My wife caught me dressed up. We weren’t married and had just got engaged. We were in Mexico and she’d gone out. I had been eyeing up a particular set of bra and panties of hers and being in the laundry I didn’t think there would be an issue in me just trying them. Of course before I knew it, I had on one of her skirts (black) and shoes that had a small kitten heel. I was just about to choose a top when the door to the hotel room opened and in she walked. Shortly after, having shouted and with me begging, she walked out. Sometime later she returned and had me dress up again, which was awesome on my part. Eager to calm the situation, I obliged immediately. We talked and I told her everything and that I’d been dressing for 14 years (at the time) we ended up having sex with me dressed up, which was amazing and unfortunately I didn’t last long.
We got married and she even dressed me up on our honeymoon, makeup and everything, which was a first. Again we had sex and I slept in my lingerie that night. Over the years we’ve had some amazing times but never have I dressed fully with her. That was until July this year, she bought me my first wig and we spent a night away. I’d bought new lingerie, outfit and shoes, she’d bought me makeup, false nails and a wig. Unfortunately, the pressure of the situation got to us and we ended up arguing with her saying some hateful things. I haven’t dressed up with her since and all my old secretive ways are creeping back in