True Stories From A Real-Life Sex Surrogate

Adult virgins, people with disabilities, and guys who have had their penises numbed by porn are among her clients.

I don’t know what you picture a sex surrogate looking like, but Kendra Holliday probably isn’t it. Neither frumpy clinician nor stern dominatrix, Holliday, 43, is more like an eager puppy, wide-eyed, full of energy and prone to saying “Yay!”

A sex surrogate “help others overcome social and sexual issues through hands-on intimacy. It is intimate. It is therapeutic. It is not entertainment,” writes Holliday on her site Be Open and Honest. Surrogacy, kind of a therapy with benefits, occupies a somewhat gray area of the law—although it’s clearly for therapeutic purposes, everybody’s naked and fucking is often involved. Clients come to Holliday (um) via web site or are referred by other therapists.

Holliday is passionate about her work and dives right in with every client, sometimes to the point of (her own) orgasm. (“It’s not my goal but it usually happens because I’m a responsive person. It’s just a bonus,” she says.) She’s taught adult virgins how to kiss, masturbated with a 60-year-old woman, and taught many men how a woman’s body looks and operates by spreading her legs and giving them a hands-on tour.

Holliday’s “yay sex!” activism permeates her life. She’s co-founder of Sex Positive St. Louis and an Alternative Lifestyle Advisor and Gynecological Teaching Associate for Washington University School of Medicine. She’s in a polyamorous open relationship with long-time partner, Matthew, and attends school board meetings with her activist teenage daughter “Thorn” to make sure the Sex Ed actually contains some Ed.

Jill Hamilton: How did you get into sex surrogacy?

Kendra Holliday: I started out doing regular escorting with an ad on Craig’s List. It was fun but I noticed I gravitated toward the men who weren’t just in it for the entertainment but because they had some sort of sexual issue, a fetish, or a disability. Some men would cry or talk about having ED [erectile dysfunction]. When I worked with them it felt very rewarding, and it sort of morphed into more of a therapeutic hands-on intimacy.

JH: What are the most common things you see?

Holliday: Men are really, really, really concerned about their penises and how they should be behaving. There are a lot of people dealing with ED. Anxiety is the number one boner killer—the more you think about not getting hard, the worse it gets. I try to find ways to try and work around the anxiety and manage it. Some guys think if they get a hard-on, it’s supposed to last for 20 minutes, but hard-ons come and go. We’ll try to go with the flow and recognize what sort of things cause it to wane.

I also see a lot of people with disabilities. They have a limited access to all the dating and practice that a lot of us take for granted. They contact me to get the experience that they need so they can know how to work with what they’ve got. It’s really exciting for them to find ways to pleasure a woman when they have limited mobility.

And there are a lot of adult virgins. Mostly they’re in their 20s and 30s but the oldest adult virgin I had was 62. I kind of train them, teaching them that a woman’s body is more than just boobs and pussy. It’s so fun to watch them enter a woman for the first time and they’re like “Whoa!” Some of them are like “I didn’t know that thrusting was this much work!”

JH: How do these men end up virgins?

Holliday: A lot have Aspergers or social awkwardness. It can be quite debilitating because they’re horny and want to do things, but they don’t know how to interact with people. I get to teach them about how to approach women, how to recognize the signs of flirting, and how to kind of smooth things along.

JH: How do you help the ED guys?

Holliday: Some guys need a magic feather like Dumbo. Even a candle lighting ritual can help them get over the hump. If they can just get one or two successes, they get on the right track to not being so hung up about it. I love finding creative ways through their different situations and trying different techniques.

Another super important thing I’m finding now are men of all ages who have had their dicks numbed by porn and having the same routine. Since they don’t have a partner, they masturbate to porn every day and mess themselves up getting porn dick. When they get with a live woman, they’re stumped. They need to manage their porn consumption or take a break all together. And I definitely recommend they don’t masturbate the same way all the time. You have to mix it up or you’ll get stuck in that pattern. Try lying down, in the shower, use your imagination.

JH: Plus there’s a lot of bad technique in porn.

Holliday: Oh my god, I know! It’s so stupid, like that leg position that’s trying to make it clear for the camera. And they’re not even touching except for the genitals. I teach my clients that sex is whole body touching—the more contact the better.

JH: Ever repulsed by anyone?

Holliday: I always find something attractive about them. Maybe I’m not ideal either but here we are together, working together! I had a schizophrenic guy who drooled a lot, which was gross to me, but I focused on something I did like. I could look in his eyes and say “You have beautiful eyes.” I always make sure to compliment the person on different things they have going for them—I make sure they know about any assets they have. That’s part of the process. We also do body show-and-tell.

JH: What’s body show-and-tell?

Holliday: It’s such a good practice. Everyone should do it! I start with me undressing—that’s a good ice breaker. I start from the top of my head and talk about my hair and what I think about it, then my eyes, and all the way down into my waist. Then I say “OK, your turn” and they show me things. I ask them questions like “Tell me about that scar.” It conjures up relevant memories that are really therapeutic. You wouldn’t think they’re connected but they are. There are so many stories in the body.

Then I totally spread my legs and show them. I say, “Get down here, use my flashlight.” They don’t get to see real live pussy sometimes so it’s nice to say, “This is what mine looks like.” Some men really don’t know where the clitoris is located, so I show them the anatomy and let them know that each woman has the same parts but maybe just arranged a little differently, bigger or smaller or whatever. These basic tips can make a huge difference.

JH: How do you redirect someone who doesn’t seem to be on the right track?

Holliday: When you’re dating normally, it’s your initial inclination to avoid those sensitive topics, but we have a built-in platform where I can say it. There was one guy who would latch onto my lower lip and suck on it like a fish hook. He kept doing it, and I finally said “Break the seal here, let’s back up a little bit and I’m going to show you.” You just have to say it! I’m doing it for the people they’re gonna be with. For God’s sake, it’s the least I can do.

JH: Do couples come very much?

Holliday: Not very many, but I have some. I had a couple who had been married 20 years but were nearing divorce because of an issue in the bedroom. She couldn’t give her husband oral sex the way he liked it—before, she always came at it with this mechanical, clinical kind of approach. I taught her about changing her intentions and noticing the sensuality of it. “Do you love your husband? His cock is an extension of him.” All she had to do was shift her mindset. And it worked—it totally worked. Yay! Just because of that.

JH: What about this does it for you?

Holliday: People can spend years in talk therapy, which is fine, but I like that you can get a lot more accomplished in three or four hands-on sessions. And it’s so nice and loving! There are so many emotions that come into play and it can also be very sacred. There was one man who had muscular dystrophy and after we had our sexy time, I laid myself on top of him. He said it was the first time he’d felt someone else’s breath and heartbeat before. It was incredibly moving. Some people don’t even know what that connection feels like and when they do, it’s just a beautiful thing.

Jill Hamilton writes In Bed With Married Women( Follow her on Twitter @Jill_Hamilton.

This originally appeared on Alternet. Republished here with permission.

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