By Kendra Holliday | July 14, 2018
Category Archives: Fantasies
Last week, I posted about a fantasy I wanted to make happen in real life with Matthew and Lana.
Today, I detail how things really went down. You be the judge – which is hotter, the fantasy, or the reality?
First of all, my fantasy included cum play and cream pies, which involves risky behavior. All parties need to trust each other and get tested.
So, we did.
The day of our date, Lana texted us the good news about her test results:
Now we were ready to make it happen! We were all SO excited – the fantasy matched each of our desires perfectly. Anticipation served as foreplay all day – all week, really.
The evening started with us chatting over drinks and catching up. Matthew warned her that he hadn’t been inside a pussy for 21 days, and hadn’t busted a nut in three days, so things could get crazy fast.
Sure, we were throwing down, but we were doing so in style. Candles were lit, and romantic Brahms played in the background
I wore a neutral, mesh teddy that accentuated my curves and nipples. She wore a short little black teddy with pink lip prints all over it.
He started things off by cuffing my hands behind my back. I tried resisting just for fun, but it was like slicing into soft butter with a sword – no contest. He had me locked down firm, then gave me a sweet kiss on my quivering lips, and tied the small, silver key to one of the strings hanging off the teddy’s neck. Then, he sat me down on a small tan tuffet at the foot of the bed, fashioned from a folded blanket. I was out of the way, and in position. He murmured, “Sit. Watch. I’ll be back.” I obeyed, like a well-behaved puppy expecting a treat. She stared at our exchange, wide-eyed.
Then, he turned his attention towards her. She stood there, looking up at him expectantly. He kissed her, hands roaming over her body, caressing her breasts through the gauzy fabric of her teddy. He spun her around and kissed her neck and shoulders. She moaned slightly as he pressed his swollen cock against her soft panties. He pulled her lingerie off, caressing her now exposed nipples, kissing her neck hungrily until she almost came. He stopped short of her explosion….
By Kendra Holliday | July 14, 2018
In my last post, I told you about a twisted, romantic fantasy I had, and how we were going to act it out in real life with Lana. Today, I am posting the fantasy. Next week, I will post how it played out in real life. How did it match up? How was it different? Which is better – the fantasy, or the reality?
Here is what I have in mind for us to do tonight.
You set the scene, and get me situated. I’m kneeling on the bedroom floor, naked, hands cuffed behind my back. Normally, I’m very much involved in our powerfully charged sex acts, but not tonight. Restrained, I can only quietly observe what is about to transpire.
Then, I watch you seduce beautiful Lana, standing there, kissing, hands roaming. The room is dimly lit, it’s romantic, you’re focused on her, I’m a fly on the wall.
Next, I imagine you in bed together, a sheet over you, seeing your big, bristling, muscular shoulders and chest compared to her smaller frame.
Her hair is all wild, you’re lying there kissing. You do whatever slow foreplay, oral or whatever, but I imagine you sucking on her breast as she gently tugs on your cock.
She wants it.
Your cock is STRAINING and finally you can’t wait any longer, and with a gentle growl, you push her legs apart with your thigh. You have to be inside her.
Now is the time.
You push and coax your way in, she readily receives you, she’s so hot and soft, finally you two are plugged in, skin to skin, snug. You’ve already made her cum, so that is not the goal here. Sure she can enjoy it, but this is for you, so you can finally fill her with cum and mark her, after knowing her for more than a decade. You’ve been biding your time, waiting for the right moment, but who would have known the right moment would involve the love your life being witness to this sacred act?
By Kendra Holliday | July 13, 2018
The other night, I witnessed my friend Lana have her first MFM (Male/Female/Male).
I sat in a chair at the foot of the bed, fully dressed, wrapped in a soft blanket, goblet in hand.
I felt like this:
She, on the other hand, was naked and blindfolded on the bed, being worked over by two muscular, horny men. She looked so gorgeous and vulnerable in the warm, dim glow of the bedroom chamber.
I pretended that I called for them and that this was my entertainment of choice for the evening – to watch a lady-in-waiting get stripped of her gown, used, and impregnated.
By Kendra Holliday | May 18, 2018
When a pretty girl (aka Kendra) says, “I’ll fuck you,” you say, “Where and when?”
“My place.” Then, that same pretty girl ups the ante by saying, “How about we make it into a party? As in, multiple girls pleasure you while some other lovely ladies watch?”
“Hmmmmm…..you mean you can arrange for multiple women to feast upon my sex, while we perform an exhibitionist show for other girls?”
“Sure!” Kendra says with a mischievous grin.
“Like, how many girls are we talking here? 3 or 4?”
“Let me see what I can do.”
By Kendra Holliday | May 3, 2018
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.”
By Kendra Holliday | March 27, 2018
This list is lovingly dedicated to everyone who pshaws at vanilla sex.
1. fuck someone who is actively bleeding, OR earning your tasty Red Wings
2. fuck in a coffin or a church
3. genital torture using a starving hamster
4. pegging with a peg leg
5. extreme anal penetration with something found in the kitchen
6. watersports in a water park (ha ha, too bad, everyone else!)
7. fucking someone you have rendered unconscious
8. knifeplay at a sushi bar
9. sucking a dirty dick (where has it been?!)
10. take down abduction scene at Wal-Mart
11. taste cum, preferably on a muffin
12. putting a stick of huckleberry incense in your ass and lighting it until your ass hairs singe
13. masturbating to a photo of your parent
14. putting a fork, spoon, and knife in your orifices simultaneously
15. face sat upon by someone naked and unwashed until you can’t breathe for two minutes
16. shave entire body
17. sucking the horn of a poached rhinoceros after it’s been shoved up Rush Limbaugh’s ass
18. fisting with Paul Bunyan
19. sex on horseback (with the horse)
20. being fucked by someone you never see, preferably because you are half buried in dirt
21. figging using an entire bottle of ginger liqueur
22. double penetration (eyeballs and earholes count)
23. sounding using the chopsticks from a racist Vietnamese restaurant (more…)
By Kendra Holliday | March 25, 2018
I asked readers to suggest sex acts that everyone should try at least once. Now, this list may not be as kinky as you might expect. That’s because I chose to focus on sensualism and intimacy over fear factor stuff.
So, you’ll find a lot of creative vanilla acts, but things like genital torture? Not so much. I was also able to consolidate a lot of things into one entry, such as anal play for rimming, receiving, pegging, etc. This gives you more flexibility when planning out your sex menu.
Thank you to everyone who contributed to this list. Please comment on how many of these things you have done, and what stands out as something you’d like to try soon!
2. mutual masturbation
3. sexual encounter with person of a different gender
4. same sex encounter
5. male-female-male threesome
6. male-female-female threesome
8. using a condom during sex
9. using another form of birth control
10. getting/giving spanking
11. phone sex
13. writing/drawing on your partner
14. combine food and sex in some way
15. sex while being restrained in some way
16. one night stand
18. orgasm three times in one night
19. morning sex
21. afternoon sex
22. middle of the night sex
23. have sex while wearing a costume
24. cross dress
25. give oral sex
26. receive oral sex
27. have sex with a friend
28. wait a long time to have sex with someone you’ve been crushing on
29. get a full body massage (more…)
By Kendra Holliday | February 17, 2018
Ed Note: This post was written in 2009. It is the only post I have ever published that was untrue, in that I combined two scenes into one story – one involving rape fantasy in a parking garage, the other being gunplay in my home. Boy, did I learn my lesson with this one. Readers were OUTRAGED we would roleplay something so deadly in public…and it was the same day my partner’s ex discovered my blog. Yikes. I put him in a very compromising position. I’m reposting this as a reference to a slideshow presentation I’m giving in London next month. It’s called “Shocking the System: When Your True Life Tales Cross the Line. It will be previewed at Shameless Grounds on March 3, at 3pm. Come and see for yourself.
Matthew was using his dad’s vehicle for the week, which means he had access to a handgun and a gleaming, ostentatious SUV.
Just add Republican.
He’s forever challenging me, and this adventure was no exception. For the record, I am a hippie and vehemently opposed to guns and SUVs. I SUPER HATE guns. They scare the shit out of me.
After lunch, we walked back to the SUV that was parked in the dark, dingy parking garage. Lunch was like foreplay, I was SO ready to rock the truck. Plus, I hadn’t fucked in an SUV since 2007.
But of course Matthew had to add his own creative twist. He opened the passenger door for me like the gentleman he is, but then – surprise! – he leaned in and grabbed an *unloaded* handgun out from under the seat. He pointed it at my head and shoved me to my knees. WTF?!?! Heart pounding, I knelt on the dirty concrete as he pulled out his already hard cock and told me to suck it.
The cold metal pressed against my skull as he used my face. I looked up at him, wide eyed, completely freaked out. He looked down at me grimly. No one was around.
Then he pulled his cock out of my mouth and I clamped shut. He brought the gun to my lips.
I shook my head vigorously.
He grabbed me by the jaw and squeezed hard. “OPEN.” he hissed.
By Kendra Holliday | December 30, 2017
One year on Twitter, I listed one of my fetishes every day.
Fetish: something that sexually charms you.
I went back and looked at the list and was turned on and amused!
Here is the list in its entirety – I replaced about ten of them. If I’ve featured one in a post, I will link it to that post.
Mmmm, I want them ALL! Do any themes jump out at you? It’s clear I’m into hair, booze, and incest!
What about you – how many things turn YOU on?
1. Hairy chest
2. Steel handcuffs
3. Having my lingerie ripped (panties, stockings, fishnets)
7. Redheaded women
8. Pre-1968 Elvis
9. Reaction cologne
11. Sleeping Beauty
13. Feeling hard cock through jeans/pants
14. Incest Fantasies
18. My man’s cum inside my pussy
20. Japanese Gardens
22. Bruce Springsteen
24. Bubble baths
25. Magic Wand
28. Arched doorways
29. A REAL beard
30. Mood lighting
33. Long skirts
35. Victorian Homes
37. Hairy underarms
41. Classical music
43. V-Safe Men
45. Period films
By Kendra Holliday | December 29, 2017
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.
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!
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!
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!
— Kendra Holliday (@TBK365) October 7, 2017
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.”
By Kendra Holliday | July 16, 2017
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!
By Kendra Holliday | April 11, 2017
I’ve had this “I Dream of Jeannie” outfit for a few years.
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.
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!
So after teasing my partner like a matador does to a bull
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.)
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.
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”.