Sissy Loni on the Big Island Ch. 07

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Steve, now signaling with pointer finger, wants me back up next to him. We spend another few minutes kissing, little words, a little pillow talk... He compliments the skill, the devotion I just demonstrated, and we share genuine affection for each other... We catch our breath completely, both of us have small smiles on our faces. We are both content...

Finally, we're back to normal, talking again about our routine things... Steve starts: "Ok, now, NOW I am ready for more coffee!"

I look to find the mugs, mine is on the night table. Somehow, during the last thirty minutes, Steve, who started out watching me perform oral sex on him with his coffee mug on his lap, in his hands, has lost his cup! I find it, tipped over, under one of the pillows... "Uh oh, Daddy!" I giggle to him, pointing to the empty cup.

"Good thing I drank that mug dry before you made me lose total control of my motor neurons!" Steve laughed. Not too much spilled coffee, just a few small spots on the sheets... We both chuckle.

"Ok Daddy, follow me to hot coffee land!" I say in my best sissy voice, holding a mug in each hand, I jump out in front, and head down the stairs, thinking this will give Steve another good chance to check out my bum..." Why not, I lift the robe material up at the waist, about six inches or a foot upward, which lifts the hem up in the back, providing for an unobstructed view of my cheeks. My bare ass swivels back and forth as I walk down the stairs to the kitchen.

Long story short, the rest of the morning, more coffee, breakfast, and we retired to our respective rooms to check email and our other chores needing attention. I straighten up my suite a bit, I've been flinging clothes around in here since I arrived! Around ten a.m., Steve pops his head in, "We're going to leave at eleven, ok? And I've got to shoot down to the pro shop right now, ok? Be back in fifteen minutes."

Sure enough, fifteen minutes later, I hear the garage door open and the Porsche pulls back in. Steve walks through the entry door, and again pops in on me, I'm browsing the shopping options here on the big island on my laptop. Walking over to me, he first kisses me on the cheek, then hands me a decent sized shopping bag with the resort logo on the side. "I had one of the young ladies in the golf shop help me pick out a few things for you."

"I want to take you out on my boat tomorrow, at the very least, we'll cruise around the west side coastline. We can lie out in the sun on the deck, bring a picnic and some wine, and maybe even stop out at Captain Cook's Cove and do some snorkeling. If we go into the water tomorrow, I'm thinking that neither your wig nor your breast forms are going to work, which honestly, is just fine with me. You know..." he says, smiling at me, "you're a cute little sissy even just showing off your little boi nipples and titties under a sexy top... That hot little bikini you wore yesterday would be fine, maybe throw a tank top on over it, if we go snorkeling? But then, you'll need some cover-ups to wear on the drive to the marina, and then home. So that's what's in the bag, there's a two-piece casual short and top set, the gal called it a 'resort romper' and a matching hat. Supposed to be very nice, per the young lady in the shop: 'Lily Pulitzer', do you know that brand?"

"Yes, Daddy, Pulitzer is a very nice brand, nice stuff, it's the Country Club look!" I look in the bag, pull out the romper set, very cute, a busy floral pattern, with a lot of different pinks, purples, and baby blues. I look at the label, 'Ritz Resort Romper by Lilly Pulitzer': a strapless top and elastic waist short shorts, I hold them up, one at a time, to show Steve... "Very sweet and femmy, thank you Daddy!" And the hat, I pick up now and look at it, it's a woman's golf hat, all pink, with an oversize visor. "Hualalai" the name of Steve's golf club, on the front panel. "Ok Daddy, I think the ONLY way I'm going to get this to fit on my head, is without the wig... It's nice... Maybe I should take up golf?" I giggle on that last sentence... I wink at him: "I'd get to play from the ladies' tees, right? And before we'd tee off, I'd be happy to kiss your balls for good luck!" That was corny, I realized, and even I roll my own eyes after that joke left my mouth...

And then I continue: "And now, back to today, we're leaving at eleven, right?" Looking at my phone, to get the time, "that gives us forty-five minutes. What's the dress code for the airplane ride, for the afternoon?"

"Casual, very casual..." my Daddy answers. "Thinking maybe we could go to Kona Brewing Company afterward, for a bite to eat and try one or two of their craft brews. Casual... 'Casual Sexy' maybe" he laughs. "Can you do that?"

I walk up close to Steve, put my arms up around his neck, looking at him in the eyes, I reply, "I'm going to try my best, Daddy!", and then I lean into him, and we kiss, a nice, sensual kiss on the lips, with just the right amount of tongue. Still holding on to him, I continue: "But now, I don't even have forty minutes to get ready, so you need to let me get ready!"

Steve smiles, and nods. "I'll be back down here at eleven on the nose!"

My Daddy heads upstairs, and I head to my bedroom, to lay out some stuff to wear for the afternoon... I look in the closet and through the dresser drawers, looking at everything, I think to myself, "you certainly brought enough stuff, Loni, most of the stuff hasn't even been touched yet. I'm thinking to myself, "Now, Steve said casual sexy..." smiling to myself, I flip through my stuff, and find a little outfit that should be perfect, from Billabong, they have a lot of surf and beach related stuff, I did a big order from them a while back, mainly for summery stuff... I chose their 'Road Trippin' Stripe Shorts' and 'Tomboy Tank' top. The bottoms are a very short, but loose-fitting summery rose-colored striped shorts, with a tie at the waist, the white tank top is not very revealing at the top, I can wear my breast forms underneath today, and the top will cover them just fine. I can accessorize this just fine, I think, and jump in the shower, a quickie.

Then the rest goes quickly, makeup gets done, I look at my finger and toenails, everything good there, a nice deep glossy pink, I put the Hawaiian sandal necklace back on, to accompany my day collar. Did I mention, I think I want to wear the collar the whole rest of the time I'm here with Steve... Little blingy bracelets, I slip on these Billabong Cross-Over sandals, they're flats, but I love the skinny little gold straps, so sexy... they'll draw a little attention to my pedicured tootsies, I think to myself and smile. I can take the resort top I wore yesterday, in case it's cool enough to need it wherever we go today... Back to the mirror, two nice thick coats of glossy pink lipstick, I'm just about ready! I grab my sunglasses, hat, and little clutch purse, and I'm ready to go...

And good thing, it's just now eleven, and I am learning how organized and punctual Steve is, he's at my door, at the minute... I turn to him, I think this must be his summer uniform: khaki shorts, today with a peach-colored silk shirt, and sandals. I extend my arms away from my sides, and spin around... "Will this work?"

"Wow, wow, wow, you've done it again. How about we just stay home, and I'll eat you all up?" he chuckles.

"No, Daddy, NO!" I say, giggling... "Take me to the airport! I'm SO excited to do this..."

It's a quick trip, the top down, my hat tied on, oversize sunglasses, I've got that movie star feeling again in my head, just can't stop smiling... The airport's close, ten or fifteen minutes, and we see the signs for general aviation, its south of the passenger terminals and the access roadway. Finding our way to the appropriate little parking lot, Steve cuts the motor, puts up the top, and we head out to the airplane.

Steve starts: "Look for the royal blue and silver Cirrus..." There's about a dozen or more single propeller airplanes scattered in a couple of rows. I look around, and spot it just a few seconds before Steve... I point toward it, we walk over to it.

"My God, this thing is beautiful..." I don't know what else to say...

"The airplane? Or Bill?" Steve asks, with a slight chuckle. The man walking around the airplane, looking it over, sees us approaching, and walks toward us, smiling.

"Bill! Thanks so much for letting you twist my arm and agreeing to take us for a ride today. This is Loni, a friend of mine from California, she's visiting the Big Island for the very first time this week, staying with me..."

"No problem at all, Steve... been itching to get out there, haven't flown in a week. And you always take care of me when your wine shipments come in from the mainland. I love those big reds you send my way!"

We exchange pleasantries, Steve wasn't kidding at all, Bill is handsome! About as tall as Steve, he's not as thick in the torso, not as muscular, but tanned, and a nice full head of sandy blonde hair... Wearing khaki slacks and a gauze white long sleeve button down shirt. And, the requisite mirrored aviator sunglasses, which he lifts up off his sky-blue eyes, and leans into me, "Let me help you up.", and holds out his hand... I'm thinking he could model clothes for Ralph Lauren... Not sure why I noticed it, I see a gold wedding band on his hand, as he reached out for mine...

We walk up to the stairs of this blue and silver beauty. Before letting me go up the stairs, he stops to mention: "Isn't she a beauty? I got her just a year ago, it's a Cirrus 22T, there's not much out there nicer than this baby unless you're talking about personal jet aircraft. It's the airplane equivalent of a BMW or Benz..."

And now, leading me up into the cabin, I can see. I think to myself, "Are all airplanes appointed like this? Leather seats, wood grain panels, wow!"

I move into one of the back seats, Steve joins me, and points to a pair of oversize headsets, the kind you always see on pilots in the movies. I pick mine up, it's cordless, must be Bluetooth... We both adjust our headsets, Bill hops in the pilot's seat, and we're fired up and after checking with flight control, we're taxiing to our runway. Very cool, we hear each other, the three of us really well, and you can hear the people in the tower, too. I squeeze Steve's thigh, it's exciting! He, in turn, rests his big hand on the inside of my bare thigh... Here we go!

Well, almost a two-hour tour, it went like a blur. We flew over the top of the world's most active volcanoes, Kilauea and Mauna Loa. No active lava right now, Bill told us, but there was plenty a few years' back. We got great views and a bunch of photos of waterfalls, lush valleys, rainforest, beaches, cliffs and the coast. Out over the ocean, we even saw two mama whales with their babies! And the whole way, although I barely looked at him, my eyes glued to the landscape, Steve's hand never left my thigh the whole way. Whether sightseeing, or talking with me or Bill via headset, I enjoyed Steve paying attention to me, stroking my inner thigh, and a few times even, making a foray inside the hem of my shorts, to reach up and stroke my little clittie with two fingers...

Before you know it, it's over. The airplane is parked, we are departing... We say our goodbyes, after profusely thanking Bill for the awesome experience. After the last goodbye, Bill adds one more thing to the short conversation: "Loni, a real pleasure to meet you today, you are a lovely young lady! And I understand..." he says, continuing... "That I will see you again, tonight, at the card game?" He's wearing a smile on his face the Cheshire Cat would envy...

Oh... My... God...! I hope Bill didn't see my surprise, the shock in my eyes. I'm certain my eyes, my eyelids opened up wide! Well, I swallowed, and searched for something snappy to say: "Well, I'll be there, since I'm here for the week, Steve has asked me to help host the game tonight. I'll be bartending, and making some snacks for you handsome guys... I'll be there, with bells on!" I tell him, giggling during that last part.

I look at Steve, just a glance, my eyes sideways. He mentioned that he told them, that his poker buddies knew 'all about me'. So I'm thinking, if Bill is one of these guys, he knows I'm a sissy boi, a sissy with a boi clittie! Ok, I'm good with that, and doubling down, in an exaggerated way, I blow Bill a big kiss: "Mwah! See you tonight, Bill. Good thing I'm not playing tonight, I'd tell you I'm going take all your chips away from you!"

A little wave to Bill, then I turn to Steve, "Ok big boy, let's go... I'm ready!" I smile, and as we're walking back to the Porsche, I whisper to Steve: "He knows, huh?"

Steve looks at me smiling a big smile, and in an exaggerated way, nods his head, up and down. Up and down, yes... "Let's go get lunch, Loni, I'm starved!"

And now I realize, I realize that the butterflies in my stomach I had just a few moments ago, being 'exposed' so to speak, by Bill, I'm ok with it! I'm not at a loss for words, I'm feeling good, exhilarated by the flight we just had, and the realization that Steve is not only giving me a 'hall pass' tonight, but he set it all up! "I'm hungry, too Daddy..." said with a big smile, "And Steve?"

"Yes, Loni?"

"Tonight, I am going to make Bill wish he was you..." I'm still smiling... "I'm going to curl his toes in a nasty way! He'll need pliers to uncurl them!" I burst out laughing...

Steve laughs, puts two hands on my face, leans in close: "You are a nasty little slut, aren't you? Maybe you will surprise me, shock me tonight?" We're both giggling, a quick kiss, and get in the car.

"Let's go to the brew pub. It's not far, not the best food on the island, but it's good pub food with a Big Island twist, and good beer, too!"

"Fly on, captain" I say, pointing forward with my hand.

We get there in just a few minutes, it was very close to the airport. Cool place, lots of great branding and graphics, neat signage painted onto surfboards, the Hawaiian look. We get seated, at a tall bistro table for two, and share one menu, looking at it close together, I like it that Steve eats pretty healthy, we agree to split Ahi and hummus plates, but then we break down, and also order a small pesto pizza, too, figuring we would split it... And we order one of those beer samplers, you know, they give you short pours of different beers, in little carafes.

While we wait for our drinks and food, we actually talk more about our professional interests, going back to a conversation from yesterday, we chat about the financial world, and I give some more details to Steve about some of the companies in the biotech area that I think are going places... I like it, I like it that we can talk like this, that is doesn't have to always be about sex, about making love... I like it that he listens to my opinions about things I know, in my own professional world...

But I can't resist, I lean over to him, put my lips up to Steve's ear, and whisper to him: "I really liked sucking on your cock this morning!"

I guess that interrupted our business chat, Steve pulls his head back a bit, a slight smile, and whispers back, "My sweet sissy, that was entirely my pleasure..."

The meal was good, we ordered a bit more than we could finish, but leave the leftovers, there's not enough to take home... "Let's head back," my Daddy tells me, "I think I could lay out in the sun for a while, catch the last of the afternoon sun, ok?"

I nod, yes, and before you know it, we are there, out on Steve's patio. He has some board shorts on, thankfully not too long, I really don't get into men wearing shorts at or below their knees. "Why would they want to, when these hunky guys could be showing off some thigh muscle?" I giggle to myself... I just have on that little pink zebra Berrydog micro string bikini that Steve's already seen, and the same gold-strapped sandals I wore today. No breast forms, I've taken them off. In this little bitty bikini, "this is a real 'sissy boi' look," I think to myself...

We spend a nice hour or so on the patio. The sun is still nice and warm, even as it starts to move downward in the west sky. As has been our practice these first days at Steve's, we are laying together on the oversize Chaise lounge. A good mix of chat, a few kisses here and there, and some good, albeit vanilla conversation, things about the world, the way we view current events, favorite foods, wine and other drinks, favorite movies. I laugh at some of Steve's favorite movies, what a 'guy' he is, he likes war and action movies. But then he impresses me, and lists a few classics from the thirties, forties, and fifties: drama, detective stuff, Hitchcock. We find one set in common that we both love, those old 'Thin Man' movies, in black and white, based on the novels from mystery writer Dashiell Hammett. The stars of the movies are a dashing couple, Nick and Nora Charles, played by William Powell (dashing) and Myrna Loy (beautiful). In these movies, they solve a series of mysteries, seemingly never dropping their cocktail glasses out of their hands while they make cheeky comments to each other and nearly everyone they meet as they ultimately, near the end of each movie, solve the crime at hand. What a wonderful thing to aspire to, to be as good-looking, charming, and witty as those two... I sigh to myself. I wonder if when we are out in public, people look at us as an attractive couple?

Then, the conversation turns to tonight, the card game. After talking more about it, I'm a mixture of antsy, nervous, flirty, and horny. Even though I sucked Steve to completion this morning, the thought of playing with three cocks I've never seen before puts a little something in me, that I can feel all the way down to my clittie. I'm planning to take three different men 'to the sixth floor', as I've described before. This makes me shiver, even with the warmth of the afternoon sun on me.

Steve gets up from the lounger, I raise my head to look up at him, looking at me he says, "I'll be right back..."

Curiously, I see him head down the stairs, to the first level, not up, to his bedroom. I'm trying to think about what he's up to, is he going into my room? The garage? Somewhere else? He comes back fairly quickly, just a couple of minutes later, holding a couple of folded up towels in his hands, and a bottle of suntan lotion.

"I think you need this, Loni, I'm seeing you get a little pink on your back and chest... Roll over, lay on your stomach, I'll be more than happy to put some of this on you. Complying, I roll onto my tummy, and Steve undoes the tie of my halter top, undoing the tie behind my neck, and then, on the bikini bottom, he unties the two ties, one on each side of my hips.

My backside is naked, totally bare, exposed to my lover... except for the sandals on my feet, and the day collar on my neck. My face turned sideways on a towel, and elbows bent and hands under my head, I have my eyes closed but hear the squishy sound of the lotion being squirted out of the plastic container. Soon enough, I feel Steve applying lotion to the small of my back. Minute by minute, Steve spreads the lotion all over my upper back and arms. Then, squirting more lotion out into his hands, he moves from the small of my back, to my two butt cheeks, to the back of my thighs and calves.

"My word, Loni, you just keep your skin in perfect shape. I don't see a blemish or imperfection, nearly anywhere... So tan, so smooth", he's talking to me in a soft, but assuring tone. Your just look delicious, totally yummy!" He leans down and plants a single soft kiss on my ass cheek...

More lotion, more lotion now, on my cheeks, before you know it, he's at my rosebud with one finger.

I moan: "Oh Daddy, it's so good, this feels so good..."