Dragonfly Boudoir Flies to Vegas

A liberating, life-changing experience—June 8, 9 & 10 — Only 2 spots left!

If you have ever thought about doing a boudoir session, but held off because you weren't sure you could find a photographer who could really help YOU, your moment will arrive very soon. I'm bringing my unique boudoir photography experience to Vegas June 8-10, and I would love to help you create the images you've been dreaming about.

Even if you've heard that boudoir can be a transformative experience, I think you're still going to be surprised how much it affects you. I hear that all the time from my clients at their session. "I know other people say that," they tell me, "but I didn't think it was going to happen like that for me."

It's going to happen like that for you too.

boudoir image of a woman in bed with pearls

boudoir image of woman on her knees on a hotel bed

boudoir photo of woman in bathtub with bubble bath and rose petals

What makes my boudoir experience different?

In a word: YOU.

What makes my sessions unique is what makes you unique. I take a lot of care to find out what's inspiring you and what you enjoy, so that I can tailor your session to your individual tastes and preferences.

Imagine walking into your session with your favorite music already playing, a custom playlist curated just for you. Imagine refreshments that were selected specifically to your palate. Imagine an unhurried session tailored to your style, with expert posing guidance that brings out exactly how you want to see yourself.

Did I mention it's also incredibly fun?

Boudoir with me is so much more fun than you're expecting. It's one of the rare moments in time when you can be completely yourself and bring out who you are inside. Even if you've never had any kind of professional photos before, you're going to be surprised how easily and quickly you're posing like a pro.

Scroll back up and look at the three women above again. They're not models; they're clients, and none of them had ever done anything remotely like this before they came to me.

It's going to happen like that for you too.

Reminder: June 8, 9 & 10 — Only 2 spots left!

Balcony of the suite I've secured for the trip, with views of the Strip

Solo or partner/BFF session? It's up to you

Whether you want to shoot solo or bring a partner or BFF with you is totally up to you. Couples sessions are amazing, as are sessions where you have an energetic friend cheering you on. It's all about what will help you bring out what you want to express.

the details

I've booked the suite on the Strip pictured on this page (images of the suite are the hotel's, not mine), which will provide a number of opportunities to create breathtaking images.

The session will be approximately two hours in length, which should allow us to do 3 or 4 different settings. You'll bring your own wardrobe and arrive makeup-ready.

Your experience includes all of the one-on-one detailed planning and customization that my clients enjoy, down to specially selected refreshments and a playlist curated to your favorites. And you get my exclusive 20% discount to Pink Bunny, my favorite indie lingerie boutique.

This special offer includes your entire processed gallery (at least 60 images) in full resolution, plus three of your favorite images finished to your preferences. A hotel session plus keepsakes like these would normally be more than $1800 — with this special price of $895, you save at least 50% what something like this would normally cost.

But I only have time for a few sessions while I'm there, and June 8 is already taken. Grab your spot before I'm booked up! Use the form below or for quicker response, call or text me at 510-551-9018.

view of the bathroom of the suite I've secured for the shoot

Vegas Destination Session:
$895 total

2 hour session with up to 3 looks

Solo clients and couples/BFFs welcome

Pre-session one-on-one planning

Your entire gallery in high-res

Three finished digital images

Gourmet snacks provided

Custom playlist of your favorite music

20% off lingerie from Pink Bunny

Other keepsakes available

reserve your spot now!

Who am I?

I'm Cheshire Isaacs, and I've been shooting boudoir for 10 years, and other specialties like headshots over 15 years. Normally I shoot out of my studio in the SF Bay Area, where I've created gorgeous images for hundreds of boudoir clients since 2015. I'm rated five stars on Yelp with over 60 reviews, and I'm featured in several "best boudoir photographer" lists in the San Francisco Bay Area.

I specialize in what I call natural boudoir, where my goal is to bring out who you really are. My images range from light and airy to dark and moody, lighthearted to intense — whatever is true to you.

The thing that drives me the most is creating a space where my clients can finally feel free to express who they are. I enthusiastically welcome solo clients, couples, and groups of every gender, sexuality, race, age (well, 18+), body type, and disability.

Sessions with me are relaxed and more fun and liberating than most people expect. I provide expert posing guidance with gentle, clear direction. Some of my clients have called their sessions life-changing. I'm looking forward to hearing what you want to create for yourself!

Got questions?

Why Vegas? I love going there, and I don't do it enough. I enjoy playing poker, eating great food, and I enjoy the vibe — for a few days a year, anyway!

Why a hotel? I love shooting in my studio, which is what I do with about 95% of my clients. But sometimes there's just no substitute for the look and feel of a luxury hotel suite, and we're going to make the most of it.

What do I bring? How sexy does this have to be? Here's the thing: even though you're seeing this on my boudoir site, your photos don't have to be boudoir style at all! I work closely with each client to find out how you want to see yourself and what you want to express, and we go from there. What you bring to wear, how revealing you are in your session — it's 100% up to you. There's no "should" of any kind in my sessions. What we capture for you could be fully-clothed elegant portraits, they could be sweetly romantic, they could be incredibly spicy, anything in between or all of the above — it's your session, and I will help you make the most of it and decide what wardrobe will work best for what you want.

Will I be safe with a male photographer? Yes — my reputation depends on it. My clients constantly say how professional and respectful I am, which you can see in my reviews. I don't touch clients without express permission, and I am extremely careful to find out what your comfort zone is ahead of time so that I can help you stay within it.

Can I bring a friend for support? Absolutely! The only requirement I have is that they be an unabashed cheerleader for you.

What about makeup and hair? You will take care of that on your own prior to arrival.

How soon will I get my images? We'll set up a time to meet within a week or two of your session to review your gallery, when you can pick what you'd like me to finish for you and/or order additional items. Meetings can be in person or over Zoom, depending on your location.

Are you going to post my images publicly? I only feature clients with their express permission. If you want to keep your images completely private, that's absolutely your right.

How will payment work? To confirm your session, I'll require a $495 deposit; the balance of $400 will be due at the session. Because of the hard costs of a destination session like this, there will be no refunds except in the extreme case that I have to cancel the session, in which case I will refund your deposit in full. If for some reason you have to cancel, I will honor your deposit if you want to have a session at a later date in the Bay Area.

carmen's video review

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.

More client reviews

"From the first email to the final shots, Cheshire was kind, supportive, and helpful. He did a great job helping me prepare for the shoot so by the time I walked in, I felt completely ready and excited. Cheshire clearly loves what he does; the whole experience felt natural and fun. Now I have gorgeous shots that I feel really capture me. I cannot recommend Oaktown Boudoir enough!"
Kate
"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