Confiding in My Hairdresser

I've always had a great relationship with my hairdresser, Mary. She'd been cutting my hair for years and we probably shared a few more details than we should about sex, she made me laugh at some of the naughty stuff she'd been up to!

On occasion around a year ago, she came to the new house that I'd just moved into with my girlfriend to cut my hair.

The chair was facing the back garden where I could watch my girlfriend pottering around as she got to work.

Sensing she was a little quiet, I asked her what was wrong and she told me that she'd just found out that her brother was getting divorced and she was quite angry about it.

I asked why she was angry about it and she told me her sister in law had discovered that her brother liked to crossdress and had massively overreacted, screaming, crying and telling all her friends and anyone who would listen about her husband's sick secret.

She told me she couldn't see what the problem is, in her mind, it's harmless and her sis in law should've embraced it and introduced it into their sex life.

She then told me that her and her boyfriend occasionally had drunken sex with him wearing her panties and she actually found it a fun little treat!

On hearing this, my cock hardened as I had the urge to confide my little secret to my hairdresser and I discretely shuffled around so my fingertips could press on my cock as she worked.

Heart racing, I asked her what exactly her sis in law had found out. She told me she'd found his lingerie stash and confronted him about it. He came clean, saying he loved the feeling of lingerie on his skin and how he sometimes wore stockings and panties under his work clothes.

On hearing this, I blurted out "fucking hell Mary, we're going to have to change the subject because if my girlfriend comes in, she's going to wonder why I've got a massive hard-on!"

She said "ooh, you two share the same hobby then?" and started laughing.

She found my embarrassment quite amusing and kept mentioning items of lingerie close to my ear to watch me squirm.

She then asked if my new girlfriend knew about my little hobby. I told her all my stuff was stored in the garage roof and I had no opportunity to indulge as it was behind a ton of other stuff. I told her I missed it very much.

She said she didn't mind me wearing sexy undies underneath my normal clothes when she was cutting my hair and I told her that in the past, I'd already done it! She asked what I wore and I told her I wore a black six-strap Rago suspender belt, black lace top stockings and black lacy boy shorts amongst other things!

Mary found it all very interesting and asked many questions about why I liked to dress in sexy lingerie and how I felt when I was dressed up. For the first time ever, I opened up about my love of crossdressing to another human. I loved it, and I loved the feeling of vulnerability and humiliation I felt.

Needless to say, I was extremely horny when she left and immediately went upstairs to grab a pair of my girlfriend's panties out of the washing basket to quickly cum into. Unfortunately, she was tiny and her underwear is miles too small for me to enjoy.

The next time I had a haircut, we never mentioned the subject until she reached in her bag and gave me a pressie of a pair of white, frilly lacy panties that she'd bought for me earlier in the day. The thought of her looking at lingerie and thinking what would suit me (and buying it) got me so excited that I was trembling and lost for words. She could see I was excited, laughed and said "go, on, go and put them on then!"

I came downstairs a few moments later with my new panties pulled tight against my balls under my jeans.

Mary played on my obvious excitement and teased me at every opportunity during her stay which I made no secret of showing my enjoyment.

I told her that I'd made an internet friend, a much older woman from the north who enjoyed my crossdressing and encouraged me to do it.

She would email me tasks and I had to email pictures to prove I'd complied.

It started out with small things like taking a pic of me filling up with fuel at the petrol station, my shirt unbuttoned revealing a bra or basque to much more risky stuff.

Mary listened intently, seemed intrigued and asked for more details so I told her the day before, I'd gone into the toilets at my local mcDonalds and locked myself in a cubicle. I then had to set my phone up to video me slowly and silently stripping naked and folding my clothes into a neat pile.

Then I took a bag out of my pocket which contained a red basque, red seamed stockings and red thong.

I sexily slipped it all on, extremely excited at the voices so close to me with no idea what I was up to.

Once I was perfectly dressed, I had to turn away from the camera, lube up a butt plug and slowly insert it making no sound.

I loved hearing people going about their business so close to me but unaware.

I then got dressed and left before taking my jeans off in the car and driving home with my stocking tops, panties and suspenders on full show.

Mary then asked if I wanted to take a picture now, with her near me. My heart skipped a beat as she turned away, allowing me to drop my trousers and take pics of me in panties with her in the background.

Since then, she regularly sends me pictures of lingerie sections in department stores whenever she's around them asking if I see anything I like, knowing it drives me wild!

For birthdays and Christmas, she always buys me sexy suspender, bra and panties sets, it's incredibly exciting and as of yet, there's been no sexual contact which adds to the excitement!

More stories to come...

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