A
male
age
36-40,
anonymous
writes:Hi DearCupid,I'm 23 and a virgin.Basically, my question is how can I make my first time having sex an enjoyable one, or at least partially enjoyable?You seem to hear that everyone's first time is a disaster, awkward, or embarrassing, so how can I minimise that to at least make it some way enjoyable? I met a girl who I really like, and we have been going out for a few weeks. I know it's early days, but any advice on how to make sex at least partially successful first time would be welcome.Thanks Reply to this Question
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male
reader, previasc96 +, writes (13 August 2008):
lots of foreplay, lube, and patients
A
male
reader, daletom +, writes (1 August 2008):
OK, I think you were sincere when you asked the question so grab a Pepsi and settle in. After being disappointed and ashamed of my performance the first time I had sex, I did a lot of reading and some counseling on what I should have done differently. I'll never put the knowledge to use, but I can pass it on to others. Here's everything I can say that may be useful to you.
I think I understand some of your un-spoken questions because I was also a virgin at 23. I recall sitting in my college graduation, watching my friends as their names were called, and thinking "I'm probably the only guy here who hasn't been laid.". Well, it wasn't true then and it's not true now but it would be another 5 years before I knew that.
In our culture, being a virgin at 23 almost certainly reflects standards and expectations you have set for yourself. Unless you were locked in the basement of a monastery for the last decade you have had opportunities, or could have made opportunities, to just have sex. But you value sex (correctly, I believe) as something more than simply masturbating into a girl's vagina. That fact may be significant for thinking about your first sexual experience: there are mental and emotional dimensions to sex as well as the physiological. I hope your partner similarly respects and appreciates your situation, and feels truly honored to be your first.
Hollywood and Madison Avenue have almost certainly created unreasonable expectations in your mind, and not just because they concentrate on the physical and even deny that mental and emotional factors exist. At an intellectual level it hadn't registered with me that first-times were almost never "great sex". Somehow I expected mine would be "fabulous". After all, my partner and I loved each other, we were 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!
I won't splatter any mental graffiti on your romantic images but the physical reality almost never meets the expectations of either a guy or a girl. It will involve the joining of two unique individuals, so it's impossible for me to be very specific without knowing both you and your partner. You can be sure of one thing: good sex is something you do WITH somebody. It's not something you do TO them, or they do TO you.
You will almost certainly feel awkward and embarrassed. Some practice beforehand can reduce this. Although we tend to look back at some of the pre-sex lovemaking practices of previous generations - things like "making out", necking, petting, "bundling", etc - as being old-fashioned, unenlightened, or (at best) quaint they actually served the purpose of preparing a couple for a satisfying long-term sexual experience. I hope you can spend at least several days, or even a few months, learning about your body, your partner's body, your responses, and how to pleasure each other short of intercourse. I was quite embarrassed the first time I ever orgasmed with a girl present - I'm glad we weren't trying to have intercourse that time! I suspect one of your greatest anxieties, especially if your partner is somebody you really care for, is that she will be disappointed with your performance. This practice time should give you the skills you need to satisfy her.
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. You may want to be the aggressor who "takes" a woman (with her consent, of course), and be totally in control of the time and place of your first experience. I had to learn that it's AWESOME when a woman says (literally or figuratively) "I want you!" or "Make love to me.". So don't be afraid to let her take the initiative if that's her preference.
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 you'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 but having it available can dissipate some of the awkwardness.
Alcohol is generally a poor sexual lubricant, and this situation is no exception. If you are truly shy, ONE beer or ONE glass of wine might be helpful but definitely no more.
Expect to climax very fast. There are probably credible statistics published someplace on the 'net, but it breaks down roughly like this: 97% of all guys come too quickly, while 2% lose their erection and can't finish - or even insert. There WILL be a second time - perhaps after taking a walk, or seeing that ballgame, or even sooner.
What about the other 1% of guys? I suspect they have partners who understand the virgin guy's physiology and deliberately try to minimize the "problem". (Actually, many experienced women will think that either reaction - the eagerness, or the limp noodle syndrome - is cute and love you all the more for it.) But out of consideration for your ego she may help you to a preliminary orgasm before you even try penetration. You'll have to cooperate, and not resist when she uses her mouth or hands early in the foreplay. Then, after re-charging (probably 5 to 15 minutes), you'll have better control and last longer. If lasting as long as possible is really important to you, (almost certainly because you want to please HER), take a position on your back and let her get on top. Of course, that's NOT the way macho men are "supposed" to do it.
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. She is, of course, better able to feel how things are fitting together - but I may have felt insulted if that had happened on my first time.
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. Did you notice when I said " ... a woman's vagina enveloped my penis ... "? That's another way of saying, "I'm doing this WITH somebody, not just sticking it into her.".
As you finish twitching, and afterwards, it's hard to say how you'll feel. You may not even know yourself. Ecstacy - disappointment - pride - embarrassment - exhaustion - hyperactivity - chattering - stone silence. Perhaps you'll display, explore and revel in your mutual nudity - or cover-up and dress as soon as possible. You might cling to your partner, or need some time to yourself. In those moments you may feel more emotionally naked and vulnerable than any other time in your life. I'm not ashamed to say I was sobbing real tears. 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 - the physical part of our second time was about 1000% better.
(Both my wife and I like to stay coupled and cuddle after sex. I know it sounds gross, but the moist warmth "down there" feels very intimate. Unless she's on her period, cleaning up can wait - even to the next day. Others, both men and women, have a compulsion to jump up and wash even before the contractions are done. If there's a conflict with what you and your partner feel like doing, one of you may feel insulted. But 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 coupling. 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 - contrary to stereotypes, morning became our preferred time for serious lovemaking for many years. The 4th time was a few hours later. I don't think I'd change the sleeping arrangement if we could do it over. And if you're like me, you may want a lot of sex in a short time!
I know it's corny but I wish we had used some little ceremony or ritual to mark the occasion. Of course it should probably have been unexpected and spontaneous. Maybe just exchanging a flower - symbolic of being de-flowered - or some little trinket gift. No, not her panties - 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 an inexperienced guy. More importantly you are very 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 you might be urging you to stay connected and sort out a whole spectrum of unfamiliar feelings and sensations, she should be urging you to withdraw and clean up properly. Eventually you can learn to do that, but doing it correctly is a lot to expect 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.
Like I said at the start, I was also 23 when I first had sex: my wife and I exchanged virginity (I took hers and she got mine in return) on our wedding night. You can read about it 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 ]. (Scroll the thread to find my post.) Even though it was lousy sex, it was still very significant and meaningful to us! You might also look at what I wrote in the thread "First time - painful?" at [ http://www.dearcupid.org/question/first-time---painful.html ].
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, DoubleM +, writes (1 August 2008):
 In my opinion, the best way to minimize the awkwardness would be to:
1. Take your time. Be very cool. Undress and crawl into a comfortable bed and environment with your sweetheart and begin to "slowly" hug and kiss. Use the palms of your hands to slowly and lovingly rub (stroke) your lover's body - her back, sides, breasts, upper thighs, etc. Strongly caressing the lower back (waist) while embracing is a reassuring feeling to most women.
2. If really your first time, it is way too early to attempt any advanced oral techniques, but it should feel natural to kiss, lick, nuzzle and suck on her breasts, along with other areas such as arms, neck, chest, belly and wherever you feel comfortable. Trust me, her reactions to this will help guide you.
3. At your age, erection should be no problem, so at some point you slowly and smoothly roll over above her to your knees, gently pushing her legs slightly apart and lay upon her. No penetration at first.
4. Resume kissing her lips, mouth and neck while rubbing your offering against or near her private area, but with no attempt at penetration yet.
5. Expect that her reactions at this point will likely encourage you. Most girls will even help guide you if they are ready. Never be too pushy about it, but move confidently as if you expect her to be receptive.
6. If she continues to be receptive, then the two of you will find a way with what follows. It will work itself out, and if something kind of funny happens, then giggle and keep on going. Sex is fun, so don't take it too damn seriously at first, or ever for that matter. Just my opinion. DoubleM
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A
reader, anonymous, writes (31 July 2008): Maybe it will be a little awkward and embarrassing, but that doesn't mean it will be a complete disaster.
If you both feel close emotionally to one another, and have good communication then I think it will be very special and something you'll remember for all the right reasons.
The actual physical act might be a bit clumsy, in the same way it is when you are learning to ride a bike! But it really doesn't take much practice to get the basics right. If you're with the right person - and you'll know if you are - it will all be fine.
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A
female
reader, aphexinfinite  +, writes (31 July 2008):
 its like anything else like when you start a new job your bound to make a mistake and sex is just like that..heres a web site to give you some clues on how to gear yourself up..http://www.sexinfo101.com/sexualpositions.shtml... second of all just relax take it easy and dont rush in do some foreplay and work from their onwards gd luck aphex xx
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A
female
reader, anonymous, writes (31 July 2008): dude dont fool yourself having sex for the first time ha never been enjoyable especially for girls
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