Meeting a Dom Online

I had never really done anything like it before - had never even so much as tried online dating. But while browsing a corner of a popular sissy/Dom website, I stumbled across his profile. He was big and manly and Alpha. I could tell even from his casual profile pics that he had a big cock. He also happened to live nearby.

I reached out on a whim, overcome with excitement and lust, touching myself just at the thought of a response. I said something like, "Hey! I saw your profile and liked it... I live nearby. Happen to be looking for a femboy sissy to play with? xD"

I didn't think I would hear back, but he replied quickly. "Absolutely, John. Love your pics, but disappointed it looks like you aren't dressing girly 24/7 yet. I'd definitely change that if I was your Dom. Be a good sissy and send me your info? We can set up a weekend for you to come over and let me feminize you completely. ;)"

I smiled, reading the reply, biting my lower lip. My breath was hot and heavy from the flirting, and my little cock was aching in my briefs. It was probably a bad idea, but I was so sex deprived, I sent my number and a couple burner socials his way anyways. I hadn't allowed myself to cum for weeks, wanting to fully commit more to my sissy lifestyle. Being that pent-up probably made me more bold than I normally would be.

My heart almost leapt out of my chest when he called my phone. I answered in a shaky, shy voice, and we started chatting. I barely remember what we said, I was so nervous. His voice was so deep, so masculine - the complete opposite of mine. But I vaguely remember agreeing to everything he said.

By the time he hung up, we'd set up a date! I was to show up at his apartment Friday evening. and he'd specifically asked - no, wait, ordered - that I be shaved.

I could barely think the rest of the week. I was antsy at work. I kept pulling up his pics and sneaking peaks at them under my desk. I almost got caught a couple of times.

When Friday rolled around, I psyched myself up and made the drive to his place, heart beating like a drum the whole way over. Thankfully, it was a short drive. He lived only a few minutes away.

I walked up to his door and paused. Was I really going through with this? I was standing outside the apartment of a complete stranger. All I knew about him was what he posted online, and that he was into sissies. I had barely dabbled in sissy-ism. Crossdressed a bit. Practiced with makeup a couple times. Tried on a thong that had accidentally gotten left in a public laundry I went to. I had never had a Dom before...

Without realizing it, I had already knocked.

A minute later, he opened the door.

Confident, dark, muscular. He grinned down at me, a good head taller.

"H-hey! Um, Derrick, right?" I barely remembered his name, blushing under his gaze.

Derrick nodded. "That's right. You must be John, the sissy!"

I made a little 'Eep!' sound and looked around over my shoulder. He said it so loud I was sure the neighbors could hear. I didn't want the whole world to know I was a... a... sissy... I quickly nodded and tried to smile politely. "Y-yep! That's uh... that's me!"

He gestured me inside and closed the door behind us. His apartment was nice. A little messy, but modern and cozy at the same time. Big windows, a good open layout, plenty of space and at least 3 bedrooms.

"So, John, how long have you been a sissy?" Derrick asked, sitting down on the couch and inviting me to sit next to him.

I sat with a start at his blunt question. "I- Uh... Not that long, actually... I just found the sissy porn by accident and got into it... and haven't been able to... you know... with regular porn since." Oh god, what was I saying? That was such an embarrassing thing to admit when first meeting someone!

Derrick nodded and said, "Hmm... I like that. I actually invited you here because I thought that might be the case. You see, I'm what you might call a sissy trainer."

"A trainer?"

"Mhm. I teach subby betas like you how to dress, how to act, how to address Alphas, and so on, to help you learn your sissy place. I won't you to do anything, obviously, but if you're interested..." He raised his eyebrows, leaving it open for me to respond.

My heart was racing. He was offering to train me? The logical part of my mind was telling me everything was happening way too quickly. But the sissy part...

"I'm interested..." The words left my mouth before I could stop them.

Derrick smiled. "Great! Then from now on... you're my new sissy, understand? Say 'yes, Master' if you do."

I blushed. I was shaking a little, too. This was way more embarrassing than I had anticipated. Chatting online was one thing, but being in front of a real man... Seeing his muscles strain at his shirt... the way he moved... the way he smelled... it was overwhelmingly masculine, and compared to me... I felt small and cute next to him.

"Y-yes, Master..." I squeaked.

He chuckled at my obvious embarrassment. "Ha-ha, good girl, John! Now as a sissy, you know that your place is serving your Superiors, right? As your new Master and Trainer, I'm at the top of that list. Real men in general come next. Sissies like you are at the bottom. Now repeat after me, 'I am a sissy slut.'"

I nodded along with him, face getting hotter with each word. He was serious, and I could tell he was experienced. The way he was commanding me, I already felt myself wanting to obey, even if it was difficult to get past the humiliation of it.

"I... am a s-sissy slut..." I repeated. My own quavering voice was girly and weak, and lacked all the conviction Derrick had.

He shook his head. "No, again, and louder this time. Don't hesitate either. This is your first mantra, something you should remember forever and repeat to yourself every day. Make it perfect."

"O-okay, sorry..."

"Don't be sorry, you're doing great. Just do what I say and you'll get better, I promise. No again - and remember to always call my Master."

"Oka- I mean, yes Master." I gulped and tried again, looking towards the ceiling to calm my nerves. "I am a sissy slut."

Derrick nodded. "Better! But look at me when you say it, and be proud! You should smile when you say it,don't just rattle it off. Again!"

I myself to meet Derrick's eyes. Seeing him looking back at me made my heart flip. My lips quivered. Having a visible audience made it a hundred times harder to articulate.

"I- I... Oh, sorry, haha. Tripped up a little. I am a s-sissy. Ah, dang it, I did it a again!" I fanned my face. I could feel it getting red with embarrassment.

I was worried Derrick would be upset I was messing up so bad and getting so flustered, but he just smiled and laughed and said, "Don't worry, John. You're doing fine. It's adorable, actually. Embarrassment is a normal part of the process. Here, does this help?" He grabbed both of my hand in his and scooted closer to me.

"I- I- I..." My face lit up red like a hot coal.

Derrick chuckled. "Come on, sissy. You can do it. What are you?"

I gulped and looked into his warm, confident eyes. "I... am a sissy slut..."

"Good! Again."

"I... am a sissy slut!"

"Good girl, baby! One more time, loud."

"I am a sissy slut!"

"Perfect! Now one more time, sissy slut. Loud and proud!" He took out his phone and aimed it at me, taking a video.

It took several stuttering, humiliating tries with the camera pointed at me, but finally I managed. "I am a sissy slut!!!"

Derrick laughed and clapped me on the shoulder. "There you go! Was that so hard?"

I didn't have the confidence to tell him it was incredibly hard, and humiliating.

"Come on, I want to get the next part of your training started. It's important you get used to it early." He got up, took me by one hand, and led me down his hall to the first room. It was an office with a big desk and a couch against one wall. He opened the closet to reveal the true purpose of our visit to that room: The closet was full of girl clothes. Hangers held all manner of dresses, skirts, tops and bottoms, all definitely feminine. He opened the drawer of a dresser and I immediately knew it was filled with panties, bras, garter belts, hose, and all other manner of feminine under-things.

"Did you shave like I told you?"

I nodded, then added, "Yes, Master."

Derrick said, "Good. You have an hour to get ready. Dress nicely - stockings, heels, makeup, painted nails - the whole nine yards. We're going out later and I want you to look good for me, understand?"

I was stunned. There was so much, I was overwhelmed. Finally, I managed to say, "Wh-where did all this come from?"

Derrick shrugged. "One-night stands, ex-girlfriends, other sissies I've trained. I bought a good amount, as well. I want to make sure my sissies are always dressed well. It's an important part of being a sissy. Always dress to please Men. Because what are you?"

I smiled. "I'm a sissy slut, Master!"

"Good girl! See you in an hour!"