My Life Milestones

By Kendra Holliday | May 4, 2017

I’m 44 years old. Here is my life trajectory so far:

1973: I’m born in North Dakota. Brrrr!

My birthday suit, aka my first nude photoshoot

My birthday suit, aka my first nude photoshoot

1974: My family moves to Dallas, Texas.

1975: Who the hell knows.

1976: My brother is born.

1977: Um, Elvis dies?

Drinking the blood of Elvis

Drinking the blood of Elvis

1978: My sister is born. My brother throws up. I remember my first dream; I’m kidnapped by Captain Hook and held hostage with Raggedy Ann and Andy. He cuts off my foot and it looks like SpaghettiOs.

1979: My family moves to St. Louis.

1980: My baby brother is born, and dies two days later. My mom tries to kill herself several times, and when that fails, she burns his name into the back of her hand with a soldering iron. She is never the same again. A very dark time.

1981: Life still sucks. My mom is a complete wreck.

1982: My brother is born. My grandmother dies.

1983: I get molested by an older, adopted brother. It SUCKS. I get sent to therapy, and I don’t know why. I think I’m being punished. I am a victim.

1984: I have my first lesbian encounter. It’s hot and naughty. I’m 11.

1985: My baby sister is born. I drop her on her head, but don’t kill her. Skeptical about god’s involvement, I become an atheist.

1986: I hit puberty and middle school, and lose all my artistic talent and confidence. My family is poor white trash, and I am branded a zitty nerd. It sucks.

1987: My mom keeps getting crazier and crazier. It makes me crazy, and I attempt suicide. I spend time in three different mental hospitals. I lose my virginity to a 24 year old creep with a mustache because he keeps badgering me and I finally give in. It sucks.

1988: My moms tries to kill herself again. I put pressure on her slashed, gaping arms as my dad calls the ambulance. She gets hospitalized a lot, and OD’s, and gets shock treatment. I fuck around and feel very confused. It sucks.

1989: I have my first threesome. It’s perverted and awesome. I make a pact with my boyfriend to have sex every day for one year. Of course we succeed in this challenge.

1990: I get engaged to an abusive dickhead. I come to my senses and break it off with him, but not before I cheat on him a lot.

1991: I’m 18. I graduate high school. THANK GOD. I get kicked out of the house for not emptying the dishwasher. It wasn’t even my turn! I’m homeless.

High School Senior Pic

High School Senior Pic

1992: Desperate, I get a job as a stripper. My stage name is “Glamour”, hence the glamour shot. I have no tits and I can’t dance. Men take advantage of me; I’m only 19. It sucks. I have my first orgasm, which is pretty awesome. I am a survivor.

My hair color is "Starlight Blond"

My hair color is “Starlight Blond”

1993: I quit stripping and drive straight down to Louisiana to see my long-distance girlfriend. It’s awkward; after a year of passionate love letters, we break up. I move back to St. Louis and shack up with a guy and get a job at a nursing home. It sucks.

1994: I start nursing school, then change my mind. I don’t want to work around blood and shit and fluorescent lights all the time. I have careless casual sex and get pregnant. I try to get an abortion, but they turn me away because it’s a blighted ovum. I miscarry in Noah’s Ark Motel. A few months later, I am raped, but luckily I don’t get pregnant this time. I turn lesbian for a few months. I work at a nursing home, because I don’t know what else to do.

1995: I meet the man I will marry. My biological clock strikes at breakfast over pancakes at IHOP. We get engaged and go to Cancun and visit a Mexican whorehouse. It kindof sucks.

1996: We get married and settle into a boring, monogamous life. I’m 23. I quit my job at a Pediatrics ICU and get a job at a bookstore, and I love it. It’s SO much better reading stories to children than dressing their burn wounds.

1997: We go to Florida and Colorado a lot. I don’t really like Florida. Colorado is okay.

1998: We try getting pregnant. It’s not working. I’m freaking out and sex is becoming a chore. It sucks.

1999: I get pregnant, and miscarry, and it’s tragic.

2000: My daughter is born, and I am so happy. But damn, is it hard!!! I breastfeed her for a year.

Brand new mother

Brand new mother

2001: We move to Columbia, MO, where our marriage goes down the toilet. My grandfather dies, then my other grandfather dies two months later.

2002: I make a list of all the people I want to fuck, and leave my husband. I do it all wrong.

2003: I’m 30. I start swinging. It’s awesome. I move into an apartment and have a long distance relationship with a guy who claims to be a feminist, but is kind of an asshole. He tells me he wishes my tits were bigger, and for 24 hours, I contemplate getting a boob job.

I weighed less a few years ago.

I weighed less a few years ago.

2004: Instead of getting a boob job, I break up with that guy, and get back together with him a few times and date other people and it’s all a big mess. I get engaged to him, and then break it off. I go to Hawaii.

I did the shark cage thing.

I did the shark cage thing.

2005: I continue having sex with lots of people, and go through a cougar phase. I have a harem of men in their early 20’s who try and impress me and each other with their sex skills. It’s pretty fucking awesome. I learn how to squirt. My grandmother dies; the last of that generation.

2006: I get fired from my job for flashing a bartender in San Francisco after my office mates visited a strip club. I’m the only one who gets in trouble. I start sex blogging. I try an experiment where I become a Craigslist escort. It’s kind of awesome.

2007: I meet a guy and he wants me to quit doing sex work. I agree, and I move in with him and we go to China. We get engaged. I get pregnant, and have an abortion. We try having a triad and it’s great for three months, but then implodes. I break off the engagement and move out of his house. I am homeless.

2008: I fall for my current partner Matthew and take up with him. I buy my house and vow to live in it for at least five years. I get into BDSM and polyamory. I explore fetishes. Oh, do I explore fetishes…

Us.

Us.

This chest makes an excellent tuffet

This chest makes an excellent tuffet

Such a good feeling.

Such a good feeling.

2009: I hone my sex working skills and become a sex surrogate. I love it. I have my first MFM. I love it x2!

2010: I get fired from my job for having a sex blog. It’s the last time I am successfully slut-shamed. The silly scandal makes national news. I come out and get featured in The Riverfront Times. My daughter gets expelled from school because of the scandal. My ex-husband sues me for full custody of my daughter. PayPal permanently bans me for having adult content. I co-found Sex Positive St. Louis. I’m really scared.

SEX+STL!

SEX+STL!

2011: I’m broke and freaking out. I feel like I’m running out of options. I’m in danger of losing my home and my daughter. I’m having death fantasies. I shave my head for a legal fundraiser publicity stunt. I host BDSM fundraisers at creepy, dirty warehouses that lack heating and cooling. It’s fun, but it still sucks. I’m invited to tell my story at ideacity, which is like a Canadian version of TED. I have a public speaking phobia, but decide to face my fear, and speak in front of an affluent audience of 700. I SUCK. The audience is not impressed. I’m mortified. To this day, I have not watched my talk.

BUSTED. Photo by Mike Estes

BUSTED. Photo by Mike Estes

ME. BALD.

ME. BALD.

2012: I’m featured in Hustler magazine. After three years of being ostracized, I finally get a day job. My ex drops the lawsuit. SUCCESS. I go to China again. It’s okay.

Hustler

Hustler

Hustler interview

Hustler interview

2013: I have a gang bang for my 40th birthday. It’s one of the best events of my life. I also go to Europe for the first time, and it’s the best trip of my life. My daughter is now a teenager! We’re very close.

All hands on slut!

All hands on slut!

2014: I go to Japan. It’s pretty awesome. I buy a new car. I go to Europe again. And again.

2015: I quit my day job to focus on sex-positive activism full-time. I go to Alaska. I host sex demos, incredible orgies and sex parties at lakeside mansions in the country. I AM QUEEN. Everything is so awesome. I’ve worked so hard to get here. I’ve overcome many fears and obstacles. I’ve turned heaps of negatives into positives. SEX+STL looks like this now – we have 3000+ members!

SEX+STL Co-Leader Team!

SEX+STL Co-Leader Team!

2016: As a single mom, I haven’t missed a single mortgage payment on my house. My goal was to live in it for five years, and this is year #8! We all take turns when it comes to life’s celebrations and tests. Speaking of, my partner Matthew turned 40, so I rinsed, recycled and repeated the gang bang gift and organized a party for him that was equally epic. I posted all the glorious details here! I’m doing well, thanks to hard work and a strong support system, but a lot of my loved ones are experiencing death and loss. It’s a rough year for many, so I try and help as many people as I can while I’m strong and able. I don’t forget that I received help when I needed it, so I’m paying that forward.

2017: Made another big dream come true – went to Iceland! Was hoping to see Northern Lights, but our timing was off by a day! They had a spectacular sky show on New Year’s Eve, and we arrived on Jan 2!

The Arch in Iceland. It was very grey and rainy.

Bought a grandfather clock as an impulse purchase. Attended my first AA meeting – WOWOW – still processing…

Time is valuable.

SO! What’s next? How many years do I have left? What will I accomplish before I die? I have lots of dreams and goals, and I intend to make them ALL come true.

If you want to follow my lead, I recommend many great resources, including the books The Power of Now and You are a Badass.

Stay tuned for more updates!!!

Comments

fuzzilla 2015-07-14 13:47:49

What an adventure!

You look like Laura Palmer (Twin Peaks) in the pic between ’92 and ’93.

Reply

Sandy 2015-07-14 23:54:40

Wow, you have more than enough material for a book and a movie. In fact, one woman wrote a whole book about just one thing you did in 1989, sex every day for a year: “365 Nights: A Memoir of Intimacy” by Charla Muller, Betsy Thorpe, 2008. Have you written about that experience? Did it improve things, or become a chore? Of those of us who wouldn’t mind doing that, we’re not likely to have a spouse who would agree to it, much less follow through.

Reply

    Kendra Holliday 2015-07-15 05:04:44

    I was just a teenager when we did it, so it was easy, a sport, a fun challenge. I remember the days when I would have school until 3pm and then have to work from 4-10pm, so we only had about 20 minutes to squeeze it in on those days!

    Reply

Kendra Holliday 2015-07-15 05:11:11

This was such an interesting exercise! YOU should try it – I sit back and think about all the phases and trials I’ve been through. PHEW!

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angela 2015-07-19 04:30:52

wait – you had sex every day for a year, and your first orgasm was after that??!!

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    Kendra Holliday 2015-07-19 05:49:17

    Yep! I wasn’t taught by myself or others about pleasure and being in tune with my body and finding out what felt good for me – I just jumped right into pleasing others and scoring. I would say in my early days, I had sex for the wrong reasons. It was still fun, exhilarating, etc, but I often used it for attention, to rebel, to show off, even for revenge.

    There’s a book on my shelf I’ve been meaning to read – it lists all the reasons women have sex.
    http://www.amazon.com/Why-Women-Have-Sex-Everything/dp/0312662653

    Reply

Joan Price 2015-07-20 11:56:03

Wow, Kendra. I knew some of your story, but far from all of it. I am so impressed with you, dear woman, for emerging into the strong, beautiful, proud woman I know you to be. Thank you for the inspiring message that accompanies your story: we are resilient, we are strong, we can overcome, we can bloom.

So glad I know you!

— Joan

Reply

    Kendra Holliday 2015-07-20 12:33:40

    Thank you soo much! I feel the same way – fortunate to know a strong, talented woman who has shaped her life to be a beautiful and rich one!

    Reply

Mikkel 2015-08-21 03:41:34

There are many things that are attracting with you. By far on top of my list is you natural courage in life. Keep building your happiness! Greetings from north of the polar circle, in Sweden

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Rich 2016-09-24 00:12:32

Great. Story and so glad it has eventually become a happy one! I hope that it continues to be a great adventure.

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Stephen 2016-09-24 07:46:14

I wish this could be spread to everyone everywhere, especially troubled youth who can’t comprehend the “It Gets Better” thing.

I’m actually a proponent for suicide in certain situations, but NEVER for those in their youth. Your childhood and life situations would easily have “justified” a suicide, but then you’d have missed what you have become. Not only do you have life by the balls (pun intended), but you have experienced levels of happiness others can’t possibly comprehend, because you have been on the complete other end of the spectrum.

And now you’re still a fairly young advocate, leading the way for others in need, and most importantly setting a great example for your own child. You have doggedly made sure she wasn’t going to see half the hell you did, and for that you’re to be commended beyond belief.

The past can’t be completely buried, for sure, and I’m positive you have crazy deep dark times once in awhile, but you’ve somehow managed to cope, to learn it’s better on the other side, and to continue to blog and inspire us all.

I couldn’t be prouder of you and I’m so happy I found this page oh-so-many years ago. I can’t tell you how much your honest, open writings have helped me therapeutically.

THANK YOU!

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Algernon 2016-09-24 11:18:08

Amazing!

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Rhett 2016-09-25 14:48:58

Kendra- I’ve enjoyed your The Beautiful Kind for the past few years and have really come to admire you. This post multiplies my admiration tenfold. We are all a sum of our experiences and the challenges we have overcome. It took a lot of courage to share your milestones. You are an incredibly beautiful lady but, equally important, you are a beautiful and strong soul. The world is blessed and graced by your presence in it.

Reply

    Kendra Holliday 2016-09-26 09:31:06

    Awww thank you so much! I really appreciate you sticking with me all these years, through good and bad. 🙂

    Reply

Stephen 2016-09-26 04:42:25

How did you pull this off so well??

I decided to try it and I’m at 2000 words and only at age 16. Jeepers.

Reply

    Kendra Holliday 2016-09-26 09:30:32

    WHOA! Mine is at a respectable 1709 words. 🙂 Isn’t it a good exercise? Helps to put things in perspective.

    Reply

Natalie 2016-09-30 21:21:26

Your authenticity and vulnerability are inspiring. Big love from Saskatchewan, Canada <3

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Dan 2016-10-02 16:08:31

You continue to be my brave hero, Kendra!

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Claudia 2016-10-23 17:00:13

Kendra, your story always inspires me, and your bravery and courage are a huge motivator. While I would not go to the extremes you do, I am a big believer in supporting the journey of everyone,especially you, as long as kids aren’t involved, and adults are consenting. Keep on staying strong! 🙂

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Dragonhide 2016-10-29 09:07:26

I greatly admire you.. Always have. After all this experience you still shine brightly. Thank you for your friendship! X0x0x

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Dragonhide 2016-10-29 09:09:39

And it’s quite a giddy moment to see you list your 40th birthday as one of the best event in your life.. <3

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Rex Jones 2016-11-10 12:10:45

Wow, great timeline and very well written. For a woman to have been through what you have and be so positive and using those experiences even the bad ones, as positives rather than negatives is inspiring. It cracks me up when girls graduate college and they think they’ve had “experiences” and are ready for life. They have/had nothing on you when you were that age. One thing I wished you would have mentioned was the year and reason(s) you first grew out your armpit hair. I think it’s awesome that you keep your amazing body natural and don’t alter it in any way thru breast implants or shaving everything below the eyebrows. Many females are giving up armpit/leg/pubic hair removal and it is lovely to see, glad enlightened women like you are leading the way.

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AlanK 2017-05-06 08:23:10

Marvelous story. By keeping each episode so brief you hit harder. I know we keep nagging you but you need to find an editor and write your book.

All that horrible stuff (plus of course the good stuff) helped make you who you are. If you could trade in ALL of it for a boring-but-safe first 30 middle class years would you?

Reply

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TBK365

Agreed! They know SO much about me, & I know 2 sentences about them. https://t.co/Yphrn8bHpA

TBK365

The cock n' ball torture demo was way bloodier than I expected. It was great watching a sadist giggle & masochist swoon with pain/pleasure.

TBK365

Proud that I pulled off 3 events this past week - whore hangout, burn your past, and cock n' ball torture demo. That last one was intense!

TBK365

Very forgetful.