Having a panty shopping buddy sounds awesome! Shopping the stores in person is a wonderful treat, but it took me a long time to build up enough confidence. It's so worth it though.
I always thought shopping for panties was an impossibility. I thought that I couldn't get away with it, like it was robbing a bank. Eventually, I just got fed up with not being fulfilled and decided to go shopping at a department store during the daytime.
At first, my mentality was to get in and get out in a hurry, like pulling off a bandaid. I was really nervous and even gave the cashier a cover story about shopping for my girlfriend's birthday. Although triumphant, it was an awkward and very stressful event.
After that encounter, I thought that I'd never go through with it again. A few years passed, but I had had a taste of bliss and knew that something was missing from my life.
I needed to rebuild my courage, so I started small and kept trying to push myself outside my comfort zone. I thought to myself, whatever worst case scenario or awkwardness could possibly happen inside of that store was ultimately meaningless, because following checkout, outside I would go into the world with a bag full of my joy.
First, I went to a 24 hour drugstore at like 3 AM and amazingly they actually had some microfiber briefs. I was proud of myself and it felt empowering. I began to wonder what else I was capable of if I pushed myself to simply do it. Around Christmas, a department store nearby was open 24 hours. Jackpot! I went at 3 AM again and I had the entire lingerie department to myself! I took my sweet time and savored every moment. It was like being a kid locked in a toy store overnight. Can you imagine the euphoria I felt? While checkout was somewhat awkward, I was becoming more and more comfortable and at ease.
In a very short span of time, I went shopping for panties at CVS, Kohl's, Macy's, Sears, Victoria's Secret, Soma Intimates, Target, Walmart, and even a local lingerie boutique. It can really be addicting and the saying is that you can never have enough panties. There are just so many different fabrics, colors, styles, and designs.
Shop during off-peak hours if it makes you feel more comfortable or travel somewhere not in your neighborhood. Figure out what's holding you back from getting what you want and see if you can come up with a clever plan for working around it. It will get easier after awhile, once you get outside your comfort zone.
The hardest part about shopping for panties is setting foot over the threshold into the store/lingerie department. When I was less comfortable, it would take me a few rotations around the store/mall before I could build up the courage. It felt like orbiting in space, trying to orient your trajectory in order to dock with a satellite.
When I shop, I typically don't like to interact with the sales staff very much. I kinda like to be left alone. I'm typically nervous enough as it is and having to answer questions or possibly even lie is even more stressful. But, I wonder whether someday I'll be more candid and social.
It depends upon your budget, but I would recommend getting a variety of fabrics, styles, colors, designs, etc. and figuring out your personal tastes and preferences. Shopping during a big sale will also get you more bang for your buck. Also, see if they have a clearance section!
I would recommend planning beforehand which store(s) you're going to visit and check out the selection on their websites ahead of time. I think everyone has a different opinion as far as the best store, I think that you'll get to decide that for yourself. However, the location may not necessarily have all inventory and sizes available in-store.
I've read a ton of personal stories of shopping trips for panties and any negative experiences with sales staff are very rare. The sales associates there were hired for a reason, to be friendly and helpful without exception.
As far as sizing, I would recommend getting a tape measure beforehand and measuring your hips; that's really the only important measurement involved. Also, you can check out your size you are on the store's website. It may take some trial and error as far as what fits you. Check out this guide: http://www.herroom.com/Lingerie-For-Men.aspx#pantywear
Remember to have fun! If you relax and go in with a sense of purpose, you will blend in fine. Feel free to PM me if you have any questions or would like to to tell me a little about your preferences and I can offer you some better recommendations!