Sissy Loni on the Big Island Ch. 02

Story Info
After accepting his invite, Loni flies to the Big Island.
5k words
4.3
5.9k
10
0

Part 2 of the 7 part series

Updated 06/10/2023
Created 11/16/2020
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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

There was a lot of background and character development in chapter one, it will help a lot if you have not read that first chapter, to go back and go through it!

In Chapter one, we learned about Sissy Loni, and what she's gone through, from college, to grad school, then to being on her own and developing into a cock worshipping sissy slut. I know parts of that were dry, thank you to those who got through it all and still want to move on to this chapter. Things get warmer and warmer, chapter by chapter...

At the end of chapter one, Loni meets Steve online, gets to know him over the course of almost a year, and then finally accepts his offer, for her to visit him and stay for a week, on the Big Island of Hawaii...

.

.

.

After months, literally three months of invitations, I finally break down and agree to fly to Hawaii and visit my online boyfriend, Steve. He is a big, handsome guy, and we have shared a lot of online camming, and have cum together, explosively, many times. In my heart, I feel like we have more going on than just rubbing one out together, we have developed a pretty good friendship, have stayed online many times after the sex was over, and just chatted, just chatting about anything. Sometimes, we start off in that mode, too, we'll have a chat, each of us with a glass of wine, and have a conversation, that gradually gets more and more randy, until Steve pulls out and starts stroking his long, thick cock, knowing full well I enjoy the show that he puts on for me, as much, I think as he enjoys the show I put on for him... We've gotten to know about each other's interests and kinks!

We arrange the travel dates, and true to his word, Steve books me a first-class ticket to Kona International Airport, or KOA as I refer to it, in airport jargon. I like to fly Delta when I can, and this means from San Francisco, I'm going to have to start with a short flight to LAX, and then on from there to Hawaii. We book a Tuesday depart and the next Tuesday will be the return home. That will give us six full days together. I hope that's not too much, will I get tired of him - or he of me? I look at what I have on my work calendar, and only having two projects I am taking care of for work right now, I will be able to finish both off before the trip, and then I won't take on anything else, until I get back home. A good situation, I don't like the idea of having to do phone or video conferences while I'm with Steve...

Four weeks away, I start thinking about the trip and taking clothes out of the closet and from my dresser and start laying things out on the guest bed in the office. It gives me an idea of what I will be able to take, I hope to wear at least a couple of different things each day for Steve, I'm thinking I am going to need two full suitcases! Fortunately, with that first-class ticket, I can check as many bags as I want, up to three.

So lets see, this is June, I check the weather for Hawaii and it looks like mid-80s during the day, and around 70 into the evening. Maybe cooler if we're right on the water? I go through my closet first, hmmm what's my best stuff, my sexiest stuff? I pull out my three favorite cocktail dresses, a couple of short skirts, some blouses, I have a couple of nice sexy corsets and shapers in there, too! That makes one small pile. I go to the dresser, almost emptying it, I smile to myself. Stacks of panties, thongs, teddies, crotchless things, several teddies, lacey camis, all sorts of stockings, garter belt sets. Uh oh, I'm going to need shoes, too! Looking back in the closet, I'm not quite a shoe diva yet, but I think I have maybe twenty different pairs of women's footwear, ranging from fetish-style knee high patent leather lace up boots, with four-inch heels, down to a pair of pink New Balance running shoes. I pick out a nice assortment.

I look over my swimsuits, "how is it that I only have two," I giggle to myself? I take a break, go to my computer, and browse Ujena, Berrydog, and Venus. I try Nordstrom Rack, too. I'm not opposed to getting a good bargain when I can! I find a couple of hot items, and order them, I have plenty of time to have them shipped and get here weeks before I leave. Then, thinking about being in Hawaii, I also shop for a couple of sexy flip flops, a couple of scandalously short shorts, and a couple of print spaghetti strap tees. What about a couple of erotic costumes? I know I'm going to take my sissy maid outfit, I shop more on the computer, and find an incredibly sexy sequined bunny costume, and how is it, that I've never owned one, but I choose a 'sexy schoolgirl' set, too.

Over the next few days, I order a few more miscellaneous things, and try to lose myself in work, working conscientiously to finish my two consulting projects, and filling my free time with lots of running, as well. Also, I've been thinking about Steve's eight-inch war club and I start doing extra anal training, with one of my largest dildoes. My feeling right now, is that I want him inside of me as much as he'll want to fuck me, I want the experience to be pleasant for both of us. I've never been able to bring myself to a 'sissygasm', when you ejaculate just from prostate stimulation, but with my biggest dildo, I'm starting to feel something really, really good! I think I'm close.

Now, the trip is two weeks away, and everything I've ordered has arrived. Steve and I meet online, fourteen days ahead of my flight. We have a glass of wine, chat about the visit, and then spend nearly an hour talking dirty talk and watching each other edge, until we both get very close, and blow our loads within a few seconds of each other. Then, as we discussed previously, we pledge that this will be the last time either of us does that, until we're face to face, at Steve's house... Fourteen days from now. Speaking for myself, I'll be like a dog in heat at that point! We also agree, for the duration, no more video chats, but we can text or email each other.

These last two weeks seem to drag on, taking forever, seemingly, to pass. I'm running an hour or more every day, been trying to cut down on my calories, too, I manage to drop a couple of pounds. My clothes are going to fit great; I haven't gained a single pound since I first started purchasing my sissy outfits, more than a few years ago.

I look through all my makeup - I think I need to restock a few things. I'm not embarrassed to do it, in my khakis, a Lauren polo shirt, and loafers, (not en femme) I go to Walmart, and pick up some concealer, blush, lipstick, and a new set of makeup brushes. Oh yes, and a couple of bottles of nail polish. Fire engine red, and neon, Barbie pink.

Finally, it's the day before, all I can think about, every minute, is the trip. I'm super-horny, and jittery, too: I am nervous as heck! We've arranged, via email, when I get there, I want to have my own car. I have one reserved with Avis. I'm going to drive to Steve's getting there late afternoon. By his choice, he will NOT be there, I already have the passcode to the gate securing his development, and to his garage door keypad. I will let myself in, and I'll have an hour or more to get ready for him. This allows me to travel as my regular guy self, but then get into Steve's house and get ready, he'll never see me as a guy, I love it! Like never before, I'm going to get to spend just about a whole week, twenty-four hours a day, in gurl mode.

I wake up, pre-dawn, needing to get going early to get to the airport on time. Even considering the time zone difference, with the two hours I'll gain flying west, I still need to leave quite early to arrive in Hawaii before dark. It's a fairly long flight from L.A., over five hours, I think. So I get ready as I would for any usual business trip, a quick shower and shave, and I put on my 'guy uniform': summer weight slacks, sandals, and a silk print Hawaiian-style button down shirt. All guy, except for the pink lace panties I am wearing under those slacks! I wear the slacks because I really don't want to wear shorts and have people looking at my silky-smooth, tanned legs in the airport or on the jet! I have two full-size suitcases filled with my sissy gear for the week, a small soft bag with miscellaneous things I will carry on, along with my laptop backpack.

The Uber driver arrives right on time and we make good time to SFO. Check in goes smoothly, and I am loving seeing my two suitcases disappear down the conveyor belt behind the check in counter. I smile. I think to myself, "there is a lot of fun and hot times packed into those two babies!" At the gate now, do they EVER board when they say they will? I think when you see the boarding time on your pass, just go ahead and automatically add on another fifteen or twenty minutes. Finally, we get on, it's an early flight, so we're going to get breakfast in first class. A cute little flight attendant welcomes me, and asks if I want something to drink? I LOVE her look, study her makeup... Coffee maybe? You know, I'm on vacation now, I ask for a Bloody Mary, instead. As you need to, I sip it all down before the main door closes and the captain starts to fire up the jet engines.

A routine flight, a nice sunny day in California, I have the window seat and I can see a lot of coastline as we travel down to LAX. It doesn't take long. I manage to eat the scrambled eggs and sausage and a small yogurt, and the tray is taken away and we're already on our descent into southern California. A nice, smooth, and quick flight! The layover is short, just enough time to get to the gate and look through my emails on my handheld. Not much there, a one-liner from Steve: "Thinking of you XXOO. - S." I hope so!

Now I'm board for the long leg of the trip, this is going to be five hours twenty minutes of flight time, I'm told by the attendant. Another good looking attendant, she looks really good in her uniform; I wonder to myself what's she wearing underneath that company uniform? I settle in, we're up in the air, headed west to Hawaii! Just thinking about it, I take a deep breath. I'm nervous about this, I hope it all goes ok! Opening my laptop, I answer a few emails, including Steve, watch a movie, lunch is served, I get a glass of Chardonnay to go with it... I try to take a nap, a little 'beauty sleep' I giggle in my head to myself, and, fortunately, I am able to nod off for an hour. I hear the chime from the cockpit, that 'ding' that informs the cabin crew that the long descent into KOA has started. All in all, this leg of the trip went just fine. Not much more after that, the jet hits the tarmac, a bounce or two, but before you know it, we are stopped at the gate and after a quick announcement, the door opens and we deplane.

The layout of the KOA airport is a little different, there are a lot of shelters, but largely, because of the mostly great weather in Hawaii, it's actually mostly an outdoor airport. The desks at the gate are under cover, but when you walk from gate to gate, you are outside. Carrying my small bags, I head to baggage claim and quickly find my two suitcases. I can just manage, I wheel the two of them toward the rental car shuttle, with my small bags strapped to the suitcase handles, I'm fine. I get on the shuttle, and five minutes later, I'm there, at the rental car location. Another deep exhale! It won't be too long now...

The pickup is easy. I find my name on a little board outside the small guest reception building and see my last name and the space number where my car is waiting. Very nice, it's a brand-new Jeep Wrangler, you know, the kind that has the removable hard top. Maybe we'll get a chance to use that this week, take the top off and go for a drive around the island? Or maybe not, maybe we'll just stay at Steve's so I can focus my full attention on his fat, juicy cock! Another giggle that only makes a sound inside my head. The bags are loaded, I hop in and fire up the Jeep, I'm headed to Steve's. Should be only about ten minutes, or so, I head north on Highway 19, I have the address, have the directions, he has mentioned that he lives very near to the Hulalai golf resort, which I have read about. Very nice, this is very nice area!

'Maps' gets me right to his gated community. It was indeed only ten minutes. I punch in the code, and the gate swings open, another two minutes, and I find Steve's driveway. Looks pretty modest from the front, a two-car garage faces the street and some windows up high on the first floor, and then more windows on the second floor. I recall from Steve's web cam tour, that the house has three levels, sort of staggered into the slope of the hillside his neighborhood is built into. I park the car on the right side of the driveway as Steve has instructed me, because he will want to drive into the garage when he gets home. I walk out to the find the keypad and enter the code. Hmmm, 6969 - he said he chose that code for me, that's my special code. A little sexual innuendo, I guess... I smile. The door opens.

Very nice, parked inside the garage, in the right hand spot, is a Porsche 911. Wow, very nice, it's beautiful, jet black, a convertible. Maybe he'll take me out in that? Double wow.

Ok, enough gawking. The garage is very neatly organized, I can see, looking around. A little workbench in the back. I get my luggage out and roll the bags inside. There's a note on the inside door, the entryway to the house: "Welcome, Loni! Please use the guest suite on the lower level, this is your private space for the week. If you arrive on schedule, you will have 90 minutes or more to get ready. I had a 1:00 tee time and then I'm going to the wine shop to pick up a few things. Be back here around 6:00. XXOO - S."

Ok, I breathe a sigh of relief. Ninety minutes to get ready is good, I will not have to rush. I take my bags down a half flight of stairs. Another wow: the entire lower level IS the guest suite. The entire west wall of the area is glass, from floor to ceiling. As you enter, there's a generous living room with a kitchenette area on the back, east wall, a queen sized bed in the bedroom, and a VERY large bathroom, with shower, two-person jetted tub, and vanity with two sinks. There's a modest veranda, too, stone tiled floor, with some outdoor lounge furniture: two Chaise lounges, and chairs around a glass table with a bright blue umbrella. Very nice. Two people could live here, it's just like a small apartment.

Before I start to get ready, I just take a quick look around the other two levels. The mid- or main level is much larger than the lower level. It's an open floor plan, with a beautiful living room connected to a kitchen. A large island separates the kitchen from the rest of the space. In the living area, there's a wide screen viewing area, a green felted card table, a pool table, and an area for darts. How manly, I think...

Back to the kitchen island, there's a range built into it, so as you cook, you would be facing your guests, I suppose. The appliances are all premium brands, all sparkling clean stainless steel. Lots of cabinets. Again, the west side of this space is all windows. I see now, there's a retractable motorized shade than can be lowered down. There's some tint to the windows, as well, to keep the heat from the afternoon sun at bay. It doesn't feel warm at all, the AC is on, I guess. I slide open the glass door to the veranda - in a word, spectacular! This is where Steve's disappearing edge pool is. Pretty good size, too, I think to myself. The area is big enough to host perhaps twenty or so people comfortably. Lots of nice outdoor furniture, lounges, a double-wide Chaise for two people to sit side by side, and several tables, again with those same blue umbrellas as downstairs.

Then I pop up quickly to the third level. It's Steve's bedroom suite. A small dressing room first, then a bedroom, and his bathroom off the bedroom. There's a second bedroom up there as well, with a desk and a computer station set up. I'm guessing this is home office. Anyway, I don't want to spend a lot of time snooping around, I do see one thing in the bedroom, a bit unusual, very interesting: it's a cast bronze statue of a naked man. Feet spread shoulder with arms folded. The figure is sporting a large cock, half erect, pointing out, away from him. Hmmm, kind of looks like Steve, I think to myself.

"Ok, ok - get going!" I say to myself, out loud. Enough of the snooping. Back to my space.

First things first. I open my suitcases, splaying them open on the bed. I unpack everything, so the suitcases are empty. I hang up a half-dozen things, and then organizing all my other stuff into the empty dresser. I arrange, neatly, about six pairs of shoes and sandals on the floor in the closet. Then my ditty bag, my soaps, shampoos, and lotions - this I put on the sink in the bathroom. Ok, the last thing, my makeup case. For right now, I leave this on top of the dresser. Sometimes, I would do my makeup in the bathroom, but there's a nice big mirror above the dresser, and the lighting in the bedroom is pretty good, so this looks fine.

Now, everything is organized, I put the empty suitcases in the back of the spacious closet. I look around the suite again, realizing how roomy it really is. I look at the bed, wondering will we sleep together - down here, in Steve's bed upstairs - will we sleep separately? Oh well, one step at a time... Now I need to get ready, and I have a picture, in my mind's eye, of how I want to look, when Steve sees me for the very first time, in person.

I don't think I have time to do anything fun, like a bubble bath, so I figure I will take a nice warm shower. First, I realize, I'm going to need to be clean inside and out, so I go back to the dresser and retrieve the hang-up enema bag that I brought with me. I gurl's gotta do what a gurl needs to do! I've done this enough, I know probably, one cleansing won't be enough, and I am right. Filling the bag with warm, soapy water, I wait to get those nasty cramps, and expel the water into the toilet. Again, one more bag, and I'm clean and ready to go. I think that will do for now. I fire up the shower, it's very nice, it has multiple shower heads, one fixed, coming out from the wall, a second, hung up on a fixture, with long hose, and the third, coming from the ceiling of the tiled shower space, it's one of those large, round heads, maybe about as big as a dinner plate, producing a rainfall effect. The shower is big, and you walk in around a wall, so there's no need for a door. Nothing will splash out of the shower into the rest of the bathroom. I also notice, it's plenty big, at least for two people...

I soap up everything, twice. The soap I brought with me smells so, SO good - hints of lavender and lemon. I feel really clean and take my razor and run it down my legs, I KNOW they are already smooth, but the habit is hard to break. I feel down around my clittie and ball sac, it is super smooth there, too. I'll check the rest of me after I dry off. The towels set out for me, by the way, are worthy of a fancy resort. Big, plush, snowy white towels. The bath towel is so big, it can fit around my waist twice! I'm starting to feel sexy...

Moving over to the sink, I look, closeup, at my face. The electrolysis is really working quite well, I think to myself. I think my beard has thinned out to 10% of the hair I had on my face only a year ago. But the long flight has left me with a bit of light stubble. So, I shave, twice. Making sure I am completely smooth-faced, I know this will make my makeup go on much, much better! Lastly, my shea butter body lotion, all over, a nice thick layer, I work it into my skin, everywhere. Up and down my silky-smooth, long legs, onto my smooth, round butt cheeks, into the crack, my chest, back and arms. The smell combines with the lavender-lemon soap aroma to produce a heavenly fruity smell. I look down, my clittie is hard, and leaking... I can't believe we agreed to abstain for the past fourteen days!

12