The details

I hope you've had a chance to see my welcome pages and find out how I approach boudoir. (If you haven't, start here.) Here are some final details such as pricing, info about me, and frequently asked questions.

Investment

My session fee is $495. It's kind of inaccurate to call it a session fee, because it covers so much more than your actual session. This fee covers your entire one-on-one experience with me, from planning your session to the session itself (including hair and makeup!) to a later session where you'll see the best of what we shot and have a chance to order your finished items, plus so much more. I tailor your experience to your wishes and preferences, ready to help you with whatever questions you have or fulfill any special requests.

Because each client is unique in what they will want as their keepsakes, I have separated my session fee from my finished items such as books, prints, digitals, and more. You can expect your total investment to be between $795 and $4000+; most of my clients' total spend is approximately $2500.

Your Session includes

detailed 1-on-1 session planning

20% off lingerie from Pink Bunny

3 hour session with up to six outfits/settings

Full makeup and hair included*

Gourmet snacks tailored for you

Custom playlist of your favorite music

Access to studio wardrobe and accessories included

Ordering session at a later date

*If you prefer to handle makeup and hair yourself, you will receive a $200 credit toward finished items.

a portrait of the artist as a (youthful!) middle-aged man

Who am I, and how did I start doing boudoir? (spoiler alert: it was an accident!)

Hi, I'm Cheshire, and yes, I became a boudoir photographer kind of by accident. In 2015 I'd already been doing headshots and other types of individualized portraiture for a while. One day I was registering for a site to connect me with potential clients, and it asked what kinds of photography I wanted to do. Boudoir was one of the options, and I clicked it even though I didn't know much about it. (I had shot some maternity boudoir with my wife five years before that, not realizing there was even a term for what we were shooting!)

Not long after that, though, I met a potential client whose story I'll never forget. She was in her early 30s and was facing a double mastectomy. For various medical reasons, she wasn't a candidate for reconstructive surgery, but she wanted to do a session post-surgery that showed her scars. She wanted to create images that she could share with her daughters to show them that there isn't just one way of defining beauty.

From that moment, I understood the power of this area of photography. It quickly became the most emotionally rewarding work I do. Over the years, I have helped hundreds of people celebrate and honor themselves and their joys and hardships. Boudoir is such an empowering, liberating experience, and it is such an honor for me to be part of each person's journey.

A few more bits of info about me: before becoming a pro photographer I was an art director (my design skills enable me to make killer unique books for my clients). I love to cook (you may reap the benefit of that too), read, hike, travel, play games, crush it at karaoke, and more. Though my studio is in Oakland, I live in Emeryville with my wife, our teen, and our cat, Ari (Not Sorry).

Why “Dragonfly”?

For many years my boudoir photography was Oaktown Boudoir. I always wanted to call it Dragonfly Boudoir but this domain wasn't available.

Dragonflies are symbols of transformation, love, and health — such core elements of what boudoir is all about. On a personal note, every time my wife and I looked at a wedding venue, we saw dragonflies, and it became our symbol. Two dragonflies are on each of our wedding rings, which I designed. And as of this writing (October 2024), we're celebrating 20 years of marriage.

The decision to rebrand to what I wanted all along is a perfect example of both dragonflies and boudoir itself: I'm reclaiming that which is most significant as I move forward. Thank you for traveling with me.

Other questions you might have

I get it! There are any number of reasons you might prefer someone female-identified behind the lens. Many of my clients have told me that initially they assumed they'd want to shoot with a woman, but after contacting me and finding out how invested I am in really getting to know my clients and bring their ideas to life, they saw not only how safe they would be with me but also how well I could capture their vision. It also helps to see that dozens of women and men have taken the time to write detailed reviews that say how comfortable they were with me photographing them in this way, how professional and respectful I am, and how blown away they were by the results.

Absolutely! I've shot with over 200 people who also never knew how to pose before walking into my studio. From our session planning, I'll have a good idea about what kinds of moods you want to capture, and I'll help you find the poses and expressions that bring out exactly what you want to capture — remember, this experience is all about representing you. I give clear, gentle hands-free instruction that will have you posing like a pro in no time.

Yes, generally you will bring your own things to wear. Fit is so individual, and you want to make sure you love how a piece fits you, so it's best if you bring pieces you know you love. And yes, lingerie is often what people bring, but you don't have to! It's whatever makes you feel good. I also often recommend bringing outerwear like a favorite dress, sweater, pair of jeans, partner's shirt, pajamas, etc., as it can be really fun storytelling to incorporate into your session. I also encourage you to think about bringing something that is absolutely unique to you — one time a client brought a power tool, and creating images with that was amazing. I do have a few robes and other things at the studio you can use, including fun accessories from sweet to spicy. Finally, a session is a great excuse to get something new for yourself. My clients get a sweet discount at Pink Bunny, my favorite lingerie boutique. Their pieces are absolutely gorgeous.

While makeup and hair with my professional makeup artist is included in your session fee, it's fully optional — but it can be helpful. A lot of people feel they can do their own makeup well enough, or they simply want to look “natural” and fear that makeup is going to make them look, well, too "made-up." That's absolutely ok. There's no such word as "should" in my studio; I want you to feel like yourself. However, having my makeup artist help you can be a huge benefit; my makeup artists are highly skilled at natural looks and will collaborate with you to find the look that is just right for you. Plus sitting in the makeup chair and getting pampered for 90 minutes while you enjoy delicious snacks and beverages and we chat and laugh is a wonderful transition from the outside world into the world of your boudoir session. It's spa day and fun and bold photo shoot day all wrapped up in one.

I hold on to your files securely and indefinitely unless a client specifically asks me to delete their files.

I always love to feature my amazing clients on my website or social media, but I know that some clients prefer to keep their images completely private, and I honor that. If you do let me feature your photos, I will make sure I have your permission to use the specific photo(s) I have in mind and can anonymize the photo however you wish (e.g., cropping out eyes or tattoos.

I do get this question a fair amount! I am extremely fortunate to have been married since 2004 to someone who is not a jealous person by nature. As much as I am, Sarah is incredibly moved by the transformations my clients experience. Some of the reviews my clients have written have brought her tears of joy (same for me). And yes, she's had her own sessions with me as well, so she knows exactly what the experience is like. Though she hasn't written a review yet....

If you have other questions that aren't answered here, please don't hesitate to ask!