Pushing the Limit

My mouth fell open at the next message that popped into my screen.

He told me. Your a sissy whore that loves cock. i think i got what your lookin for. Just wondering if you want to have a good time.

I gawked at the screen. I knew for a fact that Peter wouldn't call me that. At least, I thought I did. He was always so polite and nervous. I couldn't imagine him calling me a sissy or a whore. I'd never been called that. I should have hated it. Seeing Brent say that in a text made me throb, though. It was rude and abrasive. This felt nothing like Peter, and it scared me a bit.

I liked it.

I hesitated. Brent was basically coming around to asking for a meet-up. I chewed my lip, thinking of all the dangers and all the times I'd been through this exact thing before. Thankfully, I'd only ever wound up with Peter, who was kind and scared himself of being outed or caught by his wife. But... Peter was boring. He'd only ever shown any control or passion today, when he'd grabbed me by the hair of the head and face fucked me.

I was hard. The panties could only do so much to hold my arousal in. I read the last message over and over, my eyes repeatedly pausing over that phrase, "sissy whore."

I gulped back the last of the wine in my glass and set it down on the coffee table. I reclined on my couch and slid my free hand into my jogging pants. My little cock strained in its lacy prison, and I caressed the swollen shape to feel the silky patterns in the lace on my engorged flesh. I bit my lip, wondering just how to proceed. It was my turn to be scared, nervous, and timid.

I blew out a long breath and tried to relax. My thumbs typed away at the screen.

I don't have a good time with just anyone. Gotta know I'm in good hands and I like what I see.

I was trying to be careful, even though I knew that was a shot in the dark. Maybe I wanted Brent to reassure me, or console me, to let me know he wasn't a creep or that he wouldn't ghost me. I wasn't sure what I expected, but the message feed shifted up to make room for what came next, as a little wheel spun on the screen where the text would appear. Except it wasn't a text. A large picture filled the screen, fully detailed and in beautiful resolution. I gawked at my phone and the image that appeared.

Brent had sent me a picture of his dick, and it hurt me to even look at the thing.

I could tell from the picture that he was sitting in a recliner in a well lit room, probably his living room. He'd opened his pants or shorts to pull this thing out, and it filled most of the picture. With one hand, he pinched the heap of flesh at the shaft to lift it. I couldn't believe what I was looking at. Brent's cock almost looked fake, but I could clearly see this picture was an authentic shot he'd just snapped sitting in his chair. His other hand clutched a can of beer, and it only made my eyes grow wider.

Brent's cock was huge. The thing looked like a big chubby tube of flesh, sagging just to the left over the hand that held it. It wasn't even fully erect, and I knew for a fact that it dwarfed my own dick in both girth and length. My eyes kept darting from his hand, to the shaft, to the beer can sitting on his thigh just to the right. The skin gleamed in the light, and I could see so much detail in the picture of each patterned line and imperfection. I saw the bulge of a big blueish vein about midway up the shaft, and streaks of tinier veins that spider webbed their way faintly across the flesh.

It wasn't the giant horse cocks I knew from porn. But it was real, right there in Brent's hand, and it was the biggest I'd ever seen. I was so used to Peter's pretty, perfect penis that seeing this fat swell of flesh felt so perverse and nasty. Brent's dick was manly, crooked, and meaty. Full black curls of hair engulfed the base of the shaft, and tangles of the mat of hair even crawled their way a few inches up the cock. I couldn't see much of the head, as the thing wasn't fully erect and bent slightly away from the screen. What I could make out was a dark pink knob of flesh, not even fully swollen into form.

I grabbed my own pitiful dick and squeezed it through my panties. There was no way this thing was real. Guys had sent me dick pics before, but none like this. I shifted on the couch for some reason, my ass sliding on the cushions beneath me and my thighs gliding across one another. My breathing grew shallow. I immediately wished that this big nasty piece of man had been the one in front of my face earlier that day.

A deep part of me tried to pull me away. Tiny little masculine thoughts tried to warn me that this was a guy, a manly guy, with a nasty hairy dick and that I shouldn't be staring at this thinking perverse thoughts. It was wrong and dirty. There was no way I could pry my eyes away from the screen. I rubbed at the lacy bulge in my pants and writhed on my couch, intoxicated by the sight of something so forbidden.

You like it

The message that slid under that picture bumped the feed up on my screen, and for just a few seconds dragged me back into reality. I realized it had been several minutes since I'd received the picture and hadn't even thought of responding. All I could think to do was send a few emojis back to Brent, little smiley faces with hearts and stars in their eyes. I slid the message feed down to stare at the cock again. Was I really talking to the person that owned that thing?

Another message from Brent popped up on the screen.

i dont meet up with just anyone either baby. Are you as cute as Peter says you are

I blinked at the message, digesting everything in the few lines of text. I balked at the blunt words, "meet up". That made this real. There was nothing coy or flirty about those words. The guy was looking for a hookup. The guy that was connected to that hunk of dick in the picture wanted me to see it in person. I started trembling at the thought. My every breath grew more and more shallow.

I read the message again, and saw that Brent was also asking for something in return. Now the tables had turned. It felt like I had to meet expectations now, but there was no way I had any picture that measured up to Brent's.

I was normally more cautious. I never sent pictures to people so casually, especially not photos of me dressed. Yet there I was, sliding my finger through my photo album on my phone, looking through all the girly selfies I'd collected over the years. I needed something hot, but still tame. I wasn't sending this guy anything explicit. I just needed it to be really good. Something that would make that fat cock of his throb....

I found an old picture I'd taken months ago in my room. In the picture, my hair was straightened, and hung down over part of the left side of my face. My makeup was overkill, dark eyeliner, lipstick, and huge blends of shadow. I couldn't even tell that girl was really Alan. Her little cropped black tank top barely contained the giant silicone breasts, and I'd perfectly edited out the seams of the breastplate I'd worn. I smiled. That was back when I'd first dropped the money on those tits. Little grey shorts were stretched over my ass as I squatted in the floor of my bedroom, with tall black socks reaching my smooth white thighs. If someone were attentive, or zoomed in between my open thighs, one could make out the tiny bulge visible through the little shorts.

It was a perfectly beautiful picture. Hues of color from the LED lights in my room warmed the photo, and it was sexy while leaving so much to the imagination. I smiled wider, biting my bottom lip as I made the decision to send this private part of myself in the message.

I attached the picture to the message thread and typed a short little text below.

Cute enough for ya??

I dropped the phone to my chest and held my palms to my face. I'd sent pictures before, but never this soon to anyone, and never before feeling totally comfortable. The rush was intense. Every second that passed now was full of fear, uncertainty, and hopeful excitement. I kept thinking of that thick penis on my phone. I kept seeing the beer can beside it, and how that cock was only slightly smaller than the can itself. How could it be that big? How could he be texting me? A crossdresser? Wanting to meet up and... more?

Brent wanted a sissy. That wasn't like Peter. Peter wanted a blowjob. Brent probably wanted a whore to fuck. I chewed my lip and rubbed myself, wondering what it would be like to be that whore for a man, a real man. I hoped I was girly enough. I passed for Peter. I wanted to pass well enough for Brent and that hairy dick of his. Just thinking about it made me feel even more girly.

My phone vibrated on my chest, and I nearly flung it into the floor when I fumbled for it. The screen shook in my hand as I read the new message on the screen.

Holy shit girl!! You are NOT cute you are FUCKING HOTTT

I could have melted and slid right into the couch cushions. My cheeks grew hot and my hand rubbed my painful little erection faster. My chest was actually hurting from the beating of my heart. I frantically thought of what to say to Brent next. Arousal had seeped into every crevice in my brain. Caution and fear were gone. I didn't care anymore. I wanted to meet this guy. I wanted to be dressed like a girl in front of him and watch his eyes look me up and down. I wanted to know that fat dick was filling full of blood while he looked at me.

As if Brent were thinking the same thing, he sent me another message. It was another picture. This time, he wasn't clutching a beer can, he was only holding his cock. I actually let out a whimper when I saw the image. One of Brent's fists was holding the thing, though it could have stood on its own.

Brent was hard now, and looked like he was stroking. The fat red head of his dick and the oddly wrinkled skin beneath it were now fully visible. I had to take a breath and steady myself in order to hold the phone still. A deep orgasmic burn had already formed in my lower body. I had to stop rubbing myself. Beholding that meaty manly cock could have pushed me over the edge.

I read the text that followed.

Look what you did baby

I smiled. Right then I knew I had to see him. I wanted to meet Brent and let him see Alison. I felt so stupid and ditzy for being hooked by a dick pic, but that couldn't have made me feel more like a slutty girl. I just couldn't believe I was staring at a real person's cock in that picture. I imagined seeing it right in front of me the way I'd been with Peter. I wanted that. Even if it was risky, even if this guy wasn't safe like Peter. I wanted Brent.

My thumbs hovered above the screen for a few seconds, contemplating what I was about to set in motion. Ultimately, Alison took over and I sent the message.

Wow. Looks like I found my new favorite toy! When do I get to play with it?

Brent was quick to message back. The reply startled me.

Tonight if you want. You can come by my house.

Even though I was high with arousal, a stab of fearful reality went through my heart. This was real. It was happening if I wanted it to. I'd meet Brent. I'd see that huge cock that I'd seen in the picture. Chewing my lip, I studied the pictures again. I wondered if I was that daring. The thrill was enticing.

I sent a message back.

Tomorrow night is better. More time to play with me. Send me your address.

****

Everything was great until that exact moment. I was sitting in my car, staring straight ahead out through the windshield at the house I'd pulled up to, at the car that I was parked behind in the driveway. I hadn't even bothered to kill the engine. My body had turned to ice, unable to remove my hands from the steering wheel or peel my eyes from the vehicle directly ahead of me.

Of course I'd been through this before. The moment was here. I was dressed to kill. My masculine self was tucked away behind the soft veneer of my new self. My makeup was perfect. The dress was to die for. All I had to do was follow through. I'd grown used to that. I'd been stood up so many times that I'd become numb to this. This was new, though.

There was a cop car parked in the drive.

I tried to make sense of it, but no other explanation fit. Peter never mentioned this. Brent was clearly a cop. Right? It couldn't have been one of his relatives... his kids were grown but... it had to be his?

A million similar thoughts raced in my head as I stared blankly at the squad car. Several times, I almost pulled the shifter into reverse and backed out of the driveway. I remained petrified, sifting through all of the horrible outcomes that my imagination could conjure up. I thought of the embarrassment of being hauled to jail, a tranny whore that all the guys would be laughing at down at booking. I thought of curling in a corner of some cold seedy cell awaiting my fate for... solicitation, or whatever they charged for this.

A fucking cop car. Had Peter known? Was this some fucked up setup to be rid of me?

I closed my eyes and let out a long slow breath, feeling the heavy shadow on my eyelids and the blanket of ink on my eyelashes. I allowed my body to relax in the seat, my rational mind falling back into place. This was not a crime. And why would it be so obvious if they were trying to set me up? A squad car in the driveway of the house I was called to?

I killed the engine. It was a big step. For a time, my headlights illuminated the squad car until they went off, affording me the additional time to reconcile my inhibitions.

So, Brent was a cop. That wasn't so strange. I felt my pulse returning somewhat to normal, and I tried to regain my bearings. The whole day had been such an unnerving slog. I'd wiped my face clean at least a dozen times in the effort to perfect my makeup. I'd changed clothes so many fucking times and never felt hot enough. I'd distracted myself with the loudest music I could on the drive over. I was here. It was my last chance to back out. I thought of the times I'd waited in motel rooms, for some disgusting ghost of a man that never showed, or the promise of a guy that was too hot to be real. I could drive away, but I'd be no better than any of those would be hookups.

I didn't need to pull out my phone to see that fat dick in my mind. I shuddered just from the thought of that thing. I was in the man's driveway. Cop or not, I was here and I wanted it so badly. I had to know if it was real. Jesus... I didn't even know what he looked like! I'd agreed to meet a stranger based on a dick pic, and he could be a slobbering fool, or a creepy old guy. My inner lust tumbled with my shame and disgust for what I was doing.

I steeled myself, and switched on the interior lights in my car. The darkness outside the vehicle disappeared. I pulled down the visor above my head and stared at the girl in the little mirror there, the same way I'd stared at her a hundred times earlier. I ran a finger down the single streak of red coloring I'd put in my hair this morning. Those big feminine eyes stared back at me, daring me to find even the smallest flaw in my makeup. There were none. I knew this to be true. I distantly wondered, not if I were pretty enough like I usually did, but if she looked enough like a whore. The idea excited me. I dabbed at the dark red lipstick on my lips, making sure that none rubbed off on my pinky finger. It wasn't supposed to.

I flipped the mirror away and found my purse in the passenger seat beside me. With shaking fingers, I unzipped the little pouch and rummaged through its contents. My lipstick was there. I grabbed my perfume and sprayed myself a couple more times around my neck. The three condoms were still there in the purse, right beside the bottle of pepper spray. For a moment I stared at the items in disbelief, trying to wrap my head around the whole situation. Was I really here, dressed and willing to use... all that? Horrible scenarios chewed at my mind as I wondered if the pepper spray would be enough....

I shook my head and zipped the purse up. Switching off the lights, I opened the door and stepped out into the late evening air. I shut the door behind me and wondered if that sound alone told of my arrival. I glanced around, wary of my surroundings. Pete lived in a subdivision, full of soccer moms and retirees. The place I'd come to was near the end of an old country lane, and while there were neighbors, they were thousands of feet from Brent's place. Terrible thoughts of fleeing across massive open yards flanked by trees swarmed my mind, and I had to rein in my mind once again. This wasn't a horror movie. I'd be fine. The worst that could happen was embarrassment.

I pulled down at the black dress I wore, which hugged my body in a way that was somehow tight but so comfortable. Even as my fingers felt of the soft material, I wanted to roll my eyes into my head in ecstasy. How a material could feel this light and be so taut around my body seemed like magic. I felt so sexy, almost like I wasn't really wearing anything at all. I hoped Brent would think so, too. I attempted to pull the dress down my hips far enough to hide the bottom of my ass, but a dirty little part of me knew that the dress would inevitably ride back up my thighs. I slung the purse over my shoulder and set my sights for the front stoop.

My heels clicked on pavement as I made my way toward the front door. In the black evening dress, my body felt lithe and feminine, and the nighttime air kissed what skin I left exposed. I felt the faux silicone tits bounce in my bra, as did my ass cheeks that were perched high atop my legs by the heels I wore. My breath fell through quivering lips as I stepped across the stone sidewalk toward the house. Though I knew no neighbors were close enough to witness, I played my part, swaying my hips slightly and creeping up the walk like a cat.

I couldn't help but glance down at my body as a security light illuminated me on the front stoop. I tried to fully become the female that crept up to the door in heels and a tight dress, while my mind screamed at me, urging me to run back to my car and drive away.

I stood before the door and smoothed the soft, silky fabric of my dress down my body once more, pulling at the hem to slide it down my thighs. The doorbell was right there. A man was inside this house. I pictured his fat cock in my mind.

I was careful not to chip my nail as I pressed the button to ring the doorbell.

It was done.

I waited in agony, wondering what the night would bring. I lamented over my choice of wardrobe. Did I look like a hooker? Did I look desperate? Classy? Would he like his sissy whore?

I strained my ears to listen for sounds of movement in the house. The lights were on inside. There didn't seem to be any other signs of life. I stood waiting for what seemed like an eon on the front porch, illuminated by the security lights. I felt so exposed again. A million doubts surged back into my mind again, but I urged myself to stand still. The moment was almost here. I needed to be ready. I couldn't be Alan. I couldn't be so timid and feeble.

Just as I was debating with myself about pushing the doorbell again, I heard muffled steps and the door clicked, then swung open.

Brent stood in the doorway of his house, and the reveal crashed upon me in a wave.

A tall, broad, balding man with a mustache greeted me in the threshold, and I felt so exposed before his gaze as his eyes darted up and down my body. I froze, and immediately felt like prey before his scrutinizing eyes. In that instant, I was just another guy in drag, waiting for this strange man's judgement, hoping I didn't just look like a pitiful loser desperate for a hookup.

Brent's thick mustache pushed upward on both sides as he grinned, though his jowls still drooped as he admired me.