Lock in 2024 pricing!

My pricing will be going up starting January 1. But if you get your deposit in by December 31, you can have your session anytime in 2025 and enjoy pricing as it is now.

Oaktown Boudoir is now Dragonfly Boudoir! Same photographer, same place, just a new name. (Why?)

Even if you’ve heard a boudoir session can be transformative, I think you’re still going to be surprised.

People often speak of a boudoir session with the right photographer as empowering and liberating. You can see dozens of my reviews where my clients say just that. Even so, when you take the plunge and dive into the Dragonfly Boudoir experience, I think you'll find the depth of transformation is beyond your expectations.

sweet and flirty boudoir image of woman with long brown hair sitting on a window bench, wearing an open white shirt, her breasts hidden by the sunflower she's holding

nude woman laying on her side, turned away from the camera, with dramatic shadow lines contouring around her body

Here’s a hot take: it’s not about the photos

It's surprising, I know: you're here precisely because you want to have beautiful images. But when you become my client, together we create a space where you can truly be yourself. Where you give yourself permission to express who you are inside. Where you feel more free, more open, and more deeply seen than you might be used to. The absolutely stunning images we create in that space are simply reminders of how amazing you are in your fullest self.

I invite you (yes, you) to join me

My clients span a glorious spectrum of age, race, ethnicity, body type, gender identity, sexuality, and ability. Everyone has their own reason for doing a boudoir session. It can mark a turning point in your life that is either joyful or painful; it can be a reclaiming of a part of yourself you may feel you’ve lost; it can be a celebration, a declaration, an affirmation of who you are. Whatever it is, whoever you are, I welcome and invite you to come with me on this incredible adventure.

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powerful boudoir image of a woman in a white suit jacket suggestively open with nothing underneath. She's leaning over with her short brown hair falling to one side as she looks intently at the camera

sweet boudoir image of a shirtless tattooed man reclining on his side, gently smiling at the camera

boudoir image of a woman in her 60s in a red robe that is suggestively open. She's laying on her side, smiling at the viewer as her blonde hair cascades down to the side

Carmen: in her own words

My awesome client Carmen talks about what led her to do a boudoir session for her 40th birthday, why she asked me to help her create her gorgeous images, and how much her boudoir experience with me changed how she sees and feels about herself.

Here are a few of Carmen's images, which she also graciously allowed me to share (I only use client images with express permission):

Sweet boudoir image of a woman on a window bench, smiling at the camera as she holds a bunch of colorful balloons

Delicate boudoir image of a woman in a knit sweater off her shoulder. She's looking off to the side as her hand is playing with her hair.

Moody boudoir image of woman in red lingerie, sitting up with her legs crossed, looking off to the side

So grateful to Carmen for sharing her words with everyone! I'm looking forward to helping you too. (You may note she refers to Oaktown Boudoir in her opening; that's what I used to call the boudoir side of my photography.)

Feeling unsure about being in front of the camera? You’re in great company

Almost every client of mine had never done any kind of professional photo session before coming to me. Most clients have told me they feel awkward in photos or feel unphotogenic. I can't think of a single client who didn't need at least some help posing.

If you feel any of those things, know that the ten clients you've already seen on this page felt exactly the same way before they contacted me. Once they did, very quickly they found out how much I could not only put them at ease, but also help them develop their ideas and bring those ideas to life, taking care of them every step of the way.

Bottom line: You already have what it takes. All you need for a successful boudoir experience is excitement for this adventure. If you have that, even if you're also nervous (which is totally natural and also a great thing — ask me why), we're going to have so much fun and create the most incredible images together. You don't need to know anything about posing — I'll guide you with gentle, clear direction. You don't even need to have a clear vision of what you want when you come to me — we'll figure it out together. Not long from now, it could be you on this page inspiring someone else to break down their own barriers.

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More reviews from my clients

"I wasn’t expecting to have so much fun! Posing, laughing, and getting in touch with my come-hither side was exactly what I needed. Cheshire is so easy to be with. He makes the whole experience feel quite natural and fun. Words failed me for quite a while when I saw the pictures. I didn’t realize how much I needed this transformative experience. I have so many levels of gratitude and joy in this experience."
Serene
"Like many, this was quite a bit out of my comfort zone, but Cheshire makes it fun and easy. If you're a woman, you may be hesitant about a boudoir shoot with a man behind the camera, but he could not have been more respectful; I felt at ease the entire time. He was able to help me bring out a more confident and sexy side, and the photos look like the very best version of myself."
Katie
"Cheshire was incredibly gracious and meticulous and made me feel incredibly comfortable throughout. He takes care to understand your comfort level as well as preferences, and easily pivots to tailor the experience to you. Best of all, he treated me as a collaborator and encouraged that I bring my own vision and ideas, which added a fun artistic dimension to it. The experience was absolutely wonderful!"
Rita
"As a blind person I wasn't really sure about what my options were. Cheshire took all the time to really explain things and figure out how to make things as accessible to me as possible. He sent me some sneak peeks of images after the shoot with very detailed image descriptions as well which I certainly wasn't expecting but it made a huge difference to me and really shows his dedication to his individual clients. Thank you to everyone else who gave so many good reviews because it made choosing Cheshire an easy choice."
Tiffany
"I cannot overstate how amazing the whole experience was. Cheshire was enthusiastic about my ideas, and really worked with me to make aspects of the shoot very customized to me and my partner. Bring your weirdest ideas, and he'll make them absolutely beautiful. If you've ever thought about doing a boudoir shoot, you should ABSOLUTELY take the plunge and do it! You'll be in the best hands with Cheshire."
Emily
"Cheshire was very kind to me all the way through. He gave me a tour of his studio, listened to my story, and assured me he will take care of the rest. What I like and admire about him the most is he made me feel safe and secure throughout everything. Overall, my experience for my very first boudoir photoshoot with Cheshire was amazing and life-changing!"
Melissa
"I cannot say enough about how incredible my experience was with Cheshire! I was excited but hesitant to do a boudoir shoot, but Cheshire made me feel comfortable from our first interaction. He was so professional and thoughtful when we were in the planning stages and helped me come up with the kind of shots I was envisioning and the vibe I was trying to achieve. The whole experience was seriously amazing!"
Kendall
"What an amazing experience. I have several friends that have booked with him so I knew I was in good hands. I’m not a shy person but his cool gentle demeanor really had me relaxed and confident in our session. I was amazed how great the pics came out in just a short time. My fiancé was pleasantly surprised with his Xmas gift and I owe it all to this amazing experience."
Jennifer
"This was such a fun experience. Cheshire made me feel so comfortable and we had lots of laughs. His work is absolutely beautiful and he made me see my own beauty. I gave the photo book to my husband as a wedding gift and he LOVES it. Everyone should have the experience of a boudoir photoshoot. Thank you so so so much!!!"
Marissa
"We loved working with Cheshire, from first contact to the photo shoot itself! He's so thoughtful, both in the physical details of the space he so lovingly provides, and, just as importantly, how he deals with us as people. He made us feel more than comfortable and the photos, ultimately, were superb! Can't wait to head back into his studio and work with him again."
Girish
"I had the best day creating photos for my fiancé as a surprise wedding gift. I was apprehensive at first but Cheshire made the whole experience feel so natural and fun. I was amazed by what I was capable of and how the photos turned out. He is an all star and you won’t regret choosing him!"
Kylie
"Cheshire absolutely made my vision come true, made me feel comfortable, and went above and beyond spending time to make sure I was happy with the pictures he had taken. The direction he provides is super helpful, you can tell he has been doing this for a while! I am so happy I made the decision to do this photoshoot with Cheshire (my husband is ecstatic about it too!)"
Bre

A journey tailored just for you

Take a look through my site and discover how I craft your one-of-a-kind experience: detailed one-on-one planning before your session, where I listen to your needs and collaborate with you on ideas; the incredibly fun session itself, complete with hair and makeup to your taste, music and snacks customized to your tastes, and of course a few hours of capturing one breathtaking image after another; a viewing session where I help you figure out what items will work best for you; and my meticulous work creating those gorgeous keepsakes. Ready? Dive in.

Flirty boudoir photo of a woman sitting up against a sofa, backlit by late afternoon light. She's wearing a strappy black teddy, and one hand is up to her hair as she looks over, smiling sweetly at the camera

No time to explore right now?

Here's everything you need to know in a nutshell. I'm Cheshire Isaacs, a top-rated Bay Area boudoir photographer who specializes in natural boudoir photos. I'm grateful to be included in lists such as 12 Best Boudoir Photographers in San Francisco (Peerspace), Top 10 Boudoir Photographers in San Francisco (BoudoirRule.com), and more. I've been doing boudoir photo shooting since 2015 and have taken care of hundreds of clients since then. Please get in touch with one of the buttons below and let's chat about how to get you your absolutely gorgeous new boudoir pictures.