Sissy Loni on the Big Island Ch. 04

May 2, 2024 // By:analsex // No Comment

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Thank you all who have been following my new story! In the first three chapters, we were introduced to Sissy Loni, a thirty-ish sissy slut living in the Bay Area of Northern California. As her sissy side developed in her twenties, she met and made friends online with Steve, who lives out on the Big Island of Hawaii. In Chapter 3, after much preparation, Loni made the flight out to visit, ans will stay for a week. She finally makes it to Steve’s place, a beautiful, private, hillside home. They meet, and the evening concludes with an explosively steamy and erotically charged session on the top of Steve’s bed. Exhausted, Loni falls asleep for the evening, spooned up against Steve.

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Wednesday Morning:

Still feeling two hours ahead on Pacific Time, I woke up before dawn, Steve fast asleep, close to me. Fully awake, I decided to get up, out of his bed, to take care of a few things. I grab my robe and slippers, and just in my cami top, I tiptoe down the stairs, to the main floor. Poking around, I find where Steve keeps his coffee and coffee filters and set up the coffee maker to brew a pot. Hmm, supposedly that Kona coffee from the Big Island is supposed to be excellent. I hope, I love my morning coffee, and I love GOOD coffee!

While the coffee brews, I step down to my suite on the first floor. I look in the mirror, and think to myself, “Well, I’ve seen worse!” giggling softly to myself. My butt is a little sore from that major ass fucking Steve gave me last evening, and besides that, there’s a little soreness everywhere, but not too bad. I think to myself; this is a function of being in pretty good shape! But I need to freshen up, it would be a good idea to be looking good when Steve wakes up. In my mind, I go back to last night. Could it have gone any better? In my mind, I guess it felt romantic and raw, at the same time. He was so nice to me, but oh my God, when the lovemaking started getting physical, Steve was in charge, and just about all I could do was to go along with everything he wanted! I think we both said ‘incredible’ and ‘amazing’ ten times each after the pink smoke cleared… What a combination, he’s big, strong, handsome, well-endowed, and showed great stamina. I bet no woman ever has called him a ‘minuteman’… I’m so glad he agreed to be tested before I came out, having him inside me, flesh to flesh… umm, I gush to myself, it just feels so good, feels so good to have him shoot his load inside me, without needing a condom!

I start running some warm water in the sink, I’m going to want to douche and then grab a shower. I take a couple of minutes to remove whatever makeup on my face didn’t rub off onto Steve’s cock or the bed sheets and run back upstairs for that first cup of coffee. “Mmm, it smells good in this kitchen”, I think to myself. I fill a mug, and bring it back downstairs, still naked except for that cami.

Back in the bathroom, I douche my boi-pussy with my enema bag until I get myself nice and clean, and then run some hot water in the shower. A nice warm, soapy shower, mmm, very nice. It loosened up any stiffness I had, and continuing to sip at my coffee, I am feeing alert and ready for whatever Steve might have planned for us today. I go through my routine, body lotion, everywhere, makeup, breast forms, and secure my wig. I slip on a spaghetti-strapped, backless babydoll. It’s sheer, see-through, baby blue. I think to myself, I have a nice accessory, a matching blue ribbon, and I tie it into a pretty little bow-tie around my package. I slide into my slippers from last night, and I move up the stairs, to see if Steve is still sleeping…

Well, turns out, he is, he’s sleeping very soundly. Removing my slippers, I slide back into bed, up to my handsome host. I look at him, for a few seconds, as he breathes deep, I’ve already thought about this downstairs, how I should start his morning… I slide my hands under the covers, and reach, with both hands, for his penis. While he sleeps, he’s already thick, and partially erect. I guess he wakes up with morning wood, I smile to myself. Just holding him, with both hands, I look at him, still sleeping, I feel his erection grow, from partially erect to nearly fully hard. Then, slipping the covers off me, at an angle, I move them just enough so that one of Steve’s legs are exposed, along with his cock and balls. As I bend over, I angle his already swollen cock to my mouth. I open wide, as wide as I possibly can, and take as much of him as I can, into my warm, wet mouth. He feels so good in my mouth… Over these past few years, as I’ve started to take my sissy self from virtual porn browsing at home, to real life encounters, I’ve learned that a wonderful, blissful feeling comes over me, when I am sucking on a hard cock. I feel at peace with the world, almost in a dream-like state. In my readings, I’ve seen some submissive sissies describe this condition as being in ‘subspace’. Whether that’s where I am, or somewhere else, I like being there. I like being able to get a man hard, to make him moan, Ümraniye Yabancı Escort and to make him cum. I don’t feel any shame in it, at all. When I’m dressed up, I feel like I am a woman, and it is natural for me to be wanting a man.

He’s already hard, and now, I guess I’m waking him up. He moans, very softly. I’m sliding my mouth up and down, as slowly as I possibly can, and when I have him in my mouth, as far as I can take him, I hold it in there, while his cock is all the way in my mouth, I’m trying to massage the sensitive underside of his cock with my tongue. Then up and down again, then more tongue massage. Not rushing, I want him to enjoy this, if Steve wants me to do this for an hour, I’m going to do it!

There’s more moaning. Louder and louder, and more frequent. I rearrange myself on the bed, so I’m facing Steve, between his legs, rather than having my back to him, as I was when I bent over to first take him. I like this now, because I can look at him, look into his eyes, as I fellate him. I’ve woken him fully now; we adjust ourselves a little as my lover slides toward the headboard and sits himself up a bit on a couple of pillows. We keep full eye contact as he studies me, as I’m sliding my mouth up and down his large, thick cock, my head bobbing up and down, on my knees between his legs, ass cheeks up in the air. My baby doll has slid off my backside, my backside is exposed, bare.

Steve reaches down now, with both arms, and grabbing my upper arms, he pulls me up, slides me up to him. I’m lying on top of him. I prop myself up, with my elbows so that my face is about one foot from his. He smiles that movie star smile of his, still looking a little sleepy: “That might be the best wakeup call I’ve ever answered in my life…”

We both giggle…

I reply: “I knew when I woke up, I was going to do this. Was it okay to wake you up? You were sleeping pretty soundly…” I smile: “Do you want me to stop, do you want to go back to sleep? Maybe I should go check my email?”

Steve laughs, “No, now I can’t, I don’t want to go back to sleep. What I want, is to feel you again… To be inside you… Not your mouth… Are you ok with that? Is it too soon for you, after last night?”

And with that question from Steve, I am glad that I got up early and prepped myself. Without looking away, I nod to him, and whisper softly to him, “No, it’s not too soon. I’m ok with that…”

“I want to watch you ride me. Can you grab the lube, and a towel?”

I nod, yes. Standing up, away from him now and off the bed, I grab the lube off the nightstand, and quickly snatch a clean towel from the bathroom. Walking back to Steve, without a word, I climb back onto the bed. On my knees, I straddle him, across his thick, firm thighs. I put some lube on two of my fingers and reach back and slip it inside my boi pussy. Then a second time, and a third. Then, turning back to Steve, I squirt a handful more into the palm of my hand, and stroke his cock, applying the lube evenly, and carefully. I think we are ready. I set the lube down, on the bed, and reach over and dry my hand with the towel. Now, straightening up, on my knees, I arrange myself further up Steve’s frame, now instead of being above his thighs, my ass is directly over his erect cock. With neither of us touching it, his cock stands straight up. I can see it throbbing, mirroring Steve’s pulse.

“Help me, Daddy.” I say to Steve, looking down to my side, to where his cock is positioned.

He understands what I want, what I need, and he grabs his glistening, lubed cock with a few fingers, and holds it steady. Only then, do I begin to lower myself down onto Steve. I feel my anus press against the tip of his cock. My God, am I wishing he had a thinner cock? I remember back to last night, when at first, when inside me it was uncomfortable, to say the least, but then, after a few minutes, the pain was replaced with ecstasy. Steve continues to hold his cock steady, I press against him, lower myself down, just a bit more. I start to feel myself give, I can feel the lips of my boi-pussy start to open and accept Steve into me. After a minute or more, I feel that pop again, and I feel his round cockhead inside of me. I hold it there, squeezing it a few times with Kegels. Our eyes are locked together. He starts to moan. I smile, just a slight smile of satisfaction.

“Lift your knees up, Steve, let me rest my thighs against you.”

He immediately moves, keeping his feet flat on the mattress, he raises his knees up. There up in the air, his thighs are pressing up against me, letting me put some of my weight on him, so I don’t have to hold myself up with flexed knees. This feels good, I close my eyes for a few seconds, feeling that cockhead inside me. In this position, I have a bit of an advantage, I can control my body weight, and start to push down onto Steve’s hard cock. I start to slide down the shaft, my boi-pussy opening wider and wider. I think to myself, I’m glad I trained daily with my Ümraniye Yeni Escort fattest dildo for the past few weeks, before flying out here. I am going to be able to take him all…

I’m all the way down on him now. I put my hands down on his chest, and sit there for a bit, breathing deep and letting my ass pussy adjust and stretch to fit Steve’s eight inches. After a minute or two, it starts to feel good, Steve feels good inside of me! Mmm, I start, now, with Steve’s big body pinned underneath me, I start to raise up, and slide halfway off his cock. Then back down. Steve is squirming, in a good way, I smile a bit, looking at him, biting my lower lip.

With more intention, I start to pull up and down, slowly, rhythmically, off, and back onto his cock. Long strokes, as long as I can make them, without losing the last bit of him out of me, his round cockhead. Minute after minute, I stroke, leaning back away from him, as pull up, to try to get his meat to push against my p-spot. My clittie hardens as I stroke. We continue this, minute after minute, I accelerate slowly, but surely, riding up and down on him, faster and faster. Even though I’m on top of him, my weight is not enough to pin him down: he starts to push his pelvis up against mine, to match my downstrokes. Our bodies are making a repetitive whapping against one another, as I accelerate more, and more again. Soon, I’m riding on top of Steve, feeling like I’m riding a mechanical bull or bucking bronco. We’re pushing, thrusting against each other hard!

Steve starts grunting: “Mmm… Mmm… Mmm…”

I think he is getting close. My p-spot is getting some action, but it’s not quite the same as when Steve was on top of me last night, using his body weight to drive deep into me. I don’t care, I want my lover to squirt his load inside me.

“Do it, lover!” I scream at him…

The grunting continues, I see a touch of sweat on Steve’s brow, thrust after thrust is filling me, I am bouncing up and down in the air, my clittie flopping around uncontrollably.

Then, the bouncing changes: Steve grabs my hips and pulls me down, hard, onto him. I’m filled. He shakes, I feel him twitching, I feel that first shot of wet cum blast into me, followed by what maybe were six or seven more? He slows and stops. I’m still on top, he’s still fully inside me. I can feel him lose just a bit of that full erection he had for the past twenty minutes or so… I start rubbing his penis with my boi-pussy. I feel him twitch again, a few aftershocks.

That was so, SO good. Even without me cumming, I feel very satisfied, and very happy to have taken such good care of my host. I crawl off him, and lying next to him, I stick the towel in between my legs and press it once, into my bum. I can already feel a little of Steve’s cum dripping out, but I also know, this will continue for another ten or twenty minutes, so I am not too worried about it. We kiss. Many times. Short kisses, long kisses, with tongue, without tongue, on the lips, on each other’s face, all over, and on each other’s necks.

Phew. I pull my face away from Steve’s just a foot or so: “Good morning, Daddy!” I say in a loud, cheerful voice, giggling it out.

“Oh my God… what a way to start the day! Do you KNOW how sexy you are?” is his reply.

We both giggle, what a great way to start a day!

“Breakfast time?” I ask?

Steve nods, and we get out of bed, up on our feet, he steps up behind me and hugging me, gives a nice squeeze and a kiss on the back of my neck, very nice! Steve grabs a terry robe for himself, me in just my sheer teddy, we walk down to the kitchen. I go first down the stairs, figuring he can have a peek at my bare bum. I pour Steve a cup of coffee from the pot I made earlier, and pop my cup in the microwave to warm it up.

“I need to go grab my little robe, okay lover?”

Steve nods, I scurry down the stairs, slip my Kimono back on, and check my face. It looks okay, another dab with the towel, back you know where, as more cum is drooling out of my anus. Just a little touch of blush, I think. Mmm, and lipstick, why not, I giggle to myself.

Back upstairs now, I grab for my coffee out of the microwave, it is good coffee, indeed! I take a sip, with two hands holding my mug, I hope I look sexy to him… Just my short robe, and my heeled slippers. Steve’s already got breakfast going, looks like bagels and yogurt, looks good. I find plates and silverware, when everything is ready, we load the plates and eat our morning meal out on the patio. More nice chat, I slip off one slipper and move my foot under Steve’s robe and put my bare toes against his cock. Damn, it starts to stiffen again, “is this guy always horny?” I ask to myself.

Despite my little footsie move, not much more happens down there, close to the end of breakfast, Steve mentions, oh, I have a few welcome gifts for you, would you like me to get them? Excited, I nod, and Steve goes into the house, into his home office off the side of the living Ümraniye Masaj Salonu room and comes back with a short stack of four or five gift-wrapped boxes. I wonder to myself, did he wrap these, or have them done for him? They’re all some shades or variations of pink. Peppermint pink paper, pink foil, pink and white lace ribbons, pink metallic bows, all very feminine… “Like what Barbie’s birthday party should look like,” I think to myself…

“Here, Loni, start with this one.” He hands me a shirt-sized box. I unwrap it, it’s a dress or blouse. Pulling it out of the box, I know now, it’s a dress, but my confusion, in part, because it’s so short! A pink micro-minidress, open shoulder, strapless, I look at the label: “Lovers and Friends”, I say out loud, looking to Steve, “Would you say that applies to us, lover?”

Steve just smiles, and hands me a second box. I take it, it’s a small compact cube. Once unwrapped, I slip off the box top, and look in… gulping, I know what it is, I reach in and pull out a male chastity device. “Oh look, it matches the dress!” I giggle, it is pink, I’ve seen these many times, on the internet, never worn one, this one is branded “CB-6000S”.

Steve adds: “I chose the short-tubed one, I think that will fit you better, if we need this during the week… I decided against getting you the ‘Cell Mate’, that’s the one that your key holder can control anywhere in the world, with a smart phone. It has an electric lock that’s controlled by wireless signal.” I’m holding it up the CB-6000, rotating it, looking at the device from all different angles.

“Stevie, I think if you locked me up in this, it might make me so horny, drive me so crazy, that I’d be tempted to do ANYTHING to get unlocked…” I smile at him, giggle, and just leave it at that, letting him ponder that situation…

The third box, a thin square box, about six inches square, I unwrap this, I think it’s going to be jewelry! Lifting the lid, it’s sterling silver, a thin gauge, about like a number two pencil, but half-round, a solid metal necklace. A round, solid metal, maybe five or so inches in diameter. There’s a turquoise stone set in the front. “It’s beautiful!” I comment. Picking it up with two fingers, I now realize this is no ordinary necklace…

“It’s called a ‘Day Collar’.” Steve helps me understand. “Look in the back, the clasp is secured with this Allen wrench.” he pulls out of the box. “Should we try it on? Once it’s on, you probably won’t be able to take it off without someone else’s help”

“It’s beautiful, Steve…” I repeat. Looking at it, studying it intently, I now see there’s some engraving on the inside, flat surface. “To My Sweet Sissy Loni, Your Steve”, the engraving reads in tiny, yet fancy, script font. He stands up, and without another word, takes the collar, and moving behind me, he lifts the collar over my head, places it around my neck, and locks it onto me with a tightening of the wrench.

“Now, Loni, you can wear this whenever you want, but remember that when you have it on, you are mine…”

I’m speechless… I swallow, and looking into his eyes, without a word, I nod, I nod ‘Yes’. I don’t know if I like that notion or not, but maybe I do, as he tightened up the closure, my clittie started to stiffen. I can’t break my gaze away from his eyes…

“Ok, one more!” Steve changes gears. He hands me the last box, it looks like what you would put a longer necklace, or bracelet in. Opening it up, “I’m a pretty good guesser, I think to myself. Peeling back the tissue paper, I see that it’s a gold necklace, I think I saw this, or something a lot like it, in the airline magazine on the jet trip over: It’s a ‘Hawaiian Slipper’ Necklace. The pendant is in the shape of a thong flip-flop slipper, a rose gold color, and there’s a set of eight little stones on the strap of the thong slipper.

I look at him: “Just a wild guess, this is gold, and these are diamonds?” I ask Steve, holding the pendant in one hand and pointing at it with the other hand.

“Yes, it’s fourteen carat, rose gold, the pendent and the chain, and those are little baby diamonds on the sandal strap.” I have a friend at the golf club, owns a jewelry store down in Kailua-Kona, he sells these all over the country. “This will be a good souvenir of Hawaii,” he tells me, and then reaching over and grasping the day collar with two fingers, he finishes, looking into my eyes and smiling, “that is, that is if I let you go…” he chuckles and winks at me.

I look back over everything now, all these gifts, “I don’t know what to say, Steve. I think, in their own way, each one is very special. Although maybe the jury is out on this, I think, picking up the CB-6000 with two fingers. “You thought about this, all these gifts, didn’t you? And now, you’re making me feel bad, I didn’t bring you anything!”

Steve laughed, “Are you kidding?” I recall it was ME that invited YOU to visit. You are the guest. And you know what, you’ve already given me two sexy gifts, last night, and another one this morning.”

I smile, we’re looking into each other’s eyes again, we seem to be doing that a lot. Why is it, when I look into his eyes, I feel something nice down in my clittie? I lean over, and plant a soft little kiss on the side of his cheek, “Thank you,” I say, very softly.

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