I was blown away by the experience and the final product. Working with Cheshire was awesome from beginning to end. I actually found him after speaking with a different boudoir photography company whose ad I had seen on Instagram; I decided to do some research before committing to anyone, and found Cheshire on Yelp, checked out his website, and put in an inquiry. He called me very quickly and the conversation was so different from the other places I spoke with! Instead of just laying out "here's how it works, here's what you get for this price," etc., he asked a lot about what I was looking for, what I hoped to get out of it, my motivations or inspirations, etc. That personal touch carried throughout the experience. He consistently made an effort to understand what I was looking for--from the planning process to the photo shoot to going through the photos afterward--to make sure that I got exactly what I was hoping for. The photos themselves are absolutely awesome. It's incredible the different looks and feels he creates in a relatively small studio. More importantly, he just has an incredible eye for what is going to look good and how to create looks, moods, etc. I felt super comfortable the whole time, and I think that shows in the final product. Everyone who has seen my pictures has been blown away. He's way more than just a photographer; he's a true artist. Never in a million years had I ever imagined having a giant naked photo of myself on my wall, and yet here we are...and everyone who's seen it has been amazed. Can't recommend him highly enough! read more

Dragonfly Boudoir - Session Photography Near Me - Oakland, California

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If you're looking for a photographer don't hesitate to schedule with Cheshire he's absolutely amazing he knows how to capture the beauty and elegance in his photos! I'm more than pleased and satisfied with his work he is a pro at his craft and has a keen eye for the perfect pictures! I cannot express how beautiful all my pictures turned out there exactly what I was looking for! read more

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I had a great experience with Cheshire. He made me feel very comfortable the entire way through and the final products were fabulous. His studio was quite versatile, being able to create many different vibes through changes in location and lighting, allowing us to create a lot of very different images. It was a long day, but the whole experience felt very personalized and special. 10/10 would do it all again! read more

Cheshire is an amazingly talented photographer. He is professional and has keen eyes on details. All his photos show authenticity and unique features of the clients. I would definitely choose him for our next events. Highly recommended! read more

Cheshire is extremely professional, friendly, and kind he is truly a master at his craft. His knowledge of photography and also his ability to turn your vision into reality are unmatched I cannot recommend him enough. read more

Cheshire is the ideal boudoir photographer. He's warm, communicative, and great at calming nerves. Both the ideas stage and the photshoot itself felt like a rich artistic collaboration with someone who believed in my creative vision just as much as I did. Can't wait to work with him again. read more

If you've been thinking about a boudoir shoot but don't know where to start, I highly recommend contacting Cheshire at Dragonfly Boudoir! I wanted to do something empowering for myself before undergoing two shoulder surgeries--and surprise my boyfriend with a sexy photo album for his birthday. But I had so many questions: How many outfits do I bring? Will I feel rushed during the shoot? How do I even look sensual on camera? Will the photographer understand my vision? And honestly... how will I feel being photographed by a man? All those anxious thoughts disappeared after speaking with Cheshire. Having worked in luxury customer service for many years, I was blown away by his high-touch communication and thoughtful collaboration throughout the entire process. I initially came in with just the vague idea of a "sexy photo album," but with his guidance--including inspiration photos, a detailed questionnaire, Pinterest boards, and real conversations--I was able to define exactly the mood and style I wanted: sensual, playful, erotic, and more. His ability to truly listen made me feel completely comfortable, even before I stepped in front of the camera. On shoot day, Cheshire curated every detail. He played my personalized playlist (top 5 artists!), provided my favorite snacks, and created a private, cozy space for changing outfits. His hair and makeup artist was incredible. While the studio is intimate, it offers a surprising variety of backdrops, lighting setups, and themes that gave my album stunning range. 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. I never once felt rushed or uncomfortable--even when baring it all. The photo album is definitely an investment, but absolutely worth it. After the shoot, Cheshire presented the best of the best (no awkward bloopers!) so I could confidently select my favorites. The final album--and accompanying thumb drive of images--turned out beautifully. My boyfriend was thrilled, and I was overjoyed. I'll definitely be back for a second shoot in a few years. The confidence and empowerment I gained from this experience were priceless--and blowing my partner's mind? Just the cherry on top. Thank you, Cheshire! read more

While preparing to have a hip replacement, I had to lose a pretty sizable amount of weight. I love my body, and I wanted to capture it before it changed too much. Boudoir photography was the best way I thought to do that while making me feel incredible. So I reached out to a handful of photographers and Cheshire was the first one to get back to me. I didn't anticipate connecting with a male identified photographer but the way that Cheshire talked about the collaborative process, everything that was included, and how he really curates the day to be a special experience spoke to what I was looking for. He also really inspired me to come up with a concept and put together ideas that I felt would represent myself. After talking a little bit, he suggested that we take a look at my house as an option for shooting. I love my house and I've worked very hard to make it a place. I'm comfortable in. The day of the shoot, Diana did a spectacular job on my hair and make up. I wanted to be as natural as possible, but also look flawless. Cheshire brought a customized playlist for the day to set the mood and even made me delicious breakfast potatoes because I mentioned that potatoes were my favorite food. Getting ready was more like hanging out with a bunch of close friends than anything more formal. One of my best friends was there and it was great to have a community for this day that I wanted to support myself. The actual photo session was so fun. Cheshire told me exactly what to do and it was obvious from his reaction when I had hit a pose that was right. I was nervous, having never taken professional photos before, but Cheshire was great at walking me through all the processes and folded in any of my ideas along the way. I wanted to re-create a pretty famous photo and was worried that we were trying too hard, but Cheshire was game for it and able to make it happen. It's one of my favorite pictures. We were even able to work in my dog to a few photos. From a few sneak peaks I saw on the day I knew the photos were going to be incredible. But going to the studio and looking through all of the amazing shots was a treat. It was hard to narrow down, but Cheshire was very helpful in figuring out just which ones were right. Even putting together the book and going back-and-forth on making sure each page was exactly what I wanted was a breeze and a lot of fun. One of my hobbies is doing puzzles and we shot a couple pictures with a jigsaw puzzle I had been working on. I wasn't really sure what kind of keepsake I wanted- hanging my photo on the wall didn't quite fit what I was looking for. So 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 specialtouch and a real testament to how much he thinks about each client and their specific wants and needs. If you're at all on the fence about doing this, book it. Book it today. It's such a great way to make yourself feel amazing. Cheshire will take care of everything so that you don't have to worry and will make sure it's a fantastic day. You end up with amazing snapshots of yourself right now and you will inevitably want to do it again. A few tips: Having a friend there as a cheerleader is amazing. It's great to have a team that you trust to experience this with. If you can bring somebody along, I highly recommend it. Don't go in with too many expectations. Cheshire is really good at crafting the moment, working in real time to make sure that everything is the way that you want. Include things that are personal to you. Being able to do this in my house that I have worked so hard to make comfortable and having all of my wardrobe available to me was really great. But if I had done it in the studio, I would have wanted enough of my real clothes that make me feel beautiful. It doesn't have to be sexy lingerie. Some of my most amazing shots are fully covered up. Make sure to get a keepsake for yourself. If you're making prints for other people, that's great, but it's really nice to have something for yourself. read more

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Appreciated the very warm educational exchange Chesire and I had. I knew not a thing about professional photography services.

Cheshire is such a professional - he is dedicated to his craft, makes you feel so comfortable during the entire shoot, and is very thoughtful. It's the finishing touches that make you feel like it's truly a pampering day for you - from the placard with your name on it, the platter of your favorite snacks, to the custom playlist, from start to finish the experience is not to be forgotten and well worth it! read more

Amazing! Amazing! So wonderful and professional! Beautiful photos and fabulous hair and makeup! They made me feel so comfortable and relaxed! The photo shoot was fantastic! read more

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. Not only did they turn out incredible, but they are a marker now of a new chapter in my relationship with myself. Also I can't emphasize enough how sexy you will look and feel. read more

In November 2023, I started my OnlyFans account. In November 2023, I decided that I was going to explore entering the world of adult content creation. However, in November 2023, I had very little content that I was able to my post to my OnlyFans account. As a result, in November 2023 and in December 2023, I commenced conducting Google searching and Yelp searching for a photographer or photographers that did or do naked photography, erotic photography, etc. During that period, I contacted via electronic mail (email) I believe three (3) photographers to see if any of them and/or all of them can help/assist me in creating adult content in terms of photography for me so that I can have a foundation to start with in terms of posting quality adult content onto my OnlyFans. One of those photographers that I ended up emailing was Cheshire Isaacs of Oaktown Boudoir in Oakland, California. I asked Cheshire if Cheshire worked with both men and women, or, in the alternative, if Cheshire only worked with women regarding his photography shoots, and Cheshire informed me that he worked (works) with both men and women when doing boudoir photography. Predominantly, Cheshire and I communicated via electronic mail. However, Cheshire and I did talk on the telephone on one occasion. During the course of our communications, Cheshire was absolutely outstanding in terms of explaining to me how he could help/assist me, making suggestions, advice, and recommendations regarding articles of clothing that I should wear, etc. Cheshire was also monetarily accommodating to me in terms of how much money he would monetarily charge me to do a boudoir photography shoot of me. Ultimately, I ended up hiring Cheshire, paying him his monetary required payment, and ultimately got a date scheduled to travel to his Oakland studio to conduct the photography shoot. Cheshire was (and is) really dope, really cool, personable, down to earth, a man that I can relate to a certain degree, easy to talk to, etc. I will also add that Cheshire was (and is) very patient in terms of me needing time to acquire the money needed so that I could pay him, and me needing time to figure out my schedule so that I could conduct the photography shoot so that it would not conflict with my day job. Ultimately, in February 2024, Cheshire and I met in person at Cheshire's Oakland studio, and we got to work. The photography shoot was phenomenal. Cheshire was (and is) an absolutely fabulous director in terms of what he wanted from me in terms of positioning, look, style, etc. I loved taking Cheshire's direction, instruction, etc. However, at the same time, even though professional photography is not my lane because I am not in this profession, Cheshire encouraged me to have input as well in terms of creativity, ideas, etc. Cheshire was extremely welcoming when I arrived at his studio, including providing snacks for me if I got hungry. The experience with Cheshire was absolutely off the chain, and I am excited to do another photography shoot with Cheshire in the future regarding putting more high quality content onto my OnlyFans. The final product turned out fantastic. Thank you, Cheshire. I appreciate it. read more

I did a mini session with Cheshire back in November and it was lots of fun! It was my first time doing a professional photoshoot, let alone a boudoir photoshoot. Cheshire was really meticulous and it really shows. He definitely read the pre-session questionnaire and responded to my questions. He also detailed how a mini shoot compares to a full session. Also didn't forget to play Carly Rae Jepsen to my heart's content during the photoshoot, lol. The actual day of the photoshoot, Cheshire showed me around the studio and let me choose one of two locations for the photoshoot, the stairs or the window. I was a bit shy so I chose the window since it was darker, haha. But Cheshire discussed how the session works and asked me what kind of poses I wanted, if any (I wanted to showcase my engagement ring so we definitely got to do that) and made me feel comfortable. Don't worry if you don't know how to pose, Cheshire will direct and show you! It was supposed to be a 20 min session but Cheshire actually took a little more for me and I'm super appreciative. The proof shots came out great! I didn't even think they needed to be edited further but I did eventually choose 3. Overall, the whole thing was really fun and not scary at all. Even though I was nervous at first, I was able to relax later. Wouldn't mind going back for a full session next time. read more

This is your sign to take the leap and reach out to Cheshire! If I could give more than 5 stars I would. From start to finish, he was incredibly gracious and meticulous and made me feel incredibly comfortable throughout. Prior to the photoshoot, we were in contact to figure out details, as well as confirming ideal hair/makeup with D, who was also wonderful - the pampering is a great way to ease in! He takes care to understand your comfort level as well as preferences, and easily pivots to tailor the experience to you, from the shoot itself all the way down to customizing playlists based on your favorite music to help you feel at home. 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 and I'd love to do more shoots in the future! I have recommended to any friends who are on the fence. read more

What an amazing experience. I did a mini session with Cheshire after missing an event he did so I jumped On the opportunity as soon as he posted again. I have several friends that have booked with him so I knew I was in good hands. This event had a PopUp lingerie shop to go with my holiday boudoir session. The studio was lovely and had amazing lightiing. After picking my outfit, we started our short but sweet session. I'm not a shy person but his cool gentle demeanor really had be 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. I can not wait to book a full session read more

Cheshire was the best! He is very responsive and professional, I appreciated that he took the time to get to know me and what my goals were for the shoot. During the shoot, he arranged a wonderful makeup artist and was kind enough to take some dating shots in addition to his usual boudoir photos. The setting is very comfortable and allowed me to be my best despite how nervous I was going into it. Cheshire was kind enough to turn around some photos in a short time frame, and even adjusted the lighting on a photo for me. The finished product was amazing, everything that was promised! I am so so happy with my experience, and know that Cheshire always has my best interest at heart. read more

I did a shoot with Cheshire as a birthday gift for my partner, and also a gift to myself. It was an absolute dream from start to finish! Cheshire is incredibly communicative, and made sure to ask a lot of questions in a survey ahead of time, to get a feel for what I was looking for, any specific requests, and/or any comfort level boundaries. I immediately knew I was in good hands! 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. The studio itself is amazing, in that it has so many possibilities in a deceivingly small space. Everything from bright gleaming natural light, to dark moody shadows, and everything in between. We shot for several hours and it was a blast the entire time. He'll play your music, provide you with snacks and drinks, and most importantly - lots of encouragement and instruction in front of the camera. We got such a wide variety of shots, I was absolutely elated! A few weeks later, I have an incredible leather-bound book in-hand, as well as a USB full of even more shots. I cannot overstate how amazing the whole experience was. 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, and you'll get to create some incredibly beautiful images together. read more

I got a mastectomy in January and at the last moment I decided to get some boudoir pics to commemorate the change in my life. Cheshire worked with my friend to quickly arrange a photo shoot within days of initial contact. Cheshire made the day super easy. I had my reservations coming into the session but all anxiety was gone sighing 20 min of starting. If you are looking for a mello photographer with lots of great ideas look no further than Oaktown Boudoir read more

I cannot say enough wonderful things about Cheshire! I've had the pleasure of shooting with him twice and both times he created absolutely stunning photos! I felt completely at ease with Cheshire, and had such a great time both times I shot with him. His studio is comfortable and very versatile for creating a variety of looks. If you're looking for a boudoir photographer in the Bay Area, I highly recommend Oaktown Boudoir!! read more

Dragonfly Boudoir - Session Photography Near Me - Oakland, California

If you're thinking about doing a Boudoir shoot I cannot recommend Oaktown Boudoir enough. Cheshire (photographer) is extremely kind, communicative and professional. The makeup artist/hair stylist he works with is also amazing and totally worth the extra fee. I booked a shoot with Cheshire to celebrate my 30th birthday in an attempt to embrace my body and increase my self love a bit. I was a bit nervous, because I absolutely HATE taking photos and I tend to look super awkward in them. But Cheshire immediately put me at ease and guided me through the shoot which resulted in some amazing shots. I now have a cute leather bound book of my boudoir shots, a massive black and white print of my boobies on my wall and some great photos for social media to share (yes..you don't have to get naked in ALL your boudoir photos, haha). read more

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 studio is stunning! I got pampered with hair and makeup while drinking champagne. Total luxury! I felt really awkward posing at first, but Cheshire coached me through it and got me feeling myself by the end. I was blown away by how many different scenes he could set up in his studio, just by changing the lighting and moving the furniture. When he sent me the final shots, I couldn't believe it! They turned out SO AMAZING! I had trouble narrowing them down to put in the book! And when the book arrived, it was beautiful quality. The layout, printing, and weight were just perfect! If you're thinking about doing some boudoir shots, book with Cheshire! The whole experience was seriously amazing! read more

Stop scrolling and book now. You will not be disappointed! I have always been one of those girls that though it would be really cool to do something like this when I loose a little bit more weight.. and naturally never reaching my "ideal weight" and never have a photo shoot! That all changed when my sneaky sister-in-law gifted me a surprise photo shoot for a wedding present. She shows up on my doorstep with a razor, shaving cream and lingerie! I freaked out... but was incredibly excited. And then nervous, I couldn't mentally handle seeing bad pictures of myself right before my wedding. But those were all silly thoughts! From the moment I met Cheshire and his team I was immediately at ease. I had some nerves going into it knowing that he was a male, but meeting Cheshire it is eminent that he carries himself with the upmost professionalIsm and is super personable. He provided a beautiful fruit and cheese tray while I got my hair and makeup done.. and also let us hook up to his speakers to play our jams! He walked me through every pose.. telling me what I should do with my face all the way down to my toes! I was on a time crunch and really wanted to gift a book to my future husband. Cheshire absolutely made it happen, he was so flexible with meeting up to view the photos even down town to squeezing me into his busy day to pick up the final book. I 1000% recommend Cheshire and look forward to working with him in the future! read more

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When almost every day on my calendar is booked It's easy to lose the excitement over the appointment its self. The note on the calendar read Photo Shoot. For some, the title alone might elicit excitement and anticipation. For me, my brain just rolled it into the hundreds of other photo shoots I've worked on over the years. I had no idea how much this shoot would mean to me. I own a lingerie company. For twenty years I've been helping women find their joy in their bodies, relationships, and wardrobes. My business has been seen in Forbes, Glamour, CNBS, CBS, and many more. Media is a huge part of my business. I've worked with many extremely talented photographers, models, and producers. Many of the photographers we partner with shoot boudoir photography as part of their own business'. Photographers frequently offer me my own boudoir session. I always say no. I never really had a reason, I just didn't feel I needed one. Then my friend Cheshire at Oaktown Boudoir offered me a boudoir session. I reflexively said, "no." Then I thought about why I hadn't done my own shoot before. I know I'm beautiful. I'm not twenty, I'm forty four. I'm not a size two, I'm a ten. The fact is, I just didn't think of myself as great lighting, and soft sexy fabrics, kind of beautiful. I thought of myself as a beautiful on the inside and outside, mom, CEO, makes you smile because I'm smiling, kind of beautiful. Intellectually I know we can be both. Ironically, I preach this all the time to others. I had just gotten so busy, I forgot to celebrate the many parts of me. The day came for the photo shoot and I arrived still in business mode. I checked out the studio, assessed and admired the equipment, met the makeup artist, and sat in the chair. Then everything changed. I'm used to getting my makeup done for interviews and media. This was not that. The makeup artist had lashes, lip gloss, and a serious curling iron. Then she handed me a mirror. OMG! Who is this hottie staring back at me? I was stunned. I hadn't given myself the space to look like that in years. It was amazing, and it was only the beginning. I knew I would feel completely comfortable with Cheshire during the session. However, 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. I felt beautiful and empowered the entire session. Cheshire is so easy to be with. He makes the whole experience feel quite natural and fun. During the shoot Cheshire had shown me a few pictures on his camera. I could tell immediately that they were going to be good. As our session ended I found myself really looking forward to seeing the final product. I haven't been so excited to get pictures back since my wedding. The anticipation and excitement was delightful. I actually felt giddy! What fun! I know I've said, OMG, but OMG!! Words failed me for quite a while when I saw the pictures. I could not have imagined myself looking and feeling this way before my session. I didn't realize how much I needed this transformative experience. I have so many levels of gratitude and joy in this experience. I'm grateful to Cheshire for having not only the technical skill, but the kindness, and vision, that this was an experience I would get a lot out of. A boudoir photo shoot is a photo shoot unlike any other. read more

Here's the situation: You're feeling pretty good about where you are in life, and you wanna celebrate yourself. "I deserve this, dammit," you think. So you hit up Cheshire at Oaktown Boudoir (You follow @oaktownboudoir on IG, so you already know his work is #classyaf), and schedule your first-ever boudoir photo shoot. You don't know it quite yet, but you've just made one of the best decisions EVER. I did not expect to have as much fun as I did on the day of the shoot. I'm a formerly super self-conscious plus size woman, so I felt a bit of trepidation when I arrived for my shoot with Cheshire. (Looking back, I don't know why I was so nervous-- Cheshire dedicated tons energy ahead of time to getting to know me and my vision for the photos he would be taking-- but I'm only human, so I was nervous.) Within minutes of Cheshire showing up, all doubt flew out the window and I was having the time of my life. I don't know if it was the fact that he immediately fixed up a cheese or fruit platter for me to snack on, or the fact that he hung out with me while getting my makeup done, but I felt SO comfortable in his presence. So, by the time we finally got to taking the photos, I felt more confident and sexy in front of a camera than I ever have. Listen, I love taking selfies, and I like to think I know my best angles, but HOLY TOLEDO, Cheshire just knocked it out of the park. He knew which poses would make my body look amazing and gave me all the direction this boudoir first timer wanted (and needed). I was also astonished by the magic Cheshire creates in his studio. He knows the natural lighting in that space like nobody's business and uses it brilliantly. He checked in frequently and gave me glimpses of the photos he was taking, prompting me to (rather inappropriately) yell "Yoooooo, Cheshire! I look SOOOO hot!" We played off each other's energy and created some FIRE photos. The photos speak for themselves. Even unedited, you come away looking and feeling like a million bucks. If you're on the fence about working with Cheshire, or about doing a boudoir shoot in general, climb down from that fence. Climb down from that fence, go inside, and email Cheshire to set up a session. You won't regret it. read more

Dragonfly Boudoir - Looking FIRE, thanks to Cheshire! - Session Photography Near Me - Oakland, California

If you are looking for an amazing photographer who will make you look and feel like a million dollars oaktown boudoir is your person! I can't wait to do another session! read more

I did a boudoir maternity shoot with Cheshire and had a really great experience. He was really good at communicating every step of the way. I wanted to do something totally outside of my comfort zone to embrace my pregnancy and everything that comes with it. At first I was a little hesitant to do a Boudior shoot, but after communicating with Cheshire, I felt comfortable. On the day of the shoot, I was open to letting Cheshire use his artistic creativity and I'm so glad I did. The photos came out way better than I could've ever imagined. He was very professional and super down to earth. I was shy for the first couple of shots, but after getting to know Cheshire, I was super comfortable and felt like I was being photographed by a friend. I wasn't going to share any of my photos with anyone because I was too shy, but after seeing this one, I gave Cheshire permission to post my photo. I want to inspire other pregnant women to embrace their bodies and capture this amazing part of motherhood. Thank you so much Cheshire for an amazing experience and for the beautiful pictures that I will cherish! read more

Dragonfly Boudoir - Boudoir maternity - Session Photography Near Me - Oakland, California

So many great things about this place. Let me start with how amazing this studio is. It's spacious, very clean, and has lots of natural lighting. There are many different scene setups you can do for your photo shoot. And lots of street parking around the area. Cheshire, the photographer, has mad skills. His work is very impressive. He's open to all ideas and suggestions. Right away he made me feel very comfortable. He has great energy which helped bring out my inner model. read more

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Cheshire was a DREAM to work with. I had never done photos like this before and he made me feel so comfortable and confident! His studio was clean and professional and the pictures came out exactly how I wanted! Couldn't have asked for a better experience! Got a little book for my future husband and can't wait to give it to him! read more

Dragonfly Boudoir - Session Photography Near Me - Oakland, California

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If you've been waiting for "that one review" to really prove that Oaktown Boudoir is the way to go- don't wait anymore! Cheshire Isaacs is a true exemplar of all that a professional boudoir photographer should strive to be. He is open and receptive to his client's ideas without losing focus. He is honest and genuine without ever being insensitive. He is incredibly professional without ever being stuffy. The Bay Area is filled with Boudoir Photographers, so I guess the best way to write a proper review is to outline what exactly my own (popular) concerns were and how Cheshire proved triumphant! 1. Will I be comfortable? As a young woman, I was a little concerned about being erotically photographed by a man. Having been through a shoot, it's obvious that Cheshire cares- from his personally designed music playlists (made in the interest of making the experience as comfortable as possible) to his handmade cheese and cracker platters. He continually went above and beyond for my session and I admire his passion, enthusiasm, and dedication. It shows in both his beautiful work and the long-lasting relationships he has with his clients. He spoke about his wife and daughter frequently, something that showed me his appreciation and respect for women, immediately putting me at ease. 2. Can his studio fit more than one "style" of photoshoot? Cheshire's studio is open, bright, and filled with possibilities. He can transform the space to fit, I kid you not, any personality and style. In a matter of minutes (just enough time to refill a wine glass), his studio can go from a brightly lit angelic state to a dark, sexy, and sultry one. He mentioned having custom-designed the space alongside his wife, something that told me just how invested he was in the style and overall vibe of his studio. For my images in particular, I knew that I wanted little editing and wanted the images to be as "real" as possible. Somehow Cheshire still made it look like I was a model and knew exactly how to manipulate each pose to accentuate all the good and cleverly soften all the bad (without photoshop). 3. Will I get my money's worth? Whichever amount of time you decide to book Cheshire for, know that not a minute will be wasted. He knows how to get down to business and not waste time while simultaneously not rushing through any poses. This guy was sweating as he climbed up and down ladders, moved heavy couches and bed sets, and adjusted lights. His hard work pays off in the beauty of his finished products! His experience in the field is obvious in the way he can quickly evaluate a pose and make small nuanced changes in position to get a desired look. I am but a poor college student and Cheshire's prices were definitely better than most photographers around. He could easily charge three times as much for his services and would still be the deal of a lifetime. 4. Will my images be published? Cheshire was very thorough and attentive when listening to what I was comfortable with. He assured me that no images would be posted without explicit approval. In the end, his work was so beautiful that I would have been fine with it being printed on billboards and bus ads- really! 5. What about makeup? Cheshire notified me in one of our first correspondences that he had a partnership with a makeup artist, Thuy, who would be on-site for a small fee. Let me tell you- Thuy is more than simply a makeup artist- she really does it all. Not only did she do an absolutely spectacular job with my makeup, but she was the ultimate hype-woman!!! She stayed for nearly the entire session for touch-ups, glamour, and enthusiastic words of support. The experience wouldn't have been the same without her. Every person that sees the finished images says, "Wow, I wish I'd done something like this." Don't be that person! Don't wait another day, don't look for another review, don't google "Boudoir Photographer" again. Oaktown Boudoir is that good. Doing a boudoir shoot is obviously a large lump sum of money to dedicate to something that isn't necessarily "necessary," but my experience with Oaktown Boudoir is something that I will truly treasure for the rest of my life and always reflect on with a smile and a deep, deep appreciation for Cheshire Isaacs! He knows how to make a client feel like a friend, and that's something you don't come by often. read more

Dragonfly Boudoir - Group shoot! What a blast! - Session Photography Near Me - Oakland, California

It was an absolute blast working with Cheshire. I had never done a boudoir photo shoot before and he made me feel very comfortable. As a blind person I wasn't really sure about what my options were in terms of lighting and posing with different types of moods and settings. He took all the time to answer my questions and really explain things in great detail breaking down all of the different types of genres that he works with and giving me examples of things to choose from and try. He really went above and beyond and even learned braille to make me a braille welcome sign. This really meant a lot to me. Cheshire took all the time to get great photos and really helped me figure out what style I liked and how to make me feel empowered. It was a really great and fun experience we had some really wonderful conversations as well from the foods he provided and where they came from to the music I like as well as other topics like heteronormativity and stereotypical gender roles and poses. As a gay woman this is something that I am also conscious of as he is a straight man but at no time did I feel awkward or uncomfortable. He understands what this represents and really is interested in being aware of how his position effects people in various minorities. The make-up artist was also lovely and she really found what style was true to me. He also had so many options for different scenes and settings in his studio space with lots of natural light as well. I also really appreciated that I didn't face any kind of ablism or negativity surrounding why I was in the space and wanted to be there. So many people have questioned me as an LGBT person and as a disabled person and he was great with it. Thank you to everyone else who gave so many good reviews because it made choosing Cheshire an easy choice. I could also tell from our first conversation that he was very open to making me comfortable and also learning together what would work. How to help give me direction and how to also let my own ideas and thoughts flourish in a safe space of fun and exploration. You can tell he is really in it to be there to support clients and health and express what they want to express. He also took the time to figure out how to make things as accessible to me as possible. He sent me some sneak peaks 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 and his care about his work and the people he works with. I would absolutely recommend him for any sessions. read more

Cheshire was AMAZING! Seriously, I cannot recommend him highly enough. Here's why I loved working with Cheshire: 1) Creative: I wanted to do kind of a "twist" on traditional boudoir but didn't know exactly what that meant. Cheshire helped me brainstorm, create a vision, and bring it to life! 2) Teammate: This truly felt like a creative partnership, not a service. Cheshire was there every step of the way: to answer questions, provide inspiration, help me make decisions, etc. 3) Accommodating: I was apprehensive at first about doing a Boudoir photoshoot in general, but Cheshire not only made me feel comfortable...he allowed me to THRIVE! I ended up doing shots I never thought I would do just because he was so comforting the entire time. 4) Above and beyond: Cheshire really goes above and beyond in making the shoot/final products everything I wanted. From going out on the spot during the shoot to get a rare type of fabric we needed, to finding the perfect secluded local outdoor space, to editing things to be exactly how I was envisioning....I was just constantly impressed with the level of detail and length Cheshire would go to to make his clients happy. 5) Real: Compared to other boudoir photographers, Cheshire is NOT over the top with his process or prices. I really appreciate how he values his clients' time and money. Seriously - just hire him!! You won't regret it :) read more

I really enjoyed working with Cheshire! This was my first time doing any kind of photoshoot, let alone a boudoir shoot, and he went out of his way to make me feel comfortable and beautiful. Before the shoot, he sent over some resources to help me understand what to expect, and they were really useful in getting my ideas organized.  During the shoot, Cheshire took a ton of time to make sure we got all the shots I wanted, and I ended up with hundreds to choose from for my book. I was super impressed with his professionalism, especially before and after the shoot; he was incredibly responsive via text and email, and sent me updates and drafts as soon as he had them. He also made sure I was 100% happy with the prints and touchups before sending to print- no pressure at all.  Cheshire's prices are incredibly reasonable, and Rachel, who did my hair and makeup, was delightful. You can tell they have great respect for each other's work, and I think it showed in the product (me!) I'm very grateful to them both for creating such a fun environment, and I CAN'T WAIT to give my soon-to-be husband the book! read more

Cheshire was awesome! He is very professional and has creative skills that will engage you and make you feel like a supermodel. The shots and set he had made the experience fun. He was also great to collaborate with ideas. If you are looking for a photographer for any theme, he is the man! read more

What is there to say besides I had the most amazing experience from the moment I emailed Cheshire. He was so helpful as I emailed him asking questions, developing the plans and trying to figure out what I wanted to do and how to make my photos special. Every step of the way made me feel comfortable. The session at the studio was a BLAST. I was nervous I was going to be awkward or uncomfortable but the whole experience was far from that. He had my favorite music playing and created a space that was fun and comfortable. I never thought I'd enjoy my experience as much as I did. I truly had a blast. I felt empowered and it was just so fun getting to be that comfortable in my skin in front of a camera. Plus, the photos came out AMAZING and the book we created is incredible. This was a wedding gift for my husband and it was the hardest secret I kept because I wanted to tell him all about the whole thing from the moment I walked out of the studio (and then I couldn't stop telling him every moment once I gave him the book... which he absolutely loved). Anyways, you truly can not go wrong with Cheshire. The studio is SO unique and has so many options to get creative with the walls, lighting and items. I can't speak highly enough of my experience and what he brought out of me! read more

I had the most amazing experience with Cheshrie & Racheal! They made me feel so comfortable, like we have known each other for years. The studio is perfect to capture thoes seductive/playful pictures. Racheal did an amazing job with my hair and make up she really read my mind in how i wanted to look which made me feel even more confident. Cheshire is a genius photographer. After meeting him and showing my inspo board he really took it to a whole other level. Im so happy with how everything is turning out and can't wait to see the end product. This is a huge deal for me since I want to capture my playful 20s but also for my husband as a birthday gift. Cheshire, thank you again for your amazing work, attention to detail and your passion for the art of photography it really shows. read more

I was nervous about doing a boudoir shoot but really wanted to surprise my fiance with a book on our wedding day. This was definitely out of my comfort zone and I never tend to love how I look in any pictures - so I was extra hesitant. But from the moment I started working with Cheshire, I felt super comfortable and excited! He even made a custom playlist (and had some champagne ready) to make me feel more at ease. Cheshire was so amazing to work with, I could not have been more happy with how the shoot and book turned out. He went above and beyond to make me feel comfortable and to ensure the pictures turned out amazing! Thuy did my hair and makeup and did an absolutely amazing job! She was there throughout the shoot to refresh my makeup and hair which also helped put me at ease! From the time I saw the proofs to when I received the final book, I was blown away by how amazing the pictures were. Cheshire does amazing work, and I could not have been happier with how everything turned out! If you are thinking about doing this - just do it, you will not regret it!!! I am so happy I did - and so was my fiance :) read more

Cheshire's is a kind, dedicated, thoughtful and talented photographer who runs Oaktown Boudoir. I highly recommend him for your your photography needs, especially boudoir/lingerie photography. Cheshire Issacs produces crisp clear images with an intimate style . He has quality equipment and his eye and perspective truly sets him apart. He and his studio are welcoming. The studio is not huge, but the equipment and sets he has available can transform the space into many different styles and areas to shoot in. I've shot with him twice and none of the images look the same because he has lots of options available. Despite being a man, he's able to make subjects feel comfortable even when showing a lot of skin. I highly recommend Cheshire if you are hesitant about shooting boudoir. read more

If you're reading this to find out more about Oaktown Boudoir... STOP! Just email Chesire and DO IT! I wanted to make a boudoir book for my fiancé as a wedding day gift. I started my search initially through Groupon which then led me to Yelp and finally Oaktown Boudoir. I emailed and Chesire quickly responded. He was extremely helpful in answering all my questions and helping me set up an appointment to meet and plan for the photo shoot. Please don't mistaken his quick response as a pressure to do business but rather his enthusiasm (not once did I feel pressured). He offered exactly what I had envision for the gift (a small fold out accordion book to be given on the wedding day... did I mention at an absolute steal of a price?!!). We quickly clicked and planning was absolutely a breeze. Don't be fooled by the studio and it's "small appearance" from the outside. Inside is amazing. The studio has many different rooms and Chesire is able to recreate any backdrop you envision. I looked to his Instagram page to provide samples of what I wanted. During our initial meet we planned out the different pictures I would like to have taken and discusses timing to utilize natural lighting as much as possible. Now for the actual day...I was so nervous. It's not everyday I'm taking photos in lingerie, let alone in front of strangers. Hair and Make Up was completed by Make Up Artist Thuy. They have been working together for some time and you can tell by the chemistry they have. She worked on my hair and make up and was a complete sweet heart. She made sure the make up I had I felt comfortable with but still a bit dramatic for the pictures. To calm my nerves he has an array of beverages (which included bubbly at my request) Oh wait did I mention a cheese, crackers and fruit platter?!?!?! Music was playing while we got ready. He ever contacted me before to inquire about my music taste so he could make a personalized playlist for the photo shoot. The photo shoot was amazing. Thuy stayed and helped with my hair and make up in between photos to ensure I looked amazing. We shot for several hours but only because Chesire wanted to complete and be able to take all the pictures I wanted. If you're wondering about the extra time and if I had to pay extra...he didn't charge me. He wanted to make sure he got all the photos and I would be happy (I just made sure I included a tip to make up for some of the time) The pictures came back rather quickly and boy were they amazing!!! He not only captured my natural bubbly self but also captured this seductive-lip-biting-bra off side I didn't even know I had!!! When it came down to picking out the photos for the book...it was so hard because we had sooo many good photos but Chesire definitely took the time to help me pick out the photos and was extremely patience with all my corrections and edits. We probably made about 10 different drafts before we settled on a final book. If you're wondering what my fiancé thought of the book...some things are better left as a secret ;) read more

When we walked into the studio a little bit early, Cheshire was just setting out a plate of fruit & cheese for us. He'd also put up a welcome board with our names on it. And, to seal the deal, he had some bubbly on tap! Needless to say, he's extremely attentive and fully dedicated to his clients having a grand time. His care is matched by his talent. All his shots of us as a couple were fantastic. He ensured we were comfortable, offered his ideas while being flexible with ours, and shot for hours. And we had fun! It never felt weird or boring. After the shot, he scrambled over Thanksgiving to ensure we had the photos quickly. He's really top-notch, in every possible way. Thank you, Cheshire! read more