Reddit mentions of Pleaser Women's Prestige-16 WS Peep-Toe Pump,White Suede,12 M US

Some ideas for you. None of this is considering what your budget or their budget will or won't handle.

1. It is a MUST for your roommate and her friend to go to the spa and get mani/pedi and their hair/makeup done. For hair, a blowout with curls is MUCH better than an updo for example. For nails, suggest they opt for a dark red or black color for this, because you want CONTRAST in your pics. For makeup, tell them to not be afraid to go bolder or more dramatic than they normally would for "daytime" or "work" wear. Extra mascara or false lashes are A-OK for this kind of shoot... This is a boudoir photo shoot, not snapshots in the garden, after all.
   
   
2. Suggest they have a glass of wine before you start. Not get drunk, but a glass to relax and loosen up a little.
   
   
3. Outfits: Allow the girls to get a couple outfit changes. Yandy.com has some great stuff that is not overly expensive. There are probably other stores too, but that's one I know of for boudoir shoot clothes.
   
   3a) Shoes: This is the time for new shoes. Imagine spending all the time, money, and everything getting hair, makeup, nails, new outfits, but then you take a picture where a high heel is in the frame, and you see that it's scuffed or well worn on the sole. It will distract. If the girls are more daring, they can get some really sexy (dare I say "stripper" style) shoes on Amazon... something like these or a more conservative dressy/sparkly sandal heel like this or even more conservative, like this, in black. TL;DR: Make sure they get new shoes for the shoot.
   
   
4. Speaking of outfits, suggest that the girls not wear a bra earlier in the day to avoid leaving strap marks when they change into their outfits. They can take this advice or leave it, but I always recommend to avoid anything with straps at least a few hours before the shoot. It's odd being a guy suggesting this to a female without sounding like a perv, but just be professional about it.
   
   
5. Friend or not, have an assistant (definitely not another male) that can assist with lighting, being a spotter (e.g. balancing the other end of the ladder if you go up high on to shoot down at her), and as a witness for you in case of any accusations of inappropriate behavior later. I was shooting a bride before the wedding, and realized I was in a room alone with her, and afterwards I realized I was pretty vulnerable if she would have made any kind of accusations. Your situation may be completely different, but you did say she's a new roommate, so I don't know how well you know this girl. So just a word of caution there.
   
   
6. There are some creative things you can do - such as using a piece of cut out pantyhose as a lens filter, which can make some really cool dreamy looks. example here - scroll down to #5 or this article here which has a few other special effect ideas that would work well for boudoir. Also, follow the other advice: Long lens = more flattering, short lens = less flattering. If you can shoot 50mm or longer, that would be much preferred to shooting with the short end of a 18-55 kit lens.
   
   
7. Invest some time Googling Boudoir Photography websites -- the other photographers that do this as a business do a pretty good job showcasing their work. Study, and learn their posing, camera angles, lighting, room setup, and so on. Most of these folks have a Pinterest board -- study them. Print them out, or whatever, and make a plan that you can stick to.
   
   
8. The other suggestion by /u/theflyingmoose -- get a hotel room or other suitable private setting, if you want to PM me your location, I can scout some out and be specific. Being generic, look for anything downtown, historic, and something like that. I'll follow the rule I give for scouting shoot locations in general: find something very old or very new. Each will have pros and cons, but it's a decent rule of thumb.
   
   
9. I just realized it's not clear from your post text... are you shooting the girls together? Or is this two separate shoots? If they're together, still shoot each of them separately, and then do a few together. Don't do the whole shoot of them together, without getting them solo. If it's not supposed to be a together shot, don't even suggest they take any pictures together unless they bring it up.
   
   
10. Also, as /u/theflyingmoose says, treat it like any other professional/paid job -- Especially as it comes to delivering the final product to them. I would highly suggest against just giving them the JPGs. What are they gonna do? Take them to Walmart and print a bunch of 4x6s? Likely not. You should come up with a package that you can pre-assemble on paper (e.g. we will take your best N pictures, and from them we will print 3 8x10s, 4 5x7s, and a mounted enlargement at 12x18, which your cost in will be whatever it is, but for what I've listed here is not around $30 in cost at someplace like Mpix/MpixPro (most of that is the enlargement)... you get the idea. Don't do all this work with hair and makeup and outfits and the hotel room, and have the final output be just digital files on a USB stick. The incremental cost to make the final output really special is quite small considering the preparation that went into this.
    
    Lastly, feel free to PM me any specific questions on this if you like.