The Good
As a sex surrogate and sexplorer, I have a philosophy when it comes to people, places and things: Leave them better than you found them. That is always my goal. When I’m in bed with someone, I want them to feel amazing and very special. Despite my best intentions, however, it doesn’t always work out that way.
Virgin #1 was a 38-year-old man with a dismal track record in the bedroom. He went to bars to “pick up chicks,” but would shut down as soon as he got them home. He’d give them oral sex, all the while sweating bullets as he feared letting them down, which in his mind, he did. He counted on alcohol to cloud the evening, mumbling about “whiskey dick” as he sheepishly showed them the door. Finally, he decided enough was enough, and he sought professional help.
I spent a couple hours talking with him about his issues, which was one key to solving them. Having it all out in the open was a relief to him—it was good to be on the same page instead of hiding his insecurities like porn under the mattress.
We then spent a couple hours in a very open and honest setting—he felt safe and understood by me, which was such a contrast to his past experiences. He was getting to the point where he was feeling like women were adversaries, to be feared.
He had successful intercourse with me for the very first time. He was amazed—it felt so right and spectacular. “I can’t believe I’m doing it!” he kept muttering incredulously in my ear as he pushed awkwardly in and out of me.
The sessions he had with me were a breakthrough with him. He found that women are not scary creatures, and went out into the dating world with newfound confidence.
Virgin #2 was a charming 25-year-old with a perfectly charismatic personality. He was pursuing a career in politics, and wanted to be sure the time he spent with me remained under wraps, as he was very conscious of the potential for future scandals.
#2 had never kissed a girl. I was his first on all fronts—first kiss, first oral, first everything. He was so sweet, I asked him how this came to be, and he told me it was due to lack of opportunity, but that he had his eye on a special girl, and wanted to make sure he would be prepared for courtship.
It’s a good thing he went this route, as he was a terrible kisser. I patiently showed him how to relax his mouth and take his time. He went down on me and remarked, “I’ve always heard a woman tastes like fish, but that’s not true at all! You taste wonderful!” He completely freaked when I put my mouth on his penis, saying, “Okay, I’ve always heard a blowjob feels incredible, and that is absolutely true!” The cutest moment was when he got on top of me and started having sex with me.
“I had NO IDEA how much work sex is!” he huffed and puffed. He used pelvic muscles he never realized he had! It felt so great, TOO great; it took him forever to orgasm. He finally resorted to a more familiar method—masturbation as I quietly lay next to him.
Luckily, he started dating the girl of his dreams a month after our session, and he couldn’t thank me enough for giving him a great head start.
Virgin #1 was a 38-year-old man with a dismal track record in the bedroom. He went to bars to “pick up chicks,” but would shut down as soon as he got them home. He’d give them oral sex, all the while sweating bullets as he feared letting them down, which in his mind, he did. He counted on alcohol to cloud the evening, mumbling about “whiskey dick” as he sheepishly showed them the door. Finally, he decided enough was enough, and he sought professional help.
I spent a couple hours talking with him about his issues, which was one key to solving them. Having it all out in the open was a relief to him—it was good to be on the same page instead of hiding his insecurities like porn under the mattress.
We then spent a couple hours in a very open and honest setting—he felt safe and understood by me, which was such a contrast to his past experiences. He was getting to the point where he was feeling like women were adversaries, to be feared.
He had successful intercourse with me for the very first time. He was amazed—it felt so right and spectacular. “I can’t believe I’m doing it!” he kept muttering incredulously in my ear as he pushed awkwardly in and out of me.
The sessions he had with me were a breakthrough with him. He found that women are not scary creatures, and went out into the dating world with newfound confidence.
Virgin #2 was a charming 25-year-old with a perfectly charismatic personality. He was pursuing a career in politics, and wanted to be sure the time he spent with me remained under wraps, as he was very conscious of the potential for future scandals.
#2 had never kissed a girl. I was his first on all fronts—first kiss, first oral, first everything. He was so sweet, I asked him how this came to be, and he told me it was due to lack of opportunity, but that he had his eye on a special girl, and wanted to make sure he would be prepared for courtship.
It’s a good thing he went this route, as he was a terrible kisser. I patiently showed him how to relax his mouth and take his time. He went down on me and remarked, “I’ve always heard a woman tastes like fish, but that’s not true at all! You taste wonderful!” He completely freaked when I put my mouth on his penis, saying, “Okay, I’ve always heard a blowjob feels incredible, and that is absolutely true!” The cutest moment was when he got on top of me and started having sex with me.
“I had NO IDEA how much work sex is!” he huffed and puffed. He used pelvic muscles he never realized he had! It felt so great, TOO great; it took him forever to orgasm. He finally resorted to a more familiar method—masturbation as I quietly lay next to him.
Luckily, he started dating the girl of his dreams a month after our session, and he couldn’t thank me enough for giving him a great head start.
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.
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."
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.
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.
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.
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.
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.
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.