Rounding Third Base

There is far more information in the pages that follow than you probably need if it’s your first time. The trouble in leaving parts out is that while they might not apply to you, they might be important for someone else.

Also, please keep in mind that couples can become VERY pregnant from their first time, even if you are doing it when a woman is having her period. The birth control part of this website is your friend.

For a brief legal reminder: Know the laws about sex in your country and state; if you are under 18, you may be breaking them if you have sex.

Now, for the fun part.

Preparing Ahead for a Most-Excellent Journey

“It was very hard to do, but I waited until I was 18 to have intercourse. It was with a guy who cared deeply about me, which made my first experience very fun and comfortable.” female age 36

Most people’s first time is awkward and unplanned. It doesn’t need to be that way. Hopefully it’s a time you will remember with fondness—the beginning of a most excellent journey.

In Addition to This Chapter

If you’d like more information about intercourse than what’s in this chapter, check out Chapter 22: “Intercourse—Horizontal Jogging.” However, that’s for once you get up to speed with intercourse. For your first time, you’ll want to keep it simple, as there are different priorities and different challenges.

Also know that here are many wonderful things about sex in addition to getting a penis inside a vagina—just reading The Guide’s chapters on handjobs and finger fucking will put you years ahead of the game.

Who to Do It With Your First Time

It’s interesting that not a whole lot of us are still with the person who we lost our virginity to. While we might have been in love with them at the time, our perspectives and romantic interests often change.

“I would have waited until I was in college. I would have saved myself years of painful, uncomfortable, inexperienced, or hurried sex. And while it just felt good to be close to the guy, I realize that I haven’t thought of him in years. Girls, you ain’t missing nothing!” female age 32

Think about the difference between a crush and a friend. A friend usually has to earn your trust and respect, while a crush automatically gets it because of the way they look or act. The chances are good that you will still have your friends in a year’s time, but you will probably have blown through your current crush and pretty much gag at the mere thought of the person.

This isn’t to say you should ruin a good friendship by having sex with a friend instead of with a romantic interest. But at least try to make sure that your first lovemaking partner is someone who has the qualities of a friend.

Doing It Sober

Please, don’t do it your first time drunk or stoned. While this is often how it happens, every survey on first-time intercourse is chuck full of horror stories from virgins who did it drunk. Seems that the couples who do it sober have a much better and more satisfying time.

Advice for Girls

This part of the chapter is written mostly for women. Hopefully, guys will read it as well. One of the keys to having good sex is knowing your body well enough to be able to say “That feels good” or “Let’s try something else” in a way that a lover can understand. This can take years. Even women who have been around the block countless times still keep discovering new things about their bodies. So consider yourself at the start of a journey.

Now, to learn more about yourself. Girls who masturbate might have a bit of an advantage, but if you haven’t masturbated before, not to worry. Wash your hands and get some water-based lube or use your own spit. Saliva is water-based and works great.

When you’ve got at least a half-hour to yourself (good luck!), or when you are tucked under the covers for bed, start exploring up and down your body with your fingertips. Spend some extra time on your neck and chest and on the area from your navel to your knees, except for your vulva and vagina. If it makes it more fun, pretend it’s a guy’s fingers instead of your own.

Once your fingers have explored up and down your body for at least ten or fifteen minutes, you might start to focus on the area between your legs.

Let your fingertips glide up and down and around your vulva, which is the outside part of what’s between your legs.

While one hand is exploring between your legs, there’s nothing written in stone that says your other hand has to be tied to your side. At the very least, see what it’s like letting it rest on a breast.

It’s now time to venture inside. Get a finger good and wet. Slowly inch it inside your vagina, which is an opening that’s buried toward the back of your vulva. It’s where tampons and penises sometimes go. The emphasis should be on “slowly.” You want to feel what your finger is feeling, as well as what your vagina is feeling.

At this point, some girls will want to put their finger in farther; others might be feeling a little overwhelmed, especially if they’ve been raised in a household that was not safe or supportive of their sexual growth. If you are in the “go for it!” group, let your finger keep going. And remember to keep asking yourself what your vagina is feeling. If you are so inclined, you might try adding a second finger. Given how a penis is most likely wider than your finger, two fingers is a nice goal, and three would be fine.

If you are in the group of girls who might be starting to feel like enough is enough, then this is a good place to stop. Just letting yourself go this far might be a really important step. If you can, try to go just a tiny bit farther next time, but don’t be discouraged if you hit a personal wall. Maybe it would be easier to have your partner read this and ask him to explore you with his fingers, although only if he has good enough judgment to know the difference between a finger and a penis!

If and when you feel ready, you might practice guiding a tampon or small, tube-like vibrator into your vagina when you are lying on your back. Also practice doing this when you are squatting, as if you were in a girl-on-top position. Don’t assume for a moment that your partner is going to have a clue where the opening of your vagina is. Be ready to help him guide his penis in, unless you don’t mind if it ends up in your belly button or bum.

If all of this seems too overwhelming, maybe it’s not the right time in your life to be having intercourse. There are lots of other ways that you and a partner can enjoy yourselves sexually without a penis going in your vagina.

Hymens Don’t Pop

The majority of women who have taken our survey did not experience bleeding during their first intercourse. Nor did their hymens (or cherry) pop. That’s because it’s a myth. To understand more about your hymen, please read Chapter 8: “The Hymen.”

During their first intercourse, some women don’t feel a thing hymen-wise, others feel a stretching or a sting, and some feel a level of pain that you might when you get your ears pierced, or worse. But if you do the exercises with your fingers ahead of time, the chances are good you won’t feel discomfort. And if you do feel pain, ask your partner to stop.

Now, for advice for members of both sexes...

Pillows and Lube

Two accessories that might really help are lube and pillows.

You have no idea how much a carefully placed pillow under a woman’s rear can help with the angle of penetration and her ability to spread her legs. It allows her to better relax her legs and her vaginal muscles.

As for lube, a few drops on the penis and a few drops on the vulva and you are good to go. If you don’t have lube, spit can work really well. Just make sure things aren’t dry before you try to have intercourse.

Go Slow and Ask!!!

After you’ve made out for about an hour and are ready for intercourse, do not just ram the penis in! Start with the head gently pushing against the rear or bottom of the woman’s labia. (It can be very helpful if she guides the penis to her vaginal opening.) If she is OK with the head pushing slightly into the opening of her vagina, ease it in just a bit more, and ask again.

Once the penis is all the way inside of the vagina, just keep it there—don’t start thrusting. This is the first time the woman has ever had a penis in her vagina. She should spend as much time as she needs to adjust to it being inside before there’s any thrusting. This can be the most important moment of your first intercourse. It will be the only “first stroke” that either of you will have in your entire lives. Stop and savor it.

Also keep in mind that a nice sensation can result if the guy pushes his pelvic bone against the woman’s while his penis is all the way in and does a slow circular motion with his hips. This may help stimulate her clitoris. She can hopefully guide him with her hands on the sides of his butt.

Orgasms, Anyone?

“Be choosy. Take your time. Touch and explore everything.”female age 36

The chances are good that guys will probably have an orgasm their first time, and girls might not—or not from intercourse alone. To understand more about orgasms, see Chapter 9: “Orgasms, Sunsets & Hand Grenades.”

If you are a guy, your orgasm might not feel as intense as when you are jerking off. After all, how many times has your penis been in your hand, and how many times has it been in a vagina? When you masturbate, the sole point of contact is your hand gripping your penis; with partner-sex, your whole body is feeling her whole body. Or how often have you had an orgasm while supporting your body’s weight on your arms or elbows? And if you wank to porn, there can be a big difference between staring into a partner’s eyes and staring up the crotches of actors. It often takes time and experience to put lovemaking together in a way that beats beating off. (Porn is a lame model for lovemaking. Do they ever ask each other what feels good or kiss a lot?)

If He Comes Really Fast

Some of us guys can come pretty quickly the first couple of times we have intercourse. Some of us don’t even get a penis inside before blowing a wad. Anxiety can do that, and there’s nothing wrong with being anxious.

Coming soon might not be such a bad thing. Part of the reason why sooner might be better is because it might be the first time a woman has had a penis in her vagina. There might be a little rearranging or familiarizing that needs to go on inside of her pelvis. As a result, it could be that nature actually intended for first-time boys to launch early.

Still, if you are worried about coming too soon, get some really thick condoms made out of recycled boots or something. Click on the following link to download the chapter on coming too soon from the Guide To Getting It On titled (Dyslexia of the Penis--Improving Your Sexual Hang Time.

If you feel like you are having the opposite problem and you aren't able to come at all during intercourse, click on the following link to download the chapter on Delayed Ejaculation from the Guide To Getting It On.


The time you spend together after you have your first intercourse can be as important as the time during and before. So don’t try to do the deed minutes before your team bus is leaving for the state finals. Spend time together afterward and be aware of each other’s emotions. Maybe you’ll want to hold each other, or maybe you’ll want to run downstairs and raid the refrigerator.

You can’t predict how you will feel afterward. Perhaps you will be relieved, maybe happy, disappointed or sad. Perhaps you’ll feel extra close to your partner, or maybe you’ll feel alone and isolated. That probably depends more on the quality of your relationship than anything else. Allow for a full range of possibilities and the time to experience them in the hours and days that follow.

What if It Wasn’t Mind-Blowing?

“Relax and don’t expect it to be like the romance novels.” female age 32

Who knows what makes for mind-blowing sex, but don’t be disappointed if it doesn’t happen. And if you are thinking that your first time will change your life or transform your relationship, it probably won’t unless you get knocked up or get an STI.

Where to Do It

“Our favorite place was on the floor in the room over my parent’s garage when they were out somewhere. When the garage-door motor clicked on and started vibrating the floor we had just enough time to finish, clean up, button up, and act natural before my parents walked in.” male age 26

For your first time, a quiet, familiar and comfortable setting might be best. But finding a private unhassled location can be a challenge any time you have sex! Ideally, find a time and place when roommates, friends or parents won’t be barging in. And please don’t do it your first time in a spare room at a party. You might not care much about yourself now, but maybe you will in a few years. Thinking back over that could be a big regret.

Once you have lots of experience under your belt, exotic locations are fine places to have sex. But for now, safe and familiar is best. If you try it in a bathtub or hot tub, chances are good the water will wash away your natural lubricant. If you do it on a beach, the sand will find its way inside the woman’s vagina, which is how sandpaper came to be invented.

No Time for Sex Toys

If you are so inclined, there’s plenty of time in the future to bring out your stock of dildos, cuffs, and strap-ons. When it’s your first time, why not stick to the lovemaking basics?

The one exception might be a vibrator, assuming the woman already uses one and enjoys it. It might not be a bad thing for her to get herself off right before you try intercourse. This can help her relax and it might help her first intercourse feel really nice. Her partner can always hold her while she masturbates or uses the vibrator.

If You’ve Waited until Marriage

The average reader of The Guide is not necessarily the kind who waits until the first night of marriage for sex, so it’s not like we have a huge data-base of advice to pass on. But if you think about how stressful a wedding and reception can be, the night of your wedding might not be the best time to make it your first time. Then again, all that adrenaline might be just the ticket! Talk it over ahead of time.

Advice for Guys

Look over the following advice that our female readers have for women who are doing it for the first time:

“Make him go slowly and be sure that you are aroused sufficiently before you let him enter you because it will probably be a little uncomfortable the first time. If he rushes, it will hurt and you won’t enjoy it at all.” female age 35

“Make sure you really want it and it’s not about being pressured. Masturbate together first. Be comfortable together. My first time was painful and humiliating; there’s got to be a better way.” female age 38

“Make him read the Guide To Getting It On first!” female age 30

Men who are virgins tend to be at a disadvantage their first time because they usually don’t have the courage to admit that they haven’t done it before. So instead of being honest and trying to explore together, the guy tries to fake it. Hopefully, readers of this book won’t be so silly. Your first time can be special and sweet, but not if you need to pretend that you know what you are doing when you really don’t. Here are a few tips for guys who are about to make their maiden voyage:

Positions--Your first time is no time to get fancy. Go with the old-fashion missionary position where she is on her back and you are on top. There’s plenty of time later for her to be on top. Missionary is better for the first time.

During Intercourse--If you are on top, she’ll want to feel some of your weight on top of her, but not the full nine yards. So use your arms, elbows and knees to support yourself and thrust with your hips. Not to worry, you’ll get the hang of it. Heck, even your dad did.

Thrusting Speed--Contrary to what you might have seen in the movies, thrust slowly. Go really, really slow and enjoy each and every slip and slide. If she wants you to speed up, she will tell you.

Your Lips--You will be hard-pressed to find a single woman on the planet who wouldn’t enjoy it if her lover planted some tender, gentle kisses on her neck or lips as his penis is getting to know her vagina.

Porn--What makes sex work in a relationship and what makes it work on a TV or a monitor are two very different things. In porn, the camera abhors a tender and loving touch. It comes across as boring. In real life, tender rules.

Oral Anyone?--In some situations, it makes perfect sense for you to go down on her before intercourse. In other situations, this would be way too overwhelming. The two of you need to decide together.

Condom Practice--Find a condom to practice putting on. Once it’s on, jerk off by thrusting your penis into your lubed hand. This is important.

Erections #1--Not to worry if your erection is a bit flaky. Chances are it’s never been under this kind of stress before. Keep kissing, laughing or feeling each other up instead. If you do what’s described in Chapter 15 on finger fucking, she’ll forget all about your penis.

Erections #2--First-time lovers sometimes rush because the guy might be worried he will lose his hard-on. If he does, he does. It’s far more important that you take your time, with lots of kissing, touching, and more kissing. The goal of sex is to share pleasure, fun and intimacy. You don’t need an erection or intercourse to do that. Coming: It’s not unusual to come kind of quickly your first time. However, some guys aren’t able to come at all. Either way, don’t stress it. This is about the two of you enjoying each other, not about coming.

Condoms, Condoms, Condoms

Unless you’ve really got it together and visited Planned Parenthood, the chances are that condoms will be your default method of birth control. If used correctly, they can be very effective.

If you are a guy, try to get stash of condoms and water-based lube ahead of time. You’ll want to study the package, and learn how to open it in the dark. As you are opening it, try to figure out how to manipulate the condom by feel alone. Experiment with rolling it on your dick, leaving a half inch at the top with the air squeezed out. Then put some lube in your hand and try jerking off with the condom on. See what it’s like to thrust with your hips into your lubed hand.

Thrusting into a well-lubed hand with the condom on will give you a better sense of the condom’s road-handling abilities.

Then, after you’ve blown a wad, look at what happens to your penis. If you are like most of us, it will start to shrink. This is why guys need to crimp the bottom of the condom around the base of their penis as soon as they come, especially if their penis does a rapid deflate. Otherwise, the condom will slip off, and if you keep thrusting you will push it inside your partner’s vagina.

If you are a girl, get extra condoms and try putting one on a banana or something penis-shaped. Learn how to open the package in the dark and how to roll it on, leaving a half-inch at the end with no air in it.

If it is at all possible, get the morning-after pill (Plan B) in advance. That way, if a condom breaks, comes off before it’s supposed to, or you forget it, you’ll have a really good chance of preventing an unwanted pregnancy. And if for some reason you do it without birth control, make sure he pulls out before he comes.

16 vs. 26

Plenty of people don’t lose their virginity until they are in their twenties. The nice thing about waiting is that you tend to be more sensible about it and you have a better experience. Many of the late-bloomers we have heard from say it’s much better experience. This is from a reader who didn’t lose her virginity until she was well into her twenties:

“I was surprised at how tricky losing my virginity proved to be. The first couple of times my boyfriend and I tried, my vaginal muscles were very tight and penetration was painful. So we slowed down and tried other ways of loosening the muscles (fingers, a vibrator, etc.), I visited the ob-gyn to make sure nothing was wrong (there wasn’t), and we waited for a night when I was nice and relaxed. The first couple of times we successfully had intercourse were amazing—I felt a bit of pain with initial penetration, but once my body got accustomed to him the physical sensation was wonderful, and we had a lot of fun trying different positions and experimenting with what felt good!”

A Very Special Thanks to Angela Hoffman for advice and help; to Chris, a contented average dude from Canada; to Figleaf; and to Dayna Henry and her students at Indiana who suggested that the former title of this chapter, “Losing Your Virginity,” carried cultural baggage that implied a loss for women but a gain for men.