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Crossdressing Husband/Boyfriends

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By (user no longer on site) OP   
31 weeks ago

For those crossdressers lucky enough to have a partner who is into it, how did you first bring it up? I want to try it with my girlfriend but don't know where to start. I honestly think she'll be open to it, but still very nervous.

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By (user no longer on site)
31 weeks ago

I had been wearing stockings and lingerie long before I met my wife but had never brought the subject up with her. It wasn't until we started swinging that I thought I might might get away with suggesting it.

A couple we had been meeting for a while led to the conversation as I had mentioned to the other woman that I'd love to wear stockings when we met. Unbeknown to me this woman mentioned it to my wife one evening in the pub. My wife said nothing to me about it at the time.

We had arranged a session with this couple for a particular evening and my wife mentioned that there's something in the bedroom I might like. I went upstairs to find a matching set of suspenders and panties and some stockings in my size (my wife's wouldn't have fitted me),so I quickly put them on and went back downstairs.

Paul and June arrived and we had a couple of drinks (we were in the pub trade at the time) at closing time after everyone had gone we paired off as usual, with June saying I hear you have a surprise for me tonight

Anyway that's how my wife found out and dealt with my dressings, over several weeks my dressing became more and more full on until I was dressing fully for our swinging engagements. This of course led to other things like my wife doing MMF sessions but I was never the second male, fun times and great memories

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By (user no longer on site) OP   
31 weeks ago


"I had been wearing stockings and lingerie long before I met my wife but had never brought the subject up with her. It wasn't until we started swinging that I thought I might might get away with suggesting it.

A couple we had been meeting for a while led to the conversation as I had mentioned to the other woman that I'd love to wear stockings when we met. Unbeknown to me this woman mentioned it to my wife one evening in the pub. My wife said nothing to me about it at the time.

We had arranged a session with this couple for a particular evening and my wife mentioned that there's something in the bedroom I might like. I went upstairs to find a matching set of suspenders and panties and some stockings in my size (my wife's wouldn't have fitted me),so I quickly put them on and went back downstairs.

Paul and June arrived and we had a couple of drinks (we were in the pub trade at the time) at closing time after everyone had gone we paired off as usual, with June saying I hear you have a surprise for me tonight

Anyway that's how my wife found out and dealt with my dressings, over several weeks my dressing became more and more full on until I was dressing fully for our swinging engagements. This of course led to other things like my wife doing MMF sessions but I was never the second male, fun times and great memories "

That's very hot, you're lucky to have someone like that x

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By *ickylouCouple
31 weeks ago

Bi

Suppose we are luck as We just talked openly about anything from the start of our relationship

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By *andy57TV/TS
31 weeks ago

york

Mine was a doctors and nurses party the fact my wife was a nurse she was able to get a uniform my size.

On returning home we had the best sex ever and she knew it was down to the fact I was dressed fully and it went from strength to strength

She would help me with putting makeup on how to dress correctly what suited and what didn't. How to sit correctly and best of all how to walk in heels. We used to meet as a couple with others and also visit clubs

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