Sissy Loni on the Big Island Ch. 05

Here we are at the beginning of Chapter Five, and the middle of Sissy Loni's first full day on the island. If you haven't, you're encouraged to go back and read from the start. In chapters one and two, there is a lot of scene setting and character building, if you're interested mainly in the guy on gurl 'action', chapter three would be a good place to start, as well.

Recapping Chapter Four, in her first full day in Hawaii, sissy slut Loni wakes Steve up in a wonderful way, and then, after touring some of the northwest corner of the Big Island and an early lunch at an outdoor café, Steve takes Loni out to a remote, isolated spot right on the water, a small, totally private bluff. Somehow, in a few short minutes, Loni finds herself totally naked, save for sneakers and a new silver day collar, kneeling on a blanket at Steve's knees. After a few short minutes confessing her feelings for his cock, and her submissiveness and crossdressing fetish, she finds herself with Steve's thick cock in her mouth:

.

.

I have Steve's cock in my mouth, it's all the way in, and I'm doing the best I can to keep from choking or gagging. Maintaining eye contact, Steve is not smiling at all, but just very slightly, nodding in approval. I'm not moving my mouth up and down on the shaft, just sucking on it, and trying to lap my tongue against the spongy tissue on the underside of his shaft, the frenulum. I know on my own boi-clittie, this is my most sensitive spot for feeling pleasure, and all of the blow jobs I've given the past few years, in my sissy life, I've not ever had a guy tell me to stop, when I was tonguing or kissing this part of his cock.,,

"Take my cock out of your mouth, Loni, I want you to start kissing it, while you look it over very carefully. And talk to me, Loni, tell me about what you are seeing and feeling. Don't look at me, look at my penis..."

Instantly, I comply, and looking at his penis, I start kissing the cockhead, the dome, so to speak, the 'purple helmeted warrior', as it is sometimes referred in the slang of some erotic stories that I have read. Staring at the smooth dome, I stop kissing for a bit, and as instructed, I start describing it: "It's so big and smooth, I love the way your cockhead sits at the top of your shaft, and protrudes away, to call your penis a mushroom-headed penis, it's an understatement, It doesn't do justice..." a quiet giggle follows from my mouth. "I loved the feeling, both last night and this morning, when you were inside my boi-pussy with just this part," as I stop talking and opening wide, get his cockhead into my mouth and squeeze my lips at the base of the circumference of his cock head. Then, pulling off it, with a soft 'pop', I spread another dozen kisses in random spots, one by one, soft little kisses, on the smooth, round dome. "I love having my tongue right here, Daddy," as I take the very tip of my tongue and touch it to the slit at the top of the cockhead.

"And these, these are awesome," as I hold the shaft just under the cockhead, with just two fingers, and turn Steve's penis sideways, as I trace the big veins that define the sides of his shaft. My tongue traces the curved path they make around the hard shaft. "I can't explain it, exactly, Daddy, but when you are fully erect, and your cockhead is full and round, and I look at these veins on your shaft, it's almost like your penis is angry, it's telling me it's ready to explode..."

And then lifting up his penis, upward just a bit, I lean in and kiss the soft underside, just below the head, the frenulum, as I've mentioned. This is the part I was trying to tongue just before, when I was holding Steve's penis all the way in my mouth. I flick at it with my tongue, biting into it, sensually, ever so gently with my front teeth, I pull away to speak: "and this part, Daddy, I love this part, too. When I am touching this part of you with my tongue, somehow, I feel your excitement transmitted to my tongue, and that feeling goes all the way into my core, and then to my clittie. When I have ANY part of your penis in my mouth, or I'm kissing it, it makes me excited, but tonguing this part of you seems to make my own clittie as hard as if it was being touched, being stroked..."

"Very nice," Steve interrupts, pulling his cock away from Loni, he is just holding it, stroking it very slowly with that hand. "Very nice. Now, Loni, tell me more about yourself, tell me more of the details about your crossdressing and wanting to be a sissy..." With his free hand, he sticks out his pointer finger under Loni's chin, so she understands the need to make eye contact.

"Damn..." I think inside my head, thinking, but not speaking these words: "I look into Steve's eyes, it's crazy, kneeling here naked, all I want to do is spill everything out, I feel like I've been injected with truth serum..."

And then, speaking out loud, looking into Steve's eyes, I begin: "I think I was like a lot of guys growing up, shy, and not being very big, I felt intimidated by the bigger guys in school, and I felt intimidated by the really good looking girls, who wanted to hang out with those big, hunky guys. I spent a lot of time alone, on the computer, and in high school and college, discovered the world of porn, and did a lot of reading about sexuality, and read a ton of erotic stories, in all different areas. In college, I began gravitating to sissy porn, the thought of crossdressing to look like a girl started to have appeal to me. In the porn that I started to watch, more and more, I'd sometimes just pause the video when an image of a big, beautiful cock would be displayed. I'd stare at it, think about it, how big that cock was compared to my own little thing..."

Steve is focused on Loni's words, listening very carefully as she continued: "And then, you know I've talked about Sarah, we were lovers during our senior year, and then were married two years, while I worked on my master's degree. So, my interest in porn and thinking about sissies quieted down for a while. Sarah never heard a word of any of this with me, she never discovered or suspected that I had this interest. I let it lie, dormant. We had an ordinary heterosexual relationship, except that I really wasn't very good with my penis, not good at fucking her. She mentioned a few times that she thought I was smaller than average, and often, during our lovemaking, I would suffer premature ejaculations. So it wasn't long into our marriage that Sarah would let me cum in her pussy, or stroke me off real quickly, and then I would settle in between her legs, and we'd spend most of our lovemaking sessions with my head between her thighs, and me licking her to a few orgasms. Sarah was multi-orgasmic, and sometimes I'd spend an hour or more just licking her... When we start off we me cumming inside her, she'd have me lap my cum back out of her.

I stops talking for a moment, just looking at Steve. And then after a few seconds of silence, Steve asks: "Then what happened, Loni?"

"Well, in that second year of marriage, Sarah found another man, fell in love, left me. I guess not only did they hit it off on the mental level and had similar interests, she mentioned to me, during her divorce, that he was much bigger than me in the manhood department, and had great stamina. We split, divorced after two years of marriage, and that coincided with me finishing my grad program, and getting a job and moving to California. Considering I only had a master's degree, I had a pretty good salary, I could actually afford to live in California..." I said, smiling... "and living alone, I had plenty of free time, and opportunity to go back and explore that latent interest of mine, time to explore... my feminine side?"

Continuing, "So those first two years out there, my interest grew and grew, I knew, I KNEW this was something I had to explore. It was during that first year, I started buying feminine things, and wearing them at home. I moved from panties and stockings to makeup, wigs, shoes, everything... The second year in California, I went out a few times, to adult arcades, adult video stores, the ones with booths and glory holes... I'd go dressed in my guy clothes, but would wear lingerie and thigh high stockings underneath... I'd find a booth with a glory hole, take off my guy clothes and give blow jobs through the glory hole..."

Another pause, Steve nods to me, to continue...

"I didn't go a lot, but I'd go once in a while. I never did anything at those places except give blow jobs. After a while, I found Club Sissy, where we met online last year, and I also posted and answered posts at Craigslist, before it closed, and then at Doublelist. I met, I visited a couple of guys from those sites, it was ok, but I never met anyone that I wanted to visit a second time. If the guy seemed nice, the sex would maybe not be so great, and vice versa... Just never clicked with anyone, and it is SO hard, it takes SO much energy to try to arrange a meeting with someone, without them flaking out on you."

"Well, I can understand that." Steve comments, still slowly working his cock. "That even pertains to online phone and camming sessions. It is way different making a friend like you, that we can arrange regular meetings, rather than finding a succession of satisfying one time meet ups... So then go on, please continue, I'm finding this interesting." Then, reaching down to me and touching my day collar, just lifting the front upwards, a few millimeters with one finger, Steve adds: "This are things that Daddy needs to know, you need to tell me all this..."

"Okay, Daddy..." The words are just flowing out of me now... "So that was a few years ago, that next year, the third year I was in California, both my parents died, you already know that; we've talked about that before." Steve nods, I continue: "And they left me independently wealthy. I know, seeing now where you live, the cars you own, the presents you've bought me, you are a wealthy guy. I think the only thing I like about that, is in my mind's eye, it tells me you are a super-successful person. You are... or were a powerful businessman. Confident in yourself. And then on top of that, look at you: you're really a man's man: big, strong, good looking... And with this, too..." I smile and lean over to kiss the head of his cock."

"But anyway, the past couple of years, this is where I've been. I feel more comfortable these days in gurl mode versus being a guy. I know, I am more confident in myself, the way I look... I LOVE catching guys when they check me out when I'm in gurl mode."

"Well, Loni, it's easy to see that... you're beautiful, you have a pretty face, a nice look, and... you have a killer body! Your legs are fantastic, thin and shapely, your bum is nice and round, and you keep yourself so nice, you're smooth and tanned, all over. You must lay out and tan in the nude?"

I nod to that question, yes. "Thank you, Daddy, that compliment makes me feel good... I liked it when I caught you staring at my ass on the stairway last night... So anyway, long story short, here I am, I'm going to turn thirty this year, Daddy... I have this lifestyle managed now, I can work from home, I can go out and do my business, shop as a guy, and I can go out, too, as a gurl, as Loni... I think I'm passable, don't you?"

"Yes, you're totally, absolutely passable. Except if people find you have these..." Steve reaches down and wiggles one of Loni's breast forms up and down... And whom are you seeing, back home, in California? Anyone? Male? Female? There are many, many men that absolutely adore pretty gurls like you, that also have this..." He reaches down and squeezes my boi-clittie. "As I do..." he says to me, smiling just a bit.

"No one, Daddy. I do have a couple other friends, that I meet online the same as you and I do, from Club Sissy. I chat with them, phone, with or without camming. A couple of guys, and a couple of gurls, too, the gurls have become friends, sisters of sorts, we chat, and then cum together before we finish. I'm only going to the arcades once every few months. I have to be honest, sometimes the emotion, the need builds up inside me, the only way I can satisfy it is by having a hard cock in my mouth. It settles me down, quiets me down, it satisfies that need. That's about all. That's pretty much the totality of my social life as a sissy."

"Maybe a good spot to finish, Loni. Thank you for sharing all of that. It's important to me, I would like it that you feel free, safe, to confide to me, anything that's on your mind. Anytime. Now, maybe it is a good time to finish up here, to move on to the next thing in today's agenda."

With that, Steve makes it clear we're not done here. We're just done with the conversation...

He lifts his cock up off his lap, offering to me. I tilt my head to one side, and just let a small sigh, I guess of satisfaction, appreciation of Steve wanting to listen to me, I gladly move my face to his cock, opening wide, letting the thick flesh all the way into my mouth. I'm immersed in my world of subspace, of being subservient, submissive to my lover.

It wasn't easy... I kneeled there for fifteen more minutes, I guess, as I alternately sucked on and slid up and down Steve's hard shaft with my mouth. At first, he was just passive, letting me do the work, but then, after five or ten minutes, I could feel him become a more active participant in this process. Finally, near the end, he slips his hand behind my head, and uses it to force me to move up and down his shaft faster and take him deeper. Fighting my gag reflex, it's all I can do to comply with Daddy's strong hand. Finally, both hands cradle the back of my head, and holding me still, with his cock deep inside my mouth, the tip of it at the entry way to my throat, he shoots six, I count, powerful shots of semen down my throat. In this case, this occasion, I didn't even get a chance to taste the loads on my tongue, they just were shot directly down into me.

I keep him inside my mouth, letting him soften, until Steve decides he want to pull out, for this intimate exchange of fluid to be over. With his two hands on the sides of my face, he cradles my head, and gently pushes me away, off his cock. I open wide and look into his eyes...

"Mmmm, that was nice, Loni, thank you... Was this ok, was it ok to come here?"

I can only nod, now, yes.

"I like the thought that my seed is inside you... Even though it's only a relatively small amount of cum, I like the thought that it's in your stomach, and in there mixing with our lunch. That it will get digested, and flow through your arteries and veins... That the cells of your body will use some of me, my cum will nourish you today..."

Hmmm, I never really thought about this before, but the biologist in me totally understood, that little 'high-protein snack' Steve just fed me, will be digested and used in my body, just like any other food I eat. I smile, "Thank you Daddy, that was a nice dessert to have, after our lunch," I say, winking at him. I feel a little better, a bit less submissive, and I continue: "It was nice to come up here, I am amazed that no one knows about this space, you were right, it is totally private. It felt amazing, it was very exciting, incredibly powerful, to be told to strip naked for you. It was nice to be there, close to you, it was nice to have you ask me about me, about my life..."

Steve stands up, reaching out a hand, I grab it, and he helps pull me up off the blanket. My knees are a bit sore and have the impression of the blanket and ground impressed in them.

"Time to get dressed, Loni. Look at you, you're bare naked!" Steve joked, pointing down to my clothes.

It was quick work, to get my bathing suit and sundress back on. I look at Steve: "How's my face?"

He looks me over, and wipes one of my cheeks with the back of his hand, to clean a smudge, I guess. "You're beautiful..." He smiles, I smile, too.

The walk back to the car went quickly, I was a lot more confident in the way and moved a lot faster on the way out to the parking lot. There were only a couple other cars there, quickly, we got the car packed, and taking down the top, I tied my hat down onto my head, and we're quickly on our way, we have to double-back to the east, to get to the main highway, but soon enough, we're headed west, back to the coast, to 'Steve's part' of the island. An hour or so, and I recognize this part of highway 19, we are near Steve's development, and soon enough, we're parked, in his driveway.

Steve puts the top up, and then, before exiting the car, he starts to talk to me, quietly, with a serious look on his face: "Loni, I hope that was a good experience for you, today, what we just did... It was important to me. If you want to be here as my sissy this week, me as your Daddy, it can happen one of two ways: we can roleplay it, you can pretend to be my submissive sissy slut and I will roleplay being your Daddy... Or it can be real... If it's real, you will be, in real life, my submissive slut, my whore. And while we are partners, and lovers this week, you will also know I am in charge of us, in charge of you... And that is why I bought you this," he said, touching my day collar, "And that is why we went where we did today, and why I had you get naked for me, naked to the world, and talk to me, and service my penis. We could have done that on my patio this afternoon, you would have been safe, protected by the privacy the patio offers. But going out to my spot, and doing what we just did, this was important to me." He pauses. "Do you understand... Do you agree?"

Processing his words as he speaks, there's a pause, just a brief pause, and I nod, yes. "Yes, Daddy, I agree with you. And, Daddy..." I continue, "I don't want to role play with you..."

Steve smiles. He leans over to me, and putting an arm around me, pulls me tight, and kisses me, tongue kisses me deeply, with real emotion. We kiss for several minutes, our tongues tangled, exploring each other's mouths. He bites my, gently, on my lips, with his front teeth. He lines my neck with little kisses. Finally, we break apart...

"Phew" I say out loud, exhaling and trying to catch my breath. "That was nice, Daddy."

"Let's go in the house." Steve says. "We should talk about what we'll do the rest of the week. We have lots of options, and I've already made a couple of reservations, for a few activities..."

I nod, and open my door and get out, and after grabbing my bag from the trunk of the car, we head into the house. In the landing of the bottom level, Steve looks at me, and tells me, asks me: "After what we've done already today, I'm in the mood to sit out in the sun, relax a bit, and talk about the rest of the week. And you know what I'm picturing right now, in my mind's eye?"

"Oh my God," I think to myself, "is he thinking about sex, more already? This guy is an animal..." Thankfully, those words were only in my head and not said out loud!

Then speaking, I DO say out loud: "No, Daddy, what do you see?"

"A nice cold glass of Rosé, what do you think?" He's got that big smile on his face again.

I giggle. "I thought maybe your mind was think of something else..." and I wink at my Daddy. "Rosé sounds wonderful."

Now, Steve comes up close to me. "How about you put on one of your other swimsuits. Do you have something more daring than that tankini? And, if it's okay with you, why don't you relax a little, and take these things off..." he says, grabbing my breast forms with both hands. "You don't need them right now, I'm fine to have you, just you, in the suit. And when you come upstairs, I'm going to take this off of you, for the rest of the day, maybe." He said, touching the day collar.

I nod back to Steve, and say with a smile: "Yes, yes, to all of that!"

"Ok, then don't take too long. I'll see you out on the deck. I'm going to put on some swim trunks, too. I'll get the wine ready..."