A
female
age
30-35,
anonymous
writes:So I've been seeing this guy for a while. I had known him before, but now we are really connected. So we went out last night to chat under the stars, and I ended up finding out he was a virgin. I was shocked but totally cool with it. I'm pretty sure I'm going to be the one who leads him through his whole sexual experience. My questions begin with how can I raise his self-confidence? He's been broken down. How can I help make his fist time meaningful? He's afraid it won't be good. I've shared my wealth of knowledge, but I feel like I need some back up here! Reply to this Question
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male
reader, thruxton +, writes (1 February 2011):
 who cares if the 1st time is good? why not plan on giving him 2 orgasms? and then go at it again the next day. this isn't a romance novel. a guy will appreciate your body and enjoy learning.
A
male
reader, anonymous, writes (1 September 2008): I am a 25yr old male virgin, ill save you the sob story but rest assured its a a painful fact. I cant really offer any practical advice but... tell him how much you care about him and how much he can trust you. Take the lead initially. He is a lucky guy.
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A
male
reader, daletom +, writes (28 August 2008):
A female reader, anonymous, writes (27 August 2008):
"Wow, thanks for the novel, daletom. I'll get right on
reading that when I can clear a whole two hours of my day."
Is he worth two hours, if it might help you do something that makes it very special to him?
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A
female
reader, anonymous, writes (27 August 2008): Wow, thanks for the novel, daletom. I'll get right on reading that when I can clear a whole two hours of my day.
Thanks for your advice everyone.
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A
male
reader, Ivanhoe93 +, writes (25 August 2008):
 My first time was with someone with way more experience than me, and they made it great for me. Don't expect him to know to much of what he is doing let him have the lead but help him with out him asking.. Most guys hate not knowing what they are doing deffinitly take that into consideration. After the ball gets rolling just guide him and go with the flow...
Best wishes
God Bless
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A
male
reader, daletom +, writes (22 August 2008):
Why were you "shocked" to learn he is a virgin? Do you love each other, or is this step something you're doing because "everybody is having sex" (that's NOT true!), or maybe he's simply curious about it?
Have you considered that maybe he's a virgin because he values and respects his sexuality? (Well, maybe he's a virgin because he was locked in the basement of a monastery for the last 6 - 8 years.) Of course, this places you in a position to either validate these feelings, or do significant emotional damage to him.
In spite of what the culture says, I don't think it's true that "the first time doesn't mean as much to guys". It means just as much - though perhaps in different ways.
Well, I'm a male guy person of the masculine sex who gave my virginity to a woman I loved - but only once, so I don't have a LOT of experience at losing my virginity! On the other hand, it happened when I was 23 so I may be different from your guy's situation. Maybe that's why this post seems to be as long as a whole book. For the record, my first experience is in the thread "I'm a virgin and worried about my wedding night...", at http://www.dearcupid.org/question/im-a-virgin-and-worried-about-my-wedding.html . Even though it was lousy sex, it was still very significant and meaningful to us!
You have already figured out one significant thing: His virginity is a private, very personal thing to him. And, while I suspect he is looking forward to changing the situation, he isn't ashamed of it. It's certainly nothing to be ashamed about. But - obviously he values his sexuality. He almost certainly could have had sex 5 years ago, maybe even 10, if all he wanted was to masturbate inside a vagina.
I trust you have similar values, and see this as more than a physiological interaction between the two of you. Are you ready for him to become very attached to you? Has the concept of "life partners" crossed your minds as a possibility, even if that level of commitment isn't there yet? What I'm trying to impress on you is that there are emotional and spiritual aspects as well as the physical, and this young man puts some significance in the emotional and spiritual factors. Please respect that - and thank you, if you have already figured that out and agree with his beliefs.
If your guy is like me, he is as concerned with pleasuring you as he is with his own enjoyment. Your prior history concerns him at least a little. (I had something of an advantage there, since my first partner was also a virgin and bringing her to her first orgasm was as significant as sharing our first intercourse together. No, those 2 events didn't happen together.) So I'd say you need to make sure he knows that he DOES pleasure you. Has your lovemaking progressed to petting and oral sex yet? Have you - matter-of-factly, perhaps without his even realizing it - started teaching him how to make love with you? Work to increase his skill, without over-praising a fumbling performance and definitely DO NOT fake anything!
If you do a good job of building his confidence the "comparison" problem may even vanish. It can get to the point where both of you can say things like, "Yeah, Bob" (or, in his case, "Sue") "was a good kisser but nobody can do 'Spider Legs' as good as you!". But that's probably a goal for the future . . .
At an intellectual level it hadn't registered with me that first-times were almost never "great sex". Somehow I expected ours would be "fabulous". After all, we were in love, and just doing the natural thing, and we had been working up to it for most of a year. The truth is, it was lousy sex, and - one of the most significant and meaningful things in our lives. How was it for you? Hollywood and Madison Avenue have almost certainly created unreasonable expectations for your guy. You don't have to splatter any mental graffiti on his romantic images but the physical reality may not meet his expectations. I hope you are a partner who teaches him (he doesn't know yet!) that there's more to the experience than the physical reality.
As for the mechanics, you know him better than I. Probably the most important advice is to know how much he wants to do on his own, and how much he'll allow (or even better, WANT) you to coach him. You probably understand that making love is something you do WITH somebody more than TO somebody but in his mind this idea is probably corrupted by some macho folklore and notions of how things are "supposed" to happen.
Although I knew the time (within a few hours), several months in advance, when I would lose my virginity - I think it would have gone better with more spontaneity and less planning. Although guys are socially programmed to be the aggressor who "takes" a woman, it is AWESOME when a woman says (literally or figuratively) "I want you!" or "Make love to me.". So if he wants to be totally in control of time and place, that's fine - but don't be afraid to take the initiative.
Speaking of time and place I hope you allow plenty of time for the whole process. At least an entire overnight - a whole weekend would be even better. And of course, total privacy and access to toilet facilities. Popular stereotypes aside, it's not something to be done in the backseat of a car, or while your roommate runs out for cigarettes.
Keep it fun! This will be a significant event that he'll remember forever, but don't let it be somber, solemn, or overly serious. Even if you plan it to the point of "on the evening of some particular day we are going to have sex", make room for other enjoyable activities. A ballgame - concert - a couple hours in the art museum. Something you can do together, and have some interaction while doing it. Perhaps you'll just skip the activity entirely, but having it available can dissipate some of the awkwardness.
Alcohol is generally a poor sexual lubricant, and this situation is no exception. If he is truly shy and awkward, ONE beer or ONE glass of wine might be helpful but definitely no more.
You know what the first coupling will be like. There are probably credible statistics published someplace on the 'net, but it breaks down roughly like this: 97% of all guys climax too quickly on their first time, while 2% lose their erection and can't finish - or even insert. You're already smart enough not to call attention to either situation. There WILL be a second time - perhaps after taking a walk, or seeing that ballgame, or even sooner. I hope you will be able to sincerely tell him how special it is (to you) that you were his first, regardless of how it goes.
What about the other 1% of guys? I suspect they have considerate, understanding partners who help them to a preliminary orgasm before they even try penetration. The guy probably needs to know it's going to happen that way, and not resist when she uses her mouth or hands early in the foreplay. Then, after he has had time to re-charge (probably 5 to 15 minutes), he will have better control and last longer. If it's really important to him that he lasts as long as possible (almost certainly because he wants to please YOU), put him on his back for the first time.
The first time I tried to enter a girl, I couldn't get the location or angle right. OK, make jokes about that, but it HURT to be jammed up against the wrong place. Now I find it rather erotic to feel my partner gently guide me to the opening, but I don't know if I would have thought so then.
The first time a woman's vagina enveloped my penis was an incredible sensation! To be honest, I pretty much lost control and couldn't imagine that my partner was feeling anything less exquisite. In fact, she was a virgin girl and I hurt her much more than necessary. An experienced partner may have found my reaction mentally and physically stimulating, or at least cute. Hopefully she wouldn't be disappointed at the brevity, nor think my inept fumbling was disgusting.
As he finishes twitching, and afterwards, it's hard to say how he'll feel. He may not even know himself. Ecstacy - disappointment - pride - embarassment - exhaustion - hyperactivity - giddy chattering - stone silence. Perhaps display, explore and revel in your mutual nakedness - or cover-up and dress as soon as possible. He might cling to you, or need some time to himself. In those moments he may be more emotionally naked and vulnerable than any other time in his life. After my first time, I certainly felt differently about myself, and my lover - and not in a bad way! We cuddled for a while, then went for some desert and talked about what had just happened. Then we did it again - and it was about 1000% better.
(Both my wife and I like to stay coupled and cuddle after sex. Unless she's on her period, cleaning up can wait for a less intimate time - even the next day. Others, both men and women, have a compulsion to jump up and wash even before the contractions are done. He might have some idea about which is the "proper" thing to do. If this conflicts with what he - or you - actually feels like doing you have an opportunity to graciously and lovingly resolve the difference.)
My lover and I slept together after our first time. (OK - it was actually the 2nd time. But you know what I mean.) Neither of us was accustomed to sharing a bed, and I didn't sleep well, so I was a little crabby the next morning. That didn't keep us from the 3rd time. I don't think I'd do it differently if we could do it over, and if your guy is like me you can expect a lot of sex in a short time!
I wish we had used some little ceremony or ritual to mark the occasion. Her parents are tea-totallers so producing a hidden bottle of champagne wasn't a viable option. Maybe just giving a flower - symbolic of being de-flowered - or some little trinket gift. (No, not your panties!) Maybe something that could be placed on an office desk, or attached to a keychain, as a reminder. I know one couple who carefully saved the LP record album (boy does that show my age!) that played while they first made love, and bring it out on special occasions . . .
One final point must be mentioned. I hope you two can responsibly find a way to enjoy natural, naked genital sex. Contraception and STD's are VERY REAL problems that you MUST face but "condoms" is NOT the only solution, and perhaps not even an effective solution in this instance. Quite aside from their effect on the physical sensations, for both of you, they upset the flow of lovemaking. That's not a good thing for a nervous, inexperienced guy. More importantly he is too likely to use a condom incorrectly, eliminating all the safety and protection it's expected to provide. In those critical moments at the end, when everything in him might be urging him to stay connected and sort out a whole spectrum of unfamiliar feelings and sensations, you could be urging him to withdraw and clean up properly. Eventually you can teach him to do that, but it's a lot to learn and do correctly on the first time.
Yes, what I'm suggesting means you'll need to have a conversation about sexual exclusivity. And find ways to verify each other's health status. I suspect you two are mature enough to do this.
And I wish, for both of you, not only mattress-thrashing, scream-into-the-pillow orgasms but also the most intimate, relational sex that two soul-mates can experience.
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A
male
reader, LonelyButNotAlone +, writes (22 August 2008):
 I think as long as you are understanding that it might be a little strange and surreal for him and give him a little guidance if he's having trouble, everything will be fine.
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