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?)

image of Vegas hotel room with the words "Dragonfly Boudoir flies to Vegas" superimposed

I'll be in Vegas June 8–10 with an incredible place to shoot. Only 1 spot left — Tue 6/10! Hit the button for details.

details & booking

Fall 2025 Open House graphic, with three boudoir images in a burnt-orange duotone

Join us for our Fall 2025 Open House! Bites, drinks, portraits, and more. Sat 10/25 1-4pm

details & free tickets

The Bay Area boudoir photographer for people who want to reclaim something about themselves

We live in such a restrictive — almost puritanical — society, don't we? Not to mention a world with an incredibly narrow view of what beauty is. On top of that, just living overscheduled lives in the roles of work, family, and more. Add on the negative messaging from external and internal voices telling us how we should or shouldn't be, especially around topics like sensuality — all of that keeps us from being able to be our fullest selves. If you're ready to reconnect with and reclaim parts of yourself that you've had to hide for whatever reason, this is your moment.

My incredibly versatile, creative studio is located in Oakland, CA near Lake Merritt, but I also shoot in hotels and client homes, whatever the best option is. I even make it out to Vegas when I can.

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

You can absolutely do this. Yes, you.

If you've never had professional photos before — or if you usually hate photos of yourself — you're in the same boat with 95% of my clients. 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’m the same way myself!)

If you feel any of those things, take a look at the photos on this page. These people are clients just like you who 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 (even if you're also nervous — that's natural!). 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.

A complete experience tailored just for you

Clients are surprised and delighted by how personalized their sessions are. I take a lot of care to find out what's inspiring you and what you enjoy, so that I can customize your session to your individual tastes and preferences. Imagine walking into your session where...

your favorite music is already playing, a custom playlist curated just for you
a plate with food you love is already waiting for you
you feel welcome and celebrated just as you are
we have unhurried hours to be creative in a truly versatile space
you receive expert, gentle, and clear posing guidance to bring out what you want to express

I welcome everyone

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 celebration, a declaration, a catharsis, 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

Client testimonials

"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
"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 was blown away by his thoughtful collaboration throughout the entire process. His ability to truly listen made me feel completely comfortable, even before I stepped in front of the camera. Cheshire's coaching was spot-on--especially when I asked for help with expressions. He showed me how to breathe in a certain way to create a naturally sensual look, always with professionalism and respect."
Amanda
"It was truly a transformative experience. Everything about me is the same as it was before the shoot, but my perception of myself is transformed. It's beyond feeling beautiful. People talk a lot about how empowering boudoir is and I didn't really believe them, but it's so true. I'm so grateful to have these photos. They are a marker now of a new chapter in my relationship with myself."
Khadijah
"We shot a couple pictures with a jigsaw puzzle I had been working on. I ordered a keepsake book which is gorgeous and exactly the way I want to remember the day. But when Cheshire brought the book by, he also brought me a jigsaw puzzle of my favorite photo. It was such a special touch and a real testament to how much he thinks about each client and their specific wants and needs."
Mari
"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."
Mr. G
"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
"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
"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

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.)

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

Oh hey, it's my face

Hi, I'm Cheshire Isaacs. I've been a professional photographer since 2009 (headshots, food, commercial work and more) and started doing boudoir in 2015. Since then I have worked with hundreds of clients just like you. I've been included on lists of the best Bay Area boudoir photographers by places like Yelp, Peerspace, BoudoirRule, and WeddingRule. It's such an honor and privilege to create this liberating experience with each client, and I can't wait to find out what you want to create for yourself. Please get in touch!

FAQs

I get it! There are any number of reasons you might prefer someone who identifies as a woman 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 what an artistic collaborator I can be with their vision. You can see a lot of detailed reviews above!

If you get through all of the info here and decide you still want a woman to do your session, I'm very happy to make referrals if you like.

Absolutely! You're in the same boat with almost everyone who comes to me. I've shot with hundreds of 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.

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!

Let's have a conversation, even if you're not sure whether boudoir is right for you — it's free!

I would love to hear what's inspiring you to seek out a boudoir session. Please contact me for a free 15-minute consultation — I can answer all your questions and give you details about the experience. Don't like forms? Call or text me at 510-551-9018 or click here to email me. Can't wait to hear from you!