Caught by the Drawer Pt. 02

When I got to Jack's door, I raised my hand to knock, but stopped. I couldn't go into this without a plan. Jack had all the cards right now, and that wasn't going to change if I acted like the brain-dead bimbo I looked like standing there in the hallway. I had to think of some kind of deal that would provide me an opportunity to level the playing field.

I couldn't just pay Jack off, because what would stop him from asking for more money down the road? I suppose I could have offered to take care of some of his class assignments, (the guy wasn't exactly in the world's most advanced classes for his sports communication degree), but my plate was already pretty full with my engineering homework. And there was no way I was going to be able to take tests for him when that time came.

Offering to clean the apartment was the way to go. That would give me regular access to his room and if he caught me snooping, I could just say I was just trying to be diligent. There had to be something in there that he wouldn't want people to find out about, and as much as I didn't want to be some kind of nark, I also didn't want anyone to know about Meaghan either.

My mind started to drift towards the thought of prancing around as our little apartment maid, (I'd read some smut about that sort of thing, it was always a winner in my book), but there was no way I was letting Jack see this side of me again. For him, and the rest of the world, Meaghan was a one-time experience.

As I went to knock again, Jack's door opened, but only enough for him to poke his head out into the hallway.

"You see, how it works is: You turn the knob and the door opens." he jeered at me, back in his teasing mood as he gave me another look up and down, "I could see those heels outside my door for a couple minutes now, thought you might have forgotten how to knock."

In as calm and collected of a voice as I could manage, I replied, "I have an idea for an arrangement."

"Perfect!" he exclaimed, "I do too, but let's hear yours first. Come on in!"

He pulled his head back inside his room, leaving the door cracked behind him for me to follow.

I took one last breath, and pushed his door open, starting to state my case as I entered-

"Look man, this whole things is just -- JACK! What is the MATTER with YOU?"

I know that I had been going for the bimbo look, but I may have been too committed to it.

I had opened the door to Jack, leaning against his bed. 6'3", 215 pounds of pure muscle, completely nude, with a fully exposed cock reaching 7 inches down his thigh. A single light, a lamp sitting on his bedside table, cast shadows across his vascular arms and thick legs. He didn't say anything; he just stood there looking back at me with his hands resting by his sides on the mattress.

Every part of my being wanted to turn and rush right back out the door, but I couldn't feel my legs.

"Dude, I told you, it's not like that, this is not like that!" I insisted, my eyes desperately scanning the room, but not looking for something to incriminate Jack, just looking for anything that might distract me from the cock that seemed to be staring at me.

"Isn't it though?" he asked, pointing at me, specifically at the bump at the bottom of my dress that was now unmistakable. My cock, (could I even call it that, especially in comparison to the other thing in the room?), had escaped its tucked position and was now pointing upwards and outwards, not out from under my dress, but propping it into a position that left no doubts as to what was going on.

"Listen," Jack began to mansplain to me, "we both know what this is. You're a sissy. It's fine! There's nothing to be ashamed of," his voice was making an attempt to be sincere, but he was still clearly amused at the circumstances, "and I don't know too much about sissies, but I know one thing: They love to suck dick and they love a good cock in their ass. I think either of those sounds great to me right now, so which is it going to be?"

My stupid penis, a "clitty", in comparison to what Jack had at his disposal, had betrayed me. I never should have come into his room still dressed up. I could have waited until the next day to have this conversation, a time when my head was on straight (pun intended). But seeing Jack and the thought of humoring a cock like this, it was almost enough to convince me that maybe my sissy-side wasn't just a hobby.

I had to get it together.

"If I do this...this stays between us? You don't tell my girlfriend? About this, or the dressing up?" I asked.

I was doing a bad job of getting it together.

"Absolutely," Jack replied, "I don't need the guys on the football team knowing I fucked around with some sissy on the side."

I hadn't even thought about them. I suppose that made sense; they'd probably think it was gay for him to have another guy suck his dick. Although, it would be hard to say I was much of a guy in that moment. If I had a blonde with big tits taking my cock down her throat, I probably wouldn't feel very gay about it. But as the guy with a cock in his mouth...it felt like it would still be pretty gay for me.

"So...we doing this?" he asked as he lowered his head, trying to catch my eyes to see what I was thinking as I stared off into space.

Feeling confused about my sexuality, my identity, and how I had gotten into this situation, I was still very certain about one thing: I sure as hell was not about to spread my legs for that thing between his. Don't get me wrong, my ass had seen a dildo a time or two before, but it was never attached to a football player in the best shape of his life. I had practiced sucking on a dildo, and while I privately took pride in my recently discovered ability to deepthroat a rubber penis, I always ended up feeling ridiculous trying to sexually satisfy a toy.

And what about my girlfriend Alyssa? Obviously, this was cheating on her, albeit not by my own choosing. If I didn't do this, Jack would tell her and everyone else who would listen that I spent my spare time as a sissy whenever I could. There wouldn't be any relationship to salvage anyway, so what choice did I have?

In that moment, I realized how ridiculous I sounded. At any moment I could tell Jack to "Fuck off" and walk right out of that room. I could tell Alyssa the truth about my enjoyment of dressing up and see if she could try to understand. I could offer to clean the apartment, and still try to find one of Jack's dirty little secrets lying around. There were a million other ways to handle this situation besides sexually pleasing this man.

But it was clear: I didn't really care about anyone finding out. I just wanted to suck that man's cock.

Even in my heels, I was still looking up at him when I turned and said, "Just stop talking, okay?"

He gave me a big smile and motioned as if he was zipping his lips as I dropped down to my knees.

As I knelt down to the level of his cock, I realized that this thing was even bigger up close. The circumcised beast had veins like its owner's arms. If I didn't know any better, I'd say it liked going to the gym just as much as Jack did.

In my few experiences of receiving blow-jobs, I never found myself too enthused by it. I don't know if it was because the girls didn't know what felt good and what didn't, or if they weren't into it, or whatever it was, but I always ended up telling them to stop so we could have sex another way. I was determined that if I ever had the opportunity, I would be able to do a better job than they did.

And here was that opportunity.

Starting with a kiss of the head and a lick of the shaft, I began to suck his cock. It felt warm on my tongue, the taste slightly bitter as the first signs of pre-cum began to surface. Mixing in a combination of playing with his balls and jerking off his penis with the head in mouth, I could see the smile that was on Jack's face was now replaced with sexual disbelief.

"There's no fucking chance you haven't done this before you little sissy." he let out with mild exasperation, in between the small grunts that had started to slip out of his lips.

Whatever feelings of embarrassment that I had been holding on to were rapidly starting to dissipate. My own horniness has flooded my mind with excitement and confidence given the small compliment that indicated I might know what I was doing.

I had found a nice rhythm, my head bobbing up and down, going through the things I knew to do, when I decided that I would try to take the shaft down my throat. I had never done that with anything quite this size, but I had gotten pretty comfortable with the toys at my disposal. Part of me felt like that might be a bold move for a virgin cock-sucker, but it also might be my last time in this position, so I figured I shouldn't leave any stone un-turned.

I pulled his cock from my mouth, my hands gliding up and around the thick prick while I took a moment to compose myself. I looked up to see the small smile back on Jack's face, his eyes closed, clearly enjoying himself. With one last breath, I went for it, shoving his cock back inside my mouth and towards my throat. When it reached the back of my tongue, I knew it would be a tight fit, but with a push and a gag, I forced it deep inside me. My nose had just grazed the base of his pelvis when Jack shoved me off of him.

"Bro!" he said, half laughing, half catching his breath, "If you do that, you're going to make me come."

I leaned back, wiping away the bubbly saliva and pre-cum that was spilling out of my mouth. I was fully aware of and embracing my slutty behavior, pleased with the fact that I had made this man admit such a thing.

"Isn't that the point?" I asked coyly.

He looked down at me with a smile as he lifted my chin with the back of his forefinger, "Damn, I knew you were a sissy, but I didn't know you were a FREAK!"

He let his hand drop away as I went back to work, somehow even more motivated than I had been a moment prior. A "freak" he called me! That was a term I'd only heard thrown around with the most intrepid lovers. To be called such a thing by this man who was desired by countless women at our school made my entire body feel like it was on fire.

This time I managed to slip his cock down my throat with minimal struggle, and I began to move my head back and forth, slowly allowing the head of his penis to reach deeper and down into my chest. I wanted to move as fast as I could, but I knew that I was one mis-step away from choking and ruining the whole thing.

As if a warning for the eruption to come, I could feel the first pulse of his cock inside my mouth. And then another. Jack's hips began to slowly sway back and forth, culminating with a small thrust at the end of each motion. The small grunts he'd been letting out earlier were becoming both more frequent, and more primal.

The energy in the room rose as his member grew thicker and thicker, what little air I had available becoming increasingly scarce. The tears that had been forming in my eyes began to drip down my face, and I could feel my heart begin to beat out of my chest. Just when I thought I should tap out, his hands reached through the blonde strands of my wig to grab the back of my head, ensuring there would be no early escape. He had sensed my hesitation and he had no plans on stopping.

"No quitting on me here, baby," Jack barked at me as his cock reached into my stomach, "you've done so well, can't have you give up now!"

I tried to make a plea for a moment of respite, but all that came out was a muffled groan, my mouth far too gagged to produce anything that might be coherent.

"See, you're fine," he said reassuringly, but completely indifferent to my struggle to breathe. I was nothing more than an object for his sexual pleasure in that moment, which would normally be a titillating thought, but nothing was more appealing to me right then than the premise of oxygen.

His hips were now fully thrusting and I had no way out of the face-fucking. My eyes began to roll to the back of my head, my mind completely blank and my lungs empty. My hands were now up against his body, trying to push him away, but he would not have it. I was going to be his until he was done.

"Fuck yeah, I love that you little bitch! Try and push me away, like you don't want this. I know you want this cock you hot little whore!" Jack shouted down at me.

I was on the verge of complete panic in my final moments of consciousness when he ripped his cock from me from my mouth. I began to cough, choking on air, as load upon load of his hot semen splashed across my face and down onto my silicone tits. The room felt like it was a thousand degrees, but at least I knew I was still alive, (which for a moment there, I thought might not be the case).

Eventually, the loads came to a dribble, and he pulled the still throbbing member away from my face. I sat there on my knees still catching my breath, head down, in awe of the pornographic quantity of cum that had just been sprayed onto me.

"Say cheese!" Jack cheekily instructed from above.

I look up in time to see the flash of an iPhone from directly overhead, pointed down at my cum-ridden face.

"You DID NOT just DO THAT!" I bolted to my feet, snapped out of my face-fucked daze, suddenly filled with rage. I snatched for his phone, but he used one of his large paws to stiff arm me away.

"I cannot believe you! We had a deal!" I cried at him, now punching on his chest and shoulder, summoning what remaining strength I had available. Jack was unbothered as he admired his photography via an outstretched arm.

"Oh relax," he said dismissively, "just a little souvenir from our first time together. You look great!"

He turned the phone to me, keeping it a safe distance away, so I could see for myself.

There I was. Wig, disheveled, but still on. Mascara running down my face. My red lip stick losing its "zing" after being drowned in my own spit and his pre-cum. One of my tits had escaped my red dress and was in full view. And cum, everywhere. All across my face, into my hair, and down on my tits. Did I look great? No. But did I look like one of those little slutty whores you'd see in porn? Very much so.

"You have to delete that photo," I pleaded with him, "Please. I can't have that out there."

Jack looked at the photo and then back to me, before closing his phone and setting it on his desk next to his laptop.

"Look dude. I know you're mad. And I know I said you could pick between sucking my dick or getting fucked, but I really just want to pound that ass of yours. I see you squat in the gym. I know those joggers that you wear in there aren't for men. You've been sculpting that ass, and I want in it," he explained, while reaching around me to give me a tap on the butt.

I should have been irate at such a request, and I should have smacked away his lingering hand, but I felt helpless and dejected as I stood there in his room. I looked around, remembering that the whole reason I was there was to find some dirt on him. For a guy that had to divide his time between the football team and class, it was awfully clean. A couple books on the floor and a sock that hadn't made it to the hamper. Offering to clean the apartment was probably never going to fly anyway.

"I sucked your dick...we had a deal..." I repeated, my head hanging, my mind fully aware of another man's cum beginning to dry all over my body. Whatever pride I may have felt in my ability to make this man orgasm had departed with the knowledge that there was now tangible evidence of the fact that I was a sissy whore.

"We had a deal, but now we can have a new deal!" Jack retorted, as if he was providing me with good news, "If you let me fuck that ass ONE time, I'll let you delete the photo. I swear."

I looked up at his face and back down to his cock. Despite the seemingly gallon of cum he had just delivered, his penis still looked just as solid as it had when I came in the door 20 minutes ago.

"Besides," he continued, "it looks like you could use a little more fun too," pointing down the puddle of pre-cum that had formed on the floor beneath my steadily leaking clitty.

This was it. I could walk out of the door, knowing that this man had a social life ending photo of me at his disposal, or I could hope that he would make good on his promise that I could delete that photo if I just gave him my ass this one time. Earlier, I had been lying to myself about not having a choice as to what to do. Right then, it felt like there really was only one option.

With a hopeless sigh, I bent down to pull my pantyhose away from my legs, followed by my thong. Jack took a step back to give me space, rubbing his hands together like some sort of cartoon villain that was getting his way.

With my panties off, I clasped my hands to my side and pathetically asked, "Where do you want me?"