Sheri's answers made me think of my own experiences with ushering boys into men. Or something like that. I figured I'd just ramble on about that for a while.
The worst virgin I ever had was still better than the worst sex I've ever had. I don't hold it against virgins, even if they've got some experience in other arenas. Usually they're so eager that's it's tough to be good. I'm speaking of guys exclusively here; gals are a different matter.
I've had more than one premature ejaculation, which is why I usually warm things up orally first, because once the rocks are off to start, they usually have more staying power the second time. But sometimes you want that first spurt to be inside you, and it doesn't work out. I had a boy cum in his pants just kissing me once. It was awkward for him, but I just shrugged it off.
I think that's the key to properly introduce a virgin to sex: you've got to be generous. It's not necessarily going to be the longest or the greatest, but it's an honor, at least as far as I'm concerned. I compliment and give pointers. As I've gotten older, I've gotten better at it. When I was younger, the virgins were thicker on the ground and they were usually a bit more selfish too, for some reason.
Taking a guy's virginity has a different feel when you're roughly the same age. Even when I was pretty experienced, there were still plenty of partners who'd never done it before, and sometimes they wouldn't tell me, but you can sort of tell. I'm not saying you can always tell, and sometimes it's hard to say whether they're really virgins or just have only done it once and probably with someone who had no idea what they were doing either. These days, the few I've had have been either more willing to admit it or have come to me specifically because of it.
And there's absolutely not shame in virginity. Really. Whether you're saving yourself for marriage or just haven't had the opportunity or just haven't felt like it, there's no shame there. A lot of people feel ashamed of it but I think it's often more shame about something else. I mean, if you've wanted to have sex but no one has accepted your offer, you start to wonder if something's wrong with you. Or you might be ashamed of breaking whatever vow you've made to stay a virgin. But you shouldn't feel ashamed of being a virgin. Whether you're 13 or 43, sex is fun, but it's not all there is in life, and not having had sex, even if you've masturbated millions of times, isn't shameful.
I've had a few virgins who were breaking promises. I find that, frequently, those promises were promises they made because they felt they had to, not because they really wanted to. Parents, schools, religion, and even just society seem to make it out that virgins are pure and people who have sex are sullied in some way. So just as there's no shame in being a virgin, so too there's no shame in losing your virginity.
I've been happy to offer myself as a way for virgins to switch from one state to the other. I'll do it again, I'm sure. I'll probably be ancient and still available for virgins, if they'll have me. But it doesn't make you a man to have sex either. It's this social rite of passage, but that's silly. Sex is something you do because it's fun or you love someone or for various other reasons including procreation. But being a man (or a woman, although I'm not really talking about them here) is how you act, not what parts of you have contacted what parts of another person.
I've been the first girl for a few gay guys. Maybe I should say bi guys. Some of them were bi, and cheerfully had sex with both women and men, but some were just curious, had sex with me, and then went back to having sex with men. Curiosity is healthy.
Let's see... the oldest virgin I've ever had was in his thirties, I believe. But maybe that was just the greatest difference in ages. He was deeply ashamed of it. It twisted him up inside. I felt more like a therapist than anything else. I'm not sure how much I helped him, because he was convinced that he was terrible in bed, kept apologizing. I think, although I'm not sure, that part of the reason he was still a virgin when I met him was that he wasn't attracted to women his own age. Which is also kind of sad. I feel for people who are only attracted to things they can't have. Yes, this means I have sympathy for pedophiles. There are a fair number of them living among us, and most of them would never hurt a fly. It's just how they're wired. I'm not defending them doing anything about their urges, but it must be difficult to be that way.
Some tips for any virgins in the audience:
Grateful is great, but don't feel like you have to overdo it. Even if I were doing you a favor (and I'm not always; sometimes I just want to get laid and you happened to be a virgin) you don't have to be any more grateful than you should be if anyone has sex with you at any time.
Express your gratitude in actions, not words. Telling me you're grateful is fine, I guess, but even better is being a considerate lover.
If you can't last, there are other things we can do. It doesn't have to be a one-time thing. Sex is more than just pumping for five seconds, rolling over, and going to sleep. I'm not saying that to shame you either. I'm saying that because if you can't last, lots of the other stuff can be a whole lot of fun too. Enjoy yourself. Don't be in a hurry to lose it.
This is a tip for everyone, but listen to your partner. If she (or he) knows you're a virgin, hopefully she'll tell you what to do a bit more than normal.
Sure, getting your dick wet the first time is great. But what's even better is making someone else happy sexually for the first time. That's why sex is better than masturbation. Getting yourself off is something you've probably done before, but getting another person off... that'll make you feel like a million bucks.
Porn lies. I love porn, but don't believe it for a moment. Real sex isn't like that. It's way, way better. Being surrounded by a living, warm, wet, breathing human... yeah, there's no shame in going off too soon if all you've ever done is stroke your cock with your hand. I don't have a cock, but the first time I stuck my finger in a pussy, you can bet I knew that a real pussy is different.
Some tips for anyone who finds themselves deflowering someone:
Slowly. They may want to rush, but slow it down. Make it an experience, not just a moment. That's really the best thing you can do.
Get naked with them. Sure, the back of a car or an alley or a dark closet is sexy, but the first time, maybe try to do it up proper.
Don't worry about them being quick on the draw. Again, this is addressed to those who are making a boy a man. If a gal is quick on the draw, that's great and keep going. But if a male virgin goes off too soon, like I was saying to them, there's always round two.
Don't be surprised if they can't get off. This is an odd one, but it's true: sometimes the nerves and the buildup are so much that even the most hot-to-trot virgin can't keep it up. Keep at it. Explore other things. Make them feel good, even if you can't get them off. They'll remember their first time inside you whether it was orgasmic or not, I promise, if you make it good for them.
And lastly, you should be grateful too. They're giving you a gift. Yes, there's too much baggage on that gift, but even without it, they've picked you to be their first. And that's special.
Yeah, that's about it. Any questions? I'm on Twitter, email, and I would be on Facebook were it not for the fact that Facebook is a wretched hive of scum and villainy. Please, drop me a line. I'm dying to answer questions.
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