wittlesissybaby

Roomies - Chapter 3

Published: June 11th 2023, 3:10:47 pm

Max hasn’t said anything today. I was up when he was getting ready for work, which is weird because I’m usually never up this early. But I guess I…wanted something to happen. I’m not exactly sure what I wanted. Last night seemed like it was a dream.

Did I dream that?

No. It was definitely real. I remember the taste of his cock, the taste of his cum. No dream is that vivid. No dream can make me that turned on. So I don’t know what I expected when I got up this morning, but I guess I was just hopeful for …something. Words of affirmation, a hug, a chance to suck his cock again…

Honestly just an acknowledgment of my presence would have been nice. But he didn’t even do that, just sipped his coffee while scrolling through his phone at the table.

“Can I get you anything?” I want to say, but bite my tongue, not wanting to sound like some sort of desperate housewife. I want to address the elephant in the room, to talk about yesterday, whether or not we’re square. Did the blowjob I gave him really justify a whole month’s rent? Does he want more? Do I want more? How weird will our relationship be if we were to start some sort of strange sexual dynamic? What if it stops? What if it continues?

“Well, I’m off to work.” he says, pushing back his chair, gathering up his things and heading out the door without so much as a glance my way.

“Okay by–” but it doesn’t even get all the way out of my mouth before the door slams shut.

Maybe he’s mad. Maybe he regrets what happened. I mean, it was his doing. He initiated it all and I just…let it happen.

Helped it happen.

I wasn’t exactly a helpless victim. It was me that was bobbing up and down on his big juicy cock by my own accord. God it tasted good. It felt good. Something I've denied myself for so long.

I’m not gay. At least, I don’t think I am. I’ve always had an affinity for women. They are majestic, beautiful creatures. I love seeing their eyes and smiles brighten up a room. The way they laugh and can have fun and dance like no one is watching. The curve of their hips, their breasts. Their supple movements, the way they casually tuck their hair behind their ear, and bat their eyelashes. There is no doubt that they are by far the more attractive sex.

But I've always been plagued with a feeling of inferiority. Not being the biggest in the penis department has left me with anxiety that I won’t be able to perform or please them the way ‘real’ men can. I have lingering visions of women standing around, laughing at me because I have a shy bladder and can’t pee in a toilet in a timely manner. Or I take off a beautiful woman’s clothes and she laughs at the size of my dick, or is disappointed when it's not able to get hard due to my underlying fear and shame.

The combination of these phobias has most likely caused my brain to warp them into a series of fetishes. It sexualized my short-comings. I get turned on by a woman insulting the size of my penis. I get hard to the idea of them laughing at me, degrading me, humiliating me.

My timidity when it comes to peeing in a toilet must have spawned the retention of such. ‘Since you can’t even use the toilet properly, maybe your teeny wieny is better suited for diapers instead!’ I imagine those laughing girls saying.

All of this culminates into this whirlpool of self-doubt, and leaves me feeling like less of a man than others. Thus, I guess, is where the sissy stuff came from. Perhaps it was society’s fault. In our culture, anyone not befitting of a masculine, alpha, macho-man persona is unabashedly called a ‘sissy’. I figured out pretty early that I belonged in that category, and must have accepted it from an early age.

Years of watching and reading porn only exacerbated my ‘problems’. I quickly learned what kind of things I enjoyed, and even found things I didn’t know I would enjoy. I was always attracted to diapers, but I didn’t know they could be combo’d with skirts and dresses. That was new. Two of my favorite things merged together in a perfect amalgamation. Combo that with a superior woman speaking to me in a humiliating, patronizing manner? Gold. Solid gold.

Then one day I found a video of a woman calling me a ‘wittle sissy baby’ and telling me she had a bottle for me. But this wasn’t just any bottle. It was a special bottle. And that’s when she brought in the giant dick that was waiting off screen.

I’ve never been attracted to men. Honestly. I’ve never looked at a man and found myself sexually attracted to them. Well, other than Ryan Reynolds, but that doesn’t count. I’m comfortable enough to tell when a man is good-looking, and can acknowledge it, but that’s usually as far as it goes. The idea of kissing, dating, or being romantic with a man does nothing for me. But the cock? Well…that’s a different story.

I guess the inferiority complex I have with women carried over to men as well. I’m not naive enough to think I’m anything above the bottom of the totem pole. I consider myself the bottom of the societal barrel. A subservient. A willing participant to what others desire. A submissive. To anyone, regardless of sex or gender. And so, I guess my brain can’t differentiate between who it is that I’m serving. But porn quickly told me that, if you’re a sissy, you’re going to spend a lot of time serving men.

I’m not sure if it’s a deep desire I’ve held all along, or if I unknowingly Pavlov’d myself into it, but eventually the idea of being dressed up like a little diaperslut and sucking some dick became a very big fantasy of mine.

And so we circle back to Max. We’ve lived together for almost 2 years, and in that time I’ve never imagined myself with him. He’s a big, burly, ‘alpha’ male, but not even once did I fantasize about being on my knees in front of him, sucking and worshiping his cock.

So now I’m conflicted. Did I enjoy what happened? I don’t think there’s any denying that. But I’m still hesitant. Caught in this weird limbo of right and wrong. I just got a little carried away, that’s all. I only did it because he told me to. Because I needed a place to live. If I didn’t do it, I was going to have to live on the streets. I was doing it for survival. Right?

He doesn’t say anything when he gets back from work. Just sighs in that exasperated way one does when they come home after a long day. He grabs a beer from the fridge, plops down on the couch, and turns on SportsCenter.

I sit in the chair several feet away and act like I'm interested. “So the Bruins had the best record in the regular season?” I ask, parroting what the news anchors are saying, “and the most points in franchise history? And they still lost in the first round of the playoffs?”

He just nods absentmindedly, lounging on the couch and putting his hat over his head.

Assuming he’s about to take a nap, I stand up to leave. Heading out of the living room.

“Where are you going?” he asks abruptly beneath his cap.

“I was going to go play some games.” I reply, a bit disconcerted.

“No you’re not.” He says simply.

“I’m not?”

“No.”

I don’t say anything for a bit, just have my mouth hanging open in confusion, so he continues.

“You’re going to put on an outfit for me.” He says, “The schoolgirl outfit will do.” He doesn’t need to clarify, but he does anyway: “The slutty one.”

My stomach drops. From fear or excitement I'm not exactly sure. “I…wh-what do–”

“Get made up for me.” He says, still talking beneath his hat, “I want you to look your best.”

******

My hands shake as I apply the last bit of mascara to my lashes. I’m not sure if I'm giddy with excitement or fear. Is this really happening?

I usually revel in the idea of dressing up like a little slut, but no one has actually seen the finished product. What is he going to do when he sees me like this? Will he humiliate me? Laugh at me? Tease me? Fuck me?

My mind swims with the possibilities. I stand up and check myself in the mirror. I definitely look passable, maybe even fuckable. After readjusting the ‘breasts’ of my stuffed shirt, I take a little turn, watching my mini-skirt lift as I twirl.  I feel…pretty. Desirable. I just hope he agrees. There’s butterflies in my stomach and I don’t even know what’s about to happen. Maybe it’s the thrill of the unknown, but I feel ready for any possibility.

The only thing left is to figure out what to put beneath my skirt. Should I wear a diaper? It certainly would be my first choice, but would it be his? A pair of pampers doesn’t exactly scream ‘slutty’, and I don’t want to turn him off or scare him away from whatever might take place. So I decided on a pair of skimpy boy-shorts. It only just hits me how ironic that term is. I didn’t feel like much of a boy when I wrapped them around my parts. If anything, it was like putting the final nail in the coffin that made me feel like a girl.

One last glimpse in the mirror before I saunter off into the unknown. I open my door with trepidation, it seems to creak louder than usual. I creep through the hall, the house is eerily quiet. At first I think he’s left, some kind of cruel joke. Or maybe he’s just napping. Should I wake him if he is? How awkward would that be? Hey Max, wake up, time to see your roommate dressed like a cheap whore.

But when I turn the corner, he’s sitting on the couch, bolt upright, a big smile on his face.

I scrunch up as I walk in front of him, suddenly very self-conscious. Does my hair look okay? What do I say? What do I do? Luckily, he helps me.

“Turn around.”

I do, legs quivering.

“All the way.”

A complete twirl. My arms stiff at my sides.

“Relax. Give me a little curtsy.”

I feel myself loosen a bit as I grab the hem of my tiny skirt, jut my leg out, and dip shakily.

I can feel his eyes panning me over. I feel like an object, a painting on the wall for him to admire, and I don’t exactly hate the feeling.

“Face away from me.” He growls. His voice is a little shaky, is he nervous too? Or is it…something else?

I tiptoe around, facing the TV. It’s off, so I can see my face reflecting in the black screen. I can see him too, he’s smiling, and his hand is rubbing over the front of his pants.

“Bend over.”

I do, hinging at the waist. I can feel the breeze hit the bottom of my cheeks as my skirt lifts, exposing my panties.

“You have such a nice ass.”

It’s such a strange comment. Not creepy, just…something he’s never said to me before. It makes me warm inside, to be complimented in such a way.

“Th-thank you…” I squeak awkwardly.

“Come here.” He says.

I turn, moseying up to him, perhaps a little too eagerly.

“Knees.”

I drop again, the same position I was in last night.

He’s still rubbing his pants. I can see his bulge, I can see his cock in my mind, my mouth subconsciously starts to water.

“I’m going to be honest.” He says. “I spent all weekend masturbating to the thought of you in this outfit.”

I didn’t know what to say to that, but it was oddly enticing. Someone imagining me? Using me as the object of their desires, and actually jerking off to it? I never knew that would be such a confidence boost.

“But seeing you now, it’s even better.”

I can’t help but smile.

“Do you like wearing it?” He asks, “Things like this?”

I look down at myself, covered from head to toe in feminine attire. The way it accentuates my curves and gives me this overwhelming feeling of joy is indescribable. But I only give a sheepish nod. “Mhmm”

“Good.” He smiles, “Because you will be dressed like this very often. If you want me to pay your rent, you are going to be my personal…what word would you like me to use? ‘Slave’? ‘Slut’? ‘Pet’? ‘Bitch’? ‘Whore’?”

“Yes.” I say, indicating I wanted to be all of them. Any word he used to describe me would suffice.

He nods in understanding. “Every day you will do what I say, when I say. Is that understood?”

“Yes.”

“Yes sir.” He corrects.

“Yes sir.” I repeat.

He reaches a gruff hand out, cupping my chin, rubbing a rough thumb over my cheek. It makes me feel small, subservient, obedient. Like a puppy getting patted. He slips his thumb between my glossy lips. Without even thinking, I start to suck on it.

“How do you want to do this?” He asks, “do you want me to be gentle? Or do you prefer me to be rough and mean?”

It doesn’t take me long to think of the answer. “Rough.” I say around his thumb, then resume sucking.

“You’re sure?” He says, eyebrows raised. “I can be quite harsh.”

I nod, bobbing my head over his thumb like it’s a cock, wishing it were a cock. “Yes sir.”

“Okay.” He shrugs, plopping his thumb from my mouth. “Our safe word will be ‘Roomie’. Use it whenever you feel I’ve gone too far.”

I nod, doubting I would ever need to do so .

He smiles, sitting back, then taps his leg. “Up.”

I’m a bit taken aback, not sure about the order, so he repeats.

“Up. Over my leg. Let’s go.”

Now I understand. I whimper as I crawl over his lap, I’m not sure if I’m just playing a part or am genuinely scared. Perhaps a bit of both. I can feel his cock pulsing in his pants as I put my own almost directly on top of it.

“Someone’s a little excited already.” He chuckles, reaching beneath my skirt to tickle my throbbing boner. He doesn’t pay it much mind though. I can feel him lifting my skirt so that my cheeks are exposed. “Look at your pretty panties.” He muses. I don’t even have time to thank him before I feel a sharp swat on my ass.

“Nnghh!” I yelp.

“You like that?” He asks sternly.

I bite my lip, ass still stinging, but nod. “Yes sir.” My voice is higher pitched, as if falling into submission has caused it to raise an octave.

Five sharp swats, one on each cheek. I whimper with each one. I’ve never gotten a spanking before, I didn’t imagine it would hurt quite so bad. Max doesn’t seem to be holding back, but I trust him. I know this isn’t his first time. I’ve heard the same smacks and yelps coming from his room when he’s brought home a girl–or even a guy sometimes. He seems to be no stranger to a D/s relationship.

Twenty more smacks in quick succession. My ass is on fire now. Where I was embellishing a bit before, my cries of pain have become much more genuine. I grip the cushions of the couch as he shows no signs of stopping.

By 40…or is it 50? I’ve lost count. But I’m having to bite my bottom lip to keep from screaming. Finally, he stops. I can feel the heat radiating from my butt. But my reprieve is short lived, he just needed time to yank my panties down. I give some pitiful plea of “no no no, please!” as he raises his hand to begin the onslaught again.

At around 60 or 70, I’m in literal tears.

“Do you remember your word?”

I nod, sniffling.

“Do you want to use it?”

I clench my eyes closed at what I’m about to say, shaking my head “no sir…”

I can feel him smiling down at me. “Okay then…”

My arms are flailing and legs are kicking with every smack now. He grips the former with his non-spanking hand, and throws his leg over my floundering thighs.

I regret every second of not using the safeword. I still consider using it, but I want to be strong. I want to impress him, as silly as it sounds. I bite my knuckle to keep myself from screaming loud enough to wake the neighbors.The leather of the couch is slick from my tears and snot. His blows aren’t as fast anymore, but they're stronger and more pronounced. Each one makes me squeal and sob pathetically. Whatever respect he had for me before has probably evaporated long ago.

After what seems like forever, the swats finally stop. I’m bawling into the cushions of the couch, and my ass feels like it’s black and blue. It’s a good thing I don’t have a job at the moment, because I doubt I would be able to sit at a desk tomorrow.

“You okay?” he asks softly. His voice has dropped that rough, hardness from before. I nod, not sure whether or not I’m lying.

I feel him fumble for something in his pants. I hear the click of a cap, then a squirt. A cooling sensation coats my buttcheeks as he runs his hand over them with some type of lotion. Did he have that in his pocket this whole time?

Whatever it is, it feels good against my burning bum. He rubs it sensually, taking his time, being gentle despite the damage he inflicted before.

“This is what will happen if you disobey me,” He says. I believe him, and it’s enough to make me not want to ever think about acting up.

He squirts another dollop of lotion, but this time it’s between my cheeks. I can feel his fingers coaxing my crack open. Tracing, searching for my little button.

“I like that you shave your pussy,” He says, “I want it to stay this way.”

I whimper, twitching as he pokes and prods at my hole. I can feel his dick stiffening in my lap as he presses his finger into me. The most pathetic moan escapes my lips before I can stop it. He plunges his finger deeper and deeper into me. I welcome every single knuckle, even press my hips backwards, hungry for more.

He chuckles again, “Such a little slut you are.”

I’m panting, like a bitch in heat. The combination of his finger and his words are driving me crazy. I’m humping backwards against his finger desperately as he presses down on my prostate. Mixed with the now dull throb of my blistered cheeks, it’s almost too much to handle. I’ve always enjoyed my pleasure spiked with pain.

He raises my hips up so that he can have access to my dangling dick underneath. “Such a teeny weeny clitty” he teases, wrapping two fingers around it. He works his hand up and down on my cock while driving his finger in me from behind. Before I know it, I feel that familiar tingle.

“Ask permission to cum.” he growls.

“Can I cum, sir?” I moan, not even bothering to try to make myself sound the least bit masculine. It’s pitchy and pathetic and desperate.

“Not yet.” He continues to work me with his masterful hands. I groan into the couch, grabbing at the cushions, his burly legs, a pillow, anything.

“Please!” I shout, “Sir! Can I cum?! PLEASE!”

I can’t hold out any longer. It’s by some small miracle that he says “You may,” just before I explode all over his lap. A second later and it would have happened without his say-so. What would he have done if I were to cum without his permission? I loathe to find out. He shoves me down on the floor in a heap, gasping for breath. It takes me a couple minutes to collect myself. When I do, he’s still smiling down at me in a victorious sort of way.

“Did you enjoy yourself?” he asks.

“Y-yes…sir…” I say between breaths.

“Good.” he says, “Because you have a mess to attend to.”

He points down at the gooey, white puddle I made on the crotch of his pants.

“Every load you make ends up in your mouth.” He growls, “Do you understand?”

“Yes sir…”

“Clean me up then.”

I don’t have the same eagerness as I did before. I’m a bit repulsed as I crawl between his legs and start lapping up my loser goo. But as my tongue runs over his pants I can feel the outlines of his hardening cock. I suck and slurp the mess off the hem of his pants, running my tongue through the flap of the zipper, making sure I get every last drop. He’s damp by the time I’m done, but he doesn’t seem to care.

He stands up. Again, it’s almost like nothing just happened. He goes to the cabinet, pulls out a glass, fills it up with water and takes a long swig. “Ahhh…” he exhales, looking off into the distance, then eventually back at me. “Go to my room.” He says, “I want you on my bed. Face down. Ass up.”

******

“This is my asshole now!” Max grunts, slapping my tender cheeks while he pumps his cock in and out of my rectum. “Tell me whose ass this is!”

The pillow is moist from me biting and drooling on it to keep from screaming. His dick feels amazing, but I’m not used to being pounded like this. There was only so much training I could do with my dildo…

“It’s your ass, sir!” I squeak louder than the springs of the mattress.

“Daddy.” He growls. “Call me Daddy.”

“It’s your asshole, Daddy! It’s your asshole!”

“I own you,” he groans, “Do you understand??”

“Yes Daddy!” I really gotta get my voice under control. It gets so whiny and wimpy when I’m getting fucked.

I can feel his dick swelling, getting even stiffer than I thought possible. “I’m going to cum!” He tells me, “Where do you want me to cum?”

“In my asshole, Daddy!”

“Whose asshole?!”

“Your asshole!!” I correct.

I can hear him laughing between the grunts, I wonder if we’ll joke about this later. It’s amazing what people say in the heat of the moment.

“I’m gonna breed you like a little bitch!”

“Cum inside me Daddy!”

“You’re fucking miiiine!!” an exasperated groan, a warmth filling my insides, I can feel him convulse behind me as he deposits his load in my rectum. He removes his member and collapses on the bed shortly after.

I don’t know what to do at this point. What do you say to someone that just came inside of you? ‘Thanks’? I wait for him to come to, still in the doggy-style position.

He peeks an eye open. “Go to your room.” He says. “You’re not sleeping here.”

I wonder if, now that he’s lost his lust, he’s no longer interested in me. Is this how girls feel all the time? Constantly wondering whether or not they’re good enough? Worrying if they’ve done something wrong?

I climb off the bed and take the (luckily short) walk of shame back to my room, his cum leaking down my leg.

When I enter through my door, there’s a buzzing coming from my desk. Did I leave one of my vibrating toys on?

No…it’s just my phone, but it shows you where my head has been all day. The light stings my eyes as I look at it. My stomach drops a bit when I see who’s calling.

I tap the little green button.“Hello?”

“You know, Jake…” Zoey’s sweet voice says, “Part of having a girlfriend means you have to actually talk to her on the phone every once in a while!”