Sissy Loni on the Big Island Ch. 07

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Loni’s Thursday winds up with guys wanting to play Poke-her!
18.8k words
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Part 7 of the 7 part series

Updated 06/10/2023
Created 11/16/2020
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Sissy Loni on the Big Island Ch. 07

Thank you to everyone who has been reading along, thank you for your comments, please remember to rate the chapters when you are finished! If you haven't read any of the earlier parts yet, I recommend you go back if you have time... Chapters one and two are slower, mainly scene setting and character development, the 'real' action, guy on gurl, starts in Chapter 3. So, if you're looking for that kind of action, start there, with Chapter 3! Also, another note: when clothes items are specified with the manufacturer and/or item name, the purpose is to give you a chance to do an internet search to see exactly what different outfits Loni is wearing...

Recapping Chapter Six, Loni and Steve capped off a huge Wednesday with explosive lovemaking right before sleep, as they started the day off as well. During the day, they sandwiched sightseeing, lunch, and dinner around a trip to a private, isolated bluff, where Loni was forced to strip, and spend more than an hour naked, on her knees, worshipping Steve's cock and confessing to him her sissy psyche and most secret sissy desires. After going out to dinner, they made sweet, explosive love on Steve's bed, Loni sitting on top of Steve in the Lotus position. They finish, cumming together, as Loni experiences her first anally-stimulated orgasm ever! Finally, they curl up together and fall asleep, spooned together, just before midnight...

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THURSDAY:

Just like yesterday, I woke up well before Steve, I'm still on Pacific time zone, I think to myself... I sneak out of bed, making sure to not disturb my sleeping lover. I tiptoe downstairs and make coffee. A little easier, I'm starting to learn where things are kept in the kitchen cabinets and drawers. Not in a rush, I'll stay here in the kitchen to wait for the coffee to be ready. I sit on a stool by the picture windows, look out to the west, still dark, I see the moon, nearly full, setting in the west, sliding below the horizon, and the lights of the homes below me, scattered across the hills, down to the dark ocean.

Even though it's early, and I'm still a bit groggy, one thought after another is flying through my mind! Seems like Steve and I have been traveling eighty miles an hour since I arrive at his house Tuesday evening... Our first sex together, my clittie squirted onto his bedspread, that was partially caused by having his big cock inside me, but honestly, I smiled, I was rubbing my little clittie against the silky material underneath me, that helped a lot. But last night, phew, it was pretty much him, his cock inside me, pressed against, and rubbing back and forth against my P-spot, I have to think that was one of the most exciting, biggest and best orgasms, and certainly the most fantastic ejaculation that I have ever had in my whole life! Mmmm, and maybe my bum is still more than a bit sore... But what a wonderful way to get sore, I think to myself, smiling... And the beauty of the Big Island, the day collar, and that trip out to Steve's 'secret bluff'... Naked, on my knees in front of him, I worshipped that big cock of his for perhaps an hour, and spilled my innermost secrets, about my sissy feelings and desires, as if I was drugged... And still, after that session, I still just want to be in his arms, or be kissing him, or better still, have my mouth on his magnificent cock. Or in my ass... And tonight, is he really bringing three friends over for cards, or is this a bluff, is he punking me?

After a few minutes, I hear the coffeemaker gurgle, the last few drops are emptying into the pot. I get up, pull a big mug from the cabinet, and fill it, nearly to the top, with that wonderful-smelling brew. "My morning fix," I smille to myself! Gathering up my things, I pad down the steps to my suite, toss my nightie and slippers on the bed, and step into the bathroom. There's still a bit of mascara from last night that needs removal, my forms are still glued to my chest, so I attend to both, and step into the shower. The warm water feels good, as it runs down my tanned body, I soap up today with lilac-scented body wash. Soon, I'm covered with suds, all of my body, and run my razor over a few spots where I felt a little soft stubble. My clittie and balls, become especially smooth, with neither hairs nor stubble to be found. Just like smooth silk, I feel them, all soaped up, mmmm, so nice...

I really think I'm too sore, 'back there', after last night, to do anything like that again this morning. "Hopefully, Steve will be ok with a morning BJ," I think to myself. After the soaped-up shower scrunchie visits every spot on my body, I get all the suds all washed off, and step out into one of Steve's plush towels, mmm, a simple pleasure that still feels so good! I get dried off, put a little makeup on, and check myself in the mirror, adjusting my wig. Maybe I'll go without the forms this morning, Steve was fine with that yesterday afternoon on the patio... I slip into my Jonquil Samantha Leopard print satin chemise, I recall this was part of a large mail order I did a few weeks ago, at Nordstrom. It feels so nice against me, making my clittie nice and erect, I decide to go without panties... Slippers now on, one last check in the mirror, I head upstairs with my coffee. I see the world is starting to wake up, its starting to get light, I refill my mug, and fill a second one, for Steve.

Stepping carefully up to the Steve's suite, I try to be as quiet as possible, but turns out, didn't matter, he is already awake, sitting up, checking his email or the weather, or whatever, on his handheld. He looks at me and the coffee mugs, and smiles, as he sets the phone down on the night table. "Thank you, my sweet sissy... I slept really well, did you?" and without waiting for an answer, he's eager to continue: "That was really wonderful last night, it was so wonderfully erotic, and intimate, loving, and powerfully explosive, all at the same time, is that possible? I wasn't too rough at the end, was I?"

I walk over, and placing the two mugs down, I lean over, put a short, sweet kiss on his lips, and looking into his eyes, say just a few words: "Yes, lover. It was so, SO nice, maybe the nicest sexual experience I've ever had in my life. And no, not too rough..." and I tease him: "You fucked my nice and hard, like a Daddy is supposed to do to his sissy!" And then I giggle, continuing: "Although the rest of what has happened here, the last thirty-six or so hours, there are a few other sexy sessions we've already shared, that are in my lifetime top ten now, too."

Steve chuckles, patting the bed next to him, for me to sit down next to him. Gladly, I pull the covers back a little, and slide my legs under them, and then wiggle myself into place, next to him. "We need to remember that, or write that down, how you got us into that position, it was as if your cock was vibrating inside me, flicking at my P-spot." Continuing: "You know, Daddy, that was the first time I've EVER cum entirely from just anal stimulation!" I finish, sighing a wonderful, dreamy sigh.

Then, I reach a hand under the covers to Steve's groin. He's rock hard, again, heavy in my hand... "Do you wake up like this EVERY morning?" I ask, with a sly smile on my face...

"Well, honestly, YES!" is his answer, "But it makes it a certainly that I'll be hard when you are here right next to me. I'm blaming you...", chuckling, "if I had you around every morning, and was waking up with you next to me in bed, I don't know how I could NOT wake up with an erection!"

I smile, our faces are now just a few inches apart, and now I have two hands on his meaty cock. Just gently foreplay, I'm stroking him slowly, loving on my Daddy's hard penis. "I don't think I can have you inside me this morning, I'm thinking I'm a bit sore, can my boi-pussy have some time off, for good behavior?" I ask, with a giggle...

Steve smiles, and nods: "I totally understand... Come right here, sit up next to me, Loni. Grab your coffee, I'd like to go through my plans for today with you, so you know what's on our agenda..."

So there we are, pretty conventional looking couple, all things considered, sitting up against the headboard, a couple of stacked pillows behind each of us, holding our coffee mugs with two hands... "Not exactly June and Ward Cleaver," I think to myself, slipping one hand under the cover to touch my clittie, something June Cleaver never got to do!

Steve starts: "After we get out of bed this morning, I'd like to get a little breakfast, something simple, just something light... Then, if it's ok with you, I need an hour or two of 'me' time, I need to check on a few investments online, and return a couple of emails that came in last night" he says, pointing at his handheld. And I need run down to the golf shop, there are a couple of things I need to pick up, that I purchased for you... "

"Well, Daddy, you already have shown me your 'big stick with a stiff shaft'", I giggle at my bad golf joke... "But absolutely, on the 'me time', Daddy! I haven't opened my laptop for thirty-six hours, and I need to go through my emails, too... Maybe I'll do some online shopping, too, or see what kind of clothing or jewelry stores are out here that I wouldn't get a chance to shop at on the mainland!" I pop a big sissy smile on my facing, thinking that's a smart idea... A sissy can never have too much bling!

"Good, well see what you can find, we can do an online purchase, and pick stuff up, or go in and browse for a bit, too, when we have time, today or another day, too. Now, we need to be at the Kona airfield by eleven, a friend of mine from the club is going to take us for a flight around the island, maybe it will be an hour, or a bit more. He's got a nice little Cirrus 22T four-seater, he's taken me to Oahu a few times when I've needed to shoot over for some business and also for golf trips. After that, we'll grab a bite to eat somewhere, and head back here to catch some rays out on the patio for an hour or two. So far so good?"

I'm just listening, a captive audience. I nod, yes.

"Then, after we lay out on the patio, we can grab a shower, and rendezvous in the kitchen. If we have time, I've got a couple of filets in the fridge, we can have them with some grill-roasted veggies and a nice cabernet..."

Ok, good, I'm still with him, nodding yes, again...

"And then we'll get ready for the card game. The guys will be here at seven-thirty, they are usually pretty punctual." Then Steve pauses... "And..." another pause... "I'd like you to dress up special for these guys, ok? I want you to get so 'eye candied-up', that they'll have a hard time concentrating on their cards!" he finishes, with a big smile. "We don't play for a lot of money, but regardless, I HATE to lose to these guys, same as on the golf course..." Maybe you can show them a few different looks, different outfits while they're here?"

"Daddy, did you really mean what you've been telling me? Are you expecting me to get intimate with these guys, whom I've never met before in my life? Daddy, are you yanking my chain" and I giggle a little, thinking about the double entendre, and I touch my day collar and looking at Steve I say, "I guess I've been collared, but there's no chain to yank, yet?" And I wink, with just a faint smile on my face.

"No, Loni, I have NOT been misleading you. It's going to be just as I've said, but let me clarify: In the time we've known each other, and I know it's been online, mostly for phone and cam sex, you've made it no secret to me that you're a sissy slut, a cock slut... You've told me, you enjoy... you LOVE sucking cock, you love pleasing men, you love swallowing cum, you love getting fucked in the ass... Am I missing something?"

Now Steve, is looking at me with a very serious look on his face... looking back, into his eyes, I look down, embarrassed, humiliated maybe, and then looking back up, without a word, realizing he is correct, I just nod: YES.

"Now, what I'm expecting will happen, what I want from you, is to be the eye candy for my buddies tonight. Wait on us, make us drinks, serve some snacks... be attentive... laugh at our jokes... And... We will figure it out as we go, play it by ear. Maybe take each of them downstairs and give each of them a nice blow job, or go behind the pool table, get on your knees and let them walk up to you for blow jobs. Let your hair down, have fun. You didn't fly out here to be cautious, did you? And you know..." Steve adds, with a caring look on his face, "Whether you're asked to give us all blow jobs, or bend over and present your boi-pussy to us, I will be there, making sure that nothing crazy happens, nothing that could hurt you..."

Then, he smiles at me, and touching the very front of my collar, "You are mine, no one else's, while you're here this week. But part of that, is if I want to share my pet with someone else, I will do it! These guys are clean, will be very respectful... mostly..." he continues, with a chuckle. "But they know how to let their hair down and have a good time when they are sure nothing will ever get back to their wives. "I want to make sure all of your sissy fantasies, your sissy desires get fulfilled this week! I think tonight will turn out to be something exciting, something hot, that you'll remember for a long, long time! Then, when the card game is over, usually they stay two or three hours, they will go home. We will go upstairs, and cuddle out on the patio, under the stars, have a nightcap, and snuggle up in bed for the night. Okay?"

I'm thinking about this, I think I can have fun tonight with Steve and his guests: "Steve, it sounds good now, when you put it like that... I'll be in the mood to have a good time with you and your friends and show them a 'special time'." I smile and wink at him. "I have a good idea for some different outfits to show off in. I think all four of you will like me in them..."

"Good. And then tomorrow, and into the weekend, if it's okay with you, it will probably mostly be just you and me..."

He says that one sentence, I like it, and lean over and kiss him gently on the cheek.

Then, Steve lifts up the covers again, and flips them off of us, we're both exposed. Me, in my short robe, Steve, au natural. He spreads his legs apart, his cock is still hard, nearly vertical, pointing to the ceiling. There's a faint hint of a throb in it, too, if you look carefully.

I'm spellbound, staring, focused directly, focused only on Steve's meat. After staring at it from close range at the bluff yesterday, it's effect on me now is like when a hypnotist dangles a swinging pocket watch or crystal pendant on a chain... Without looking away, Steve asks: "Loni, what would you like to do right now? Should we go downstairs, to get more coffee? Should be start breakfast?"

He's teasing me. He knows what I want to do... I'm silent, five seconds, ten seconds, fifteen seconds, just starting at what might be the most beautiful cock I've ever laid eyes on, it's throbbing, lust slightly, with his pulse...

"Loni?" Steve asks...

I turn my head back, away from Steve's cock, and look into his eyes. "Daddy, I want to suck on your cock. I want to give you a blow job, a nice, long, sensual blow job. Then, near the end, I want you to shoot your cum into my sissy mouth, and then I want to swallow it all. I want to know, all day long today, that your semen is inside of me... You're making it very hard on me..." I say smiling, looking back down to his cock... "to not want your gorgeous cock in my mouth."

"Very good, Loni, good. Scoot down, get down there, between my thighs, I want to watch you, I want you looking up at me..."

Obediently, I move down toward the foot of the bed, between his legs, I lay down on my left side, my head rests on the inside of Steve's right thigh. His cock, now inches from me, disappears into my mouth. Our eyes are locked.

For the next twenty minutes, the only thing on my mind is what I can do to make this man's cock feel good, what I can do to make him feel good. I'm in sissy heaven, sissy subspace... Mostly, I'm switching back and forth between sucking, licking, and kissing his cock. I also change things up a few times, and move my mouth onto his balls, and roll those dreamy orbs around in my mouth. I kiss the sac and squish my tongue all around them. Just barely aware of what I'm doing, I think to myself, these things are about as big as golf balls!

As all this is happening, I'm not breaking my eye contact with Steve. I see him open his mouth to try to say something to me, and then he just moans a bit, softly, and tilts his head back. "Oh baby... Oh baby..." he whispers.

And then, like yesterday, after a long period of letting me exert most of the effort, after fifteen or twenty minutes, I can tell Steve is getting close to the end of this bit of intimacy. He starts lifting his pelvis up, to thrust his cock deeper into my mouth, as I am, at the same time, working my mouth down to the bottom of his shaft. His biggest thrusts, when he is in me the deepest, the head of his cock is at the entryway to my throat. I'm working hard to suppress my gag reflex! More thrusting, more vigorous thrusting, I've not said a single word since I worked my way between his thighs... Steve starts vocalizing his pleasure, the pleasure I am giving him...

"Uhh... Uhh.. Uhh... Mmm... Mmm.. Mmm..." At least five minutes more of this, he's thrusting now with all his strength, pounding my mouth from underneath me... "Oh yes... Oh yes, Loni..."

He pushes my head down onto him, onto his cock. I feel him pulsing, his ball sac tightening, he's seconds away from ejaculating...

Quickly, I grab the base of his cock, the bottom four inches, with one clenched hand, and fix the other half of his cock in my mouth, I want him to cum into my mouth, not down my throat! I want to be able to catch and collect his semen in my mouth, before swallowing it... The pulses become stronger and more rapid. I've got a firm hold on the base of his cock while his hands rest on the back of my head. My lips form a tight seal around his cock as I suck his penis in a pulsatile fashion.

He starts to cum, in my mind, I'm counting the spurts as he moans: one and two are smaller but get him right up to high gear, three, four and five are gushers! My mouth is rapidly filling, in my mind I know I should be able to hold all his creamy cum in my mouth, but with having that fat cock in there, too, makes one wonder... Six... he's slowing down... one more: seven. Is he done? I'm still looking, still trying to look at Steve... He's lost eye contact, in the ecstasy of cumming, his eyes are closed, and head tilted back. A few aftershocks... I love the way his body will shiver or quiver, a few times, after the main event... Like kids setting off firecrackers after a big fireworks display!

I am happy, content... my thirty or so minutes in hypnotic subspace has given me that wonderful rush, the combination of a dopamine and endorphin rush, the neuroscientists try to explain... All I can say, is I had Steve in my mouth, I felt that churning in my core, a pleasant feeling of butterflies in my stomach, and at the same time, having a strong erection of my own During this whole time, from when I first slipped Steve into my mouth, to right now, about thirty minutes in total, my clittie has been rock hard, and I know, without checking for it, that it has been leaking precum, oozing out of the tip of my clittie, in a little stream, onto the bedsheet.

I slide my mouth off Steve's cock, now not fully hard anymore... and as they do in the sissy porn that I watch so much of, I open my mouth, to show off to Daddy how much cum I have coaxed out of him. And then, a second or two later, close my mouth, swallow, and send it all down into my tummy... I'm a happy gurl!