My wife and I had married fairly young, especially for her since I am almost 5 years older than she is. She was merely weeks out of her teens when we wed, and for a long time her modesty was at times a challenge. She was too timid to undress in front of me in the light, and sex was always in complete darkness. Over the months and a few years she began to loosen up slightly, to the point where nudity around the house wasn't a problem, but anything outdoors, in public, or with anyone else around remained in that veil of modesty. This was in spite of her having a dynamite body, but we're all different.
With lots of prodding and begging she finally began to allow me to take a picture now and then of her partially dressed, and eventually I was able to get some shots of her awesome breasts. They aren't huge, small C cups at best, but they are firm, stand pert, and are beautiful as well as tasty. So, finally with some photos in hand I took the liberty to circulate a few to a couple of websites in hopes that some positive comments would loosen up my wife a little. Well, the positive comments came and they had just about the opposite reaction from what I'd wanted. Instead of being appreciative and accepting of their comments and a few requests for more, she became embarrassed and closed those modesty doors even tighter. Things went backwards from what I'd wanted, at least for a while.
We took a trip to Jamaica and though I couldn't get her to agree to visit one of the more open resorts, the place we stayed at did have a nude beach area and was populated primarily with Europeans. That week was filled with topless women aplenty and even though I couldn't get Trish to visit the nude area I did catch her looking in that direction several times. I once even got her to go into the nude hot tube one night, but only long enough for her to officially comply with my pleas and then she was back out and the bikini back on. The one thing that was good, though, was that Trish got to witness a lot of breasts of all sorts of shapes, sizes and ages that week and I think it made her more comfortable in how she looked and with the idea of being more open in her dress.
Once back home I approached the topic of some exposure to Trish, and she had come to some mixed feelings. She was curious about how people would view her body, as good or not, but she was still too shy to actually expose herself openly. We had been invited to a party at the house of some friends that live on the lake nearby and I suggested that perhaps her top could "fall down" at some point, but she was still to timid for that, her knowing those people and all. So, the trick was to be around strangers that she wasn't likely to meet again.
I had a group of fellows coming to town in a few weeks for a business meeting and it was up to me to arrange all of their lodging, meals, entertainment, etc. I didn't know these guys personally and it was most likely that I'd never see them again after this event, so I began to think of something where Trish could work as a waitress or something and see how things went from there. A poker night would work perfectly, and I'd simply tell the guys that I had the refreshments and bar arranged. Trish agreed to work as the waitress and barmaid and she agreed that she would wear a shear blouse with no bra and would allow the buttons to hang free, giving the guys a good look at her boobs.
The day arrived and Trish was nervous like I'd never seen her before. I told her to relax, and have a drink or two if she needed to. Plus, I told her it would only go as far and show as much as she wanted, that I would be there as her "employer" to make sure things didn't get out of hand. Since there were only three other guys going to participate, she was okay with this plan. And I must say that when she dressed she looked hot. The blouse was so sheer that you could plainly see her dark areolas and when her nipples stood erect the fabric was only a tease. She had bought a pair of very short shorts and the thong allowed her butt cheeks to peak out the bottom whenever she bent over any at all. It was all I could do to keep from jumping her right then and there!