For those of you who have read the stories that I've already put on, you will already know a bit of my back story, but for those of you who are reading a story of mine for the first time, I will give a bit of background in the intro.
WARNING - This story contains m/f, pegging and some crossdressing.
So, for those of you who aren't aware, I've taken to writing some of my fantasies down and making those into stories, and this is another one of those. I started crossdressing when I was younger, and it started with the usual story of borrowing my mothers underwear when she wasn't around. Unfortunately this wasn't sexy enough for me and seen as though I didn't have a sister to borrow from, I ended up buying my own knickers. As I got older, this was able to expand and I was able to drive to buy more things and toys. But this story is based on the fantasy I've had for a long time. I hope you enjoy it, and comments and feedback is appreciated and I would be willing to work on more stories. No names used in this are actually real people.
I'd been buying knickers on and off for a number of years, unfortunately only being in my early twenties, I still lived with my parents and couldn't afford my own place. This meant I had to be very secretive and hide everything and only got the chance to dress on a night once everyone had gone to sleep. I'd recently gotten myself into a relationship which was going great but I also still had to hide Alexis (what I call myself when dressed) from her. I'd never had a relationship before and over the past few years I had begun to watch a lot of gay, bisexual and pegging porn. And the idea of being pegged really turned me on, I joked about it a few times with my new girlfriend and she wasn't interested in the slightest.
Anyway fast forward to the story, and the typical saying of just another day at the office comes to mind, only it wasn't really. It was a Saturday and I was working, even though I was only meant to be a Mon-Fri kind of person. We'd been called in to work on a project that was due the following Monday, all though because we hadn't finished it during the week, it seemed we'd be punished and have to work the weekend. Luckily there was only going to be three of us in, myself, Claire and Steve. Steve was a typical give a lazy guy a job, they'll find the quickest way to do it. Claire on the other hand was lovely and I'd had a major crush on her since the day she started a couple of years ago. She gave off the cute and quiet vibe, recently got the bug for tattoos and had split up from her boyfriend of a few years, although she never told us this, we were just assuming.
Claire was the kind of girl that I thought fit the bill of 'it's always the quiet ones' and that she wasn't really as innocent as she made out. She also lived at home with her parents but is a few years older than me. She had a lovely figure and a small but cute arse, everytime she bent over or walked past me I'd always find myself checking her out hoping to catch a glimpse of any kind of underwear that she might be into. The closest I ever came was a summer day a year or so ago, we were out for lunch as a team and she had a long black summer dress on, and as we were walking to the cafe I could just make out that she was wearing a pair of cheekies, it was difficult to focus on anything but her arse as we made our way to the cafe.
Anyway, Saturday morning rolled around and I jumped out of bed wearing a cute pair of comfy knickers. I would never normally consider wearing a pair to work as it would be too risky but since there was only going to be 3 of us in, I thought why not? So I slipped into a bright pink pair of lace shorts before throwing my jeans and a long t-shirt on just to make sure that if I needed to bend over, I could without risk. Once I was ready I made my way into the office, where Claire had already began to work away but there was no sign of Steve.
'Steve's not coming in apparently', Claire said.
'What do you mean?', I was furious. 'So it's just me and you to do all the work then?'
'Oh no, apparently he finished last night and has sent his stuff across.' Claire responded, loading the attachments from his email and it was no surprise to find that he'd done the bare minimum.
There was no point moaning about it, so we cracked on with the work in an effort to get done before lunchtime. Our desks were adjacent with each other so we could chat throughout the morning and we had a good laugh. Every time I moved, I was self conscious that she may be able to see my knickers, and at one point as I reached behind to pull my shirt out, I could feel an inch or so of the waistband of my knickers. I quickly pulled my shirt down and glanced over in her direction and she was looking at her screen, I think I got away with it.
We managed to get everything finished with most of our Saturday left and we began to pack up our things. 'Hey,' Claire spoke up. 'I'm having a few friends round tonight for some food and games if you fancy coming? Don't worry about getting home either if you have a drink, my parents are away so people are more than welcome to stay over.'
I had no other plans, and my girlfriend was out with her friends so I politely agreed and looked forward to it. We both headed home having a few hours to waste and I texted my girlfriend to tell her to have a good night and informed of my plans. The next big decision I had was to decide whether or not to risk wearing knickers under my outfit. I thought fuck it, I'm normally a shy guy but when I got home, I showered, slipped into a nice pair of white Brazilian knickers and even went as far as to risk wearing a suspender belt and attached my stockings. I threw on a t-shirt that I tucked into my jeans and then a oversized sweatshirt just to cover myself. I had a quick check in the mirror for any lumps or bumps from the suspender belt and headed to Claires.
Once I got to Claire's, I knocked at the front door of her house and she let me in, there was a few people from work who were there and some of her own friends, which she introduced me to. Everyone seemed lovely. I mingled but mainly ending up sitting with the guys from works, we all had a few drinks and some food and chilled out after a stressful week. I didn't drink much and as the party started to die down a little, most people from work left early to head home which kind of left me sitting on the outside listening to Claire's friends. They'd planned to go out and hit the town after leaving Claire's. By about 11.30 everyone had upped and left, I stuck around to help Claire clean up before I was going to head home myself.
Helping Claire tidy up meant there was a lot of bending down, squatting and reaching up to put stuff back into the cupboards. While I was doing this, I was constantly checking Claire out who was wearing a pair of Mom jeans which were quite baggy and a black t-shirt with her favourite band on which showed off a bit of her flat stomach. I watched her as she bent down and one point and I got the tiniest glimpse of her underwear which was amazing, it looked like lace but I couldn't be sure, and then at one point when I bent down to pick up some empty food wrappers from the floor, I thought I heard her giggle a little bit and panicked, but when I turned round, she was looking at her phone. I was extremely paranoid.
'Right then, I'll get going seen as though everything is nice and tidy!' I said as I headed to grab my keys.
'Oh come on, why don't you stay for another drink? It's shit being home alone, especially when your single!' Claire seemed a little down since her break up so I decided to stay for one more drink while we sat and chatted on the sofa. I was starting to see a different side to Claire, she seemed to be almost flirty, I knew she'd had a drink but she was probably tipsy at best, I'd seen her drunk and she was nowhere near that. Then the conversation turned to her relationship and her break up with her boyfriend Adam, it almost seemed like she was getting herself upset by talking about it but then she started talking about how it'd had been months since she'd been fucked and how her toys weren't doing it for her anymore.
I had to reposition the way I was sat as her talking about this had caused my dick to get harder than it had before. I didn't know how to react to the conversation, part of me felt uncomfortable because I had a girlfriend but then the other part of me was more turned on now than I'd ever been. After a short period of silence, Claire then asked the question that made me want the world to open up and swallow me.
