Caught crossdressed

Years ago I had a bit of a fling with my cleaner. It led to nothing but we were grown up about it and remained very close friends afterwards, her still working for me to this day.
She knew I was a bit kinky and I used to leave all manner of things around the bedroom for her to discover and tidy up, I got a kick from knowing she’d seen them and put them away in their correct drawers or boxes.
It started out with plugs, d***** or vibrators left at the side of the bed and then the odd stocking or pair of panties in the bed which she sometimes mentioned, usually that my “latest conquest” had left her underwear here.
I used to joke that they were mine but the truth is they were in fact mine!

My crossdressing had always been a completely private pursuit but as I got older I became more relaxed about it and fantasised about being caught while dressed in lingerie or even the turn on of sharing my kinky secret with someone which probably explains why I left lingerie around for my cleaner to find.

It became a regular thing for me to leave different items of lingerie around (all my size, 38b and size 16!) for her to discover. She progressed to sometimes commenting on how pretty it was as she held it up before neatly folding it up. Sometimes she’d shout from the bedroom and ask if these panties and stockings needed putting away or putting in the wash. They always needed the wash!

Just to make sure there was no ambiguity I started to leave specialist crossdressing items out for her to find, lace panties with sheaths and lace teddies with a pouch at the front for male genitalia to fit, all of which were neatly folded for me.

I also left some magazines for her to find on the nightstand, humiliated house husband story books and selections of transvestite and sissy magazines full of glossy pics of beautiful crossdressers.
Whenever I left magazines I’d always go out for an hour or so and wonder if she’d read them or flick through them. They were always stacked neatly when I returned.

On one occasion I left my satin French maid sissy dress on the floor (obviously my size) and a pack of stick on French manicure nails beside it.
The maid’s dress was found hanging in my wardrobe next to my jackets and the nails in my top drawer with my underwear!

That’s the background, here’s the story:

Last Tuesday she was here as normal but I was feeling very h**** for some reason so I’d left my grey basque, matching lace panties and seamed grey stockings by the side of the bed. The suspenders were still attached to the stockings so it looked like they’d been taken off in a hurry which they had as I’d slept all night in them and hurriedly took them off to get showered before the cleaner arrived.

I was still very turned on after my shower so decided that I was going to wear lingerie under my clothes while my cleaner was here, something which I’ve done many times before as I love her not knowing what I’m doing and it drives me wild!

I decided on a very thin black lace bralet that wasn’t obvious under my polo shirt, a black 4 strap Rago suspender belt, lace panties and tan seamed nylons which I adjusted to perfection in the mirror before sliding my jeans on and slipping on my polo shirt. I love the feel of lingerie under my clothes.

As she arrived I was on Wish shopping app on my ipad browsing some specialist transvestite underwear and silicone b****.
Whenever I thought I could get away with it and not get caught, I would quickly unbutton my jeans, pull my top up and take selfies of my risky crossdressing antics to file later in my secret picture folder.

I was glad when she asked for my credit card and left to pick up some shopping for me which gave me 30 minutes to take some more pictures and watch some sexy sissy movies on my own!

When she finally arrived back I was fit to burst and happy to usher her out of the house so I could have some fun.

She’d barely got to her car by the time I was selecting my next outfit.

I stripped off completely and selected a very feminine pink bra panties and suspender set and some sexy black lace top stockings pulled up very high on my thighs.
I also added a push-up cleavage creator bra that gave me amazing b****. Very uncomfortable but delightfully restrictive!

When I was happy that everything was adjusted perfectly in the mirror, I took my time to insert my favourite plug to make me feel full, cleaned up, slipped on my patent black 5 inch heels and strutted around the house, loving the feminine feel and sound and feel of my heels on the wooded floor.

Next I sat down and applied the sticky pads to my nails and carefully attached the nails one by one. I love looking at my hands when I have false nails on, they make me act and feel so sissy.
Normally when I’m feeling this feminine I put on one of my maid’s dresses and do the housework while videoing or taking pics of myself in feminine poses.
After the nails I put on some clip-on dangly earrings which I love the feel off, some oversized rings and some bangle bracelets which jangle at my every move.
To top the look off I slipped on a very flimsy French maid fancy dress costume that was very see through and very short, all of my undies were visible through it!

I moved a large mirror so I could see my reflection from where I was going to sit on the sofa, slightly off to one side, made sure my b**** were adjusted to maximum cleavage then placed my iPad on the arm of the sofa and started to play and surf sexy sissy videos.
I love to hear the audio in the videos that I watch, it’s very important to me so I put on my headphones and turned up the volume.

I had a lovely time running my hands all over my lingerie, crossing and uncrossing my stocking legs and admiring how my stilettos hung so sexily off my feet.

I had no idea how long I’d been indulging but suddenly I noticed something from the corner of my eye which made me turn around in shock.

Standing there with her hand over her mouth was my cleaner staring at me, eyes wide.

There was nothing I could do, I froze.

She said “I’m so, so sorry, I forgot to give you your credit card back so when there was no answer at the door I thought you were out and let myself in, I’m so sorry!”

After what seemed like an age, I started to apologise to her but she interrupted and said she knew I liked this sort of thing but never thought she’d ever witness it!

She then walked to the kitchen to put my card on the work surface where she normally left it and jokingly said “I’m guessing you don’t want me to make us coffee then?’

I was mortally embarrassed and stood up, covering my modesty as I did. I towered over her in my heels, she looked me up and down still smiling and said she’d let herself out and for me to have fun!

As she turned to walk away i felt her hand run over my hip and to the top of my leg which felt electric! I couldn’t make eye contact with her.

I had a wonderful night that night feeling h**** and humiliated at the same time but I’m dreading seeing her next week!

1 Comment

  • newest
  • oldest
  • most replies
  • most popular
  • Now I need to put on my pantyhose and heels so I can enjoy myself too!

Account Login
Signup
Is this post inapropriate?
Is this comment inapropriate?
Delete this post?