Heartwarming Update

By Kendra Holliday | November 19, 2012

This painting resembles my date the other night

On Friday I posted about my experiences with virgins. You’ll recall that Virgin #3 ended up hurt after our brief encounter. I felt so terrible about that, as it was the opposite of my intentions. I hoped that by being with him, I would turn the magic key that unlocked the door to his new and wonderful sexual journey.

Instead, he remained closed off and cynical. Still, we remained friends, and I watched in frustration as women continued to overlook him. They didn’t realize how much he had to offer. It was like I was the only person in the world privy to his superpowers!

Over the past couple years, I was tempted to ask him to have sex with me again (he’s such a good lover!), but I didn’t want to rock the boat and make things worse.

Finally, last week he emailed me asking if I wanted to go see the new movie about sex surrogacy called The Sessions with him. It felt like as good a time as any to broach the subject.

I emailed him back asking if he wanted to make a date out of it, complete with dinner and sex. I made sure I was clear that I was open to anything with him that evening, even not having sex.

To my delight, he accepted my offer in a level-headed, mature manner.

On the night of our date, as soon as I answered the door I could tell he was a different man. Previously, he came off as dark and cynical, but now I could tell there was something very positive and openhearted about him. His demeanor, the look in his eyes, the bounce in his step…

We were matching in our classy grey and black outfits – I wore a dress and boots and he had on a sleek button-down shirt, sport jacket, dress slacks and black polished shoes. Very handsome and dashing.

He opened the car door for me. He drove us to a romantic Indian restaurant. He pulled out my chair for me. We had lively conversation; he regaled me with humorous stories and his observations on human nature. He was relaxed and comfortable, which put me at ease. Everything felt very natural.

The movie theater was located in an upscale mall, replete with twinkling lights and cashmere galore.

The movie was wonderful, heartwarming, inspiring. Right before it started, he – surprise! – pulled out a bottle of red wine and two glasses and served us. During it, he put his arm around me and I stroked his elegant hand.

After the movie, we went back to my place. It blew my mind to think that I was the only woman he has ever been with. He’s a naturally good lover, knows how to treat a woman, and is handsome and capable. And here he was, about to experience it all, up close and personal.

He took control, kissing me on the couch. It was so nice to reconnect! Then we retired to the bedroom and slowly undressed each other. We went down on each other and he practically came when I sucked his cock, but he held back. I sure didn’t when he put his mouth on my pussy though!

I put a condom on him (it was strictly for his safety, as there was no concern on my end regarding STIs or pregnancy) and we had sex. It was wonderful! We ended up doggy style, and when he came, he grabbed me so tight!

It was a truly amazing evening. He perfectly captured what women like me want – to be treated like a Queen, but also ravished in the bedroom.

The next day, he sent me this incredible message:

Last night in the bedroom was as close to a religious experience as I have ever had. Our encounter reached my mind in a way that my therapist could not offer and I really think I had a breakthrough.

I felt incredibly comfortable with you, felt sexy, I really wanted to care for you, to take control.  The make out session on the couch was sensual, the foreplay and oral was wonderful, the sex intense. As I thrust deep inside you, a feeling came over me at that moment, you were not a fuck toy, not a masturbation sleeve, but a feminine woman whose warmth, energy and soul I could feel.

And in return, I lost control and had a primal need to thrust deep inside you, to explode and give you my essence. I don’t always feel much like a male in control of my own world, but as we came down from the world, sweaty and you lay in my arms, that moment I truly felt like a man.

And perhaps one more fortunate than I give credit for. Yes, the amount of times I experience this is counted in years rather than days, something that would drive any average person completely crazy.

But on the other hand, I easily could have found someone when I was younger, and likely the sex would be routine and I would eventually have my heart broken, still not understanding shit.

I certainly would have never reached the level of understanding I did last night. I feel so sorry for the people who, despite getting laid on a frequent basis, will never experience these things and not enjoying or appreciating one another, but simply trying to get off. They’re having sex, but they’re NOT having sex, if you know what I mean.

And despite how intense last night was alone, I can’t even fathom how more intense it would be to have this experience with a woman whom I loved with all my heart.

I think what I’m trying to say for one is that I understand ‘you’ and why you do what you do. I’m a cynical non-believer skeptic, but everything made logical sense last night. I BELIEVE in sex. I’m starting to think that when our clothes come off, we reveal who we truly are.

I always thought I wanted a woman in my life to make me happy. And there’s still truth in that, but after last night, I don’t think that’s quite it. Instead, what I think I really want is to bring a special woman into my life in order to make HER happy.

Photo by Stan Strembicki

In the way you shared your goddess essence with me, I want to take her, ravish her and give her the gift of my energy. To show her something beyond what any typical guy looking to get laid can’t ever offer her. To open her mind, to touch her soul and make her a goddess.

Who can say what the days will bring. But know this: don’t worry for me. Maybe I didn’t realize it back then when you took my virginity, but last night made it clear now: you definitely left me better than you found me.

And more importantly…I hope I left YOU better than I found you, Goddess Kendra Holliday.

SIGH. Isn’t that just wonderful? I feel like we’ve come full circle. I feel redemption. And I feel very happy for the next woman he’s with. To whoever that is: he’s going to treat you right!



rarry 2012-11-19 08:25:39

A beautiful letter. I’ve never before heard of a circumstance like this, where one person becomes fixated on the other but it isn’t mutual, working out for the better for both of them. I hope his current emotions about it are stable and we can call it a happy ending, without the ending.

I also don’t know of another person, male or female, who would have made that extra effort. I’m a skeptic and unbeliever myself, and I’m impressed. Amazing work, Kendra.


    The Paramour 2012-11-19 23:44:37

    I am the other person in the story. Yes, unique circumstance, but I think level heads and open minds can make things work even in the most unusual of situations. As for me, I’m doing just fine: slightly bummed but only in the way someone is when they’ve returned to work from a vacation or break. But glad I had an excellent Holliday. 🙂


Matthew 2012-11-19 10:36:48

This is one of my favorite posts to date!!


Brad B 2012-11-19 14:06:06

Smile on face


WD 2012-11-19 17:19:21

What a fitting tribute to the life and work of the other goddess — Dr. Cheryl T. Cohen Greene. You both exhibit such care, loving and healing energy, and orgasmic joy. Blessings to you both. And thanks for sharing a story that embraces the notion of “don’t ever give up”.


    Kendra Holliday 2012-11-19 19:12:34

    I got the book featuring Cheryl Cohen Greene in the mail today. Now I just need to find time to read it!


      WD 2012-11-21 17:49:16

      Got my copy, today… pictures of Cheryl and family was an unexpected bonus. Enjoy, Surrogate Kendra. Cheers,


singleexpat 2012-11-20 04:11:15

Lucky guy…


cunexttuesdayreads 2012-11-20 22:09:00

Woah… good story!

-Beatrice Freed


Theory of Potential 2012-11-25 01:37:56

The Paramour, this may seem crazy but I would love to speak with you more. I’m one of those awkward, nose in a book types. Perhaps too open minded for my own good, if your interested, theoryofpotential@gmail. I havent been able to hop on here in a while but its great to see that a community exists here, I wish we could all come out in the day light.


icEquEEn 2012-12-06 00:41:04

Love this site, and this story touched me so deeply, I have not had an experience like this but hope to one day.


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