Despite that, I still didn't honestly think it would work. I was still really angry with her. Around the end of the first month, we talked it through. I explained that as much as I had enjoyed it, I didn't believe it was going to work. She was devastated. A couple of days later, when we were in bed, she asked me shyly if maybe the problem was just that there were things I wanted that she wasn't doing. I thought it through for a while, and then admitted that perhaps there was one thing.
I was a bit uncomfortable telling her this stuff, but through a combination of touching and enticing me, she got me to fess up. I told her that I really liked the idea of other men looking at her. I wanted her to wear sexier clothes out in public for me.
She was a bit taken aback at first, and didn't really understand why I would want her to do that. She was pretty nervous, but seemed to pull together her courage and agreed.
That month was great fun. In addition to pleasing me around the house, she would wear sexy outfits every time we left the house. At first, it was mostly her wearing sexy dresses out to bars and restaurants, which I was loving. Sometimes she wore thigh-high stockings, which I particularly enjoyed. During the second week, I persuaded her to skip the bra and panties one night at a bar while she was wearing a tight, short, red dress that reached about four inches below her ass and clung tightly enough to make it pretty clear that she wasn't wearing a bra. Another day during that week, she went out grocery shopping wearing only a little, tight, white matching shorts and tank top set. Both pieces were pretty small and very tight. You could see a hint of her nipples through the top. She was very uncomfortable when we were out, but I fucked her as soon as we got home again and she was already impressively wet.
Things escalated during the third week, with her wearing shorter and lower cut dresses when we went out. A couple of times, I even noticed her leaning over forward a bit farther than was really necessary or reaching up a bit higher above her head than she had to when she took something off a shelf. She didn't give anybody a real look at her privates, but got very close.
Then, on the fourth week, we went on a vacation to Jamaica. She apparently felt a bit more comfortable in the new surroundings. That week, she wore a very short, very loose, slightly see-through sun dress a lot. You couldn't see her pussy or nipples through it, but in the sun you could see the silhouette of her body very clearly. One day we went to the beach and she took her top off while we sunbathed. On the last night of the vacation, we fucked in our room right in front of the big window. I don't know whether they looked up, but a number of people drinking around the pool could have seen us there.
At that point, she was still really nervous about exposing herself like that, and acted pretty uncomfortable most of the time, but sometimes she was definitely a bit turned on too.
However, the night after we got back, we had another talk. As much fun as I had been having, I admitted that it wasn't working. I was still angry. She cried and begged me to reconsider.