Evening Out with My Master

The drive home was absolutely terrifying. Driving around with a stranger's cum dripping from my face made me feel so obvious and humiliated. I was thankful that the roads were quiet, and I didn't have to buy any fuel, but I've never been so scared and aroused at the same time.

Shaking as I got out of my car, I paused as quickly as I could so that I could take a selfie to send to Master so that I could prove that I had carried out his instructions. I was convinced some neighbours would see me but what choice did I have? I couldn't displease Master again.

A message came through on my phone and my heart skipped a beat, knowing it must be from him.

"Good girl," it said, and I breathed a massive sigh of relief at having in some way pleased him "Pick me up at 7 pm tomorrow as we're going to The Horse and Jockey pub and don't want to drive so don't be late."

My first thought when reading this was elation, Master obviously thought enough of me to be seen together but then I came to realise that tomorrow was a Friday night, and the place would be heaving. I also knew the pub and it wasn't exactly glamorous, but I suppose that was to be expected given the state of his house.

It was actually a while before I realised that I still had cum on my face, so I quickly took a shower and slipped into my satin pyjamas for the night. It took a long time to get to sleep again, it always did when I met my Master but I could still somehow taste the stranger's cum on my tongue which made me strain in my chastity once more.

I had such vivid dreams about my Master, as I had done most nights but tonight, they felt more real than ever. Tonight, I dreamt that my Master had taken my anal virginity, and we went out for a lovely meal before he took me home, before slipping me into some sexy lingerie and making love to me in the gentlest way. All I could think about when my straining chastity device eventually woke me up was him being so tender and caring towards me, something I was sure would happen someday soon.

I didn't have much time to think about my outfit as it was the same day I was meeting him again, but it was all I could think about while at work. Eventually, I figured I would go slightly slutty but not too much as I didn't want to draw too much attention, so I went for my black leather skirt that came to just above the knee, a white silk vest that really made the shape of my bra obvious and a black suede jacket. All this was over a fuchsia lace bra and panties set which I felt really showed my girly side.

Another problem I had was that my best wig was soaked with a stranger's cum. I would instead have to go for my older red shoulder-length wig and although it wasn't my favourite, it would have to do. It also meant that the second I got home from work I had to rush to get myself clean inside and out and get the wig ready as it needed a little tending to.

Before I realised it, I had to leave the house and I hadn't even worked out what shoes to wear, in a blind panic I threw on my heeled ankle boots to complete the look, grabbed a purse, and rushed out of the house.

Thankfully, I had managed to make it to his house just in time and he came walking down his path in a tight-fitting t-shirt and jeans that really showed off his belly which drove me wild. To my surprise, he actually got in the back of my car making me seem like his chauffeur for the night, but I suppose that was my place.

The drive to the pub was actually quite nerve-wracking. I didn't know if my Master was quiet because I had displeased him, or he was just generally being quiet. All I knew was where I was going so, I drove to the pub, straining in my chastity as I went.

"Come round to my door," he finally said as we parked up, "I've got a treat for you."

"Yes Sir, thank you, Sir." I said without hesitation as I nervously made my way around to him.

"You'll be wearing this tonight," he said as he pulled a collar from his pocket which was bright pink and had a D ring on the front. "Now, turn around and move your hair aside."

I did as I was told and started to breathe heavily as he stood behind me and slipped it around the front of my neck. If it wasn't for my chastity I would have cum as I heard him buckle and lock it in place. It was such a turn-on to feel his belly against my back as he locked the collar to me that I even pushed my ass backward so that my leather skirt was grinding against his cock.

"Thank you, Master, I'm so grateful to be collard by you."

"Pleased to hear it," he told me as he started to kiss the back of my neck and rub my ass and before giving it a big smack.

"I want you so much Master," I panted as I recovered from being spanked "I need you."

"Let's just get inside shall we" he said slightly abruptly and as he put his hand on my waist I almost melted.

I knew by reputation that the pub wasn't glamorous, but I was actually slightly worse than I imagined. It was made worse by the fact that I thought everyone was staring at the pink collar I was locked in.

The smell of stale beer was thick in the air as we forced our way past the bar to a booth in the corner. I was glad it was out the way as I had never realised before how short my skirt went when I sat down; I was definitely showing a fair bit of thigh but my hope of hiding away in the corner all evening was soon dashed.

"Go and get me a beer, will you?" Master said, holding out a £10 note for me "and yourself something non-alcoholic too."

"But Sir," I stuttered "I've never been out like this before."

"Just get on with it if you don't want me to punish you."

"Ok Sir, sorry," I said as I braced myself to go to the bar.

Thankfully, it was actually fairly easy at the bar despite how busy it was. At one point I felt like someone was feeling my ass, but I was far too terrified to do anything about it.

Back at the table, we sat closely next to each other with his arms over my shoulders, truly making me feel like I was his partner as we talked for ages about all sorts of things but mostly it was just everyday chat like any other couple.

As the evening went on and he'd had a few drinks, I couldn't resist making some kind of move, so I put my hand on his thigh. I rested my head on his shoulders as I started to rub his leg, steadily moving my hand higher and higher until it reached his bulging crotch, and I could feel his hard cock.

I looked into his eyes as I started to rub his cock and he leaned down to kiss me on the lips. In that moment, collared and kissing him in public I knew I would be his forever.

"I'm so glad to be owned by you Sir," I told him before he plunged his tongue back into my mouth.

"Pleased to hear it," he replied as I continued to rub his cock under the table, "let's go to the toilet where you can thank me properly."

With a smile on my face, I slid my way around the table, very conscious of how much leg I was showing. As we walked through the bar, I felt like everyone must have been looking at my collar, but I immediately felt reassured when my Master's hand rested on my ass.

I felt so naughty as he pushed me into the men's toilets, when dressed in male mode it wasn't a problem but this time I was in a skirt and heels, but I didn't care, I just wanted to suck his cock.

Thankfully, all of the stalls were empty, so we went to the one furthest away from the door and just about squeezed in. The cubicle was disgusting, with toilet paper on the floor and it stunk of piss but all that mattered was that I would get to suck cock and then immediately go out in public again which I had often fantasised about. I couldn't wait to go through a busy bar wearing a collar at having just sucked a lovely cock, my Master had other ideas though.

We started to kiss, forgetting where we were for a short while, and my hand immediately went straight to his cock, it was all I could think about, and I couldn't wait another second to undo his trousers and rub it.

To my amazement my Master returned the favour and started to lift the front of my skirt, I was so hoping that he would unlock me but no, he just rubbed the tip of my chastity cage through my panties as if it was a real clit. This made me weak at the knees, my cock had been locked up for weeks now and I just wanted to be free so to be teased like this was almost unbearable.

I was desperate to taste his cock again, so I grabbed his balls and started to rub them but as I did so he turned me around so I was facing away from him. His hand slowly lifted my skirt to display my panties to him and I braced myself for a spanking, but he completely shocked me by instead pulling my panties down to just below my ass cheeks and started to rub his fingers up and down my ass crack.

As his fingers started to tease and rub my ass pussy, I felt him get something out of his pocket and some cold lube was squirted onto my hole. As the lube started to do its work, I felt the first of his chunky fingers start to stretch me as his first finger slowly slipped in.

In and out the finger went until just as I was getting used to it and I felt the next finger start to penetrate me. It felt a bit award at first but as it went deeper, I could feel my ass accept it, just as my hole was at its widest and I let out an involuntary moan I heard a terrifying sound, the door opening. I could feel his knuckles really stretching my ring as the bloke seemed to take forever to take a piss. I had to bite my lip as it was all I could do to stop myself from moaning in pleasure, especially when my Master started to wiggle his fingers inside.

The second the door closed behind as he left, I let out the biggest moan I had ever released.

"My God," I said catching my breath, "I need you inside me so much."

Without a second's hesitation he bent me over a little bit more and started to push against my hole with his cock. Despite having just been fingered I could feel my hole stretch as the tip of his cock started to enter me. As the tip went in, and my ass clamped around it, I let out another groan as I could feel the last remnants of my masculinity dissipate, knowing I would be forever owned by my Master.

Master slowly, but firmly, pushed the entire length of his veiny cock in my ass till I could feel his balls resting against me. I felt so unbelievably feminine with my skirt lifted up around my waist, my panties partly fallen down and my tiny little cock dripping in its cage.

"Oh fuck!" I couldn't help but moan as my Master started to move his cock back and forth inside me, no matter how many times I'd used toys on myself in the past, nothing could have prepared me for this ecstasy.

I could barely think anything as his pace started to pick up and he started to pound my ass, endless people could have come in the toilet, and I would never have known. I could feel his throbbing cock stretch me more and more as he started to pant and pick up speed.

My mind was racing with pleasure and I just wanted him to release so I had to get my mind together and start to push back. I could tell I had pleased my Master when he grabbed my hips as I tried hard to tighten my ass muscles around his cock.

Harder and harder he pounded me, turning me into his woman as he really squeezed my hips and with one last thrust ensured his whole rock-hard cock was deep inside me as I felt his it explode inside me. I could feel wave after wave of cum filling me up as my mind went blank and all I could feel was intense, please knowing I had pleased my Master as he took my virginity.

I felt empty as Master pulled out of me, I just wanted him inside again and I suddenly came back to reality, realising I had been screwed in a filthy toilet like the dirty slut I was.

I could barely walk back to our seats, the feeling of his cum slowly seeping into my panties made me feel like everyone in the crowded bar knew exactly what we had just done.

Once he had finished his drink it was time for me to drive him. Once again walking through the bar with his arm around my waist and feeling of cum soaked panties against me made me strain in my cage even more.

When I got him home, I knew I couldn't just leave him as he was fairly drunk so I struggled in my heels to make sure I got him in his bed. I even had the chance to use the situation to my advantage by stripping off his jeans so that I could once again see his bulging boxers.

I stripped off into just my cum soaked lingerie and slipped next to him, feeling incredibly secure next to him as he snored away. Unsurprisingly I struggled to sleep, not because of my Master breathing heavily behind me, but because I had finally lost my anal virginity. I had always hoped it would be in a loving, romantic way but instead, I was fucked in a scummy pub toilet, what did this say about me?

Before I knew it was morning again, I woke to the gorgeous smell of my sweaty Master next to me in bed. I knew that I needed to be away soonish, so I decided to wake my Master in the most delightful way, a blowjob.

As he was asleep, I didn't even try and be subtle about it, I just put my hand on his boxers and started to rub his gorgeous cock. I loved the feel of it growing in my hand and before too long I slipped his boxers down just enough as it sprung out. The glistening of the precum was too hard to resist and I started to lick it up and down as it grew to full size.

I started sucking the tip of his cock and it must have done the trick as he moaned with pleasure and started to rub my hair as I began to take it deeper down my throat. I took my time about it, making sure I kissed and sucked every inch, from the tip down to his balls. As soon as I could feel him thrust towards my mouth, I knew it was time for me to take it all.

Somehow, I felt like I could still taste my ass on his cock, and it drove me wilder, reminding me what a whore I had been last night, so I instantly sped up. I took his throbbing cock deeper and faster in my mouth and as I could feel my own strain in its cage I started to moan, getting pleasure from how much he was enjoying it.

Thankfully, it didn't take long for him to grab my head and push every last part of his cock down my throat. As he did, I could feel it straining, ready to release. When it did, wave after wave of cum went straight down my throat. I had never known so much cum, and I loved being made to swallow every last drop.

"Thank you, Sir," I gasped as I stopped the cum dribbling down my chin and pushed it into my mouth, "I'm so sorry I have to go."

"Don't worry about it," he replied, as he started to unlock my collar, "I expect you to be here promptly Friday evening to spend the weekend.

"Detailed instructions will follow."

"Yes Master, of course, Master," I said as I started to get dressed, knowing my Master was watching me.

With that, I left his house once more, no more an anal virgin, but hoping there would be more to come next weekend.