Caught in Pink: A Sissy Story

1

It all started because of my stupid tattoos. First, I should probably explain that in my everyday life I'm a tall masculine man with a very blue-collar job. I work with people who throw the words "cocksucker" and "faggot" into every other sentence, and while I don't stoop down to their level so that I can seem like one of them, I don't correct them either. Little do they know, outside of work my sexuality goes to places FAR beyond those little words, and while I know they can (and do) tolerate working alongside men who are openly gay, knowing what I do in my private time would make it impossible for them to respect me ever again.

Ever since I was a teenager, I have been turned on by dressing up in lingerie. Silk, satin, fishnets . . . and a few years ago I tried adding a wig and makeup and quickly became obsessed. I feel beautiful as a woman, and over time I began to form a completely separate personality when I was dressed. Shy but flirty, submissive and pliable, and sexually charged far beyond how I'd ever felt as a man. But it wasn't enough just to dress up for my own gratification, I needed people to see me. Specifically, people who couldn't and wouldn't be able to "out" me without calling their own sexuality into question. In other words, married men.

I took hundreds upon hundreds of photographs of myself while dressed. Different outfits, mostly the kind that grow crops of erections in the soil of sex-starved men. Different positions, mostly bent over and presenting my body for breeding, sometimes on my knees with my face painted like a whore and my mouth open . . . and sometimes, tied up or restrained in ways that would leave me totally defenseless against their hard cocks, no conversation required. And, in the grand scheme of things, that's what most men really want regardless of what they say to the contrary. It's how we're WIRED. Deep down in the darkest part of our souls, that's what men fantasize about when we see someone we desire but can't have. Though it may only last a fraction of a millisecond, like the taking of a photograph, an image is produced in our dirty little minds of grabbing the hot little cashier at the drug store by the back of the neck and ravaging her for our exclusive pleasure. And that's what I kept in mind when I posted pictures of myself while feminized.

The results were startling to say the least. The amount of attention in brought to me was overwhelming as were the offers I began to receive from men who desired me.

After a few years, posting pics and chatting wasn't enough to satisfy my urges any longer, so I began inviting those sex-starved souls into my life and doing all the things their wives wouldn't, often on video which I would then post on the internet for other sex-starved men to jerk off to. I was never really worried about anyone in my straight life ever seeing them and/or recognizing me, but I went out of my way to keep the tattoos on my arms covered just the same. While my face would be hard to recognize under all that makeup, my tats would be recognized instantly by anyone who knows me, but after a while I began to think, "What the hell?" they'd have to be on either a gay or transgender website to see them in the first place, and that'd be hard to explain to the boys down at the factory . . . not to mention their wives.

Hindsight is always 20/20, and it simply never occurred to me that I hadn't considered all the possibilities. Specifically . . . what if the co-worker in question was a gay man, for example? He could certainly expose me without anyone thinking different of him. Or . . . what if the co-worker who stumbled upon my profile was a WOMAN? In a culture that views female sexuality (and BI-sexuality) in a way that encourages experimentation, a woman could admit that she was trolling the internet for videos of men fucking other men without permanently damaging people's perception of them, not like it would if a man admitted the same thing.

The rebirth of my sexuality began with a text to my phone from an unknown number. Just a single word at first: Krissy. I've had many partners over the years and I often clear old numbers off my phone if things don't work out with a person or if I haven't heard from them in a while, so I wasn't all that concerned when I saw it. I simply assumed it was someone I had known at some point and they were trying to reconnect. My system, if one existed, was to disregard texts from anyone without a name attached, as it would immediately inform me that I'd chosen to cut that person loose at some point. I didn't need to remember the specifics, just the fact that I'd removed them from my contacts was all I needed to know.

When I didn't respond, they raised the stakes. "I know you."

Chuckling to myself, I said, "Well DUH, how would you get my number otherwise?"

Their answer nearly made me sick . . .

"From the company directory."

I tried to call bullshit but found myself unable to type. I was sure it must be a bluff, yet I found my eyes scanning the company floor for anyone holding a phone in their hand. I counted at least six at that moment, but none of them seemed to be looking in my direction. I decided it must be a very bad joke and I was about to say so when they beat me to it by naming the company I work for, erasing all doubt that this was real. I won't use the name here, instead I'll call it Lakeport Industries.

"Who are you?" I asked, terrified.

They answered, "M."

It was mind boggling. With over four hundred employees, I knew at least a dozen guys named Mike, or Mark, or Manny, or Marcus, or Manpreet, or Mikael, or Mitch . . . and those were just the men I knew personally. And, what if that was the initial of their LAST name rather than their first? Hell, what if it was NEITHER?

"What do you want?"

Their response, "YOU."

"Fine then," I typed frantically, "come talk to me."

Their response didn't come for nearly 20 minutes, but when it did, I realized that I was in real trouble.

"Listen carefully, SLUT. I AM IN CHARGE. Make no mistake about it, I can ruin your life. And before you do anything stupid like taking down your online profiles, don't bother. I've got screenshots of all your pics, and I've downloaded all your vids. You should have tried to cover your tattoos a little better, Krissy. Think the people around you won't recognize you? And before you do anything stupid, any profile you take down I'll put up under another name and send the link to everyone who works here. I'm not looking to ruin your life, so don't make me. Be a good boy and nobody ever needs to know. Understand?"

Unable to say anything else, I answered, "Yes, I understand."

"Good," they said, "I'll be in touch."

For the rest of the week, I searched the dozens of faces around me for the slightest sign of recognition, a sly smile or a grin or a wink. When I failed to see any, my mind began to create them. Did this person just smile at me, did that guy just flirt with me? For just one moment, I thought I had found my suspect in a man named Marc. All he did was say hello to me, but he usually ignored me so it made me wonder. But that theory was blown out of the water when my phone buzzed with a message while he was within my sight and was NOT holding a phone.

"Back to your station, bitch," the message said. "Look in your tool-box."

I hurried back to my station and opened the tool chest. Seeing nothing I lifted the tray to look beneath it and let out an involuntary gasp over what I found. Laying there where anyone could find them was a black butt plug and a pair of red satin panties with a small note pinned to them. The note read: "You have fifteen minutes to send me a pic from the bathroom on the 2nd floor wearing these. Just these, nothing else. I'm WATCHING YOU!"

Again I looked around me, panicked, but then it occurred to me that if this person really was watching me, they'd be going out of their way not to be caught looking. With no other options available to me I shoved the panties and the butt plug into my pocket and pulled my shirt down over them before hustling off the factory floor and upstairs to where all the paper pushers and execs did their business in glass walled boardrooms. This was at 11:30 so they'd all left for their typical 2 hour lunch already. I let myself into the small handicapped washroom and locked the door behind me. My phone buzzed in my pocket.

"5 minutes slut."

I stripped down to my bare feet and stood there, shaking. I looked down at the satin panties in my left hand and the black rubber butt plug in my right. I heard my phone buzz again and without looking at it I knew that my five minutes must be up. I slipped into the panties, and with shaking hands I began working the butt plug into myself. Without lube it didn't go in easily, but there wasn't time to mess around so I pushed it in, grabbed my phone and took a picture of myself from the shoulders down before sending it.

Their response was quick and angry. "THAT'S NOT WHAT I ASKED FOR."

"What do you want me do do?" I asked.

"Get on your knees and open your mouth like you're sucking cock."

Still shaking, I dropped to my knees on the cold tile floor and took a pic of me looking up at the camera with my mouth open.

"That's better," they said. "Now show me the plug in your ass."

I set the camera down on the sink pulled the panties over to one side and took a shot.

After a moment, they replied, and I realized I'd just made my situation even worse. "That's good slut. Now I've got pictures of you taken on company property, guess you didn't think about that, did ya slut?"

"No, I guess I didn't. What do you want from me, why are you doing this?"

They responded with a laughing emoji followed by, "What I want is for you to do exactly what I tell you from now on. As for why, that's easy. Because I CAN."

Not knowing how to respond, I stood there looking down at my phone dumbly until they messaged again, "Back to work, slut. Don't even think about taking that plug out or taking those panties off."

I did exactly as I was told and returned to work. I spent the rest of the day waiting and wondering if or when they would come to me and make themselves known. They never did.

Later that night I was sitting alone in my apartment when they messaged me again. I hadn't eaten a thing all night, and I just sat there staring at the blank tv screen, wondering how I had gotten myself into this mess. A picture from one of my online profiles appeared on my phone. One of my many "naughty schoolgirl" looks. Pleated skirt, stiletto heels, fishnets, bright red lipstick and my eyes painted dark and sultry. "One hour", the message said.

With my heart pounding, I typed back, "What happens in an hour?"

They replied, "Your date will be arriving."

"My DATE?!?"

"That's right slut. Tick tock, better get your ass moving."

"Wait a minute!" I typed as fast as my thumbs could manage. "Is it YOU?!? Are YOU my date?"

They replied with yet another laughing emoji. "Not this time, Krissy."

"WHO then?!?"

They sent a winking emoji, "You'll see."

2

I hurried into my usual prep, my mind pulling me in a thousand different directions as I showered, shaved my body bare, and began trying to apply makeup with a very shaky hand. Several times I actually stopped getting ready, but then reality would come crashing back in within a few seconds and I knew that I had but two choices. Choice #1; tell this mysterious "M" person that they could go fuck themselves and take the chance that they might actually do what they said about sending links to my online profile to everyone we worked with. Or, Choice #2; I could do as I was told, and hope that it would be enough to satisfy the person doing this to me.

I needed more time to think, and that time could only be bought with my co-operation. So, I pushed forward.

I slid into a pair of fishnet stockings and put the black lace panties over top of them (a trick we sluts often use to make for easy access). Next, a black bra, which I then stuffed with my fake rubber breast forms, and then a white dress shirt, which I left open and tied in a knot just above my navel.

I pulled my blonde wig over my head and combed the tangles out of it before taking a step back to see how I looked. Satisfied that I looked just like the picture, I spritzed myself down with perfume and sat down on my sofa to wait for what happened next.

Shortly after my phone buzzed again, and it was "M" letting me know that my date was outside. "Ready, slut?" they asked.

"Yes."

"I'll tell your date to come on in."

I peered out the window but the person approaching my building was nothing more than a dark silhouette. I heard the person come in the front door and descend the stairs, and within a few seconds they were knocking gently at my door. I took a deep breath and opened it, half hoping that I'd recognize the person standing there from work, and that they were indeed the mysterious "M" and that this "date" was with them, not a stranger.

No such luck.

I had no idea who the man at my door was, but he sure as hell knew who I was. His eyes went as wide as saucers and his jaw practically hit the floor. "Oh my GOD!" he exclaimed. "It's really YOU!"

His voice boomed through the lobby like a loudspeaker and I heard the old lady across the hall from me fumbling with the chain on her door so she could open it. I grabbed the man by the arm and yanked him into my apartment and just barely got the door closed as she opened hers. I held a finger to my lips and shushed him into silence until I heard her door close.

"Listen,' I whispered, "you have to be very quiet, okay? My neighbours hear everything."

"I'm sorry, it's just . . . WOW! I can't believe it's really YOU!"

After turning on the tv for some background noise, I led him away from my apartment door in case the old lady was standing there with a glass pressed against her ear. "Who are you? Have we ever met?"

"You and I?!?" he said excitedly, "Hell no! But I've watched all of your videos, probably a hundred times!!"

"My videos?" I said, struggling to comprehend. "Who's M?!? How are you here right now?"

His expression showed me that he was just as confused as I was, "M? I have no idea. I got your message and came right over like you asked!"

"Do you have this message?"

"Um yeah, sure," he said, digging for his phone. "Did I do something wrong?"

Ignoring the question, I watched as he opened his text app and snatched it from his hand. Sure enough, under the name "Krissy" there was a series of messages. I scrolled up to the top and read the conversation from the beginning.

The first message was from the man standing before me, "Hello! Is this really Krissy?"

The response, "Yes it's really me, how are you doing sexy?"

My only thought at that moment was "what the fuck?".

I scrolled down and continued reading.

Krissy: "I see you're a big fan of my videos, especially my blowjob videos, and to show my appreciation I have something special to offer you."

Him: "Really? What's that?"

"How'd you like to make one with me?"

My heart sank as I realized . . . "M" had found this guy through the "likes" and comments attached to my videos and contacted him pretending to be ME, and obviously set up a date with him.

"I just want to say," he said to me nervously, "what an honour it is to meet you in person, and I'm really excited to be here."

I let out an involuntary sigh and tried to smile as I handed his phone back to him. "What's your name?"

"Bob."

"Okay, Bob. I need a few minutes to freshen up. There's cold beer in my fridge, why don't you grab us both one and I'll meet you back on my couch in a few . . ."

He pointed to my couch, "Over there?"

"Yes, Bob," I replied patiently as I collected my phone and headed towards my bathroom. "That's the couch. Meet you there, kay?"

After closing myself up in the bathroom and locking the door, I sent a message to "M".

"What IS this?!? What do you want from me?"

They replied, "I want you to do exactly what I tell you to do. And right now, I want you to give that guy the best blowjob of his life. And . . . I want it on video. Understand, slut?"

"And what then? If I do that will you cut me loose? Leave me alone?"

"Not a chance, Krissy. I'm just getting started with you. Now stop stalling and go take care of your guest. I expect to see the video posted on all your profiles by tomorrow morning."

I rejoined Bob on my couch and saw that he'd already finished his beer. He was also pitching a MASSIVE tent in his pants that made me just a little glad that "M" had only promised him a blowjob and not a hard pounding in my ass. Silly as it sounds, I actually felt a little bad for him; it wasn't his fault that he'd been trapped in this little game, anymore than it was mine. Since there was nothing to be gained from telling him the truth of it all, I reached over and began stroking him over his pants and felt him get harder and thicker with every stroke.

"How are you doing, sexy?" I asked quietly, batting my eyes at him innocently.

"I'm doing GREAT. I can't believe I'm here!"

Well, you ARE here. I said coyly as I lowered his fly and loosened his belt.

I slid off the sofa and sat on the floor between his open legs, looking up at him as I reached inside his underwear and took him in my hand. With my free hand I unlocked my phone, started recording and handed it to him.

He let out a long moan as I eased his cock out of his underwear and got my first look at it. It was long, thick, uncircumcised and VERY hard, so hard I could feel his pulse throbbing in my fist as I began to stroke it. I was leaning towards him and had just opened my mouth when he shot a hot blast of cum about a foot in the air before it came down on my forehead with a splat. At the same time, he slapped my hand away and began jerking his cock furiously as he let out a very loud "Waaaaaaaaaaaaaahhhhhhhh!" sound as he continued to spurt. Most of it was already gone before I could get my mouth over it, and I was careful not to swallow any of it as I attempted to collect every drop of what remained, as evidence.

He collapsed back against the couch and dropped my phone, which I instantly picked up and continued to film myself. Pooling his cum on my tongue, I opened my mouth and presented it to the lens for several seconds so there could be no denying it's existence, and then I swallowed it, gave the camera a wink, and stopped recording.

Before I'd even had the chance to wipe my mouth, Bob was stuffing his snake back into his pants and rising from the couch. "Gee, thanks Krissy, that was amazing! Hope it's okay that I came so fast . . ."

Wiping my mouth I nodded and forced a smile, "Sure Bob. I take it as a compliment."

"Exactly! Fuck you're hot. That was great, can't wait to see the video!"

And with that, Bob was gone but my night wasn't over. A few feet outside my door I heard another man's voice asking Bob something as he exited. "Is Krissy down there?"

"Yep," he replied curtly, "First door on your right."

Bob wasn't my only date that night, he was one of three local men handpicked by "M", all of whom were apparently big fans of my work. They all came one after the other, no pun intended, and it was well after two in the morning before I finished posting all three videos on all of my profiles. I could still taste them the next morning, and my apartment smelled like sex. There were no thoughts of closure on the matter either.

I knew this wasn't the end of it. I'd just given "M" three more videos to use against me, and this was far from over.

I wasn't at work for fifteen minutes before the first text came. "Good morning, slut. Have a good night?"

3

12:00 pm "ANSWER ME SLUT!!"

I'd been ignoring their messages all morning. I felt totally humiliated by what I'd done the night before. I didn't even know who those men were, and now there were videos of me sucking their cocks and swallowing their cum all over the internet. They had been nice about it, at least, and I tried not to forget that each of them had come to my place under the assumption that I had personally invited them. It wasn't their fault, it was "M's", whoever they were. After spending the past 24 hours trying to guess I was still no closer to figuring out who they were. If anything, I was beginning to think that "M" might have anything to do with their true identity. After all, M could stand for anything . . . Mister, Master, Monster . . . who knows, right?