Category Archives: Health

Happy Fisting Day!

By Kendra Holliday | October 21, 2021

I caught this exchange on a sex blog the other day:

“Is fisting painful?”

The sex blogger replied:

Two insidious suppositions haunt any discussion of fisting. First, that it will stretch out the vagina to cavern-like dimensions; and second, that it will hurt. Neither is true…

Remove the fist and the vagina does not hang open like the lips of a mouth-breather. It snaps back. Really. Maybe I should post some before and after photos some day?

In the comments, I volunteered to do an explicit photo series, because that’s what occurs to me when I catch wind of something sexually daring, unlike most people who read about it, nod with curiosity, and then go on about their business.

I enlisted my dear friend Rockabilly Girl to do the fisting, and Matthew to take pics.

Get this: I was featured in Hustler magazine earlier this year, and they asked if they could run this photo series. At first I was shocked at the idea, but then I decided it would be pretty fucking cool to rock the fisting in a national hardcore porn mag!

So they made everyone sign releases and submit photo ID’s, including Rockabilly Girl, whose fist is the only thing you see in the pics (until it goes in my vagina).

Then, after weeks of legal paperwork and emails back and forth, Hustler decided against running the pics after all. Too edgy.

But not for me! I think it’s natural, lovely, and intensely beautiful.

So here you go.

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Prostate Mama

By Kendra Holliday | October 17, 2021

I love giving prostate massages.

Setting the stage for prostate massage

I’ve done it many times, on my massage table, and on my bed.

Sometimes, the client requests it; sometimes, I suggest it.

It’s good for your health. It’s intense. It often elicits a different kind of release/orgasm.

For some, it can feel extremely pleasurable; for others, it can be more like a soul reboot.

The client arrives clean, meaning they have prepped for anal play by having an enema or emptying bowels. I always check on them when they show up, asking how they are feeling physically, and if they’re still in the mood/headspace for anal play. If they aren’t, we switch gears. If they are, we assume the position!

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Toxic Masculinity from a Sex Worker Perspective

By Kendra Holliday | August 3, 2021

Trust me, I’m a wise witch!

I’m going to preface this with the following disclaimer: I’m a witchy, woo woo, sex worker goddess, and this brain dump is going to sound crazy. I’m fine with that, as I fully embrace my hormonal mood swings and non-traditional way of thinking. I live in a society with lots of self-imposed cages, and my motto is “Think outside the cage.”

So, hear me out, let it all sink in, and let me know what you think!

Toxic masculinity goes hand in hand with white supremacy, and it’s making me sick. It’s making A LOT of us sick.

I’ve been diving deep into history, addiction, psychology, science, and more, and I’ve connected some dots.

Centuries ago, people from Europe set out and explored the world. They invaded many areas and took them over. They brought disease, death, and disruption to the people already living there.

They set up elaborate exports and imports of toxic trade – sugar, tobacco, alcohol, and slavery. They brought oppressive religions and destructive concepts that were deadly and divisive.

They declared that people, plants, animals, and places were all possessions. They put up fences, walls, and demanded territorialism.

They sought to control everything, and lived with a scarcity mindset. They instilled and lived in fear. They were hungry for power imbalance. They felt they were anointed by God, and thus justified in all their actions.

These things represent male energy: fire, cars, guns, alcohol, nicotine, conquering, destruction.

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My Solo Tantra Awakening Ritual

By Kendra Holliday | February 13, 2021

Sacred stones and yoni eggs

Sacred stones and yoni eggs

Ed Note: I wrote this post a few years ago, but it’s more important than ever!

Since I’ve been back from Tantra Training, I’ve practiced the Tantra Awakening Ritual with several of my friends and clients.

But get this – you can also perform the ritual solo!

To learn how, you can read Barbara Carrellas’s book Urban Tantra: Sacred Sex for the Twenty-first Century.

It’s actually super easy to do, but it helps to be coached through it your first time. I read Barbara’s book thrice before I went to her workshop, and it was only there that I was able to “get it,” with her walking me through it.

UPDATE: Now you can DOWNLOAD her 30 minute guided meditation here. Best $15 I’ve ever spent!

Tantra is like the City Museum in St Louis or House on the Rock in Wisconsin, or many other exotic and unique places in the world – it’s hard to explain it, you just have to experience it for yourself. And you can experience it WHENEVER YOU WANT, FOR FREE.

Tantra is about weaving and building energy, being present, and opening yourself up to a deeper level of consciousness.

Awakening is rousing, getting in touch with parts of yourself you have buried or ignored. This can be spiritual, mental, or physical. So often we feel disconnected from our bodies, we’re so in our head thinking and worrying so much. REPLACE THE FEAR WITH LOVE.

Rituals are tools that help us focus our attention.

The first time I did the solo ritual, I was in a roomful of people, which might sound like an oxymoron, but we weren’t interacting physically with each other. We all lay supine on the floor separately, and Barbara encouraged us to breathe deeply, go with the flow, and make noise if we wanted to. Having other people’s energy present made it more intense – I heard heavy breathing, crying out, moaning, sobbing… I myself felt great tingling and waves of emotions, and then cried cathartic tears afterward.

Naturally, I wanted to try it at home by myself. Ideally, I’d like to schedule this self-care weekly. You can knock it out in 30 minutes, or you can turn it into a more elaborate ritual.

For my first solo ritual at home, I chose a planets and elements theme.

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Premature Ejaculation: Not So Fast

By Kendra Holliday | January 28, 2021

Note: This article was originally published here.

Gotta learn how to control your super powers

Did you know that the average woman takes about 20 minutes to achieve orgasm? The majority of men, on the other hand, don’t have a problem coming in 5 minutes. If a woman can orgasm during intercourse (though not all do), she’s going to require more time than most men need. Basically, a woman’s orgasm is like a symphony, whereas a man’s is more like a rock song.

In general, men can stave off the inevitable for the sake of his partner, employing techniques akin to swinging a guitar solo or engaging his audience. Some men, however, have trouble lasting even five minutes—it’s more like a radio jingle—and they’re anxious to build up their longevity so they can properly satisfy their partner. Plus, radio jingles are annoying.

There’s an interesting phenomenon called The Coolidge Effect, which got its name from President Calvin and Mrs. Coolidge. Seems the First Couple was visiting a farm, and Mrs. Coolidge remarked that she wished the Commander in Chief were as randy as a rooster they saw strutting around. President Coolidge retorted, “Well it’s no wonder I’m not as frisky; I’ve only got one hen in my henhouse.” The Coolidge Effect is when a man become bored with his regular sex partner, but gets “over enthusiastic” (comes in a flash) when introduced to new ones.

Case in point: as a sex surrogate, I worked with a 45-year-old attorney who said he’d could go a decent amount of time during intercourse with his wife of ten years, but now that he was divorced and dating, anytime he got with someone new, he had trouble lasting more than a couple minutes, leaving him baffled and frustrated.

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Breathe Easy

By Kendra Holliday | January 26, 2021

Ed Note: From the archives. I look forward to working with clients again in a more normal way later this year!

Kyle took the train from Chicago.

All day he traveled, portable oxygen tank in tow.

He didn’t listen to podcasts or music. His mind was too occupied with thoughts of what was to come –

me.

Sexy bitch in burgundy!

Sexy bitch in burgundy!

You see, Kyle was overcoming great obstacles in order to find answers and rediscover intimacy with another person through surrogate sessions with me. It had been seven years since he was last with a partner, and he was missing human touch terribly.

Why? Life took an unexpected turn from him.

I’m always fascinated by my client’s life stories, and his was especially interesting.

As a forensic anthropologist, Kyle traveled the world working on ancient civilizations and gravesites. He was fit, had a passport, and worked outdoors a lot, in all kinds of conditions. Destinations included South America, Australia. He was next scheduled for a project in Europe, and had his sights set on Asia.

Then one day, at a church in Mexico, disaster struck – literally. The team was digging in trenches, excavating an old sacred graveyard for relocation. Despite wearing a Hazmat suit and respirator, something went wrong when a 400 yr-old-bone was hit with a pickax. Bacteria exploded in the air, and invaded his lungs. He suffered serious pulmonary damage, and has been on oxygen 24/7 ever since.

A couple years after that, he was hit in the ass with colon cancer, and had to undergo risky surgery to remove 1/3 of his colon. The doctors warned him he might not survive the operation, due to his lung condition. They had to give him an epidural and twilight meds instead of general anesthesia!

Incredibly, he survived this double whammy.

Nowadays, Kyle is the same age as me (43) and lives with his parents on disability. He can no longer drive. He’s overweight and in poor health. His lifestyle went from adventurous globetrotting to being tethered to a tank in his bedroom, more or less homebound, living vicariously through the internet. He is an odd combination of extremely worldly and intelligent, and emotionally stunted and childlike.

We had our initial consult over Skype. I found out he’s quite kinky like me – into stockings, men and women, incest and rape fantasies, pegging… all that fun stuff! His sensitivity and shyness put me at ease, and we clicked.

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Can Women Get Ruined From Too Much Sex?

By Kendra Holliday | January 17, 2021

Dear Kendra,

A recent tweet of yours got me thinking. Someone asked about the number of sex partners and someone answered, “Why does it matter?”

Well, the average guy like myself, ignorant to the female body, thinks men can have sex with a thousand females and have no physical change to the penis, but if a woman has sex with a bunch of partners, her vagina becomes stretched out or damaged in some way.

As I get older and wiser, this seems like a really stupid believe. Can women have sex with many partners without physical change? Could you explain how the female body really works and educate us cavemen?

My reply:

Sexy hipsters

Sexy hipsters

Every body is different, so some women have very tight vaginas to begin with that slowly become looser over time, kids or no kids, sex partners or not.

How many kids you have makes a difference. So can how much you use your vagina. OR it makes no difference! What if she has c-sections, for instance?

What if she fucks guys with HUGE dicks?

What if she’s a porn star? I’ve heard of porn stars doing anal scenes for five years who sustain damage. Then there is Belladonna who takes really good care of her body and exercises muscles most of us aren’t even aware of!

A woman can do Kegel exercises and tighten PC muscles and make things better.

I’ve asked several guys how different pussies compare – guys who have been with total sluts, women who have had NO kids or four kids, and they say it all feels the same. I think that is their honest answer.

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Size Matters – In Your Head

By Kendra Holliday | December 19, 2020

Note: This article was originally published here.

What’s in your pants? Can’t wait to find out!

I don’t know about you, but I love surprises.

You never can tell what a man’s penis is going to be like just by looking at him. I’ve hooked up with a 6’4” guy with huge hands and feet, only to discover he has an average size penis. I’ve been shocked to find out the 5’7” Asian man with delicate features is a show-er, not a grow-er.

The other day I met with a new client, an attractive, fit 34-year-old. Usually, I get a clue what’s on a client’s mind prior to meeting him, but in this case I had no idea what his issue was. This appealed to me. I was going to get a surprise.

The Long and the Short of It

We met at a coffee shop, and took a walk in the park. Settling down on a bench, he took a deep breath and nervously admitted that he felt his penis was too small. When I asked him why, he cited two main reasons:

1. A girlfriend in high school drunkenly mocked him, telling him he had a little dick.
2. His current girlfriend cheated on him with another man.

When he asked her if the other man had a bigger penis, she’d told him yes. As horrifying as this was for him to hear, he confessed that ever since then, he has enjoyed fucking her with a large dildo and imagining he is watching a well-endowed man pleasure her as he feels he cannot.

He told me he avoids being around other men in the locker room obsessively, and that he was finding himself getting more and more into a fetish called SPH, or small penis humiliation.

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What Happens to Sex When Your Partner is Ill?

By Kendra Holliday | November 11, 2020

Ivanyi, Lovers, 1909

Ivanyi, Lovers, 1909

In the past three weeks, I’ve had three men approach me for a consultation about a problem they’ve been dealing with for longer than I can fathom: their wife is chronically ill, and they haven’t had sex in years. They’ve cared for her, support and love her, would never leave her, but they are frustrated. Drained.  They aren’t getting their needs met. They feel guilty. When I ask if they feel resentful, they immediately say no, but…

What should they do?

What would YOU do?

Are you partnered with someone who is ill?

Are you ill and partnered?

Are you getting your physical and emotional needs met?

Is your partner getting their physical and emotional needs met?

Are you monogamous or polyamorous?

How do you cope?

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My Body Modifications

By Kendra Holliday | September 16, 2020

Me in 3rd grade

Me in 3rd grade

This is a picture of me from the 3rd grade. Looking at it, it’s hard to believe I was molested – I mean, wouldn’t those ginormous nerd goggles be repellent enough, not to mention the shitty haircut and goofy fashion?

Then again, my opportunistic molester was pretty homely too, and wasn’t very picky. I daresay he had bad taste in children.

But this ugly child grew up to be a gorgeous goddess. Here are some steps I took in my maturity makeover:

Braces – My parents could only afford braces for one of their five kids, so they chose my sister. That means I made it to adulthood with one of my front teeth jutting out. In grade school, kids would come up to me all the time and inform me, “You have a crooked tooth.” LIKE I DIDN’T KNOW. I was self-conscious about smiling, so I scowled a lot.

Finally, when I was married and DINK (double income, no kids), I took the plunge and got Invisalign braces. I’M SO GLAD I DID IT. It was worth every penny (how many pennies are in $4000? oh never mind). Now I wear a retainer at night whenever I feel like it, which is about half the time. I’ve only broken it once. Flossing is so much easier.

Heart zapped – In 2000 I birthed my daughter vaginally – hooray! I didn’t want an epidural or a c-section, but I sure did freak out and request the epidural as soon as my labor pains kicked in for real.

My doctor took it upon herself to give me an episiotomy (a surgical cut in the muscular area between the vagina and the anus), which took a long time to heal. But further north, the pregnancy took other tolls on my body – my heart.

It had trouble keeping up with the extra blood flow and work involved with carrying another person around inside me for months, so it started to misfire. I developed SVT – Supraventricular tachycardia. My heart would sometimes race 300 beats a minute, which was inconvenient and scary. The solution was a procedure where they snake a laser up through your groin to your heart and zap the naughty part and kill it. So my heart has a scar.

The procedure cured my condition, but that zap also signaled the end of my marriage. I woke up from the procedure and everything changed in my life. My heart was fixed and broken, all at once.

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A Tale of Two Clients

By Kendra Holliday | August 1, 2020

Wear a mask!

I have two clients who have been wanting to see me for intimacy sessions since March. I told both of them that I would consider doing a masked session with them. Both are very nice, intelligent people.

Client #1 is a 32 yr old tradesman. I met him earlier this year. His response to my proposal is as follows:

“I’m personally not a fan of wearing masks so I’ll just wait until things get a little closer to normal or whenever you’re comfortable setting something up. 🙂

I would just like to throw out there that I don’t think not wearing a mask when with someone else necessarily means that someone doesn’t have good ethics.

From all the research I’ve done, I’ve concluded that wearing a mask has less than satisfactory results and that washing hands and keeping up with good hygiene practice has much more impact at keeping Covid at bay. Covid has been elevated to a sort of terrifying virus when it’s actually closer to the regular flu that happens every year with a little more power behind it.

I would have no problem being with someone who I know is practicing good self-care habits to actively prevent getting the flu and is strengthening their immune systems more than I would trust the effectiveness of a mask (which has to be a an N95 mask in order to protect against the virus particles. The Covid virus can easily slip through any other kind of cotton or fabric that’s being used as a mask.)

Just wanted to say that not all men who are choosing not to wear masks are synonymous with having low ethics. I’m trying to be as conscious and aware of the decisions I make and not just blindly follow everything the government tells me to believe about anything, including Covid.

Hopefully that comes across as sharing my perspective, as I’m not attempting to be divisive. 🙂

Client #2 is a 64 yr old scientist. I’ve been seeing him for years. He has opted for monthly phone sessions with me all this time, as opposed to seeing me in person. I showed him Client #1’s take on masks and Covid. His response is as follows:

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COVID Kendra?

By Kendra Holliday | May 19, 2020

Flirting with the Angel of Death…

Sigh…I would make the most beautiful vector. 💃😚

I’ve been keeping a list of people who have been wanting to share intimate space with me since mid-March, and it’s currently at 40 folks. These are just the ones who have been screened and verified! 😇🤓

Can you imagine if I went ahead and booked all of those sessions? Move over, Typhoid Mary – COVID Kendra would give you a run for your money! (Speaking of money, this is about ~$10,000 of income I’ve missed out on.) 💸

Typhoid Mary was famous for her peach ice cream – mine is over here melting! 🍨😝

It’s been super frustrating getting loads of inquiries from people who are seeking play parties, group sex, erotic encounters. I have to keep telling them now is not the right time to act on such fantasies.

Right now, we need to hunker down with our sexually creative and adventurous fantasies and come up with some future goals – beef up our “Fuck it List” (as opposed to Bucket List). And it pains me when someone who has been in contact with me for months or even years, emails me now, declaring that they are FINALLY ready to move forward with addressing their sexual issue. I’m sorry, but the timing is off.  It’s like being an unpaid DJ taking song requests from people wearing earplugs. And then when I offer them the option of meeting online, they inform me that they lack the funds, the privacy, etc. Stifling and frustrating for everyone involved!

My hands are tied…

I promised everyone I would get in touch with them when I’m ready to start seeing clients in person again, and gosh is that a mind-bending waiting game. The devil is in the details… 👺📝
What are the best resources for me with guidelines on how to keep my clients safe? I guess I need to research CDC guidelines for massage therapists.
For now, I’ll keep blowing you kisses from a safe distance!

You gotta blow hard

My Personal COVID-19 Statement

By Kendra Holliday | May 2, 2020

Please no cock shots

(I know, I know, I should have posted this weeks ago! You’ll see why I didn’t below…)

I sure can’t tell what’s going on out there in the world, what with all the opinions and rumors clouding the facts, but I know we’re dealing with a pandemic, and that I live in St. Louis, MO, United States.

So because I can’t really trust government officials to have the intellect and priorities necessary to keep us safe, I have to rely on my inner compass and core team of trusted advisors.

With that said, I’ve decided not to engage in intimacy sessions the month of May 2020. I hope to resume intimacy sessions in June on a limited basis, but I need to see how the next few weeks play out first.

In the meantime, I’m available for online talking consults and sessions.

Why am I taking this stance?

Because even though meeting with people one-on-one is relatively low risk, the nature of what I do is extremely high risk. I’m very good at safer sex (I get tested quarterly and have never had an STI), but this is a whole different level of STI we’re dealing with – a Socially Transmitted Infection can easily be transmitted during sexy time.

I’ve been sexually monogamous with my partner of 12 years since around March 17. I haven’t been on this level of lockdown since I was married in my 20’s – HA!

I have another partner of six years I haven’t been intimate with for weeks. I’d like to get back with him at some point, and he takes priority over clients and random strangers.

Creepy bird lady

I take my partners health seriously. I know men are at higher risk of dying from COVID-19, but I don’t know what other factors make them more vulnerable – weight, heart conditions, blood pressure, lifestyle habits, blood type, age…

My mission is to help people improve their health and happiness, and my specialty is sex, intimacy, and relationships. I take that seriously. Out of respect for you and myself, I must err on the side of caution in this time of crisis. I KNOW this sounds silly, coming from a person who has had gang bangs and hosted orgies and engaged in crazy fetish work, but what can I say? I’m an ethical slut.

In March, I was blindsided like everyone and found myself paralyzed by fear and grief.

In April, I sat around for weeks, and decided that even though I’m not making money right now (thank goodness for savings and supporters of my mission!), I still needed to do SOMETHING, so I started donating my time here and there, helping others out.

This month, I’m going to shift into a more productive gear and work on some writing projects, creating content, and hosting online events for Sex Positive St. Louis. I’m going to figure out my business model going forward – rates, services, etc.

I’m extremely fortunate that I don’t know anyone personally who has tested positive for COVID-19, including my healthcare professional friends. But many of my friends have had loved ones affected.

How about you? How have you been coping during this unprecedented (at least in the last century) time? I mean, if this goes down like the pandemic of 1918, do you suppose an even bigger spike will hit us this fall/winter? We better be prepared! Hurry up with that testing and vaccine development!

Preying on Male Insecurity

By Kendra Holliday | January 29, 2020

Have you ever visited a men’s health clinic? You know, the kind you hear advertised on the radio for men who have lost their mojo – low testosterone, erectile dysfunction, infertility, etc.

Nurse Kendra 😉

I’ve never been to one, but a lot of my clients have, and it’s crazy what they tell me!

I’m all for having options, but it seems like things can get pretty invasive, pretty quickly, and for a pretty penny! And it’s all pretty silly, in my opinion. They’ll charge a man hundreds of dollars to do “wave therapy” on his penis, which is like putting a fancy medical vibrator on his dick.

I’d say that 80% of the men who come to me with erectile dysfunction are dealing with a psychological issue, not a physical one, but these clinics are quick to prescribe pills and even injections in the penis.

Yes, these things can work, but they are expensive chemicals and you don’t want to become dependent on them. They’ll set a man up with an expensive little cock shot kit he has to carry around with him and keep refrigerated. The kit includes tiny needles and a vial of liquid you inject into the side of the penis. You want to make sure you alternate where you inject, or else you can create scar tissue and damage the penis.

I think it’s better to back up and try more natural, less invasive methods first. Of course, that requires patience and a different kind of vulnerability.

Speaking of pills, there’s a male supplement out there called “Alpha King” – can you get any more buzzword than that? And all these tricks and gimmicks use all these slick science words for marketing purposes – “our product contains significantly more bioavailable sapogenins…”

And what’s with the male clinics that boast of an all-male staff, or female staff (this urology clinic staff lineup reminds me of a Hooters harem!)? Are most of the men coming to these clinics straight, or gay, or a combination? I’m just wondering.

Do they acknowledge andropause and how aging can naturally shift a person’s sexuality, which is not a bad thing? (For more on this, I highly recommend the teachings of my mentor, Joan Price, who specializes in ageless sexuality.)

All this virility fear-mongering can be misguided and exploitative. Toxic masculinity? Why, we have a pill for that…

Anyway, here are some books I use in my sex surrogate practice – replace the fear with love!

I try to teach men how to be mindful instead of “mind-filled,” and to open themselves up to the pleasures associated with experience-based sex (as opposed to goal-based or performance-based sex.)

https://twitter.com/TBK365/status/1222445859159388160?s=20

https://twitter.com/TBK365/status/1222229959885905920?s=20

What do you think? Have you been to any of these clinics? What do you like or don’t like about them?

Things That Have Been Up My Ass

By Kendra Holliday | September 26, 2019

My butt has seen better days.

My butt has seen better days.

Stop and think – how many things have been up your butt?

I have to admit, I’m just not that into the anal. It doesn’t occur to me on a regular basis. I’m much more oral and vagina-centric. So the things that have been up my butt have been few and far between. And the experiences have been good, bad, and ugly.

Here’s a quick-n-dirty list:

– Poo. EVERYONE has had poo in their butt. I hate poo. Poo is gross. Poo stinks. I don’t like smelling it, and I sure as hell don’t want other people smelling it. I’ve been using Poo-Pourri, and it works pretty well. Not that I spray it up my butt. You’re supposed to spray it in the toilet before you have a seat.

– Pink vibrating beads. I had an AmaZing experience with these. You can read about it here.

– Flexi Felix anal beads. You can read about that cute toy here.

– Bendybeads. I wouldn’t recommend these for beginners, but they are nice and sturdy, made of safe, smooth silicone. It’s fun to slowly pull them out as you’re having an orgassssmmm….

Bendybeads

Bendybeads

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I was gonna say Casper but yes this ⬇️ https://t.co/wlKs9eh4X6

TBK365

omg she scared the 💩 out of me, ha! That’s what I get for stepping out on her 💃🏼😱😳😝 https://t.co/VCjPKoT37Y

TBK365

The movie The Notebook is the worst. Also, I match the movie. 😳🤢😬😝 https://t.co/5eJmOk1lKy

TBK365

Surprise ran into my most elusive sibling today at CVS! 🦌😮 I was buying some vitamin D. 😁 https://t.co/rUqEawwtMw