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wittlesissyb4by · 1 month

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Chapter 2

Chapter 1 Here

“I’m afraid we’re going to have to let you go.” Mr. Pennyworth says.

It feels like a dagger has been shoved into my stomach. I’m not sure what to say, so he just continues anyway.

“Your productivity is by far the lowest in the company, you’re not reliable to show up on time or even at all, and your long hair is unprofessional and not befitting of this company’s standards.” He clears his throat, sifting through some papers. “We also have reason to believe you called-in on Friday without actually being sick.”

“What makes you think that?” I say, finally speaking up for the first time.

He shrugs, “Let’s just say we got an anonymous tip.”

******

“Everything alright with you?” Max asks, moving his pawn forward to free up his bishop.

“I’m fine,” I say, half-heartedly moving my knight with no clear plan in place. “Lost my job today.”

Max frowns, moving his bishop out as I expected. “I’m really sorry, dude. That sucks to hear.”

“Yea…it’s fine, I guess,” I sigh, “Didn’t much like it there much anyway.”

He still hasn’t said anything about the other day. I’m not sure if he actually saw anything, or he did and just doesn’t want to bring it up. How do you talk about seeing a bunch of sissy toys and diapers in your roommate’s room? Is that even something to talk about?

I remember back in college when my roommate at the time had found a slew of sissy porn on my computer. I was there when he saw everything. That sick feeling in my stomach took forever to go away. It’s back now.

“Well if you start applying for jobs, you can always use me as a reference. Just say I’m an old manager or something.” He says, putting his Queen in a precarious position. I seize the opportunity and take it. I realize too late that it left my King open for an easy assault. An obvious trap I should have seen coming.

“Checkmate.” Max says, smiling.

******

As the weeks went by, so did the job opportunities and applications. I rarely received any callbacks, and even if I got an interview, I’d either get ghosted afterwards or they would call and say something to the degree of “after careful consideration, we’ve decided to go with another candidate.”

God, the job market is rough.

My bank account is dangerously low. I probably should have done a better job of saving for times like this, but I guess I was more excited about buying outfits and diapers. Still, I’m not going to make it through the next month without some sort of income. It’s time to have the awkward conversation with Max.

“Hey, man. Can I talk to you for a sec?” I say, shuffling my feet into the living room.

He pauses the hockey game and turns to me, “what’s up?”

It’s such a weird topic to bring up, but I have to bite the proverbial bullet. “I’m having trouble finding a job…” I say sheepishly, “I didn’t work long enough at my last one to get severance, so…I’m a little low on funds.”

He just sits there, always with that stoic expression, listening intently. He doesn’t say anything, just lets me continue.

“So…umm..I’m uh, gonna be short on rent this month.”

Again he continues to stare at me, as if deep in thought, stroking his beard. It almost seems a little exaggerated. Like he’s acting.

“I see,” he finally says. “So you need me to help you?”

As demoralizing as it is to admit, I have to. “Yes…”

He smiles. “Okay. No problem.”

“Really?”

“Yea.”

I don’t know what to say. A weight of anxiety and fear is lifted off my shoulders. I can feel it melt away as I start to relax. “Thanks man, I really do appreciate it. I’ll find a way to make it up to you, I promise. Anything you need, just let me know.”

His eyes have a strange glint to them. Like he was hoping I would say exactly that.

“I actually do have a job in mind for you,” He says, “You can start today.”

I sense a sudden shift in the air around the room. He leans back on the couch a bit, patting the seat next to him. I find myself sitting down beside him, not exactly sure what’s going on, but sensing something amiss.

Max puts his hand on my leg, “it’s okay, nothing to worry about.” he says softly. I feel myself release a breath, feeling comforted, but still a little uneasy.

It’s like he’s holding something back. Like he’s trying to find the words but doesn’t know how to say it. I wonder if he knows. If he saw the things in my room.

“I saw the things in your room.” He says.

Yea, I’d say he knows…

My stomach does that familiar churning. The shame of what I've done, or been caught doing coursing through me. “I-i can explain…”

“Don’t bother.” He says, waving it away. “I’ve always had my suspicions.”

I didn’t know what to say to that. I’ve always tried to be so reserved and secretive with my true desires. I didn’t think anyone else would notice.

He shifts on the couch again. When he does, something catches my eye, there’s a very large bulge in his shorts.

Noticing me looking at the log snaking down his leg, he starts running his hand over it and smiling. “Have you ever sucked a cock before?”

I realize my mouth is hanging open. I gulp, shaking my head. “Not a real one.”

He laughs at that, it breaks some of the tension, then he shrugs. “Well, there’s a first time for everything…” he gently pulls at his zipper, snaking it down ever so slowly. But he doesn’t pull it out, just leaves it open, letting my imagination run wild. “Do you want to suck it?” He asks.

Again I find myself dumbfounded, this is all happening so fast, but before I can think about it I find the word escaping my lips.

“Yes.”

He chuckles. “Good, because you were going to have to do it anyway. This place ain’t cheap.”

After our awkward laughter dies down, I’m left in the precarious position of what to do next. Luckily, he guides me after several seconds of silence.

“Open my pants.”

I reach a shaky hand to his button, it takes me a bit to get my fumbling fingers to work it free.

Again, I’m lost as to what to do next. Should we kiss? Do I close my eyes? What do I—

“Take it out.”

His direction helps. It’s easier for me to follow orders than it is to take initiative in such uncharted territory. I reach my hand into the waistband of his boxers, feeling around for it, my heart beating out of my chest. It doesn’t take me long at all to find the warm, fleshy member. I gently pull it back, it bends a bit before snapping out of the boxers to stare straight up at me.

It’s big. Very big. I can barely wrap my fingers around it. The veins are popping out the side, and I can even feel his own heart beating through it. Pulsing. Rapidly. He’s just as nervous as I am but he doesn’t show it.

“Well...it’s not gonna suck itself…”

I realize I’ve been staring at it for a while. I use my other hand to wipe the drool from my mouth. Maybe I shouldn’t have. Somehow my throat feels both dry and wet at the same time, it doesn’t even make sense. Finally, I push past the nervous excitement, and lean forward. His cock seems to grow as it gets closer to my face. I’ve imagined this moment over and over for years. I’ve watched countless videos through the lens of girls wearing a GoPro on their head taking big, giant dicks into their mouths. But somehow this is different. I’m the girl now. It’s my POV, and it’s what I've always dreamed of.

I open my mouth when I’m inches away and close my eyes, imagining I'm one of the girls in those videos.

The head of his dick already feels different than my dildos. It’s squishier, warmer, and tastes just a little bit salty, but in a good way. In a great way. This is what I've always wanted, and I’ve finally gotten it.

I hear a soft moan escape my lips just before they close around his cock. It sounds pathetic, but I don’t care. Things finally feel…right. Like this is what was supposed to be in my mouth all along. All those things they told me in sissy porn were true.

I take him deeper in my mouth. I find it easier to slide it down my throat than my dildo. I take it as far as I can until my eyes water, then go back up for a breath.

In the overwhelming rush of stimuli, I forgot all the techniques I’ve practiced for so long. I try to remember: swirl your tongue, suction on the way up, not down, and most importantly: keep it nice and wet.

I let the drool run from my mouth, using my hand to coat his cock with it, taking a breath before diving back down.

“Someone’s been practicing.” He breathes.

I melt at his praise. I always wanted to be a cocksucker, and I always hoped I’d be a good cocksucker. But you never really know, my dildo doesn’t make noises.

But him? He was breathing heavily, moaning, groaning, and doing all the things that told me I was doing something right. It ignited a fire in me. With every grunt he made I found myself getting more and more enthusiastic so as to make it happen again.

Leaning over across the couch next to him is a bit awkward, though.

He notices. “Get on your knees.”

I take him out of my mouth and scramble a little too eagerly onto the floor between his legs.

He looks down at me, almost victoriously, like his plan has come to fruition. I am in no way perturbed. In fact, my cock is screaming inside my pants. I don’t think I've ever been this hard in my life.

“Looks like you’re enjoying yourself.” He says, apparently noticing my penis poking prominently through my pants. “You can touch it.”

Is that his decision? I guess so…because as soon as he says it I find my hand going inside my pants.

“No no.” He says. “On the outside. Rub it like you’re a girl. A sissy girl.”

Just the sound of that word gives me a wave of pleasure. I’m so hot and bothered that my body is quaking. I love the way he’s dominating me. Taking my power away so I don’t have to make the decisions myself, and therefore making me more relaxed about doing something I may otherwise have chickened-out on. Would I be here, on my knees, about to suck his cock if he hadn’t made me? Is he making me? Or am I doing it on my own volition?

I knead the front of my crotch. Feeling my throbbing cock and nestling my aching balls. I feel a bit weird with him watching me, so I turn my attention back to his cock. Well, more specifically, his balls. I’ve learned that when worshipping a man—as I’m doing right now—maintaining eye contact while lapping at his balls is one of the perfect ways to show your submission. I also know (from being on the receiving end) that having your balls sucked does not feel nearly as good as porn makes it seem, it’s actually kind of painful.

So after licking his sack and stroking for several seconds, I spit on his dick and take it back into my mouth with renewed vigor. My own balls are aching at this point, I can feel them turning blue. I use two fingers and twirl them in circles over my pants while I bob up and down on Max’s dick.

“Fuck yea…” he moans. God it feels so good to make him make those noises. “I’m gonna cum.”

So am I.

Knowing he’s on the verge gets me insatiably hot. I want nothing more than to get him to bust in my mouth, like some sort of primal need.

I hear myself moaning again. I’m not sure if it’s from the pleasure I'm giving or receiving.

“You want it in your mouth?” He asks considerately.

“Mhmm!!” I swoon hungrily around his dick. My hand gyrates over my own. The thought of making a man cum in my mouth is too much to handle. I feel a warmth fill my pants as I shake and convulse, trying to keep my focus on his dick while I spasm in an intense orgasm.

I feel the desire begin to fade. The reality of what I'm doing seeping in. This is my roommate, and I’m on my knees in our living room slobbering all over his big dick like a girl he just met on Tinder.

“Ohh yea…” he twitches. I can feel the head of his penis swelling, even more than it was before. It gets me excited again. Eager. Desperate. “Right there, just like that! I’m almost there…”

I’ve never been on the receiving end of that statement. Guys saying they’re almost there but are actually a few minutes out.

My cheeks are starting to burn, my throat is getting sore, it burns from the bile of gagging, I need air, to take a break and a breath, but I don’t want to lose my progress. I need to power through and do what I need to do.

He grips the cushion of the couch. His legs flail and tense. The head of his cock is bigger than ever. His breathing becomes labored, syncopated, and then it stops.

That’s when I felt the first gush hit my tongue. Even though I was expecting it, I wasn’t exactly ready for it. Another pump, and then another. I worry I won’t be able to hold it all.

He gives a big exhale, and that’s when I know he’s spent. I hold his dick and his cum in my mouth a bit, not exactly sure what to do next. I suck a bit more to pull out any remaining drops, then take him out of my mouth.

The jizz is warmer than I expected it to be, saltier too, but it doesn’t taste bad. It’s my reward. A token of my accomplishment. I just sucked my first real dick, and it was everything I hoped it would be.

I gulp down the load, smiling gratefully like any good little slut would.

“Good job.” He says, patting me on the head like I’m a well-behaved puppy. “Now run along…”

That’s it. He doesn’t say anything else. Just pulls up his pants, zips them back up, grabs the remote, and resumes the Hockey game.

A little disheveled, I wipe the slobber from my mouth, get up, and head out of the room like a discarded toy. What did I expect to happen? For us to cuddle and whisper sweet nothings into each other’s ear? I don’t even think I would want that. But to be thrown away like that makes me feel…used.

Then I remember the wet, sticky stain in my pants. A reminder that I enjoyed myself, a lot.

So I guess it’s no surprise that when I got back to my room, I shut the door, locked it, and started enjoying myself two more times…

To Be Continued

~~Click HERE to go see Chapter 3!~~

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