Meeting Mistress Mercy

The following story is purely fantasy. It will be based on Mistress Mercy, and the story will be based around what I would like to happen if I was ever lucky enough to meet her. Please enjoy, and leave comments and feedback.

My name is Alex, I'm currently single, 29 years old and currently live alone in an apartment just outside of London. Growing up, I was shy, and never had it in me to approach girls and ask them out. That meant I didn't lose my virginity until I eventually turned 25 to my last girlfriend who split up with me a couple of years ago when she found out about one of my kinks. That kink was pegging and being dominated by a woman. When I initially brought it up with her, then the more we looked into it, the more she started to question why I'd want to do something like this. Eventually the usual remarks came out, 'are you gay? Are you going to leave me for a man? Only a gay man would like to be fucked in the ass?' I spent some time trying to convince her otherwise, but it was clear our relationship was past the point of saving, so we called it quits.

After we called the relationship off, we didn't remain friends and I'm almost certain she told some of our mutual friends about my desires and what I wanted to try. This meant I spent less time around my friends and more time at home alone, browsing the internet. As I set up my reddit account, I delved deeper into the world of pegging. And before long, I was starting to think my ex-girlfriend might've been right all along. I started to look at it in a different way, did I want to be fucked by a real man? I wasn't sure. One thing I did want to start doing, was dressing up. I'd taken a liking to jerking off to sissy captions on reddit and I was soon imagining it was me. That thought quickly left me though, but I was left with a fantasy that I wanted to try more than ever.

I wanted to be fucked by a woman, wearing a strap-on whilst wearing lingerie.

As I developed this fantasy, that's when I came across this very beautiful, petite lady on reddit. And she went by the name of Mistress Mercy. I couldn't work out whether she'd just started on a famous adult platform but as soon as I seen her stuff, I had created an Only Fans account and subscribed in an instant. Over the next few weeks, she posted new content, all of it involving either domination or pegging. I lost count of the number of times I jerked myself off to her videos. A lot of the content she posted as well included sissies. She'd be fucking guys who were wearing lingerie and I couldn't help but imagine that I'd get that opportunity one day.

It took me a few months, but I finally plucked up the courage to message her on her Only Fans account. Figuring I'd never get a reply, I sent the message and thought nothing of it for over a week. I just continued to wait for her newest videos, and I would jerk myself off to them. Every time she released a video that would need buying to be able to view it, I would spend my money just so I had them all on demand whenever I wanted to watch them. Then I received a shock one day when I had unread message, and it was from Mistress Mercy and not just some random account trying to sell me a PPV video.

The message she'd sent me was a voice note, I at once turned my speakers up to full volume and played it, 'Hello Alex,' she had to most amazing accent, I didn't think accents could be sexy, but hers was. 'You want me to fuck you with my strap on do you? What makes you think you can take my dick?' Without even thinking, I found myself stroking myself listening to her voice. I quickly sent her a reply saying that I'd never tried anything like this before, but it was a big fantasy of mine.

There was no quick reply and whilst I waited for a reply, I started to browse online and started buying myself panties. I must've spent nearly £200 on panties alone from Victoria's Secret before I found myself wearing them every day. As the days ticked by, I thought that one message may have been a one off, but about a week later I had another voice note from her.

'So, you're a virgin, are you?' Then she laughed, 'now you have my interest, I do enjoy taking someone's anal virginity. If you're serious about this, we can talk.'

A wave of excitement flooded through my body which was quickly followed by nerves. I couldn't back down now, so I replied once more saying there's nothing more, I'd rather do than have her take my anal virginity. I also told her about my newfound love for lingerie and that I'd brought myself to orgasm many times watching her videos and listening to her messages. The responses didn't get any quicker. And that meant I was on the edge over the next week whilst I waited for my reply. I started looking at sex toys online, but I wanted to be a complete anal virgin, if by some miracle this happened.

Again, a week later, I had a message. Quicker than I had before, I pressed play. 'Luckily for you Alex, I'm looking for someone new to make content with for my page. That would be one stipulation of you getting your wish, I would need to film it for my Only Fans page. If this is something you'd be willing to do, send me your number so I can contact you to make some arrangements.' In an instant I replied, sending her my mobile number without even thinking about it. I wondered whether that was the right decision.

But thankfully, it quickly became the best decision I ever made. A message appeared on my phone through WhatsApp. Mistress Mercy sent me a verification photo, so I knew it was her for definite. I sent her some photos of myself in reply, I didn't want to be embarrassed and have her telling me she didn't want to fuck me in person, so I thought I was getting the opportunity in early for her to turn me down. The reply I got was 'very nice,' which reassured me ever so slightly. After messaging each other over the next few days, the time had come for our first meet in person. The text she sent me read, 'before we meet to film content, I always like to start with a social, please meet me on Saturday at 2pm.' We confirmed a location which was a pub near the centre of London, and then I had to spend the next few days, trying not to overthink about the meet. The main thing running through my head was that I was being set up,

When Saturday rolled around, I tried to occupy myself with mundane tasks around the apartment until about two hours before I started to get ready. After I'd showered, I started to get ready and faced another dilemma. Did I want to wear panties under my jeans for this? I'd never been outside the apartment wearing them yet and usually wore them when I got home from work and in bed on a night. There was always a risk I could be seen wearing them, but what are the chances of me seeing someone I knew? The more I thought about it, I almost talked myself out of it before taking the plunge and reaching for a brand-new pair of white lace panties. I finished my look with a pair of skinny jeans, t-shirt and an oversized hoodie which covered most of my ass before leaving my apartment and heading to the tube station to head to the pub.

Upon arrival to the pub, I started to panic. I looked around the main area of the bar and couldn't see her. Then as the hope was fading and the disappointment was rising, I spotted her, sitting at the table furthest away. As I approached her, a smile broke out across my face, she was even more perfect in person. She was petite, had a sleeve tattoo and was currently dressed in a little black, strapless dress with tights, red heels and had her long blonde hair down, which reached just over her breasts. When I reached the table, she stood to greet me.

'Alex, lovely to meet you,' she said in the voice that had become so familiar to my ears on Only Fans. She kissed me on both cheeks and my cock jumped a little inside my panties.

'So lovely to meet you too,' I responded. 'Would you like a drink before I sit down?'

'Of course, I'd love a cocktail,' she said as I turned and headed to the bar.

I returned from the bar shortly after and took my seat next to her. And for the next hour or so, we chatted as if we were nothing more than friends, getting to know each other, or more her getting to know me as I told her about my fantasises and how they came around. When I told her about my earlier relationship and how it broke down, she was shocked and took my side and wasn't very complimentary about my ex and the things she said to me when I told her about pegging. After that, the conversation seemed to take more of a turn towards why we were here.

'So, you've never had anything in that cute little ass of yours before then?' She asked suddenly.

'No...,' I paused, thinking I would finish that sentence by saying her name but then I realised I didn't know what it was.

'You can call me Mistress,' she said, almost as though she was reading my mind. I blushed a little before she moved on to her next question. 'And you're happy for me to post whatever we do on my pages?'

'Of course... Mistress,' saying it for the first time felt slightly strange but more of a turn on.

'You could wear a mask if you're not comfortable with your face being on camera,' she said.

'I'm fine with my face being on camera,' I said shyly. 'I think it's time people saw me for what I really am.'

'And what's that?' A smile breaking out across her face.

'A sissy who needs to be fucked in the ass with a strap on,' I said as quiet as I could, my head dropping to my chest.

She smiled and reached for my face, placing her hand gently on my cheek and my head rose back up to face her. 'The first step is always accepting who you are,' she said reassuringly. 'Now, you said in your messages that you've started wearing panties. Are you wearing some now?'

My face must've turned a crimson red instantly, 'yes Mistress.'

'Are you really?' She almost laughed. 'Lean forward so I can take a look.' She noticed I was a little hesitant, 'don't worry, nobody will be able to see.'

I leaned forward to the table, as close as I could without making it look weird. I felt Mistress move slightly behind me and started to lift my hoodie and t-shirt before I felt her cold hand against my lower back. Her hand then pulled my jeans back and I felt her grab the waistband of my panties and pull them up slightly, giving me a tiny wedgie in the process. 'Uhm, very nice,' she said before putting my hoodie and t-shirt back over my jeans. 'Is this your first time wearing them in public?'

Again, I replied 'yes Mistress.'

'It's a good start,' she laughed. 'So, I need you to go home, sort out your Only Fans account so you're officially a performer and then we'll go from there.'

'Sounds good,' I told her.

'Do you shave?' She then asked me, just before she got ready to leave.

'I try to, as much as I can,' I told her.

'Well, it would be good if you could be smooth for our recording, at least in the important areas.' She stood up and we both left, once we were outside the door, she spoke again. 'Get in touch when you have your account sorted and we'll book a date in. The first meet will be in a hotel. Goodbye.' And just like that she turned on her heels and left, and I watched her as she walked away before I realised that I was in the way of other people and decided to make my way home.

As soon as I got home, I was straight onto the Only Fans website and went through the whole verification process so that I could become a performer. It said it could take a couple of days for me to receive verification and that felt like weeks. I checked every day to see whether the email had come through and nothing. Five days later, and the email had finally arrived. I was officially verified and could upload videos and be involved in other people's videos. I quickly screenshotted the email and messaged it to Mistress Mercy and awaited her response. It was the next day before she replied, 'Great,' her message read. 'I've got a room booked for Saturday; can you make it?' Butterflies immediately filled my stomach, I wasn't expecting it to happen this quickly, but at least the butterflies were more excitement than nerves. I responded saying yes, and received a quick response telling me where the hotel was and to 'make sure I did the basics before arriving.' I knew what she meant and had already bought what I needed to do it.

Over the next couple of days, I looked into different ways of shaving and settled on using hair removal cream. Whether or not that was the right idea, I don't know but I was a rookie and wanted something quick and easy. I was particularly hairy from the waist up so didn't bother with that, but by the time I was finished, I was smooth from the waist down and it felt incredible. It felt so good, I went out to my local shop and bought some hold up stockings to try and when I tried them on, just rubbing my legs made my dick get hard.

When I woke on Saturday morning, it was early due to the excitement of what was about to happen. I milled around my apartment for a couple of hours before starting to get ready. For my outfit of choice, I chose a white pair of lace bikini panties and my hold ups. I put jeans, t-shirt and some socks on over the top of my lingerie before grabbing a jacket, some shoes and headed for the tube station. The hotel was overlooking the River Thames and it was exciting to walk past all the tourists walking up and down, with none of them knowing what I was wearing underneath my clothes or what I had planned for this afternoon.

As soon as the hotel came into view, I got my phone out and messaged Mistress Mercy to let her know that I was almost there so she could meet me in the lobby and take me up to the room. As I approached the main entrance and walked into the lobby, she appeared from round a corner that led to the elevators to take you up to the rooms. She was dressed simply in an oversized t-shirt and a pair of leggings, yet she still looked amazing. She greeted me with a smile before I walked over towards her, and we called the elevator before jumping in. Luckily there was only the two of us in the lift, but it was still awkward until she broke the silence.

'Nervous?' She asked me, looking at me and smiling.

'A little,' I said, breaking out my own half smile.

'There's nothing to be nervous about, if at any point you're not comfortable, just say, and we can stop filming straight away. Are you okay with me talking dirty? And maybe some humiliation? It's all for the camera,' she said, and I nodded to say I was okay with it.

When the lift finally reached our floor, she led me to her room, opened the door with the key card and I followed her inside. The room was nice, I would imagine it was one of the nicest in the hotels. It was very spacious with a window overlooking the river. All around the room were cameras on tripods and other various bits of recording equipment.

'Get yourself comfortable,' she told me and disappeared off into the bathroom. I sat on the bed and kicked my shoes off and took my jacket off, placing them both neatly next to the chair in the corner of the room. A couple of minutes later, Mistress Mercy returned into the room carrying some toys and lube. Amongst the toys was a harness with a flesh-coloured cock attached to it which looked a decent size. 'You ready?' She asked once she'd placed the toys on the bed.

'I think so,' I told her with a hint of laugh in the middle.

'Right, I'll undress you once we've started filming,' she started to pull her top over her head, revealing a lace white bra underneath. Then she pulled her leggings down to reveal the matching thong. 'Then I'll take the lead from there and remember, if you're uncomfortable with anything, say something.'

When I said I was ready, she grabbed a remote from the table near the TV and hit what must've been the record button on the main camera which had a full view of the bed from the corner of the room. 'Good afternoon boys and girls,' she said facing the camera. 'Haven't I got a special treat for you all today, you see Alex here,' she placed her hand on my shoulder. 'Alex is a virgin, and he's come here today so I can fuck him for the first time, isn't that, right?'

'Yes Mistress,' I mumbled in response.

'Oooo he's a quick learner,' she said laughing. 'Now have you come prepared like I asked?'

'I have,' I responded quietly again.

'Stand up for me then, so I can take a good look.' I rose from the bed and stood in front of her. She was smaller than I was, her head just about reaching my shoulders. She started pulling my t-shirt up and I eventually pulled it over my head. She unbuckled my jeans and started to unzip them as my own white panties came into view strained by my now hard cock. 'Oh, very nice,' she said once she noticed. 'White, very virgin like of you. And look at your small dick getting hard, pathetic.' She then pulled them down my thighs until the tops of my stockings came into view. 'Oh wow, Alex, you've really outdone yourself, haven't you?' I stepped out of my jeans and took my socks off in one go and they were discarded to the side of the room with my other clothes.

I walked to the middle of the floor so the camera could get a good look at me, 'isn't she so pretty?' Mistress said, 'look at my new little sissy in her lingerie, I'm going to have fun breaking this one in.'

Mistress led me back over to the bed and ordered me to get on all fours with my legs spread but positioned so the camera would get a good look at my ass. She grabbed the lube and walked behind me, pulled my panties into the crack of my ass, and spanked me hard. I let out a little yelp, and she spanked me again. 'Such a nice fuckable ass, but I think we should start with something a little smaller whilst I play with you,' she said and pulled a medium sized pink butt plug closer to her. My panties were then pulled down to my thighs, exposing my asshole before the cold sensation of lube started to drip down my smooth hole and was spread around by Mistress' hand. She then coated the plug as well before gently pushing it into my ass.

'Oh fuck,' I moaned as the plug pushed past my sphincter and into my ass.

Mistress laughed, 'if you're struggling now, it's going to be fun when I fuck you later.' She continued to push the plug into my ass until I felt the base of it resting against my ass. Then my panties were pulled back up into place. 'Stay there while I grab the paddle, you deserve to be spanked after moaning while I was putting the plug in.'

She stepped to the side and picked up the paddle, which was black and had the word 'SISSY' written across it in pink. She stood behind me again, grabbed a handful of my lace panties and pulled them up, wedging them in between my ass and exposing my cheeks to her. 'Such a nice little ass you have,' she teased as she ran the paddle up and down one of my cheeks. 'I think five swats on each cheek should suffice, don't you sissy?'

Then the first smack landed on my ass, I lurched forward as my cheek started to sting. I heard Mistress laugh before she pulled me back into position and hit me again, this time on the other cheek. Again, it started to sting but I didn't have time to think about it as she continued to hit each cheek simultaneously until she'd hit me ten times. By the end of it I was whimpering from the pain, both cheeks felt warm and were stinging. Mistress pulled me up right, so I was just on my knees and whispered into my ear, 'did you enjoy that?' She pushed the base of the plug into my ass, and I let out a little feminine squeak.

'Oh my,' she said, turning me sidewards so the camera had a good view of my side profile. 'I think my little sissy enjoyed that little spanking and the plug.' She pointed to my crotch, my dick rock hard and stretching my panties outwards. 'I think you'll enjoy having my dick inside you, won't you?'

'Yes Mistress,' I whimpered, looking into the camera.