When I was married, my ex wife never wore her lingerie, and I got the urge again, so I would put it on. I wore teddies, panties, anything she had that I could get into. Once, I wore her French Maid teddy with thigh high stockings out in public under my male clothes. I felt like I was more alive than ever. I was on fire. But I was also certain everyone at the store I was in knew.
After the divorce, when I was on my own, I again started feeling the urge. I spent a lot of time talking to online Dommes, and eventually bought some toys and some women's clothes of my own. However, just prior to moving in with a woman I'd known for a while, I purged, and, when I got back home after things fell apart, I had a low paying job and no clothes of my own to wear. I again went shopping, sometimes at dollar stores, sometimes at Victoria's Secret. I even had a friend send me a dildo, though it's a bit big for me to take inside me.
For the next five years, I shared housing with others, having nearly no opportunities to let the sissy inside me out to play. I longed to let her out so much that I started buying things again, including chastity. Even though my chances for using it were not good, I wanted it, just in case I got the chance to use it. Finally, that chance occurred. I even shaved my legs at that point, and I found that I enjoyed the smooth feeling. I again spent a lot of time speaking to online Dommes, making purchases and sneaking chances to take pictures for them.
I got speaking to an old friend who was also into it, and deleted all the pictures I'd taken for others, only having a few that I took for her. She initially wanted me to dispose of the panties I'd purchased, as well, but, I couldn't. I did not want to be without again.
Now, I've been speaking to a Domme again, and we've gotten a little more serious, speaking of Her moving into my house and making me her sissy cuckold. I'm actually looking forward to it. It's a path I've been tiptoeing around on for quite a while.