazing. It really has. You've given me so much pleasure, and I think you had some fun as well."

"Are you kidding?! You know I have!"

"Well, I'm going to be mostly altruistic with my next adventure, and you get to help."

"OK, but I gotta say I have no idea where you are going with this."

"Well, I have an aunt that I just adore. She's my mom's older sister."

"Umm, you're not ..."

"Ha, no Griff, I think I know what you're thinking and gawd no! Damn, full body shiver on that thought!"

"Whew, you had me worried for a bit!"

"Anyways, ever since her husband, my uncle Bob passed away, she has been spending time with this group of girls she runs around with that she has known almost her whole life, and they do a bunch of stuff together. Volunteering, Bingo, taking cruises, and also, and this is where you come in, taking art classes. Are you getting a clue yet?"

"Yes, i think I am. How old is your Aunt, this group?"

"Well, it's not just her group, there are about 5 in her group, but the whole class has about 10 to 12 people in it."

"I keep waiting for you to go "Gotcha!" It's not coming, is it?"

"No Griff, this isn't a joke. But I think you're up for it, I just have a hunch." Kaye then reached over and squeezed my already aroused cock.

"Well, I'm not ready to jump out of the car yet, but it is, well, not something I would have ever thought of. You never said how old they were."

"My aunt is 67, and the rest of her group is probably close to the same age, they all grew up together."

"Any guys in this class?"

"Not that she has ever spoke about, but I've never been there. There could be. We talked today, before you came over, and I told her I was pretty sure I had a male model for them, like they always wanted. She's mentioned wanting to get one for the class a few times. At first, I wasn't sure she was serious, but now I think it's great. So you are expected, and she assures me the 'girls' will be very excited to see you!"

"Oh great! Griff strips for the Golden Girls, ha! What exactly am I supposed to do? What's the setup? And I may be getting ahead of myself here, but how strong is the A/C there?"

Kaye, gave out another of those awesome laughs

"This is gonna be great. But I gotta tell you, I have no idea about the A/C. Good luck with that one! But they're only 20 some years older than you, it shouldn't be that awkward, right?"

"Sure, but whatever happened to "you look 30?" That's 37 years older!"