Pay to Play Sissy Pt. 01

I was sitting across from my mother and sister at the breakfast table this morning and sweating heavily. Not because I thought they suspected the deviant things I had been doing lately - indeed, was doing right at this very moment - but because of the sweltering heat coming over me. It was the height of August and money was too tight to run the air conditioning. Even at 8AM the temperature inside was already approaching 90 degrees and climbing.

That explained the quizzical looks they both gave me when I came downstairs earlier in pajama pants, sweatshirt and wool socks. My sister Diane, wearing only flimsy shorts and a tank top herself, looked a question at my mother. She gave a half-shrug and went back to making breakfast. My mother had given up understanding me these days.

"Chilly, Billy?" Asked my sister, equal parts teasing and suspicious. I never went by "Billy", usually Will or William. She only used that name when she wanted to say something snide to her "little brother". Infuriated, I mumbled something and reached for a box of cereal. I studiously focused my attention on the bowl while I ate, unable to meet their gaze. Hoping desperately they'd ignore my peculiar outfit and move on with their day.

Of course, there was a very reasonable explanation for my comprehensive coverings. Well, "reasonable" might be debatable but the reasons certainly seemed good enough to me.

The pajama pants were not uncommon these days - having to hide the fact that I was shaving my legs now led those to be a staple of my wardrobe. Today though they also hid the white stockings that stretched up my legs and contributed to my broiling discomfort. The fabric upon fabric clung to my thighs and calves, causing me to perspire.

The socks were new, but only because I had painted my toenails the night before. Regular ankle socks would have been preferable in this horrible heat but the vivid shade of pink nail polish that had been chosen for me, combined with the white nylon, meant I needed a thicker method of concealment.

The sweater was probably overkill but, after a few close calls recently, I wasn't taken any chances. I had been persuaded to shave my arm hair as part of a makeover and, although my hair was already light and it might have escaped notice, I decided to cover up rather than risk it. The fact that the baggy material fell loosely over my back and prevent someone spotting the "whale tail" of my lacy thong was just a bonus.

As I sat across from my family and suffered through the warm summer morning. My sister stared at me while she munched on her toast, clearly trying to figure out why her weirdo little brother was acting even weirder today. My mother read her paper, finishing her own coffee before getting ready to leave for work.

I looked straight ahead, eating my breakfast and desperately willing them not to guess what I had under a thin outer layer. It was a strange, ridiculous situation - as was how I got into it in the first place.

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The pandemic had not been good to me. I was living at home with my mother and sister, dropped out of college, and unemployed. Most of my time these days was spent sitting in front of my computer, playing video games, and looking at porn.

Ok, TECHNICALLY, most of that was true before the pandemic too, but when I blame the pandemic no one really seems to question it.

Hard to say how it got this bad but I had tried the university thing and found I hadn't been that good at it. I spent one year away and then my failing grades had caused me to move back home to "re-evaluate". I moved my meager belongings back into my room and then had a series of crappy, low-paying jobs. I kept telling myself I'd go back to school - or at least take some courses online - but never got around to it. Some weeks turned into months, which had now turned into over a year.

One the pandemic hit my minimum wage career came to a screeching halt. As such, I now found myself, a skinny, 20-year old guy, living back in his childhood home, down the hall from his sister and mother.

My sister was a year older than I and attending beauty school. I gave her some grief about that when I was at a university but, as a drop-out that recently got fired from flipping burgers, I increasingly kept my comments to myself.

My social life was never particularly active, even before "live-at-home-loser" status. I had the odd date in high school and even a couple of steady things in college. These days though, I occasionally made a few attempts at swiping on apps but never got anything to pan out long enough for an in-person meeting. Most nights I spent trolling around online, looking at pictures of women that would never be interested in me and watching videos of acts I'd probably never get to do.

As my daytime activities dried up I spent later and later nights on my computer. Months started going by where the only human contact I had was related to me and the loneliness was getting a little oppressive. The usual apps refused to pay off so I started looking for human contact in more exotic places.

While many communities suffered during the pandemic, others thrived. I found myself, through necessity, exploring online forums and chats that I hadn't known existed before. Dating sites, adult friend sites, fetish sites - all of which I delved into during my isolation. What started often as "a goof" to see who was in these places turned into a desire to be included as I sought some kind of human connection.

My initial hopes that I would find female companionship on these sites were quickly dashed. Every site I visited promised real, live women on the other end but few delivered. The rare instance that could connect me to a girl usually meant paying big - coughing up for cam sites and private dances.

I definitely did not have the money for any of that so I resigned myself to the social media that catered to guys like me: lonely, horny and desperate for someone to talk to. I consoled myself initially that I was really just chatting with other "enthusiasts". Guys like me who loved naked ladies and wanted to swap pictures and stories. Like a hobby even.

That got old fast. By the third or so month, I feel like I had viewed every naked picture on the internet. My favorite videos had been watched dozens of times and I had exhausted pretty much every site on my (pretty vanilla) interests.

Some of my chats became explicit with guys on the sites. Nothing too wild at first but aching for some kind of sexual outlet meant I'd play along as they talked through their fantasies, occasionally participating. It was a little bit strange at first but served its purpose.

That had become my routine for a good long time. Spending my evening online with perverts, usually old perverts, exchanging thoughts on what we'd do with girls if we ever had a chance to.

It was in one of these sordid communities I met Gregory. I don't know what it was that drew me to him more than the others. It started pretty much the same as every conversation I'd had over the last few months. We had found each others profiles, matched on some interests. He had reached out first.

Gregory was definitely older, like most of the guys on here. He had taken an early interest in me as an attractive young man, but that was nothing new. Myself as a 20-something guy was definitely a hot commodity - on fetish websites, at least, even if nowhere else. Many of the virtual friends I had made had solicited me - telling me I must be very cute, asking me for pictures, or trying to tempt me to turn my webcam on. I had refused them all, save for the intermittent time when I needed a little pick-me-up.

Gregory was different. He made similar comments about my youth and my looks but he spoke to me very differently. We chatted about many things over those first few days - likes, dislikes, hobbies, desires - but it always came back to me. He had a way of focusing in on me that I found I deeply needed at the time.

The isolation of being in a pandemic and having no one (who wasn't directly related to me) to talk to had been taking its toll on me. The superficial chats with users of the fetish sites were fine for an occasional fix but I increasingly needed more. Some deeper connection that had missing from my life for too long. In Gregory, I found an outlet for thoughts I had bottled up for almost a year. "Tell me everything", he would say. And for some reason I would do just that.

I told him about my loneliness. I told him about my living situation and my hopeless reality. I told him about how increasingly hard it was to connect with someone. That the nights of porn and games and touching myself were starting to feel empty.

My fears about never getting my life back on track. On the feelings of helplessness that being broke all the time brought. Very quickly I realized that I needed a release for the anxieties that had been building while I was cooped up in my childhood room.

Gregory listened to all of my woes. Asking insightful questions as we went along, he helped me unwind apprehensions that I didn't even know I had. Not with sympathy always - even in those early days I could sense his dominance. He heard, he understood, but he admonished too. Often encouraging (sometimes forcefully) to look in a new direction.

Typing out the concerns was a necessity - the walls of our house were too thin for me to voice them out loud. But Gregory insisted early on that I turn on my webcam for our chats. Part of it was increased intimacy - I had hesitated with others but seeing each other added more of a connection to these conversations. Part of it also though was monitoring: Gregory would give me his full attention but he also demanded mine. A few times early on I tried to multi-task, which brought swift rebukes. Now, when we talked, I ignored everything else.

I typed, Gregory talked. He did not have the same anxiety that I did about being overheard. Given this, and the increasingly explicit nature of our chats, I had taken to wearing my headphones whenever I was at my computer. I still kept the volume dialed down on them, just in case, but this had the unintended effect of his gruff voice near-whispering his thoughts and instructions directly into my ears each night.

Now, wearing headphones all the time has its risks. It was one evening a couple of weeks in that I released this in a very visceral way.

The irony was that it wasn't even a particularly sexy conversation that night. I had been moaning to Gregory about money - about how I felt powerless without a source of income - when the knock came at my door. I was too caught up in my melancholy to hear it. I typed away while it got loader - just as I realized there was a quiet voice calling my name, the door swung open.

Startled, I luckily had somewhat planned for something similar. I quickly alt-tabbed to a game that I kept running for just such an occasion. I pulled my headphones off one ear and tried to put on an indignant look for my sister, standing there in a towel and looking equally indignant.

"BILLY! Did you touch my clothes in the bathroom?! I can't find anything!" Diane shouted.

My computer desk had been carefully positioned to block a direct view of the screen from the door, for obvious reasons. As such, my sister could only see a portion of what was displayed, but I took no chances. She, on the other hand, was definitely out of the pickup of the webcam, thankfully.

The microphone however picked up the exchange. Even when I did not use it, Gregory had insisted that it stay on at all times.

"Uh..." I started to respond when the gruff voice cut in.

"What's going on." It said. Not asked - commanded me to describe.

I paused, caught between the angry, dripping sibling, and the waiting voice.

"Uh, hey...sister."

She blinked. "Um, hey 'brother'...didn't you hear my fucking question? Did you move my stuff?!"

"From the bathroom floor? Your stuff was everywhere - I put it in the hamper. It was gross..." I started.

"Your sister is in your room?" The voice asked. I nodded involuntarily, realizing only after that I did it and hoping she didn't notice.

"DON'T. TOUCH. MY. THINGS!" She shouted. "I needed that bra in there - I was coming back for that stuff! Now everything's in the wash and I'm running late!"

I shrugged, annoyed at her for interrupting and, more so, for being a slob. This wasn't an uncommon exchange. Even with all my recent screw-ups, I was still the tidy one between the two of us. I started to give a sarcastic reply.

"You moved her things?" Gregory asked through the headphones. I closed my mouth, unsure of what he was doing. My sister stood there staring at me. I stared back, uneasy. "What things."

I glanced at the webcam and then back to my sister. "Before she leaves - say what things you moved."

"Sis, I'm sorry I moved your...bra." I mumbled. "I was just trying to pick up around here."

She rolled her eyes. I sweated a little. Wow, that was weird. Being fed a line from across the country. I turned back to the screen, hoping she would take the hint and leave.

"What else did you touch?" The voice in my ear said. I gulped. No. He can't be serious. I gave my head the tiniest shake. Gave the webcam a pleading look.

"What...else...Billy" he repeated. He used the same derisive name as my sister. Laid heavy emphasis on each syllable. Diane stood there fuming, obviously working her way up to another outburst. Gregory's breath lingered loud in my hearing, strangely compelling.

"I'm sorry." I said again, hesitating. "I'm sorry - I had the laundry basket so I picked up your...panties."

It was Diane's turn to pause. I looked at my screen, unable to meet her eyes. She raised an eyebrow. Opened her mouth but shut it again. Settled for a shake of her head and a mumbled "whatever, perv" as she walked back out the door.

"Good boy." The voice said.

I had no idea that conversation would be the start of the next phase of my life.