I wouldn't have any problems trusting a guy with buying lingerie. Only issue I would see is the same issues I face anytime I buy clothes, sizing. The shape of my body makes it hard and completely differently with every store, company, cut of clothing, etc. But with that issues I would just suggest to them to look for something that has one size fits most/all or plus size and go with plus size. I've only had one thing that was plus size that didn't fit (would hate to see how small "one size fits most" would have been!).