Crossdressing and Voyeurism

I’ve secretly crossdressed since as early as I can remember, firstly with my mother’s underwear, stealing panties whenever I got the opportunity and gradually building up my collection until I was able to buy my own, not inconsiderable secret stash.

As I got older, I found risky crossdressing in public places a massive turn-on and developed a special interest in voyeurism.
Some of my most erotic memories are of being parked next to a couple having s** in their car, with me stripped down to my lingerie playing in time to them and climaxing with them.

Later on in life, when I had friends stay over, I’d silently dress in sexy lingerie and lie in bed hoping to hear them have s**, it was and still is a huge turn-on for me.
I later bought a cheap room bug from eBay so I could listen more intently to my guests having s**, the quality was amazing, you can hear even the slightest breath!

Now, my rooms are all rigged for listening and towards the end of the evenings when I have visitors, I usually put on a sexy basque under my normal clothes so I’m prepared for bedtime.

If I’m feeling particularly h****, I attach my suction cup d**** to my headboard and lube it for immediate use.

Normally, within a minute of closing my bedroom door I’m stripped off and on my hands and knees, d**** just touching my ass, waiting for the s** noises to start so I can imagine it’s me getting f***** as I slide it inside.

A couple of weeks ago, I had a friend stay over for the weekend and by around 11pm we were both quite drunk and ready to call it a night.
I’d been feeling brave earlier in the night and was wearing a red basque under my shirt and jeans with matching panties and stockings for most of the night which really made me squirm.

Just before bed, I decided on a risky change of undies and put on a white Rago six-strap girdle, full satin panties and new white lace-top stockings.
I was going to leave it there but decided to add rather stiff longline bra too to complete the look.

Everything showed through my shirt so I slipped on a hoodie and ventured back to join my friend.

I thought everything was fine until we called it a night and he gave me a drunken hug.

I could feel his hand touch my thick bra strap through my hoodie and his hand trace it up over my shoulder when we parted.

He then patted me right on top of my bra twice before saying he was going to turn in for the night.

Nothing was ever mentioned but I knew he knew as when I went to my room, under a bright light, my bra was completely obvious, pushing through my hoodie.

My desire for risky crossdressing seems to be getting stronger, I’m writing this wearing a red basque and I’m about to drive to some forest car parks, strip down and take some pictures!

XX

11 Comments

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  • I too love to go out with stockings and sexy panties on under my woman's jeans and to wear a sexy matching bra and my small breast forms under my button up shirt. I know it shows and don't care. I love to shop like that for woman's cloths like that too.

  • I think it's cool! I've been wearing my sister's panties and stuff. Now I've got some of my own. I like wearing short cutoffs so that the pan9 can show when I want them to.

  • We both share the passion for wearing silky ladies lingerie with a possibility of being seen. I go shopping in a worn thin tee shirt & and a pair of shorts while wearing done silky slip short panties and a pair of Sheer Energy Nude pantyhose, a high waist control panty, & a regular close bra with nylon cups that's white. The bra shows thru the tee shirt cause it's white and of course the thin tee shirt clearly shows the bar's outline. A lot of women look me up & down and give me a smile like they're saying I see you wearing ladies underwear. So very exciting. Still I don't have the courage to wear my colored tights under my shorts.

  • I too remember as a young boy wearing tights and really finding it arousing and relaxing in a prepubescent way. I also liked to wear plastic pants with the plastic against my skin. Also I liked to wear multiple pairs of undies. I think tight clothes were one thing.

    Every now and then mom would catch me doing some new kinky thing. I'd always be super embarrassed but she was always really nice and supportive. She'd buy me tights and a leotard and suggest I sleep in them or wear them under my boy clothes.

  • I wish my Mom had agreed to let me wear silky girls panties and tights. Instead I had to sneak them as a kid.
    I'd also invite a bunch of the neighborhood's boys & girls to come over during the summer and watch me dress up in all of Mom's silky underwear. Everybody loved watching me model Mom's panties, garter belt & stockings, her short half slip and her bra.

  • Wow you were brave. I was totally embarrassed of myself

  • I find cross dressing a huge relief slipping into my panties basque stockings high heels get me so aroused first time I was so aroused couldn't wait to dress up my c*** was straining through my silk panties feeling my stocking clad thighs I came so hard and heavy covered my panties and c** oozed through the fabric.

  • Sounds lovely. I enjoy wearing panties and bra on occasion. Even pantyhose or stockings. I will venture out to the store no one sees or knows what I have on. I get very h**** doing that. One day I wore a little bra with only a T-shirt over and went to Home Depot. I was so damn h**** the entire time. I’m pretty sure it was visible to those that were looking for it.

  • I wish I had a friend like you so we could both go shopping while wearing all sorts of sexy lingerie that could be seen thru our clothes, or how about wearing stockings with a pair of shorts. I went to my bank and spoke to a lady while dressed like that. As she watched me come into her office she looked at my legs and smiled. I almost came right there.

  • I like wearing pantyhose and panties but not outside the house. I like to open up the back of the pantyhose so my ass is exposed. Then I like taking pictures of myself. I used to go out with a girl that didn't mind me wearing pantyhose around the house.

  • I both emphasise and sympathise

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