Category Archives: Passion & Intimacy

Why Creative Sex is Better Than Straight Sex

By Kendra Holliday | April 14, 2019

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 11 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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How Do I Exercise My Open Marriage?

By Kendra Holliday | March 23, 2019

Dear Kendra,

My wife and I recently decided to open our marriage. Unfortunately, I’ve run into a problem: women don’t seem to want to get involved with a man who is in an open marriage.

So far the three women who I’ve approached, although they admit being attracted to me and interested in the idea, have all given me some variation on the same objection: they’re worried about hurting my wife or causing harm to our relationship. These women know both my wife and me, and they aren’t willing to even acknowledge the possibility that talking to my wife could resolve their concerns.

I can’t help but find this fairly insulting. These women seem to be substituting their own judgment for mine and my wife’s, and telling us that, as much as we might think we’re ready for an open relationship, we will inevitably fall victim to jealousy and bitterness.

Now, I can understand that some women may not want to take any risk of being responsible for that, no matter what the people in the relationship might say, and maybe there’s nothing I can do to change those women’s minds.

But how can I best explain that they don’t have to worry about causing harm to our relationship—and that even if that happened, it wouldn’t be their fault—and how can I maximize the chances that they’ll overcome their feelings of unease and be willing to get involved?

My reply:

I asked a couple successful poly guy friends of mine for their 2 cents, and their combined answers added up to at least 2 bucks! Here is J’s take:

“Why not approach women who already identify as poly themselves and have other already established relationships? You can join a poly group in your town and mingle with like-minded people.

Of course I realize that’s a tough pill to swallow when you’ve already got what seems like three perfectly willing takers–if only it weren’t for their warped view of his wife, the mutual understandings they may have in their relationship …or what, on principle the sanctity of his marriage to her? Yeah, honestly I’d feel somewhat insulted by these assumptions of overreaching responsibility and risk too.

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An Ode to Vanilla Porn

By Kendra Holliday | March 17, 2019

X-Art features women like this

A friend of mine is not a fan of hardcore porn. I asked him to tell me what kind of porn he enjoyed, and he wrote me this letter. Enjoy!

Kendra —

I realized, after a lifetime of looking at porn, that I don’t like almost all of it. It’s grotty, unpleasant, populated by people I don’t want to talk to, let alone fuck, and the more extreme the porn makers become,  to stand out from their competitors,  the more they turn me off, both because of the scenario presented (I don’t want to rage-fuck someone in a basement) and because of the tragedies inherent in the production.

Young women with too much makeup and plastic surgery don’t turn me on, they make me sad and wonder about where their parents are.

But I recently came across some porn that seems designed specifically to appeal to people like me — which I would define as oversexed, heterosexual white males.  It’s made by X-Art, and is the Platonic Ideal of Vanilla Porn. Looking at it (which I’ve done a lot) made me think a lot about the kind of porn-fantasy it presents, and why its so appealing.

A typical X-Art vid features a young woman, with a body unaugmented by wear,  surgery or (too much) makeup. The setting is a high end apartment (many of the vids seem to be shot in the same LA loft) that might be the home of a protagonist in a Hollywood film. The man is attractive, but not the focus at all… there are a number of videos in which you rarely even see the man’s head.  Everybody is young and perfect; hairless, both metaphorically and literally.

The music is different than typical porn. Many vids start with a cool, indie sounding pop song, the kind of thing attractive people might listen to in their excellent apartments, and then they fade out in favor of “natural” sounds. No wocka-wocka bass line to constantly say PORN. (more…)

The First Time We Made Love

By Kendra Holliday | October 24, 2018

Ed Note: I’m so glad I captured the first time my partner Matthew and I made love…this was first published in Nov 2008. Celebrating 10 years of love!

Pluots

We are sitting on the couch where we had our first Cuddle Movie night six months ago. Soft music is playing, a candle is lit. We’ve spent the past couple hours talking, updating his online dating profile, catching up. We are terrific friends, but I want more than that. I sit close to him, but really I want to crawl right inside him – I can’t get close enough.

I watch his every move hungrily and shyly – I pay attention to how his great hairy arm flexes as he cuts into a tight, round pluot streaked with red and orange with a paring knife. He balances a slice on the end of the knife, looks me in the eye, and offers it to me.

I reach to take it, think again, lower my hand, and allow him to insert the knife inside my open and waiting mouth.

“Careful,” he whispers as the fruit slides off the blade. I bite down on the sweet, firm flesh.

He switches to hand feeding me, and his fingers touch my lips. I feel like a baby bird – at least, inside I’m clamoring, frenetic…

He finishes feeding me, sets aside the plate, and puts a paw on my neck and kneads it.

“You’ve got a knot,” he murmurs. “Come down here,” he gestures to the floor in front of him, and I kneel facing away from him. He rubs his rough hands together rapidly to generate heat. I close my eyes as he lays those hot hands on my neck…the back of my head…and works my kinks out.

He takes one of my braids and slides off the band, then loosens it. My hair spills silky through his fingers, falls loose down my back…he undoes the other. My head tingles at the gentle ministration.

Love washes over me.

I can’t stand it anymore. Even though I am nervous, I stand up, face him, take a deep, shuddering breath, and climb onto his lap. I straddle him like a horse. I almost expect him to shove me away,  it’s like a dream, too good to be true, but he allows me melt into him…

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Moongasm on Monks Mound

By Kendra Holliday | September 23, 2018

Last Saturday was the night of the Super Moon, the one time of year when the full moon would be closest to Earth.

Full moon

We had spent the day hopping from friend to party to friend to parade, drinking and being merry – it was a full day. It was a LOT of day!

It was a great day.

After the craziness of a busy festival in Soulard, we chilled at our friend Shine’s house. It was a stark contrast to the packed street party that was jammed with people, bright lights, and HEAT – Shine’s house was cool, dim, and surrounded by resting plants. It was just the four of us.

Monks Mound – the largest human-made mound in the United States

She mentioned that the night before, she had been to Monks Mound to celebrate the moon. Monks Mound is in Cahokia Mounds, across the river in Collinsville, IL. Monks Mound is the largest human-made mound in the country. She spoke of how powerful it was to be so close to the moon, fog in the valleys, the energy of all the people who had once been there…. 20,000 people lived there, making it larger than London in 1250 AD.

After a raucous family dinner, we made our way over to Illinois. The surrounding area was a little eerie – rundown homes, race track, landfill, liquor stores, ghost towns – a lot of buried dreams.

It was dark. We parked near the mound. Technically the place was closed, but it felt like a free country and we meant no harm, so we ventured out into the moon-drenched surrounding meadowscape.

I was barefoot, wearing a soft, flowing moon dress. We held hands and walked toward the looming mound. No one was around.

Up the first level we went, then the second. Finally, we were at the top. (more…)

My Date with Orville

By Kendra Holliday | September 2, 2018

I adore cute little old men, so when one contacted me online asking for a date, I happily agreed.

We met in the dim, red, richly appointed lobby of a luxury hotel. We were both a little nervous. I had no idea what he looked like.

I was relieved when one of the anonymous men standing around broke away from the faceless crowd and warmly approached me. I got instant good vibes from him.

Orville.

He resembled an Orville. He was small and neatly groomed, very dapper in his three piece suit, right down to his silver tie pin and cuff links. With my elegant black dress and pearl necklace, we made a smart looking couple.

He ordered me a glass of wine, which I sipped politely as we got to know each other on a velvet sofa in a cozy corner.

He was from out of town. He summered in Cape Cod and wintered in Florida, having a home in both places, as well as one in Virginia.

He had a wife of 45 years who was a good woman, but never touched him, not even holding hands while they watched a movie, lest he get the notion that this basic physical contact would lead to something more. She had no interest in intimacy or sex – she found it distasteful and unnecessary – and expected him to follow suit.

Trouble was, he was a human being. Humans NEED physical contact. Which is why he sought me out.

A lot of people think whores are homewreckers, when actually the opposite is true. They do a great service keeping marriages together.

Many straight men NEED to sip from the cup of feminine energy just as they need to breathe and eat. If their wife cuts them off, they will look for intimacy elsewhere, or suffer miserably.

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Tristan Taormino’s Expert Guide to Advanced Anal Sex

By Kendra Holliday | September 1, 2018

Would you like to know your asshole better? How about someone you love’s asshole? Do you wish you could stick things in it in a way that feels intensely amazing, but are not sure how?

Anal is one of the sex acts I get asked about the most, mainly from women who fear it, and men who want to explore it. To that, anal expert Tristan Taormino chirps, “What’s up, chickenbutt?” OK, not really. Instead, she makes videos.

For the newbie set, I recommend Tristan’s initial video on the subject, Expert Guide to Anal Sex.

For those who want to take it to the next level, there is the newly released Expert Guide to Advanced Anal Sex.

Tristan Taormino’s Expert Guide to Advanced Anal Sex stars Nina Hartley, Bobbi Starr, Kylie Ireland, Adrianna Nicole, Mr. Marcus, James Deen, Danny Wylde, Christian, with special appearance by Sinnamon Love and Tyler Knight.

Note: Bobbi Starr was so charming and special, I had to go look her up. She reminded me of a friend of mine, proof that she nailed the “girl next door” schtick. Bobbi talks about how she only does anal for work because she can prep properly; apparently, sex at home is more spontaneous. It’s so cute hearing a porn star admit she’s self-conscious about making a mess!

First things first: This video is SO respectful.

AND educational. Which might make you think it’s not sexy or worth jerking off to. But it totally is! Tristan manages to include so much information into this video that you can easily flip between learning about how to give an enema to sitting back and getting erotically lost in an intense scene for three hours.

This is a picture of my butt,
which I felt was appropriate
for this review

I hope I watched it all – it went on and on, it’s packed with scenes and info. I dunno, there might be some hidden butt plugs I missed.

Watching this video reinforced my respect for porn stars. They are such good, giving, game athletes. So refreshing to see people explore their sexuality in a shame-free zone.  So many people are so secretive about their sex life and act like it’s a private activity that should be conducted behind closed doors, like going to the bathroom, so it felt very open-hearted for these performers to keep the door open for us on their backdoor activity.

These are professionals who want you to try this at home.

I love the conversations with the stars before they commence to fucking. There is more eye contact and kissing than you would expect for anal. Watching them kiss is what is personally hottest for me.

The actors have real chemistry and connection, they smile, appear relaxed, I get the impression they are friends in real life.

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A Date With a Gentleman

By Kendra Holliday | July 7, 2018

(This is not a pic of him, but of some random gentleman)

So, we’ve been dating this sweet ‘n sexy couple for the past year or so.

It’s been very slow going because we’re all so busy. We finally realized we had to carve out time with each other in order to have special dates, so one week I went out with the husband, and Matthew had a date with the wife a couple nights later.

Let me tell you about my date first – he was such a gentleman!

I wore a pretty, silky jade dress. I felt a little nervous! I was excited to finally have a chance to talk and bond with him in an intimate manner. We had sex once before, months ago, but it was a totally different feel – anonymous and clandestine, with no words exchanged. So even though I had a sneak preview of his prowess, tonight felt brand new.

He came to my door and knocked, presenting me with a bottle of wine and a bouquet of lettuce greens from his garden! He complimented me on my dress and opened the car door for me.

We went to The Fountain on Locust for drinks and dinner. He knew right where he was going, and I didn’t have to worry about a thing!

This was our first chance to enjoy one-on-one quality time with each other. He made me feel so special. I was in a delicate, feminine mood that night. He asked me questions and listened thoughtfully as I babbled away about all kinds of things. He had such a confident, gentle demeanor.

The Fountain served us AMAZING ice cream martinis, which we kept sampling throughout dinner. Our server was amazing and added some electric energy to the atmosphere. His intensity made me blush when he took our drink orders. I love the decor, too – all blue and gold, art deco.

When we got back to my place, he went to pour two glasses of wine for us. When he returned, he found me wearing only lingerie – I couldn’t wait to slip my dress off!

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My Daughter’s Date Ideas

By Kendra Holliday | May 26, 2018

My daughter when she was 5

My daughter when she was 5

When my daughter was 7 years old, a boy kissed her hand on a dare. She confided to me, “It was the most enjoyable moment of my life.”

Now she is 17, and identifies as asexual. She doesn’t feel sexually attracted to other people, but she yearns for romance. She wants to hold hands, cuddle, and be intimate with someone special.

I’m thrilled to tell you she went on her first date the other night! They held hands!

I asked how their date went, and she gushed to me, “It was AMAZING. Not only were the events we attended awesome, but he was super sweet. He put his arm around me during the movie, and we held hands twice and he is so very kind all the time. God, I adore him, he made it so amazing.”

He’s like a young George RR Martin, they’re so cute and nerdy together.

I’m SO happy with this new development. She tends to brim over with teenage angst and melancholy, so it’s wonderful picking her up from school and she’s smiling so hard, her face hurts. The rush of happy hormones and feeling connected to someone special to her is better than any pill she could take!

I asked if he is her boyfriend, and she said she didn’t know, but she would ask him. She has ups and downs, and frets over being too direct with him.

King and Queen of Love!

King and Queen of Love!

I reminded her that she is probably advanced in the realm of communication, and needs to be patient with others and teach them how to be open and honest. I also let her know that the wonder is part of the fun of the early stages of a relationship – infatuation is a trip, and you should let it last as long as you can! After that, you get into attachment, feeling the person is a safe haven, then anxious when they are not around, then finally, secure (if the relationship is healthy.)

That’s where I’ve been with my partner Matthew for the past six years or so. We can’t go back to the infatuated stage with each other, but since we are polyamorous, we can feel secure while flirting with other people and enjoying novel experiences.

Anyway, my daughter shared her list of curated date ideas with me and gave me permission to share them with you. I think they’re so cute! She made most of them up, and collected some from the internet. I want to do a lot of them, how about you?

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Basking in the glow of male energy

Basking in the glow of male energy

The book King, Warrior, Magician, Lover: Rediscovering the Archetypes of the Mature Masculine explores the archetypes of the mature masculine. Men who act out, have temper tantrums or are violent – jerks, bullies, know-it-alls and thugs – haven’t reached their full potential.

Men aren’t allowed to fully mature in our society. There is no rite of passage. The spoiled little princes of the world have work to do if they aspire to be superior men – if they want to be King.

The author Robert Moore is a psychologist in Chicago, IL. You can read more about his theories and discoveries here.

So how do you become King? Here is the book that perfectly mirrors our relationship dynamic: The Way of the Superior Man by David Deida. I underlined the shit out of this book. There’s no way I can feature all the awesome points, so please get a copy for yourself if you’re interested in tapping in to what makes our relationship so explosively orgasmic and fulfilling.

My partner Matthew hasn’t read the book, but that’s ok – he’s living it.

Here’s the premise. In order to have a passionate relationship with someone, you need to adopt a feminine and masculine contrast. It doesn’t matter who possesses the masculine or feminine – you can be a masculine female/feminine male couple, or a masculine female/feminine female couple, etc. The author maintains that 80% of people lean one way or the other – they either want to be ravished or do the ravishing.

For the most part, Matthew does the ravishing and I greatly enjoy it, I soak it up like a slutty sponge. But every once in a while, we’ll turn the tables and I’ll ravish HIM, which is just as fun and exciting. If neither of us assumed the ravishing mode, things would be more even keel. And boring.

That’s what happens in so many relationships – after the thrill of new relationship energy dies down, we get lazy and slip out of Lover role and become Managers, Caregivers, and Roommates. Then we take our partner for granted and lose respect for them and the sex turns lukewarm and resentment sets in.

So many men complain to me about how their wife doesn’t want to have sex with them, which makes him feel hurt and rejected. The reason the wife is cold to him is because she doesn’t respect him. The reason she doesn’t respect him is because he has let her down.

David acknowledges that most men want to have sex with other women, even if they are in a sexually fulfilling relationship. He advises, “If you want to be with other women, make sure you are taking care of the woman you have.”

Check his stuff out on YouTube – here is an example:

This is one of the books I recommend most. Click here to view my list of Top Sex-Positive Recommendations.

Bonus link: The Art of Manliness

My Top Sex-Positive Recommendations

By Kendra Holliday | February 23, 2018

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, 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, 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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Barbara Carrellas’ Ecstasy is Necessary

By Kendra Holliday | February 8, 2018

Book cover art

Barbara Carrellas has written a book called Ecstasy is Necessary: A Practical Guide.

This topic matches my life philosophy perfectly, which is:

As long as you take care of your duties and obligations and are not hurting anyone, you can have as much fun and pleasure as you want.

Simple enough, right?

Barbara’s book is about sex, but it’s so much MORE than sex – like I always say, our sexuality is connected with everything else in our lives. If we can address our sexuality without fear or shame, it frees us up to enjoy other aspects of our lives more fully.

Barbara Carrellas is a little woo woo,
and I’m OK with that

Barbara shares so many of the messages I spout, but she does so in such a loving, compassionate, patient manner. She does an excellent job explaining concepts that might be unfamiliar to the reader.

Therefore, it would greatly behoove you to read this book, as it will clarify and reinforce many truths about sex in a way that will make you feel safe and empowered.

For instance, she teaches the Something More Factor. No matter where you are when it comes to your own orgasms, whether you’ve never had one or have more than one a day – you can enjoy Something More, if you desire. You can have more orgasms, longer orgasms, deeper orgasms – and orgasms are one ticket to ecstasy and bliss. Having an orgasm creates similar brain waves as meditation. (more…)

Old Relationship Energy

By Kendra Holliday | January 31, 2018

I love Gwenn Seemel’s “The Kiss” featuring bonobos so much better than Klimt’s version!

Do you know the term “New Relationship Energy“? It’s popular in polyamory circles, and describes that giddy infatuation feeling when you’re dating someone new. It’s like a drug!

My daughter is experiencing it now as she’s dating a new boy. They are so crazy about each other! It’s so nice to find someone who is your champion, someone who makes you feel emotionally supported and loved – someone who gets you, despite all your idiosyncrasies.

I’m about to head out for my 10th cabin getaway with my partner Matthew. As I sit and reflect on how crazy we still are about each other after all these years (a record for me!), I appreciate how our connection has evolved into Old Relationship Energy. (Read this great list of ways to keep the spark in your relationship. And if you’re more monogamous-minded, do check out Esther Perel’s work on how to sustain a happy and healthy marriage.)

I remember the first year or two we were together, we had to have sex at least twice a day. If we were lying in bed together, he would be hard. We would have threesomes and foursomes all the time. It’s not like that anymore, but we still feel passion, deep connection, and mad respect for each other. We don’t have sex as often as we used to, but it’s still realllllly good.

Here is how we have maintained a decade of great emotional and physical fulfillment, despite all the challenges we’ve faced:

  1. Ah, the bliss of connection!

    We chose not to live together or combine our families. We have our own space and don’t have to go to family therapy!

  2. We didn’t get married. Been there, done that!
  3. We keep our finances separate.
  4. We maintain independence and autonomy.
  5. We share many core values, but are two very different people with different interests, so while we do some things together, we have no problem traveling solo or supporting each other’s endeavors.
  6. The time we spend together is quality time. We carve out date nights and little adventures. Novelty is exciting!
  7. We realize that a healthy relationship is give and give. I’ll never forget how he took care of me during my times of need, and I’m always thinking of ways to reciprocate.
  8. We do relationship check-ins as needed.
  9. We allow each other freedom to be romantic and sexual with other people. Every time we experience another person’s energy, it gives us a libido boost.

So, basically, we’ve rejected all the typical trappings of a long term relationship that can cause stress and resentment to build. People used to ask us, “When are you getting serious?”

Maybe I should have replied, “When are you getting playful?”

It’s much more fun to think – and play – outside the cage!

Planned Threesome

By Kendra Holliday | December 23, 2017

After our spontaneous threesome the other night, I was SO eager for the three of us to get together again! I’m so greedy! I want more more MORE!

Lana came over, and we sat on the back porch and talked over cocktails, relaxing and catching up.

After a while, he asked her if she was down to play that night, and she said yes!

I love her hazel eyes, her bountiful hair, and pert nose. I’m a sucker for pert noses! She has such animated facial expressions, and tells such funny stories. I love her mannerisms. Very mischievous eyes. Also, she has an extremely smooth butt. It’s like really cute butter.

This time, he drew a bubble bath for two! We both easily fit in the tub. He gave us our girl time to sit and talk. He checked in on us, brought us drinks, it was wonderful!

Then we sat on the couch for a while to cool down, the two of us naked with towels.

He led us up to the bedroom, which was bathed in the golden glow of a small, bedside lamp. The king-size bed was adorned with chocolate brown sheets. Mood music played softly in the background.

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Spontaneous Threesome

By Kendra Holliday | December 22, 2017

Continued from previous post

Me getting spanked by Matthew! Photo by Mike Estes

We arrived at Hustler’s Taboo night.

Thankfully, we were mature enough not to let anything interfere with our great evening, which is a good thing, because it got better every second…

Taboo was crowded and full of activity. They have quite a bit of equipment – a rope suspension section, couches, spanking benches, St. Andrews Crosses. All were in use, but soon a spanking bench opened up, and we seized it.

I went first so she could watch and get used to the energy of the place. She had some BDSM experience, but nothing public.

I eagerly bent over the bench. I was wearing a sexy little business top and skirt. The skirt hem was asymmetrical, so when I walked or bent over, you could see where my lace stockings met my pale thighs.

He worked me over, grabbing my hair, spanking me, lavishing me with good, hard attention.

I got hot and ripped off my top and bra. Lana glanced around surprised. They allow nudity here!

It was so stimulating and exhilarating! I kept laughing and giggling.

He pinned my arms behind my back and instructed Lana to tend to my top as he tended to my bottom. This guy parked himself right in front of me and stared hard. Not a problem, but he was a little too close for our comfort, so Lana stood at my head, providing a barrier between us. I’m sure he didn’t mind her ass in his face.

We were buzzed and happy.

Next, it was her turn. She had been smacked on the ass during sex, but never had a spanking like this.

(more…)

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