After several years of wedded bliss and no cross dressing, I felt like I had successfully put it behind me. I still thought about it from time to time, but I was OK with wearing mens clothes.
One day we were in a sex shop buying some toys and she picked up with cheap little one-size-fits-all skimpy thong and asked me what I thought. I joking responded that I would look great in it. We ended up buying it and I occasionally wore it during sex. But it wasn’t very comfortable and I never felt any temptation to wear it other than during sex.
I always kept my history with cross dressing secret from her. I had no doubt that she would be fine with it. She was very open minded about these things. But I still wanted it to be my secret.
One random afternoon we were driving somewhere and she commented that she needed to buy some new underwear. I added that I could also use some new underwear. She responded that it was easier for me because I could just grab a three-pack of what I wear, but she had a lot more options to choose from. For some reason at that moment, I decided to just come out and admit something I had been keeping secret for so many years. I said, “I know it. I wore panties for years.”
She seemed briefly confused, and asked what I meant. I explained that I actually wore them like regular underwear. She had several follow up questions. Not anything really judgmental, just curiosity. I answered her completely honestly. I figured the cat was out of the bag, I should just admit whatever she wanted to know.
When we finished talking about it, she said she didn’t understand why I stopped wearing panties. She said she thought it would be sexy and wanted me to start wearing them again. I gladly agreed. That same night we went to a store and she bought some panties for herself and I got some for me. She was excited when we got home and got to watch me put them on. I admit I was excited too.
Almost immediately I started wearing nothing but panties. It really felt great to get back into my underwear of choice. And it all seemed very normal. There was nothing awkward about separating my panties from hers when folding the laundry. It just felt like my normal underwear.
It progressed somewhat slowly. One day she was talking about putting on some nice lingerie to be sexy for me and I said that I wished I had some nice lingerie. She went looking through her lingerie to see if she had anything that would fit me and didn’t really come up with anything, but then suggested I could at least put on one of her bras. As soon as she saw me dressed in bra and panties she commented that she liked it and thought I should wear bras more often. That same day we went out and bought me some bras.
The next morning I was getting up to walk the dog and I threw a t-shirt on. She stopped me and told me if I was going outside I ought to have a bra on too. I realized she was taking this pretty seriously and from that day on I wore a bra from the moment I woke up until the moment I went to bed.
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