The biggest disadvantage of "oops" moments is that they can only happen once, and then the fun is over.
My advice: Start sharing photos with your neighbor regularly. While discussing last weekend, show a few photos from it, and continue doing so over time. Keep it casual—nothing nude, just everyday clothed photos. Gradually make the photos more interesting: your wife in a new dress you bought her, bikini shots from a vacation, then slightly more revealing bikini photos, or her sunbathing topless while lying on her front, perhaps showing a hint of sideboob later. Over time, as he becomes accustomed to seeing some skin, you can include a photo of her sunbathing topless on her back in the next set. Act nonchalant—don’t comment on it, treat it like any other photo, and move on to the others. If he remarks on it, respond casually: “Yeah, we don’t like tan lines; she often sunbathes topless.” By doing this consistently, you can eventually share more revealing photos on a regular basis and keep the fun going.
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