Category Archives: Fantasies

Turning Lemons into Lemonade

By Kendra Holliday | November 4, 2017

I was all set to try something new – hire a sex worker for my partner Matthew and me! I’ve been hired countless times myself, but it’s rare I’m on the other side of the equation. Bonus points: My sex worker friend is very different than me. I LOVE contrast! She’s dark, exotic, tall, leggy, busty – and lactates! Mmmm!

I sent her thoughts on what I was envisioning:

90 min session, with about 30 min just talking on the couch connecting, then going to the bedroom and undressing/kissing. You would be center of attention, sweet sensual worship vibe. I’m bi and we’re both very attracted to you. Matthew likes experiencing female energy, exploring a new body, touching and kissing, he loves oral, giving and receiving, but if you don’t want to do oral on him, that’s totally fine. I will definitely go down on him! 🙂 He would like to go down on you if that’s ok. I might sit back and watch, I get great pleasure watching. It would be super hot if he was having sex with me while kissing you. But if we all end up lying around and you being in the middle for a bit, then him being in the middle and us both kissing on him as he gets a handjob…. that is what we are thinking.

She loved the idea!

Photo by Stan Strembicki

We set a date and time. I was so excited to treat her the way I wish to be treated as a sex worker – regard her as an esteemed guest, like a queen, appreciate her rare gifts.

I prepared an envelope with cash – and a tip! – to present her when she arrived, so I wouldn’t forget at the end.

And then, 5 hours before the appointment, she canceled due to illness.

I was SOOOO bummed! Sigh. The more people involved, the harder it is to turn a fantasy into a reality.

But instead of pouting and watching a movie, I came up with Plan B. I was in the mood for something special and super hot!

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A Session With All the Bells and Whistles… and Cleanup

By Kendra Holliday | October 7, 2017

In addition to offering surrogate sessions, I also entertain fetish exploration (and anything else I feel like!)

Often, a session only involves a condom and lube. Easy cleanup!

On more rare occasions, a session involves A LOT of cleanup. HA!

This week I had one of those… messy sessions. I affectionately refer to my extreme fetish clients as “pervs” or “sluts”. At first, they feel self-conscious about it, but over time, they realize my playground for perverts is safe, and they have fun with it.

Don’t get me wrong – I looove easy sessions that involve sensuality and TLC, but the freak sessions are pretty fun. I like creative sexuality and mixing it up! When I say, “Let your freak flag fly,” I mean it!!!

Here is a (dirty) laundry list of what we did in 90 minutes:

  • Two days ago, I put him in a cock cage and sent him on his way to stew in his own juices.
  • That means he had two days of foreplay. Wearing the cock cage puts him in a completely submissive state of mind. He’s like a whimpering, horned up puppy who wants to do anything for me.
  • He arrived in his boring street clothes. I made him change into a turquoise bikini and hot pink dog collar. Cage remains on.
  • I make him lick my pussy until I cum LOUD. He’s well trained to know what I like, right down to proper tongue strokes – we’ve been seeing each other for about two years!
  • Satisfied, I pull down his bikini bottoms and slap his caged cock around. I affix a few clothes pins to his balls.
  • I bend him over the bed, condom up a vibrating dildo and fuck him with it. He whimpers and wiggles like a little bitch.
  • I take him down to the dungeon and make him my toilet. I have a brilliant contraption another client designed (he needs to market this!) It’s a commode with a cut out space for a head to fit in. It is my Throne. I place him on the concrete floor with his head in the opening. Then, I sit on the toilet seat, my powerful pussy positioned above his trapped head. I piss into his eager mouth, and he drinks my piss. Gulp. Gulp. Gulp… he will do anything for me.
  • I make him shower and mouthwash.
  • We go back to the bedroom and I FINALLY uncage him. Slowly.
  • Liberated, he springs into action and begs to fuck me. I allow him to be a man. I put a condom on his free ranging dick and he fucks me. He loves my pussy. He is swimming in subspace and female energy.
  • I stop him and insist he masturbate into the condom. I drizzle lube on him as he frantically jerks off. As I pinch his nipples and stroke his balls, I whisper filthy things in his ear that involve other men, gang bangs, dogs… he’s a cunt licker. He’s a piss drinker. He’s a cocksucker. He’s my whore. I put him on display for everyone to use however they want, like an interactive art display. I have him by the balls.
  • He’s breathing like a steam engine and has an explosive orgasm in the condom. I inform him he is now a cum licker. I carefully peel off the sopping condom and squeeze the contents into his mouth. He greedily sucks it up and down and all around. I clamp a hand over his mouth and order him to swallow. Of course he does. He will do anything for me.

Before he left, he offered me a tip, which I graciously accepted. “It’s like a cleaning bill.”

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Game of Thrones

By Kendra Holliday | July 16, 2017

Ruthless

Ruthless Mottherfucker

I wrote this post in 2013!!!

I didn’t mean to, but I got obsessed with Game of Thrones.

I try to avoid television series – they’re too much of a commitment. I hardly ever have time to sit around and watch TV – in fact, I don’t even have a TV, but I do have a laptop and a partner who likes his big TV. Also, it’s his fault I became a GoT freak – he turned me onto the show.

Here are the series I’ve tried:

1. Sex and the City – I watched all of them, and am embarrassed to admit it

2. Six Feet Under – didn’t make it to the end, bailed when the gay guy got robbed

3. Deadwood – I loved it

4. Dexter – bailed by the 3rd season or so

5. True Blood – bailed after 20 minutes, too violent

I can’t stand blood and guts, so I avoided GoT, but finally my partner convinced me to give it a try. “There are some really hot scenes,” he cajoled.

Yay for whores and brothels and group sex!

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I Can Make Your Sexy Wish Come True!

By Kendra Holliday | April 11, 2017

I’ve had this “I Dream of Jeannie” outfit for a few years.

Pretty

I got it as a hand-me-down from a fancy woman who was downsizing her closet. It wasn’t my style at all (I hardly ever wear pants anymore!), but I loved how flowy and comfy it was – all sea foam green and billowing in the breeze.

I wore it with a white shirt to a concert in Forest Park, right after I got my hysterectomy in 2012. It’s like wearing PJ’s in public.

Comfy PJs

Now that it’s spring, I got it out to wear it again, and discovered the hanger it was on gave it unsightly yellow stains, so I couldn’t even donate it. It had to be trashed.

But I believe in trashing in style! Anytime I get a run in a stocking or something gets ruined, I don’t just wad it up and pitch it. I let it go out with a BANG!

Like this.

And this.

So after teasing my partner like a matador does to a bull

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His Threesome

By Kendra Holliday | December 21, 2016

So this frisky encounter happened when I wasn’t around…. and that is totally okay! Hooray for open and honest relationships!

My partner Matthew wrote this account of a hot, hardbody blond who craved an alpha male threesome – and WENT FOR IT! (The picture posted here accurately captures her look/energy.)

——–

Hot blond

I was out of town on business eating lunch with colleagues when my phone vibrated with a text. I let the conversation change subjects before I checked it.

I opened my phone to find a picture of a woman with her hand on her pussy.

No message, just the image.

I didn’t recognize the pussy and the number didn’t register from my address book.

Manicured fingernails….beautiful, big clit….no pubic hair…..I started to weed out the possibilities.

I came to the conclusion that this is a pussy I had yet to meet face to face. After a brief bout of texting back and forth, I discovered it was our friend Sunshine.

NICE!!!!!!!

Sidenote: Kendra and I had been to dinner with Sunshine and her husband Beowulf a couple of weeks prior and had a great time. We all agreed that we should get together in private soon….

I texted her back thanking her for the picture.

She responded with: “Glad you liked it. Please feel free to reciprocate so I can fantasize about what it will be like when I finally get to suck you off.”

I sent back a message with a pic of my chest, explaining that I don’t send cock shots and she would have to wait to see it in person.

Now….I hadn’t fucked or gotten head in three days, so my tank was full and ready to explode. I had already been thinking about who I was going to call to help alleviate this pressure in my balls when I got back in town.

There were four possibilities…Sunshine’s persistence sealed the deal. The next day I was driving back and the texting commenced again. We exchanged a few provocative notes and my dick was heavy the entire ride back. I could tell she wasn’t talking shit and I knew Beowulf wasn’t a bullshitter either. This woman was hot and ready to roll. She is a real “pleaser”.

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Cabin Advent Calendar

By Kendra Holliday | November 13, 2016

THIS IS OUR NINTH YEAR AT THE CABIN!!!! HEADING THERE IN DECEMBER……….

We disappear here.

We disappear here.

I’ve had many couples ask me for the name/location of the cabin we go to. Drop me a line and I’ll hook you up! This cabin is rustic, no wifi, so it’s good to come prepared with food, drink, music speakers, ambient lighting, soft blankets and pillows – we prepare a list every year.

Cuddly like kittens!

Cuddly like kittens!

Matthew and I go to the same cabin every winter, and about two months prior, we start getting CABIN FEVER.

A couple days ago, he texted me: “I hope each morning, you’re opening the Cabin Advent Calendar in your head.”

I sure am! Do you want a peek inside? Open each little window and it will reveal:

Maker’s Mark
truck
drunk
gluttony
lust
orgasms
smoke
bourbon cake

hot tub
robes
fireplace
massage oil

Beard.

cum

country music
cabin music playlist
old traditions
new ideas
movies
Deadwood
heat
love
warmth
cock
sex-scented beard
fantasy
roleplay
escape
sleep
connection
spanking
squirm
scream
pain
tears
us
timeless

yes

yes

yes

..

.

Cabin 2015

By Kendra Holliday | November 12, 2016

This was our seventh year at the cabin! Such a magical place to reconnect!

The drive there is always fun – we stop in small towns and look for weird and new things to explore. You know, like the world’s largest rocking chair.

One outpost has moonshine tastings – 12 different kinds! We got apple pie and egg nog flavor, which is amazing in root beer.

Cuba, MO has an Amish store where we bought the most amazing cinnamon rolls.

Finally, we arrived at the cabin in the woods, near a lake:

Cabin in the woods!

Cabin in the woods!

As soon as we got there, he built a fire and made us whiskey cocktails. In celebration, I threw my panties on the fire – I couldn’t help myself! They were kindof ugly anyway. No undies for the rest of the weekend! We mostly stayed in robes or were naked.

We brought loads of pillows and super soft blankets to snuggle up in by the fire. One of them is a fake fur pattern – made me feel like we were in a cave!

I loved stroking the fur, and then my soft tummy, sipping hot toddies and reading gorgeous books, the fire crackling and throwing warm light:

Soft blankets, soft tummy

Soft blankets, soft tummy

We had an amazingly hot roleplay scene in the hot tub (SEX+STL is giving a roleplay talk today!)

Here is the path leading to the hot tub:

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Playing the Virgin

By Kendra Holliday | July 2, 2016

Guess who is the opposite of a virgin?

ME!

Guess who loves the land of make believe?

Yes, Mister Rogers. But also,

ME!

And Matthew is my magical play partner. I’ve been with men in the past who were uncomfortable just having phone sex, but luckily for me, this man is down to roleplay an entire evening.

This vintage sheer gown inspired me, and away we went into fantasy land!

You, too, can be a sacred prostitute goddess!

You, too, can be a young virgin with the right imagination!

I was housesitting at a beautiful Victorian home, so it was the perfect setting for our fantasy.

We came up with it together – I was a 22 yr old sheltered, homeschooled girl named Katie. He was 36, and I had met him a few years ago at some homeschooling conference where he gave a presentation for grad school. I ran into him at some small town festival that day, and since my parents were out of town on a church trip, I invited him to come over that evening to hang out.

I had a crush on him and was hoping to make out, but had never done anything beyond first base. So I put on the costume, and he left the house, waited a moment, and then knocked on the front door.

From that moment on, he was the older, experienced man, and I was the shy girl who had no idea what she was getting herself into…

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Want a Tantra Goddess in the Midwest?

By Kendra Holliday | May 11, 2016

Urban Tantra by Barbara Carrellas

Urban Tantra by Barbara Carrellas

For years, men, women, and couples have been asking me if there are any Tantra teachers in the Midwest. I knew of one in Kansas City, but she disappeared a few years ago. It looks like there are one or two active goddesses in the Chicago area.

I’ve dabbled in it – reading books like Urban Tantra, browsing websites and watching videos, but am by no means an expert.

So over the years I’ve put the word out to the local community seeking tantra experts. I found one man who was willing to speak to my group Sex Positive St Louis, but he canceled two hours before the talk, so I had to wing it!

I talked about my experiences with yoni eggs, energy orgasms, extended orgasms, kundalini, and more.

The Sacred Prostitute

The Sacred Prostitute

Recently, we found another man in St Louis named StarDancer who was willing to talk about his energy body work to the group. Hearing him speak really inspired me to investigate the Tantra realm further.

I had a revelation – I want to bring Tantra from a female perspective to St Louis! I already do sex surrogate work as a sacred prostitute, so this seemed a natural step in my career as a sexuality expert.

I found out that Barbara Carrellas is offering a Tantra training workshop in New York City June 10-16. Thanks to some generous sponsors who believe in my mission, I AM GOING. I’m SO excited! It will be my first time in New York City. I can’t wait for an invigorating change of scenery and for my universe to expand!

Barbara was featured on Strange Sex demonstrating her full body energy orgasm technique, aka “thinking off” for a group of scientists. She’s the real deal!

Here is more info – Barbara’s intro on the program

More about the program

Details about registering for the program

More info on Barbara Carrellas – she’s a certified sexologist who has worked with the likes of Annie Sprinkle teaching Sacred Sex techniques! She’s very inclusive and positive in her teachings – more practical and modern than woo woo, she revels in, teases, and plays with traditional Tantra, all while honoring Tantra’s rich spiritual tradition of connection. She teaches all over the world, so it’s nice having a class offered in the U.S.

I’m excited to bring what I learn back to St. Louis. Thank you for believing in me and helping expand our collective sexual universe!

Sex work can be a beautiful thing.

Sex work can be a beautiful thing.

 

How to Make That MFF Threesome Finally Happen

By Kendra Holliday | April 24, 2016

Girls wanna get down, too!

90% of men who crave female energy love the idea of being in bed with two women at once (the other 10% think it would be too much work).

An MFF (Male-Female-Female) Threesome, or King menage a trois, can be, depending on who you are with, HOTTER than you ever imagined, or bad sex x2.

But the key to making your threesome fantasy a reality is not finding the right women – it’s having the right mindset.

Most everyone thinks about threesomes, but without being open-minded and available to a person who is equally open-minded, those sorts of fantasies will never materialize.

Let me share my own personal experience on the matter. I dated a man, and after a few months of being together, I confessed to him that I was bisexual and thought it would be hot to share him with another woman.

This sparked a fervant quest to make a threesome happen. We joined dating sites, chatted women up online, all to no avail. Just because we wanted to have a threesome didn’t mean random women wanted the same thing.

Then things got interesting when I approached him with my second confession: I liked the idea of being with other men, too.

This dumped a bucket of ice water on his sex drive. We almost broke up over it! Here I was, open to the thought of him being with other women – dating other women, playing with my girlfriends – but the thought of me being with another man was a dealbreaker? Buzzkill!

During one late night tense discussion over it, he declared, “I will never be comfortable with the thought of you with another man.”

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Arousal: The Secret Logic of Sexual Fantasies

By Kendra Holliday | April 17, 2016

Arousal: The Secret Logic of Sexual Fantasies, by Dr. Michael J. Bader

I’ve had the book Arousal: The Secret Logic of Sexual Fantasies on my shelf for a long time. It tempted me with its mysterious title and sexy cover (I LOVE oysters, and I LOVE my pearl, if you know what I mean).

Well, I finally dusted it off and read it, and it blew my mind, and I’ve been recommending it to people left and right ever since.

Here’s an intro concept from it that should provoke your thoughts:

“There’s a joke that says that when two people have sex, there are six people in bed: the two lovers and the parents of each of them.”

Is that creepy, true, or both? I hope you’re imagining group sex with your parents right now.

A sampling of the MANY interesting points brought up in this book:

– “Sexual excitement requires that we momentarily become selfish. There needs to be a tension between selfishness and caring, between using and pleasing your partner.”

Do you know what this means? Sometimes, when it comes to sex, you need to be ruthless. You need to let go and stop worrying so much about every little move and just focus on the pleasure. YOUR pleasure.

– The difference between guilt and shame: “Guilt involves beliefs that we are hurting others, while shame involves beliefs that we’re exposed and unworthy in the eyes of others.”

– “When people are aggressive or cruel in their sexual daydreams or practices, it is not because they are primarily sadistic but because they are trying to solve a problem.”

– Have you ever known a woman who is really bitchy toward her male partner? He’s such a nice guy, he tries so hard to cater to her wants and needs, yet she treats him like an annoying puppy? This book explains the reason behind that lopsided dynamic.

– Survivor guilt and unconscious parental jealousy is behind a lot of the issues we face with our parents. Have you ever wondered why someone would start drinking heavily when they became successful in their field? Or why some parents sabotage their kids and excessively criticize instead of support them in their endeavors? This book goes into the details behind those perplexing behaviors, and much more.

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Bra Shopping With Fifi

By Kendra Holliday | March 4, 2016

Ed Note: This is the prelude to my most perverted pinnacle moment! This regular guy had some crazy fetish fantasies and asked me to help him make them cum true. Let’s call him Fifi.

TIME TO BE A BITCH

TIME TO BE A BITCH

Fifi asked me to take him bra shopping. He also asked me to gift him with a load of cum – he wanted me to force him to eat it, a sneak preview of our grand session coming up.

He was already wearing thigh hi stockings and black panties under his khakis when he picked me up. I came out to the car carrying the cupful of cum from my fridge that I harvested last night.

I asked him, “Do you want this right now? It’s cold.”

He gulped and said, “Whatever you want me to do.”

I smiled slyly and said, “I think I’ll set it between my thighs for a while and let it warm up.”

We drove to the mall. We had to drive to one in Illinois because he didn’t want anyone from his church to run into him at the local mall.

Every once in a while, I would pick up the cup and give it a swirl, checking its consistency. I gave it a sniff. “YIKES, that is bleachy. Here, you smell,” and I thrust it under his nose so he could take a whiff. He cringed. I smirked.

“You know, this load was meant for me. He told me to swallow it, but I was good enough to save it for you. I’m very nice to share, don’t you think?”

He said yes.

We pulled into a parking spot at the mall. A family with two adults and some kids sat in a van opposite our car. Perfect.

I turned to him and announced, “I think we’ll give you cum breath before we go shopping. And look – you have an audience!”

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A Sex-Positive Gang Bang

By Kendra Holliday | December 4, 2015

SO. This week’s Savage Lovecast featured a woman calling in asking about a gang bang gone wrong. You can listen to it here, around the 30 minute mark. The good news is, she had two gang bang prior to the bad one that went GREAT, but the last one tanked. The reason: the men got too rude and selfish. Dan gave her great advice – have a gang bang buddy, and know who’s in the room! Below is my super amazing gang bang experience. I hope you take some ideas from it if you’re thinking about staging one for YOUR loved one (that includes YOU!) A loving shout out to the people who were involved in mine – they all made it so very special. It truly was a dream come true – it made for a VERY happy Holliday! 😉

——–

Would you be nervous if you knew eight men were on their way over to fuck you all at once?

Would you be nervous if you were a man driving to a gang bang event, having never met some of the other guys, and this being a new experience for you?

Think about it for a minute.

I mean, gang bangs seem like a hot idea in fantasy, but how do they translate in reality?

Well, when you plan it right, they translate really fucking well.

Truth be told, I wasn’t nervous. I was excited. I was radiant.

This pic was taken after it was all over. Photos by David Wraith!

This pic was taken after it was all over. Photos by David Wraith!

Now, if I was about to do public speaking, I’d be nervous. If I was about to parallel park a car, I’d be nervous. If I was about to walk into a rich country club, I’d be nervous.

But this was natural for me, even though it was my first time trying such a thing. As you all well know, sexual acts are where I shine.

Here is me right before the guests arrived:

Kendra Holliday, Slut Extraordinaire!

Kendra Holliday, Slut Extraordinaire!

See? I’m making the OK sign. 🙂

I dressed up because all the guests were coming in suit and tie. Classy!

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Masturbating to the Dishwasher

By Kendra Holliday | October 14, 2015

I’m not sure where to begin with this one, but it’s been a very strange week.

So many good, bad, and GREAT things are being thrown at me at once. My head is spinning! A really odd chain of events. Seriously, read on.

First of all, I’ve been coveting a sex toy for months called The Womanizer. I finally scored one, thanks to a virgin from Minnesota who gave me an Amazon gift certificate. He’s coming to visit me next week, and my guess is he won’t be a virgin by the time he leaves St. Louis.

I charged it up the other day,

Charging up the Womanizer

Charging up the Womanizer!

and my partner Matthew requested that I use it for the first time with him present. He wanted to be there for my first orgasm with this super special, virgin funded toy.

But despite all the rave reviews I found online, I couldn’t get off! It tugged on my clit and shot odd sensations up my nervous system, but I kept tripping up. I finally gave up in frustration. Not with the toy, but with myself.

“Maybe it’s better as a solo toy,” he said reassuringly.

Phew I'm tired!

Phew I’m tired!

Grumpy and disappointed, I set it aside for days. He kept asking if I tried it again, and I said no.

Also this week, my dishwasher broke. I have this weird relationship with dishwashers.

You see, when I was 18, my mom kicked me out of the house for not emptying the dishwasher. It wasn’t my turn to do it, but she was crazy and didn’t care. So she put all my stuff out on the front porch in paper bags, and I was homeless.

For years, I lived from place to place, and most didn’t have a dishwasher.

So when I finally moved into my house and it had a dishwasher, I was SOO happy. I LOVE having a dishwasher. I like emptying it and restoring order in the kitchen. I love running it at night – there’s something very soothing about the tumbling sound it makes as it magically cleans and steams the dishes, like an elf fixing shoes for the sleeping cobbler. You wake up in the morning, and voila! Sparkle!

Trouble is, I’ve been having terrible insomnia lately, and the dishwasher I’ve enjoyed for the past eight years was kerfucked. And RIGHT when I started using Blue Apron.

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How to Get Hired as My Subby Bitch

By Kendra Holliday | August 29, 2015

TIME TO BE A BITCH

TIME TO BE A BITCH

The majority of submissive men are so annoying!!!

As a sex worker, I can tell you that there are A LOT of submissive men out there.

And they are cluelessly milling around, desperately seeking Mistresses.

The definition of Mistress is this: “a woman in a position of authority or control.”

Sounds good, right? Trouble is, they’re so warped by our patriarchal society, they have it all twisted.

This is what they THINK it means: “a woman to be manipulated to fulfill every whim for the benefit of a silly penis.”

Fuck this Mistress shit. I am a GODDESS. I am a QUEEN.

That means whatever I say, GOES. Fuck your preferences. I mean, if I can do right by you, I will, but it’s really all about me, the Queen, and not you, the lowly minion with an eager dick and shallow wallet.

In our society men are not allowed to fully mature. That’s why I offer finishing school.

The words “entitled,” “eager”, and “annoying” should not come to mind as I review your application.

And in case you haven’t noticed, finishing school is NOT CHEAP.

Take Ceara Lynch ….  just look at what she has to deal with. Sometimes she makes more than $1000 a day, and she EARNS EVERY PENNY. And since she makes so much damn money and knows sub men are plentiful, she offers tips on how to become a humiliatrix.

Here are three recent examples I’ve had to deal with – I’ll never get these 10 minutes back, and neither will you:

  1. panty guy
  2. servant foot sniffer guy
  3. spanking guy

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Today I had ladies over for tea while @davidwraith organized my shoes, mopped my kitchen floor, & shelled my nuts.… https://t.co/EgzfhgFwUD

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Just listened! Thanks a lot 😖 https://t.co/lfhngJg4WZ

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The Midwest has so much horny. Represent! https://t.co/ktZZGvE2SL

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A lover gave me a Victoria’s Secret gc! I doubt I will look as American Beauty, but I ordered this. 😻 https://t.co/xl1ZRvNIsQ