When did you start wearing women’s underwear

I started when I was 11 or 12 years old, Started wearing My Mothers Corselette and stockings, Heels Etc.

Got Caught by Her a few times which didnt go well !.

As I got older and started working I could buy my own items of Lingerie, Always with the Excuse that they were for My Girlfriend (did they believe me ?).

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@paulsballs lucky guy there I bet that was a nice treat for you.

@Vannesatart it was the same me that’s how I got started, got caught way to many times which no it didn’t go down to well back then. Then soon as I had a job, my own place and gfs it was great. Some gfs were ok with it but my wife ain’t keen which is a shame

We took a decision this week and threw out all my men’s underwear.

All my briefs and boxers are gone now and I only have women’s knickers in my drawer so I’ll be permanently in womens underwear for the foreseeable future.

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All mine were thrown out a year ago too.I did have one pair of boxers i found about six months ago and tried them for a few hours and could not wait to get back home to get into a nice sexy pair of frilly knickers.

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I started pretty much when puberty hit I think, then did it less as girls became more accessible when I could go out to pubs and clubs. When my kids arrived and our sex life tailed off a little I started again, in secret, an exclusively solo thing. -and one I’d never told her about; it tailed off again then we hit a rough patch and I thought “fuck it, why not just be honest and happy?” Came walking out of the bathroom one morning when we were on holiday in stocking, suspenders and a thong, 6” heels, and confessed everything. A bit shocked she was, but we’ve never looked back, and are having more fu together now!

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This exactly the same situation as me, but haven’t got the guts to wear them in front of her