Caught Out at Work

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.

'So when did you start wearing womens underwear?' She asked. Immediately I think she could see my panicked reaction, I didn't know where to look before she rested her hand on my thigh probably feeling the straps of my suspenders at the same time. 'Don't panic, I'm not going to tell anyone... I'm not gonna lie, the thought kind of turns me on a little, and when I seen you at work...'

I cut her off, 'Wait! You caught me at work? When?'

'Awww, I seen those cute pink knickers you had on today at least a hundred times'. I was mortified. 'Every time you leaned over or bent down, I could see them! It was obvious, I thought you wanted to get caught.'

'Oh shit!' I was frantic. 'You can't tell anyone, please. My girlfriend doesn't even know I do this...'

She stopped me again, slowly rubbing her hand up the inside of my leg. 'Don't worry, I'm not going to say anything. Like I said, I'm really turned on right now and would love to see what you wearing right now, I sense it's a little sexy' And with that she grabbed a hold of one of the straps through my jeans and let it twang back against my leg.

Despite the fact she'd found out my biggest secret, she was putting me at ease really easily and the fact she'd been rubbing my leg for a few minutes now meant I was now sporting a sizeable erection in my jeans which was covered by my position. 'Well, I can't lie Claire, I've always had a thing for you since the day you started.'

Her hand moved across the front of my cock. 'I like you too, always have. And now I've had a feel of this...' She gripped my cock. 'I want you even more, now come on, show me what you've got on underneath those clothes.' She leaned in towards me and kissed me, sliding her tongue into my mouth and I couldn't resist and immediately kissed her back, my hands now roaming all over her body, grabbing a hold of her ass whilst she fumbled with my jeans, popping open the button and sliding my zip down.

I pushed her hand away, 'the only way you're seeing me in my underwear, is if I get to see you in yours', I told her. Figuring this may delay her tactics as she might not be being completely honest, I was very wrong. She quickly jumped up discarding her t-shirt revealing a cute lace bralet that offered her no support and could see her small but perky tits jiggling as she unbuttoned her jeans and whipped them to the floor in one motion. She was now just in front of me wearing her bralet, a matching pair of cheekies, although I was guessing as I hadn't seen the back and her socks.

I couldn't take my eyes off her, she looked incredible and it was the first time I'd seen her tattoo that she'd had done on her thigh. I was soon brought back to reality when she pulled me up off the couch and before I had chance to prevent anything she already had my sweatshirt up and over my head and had my jeans already half way down my thighs. She quickly rubbed her hand across the knickers that were struggling to contain my erection. She sat back down on the couch and instructed me to take the rest off. I gingerly stripped out of my jeans, removed my shirt and socks. There I was dressed in lingerie in front of a girl I had a crush on for years and she liked it.

'OMG, that's such a cute set, but kind of slutty at the same time... come on give me a twirl.' I quickly spun around, letting her see it from all angles. 'Oooo nice, I'm not even lying, I think I have the same pair of knickers. New Look aren't they?'

'Yeah', I responded, I couldn't believe what was happening, my face must have been all shades of red but I couldn't help but be massively turned on by it.

She then dropped off the couch and onto her knees in front of me. She freed my cock from inside my knickers and slowly began to stroke me, all the way from the base of my cock to the head.

'Oh my, you don't know how long I've waited to get my hands on this.' She slowly stuck out her tongue and licked the tip of my cock before licking all the way down my shaft and using her tongue to work my balls.

I could do nothing but groan, the pleasure almost causing me to lose my balance, I had to quickly grab onto the arm of the couch to make sure I didn't buckle. Claire just laughed before standing up, 'come with me, lets get a bit more uncomfortable.' And with that she took my hand and led me out of the living room and upstairs to her bedroom, the whole time my eyes were fixated on her ass as it swayed from side to side in front of me.

Once in the bedroom she closed the door behind us and I pinned her against the back of the door before kissing her once again. I broke off the kiss and began to nibble and kiss her neck as I my hand worked its way down her body and began to gently rub her pussy through the material of her knickers. Causing her to moan I could feel the lace between my hand and her pussy was getting wetter every second as she reached out with her hand and took hold of my cock and began stroking. Our moans filling the room before she pushed me away and told me to lay down on the bed.

I got myself onto the bed whilst she went to her drawers that were next to the bed. She put some quiet music on and then joined my on the bed placing herself between my legs... she'd brought something with her but I couldn't quite make it out. Claire then removed my knickers, leaving me in just my suspender belt and stockings. She took my cock into her mouth and her head was bobbing up and down on the end of my cock. With her free hand, she worked it down below my balls and brushed her fingertip against my ass hole. She then removed it and returned it a few seconds later only this time there was a cold sensation as she pressed her finger into my ass, slipping it inside me with ease and she slowly began to work it in and out before taking her mouth away from my cock.

She started talking to me as she worked her finger in and out causing me to moan and groan with every thrust. I'm not sure if I'd be able to respond to the conversation she was about to start, I was in heaven with the pleasure as she worked one hand on my ass and the other stroked my cock.

'You see, the reason me and Adam actually broke up was because I was probably a bit too kinky for him. I really wanted to try pegging but he wasn't into it, I tried to play with his ass once and he hated it,' she said. 'Next thing I know I'm single.... and here we are now.'

'Oh.... fuck....' I could barely get my words out. 'I've always wanted to try that.' I managed to say through every groan caused by her finger pressing into me.

'Well today's your lucky day.' She pulled her finger out of my ass and it was replaced by something a lot larger but penetrated my asshole with ease. At some point she must have slipped herself into a harness with a dildo attached. With that she began to thrust causing a groan from me every time.

'Oooooo this isn't your first time playing with a dildo is it babe?' She asked.

She pulled out of me and flipped me over so she could fuck me doggy style. She quickly had her strap on back inside me and fucking away at my ass. She grabbed a hold of my suspender and really began to pound my hole now.

'Ugh.... fuck.... feels.... so.... good....' This was everything I'd fantasised it would be. Being fucked by a beautiful woman.

'I'm going to get you back for this... just you wait.' I laughed and said as she was fucking me.

She then pulled the dick back out of my ass which caused me to let out a whimper. She gave my ass a slap and then spun me back over again. I was being controlled... dominated... by a woman who was probably half my size and I didn't want to be anywhere else right now. I was so turned on. My cock standing straight from my body as she re-entered me in the missionary position.

I think Claire was loving it just as much as I was as she began to stroke my dick again whilst she was fucking me. I was trying to stay as quiet as I could but it was impossible. The pleasure of her rubbing my prostate with every thrust and her slowly stroking my cock was bringing me to the edge of an orgasm. After a few more powerful thrusts I couldn't hold back anymore.

'Oh shiitttttt........ I'm gonna......... cummmmmm.' I barely got the last word out before streams of cum erupted from my cock straight into the air, some landing on my chest, others landing on the bed. She continued to stroke my cock, milking all the cum out of me before removing her strap on from my ass and bending over my cock and cleaning my cock of cum before working her way up my whole body using her tongue to clean all the cum that had landed on me.

She got out of the harness and rejoined me on the bed, still dressed in her lingerie. 'Well.... that was amazing,' she said. 'I'm gonna invest in one of those double ended dildos for next time.'

'Well, I hope we're not finished for tonight.' I said, 'I've got things I'd like to do to you, you know. What you just did was amazing... and it's now time for me to repay the favour. I stripped out of my lingerie and rejoined her on the bed, somehow I was still fully erect!

She propped herself up near the top of the bed, laying there looking incredibly sexy in just white lace lingerie. I climbed back onto the bed and started by kissing the tops of her feet, before kissing her ankles and working my way up her body, stopping at her pussy to pay it some extra attention. I kissed the insides of her legs before planting a gentle kiss on the top of her pussy, causing her to let out a slight moan.

'Oh fuck, oh fuck, oh fuck.' Her head was tilted back, gripping the bed sheets with both hands, clearly enjoying the pleasure I was giving her.

I continued to kiss my way up her body, slowly teasing her, kissing around her stomach causing her a little giggle as she was obviously ticklish. I finally reached her beautifully small tits and found her nipples immediately, gently biting down on one of her nipples which caused another massive groan whilst my other hand massaged her other breast. I then continued to move up her body, kissing her neck again. Now my cock was pressed against her pussy, only separated by the delicate lace of her knickers. I slowly began to rub myself against her as we kissed.

I once again worked my way down her body, kissing a trail down the centre of her body before hooking my fingers into the waistband of her knickers and slowly pulling them down revealing her pussy for the first time and her cute little landing strip just above her pussy. I threw her knickers to the side of the bed and gently began to kiss around her pussy causing a little whimper and moan with every kiss. I then began to eat her pussy, both hands grabbing and massaging her breasts as she gripped onto the bed sheets and began to squirm.

'Oh..... fuck..... it feels so good, its been far to long,' she said.

Because she was squirming so much, I had to move my hands to underneath her legs and keep them open to stop her closing her legs. I was now using my mouth to attack her clit; licking, sucking and gently nibbling around her sensitive areas bringing her to the edge of an orgasm and quickly. She tasted incredible, juices pouring out from her pussy as I lapped them all up, her body starting to shake and tense up.

'Don't you FUCKING dare stop.... I'm so close right now!' And with that she put one of her hands on the back of my head forcing me into her pussy.