First Meet with My Master

Since my divorce, my feelings for crossdressing had come racing back. I'd somehow managed to suppress the feelings during the six years we were married but I think in reality they'd never fully gone away and might have also contributed to the separation.

Now was a different matter though, I was 35 and free to buy all the girly clothes I wanted, and I had amassed quite the collection of both lingerie and more day-to-day clothes but almost all of them fed into my shiny clothing fetish. I had also acquired quite a bit of bondage gear too, but my pride and joy were my pink satin sheets, I just adored slipping into them each night in my girly nightclothes. Now I hardly had any male clothes, only what I needed for work and meeting family, but I lived in girly panties constantly and I'd never been happier or true to myself.

After a while, I set up a Twitter account for my girly side and that only pushed me further down the rabbit hole. Since looking at all the gorgeous people, I'd learned how to properly do my own makeup by practicing for hours in the mirror and bought myself a wig which I kept in perfect condition.

Posting and talking on there had helped me come to realise that I was actually bisexual, something I had tried to hide even from myself up until this point. It also helped me to understand that I liked older, fatter men. Just the sight of a big belly aroused me no end and it ultimately helped me to take the final plunge and meet someone as Paige for the first time for some good old-fashioned grown-up fun.

Although I got a fair few messages through, I tended to ignore many of them but this one seemed different probably because he didn't live that far from me. That, and he was in his late fifties, mostly bold, and had a lovely big belly.

The messages started out fairly normal and vanilla however it didn't take long for things to get more explicit, especially when it became obvious that he was dominant.

I couldn't stop thinking of him while I was at work, I was waiting for the latest message to come through from him so I could see what he wanted of me or if he had sent me a new picture. My lust for him meant that I agreed to do something which I was never sure I would do, meet him in person. I was so desperate to meet him that I even agreed to meet at his house, even though I knew that could be unsafe.

I had a few weeks of looking forward to my first meet with a real man and even though I knew he was more dominant than me, I was still surprised to get the following message.

'Paige,

Prior to our meeting, you must follow the below rules:

- You are not allowed to cum,

- For the three nights prior to our meeting, you must edge for at least one hour,

- You must arrive completely dressed in feminine attire as if you were arriving for a day of work at an office,

- Under this normal clothing, you must be dressed in matching lingerie,

- Your nails should be painted in a way that matches your lingerie,

- You must be clean-shaven,

- You must be prepared to stay all day if required,

- You are to arrive at exactly 10 am,

- Once you arrive, you are to enter the hall and put on the blindfold presented to you, and await inspection,

- You are only to call me Sir, Master, or Daddy.'

I didn't entirely know what to do. Should I run away or do what he said? I felt equal parts aroused and scared so I waited a few hours before I replied. While I was mulling it over, I came to the conclusion that most of these I would have done anyway. Sure, I would have to think a bit more carefully about my outfit and put in some real practice painting my nails but that's nothing that I couldn't manage.

Straight away I got my nail kit all sorted so that I could practice more, I figured if I did some every night I might be ok. Although I had plenty of lingerie already, I wanted to make sure that I too feel special for my first-time meeting Master, so I decided to get a new lingerie set and make it as girly as possible.

As I couldn't decide whether to go for a normal or sexy outfit, I decided to go for normal looking on the outside and slutty under. My new lingerie set was gorgeous, and I couldn't wait for it to arrive, it was a pink satin and black lace set of a bra, briefs, and a waspie to hold up my stockings. This also meant that I could have lovely girly barbie pink nails to match.

Practicing my nails every day was tough, not because of the act itself but because sitting there in my satin robe being a girl really turned me on and I wasn't allowed to cum. The last 3 nights were the toughest as the edging really made me leak. Although I wasn't instructed to, to help me edge I watch gay porn of chubby men screwing each other as that is what I wanted more than anything.

The day before our meet, I did my last hour's edging and prepared to spend the whole evening getting at least partly ready. I started with a bath; girly baths had become one of my favourite pastimes as it meant I could lie there in the bubbles feeling feminine. After this, I carefully prepared my nails so that they were the perfect glossy pink colour. Finally, I got all my outfits together and hanging on the outside of my wardrobe, ready to slip into in the morning.

I could barely sleep that night, partly because the edging and satin nightwear on satin sheets drove me crazy but also because I was just so excited to meet Sir.

I set my alarm extra early on the big day to be 100% ready, and when it did go off I immediately got up, showered, and made sure I was completely smooth. Slipping on my satin robe, I then sat at my vanity table and spent an awfully long time perfecting my make-up and hair.

Finally, it was time for my favourite part, getting dressed. I knew that wearing panties over stockings made certain things easier, but I just loved the look of them under the straps, so I slipped them on and tucked myself in as best as possible. Sliding nylon stockings over my perfectly smooth legs really drove me wild and I could feel myself becoming ever more submissive.

After the bra, it was time to start looking at least slightly respectable and to get dressed. I'd chosen knee length flared leather dress with pink patent heels to match my nails and to add a splash of colour. Finally, as it was a little cold out, I put on my figure-hugging puffa coat which came to hip length and perfectly showed off the flare of the dress.

With a deep breath, I left the house before I had time to change my mind.

It didn't take me long to drive to his house, but my hands were shaking by the end, especially when I saw that it was a rougher area, and the house didn't seem too well kept. What had I let myself in for?

I figured I had come this far so I touched up my lipstick. This sight of my pink nails touching up my pink lipstick in the mirror made me realise I really did want this, so I sprayed some perfume before nervously walking up the path. Before I could knock, I notice a post-it on the door saying, 'Enter Paige', and I took a very deep breath and pushed the door.

Once the door was shut, I immediately put on the black silk blindfold and waited. It seemed like an age before I could sense anyone nearby although it was probably only a minute or two. I could feel him getting closer until I could feel his hands start to rub me, first my hips, then my ass then squeezing my tits through my shiny puffa coat. All I could do is stand there as he unzipped my coat to get a better view of my leather dress.

Stood immediately behind me, I could feel his big hands exploring my body. My knees went weak as he lifted the back of my dress to inspect my stockings and panties. Then, with his hands on my hips, I felt him turn me and pull me close to his big body and kiss me. The feeling of being kissed while I was wearing lipstick was magical, I'd never felt more feminine. I still hadn't seen him, but I could feel how tall he was as I put my arms around his neck, he seemed to like this, and he pulled me even closer by my ass, so much so that I could feel his big belly and bulge against me.

"Now Paige," he said in a gorgeous manly voice "I want you to take the blindfold off, go upstairs into my bedroom directly at the top, strip into your lingerie and wait for me. Do you understand?"

"Yes Sir" I replied, knowing there wasn't a bone in my body that wanted to say no.

I didn't dare look back as I carefully went up, still not entirely confident walking upstairs in heels. I entered his bedroom, and it too wasn't especially well kept with dirty washing in various places and the bed unmade but I didn't care as I was being lusted after by a real man and I could put up with it to be with him, even if it was just this once.

I carefully removed all my clothes and neatly laid them on the side before slightly making the bed, just enough so that I could lay on top of it and wait for him. Lying there in my lingerie and heels for what seemed like an age, I'd never felt so feminine as I looked down at my stockings and heels.

Eventually, he entered, and he was even sexier than I ever imagined. I know he wasn't everybody's ideal, but he was fairly old, average height, and balding but most importantly had a big belly and ass. As he stripped off, I couldn't resist but to run my hands down my body and rub myself as if I had a real pussy.

He smiled at me rubbing myself and joined me on the bed. Lying next to me, looking in each other's eyes I couldn't resist but to make the first move and I pushed my body against his so that we could kiss once more. We immediately grabbed each other's asses and pulled ourselves together, I loved how I could barely hold any of his it was so big.

I couldn't help but dig my fingers in his ass as my mouth opened and his tongue entered. His taste and smell drove me wild, and I knew at that point what I needed to do next so I moved my hands down his body, rubbing his belly until I could reach under and feels his semi-hard cock. I felt emotions I had never felt before as I felt it grow in my hands and I felt my own tucked cock strain against my pink panties.

Once I could feel that his cock was rock hard, I decided to start kissing my way down his body, making sure that I sucked his nipples and kissed his hairy chest and belly as I went. Once I reached his crotch I started kissing and sucking his balls before licking my way up his shaft so that I could lick his precum which tasted divine.

As I was preparing myself to suck my first real cock and was kissing the tip, he grabbed my head and started to fuck my mouth. The feeling of it on my tongue as it got deeper and deeper made my own cock leak more, but I wanted it to be all about him, at least for now.

It didn't take long for him to be rock hard so I sped up hoping I would get to taste his juicy cum. But as I felt he was about to cum he suddenly pulled out and looked me in the eye, as his pulsating cock was centimetres from my lips.

"Now Paige"

"Yes Sir"

"Do you want me to cum in your mouth?"

"Yes, please Sir, more than anything"

"Then you're going to have to commit to me in a very specific, and potentially demanding way," he said with a sly grin on his face.

"What's that Sir?"

"You're going to have to let me lock you in chastity if you want to taste my cum."

"Sir? What do you mean?" I knew all about chastity from Twitter, but I'd only been half curious and never given it any serious thought.

"It's quite simple Paige. I will lock up your cock in a chastity device so that you can't use it or even get hard until you come back to me. Only then will I consider if you deserve to be unlocked".

"Oh, I'm not sure Sir," I said, hoping it would buy me some time bit it didn't work and he grabbed my head and started to slowly fuck my mouth again.

"Well Paige, if you want to taste what I have to give you," he told me staring straight into my eyes "you are going to have to agree to wear a cock cage.

"Or leave now and don't come back."

He held his cock all the way in my throat as I thought about it, I could barely think about anything with his balls on my chin and belly on my forehead. I was so intoxicated by the situation that there was only one thing I could do, I started to nod.

"What's that Paige?" he said as he pulled his cock out of my mouth.

"I want you to put me in chastity, Sir."

"And why is that?"

"So, I can taste your cum Sir."

"What a good girl you are Paige," he told me as we kissed once more. "Now I hope that you realise this is entirely your decision.

"I'm not going to force you in any way as I'm not going to tie you down to put you in it and it'll be up to you to ensure you're soft enough to be placed in it".

"Yes Sir" I obediently said as he went around the room collecting the device.

He came back with a small, bright pink device which was slightly smaller than my fully limp cock. I knew that I was a grower not a shower and only really average size, but this would really restrict me.

Sir placed the device on the bed and lay next to me.

"Now Paige, we are going to lie here until you're small enough to fit inside your new cage. Even if this takes all day, you're just going to have to find the right mindset".

"Yes Sir of course Sir."

I had no idea how I was going to do this. I had just had one of the most erotic experiences in my life and I was lying with a sexy man while I was in lingerie, so my cock was rock hard. I started by just staring at the wall first but occasionally I would catch a glimpse of my lingerie or Sir's sexy body which would make my cock grow and Sir chuckle.

After almost an hour of this not working, I decided to take more of a meditative approach and think through some work things as a distraction. It almost worked until Sir put on the ring part of the device around my cock which of course turned me on and made me too big for the cage.

With at least the ring on I was now able to repeat the process and after another 30 minutes the cage was in place, and I heard the click of the locking mechanism.

I looked down and saw my now caged cock and it instantly turned me on. It was the first time in it that I had been restricted and it instantly turned me on even more which made it worse.

"What a good girl you are Paige," Sir said as he slipped the key onto a necklace which he then wore. "I think we're going to have an awful lot of fun".

With that, he started stroking my cage which again made it worse and I wondered what had I let myself in for?

To respond I started stroking his still semi-hard cock which got us both back in the mood and we pulled each other close, and I could feel his sexy big belly against mine once more.

"Please can I taste yours now Daddy" I found myself saying as the straining from my cage drove me wild. Without a word, he nodded and pushed my head down.

His cock tasted just as good, if not better than before and I really wanted his cum so I went for it. I took his whole length immediately and sucked as hard as I could over and over. It wasn't long until it was pulsing and he was moaning once more.

Even when I thought it couldn't grow anymore it did and suddenly my mouth and throat were full of his juicy cum. I couldn't believe it tasted this good, so I sucked every last warm drop out of it.

Once I had licked his cock clean, I lay next to him so he could hold me in his arms, making me feel like the most secure person in the world.

After a while he told me that I had to leave so I got up and started to put my dress on again.

"And don't forget Paige," He said as I was putting my coat on "If you ever want to get hard again, you'll have to come back the same time next week when I might consider unlocking you".

"Yes Master, of course," I sheepishly replied as I left this grubby bedroom and house for my first trip into daylight as a locked and owned girl.