I’ve told my personal ‘dressing in lingerie’ story before.
When I was 19/20/21 I was fortunate to enjoy a relationship with an older woman who taught me an awful lot about sex, kink, and what I like. She was experienced, open minded and adventurous, which for a wide eyed boy like me was incredible.
We were at hers one evening just fooling around and she suggested I put her suspender belt and stockings on. Didn’t really do much for me but she seemed to enjoy and asked again a few nights later, while she had hers on. I will say the feel of the stockings rubbing against each other was nice!
Over a period of time it became a regular part of our fun, she bought me my own bra, briefs and suspenders set to wear (“to avoid me stretching here” she said, and it continued to the point of us going lingerie shopping for a couple of matching sets, matching basques.
There were two interesting developments then.
The first was where we would go out on nights out, to normal bars and clubs, with our matching lingerie on, me in normal going out clothes but say a basque and stockings on underneath, her matching. That would be so horny and would get us all worked up.
The second was that she would often ask to ‘make me up’ at home, so I’d put the lingerie on and she would sit in front of me doing full make up, truly feminising me. I didn’t get a particular kick from that, but she did, which I did get a kick out of!
I was young, dumb and full of cum as they say, up for fun, anything went.
We then went to PDI on holidays, to this day I swear it was an innocent booking on her behalf, not a play, but we discovered a side of PDI we weren’t expecting, which took us down a whole new route for our relationship- let’s just say this was when I discovered that while dressing wasn’t really my thing I was particularly drawn to attractive, feminine trans people…
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lets just say my eyes wonder a lot in the changing rooms 
