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By (user no longer on site) OP
over a year ago
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I've long had a bit of a thing for crossdressers, particularly younger (than me) slimmer guys. However, I've never really had an encounter with one although have met many younger bi guys over the years and even indulged in some mutual pantie wearing with them. I used to meet a guy regularly for daytime wanking fun who loved to see me in his young wife's panties. I once met a guy in his mid-20s who met me at his house and promptly took me upstairs to inspect his stem mum's undies draw. He wanked me off into a pair of her silky panties. Nice!
Anyway, this story is about a recent encounter where I finally got to meet a hot bi guy (Andy, when not dressed, Amy when dressed) who dressed fully and was open with his wife. He had a profile on here and messaged me and although he had a couple's profile it was clear that his wife (Sarah) didn't play. She knew (he regularly dressed at home), and she was coming round to the idea that he would like to play with a guy while he was dressed.
We had some horny text exchanges in which I got to see some pics of him dressed. He was clearly in good shape, about mid-30s, slim and did look pretty good fully dressed. One pic of him in a short skirt, tight blouse and with long blonde hair was very hot.
He said he'd only ever met one guy before and had had some mutual wank/suck fun. It went well enough he said but he wanted more. He wanted to be more intimate with a guy, really have a guy make love to him while he was dressed. I would get really hard when we texted about arranging an encounter like this (even though for me it would be a first time with a CD).
As we got closer to sorting something I asked if he could accommodate. He said yes.
"But your wife doesn't play?" I asked
"No but she will just stay in the living room while we play"
This sounded both strange and exciting. I quite liked the idea of being with him while she was nearby.
"And she's okay with this?" - I couldn't quite believe the set up he had.
"Yes. She knows I want to be with guys but is not a swinger and doesn't want to join in. She's isn't comfortable with seeing me dressed and with someone else"
"Tell me what she looks like" - I was getting hard at the thought that I might at least get to say hello to her when I went to see him.
Sarah's description got me very hot. Slim, brunette, late 20s, pretty, 34c. He said she was quite shy and although she loved sex she wasn't adventurous. Telling her that he cross-dressed was a big deal but she stuck with him despite misgivings. It was only recently, after years being together that they had had sex with him dressed. She was also helping him more when he dressed, making sure he looked good and helping him perfect his look.
To be honest, I was getting as turned on by the thought of Sarah as much as anything else.
We arranged a meet, for a week's time. We had lots of sexy texts in the build up. I was to treat him like a willing slut, tell him how to turn me on. He wanted to be fucked but I would be his first. If we got on, anything was on the cards.
It was then I pitched a suggestion that had been whirling around in my mind for a few days.
"I'd like Sarah to watch us."
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