My Professional Boudoir Photoshoot – Deciding to do it and finding a photographer

Hi again

This is Robin, a occasional contributor here. I want to write about a recent experience I had doing a “Boudoir” Photoshoot with a professional photographer. It is going to take a while to cover the whole experience and so this is just part one.

Like many TGs I enjoy pictures of myself “en femme” and have taken many over the years. Unfortunately I have found that they are generally terrible. The lighting is off, the skin tone wrong, the angle is unflattering, the makeup either washed out or excessive, the posing awkward, the camera out of focus, some body part is cut off, the camera used  not very good. You get the idea, dozens and dozens of terrible pictures. This experience is not uncommon, you can see thousands of them all over TG sites on the web. For a long time I had no local place to take the photos and could do so only on business trips. I would pack a suitcase full of clothes, drag it through multiple airports, unpack it all in some hotel room, try to fit in a shooting time among business meetings, come up with some lame explanation to a coworker why I had such a large suitcase for a 2 day trip, etc.. I would go through all this work and get lots of terrible pictures. I tried different camera, bought photo lights, switched from film to digital but little changed. They were just awful.

Furthermore when I started doing it I used film and so had both the cost of film and developing to deal with as well as the stress associated with having strangers (the film developers) see me en femme. I had nightmares that some friend had a night job at a film developer and recognized me. Costco once mixed my pictures with those of another customer. Trying to locate them made for an interesting experience….

I pretty much gave up on photography in the last few years.

Recently I decided to try it again with my new zillion pixel digital camera. I lugged a huge suitcase from San Francisco to Boston, took lots of pictures, and had them mostly turn out terrible. I deleted the whole bunch. I decided I had to come up with something else or just give up on photography in general.

I do a lot of Groupon scanning, occasionally actually buying something. One of the regular “specials” are photo shoots from various local photographers. The typical proposal is a hour of shooting, a couple of actual prints, and an opportunity to buy additional prints at some discount. One might pay from $50 to $150 for this service. Different photographers have different specialties: family, individual, outdoors, fashion, and “boudoir”. I looked at the various offers and tried to decide which one to do.  The outdoor ones seemed safest but kind of boring. Studio shots seemed more interesting, boudoir shots seemed the most unlikely of all (I am not exactly a 25 year old model or transition TS with lots of surgical “enhancements”).

I did not do much on this front for a few months, as I tried to decide what to do. I thought that going through all the stress of a real photoshoot and then ending up with a handful of pictures hardly seemed worth the effort. Then in February of this year I noticed a new Groupon from a San Francisco based photographer who specialized in boudoir photography, Denise Linley at  She offered a hair stylist, makeup artist, an hour of shooting, and a picture book of 40 pictures for $250. It was an amazing deal compared to what else was available and was too good to pass up.  I figured since she was based out of SF, she had probably experienced everything including all sorts of TGs and well as other assorted San Francisco types. Nothing would surprise her.  I decided to send her an email to see what she thought about the idea. I figured at worst I would get a polite refusal. Even if she said okay, I could still back out. The notion of laying around in lingerie while some total stranger took pictures of me was scary beyond words. At the same I had been playing things “safe” for so long that I felt it was time to do something slightly outlandish. My previous “crazy” action was flying en femme (documented in this blog) which turned out completely okay. Afterall what is worst thing that could happen (other than she is some former coworker who now has a new career).

One night in a rash moment  I sent an email to Denise asking whether she would be okay doing a boudoir session with “CD/TG” types and waited for a response. I received nothing for two days. I figured this might be her way of saying “no” (i.e. “lets just delete the email from the weird TG”) but decided to resend the request just because email problems do occur. She responded quickly time indicating she never go the earlier email. She indicated that she was interested in a shoot  but did not know what “CD/TG types” referred to.

That was unexpected…It goes to show that despite the best efforts of Ru Paul and the Discovery channel, lots of folks don’t know about us. I sent back a short note describing the range of TGs (the two paragraph “your guide to TGs”) to which she responded with “that’s cool, if you want to look like a girl you have come to the right photographer”.

That was also a little unexpected (but very nice). It was now decision time. I had a photographer willing to do a boudoir photoshoot of me, was I really willing to do it? The possibility was now real and really scary. I would have a real hairstylist and makeup artist (not some TG “transformation” specialist) do their best on me so that I could strip down to my underwear, lay around on a bed,  and have a photographer whom I had never met take photos of me. They all assured me they would be fine with it, but I was not sure I was fine with it. I had this odd feeling in my stomach….

After a restless night, I decided to go with it. Afterall, what is the worst that could happen?? I sent Denise the payment and started thinking about what exactly I would wear.. I was committed (or perhaps I should have been committed).

Next time: deciding what to wear and sticking to my decision.


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