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By (user no longer on site) OP
over a year ago
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Few years ago whilst playing with a neighbour, she opened my eyes to a lot... see "Naughty Neighbours" thread.
Anyway, one afternoon we were lay in bed after a rather steamy session, when she asked me about anything I'd like to bring to the bedroom.
So I told her that I loved the feel of women's underwear on my body and loved heels whether it was me wearing them or the woman wearing them.
I said that in the early days of being with my wife she had said how weird it was, a man wearing women's underwear and she wasn't into it... so I never mentioned the love of heels!
Upon hearing this, my FB said that if I liked I could leave some dressing up things at her house and as we were similar size her boyfriend would be none the wiser.
So we agreed that the following day we would go to Chester for lunch and go looking for some heels for me.
We went round some of the shops on the retail park and we ended up in Matalan, not the most prestigious shop, but plenty of choice and at bargain prices!!! lol
Anyway my FB picked out a couple of pairs she thought I'd like and put them in my basket and off I went to the changing room to try them on, I had some jeans and a shirt as well so it didn't look too suspicious.
Little did I know that while I was doing that she was already picking out some panties, stockings & a little summer dress, cheeky mare, wouldn't even let me choose my own.
So the next thing she's at the edge of the changing rooms asking if I'm ok, I stick my head out and ask her for a different size shirt, and she replies only if she can leave her shopping in my basket. As she walks over I open the curtains to reveal myself stood there in 5" heels and my tighty whitey boxers.
I felt so naughty.
If the assistant hadn't been knocking about I'd have pulled my FB in there and fucked her I was so horny.
Anyway when she came back with the new shirt I had swapped the shoes for the other pair, that were slight lower and I had put the dress on, my FB wasn't expecting this and her eyes nearly popped out.
I quickly pulled the curtain across and got changed again, making sure I'd got all my new clothes and off I went to pay. My FB was no where to be seen, I eventually found her back at the car in fits of laughter, she couldn't believe how brazen I had just been.
With that she suggested I should get changed in the car and drive home in my new dress & heels, I told her she must be joking, but she why not.
So we pulled over down a country lane just outside Chester and I quickly undressed and got into my new dress & heels, she told me I was not getting back in unless it was panties & stockings as well, so I did as I was told.
My FB was most impressed with the look and complimented me no end.
Well as you can imagine, my cock was standing to attention when I sat back down in the car, but it soon went down as I got used to the feeling of being dressed like this, one thing that was weird was driving in heels for the first time.
As we got nearer home I told my FB that there was no way I was ready to drive through our village dressed like this, so we pulled over at the back of the golf course and as I got out to change my FB got out as well and came over and kissed me, she pushed me against the car and put her hand up my dress and released my cock from my panties, I wanted to fuck her so badly, but she said no, she dropped to her knees and took my cock in her mouth and gave me one of her amazing blow jobs, so there was no need to clean up afterwards.
Once I was changed we drove back to hers and put all my new clothes in her wardrobe next to hers....
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