The Other Side of the Tracks Ch. 03

Okay, that's...what the hell is this? It takes me a minute to figure out what it is, and then, I, honest to God, Daddy, I BLUSH. Don't get me wrong; it's pretty, what there is of it. Like, feminine pretty. I guess technically that's a thong; black stretchy string stuff around the waist, with lace on it, then a black string from the center of the back (only way that could work, I think) down to just under the crotch, where it V's back up to the waistband, with a triangle about the size of a folded cocktail napkin covering my twig & berries. The material is a very pretty print of pink flowers on a pearly white background.

Wearing the red panties last weekend had been a stretch for me. But those had at least provided coverage. Less than a pair of tighty-whities, but still. This...yeah, not so much. The string in my ass (which I have to route around the base of the plug), the complete bareness of my cheeks...and then the flowers. This; whew! Stretching already. The door to the bathroom had a full length mirror on it, and honestly, sir, I blush when I see myself. Then I turn and check out my rear end. I'm a little shocked to see that my smooth, hairless ass looks good, then I'm shocked to realize that I'm THINKING that my ass looks good, then I'm blushing again.

But if the very feminine thongs made me blush, the high heels made me shake a bit, even before I put them on. I struggled to get them on; I probably looked pretty funny struggling to get them on and strapped. And then I stand up, and demonstrate all the grace of a pig on ice skates. It takes me a minute before I can even stand, much less take a couple of steps towards the mirror and back. Checking out the scene in the mirror over my shoulder, I realize why women put up with this crap: My ass now looks fantastic! And then the whole shock and blush cycle starts again...

Looking into the bag, I pull out the blindfold and set it aside, then retrieve the last item. As I pull it out and look at it, its significance hits home. This is decision time. Am I really willing to go this far? I mean, this won't work...not in my "real" world, although honestly, that line just gets more and more blurry every day. This really comes down to trust. Do I, can I trust you, Daddy?

I turn and hobble carefully to the mirror, carrying the last item. I look myself in the eye. I see terror. I see panic. I see humiliation. I see confusion. What.in.the.hell.am.I.doing?? Who AM I even, anymore? I ask, eyeing myself up and down. I shift my eyes up to have a confrontation with this madman, eye to eye.

Desire. Passion. Lust. Fulfillment. And peace. I hadn't noticed these before, but there they are. All of the elements of life that have been missing from my life for so long; there they are. In the last month, I have completely upended every steadfast concept about myself that I ever had. And if I tell myself the truth, standing in high heels with a pretty, feminine thong on, standing eye to eye with this new reality...

I'm having the time of my life.

I stand back, looking at the overall "me," take a deep breath, let it out. I give myself a wink. "You got this, gurl."

Still holding my own gaze, I put the pink leather collar on, fit it to where I can still fit a couple of fingers between it and my neck, and put the little black padlock on it. There are two sturdy D rings at the front, one on each side, and then one in the back. Heaven only knows how those will be utilized. Then I begin my walk towards the cabin.

There was no key to the lock in the bag.

*****

Climbing the few steps up to the cabin, I am relieved to find there is still nobody else in the room. However, my instructions are to don the blindfold, and wait "in position" (on my knees, legs apart, hands clasping elbows behind my back) in the middle of the room. What if a member of the crew (for some reason, I'm assuming there is a crew, although the boat is not so large as to require one) has to come into the cabin for something? How are they going to react to a naked man in a thong and blindfold kneeling there?

Well, I guess we'll cross that bridge when we get to it. I estimate the middle of the room, kneel, almost killing myself in the process (damn heels!), and don my blindfold. And now I wait.

Just 5 or 50 minutes later, I can't really be sure, I hear the door leading to the back deck open, then shut. I hear two footsteps, but then the thick carpet makes it impossible to tell anything after that. I swallow nervously, and feel the collar fill with my neck when I do so. A minute passes, then two, then three, then-

Fingers close on my left nipple, pinch, then twist. I cry out, and fight hard NOT to pull away. As a reward, the nipple gets twisted again, and suddenly a spot of fire erupts on my left ass cheek, dead center. Ow!

Just as suddenly, the hand releases my tortured nipple. I wait for the hand to deal the same torture, but it doesn't come. Oh, this is going to kill my OCD!

Yeah, I know, Daddy; totally random thought. Or did you know that about me? I can't remember if I-

Shit! Another fire patch, this one right on top of the right nipple. See? That's unbalanced! It's not right to-

FUUUUCCCKKKKK! I can not help but groan in misery as the next strike lands on the bottom of the panties, smacking my little dicklet and balls in one cruel blow. At this, I hunker down a bit, trying to ride out the pain. A vise-like hand grasps my right nipple and brings me back upright; another firebomb from what I suspect is a riding crop lands on my lower back, making me arch upwards into the hand pulling my nipple off. My breathing is labored, but I regain my resolve a bit. I'm not going to break THAT easy, Daddy! I holler at you in my head.

Blows to both of my ass cheeks burn into me, but still I hold my tongue. I have no idea why, but I want to make you work for it, Daddy. To compel you to earn my tears. And at the same time...I want to make you proud of me. So onward, Daddy! Have at me!

And onward you go, landing spots of fire on top of other spots before those flames even die out. Only my face is spared. Back, nipples, belly, you're relentless in your peppering of my body. I feel as if all of my skin is on fire. Sweat is running down me, front and back, making each sore spot itch, increasing the torture.

"Damn, you're like a fucking artist!"

Daddy...who are you calling an artist? That thought penetrates through the hot fog of pain. If you're over there, asking that question, then...who has been doing this to me? Clarence?

You're reading my mind, aren't you, Daddy? I feel the blindfold pulled from my face.

Standing before me, in leather boots, a short leather dress, black gloves bearing the instrument of my torture, a black riding crop, stands...

A redheaded goddess I have never seen before. She has a wild look in her gorgeous blue eyes. She's breathing a little hard, and it's not just the exertion from swinging the crop at every sensitive square inch of my body. She looks...excited by her duties.

"Slut, meet...well,you will just refer to her as...Mistress. Mistress Red." I can tell you just came up with that, Daddy, but I am not here to question such things. Besides, her eyes are so captivating I could just stare-

"What the fuck are you staring at me for, slut?" the Goddess of Fire snarls. "Do you think I'm some slut like you, here for you to perv on?"

"No, Mistress, Mistress Red. I apologize, it's, just, um, you're just, I mean, you're-you're...beautiful."

This is the point where the red-headed goddess, touched by my adoration, softens her heart, and smiles at-

"No shit? Really? You think I don't know I'm hot? You think I need some sissy to reveal this to me? Hell, yes I know I'm hot! I've been told that by a hell of a lot more manly men than you!"

If I weren't staring at the ground, trying to avoid looking at her, I might have seen the evil grin tug at the corners of her mouth. I might have perceived the brisk swing of the crop up into my crotch, crashing into the only apparent evidence of my masculinity. Probably couldn't do anything about it, but I'd have known.

Maybe I could go ahead and start sobbing then. Then I would have a head start on crying when a second, then third strike, in rapid succession, repeated the same blow, sending me to the floor, writhing in agony.

I lay there, crying, as you and this Demoness chuckle. The vibration of the motors and the light jarring of small waves are rocking me, as if to soothe me. After a minute, her patience runs out, and she bends down next to me and speaks in a very mild tone.

"Does that hurt, slave?" I can only nod. "Good, because it's supposed to. That's what I do, slut. I hurt people. I use them for my pleasure, and I hurt them. Do you know why I hurt people, boi cunt?" I shake my head. The Demoness leans closer, half whispers to me: "I do it because I love to do it."

"Mistress Red is a friend of mine. We have some...shared interests, although she is more skilled than I could hope to be. She will be joining us for some fun." Your explanation and introduction do not in any way settle my fears, Daddy.

I watch you speak, but I'm still in a bit of shock. Thus far, our "play" has all been man on man, or should I say Man on top of man? The introduction of a woman into this has me spinning. I think of the robot on Lost in Space again: Danger, Will Robinson! Danger! Before, part of the dynamic was me submitting to a stronger male, especially with Clarence, who actually IS stronger than I ever was. But now, the agony I just suffered is coupled with a deep humiliation that it is a woman - and a GORGEOUS one at that - who is in utter control of my senses and emotions. I guess there was some vestige of masculinity left in me, because I feel it brutally ripped from me at this realization. Even a girl holds more power than you do, sissy! I tell myself. How humiliating!

And how utterly, inexplicably fucking HOT.

"Well, it may be fun for US," says Mistress Red, "but for you...maybe not so much." She laughs looking over at you.

You smile, but then you defend me. "Don't be so sure of that. My slut is a very...durable little sissy. He doesn't break easy."

"Is that so," asks Red, and she reaches down and pulls me back up to onto my knees...by my ear. Then she cups her hand under my chin and tilts my head up, though I submissively keep my eyes lowered. "Are you a tough little slut?" she asks. I am lost; at the moment, I sure don't feel all that strong. She pulls up hard on my chin. "Look at me, bitch! Look at me!" I obey, fearfully looking up at her face, into those deadly hypnotic eyes. "Your Master over there says you're tough. I say you're tough because you haven't been broken by me yet. If I break you, and I can break you, slut, you'll never be the same again. You'd never think of yourself as a man again. Believe that, sissy."

"Y-y-yes, Mistress Red," I reply. "I believe you."

She smiles again at me. "Well, I'm glad we got that straight. Lucky for you, your Master just invited me along to have some fun with you. And I intend to have a LOT of fun with you. Stand up!"

I struggle to stand up, causing Red to laugh hysterically at me as I stumble on the high heels. Between the heels and the rocking of the boat, it's a wonder I can stand at all.

"Oh, shit, Charlie," she says to you, "That's funny as hell! Sissy boys are always fun to watch the first time they try to handle what women do every day. I could run down a purse snatcher in 4" heels; he can't even stand up! Take that shit off, sissy," she instructs me. "You're not fucking up my fun just because you sprain an ankle."

Without comment, I bend over and unleash my feet from these hellish implements of torture, relishing the feel of the soft carpet under my feet. While I wiggle my ankles a bit, Mistress Red goes to the bar where she has laid a small black suitcase. Coming to me, she hands me two ankle cuffs.

"Put these on, slave," she snaps. "Hurry up!" I quickly wrap them around my ankles, and draw them snug but not tight, then stand up. "Hands!" I offer up my wrists, palms up, and Mistress Red cuffs them more tightly than I did my ankles. "Can't have you wiggling around, can we, slut?" Somehow, I sense she doesn't really want an answer from me.

"Rosita!" Red yells, scaring me. What the hell is a Rosita?

The back door of the cabin quickly opens, and I see a diminutive Latina woman, nude save a black collar, come quickly into the room, then kneel at Mistress Red's feet, and kiss her booted toes. "Yes, Mistress?" she says towards the floor.

"Help me with this slut's hand. You should know this process well," she sneers at the smaller woman. So evidently, I'm not the first person to suffer under Red's hands on this boat. Interesting...

Rosita stands up. She is simply perfection in size extra small. Her breasts are full, with dark areola and prominent nipples, a trimmed but not shaved bush, and as I will see momentarily, an extremely sexy ass. She crosses to the port side, and detaches a cable I hadn't even noticed from a ring on the wall. The end of the cable features a D ring that she then connects to the ring on the back of my right hand. She leaves that, and goes to the other side, although on that side, as she stretches up to unhook the cable, I can't help but see that you slide a hand up her thigh and stroke between her thighs, Daddy. Rosita simply stays in place, and even smiles at you, until you stop, at which point she thanks you: "Thank you, Master Charlie!" before coming back to me and connecting that cable to my left hand. At no point does Rosita make any eye contact with me, as if I am just a mannequin she is dressing for a store window.

I'm standing there, my arms can't come down, but nor are they stretched uncomfortably far. That, however, is about to change.

"Okay, Rosita, bring him up," Red instructs her slave. Rosita smiles at noone in particular as she goes to a switch on the starboard side, between your chair and the next, and flips it. A mechanical whirring sound begins, and the cables begin to each retract towards the ceiling on each side, drawing my arms up and out.

"That should be sufficient, pet," Mistress Red says. "Now, secure his ankles. Spread your legs, slut!" she snarls at me. I spread them as wide as I can; Mistress kicks them out further. The process for my ankles is a little different: Lengths of dog chain are extended and measured to keep me secure, then D rings are applied to keep me as wide as possible.

I am now an "X" in the middle of the room. I am literally vulnerable over every inch of my body save the soles of my feet, though I feel confident Mistress Red could get to me there, too.

"Nice work, Rosita," she says to her slave, who comes to her and looks adoringly up to her. "What do you think of my playtoy for the evening, pet?"

Rosita looks me over. "El no es una hombre masculino, señora," she says, smiling at me.

Mistress Red notices my blush. "Tu hablas español, puta?" she asks me.

"Si, Señora Rojo," I respond. "Pero solo un poco. Hablo mas alemán."

"Very interesting," Red says. "A multilingual slut. Which means you're still just a slut. And certainly NOT, as Rosita observed, a masculine man. It would be interesting to hear you beg in...how many languages?"

"Four, Mistress Red. I speak some Romanian, too. And bits of a few other languages."

"Well, enough of that; I wanna have some fun. Rosita, the clips!" Rosita squeals in excitement, and goes and retrieves a bag from the infamous black box, handing them to her Mistress. "Good girl. Now, you go have a seat on Senor Charlie's lap. You take good care of him, you hear? He has my permission to discipline you however he sees fit!"

"Si, Senora! I will take good care of heem!" Rosita seems quite happy to go and take MY place with you, Daddy. Looks like she's been there before, I think jealously.

My face is pulled away forcefully from that scene by Mistress Red. "You don't need to be looking over there, bitch! Your Master can do whatever he wants, with whoever he wants. He claims YOU, not the other way around!" My own words come back to me: 'Possessions don't limit owners, Daddy.' "Besides, I'm going to be getting your full attention on ME."

Mistress opens the bag, and continues as she reaches in. "You know, lots of people love nipple clamps. They're adjustable, you can make them as tight as you want, attach weight to them..." My eyes open at THAT unpleasant thought! "and they don't fall off easily. But me, I'm an old fashioned girl," she explains, as her hand comes out holding several wooden clothespins, the kinds with metal springs in them.

"See, the painful part of a nipple clamp isn't just when it is put ON the nipple," she continues, as she pulls my left nipple out from my body a couple of inches, twists, then releases it. She holds a clothespin fully open over the nipple, then, looking into my eyes and smiling, she releases it suddenly, snapping it down on my little bud. I wince at the pain. "The best part is the burn after you remove it after a while, and the blood flow returns to the nerves and the tissue," she explains, as she repeats the process on the right. Once both of them are on, she grips both and gives them an extra squeeze, as if making sure they get plenty of bite. At this, I groan out loud. "Feels grand, doesn't it?" she asks, mocking me. She moves behind me.

"Damn, your slut does have a pretty nice ass, doesn't he, Charlie?" she says to you, smacking me on first the left cheek, then the right with her open palm. "Have you boys popped that yet?"

I glance over at you, Daddy, and I see that Rosita is now straddling you, and you're taking your pleasure with those titties. Bitch! I think. Silently.

"What do YOU think?" you reply, chuckling.

Behind me, Mistress laughs. "I bet Clarence had fun with this!" She leans in up to my ear and whispers, "If you're really, really lucky, they'll let ME have a turn with your little pussy. I will change your life." Red licks at my ear, then bites it. She backs away.

"The other great thing about these old clothespins is that they're like you. They're cheap. Which means you can get a whole lot of them for what you'd pay for one of the expensive ones." With that, I feel her reach around me from behind, and I steel myself as I feel her cup my balls. She strokes them gently for a moment, and it is an incredibly sexy feeling.

All the way up to the point where she snaps a clothes pin on the sack, right in front, right between the boys. As I struggle to accommodate the pain, she snaps another, then another, until my scrotum literally has a beard of clothes pins hanging from it. She grabs my little clitty-dick, which momentarily thought about getting hard watching you and Rosita, then retreated as it felt its neighbors being assaulted. She pulls it out from my body by the head.

"Damn, ain't much to work with here, is there, slut? No wonder you've taken to cock so well! This thing is pretty much useless, isn't it? Well, I guess not completely: I'm having fun with it!" Red laughs at me, drowning me in humiliation in front of you, Daddy, and Rosita. Both of you laugh at her comments. As they laugh, Red snaps a pin onto my frenulum, then another. She pinches the head of my cock, getting one onto the ridge behind the head, but it almost immediately begins to slide off, delivering a very painful pinch as it did so.

"Oh, did I hurt your little clitty?" Red asks mockingly from behind me. "I so sorry! Here, I make it better!" And with that, she does the same thing again, but pinching the head harder, pushing more of it into the grip of the clip...and achieving the same result. I yelp again.

"Hmmm, we may have to come back to that with something a little more...secure." Coming back to my front, she works her way around my body, locating any place where she can get enough skin - just barely enough - to attach another clothespin. Finally, she runs out of space.