The Three Times I Screamed

By Kendra Holliday | March 1, 2021

Ed Note: This post details my personal experiences with sexual trauma.

I’ve been with hundreds, if not thousands, of sexual partners. Some have been AMAZING, and most have been good. A few have been BAD, and a few have been ugly.

To be clear, I’m an experienced professional, and based on what my partner is seeking, I try my best to deliver. Some men want an entertaining diversion, a frolicsome romp into the realm of female energy. Some men want to learn how to be good lovers. Some men want validation and healing.

I usually use a soft, sexy voice to instruct and redirect: “Gentle, please. Oh yes, I like that.” Sometimes, I choose to endure irritating groping, or I’ll grimace my way through a dry fingerbanging, the man treating my vagina like a chainsaw he’s priming. Occasionally, I’ll exclaim “ouch!” or a stern “No!” if, for instance, he’s trying to stick it in without a condom, but for the most part, I don’t want to spoil the moment or damage his confidence.

All that said, here are three times I straight up screamed during sexy time:

A little takedown scene. Photo by Mike Estes

1. Years ago, I was on a date with a man. He was going down on me. I was lying there, relaxed and feeling good, when all of a sudden, he bit down hard on my clit!

I screamed! WTF?!

I gasped, “Why did you do that?!”

He replied, “The last woman I was with liked when I did that.”

Are there any women reading this who like having their clit chomped on? I’m sure some do, but most DO NOT. Always err on the side of caution when experimenting with sensation. Ask for preferences. Go slow. Start with less pressure or sensation and watch for body language and feedback.

I never went near this man again. I associated him with distrust and pain.

2. In 2018, I was going through a rough time, so I was distracted and my defenses were down. I agreed to let a young man from Indiana visit me for a session. I had screened him with a phone call, and he had given off some weird vibes. Normally, I never agree to be intimate with someone sight unseen, but like I said, I was in a bad place and grieving a loss, so I gave less fucks.

As the man drove hours to St Louis, I felt mounting dread. I had asked him what he was into, and he replied ominously, “You’ll know when I get there.”

I was so nervous by the time he knocked on my door. I took a deep breath, and opened the door.

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Why Creative Sex is Better Than Straight Sex

By Kendra Holliday | February 18, 2021

Let me school you on creative sex…

Years ago, I went to a swinger party with an ex. There were six women at the party, and we all had lots of fun. But, to my surprise, when we were driving home, my ex lamented, “I only got to be with four of the women there.”

Huh??

That’s right – he was dissatisfied with only getting to stick his penis in four of the women’s vaginas that night. He was keeping score!

I’ve noticed other times where I’ve played with a man, and we’ve gotten naked, shared pleasure, had oral, but he left disappointed because he didn’t get to do ALL THE THINGS, i.e., stick his penis in my vagina and have intercourse.

I have clients who spend time with me, and instead of basking in female energy and pleasure, they get bummed if they don’t have an encounter that involves them having an 8 inch penis that remains hard for 45 minutes and drilling me bareback in four different positions.

In other words, they feel let down that they aren’t having sex like they see in mainstream porn.

Meanwhile, I’m having amazing, abundant sex with my partner of 12 years that is leaving us both extremely happy and fulfilled.

The Key to Good Sex!

You want to know why?

Because we are having CREATIVE SEX. We aren’t having straight sex!

Straight sex is what you see in mainstream porn. It is male centered. It’s penis focused. It’s vigorous and aggressive. It’s filmed for camera angles, and based around the male orgasm. It’s objectifying. It’s GOAL ORIENTED, which can set the stage for unrealistic expectations and A LOT of anxiety. And anxiety is terrible for arousal!

The women in straight porn are often uncomfortable – from the fake eyelashes and bleached hair and garter belts and heels, to the pussy pounding and loud vocalization and money shot in the eye.

Creative sex, on the other hand, is more about pleasure, skinship, being in the moment. It is about savoring the experience.

Straight men crave intimacy and connection, but they seek it out in a rigid way that can set them up for disappointment and failure. Moreover, it can be off putting or dissatisfying to their partners.

Creative sex is more egalitarian, and allows for more pleasure and orgasms for all parties involved.

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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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I Met Larry Flynt!

By Kendra Holliday | February 10, 2021

Larry Flynt and me! photo by Mike Estes

Ed Note: This was originally published June 29, 2012. Larry Flynt died today, Feb 10, 2021. What a legend. 🙁

Earlier this year, I was featured in Hustler magazine.

Hustler Hollywood store threw a party to celebrate, which was a lot of fun.

But that was NOTHING compared to what happened this week! Larry Flynt visited St. Louis and I got to meet him!

I asked one of my girlfriends to go with me. “You want to be seen with a hot chick, don’t you?” she commented drily. Well, yeah!!!

With her white power suit and mirror shades, she looked like my bodyguard – a super sexy Charlie’s Angels type bodyguard.

We walked up to the store and were greeted by a bearded man handing out postcards. Upon first glance, the slick marketing material looked like it was made by Hustler, but upon closer inspection, it proved to be anti-porn literature!

Every year millions of men and women become addicted to porn. Millions let their lust control them. ‘Lust’ is having sexual or pornographic thoughts about another person.

In the book of Matthew, Jesus says if you LOOK at a woman with LUST you’ve already committed Adultery in your heart.

In the book of James, the Bible says that if you break only one commandment, you’re guilty of ALL of them. Breaking God’s law is called sin. Sin leads to death…

So clever of them to try and make people feel guilty for coming to an adult toy store.

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Crystal Delights Ceramic Dildo

By Kendra Holliday | February 5, 2021

Crystal Delights Ceramic Crystal dildo

Ooh, la, la.

Check out this Crystal Delights natural sex toys ceramic dildo.

All Crystal Delights sex toys are made from natural materials that are 100% body friendly and body safe. Materials that are free of Phthalates, latex and any other nasties often linked to sex toys.

As a company that is ecologically friendly and environmentally aware, Crystal Delights are committed to providing you with the highest quality natural sex toys, handmade from mother nature’s finest materials in ways that are kind and loving towards your body and the earth.

Each toy is hand crafted by highly skilled artisans who have helped design sex toys that look just as great as they feel. Every toy has its own Swarovski crystal embedded within it – which means that no two toys are exactly the same. Each one is as unique and individual as you are.

I used my gorgeous dildo for the very first time during a hot threesome.

I was with Matthew and dayglow. He had us lie back and pleasure ourselves as he stood over us, gazing at us with lustful appreciation, stroking his dick.

dayglow is tall and thin, with many gorgeous tattoos and a pierced pussy. Her thatch of pubic hair is natural blond. She used her silicone vibrator.

I was SO excited to debut the ceramic dildo. What does it remind you of? It’s one of the most artistic toys I own – I LOVE the colors. It looks like a mysterious relic, nothing like the pictures I saw when I chose it – they really are all one-of-a-kind. I can’t even tell you what color the Swarovski crystal is – it winks and glitters like a peacock, a fortune teller, a beautiful dream.

I wondered about the honey dipper head – would it be big enough? I was delighted to discover that it worked perfectly with my g-spot, the ridges were delicious! It makes a great tool if squirting is your objective. The flared base made for easy handling, too.

I was glad when Matthew took over and fucked us both with our toys at the same time – it made it much easier to lie back and bask in the sensations, except I kept craning my neck looking to see him manipulate her pussy with his hairy, highly skilled hand. I love watching live porn!

Properly primed, we put aside the toys – I carefully placed the ceramic dildo on the dresser, to be washed later and put back in its silk-lined, padded protective pouch.

And then we fell into this perfect scenario where dayglow and I pretended to be sister wives worshiping our Master. It was all about all of us – loving, erotic, nasty, and oh, so good.

You can get your own crystal accented, work-of-art natural sex toy here.

But if you’re in the market for a threesome, you’re on your own.

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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My Top Sex-Positive Recommendations

By Kendra Holliday | January 10, 2021

Kendra Holliday will help you work the kinks out!

I offer sex and relationship consulting, and I’m happy to say that I’ve been getting more women, LGBT folks, and couples these days. Historically, most of the people who have sought me out for my unique services have been men who crave female energy.

The Top 5 reasons why people contact me are, in this order:

1. He’s a married man in his 50’s or 60’s whose wife is not interested in sex (mismatched libido)

2. He/she/they have some sort of sexual issue they want to work through, such as inexperience, adult virginity, anxiety, or orgasm/penis problems (Erectile Dysfunction is a common complaint – it can get complex when you heap social conditioning and anxiety on top of the natural aging process.)

3. He/she/they are interested in branching out sexually, either because they are in transition, in between relationships, not getting laid, or curious about alternative lifestyle options (non-monogamy, BDSM, sex work, etc.)

4. He has a fetish and is ashamed/seeking an outlet

5. They want to meet me, and possibly rub me for good luck

———

My goal is to offer tools, connections, and non-traditional options so that the people seeking me out can reach their goal of becoming happier and healthier. My approach is unconventional, and I get referrals from licensed sex therapists. I’m pretty well connected and have a strong network. Sex is my specialty, which ties into work, family, personal – everything!

Here is a list of resources I most often recommend to my clients:

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A Polyamorous Formula That Works

By Kendra Holliday | January 5, 2021

I love to explore.

I love to explore.

(For some background on polyamory, please read my article Love Like An Ocean: Diving Deep Into Polyamory.)

My partner and I have been together for twelve years.

We first met July 2007, at a friend’s wedding. We are in a long-term, committed open relationship. We started our relationship open. We don’t live together – we keep our families, homes, and finances separate. We see each other about 2 or 3 times a week. We are open to countless possibilities when it comes to sharing intimacy with other people. We deeply enjoy and appreciate our non-traditional relationship.

But it certainly isn’t a reckless free-for-all. In order to keep it healthy and drama-free, we constantly communicate with each other to ensure ways we can exercise our freedom while operating on mutual respect.

Outlined below is an arrangement that works for us.

It can be difficult balancing everything, but this is how we prioritize:

1. Kids/family

2. Careers

3. Our relationship

4. The people we are dating/close relationships

5. Social/volunteer/misc.

Sometimes we will date a person or couple once or twice, or just for a weekend when they come visit. Sometimes we will date a person or couple for a few months or longer. Usually lives change and shift so much that we ebb and flow into things naturally. It feels very fluid. We can date other people solo, or together.

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End of 2020 Reflections

By Kendra Holliday | December 25, 2020

Click to enlarge

If there is one word that summarizes this year for me, it would be “disrupted.”

As of March 2020, everything broke apart and turned upside down.

In normal years, I offer consultations and intimacy sessions, host play parties, and am co-leader for Sex Positive St. Louis, a not-for-profit org that was founded in 2010.

I listened to a podcast where they talked about “All That 2020 Has Taken From Us.”

Here’s my list, what’s yours?

Things 2020 Took From Me:

Gather around for a sex-positive storytime!

80% of my income (thank goodness for a few good men who have kept safely in touch this year)

My 20 year old cat – he died of a sudden brain tumor in Feb.

Sex Positive St Louis events – our annual clothing optional spring fling, our naked pool party, Fleshtivus, our 10 year anniversary celebration.

My birthday trip.

Our summer vacation.

My 19 year old cat – she died of mouth cancer last month.

My childhood home – I helped my dad move into an assisted living apartment and sell his home. We got rid of almost everything.

Most of my dad’s brain – his dementia has gotten so much worse the past few weeks.

My mental health – I’ve had a few breakdowns and bad days, but I’m feeling okay right now. Going to revisit my Sanity Plan next week!

The most frustrating thing I’ve had to deal with this year is impatient men who push my boundaries. They contact me, I state my protocol, and they immediately start to push my boundaries, whining about masks, trying to get as much of my time, energy and expertise as they can for as cheap as possible.

It’s a constant cycle of eager acolytes who contact me – I try to teach them how to light the candles, and they want to just rush in and burn down the church. It feels so disrespectful and is exhausting.

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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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“I Want to Please You”

By Kendra Holliday | December 4, 2020

Pay attention.

So many men are sick from toxic masculinity in our society. They have to be very manly, which involves taking care of business, being in charge, hiding feelings, and burying their feminine side.

Yet, they crave a place where they can surrender to a strong, sexually confident woman and be awash in female energy and power exchange. They want to be cared for. They want youthful female energy. They want mature female energy.

So they contact me requesting help with exploring their sexuality, but then proceed to railroad me and call the porn shots and trample all over the sensual process and fuck it up. So frustrating!

Here’s a Dan Savage podcast where a man wants to know how to get his vanilla wife to like domming and pegging him. Go to the 8:35 mark and listen.

Ready to party!

Dan points out that for some women, this can feel more like work than fun, so he suggests backing things up. For a woman not used to being sexually dominant, a good place for her to start is to think about what she wants right now and demanding it.

But what if what she wants right now is a cup of tea? Will that disappoint her partner? Will taking small steps like this lead them to a place where they both feel fulfillment?

I get a lot of men who tell me, “I want to please you.”

But then, when I tell them what I want, they steer things back to what THEY have in mind.

If you want me to peg you, piss on you, sit on your face, objectify you, humiliate you, rub your naked body while you talk on the phone, that’s totally fine! You’re hiring me to perform a service, and I am happy to oblige. I have so much fun being creative sexually! I like taking care of you.

But don’t get it twisted. Are you doing this for you, or are you doing this for me?

Prepping for a session takes work, so not only are you paying for the time we are mentally and physically engaged, but you are paying for the hour before and after. I have to dress up in uncomfortable lingerie and heels and get into the right head space. I have to clean up afterward.

If you REALLY want to please me, here are some ideas:

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What Does Being Penetrated Vaginally Feel Like?

By Kendra Holliday | November 19, 2020

HOLY SHIT YES

HOLY SHIT YES

Let’s get this cleared up right off the bat: Do you wanna know what it feels like to be penetrated non-consensually?

LIKE YOUR SOUL IS DYING.

So don’t do that. DON’T penetrate other people non-consensually. I can’t believe I have to state the obvious. COME ON, PEOPLE.

Now, let’s move on to how it feels to be vaginally penetrated when you are into it, turned on, etc.

I posed the question on fb and twitter, and got responses from several curious men, but only one from a woman! My friend, Bianca:

“Being penetrated vaginally feels like a void is being filled. Like the right jigsaw piece is in place. Like warm candy. So good you roll your eyes up with pleasure.”

YESSSS.

Let me elaborate.

It’s like tucking into this gooey, decadent, absolutely delicious dessert, all sweet and salty and creamy.

It’s like you have a throbbing headache, and someone slips you morphine. Hot, throbbing morphine, for your hot, aching pussy.

It feels like a drug that will save your life.

It feels completely base and primal, like you want to fuck the earth and fill your womb.

It feels the way a spring crop looks, all those new green shoots pushing up through the moist, fertile black soil.

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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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