Caught by the Drawer Pt. 03

There I was, standing in front of Jack, covered in the man's ejaculate, helpless to my situation. With my thong and pantyhose gone, all that remained was my red dress, my blonde wig, and whatever make-up that had made it this far. Even in the dim light of the lamp on his bed-side table, I can't imagine I was a particularly appealing sight. Even so, Jack was undeterred.

Without saying a word, he lifted me off my feet and onto his bed, like a parent might easily lift their young child and place them somewhere for safe-keeping. Even at 5'9" and 150 pounds, this man was able to move me complete ease. I sat there for a moment wondering to myself if I even had a decision in this matter at all.

Jack looked at me and smiled, something between reassuring and deviant, before turning away to look at his desk on the opposite side of the room. He adjusted his open laptop screen ever so slightly before reaching into one of the drawers to collect what I assume must have been some kind of lubricant.

As I sat there in a daze, I couldn't help but feel somewhat sad at the way things were playing out. I had always wondered if the day might come where I would summon the courage to explore my bi-curiosity, but I never imagined it would be something like this. I'm not sure what I was hoping for, but perhaps something more casual and not, "You let me fuck you in the ass or else I'll tell your girlfriend you're a sissy?" I guess I didn't feel like that would have been asking too much.

The situation was bettered by the fact that Jack was a decent looking guy. I hadn't spent a lot of time in my life assessing guys by their looks, but I could understand why the girls liked him. Apart from Jack's large frame and the fact that he was in incredible shape with a very respectable cock, he had thick, dark brown hair, with soft hazel eyes. His face was that of a man who was a few years older than what he really was, sun-kissed, and seemingly always sporting a 5 o'clock shadow. It wasn't my thing, but I understood the appeal.

Jack turned back to me and hopped up on the bed next to me before turning my body with his hands and giving me a nudge so that I was now on all fours. My ass was up in the air, with my dress barely covering my dangling penis and timid asshole. Whereas earlier my clitty had been rock hard in the excitement of the moment, it was now simply hanging there, my mind far too anxious to feel any enjoyment.

Now hovering behind me, Jack slowly lifted the bottom of my dress up over my hips, completely revealing my full ass to him. The slut in me was grateful I had taken the time to make sure I was completely shaven that morning; my remaining masculinity wondered if perhaps less attention to hygiene might have made Jack change his mind.

With his hands now resting on both of my hips, Jack said quietly, as if to himself, "This is perfect". I couldn't bring myself to look back at him, but I had to believe he was committed to proceeding.

This was my last moment to back out. Of course, the cat was already very much out of the bag, but that didn't mean I had to let this man do this to me either. I began to speak up.

"Jack, wait-"

But I stopped because something I never would have imagined happened. I was silenced by the sensation of a warm, wet tongue plunging into my asshole. Slow, deliberate, deep licks, carefully exploring my hole. It was something I'd never experienced before, and it froze my mind entirely.

I never would have expected Jack to be a guy who was much for foreplay, nor would I have ever anticipated him to lick another man's asshole, (granted, we're using that term "man" loosely here).

My body began to relax, and I found myself arching my back ever so slightly as if to lean into his licks. I felt submissive and exposed, but surprisingly safe too.

Then Jack showed me another trick up his sleeve. While his tongue licking in and around my wet hole, he began to gradually pull on my cock as it hung between my legs. He quickly found a perfect rhythm between his tongue and his hand, as they each began to work faster, but neither one outracing the other. In a way, I felt like I was being milked by this man, but the sensation was incredible.

How did Jack know how to do this? Had he done this before? Even in this newfound sense of sexual excitement, my mind was still racing with questions.

"Jack..." my voice soft, "how you know-?"

He cut me off.

"I had an ex-girlfriend that showed me this once. Feels pretty good right?" he asked knowingly.

"Yeah...it does." I replied, honestly.

With that, he stopped, and for a second I found myself disappointed that things had come to a halt. My clitty was once again hard, and had resumed dribbling pre-cum, but this time onto Jack's mattress. No matter how this night ended, I was going to need to make sure I went back to my room to let myself cum. The sexual frustration was starting to become unbearable.

I heard the lid of what must have been the lube "pop" open, because a moment later I began to feel his thick forefinger graze around my asshole. As much as I had enjoyed the work his tongue had done, I was grateful he was still opting for lube. I granted myself a quick peek back at Jack; his cock was once again rock solid like the rest of him. No matter how much effort he would have put forth with his tongue, I knew I was going to need all the help I could get.

After a moment of circling my hole, he pushed his fore-finger inside.

"Damn," he whispered, "this thing is tight."

With his finger starting to explore inside of me, my mind raced with anticipation. My clitty dripping with excitement, I really felt like a woman in that moment. Jack had taken the time to get me all hot and bothered, and now he was going to fuck me. I hated to admit it, but this was exactly what I had fantasized about so many times before.

After a little more lube and a moment with a 2nd finger (that struggled, but managed to get inside), there was nothing. Until suddenly, there it was, resting on top of my ass. I could feel its weight on me, dense and warm.

"Don't worry, baby," Jack, now leaning forward so he could speak softly into my ear, "I know this might be your first time, but something tells me it's not the first time this little hole has seen something inside it." He gave my ass a firm and controlled smack, before allowing his cock to slowly creep down towards my hole.

Part of me hated that Jack could read me like a book. Somewhere deep down inside of me, there was still one tiny ounce of masculinity left that felt offended that he could say these things about me, and so confidently. He made it sound like I walked around begging for an opportunity to be fucked. Because I wasn't!

But I wasn't going to run away from this opportunity either.

And with a careful push, he inserted the head of his enflamed dick inside of me.

"Oh!" I let out an involuntary cry, biting my lip to stop the subsequent moan that was building inside of me.

He began to lower his weight down onto me, his cock creeping deeper inside. I felt as if my insides were about to explode; I'd never felt so filled in my life and he couldn't have been any more than halfway in.

He placed his hands on top of my ass, and began to slowly rock back and forth. The feelings of relaxation I had a moment ago had left entirely, as I was rapidly feeling overwhelmed by the thick penis trying to embed itself inside of me.

"See?" he said slowly, "This isn't so bad." his gentle thrusts gradually settling into a smooth and slow pace.

But it was. I felt like I was being stretched to a place where I would never return. And with each small thrust, he was getting deeper and deeper inside. I desperately wanted to touch my clitty in the hopes that it would remind me that this was supposed to be pleasure and not pain, but I knew that if I made myself cum, then I would really be in hell.

Without missing a thrust, Jack said calmly, "It will help if you don't hold your breath, you know?"

Desperate for anything to improve the situation, I tried to take a deep breath, but my exhale was replaced with a long, soft, feminine moan.

"There you go, baby", Jack said, a hint of pride in his voice, "just let yourself enjoy it!"

I was horrified at the sound I had just made, but I realized that with it had come a small sense of relief. I took another breath, this time determined to hide any sense of pleasure but I couldn't-

"Oooooh fuck, Jack, ooooooohhhhh......." I let out as the breath left my body.

"Yeah! There you go!" Jack spoke back, almost laughing at how easily he'd broken my sissy mind and body.

I was ashamed at how I couldn't stop the involuntary submission to this man, but grateful that the pain was beginning to subside.

Motivated by me helpless moans, Jack picked up his rhythm. In a matter of thrusts, he would be near balls-deep inside of me. He moved his hands from the top of my ass to my waist, and now he was really able to pull my ass onto his cock.

A terrible thought crossed my mind: He just came on my face 15 minutes ago. How long will he last the second time?

My body was not going to be able to take 30 minutes, an hour, or whatever it was going to be before Jack decided he was satisfied. With each minute that went by, he became more and more animalistic.

Without warning, my head yanked back, as Jack had grabbed my blonde wig in an effort to gain even more leverage on my quivering body.

"Dude, stop! You're going to mess up my wig!" I cried at him.

"Oh right, sorry!" he said, sheepishly, "My bad dude...it's just, from back here, you look just like a chick. A really, really hot chick."

My entire body burned with the compliment.

"Well, thanks, but...don't do that", I replied, flustered.

He began to slowly resume his thrusts as I turned my attention back to my predicament. I needed to make this man or else I might never walk again.

I had never been in this situation before, so I started with one of the most basic things I knew to do: I arched my back and tried to stick my ass up as much as I could. Jack responded with even more vigorous thrusts, the strides of his cock growing longer, his hips pulling him nearly the entire way out of me, and then returning to flush with my ass. I caught a glimpse of myself in the blank black screen of his open laptop; face down, ass up, getting railed by this muscular man. It was a sissy dream.

At this point, his pelvis was ramming into my ass every time, and a dominant grunt accompanied it. The moans coming out of my mouth were becoming breathless cries of pleasure, and the pre-cum was a constant stream escaping my clitty. I tried to squeeze every muscle I could recruit in my ass, hoping that it might be enough added pressure on his rock-hard cock to make him burst.

With that added resistance, his cock seemed to grow even more, and suddenly a heat formed inside of me; he was hitting the spot. I wasn't going to make him cum; he was going to make ME cum!

A new form of panic set in; this man was about to make me his bitch all by himself and there was absolutely nothing I could do about it. One of his hands left my hips and instead reached for my throat, his cock pounding inside of me. There was no getting out of this; he was going to make me his own.

"Fuck yeah, baby", Jack said confidently, seemingly aware of what was about to transpire, "I love how you love my cock you little sissy."

I was summoning every last bit of strength to avoid cumming when I felt his hot load flood inside of me. His dick pulsing with his thrusts, I had no other choice: I let myself explode, my clitty flailing all over the place with each burst of my own semen. My entire body convulsed as he held me tight, not letting a single drop of his own seed escape my no-longer virgin hole. My cock sprayed its long over-due load, splashing all over his bed, and his floor, and my own face. Eventually, both of our bodies came to rest, his arms and body wrapped around me, his cock still fully buried inside of me, my hole still too stuffed by his penis to allow any of the deposited cum to escape.

***********

Later that night I stood in front of the vanity mirror, trying to scrub the last little bit of dried mascara away from my cheek. Jack walked by on his way to the kitchen from his room and gave me a playful pat on the ass. I gave him a playful moan back and he rolled his eyes. He'd kept his word and as soon as we'd gotten cleaned up, he gave me his phone to delete the picture. I figured there was no way he'd want the word to get out that he'd fucked a guy, so without his photo, we were all square. I wouldn't even need to clean the apartment! Turns out it wasn't such a bad Saturday night after all.

I was exhausted though, so as soon as I got my last bit of make-up off, I went to my bedroom and turned off the light. Who knew being a sissy was such hard work?

A half hour later, Jack hopped up from the couch in the living room and headed for his own room. With his door closed, he sat down to his laptop resting on his desk. With a few taps of the brightness button, his screen illuminated from its prior "black and blank state" and he was thrilled with what was waiting for him: The webcam had worked perfectly, and the recording he had started a couple hours prior was still humming along accordingly. He ended the filming and happily began to skip through the video, pausing periodically to admire his work. His favorite moment was when that stupid little sissy looked straight at the camera, completely oblivious to her own star performance.

Jack closed his laptop and smiled to himself. His girlfriend may have ended things because she didn't want to do long-distance anymore, but now he had himself his own sissy right next door.