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Gilli CD - my oldest photo - The first time crossdressed Just before covid, in the fall of 2019, the wife and I did our yearly trek for a week at a ski hill in the mountains. We had made a bet on the Grey Cup that year that I had lost and to repay my wager she said she had something she wanted us to do when we got to our condo in December. The surprise was dressing up for her. Had never done it before and had never thought about doing it in my life. I said sure. It was way more fun than I thought it would be. Eventually during covid, we’d have a once a month or every other month “date night” where we would both get dressed, have a few drinks and enjoy each others company. This picture is near the end of the night when we decided we should hop into the hot tub on the balcony of our unit. For context, she’s 5ft 8 and 125, I’m 6ft4 and 225. Those aren’t her clothes. She bought and brought them. The very limited wardrobe i have is mine. I don’t wear her clothes. Anyways, here it is.  |
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You would make a good woman does your wife peg you at all?
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No. Not femme/sub or sissy. Not into anything like that. Just crossdress for fun.
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i like it you look great
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Very HOT!!!!!
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Well your doing a great job its great that your wife supports and has fun with you l wish you both great and long lasting happiness, enjoy your day
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I have always said, I would wear a dress for he right woman. It is mostly a concept to having the full trust and openness one can have with a partner. Probably would never be asked to to do such, but for the right woman I would if asked, For the fun of it! "One Big Sky Covers Us All Equally"
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If it was FOR, WITH fits in the concept too. "One Big Sky Covers Us All Equally"
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