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Diary of a Sex Surrogate: The Devirginizer

Diary of a Sex Surrogate: The Devirginizer
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Not every woman in their late 30s can say they devirginized four men in one year. I can. Over the course of several months, I spent intimate time with four adult male virgins, from 24 to 38 years of age. Two had overwhelmingly positive outcomes, and two did not.

  The Bad

Virgin #3 was a 30-year-old man who had also never kissed a woman. He was completely handsome and stylish, but very socially awkward. We went on three dates before doing the deed, and he was by far the most talented lover out of all of them. As we made love, he was simultaneously thrilled and horrified at how incredible sex felt. I was riding him, my hair streaming down my breasts, and he lamented mid-thrust, “I can’t believe I’ve been missing out on this for TWENTY YEARS!” Such a bittersweet moment.

I was so happy for him, and was glad to help prime his pump so he could go out and knock ’em dead. But afterward, he started asking me out on more dates and even proposed a camping trip. I gently but firmly reminded him of the boundaries set in place ahead of time, and he was crushed. It’s been a year, and he still hasn’t dated or been with anyone but me.

Virgin #4 was a 24-year-old man who was painfully shy and inexperienced. Incredibly naïve, he had had his heart broken by more than one catty cyberchick, and he needed some TLC.

I gave it to him. We got together a few times, took baby steps, and finally consummated the relationship. He was like a deer in headlights, stunned at the feelings he had never tapped into before. He found partnersex to be overwhelming, and couldn’t orgasm with me. He got ME to come though, perfecting his oral skills and being an apt pupil indeed. Have you ever been licked by a young, handsome virgin? I highly recommend it. And then he became attached to me.

When I let him know that our time together had run its course, he became very bitter and felt slighted. He even accused me of using him. A couple months later, he started dating a girl more his age, and that went well for about four months until she completely shattered him by cheating on him and then dumping him for the next shiny new guy.

  The Ugly (Truth)

There are consequences to your actions. Both the men who slept with me and I knew the risks involved with getting too intimate. We are all grown people, and we all have emotions. Despite our best efforts, some feelings were hurt instead of helped. I cautioned each of them ahead of time to be prepared for the unexpected. I feel terrible for those who left with a bad taste in their mouth.

But that’s the price you pay when you play with others—for every amazing sensation, there’s a chance for disappointment. For every euphoric moment, there’s heartache around the corner. Pride, regret, guilt, joy… It’s all these feelings that make us humans, and I wouldn’t want it any other way.

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Comments

Taking virginity is a tricky thing, isn't it? I've taken 2 (well, 3, but I didn't find out that the third had been a virgin until 5 years later!). One was great, one was awful. The great one was my first long-term boyfriend, and we were each other's firsts. The second? I was 20, he was 21, and he got way too emotional and attached and it wasn't good.

I find the conversation especially interesting when we talk about taking guys' virginities. People stereotype women as emotional, and as saving it for "someone special," and expect women to get attached. But guys are often stereotyped as just wanted to get laid, when in actuality, sex is emotional for many of them, too. Especially the first time.

I have a friend (27), who is seeing a girl (22) that is a virgin. He doesn't want to get serious with her, but wants to sleep with her. I've tried to explain that, in most cases, there's gonna be an attachment to the person you lose your virginity to. You've never done those things with someone before, so it's going to feel more intimate and create feelings you've never felt. For men AND women, yet we often forget that.

02/22/2010

Great comment! I had a tagline to this piece that didn't make the cut:

"I didn't TAKE their virginity. I gifted them with ME."

02/22/2010

Very interesting. I myself have never been with unexperienced men. Well in theory, I have not, but in practice, they really needed to learn a few handy skills.
Love the tagline. Smile

02/24/2010

I took my husband's virginity and he took mine. We have been married 7 years and have never been with anyone else. Men are just as needy as women even though they deny it.

02/26/2010

What a fascinating minefield. So much responsibility.... I don't believe I've ever taken anyone's virginity (and in sorting through the ashes of lovers past, so to speak, I do think I'd have been privy had that been the case), though I have been thanked after the fact for giving two their first "taste" of another high-value sex act, along with proper instruction that I was told served them very well with subsequent partners. Leave them better than you found them, indeed. Really interesting post.

02/28/2010
peterbilt_47  

I don't know, TBK, I'd call the ones you file under "bad" experiences good experiences, too. A man who comes to you for these reasons does so because he's got a lot to learn. Learning to separate is one of those lessons. They may sting for awhile, and I'm sure it's hard for you, in its way, to have to hold the line, but if they're open to learning it, it's a great lesson they've just been taught.

03/07/2010

I avoid virgins at this point, and being a guy's second is almost as bad (or worse, if his first was an insensitive nymphomaniac bitch) as being his first. I am not quite patient enough (it's a lot of responsibility to be someone's first, regardless of age or sex or gender), and I don't like hurting people, so now when a virgin comes my way, I run in the other direction, for his own good. I will, however, take a non-virgin male's anal virginity any day of the week (I have taken three or four now). Peculiarly, that one is not hard to handle at all. I can spot a guy who will be into it pretty easily, and I know how to ease his worries about the subject, shockingly, without having to let him put anything in my butt in exchange. Every man whose anal virginity I have taken has walked away fundamentally changed for the better, although one seemed to have become addicted, which I suppose could be troublesome.

04/15/2010
Clairest  

On the flipside, it can be tricky to be an older virgin who want to lose one's virginity when your potential partners freak out and bail before hand, expecting that you will be clingy afterward. I lost my virginity at age 31 and he freaked out, worried that I would be clingy, and bailed afterward. I had no intention to be clingy. I was pretty grounded in my life at the time and was not looking for some attachment to complete me. I was not in love with him and he did not seem more alluring or interesting afterward. I was looking for someone fun to date and sleep with. Simple. He made it complicated. I was over it quickly and moved on. As Kendra's post shows, there is diversity amongst virgins and how they react. Not all will be too emotional and attached.
Madshnoodles, what signs indicate a guy would enjoy pegging? Inquiring minds want to know.

01/10/2011

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