Two virgins

We are both in our 20s and virgins. What should I consider before making love for the first time?

Topics: Sex, Love and Sex,

Two virgins

Dear Tracy,

I am a 22-year-old guy. I studied abroad in Australia a year ago, and in the last month I was there I fell in love with a girl who lived near me. We spent nearly every waking moment of the time I had left there together. Since I have left, we have spent quite a large sum of dollars, words, and moments staying in touch with, and getting to know each other.

She is coming here for three weeks for Christmas. She has never seen snow or really known winter. She has never been to the U.S. or Canada, and I am taking her to Toronto, Boston, New York and Washington while she is here. But it is another first that worries me. I am a virgin. As a matter of fact, this is the first and only girl that I have ever even kissed. The only way I can explain it is that my parents had me in an all-male Catholic middle and high school, and I am very shy. Shy, and totally petrified now of the idea of making love. I obviously want to, and we have talked about it, though the talk was less about the pleasure of it and more on the protection and safety measures. Though we are both shy people, I think that we are both ready and there will never be a better or more romantic way, time, place, or person. Plus, I think she may be the one. To make matters more complicated, though perhaps a bit better, she is a virgin as well. So, it is something we are going through together.

I hear the first time described as being painful and awkward for a girl. She is very shy and I am not sure that, even as close as we are, she is going to be able to really tell me, or know, what I should do to make it as pleasurable an experience as possible for her. I know how in general the entire process is supposed to go. But, I am an engineering student at heart, and was hoping for some expert advice; tangible things that I can do, and steps I can take, to try to make it the first time that she deserves.

Please, I would appreciate any advice that you can give. If you could go back in time, and make some suggestions to the guy who you shared your first time with, what would you say? What would you have done differently or kept the same? Please, help me to make this experience the one I know it can be. We have waited so long for it that we deserve it, that she deserves it, to be special.

First Time

Dear First Time,



Wow. I feel your anticipation. There is nothing I would change about my first time — except, perhaps, the size of our bed. Maybe — and it’s a big maybe — I would have lost my virginity on a queen-size mattress instead of a single. But teenagers can be excused for having sex in slightly childlike or raffish surroundings.

Since you are not a teenager and you have both waited so long for this to happen, I recommend a big comfy bed in a place that makes her feel pampered and safe. (Intuition tells me that a woman who waits this long will appreciate nice bedding.) By “pampered” I don’t mean that she must lose her virginity at a four star ski resort — but you should find a pleasant, clean, private space that feels happy. You can experiment with outré locations later on!

Don’t worry too much about making the first time perfect. First time sex is important for emotional reasons and, if the feelings are right, the next time and the time after (and so on) will continue to get better. This probably is not the raunchiest sex you will have with her, but that’s OK because you want her to feel cared for. It’s better to risk being too nice to a woman having sex for the first time. This doesn’t mean you have to be an altar boy the next time you get into bed. As you get to know each other, she might want you to be rakish or aggressive. You can vary this approach and surprise her a little. It’s this element of change and surprise that makes a woman feel that she is being made love to by a knowing partner.

Sex isn’t about making a big first impression and then settling into a routine. It’s about pleasure that grows more complex with each new encounter — but don’t feel compelled to try 20 different positions. If you find a mutual turn-on, return to it and see what happens.

What I would not change about my first time is the use of birth control and a consequent build-up to intercourse, which happened a few weeks after I made the decision. Planning your first experience is commendable. More people should!

Is your contraception method compatible with first-time intercourse? If she’s using a diaphragm she might spend more time fumbling than she really wants to on that first night. The Pill plus a condom is a popular and smart choice, for the Pill is not entirely foolproof, especially in the hands of a newbie.

If you intend to use a condom — and you should — don’t wait until the first time you have sex to find out what it feels like. Buy a box and try them on. Read the instructions. Twice. Many people fail to do this even once. You can do all this in total privacy. Get familiar with the sensation, the process, of putting it on. Learn about techniques for removal and possible shortcomings. Some men find out during sex that they need a larger condom because they didn’t have enough sense to try it on first! Start with a normal size and, if this feels too tight, try other brands in the XL and XXL range. You’d be surprised how many sexually experienced people have awkward sex because they didn’t think of this beforehand. A more experienced woman might carry three different sizes in her makeup bag — just in case — but your girlfriend is not likely to think of this.

Buy a bottle of good lubricant — a liquid variety like Astroglide or KY, not a tube of gel. These newer liquids are as essential to sex as water is to a plant. Practice applying it to the outside while you wear the condom. You can also use a lubricant to put the condom on, another neat trick you can start learning before, not during sex. Of course, you will find out when you bed her how much lubricant is too much or not enough but you can start getting a feel for it now. If all this preparation results in an orgasm, enjoy it!

By playing around with the ingredients — condoms and lube — on your own, you can be the slightly more experienced one, which will put her at ease. Since you’re an engineer, some of this comes naturally and you’ll start noticing little things that need fixing or dealing with. Engineers, by the way, are often good at the details of pleasure because they aren’t afraid to apply their formal training to intimate situations.

First-time sex can be painful for a woman and additional lubrication can reduce her discomfort. Have a bottle open and ready next to your bed. You don’t want to stop in the middle of kissing her earlobes or going down on her to extricate a KY bottle from its wrapping. In fact, you sometimes need a pair of small scissors to get the wrapping off. So do that before — and make sure the condoms are also ready. Some of us slip our supplies under the pillow when nobody’s looking.

If she’s in pain the first time you have intercourse — despite generous amounts of lubricant — premature ejaculation is more than diplomatic. The awkwardness of first intercourse is real but overstated because first-time intercourse can be rather brief! To reduce discomfort when a man enters her for the first time, she can breathe slowly through her mouth into her abdomen. This is a relaxation technique for body and mind, used by non-virgins when challenged by a man’s size or ardor.

Use a barrier (condom or diaphragm) to protect her cervix from exposure — even if you’re a virgin and unlikely to harbor an STD. Get into this healthy habit up front, not later — no woman should expose her cervix during intercourse unless she is planning to get pregnant. Birth control is something you should discuss openly to prevent misunderstandings — coyness has a role to play but not here. Find out how she feels about accidental pregnancy. Do not assume that she feels as you do. Two people, deeply attracted to each other, can disagree profoundly about things like pregnancy, abortion and marriage.

I sometimes think the world is divided into people who plan their first encounter and people for whom it happens like magic. For those who don’t plan there is often lots of passion, spontaneous emotion — and the risk of an STD or pregnancy. Sometimes, there is conflict, reluctance or guilt. For the planner, first sex is often safer and free of guilt, but less likely to feature fireworks.

So, if a premiere performance is more friendly than passionate, don’t worry — the passions experienced by a sexual planner are probably more intense and may also be more lasting.

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