Sienna Sinclaire Stripped

No one dreams of being a stripper when they grow up, but maybe they do now as times and attitudes have changed.


For me, it was more financial freedom to travel, save and buy nice things all on my own.


I had just moved to DC and the city was very expensive to live in, so it was either move away to a more affordable city or make the transition to stripping.


It wasn’t a decision I made quickly as I was torn between whether or not I should do it.


I had just moved to DC from London where I was working at a magazine for an internship and I had decided to turn down my Masters Degree in International business, as I didn’t want to work a 9 to 5 job or for someone else.


I wanted to work for myself but I didn’t know what yet. All I knew was I wanted to travel more as I loved all the traveling I did when I was living in London, but I needed money to do so.


So I figured for my 20s I would travel and spend time "figuring it out” as I enjoyed myself.


But making the decision to strip was a difficult one for me as I knew my family and friends would find out.


But it wasn’t just that, it was having to be able to look at myself each day in the mirror and be fine with what I was doing.


So I thought long and hard over my decision, took about a month, but working as a waitress in the strip club also helped to see what it was really like to work at one.


It’s one thing to be fine with someone else doing it and having fun watching them, it’s a whole other thing to actually do it yourself.


Once you go there, you can’t go back. So I wanted to make sure I was making the right decision, along with not spending all my money that I made stripping and having nothing to show for it.


My other decision besides just traveling, was to save money for a future business. I wasn’t sure what I wanted to do yet, but little did I know that becoming a stripper would lead me to my dream job as a Naughty Girl and help me become the person I am today.


Sienna Sinclaire Pink Bikini 

Body Confidence

I’ve always had a lot of confidence in myself and my body. I grew up with parents being comfortable being naked, and I’ve had no problems being the one in the dressing room to get naked out in the open.


But getting naked in front of a bunch of strangers where you are the center of attention is another story.


I’m not someone who seeks attention but I don’t mind it from time to time.


Getting up on stage for the first time, I was very nervous. So I invited all my girl and guy friends to come cheer me on my first night and to bring some money just in case no one tipped me…lol!


It helped me not to feel so nervous and felt good to have them cheering me on and supporting my decision as none of them judged me. Plus I think my guys friends enjoyed finally seeing me naked!


But once I got on that stage, along with playing my favorite music, it’s like I transformed into another person. I felt more confident all of a sudden, like I had this power over me, making me feel sexy like a goddess.


I got really into it and had a blast my first night. Plus the crowd were lots of regulars who I had served cocktails too, so they all knew it was my first time and were super supportive too. And when you’re new on stage, they tip you $100 bills. So I made a killing that night.


I was on top of the world when I went home and in one night I had enough to pay my rent, car, credit card and more.


I knew from that night on, this was my way to financial freedom. Plus stripping is what helped me to love my body more, not afraid to show it off and build more confidence.


It helped me in SO many ways, and everyone will have a different journey when it comes to stripping. For me it was life changing and another chapter in my life that helped me on my path to where I am now.


Sienna Sinclaire St. Barths

Financial Freedom

Becoming a stripper wasn’t about taking my clothes off, it was about financial freedom, to do what I want and support myself.


I started off stripping in DC but eventually went to NYC to make better money, and ended in Vegas.


When I was dancing in DC, customers kept telling me that I could do much better in NYC with making more money. And I’m all about making the money so off I went!


I drove to NYC one day and walked into Scores for an interview, which consisted of getting naked on the stripper pole…lol!


I was hired right there, quit DC and started working in NYC the next week.


Boy where they right, I was making WAY more money than I had in DC. It was insane amounts of cash.


I started saving immediately. I wasn’t buying expensive cars or designer clothes. I still drove my Hyundai Sante Fe and wore clothes from Bebe, Limited and Express.


As I said before, I wasn’t going to strip and have nothing to show for it. The only money I spent was on was my rent so that I could live somewhere nice and on my travels.


When I traveled I would stay in hostels from $10 to $20 a night and spending $50 to $100 a day for expenses. 


Even though I was making up to $50k a month I wasn’t spending it on first class air travel or 5 star hotels when traveling.


Every now and then I would splurge, like in the photo above, where I took my aunt to St. Barths and I paid for bottle service at the club with some friends we made. But I was very careful with my money.


I was traveling the world, having an amazing time but doing it on the cheap, because I was serious about saving my money so I could save to buy a house and start a business.


And all these things I’ve done!


Now I travel first class, stay in 5 star hotels, buy designer clothes, and drive a Range Rover. But I’m in my 40s now and it’s been about 18 years since I first started stripping, so I’ve saved a lot of money and made money with my businesses and investments. I now have the money to spend without worrying.


It wasn’t something that happened overnight, meaning it took me time to save, invest, buy a home, start a business, etc.


But for me, I was on the right path with stripping because it was giving me everything I wanted and that was financial freedom.


Sienna Sinclaire Naughty Los Angeles Travel Book Award

My Naughty Businesses


Stripping was just my starting point, I did a lot more in the naughty world that I’ll cover later in more blog posts.


I only stripped for about a year and half, but it was a great learning lesson for me and to help me on my path to exploring my naughty side.


Yes I did it for the money, but the more I stripped, the more I realized how much it was helping me for what I was about to become.


I realized that you could make a killing in the naughty world but you can’t let it suck you in or else it will spit you out with nothing to show for it.


I knew that if I did this right, I could make a lot of money along with turning this into a business. Not turning stripping into a business, but exploring the naughty world more and finding my niche.


And that’s exactly what I did with exploring the fetish world, I became a burlesque dancer, pinup/fetish model, I started taking sex coaching classes, reading books and watching documentaries about the naughty world and SO much more.


I even wrote five naughty travel and history books, where two of them won awards.


I was living the Naughty Lifestyle and surrounding myself in it from all that I did from work, travel to naughty parties.


I wasn’t just learning it, I was living it and helping others to live it too.


After exploring the naughty world, this is when I decided I would definitely turn it into a full time job.


It took baby steps to get to where I am today, it didn’t just happen over night.


It took years of learning from stripping, modeling to sex coaching classes to perfect my business and what I wanted to do.


And now I have a thriving naughty business that’s still growing as I learn more.




1 comment

  • LaTi

    I really enjoyed reading this and learning more about you ! You used the profession well to save and think long term vs. short term which was definitely one of the keys 🔑 to your success . ❤️

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