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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I am in reasonable — not great — shape. I don’t have any problems bending and twisting into the normally requisite sex pretzels.

I’ve been married to my husband for 13 years. The sex was terrific when we got together and persisted terrifically — but with no orgasms for me. Then about six years ago he lost interest in sex. Two years ago, I handled that problem by taking a lover.

My lover is amazing in bed. The chemistry is mind-bending. He’s a devotee of long foreplay, making out, oral/genital stimulation, etc., but still I can’t orgasm when we are having sex!

What am I doing wrong? All I want is the chance to come at some point during a lovemaking session with the man I love. I don’t believe in or care about the myth of the simultaneous orgasm. I don’t expect multiples since I can’t even get there once right now. Are there techniques, tricks, workarounds I might not know about? Do you have any suggestions for relaxation techniques, or mental exercises that might work?

Or should I just give it up, have my orgasms alone, and be content with the pleasure (and, oh boy, there is pleasure!) that I get from sex that only results in an orgasm for him?

Want More

Dear Want More,

In real life as in fiction, women are intrigued — sometimes quite secretly — by this question. In Colette’s short novel “The Innocent Libertine,” a turn-of-the-last-century adulteress searches for pleasure she can’t define — but knows it when she sees it. In “Four Blondes,” Candace Bushnell describes a smug modern blonde who doesn’t believe women can really come during intercourse. A character in Mary McCarthy’s novel “The Group” is told by her lover that she’s unusual because she does come this way. And then, of course, there’s “Sleeping Beauty,” which could be a metaphor for your situation. Everything from the fanciful to the bitchy has been said, I suspect, about this topic. How much of it is true?

Is it the way we’re built, individually? Just a question of anatomy? Some women swear by specific positions: I have a friend who is convinced that being on top during intercourse is the key because of the way she’s designed. But then she wonders if it might be “because it happened the first time that way, so now I don’t trust any other position.”

But maybe it’s the man we’re with? The special chemistry between two lovers? I know more than one woman who switched partners because having an orgasm during intercourse made her feel that she was finally in bed with Mr. Right. I also know a woman who prolonged a relationship with Mr. Wrong because her partner possessed this special ability. She saw it as his ability, not hers, and that’s what she has in common with women who identify their partners as Mr. Right. These women cede the ability to a man, acknowledging that it makes them less self-sufficient. That’s a troublesome feeling for some women and it might be a desire for self-control that stops pleasure from turning orgasmic during intercourse. Then again, there might be a really good reason for holding back — perhaps your body is reacting to something your heart knows about a particular man.

I have a friend who insists she can come this way with any man if she simply deprives herself of satisfaction for long enough. “It has nothing to do with meeting Mr. Right,” she assures me. “It’s all about timing and where you are in your life.” She discovered this when she was living with a man who deprived her of sex. “It was awful and I felt miserably rejected. When I started having an affair, I was so starved for physical contact that it just happened — for the first time — with my outside partner. So the awful thing turned out to be a blessing in disguise because I finally knew what it was to be desperate for sex. The satisfaction was intense but that doesn’t mean my lover was Mr. Right. He was just there at the right time. You can simulate desperation if you stop masturbating.” And sometimes she does that, even now.

I’m actually a member of the Mr. Right school of thought (though I also believe some women are destined to have many Mr. Rights while others will probably meet just one). But my friend has a point: Sometimes, masturbation gives us too much control of our own pleasure, and we don’t let the body follow its mysterious, unstated agenda. I can hear the uproar! “Masturbation is a boon to womanhood! We have to find out how our bodies work!” That’s true. But masturbation is easy for you and for many women, which makes it readily available. There is something enticing about the pleasure that can only be given by a sex partner, experienced by chance, withheld and offered. It’s like a really delicious meal cooked by someone else — and you’re not sure what all the ingredients are, even though you are yourself a very accomplished cook.

So why does it happen to some women the very first time they have sex (as it did with another friend of mine at 16) and why do some women get there over a period of time by experimenting with different lovers? (This particular friend was beset with teen guilt after that orgasmic debut and she has not had orgasms during intercourse since then, despite a long list of bed partners.) Why do some women yearn for this kind of orgasm, while others simply don’t care — they’re happy to have one and the “how” of it doesn’t matter. Maybe you’re trying too hard — trying to will some feeling into existence that wants to surprise you. And maybe your body would like to acquire more experience. What’s to prevent you from supplementing this affair with additional companionship?

On a practical level, an orgasm during intercourse is probably different from the orgasms you give yourself — if you’re comparing the sensations of intercourse with the sensations of masturbation, you might even have an orgasm without recognizing it. The best “plan” is to have as many different orgasms as you can — whether from oral and manual sex or with various toys. Just getting used to a variety of orgasms is a first step to overcoming the notion that you “can’t” come this way — or you “only come” that way. I hear too many women and men insisting that they are limited to one kind of orgasm, as if their bodies have fixed and finite abilities. We can always learn new things about our bodies. Your body has a past (which you know about) and a future, which is mysterious. Who knows what may happen to it next? The orgasm you sometimes dream about is likely to occur when you don’t expect it to.

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What percentage of women might accept my fetish for what it is? How do I bring up the subject before either of us has some sort of emotional commitment to a relationship that might not work?

Likes Dresses

Dear Likes Dresses,

Flirt, don’t blurt!

I don’t think it’s very romantic or sexy to provide a prospective love match with a list of your erotic likes, dislikes and fetishes. You want sparks to fly or at least flutter during the buildup of discovering each other. Is a fetish one part of your personality that gets expressed in this process? Or is it an oddly shaped room in the attic of your house that needs pointing out to a prospective buyer?

Listing all your needs and fantasies in a personal ad, or at the beginning of a relationship, is probably efficient, but the other day I saw an ad placed by a girl who’s looking for a guy who will play with her hair while they’re kissing, and all I could think was, “How do you enjoy having your hair played with under such a contrived circumstance? Isn’t that sort of thing supposed to happen by accident?” Ditto for a million other physical and emotional discoveries that turn sex and dating into a lovely diversion.

I do not like to think that sexual compatibility in the context of love can be prearranged. But you do have to be realistic. If you have a taste for something not taken for granted by the local culture, it is probably wise to do the math. The chances that you’ll meet someone who likes an eccentric, refined pleasure aren’t as great as the chances of meeting someone who likes to hold hands at the movies. But if you harbor a kink that happens to be in vogue, you’re in luck because, like all other fashions, a sexual fad persuades many people to try something on for size. When something “strange” becomes a fad, a certain number will sample it just once while others discover a taste for something new. As it happens, cross-dressing men have become trendy — so the math is working for you in some respects. Ten years ago, women were not as familiar with male cross-dressing, but now it’s all around us.

The erotic buzz a woman can get from a cross-dressing guy may come as a surprise. And the more style and poise you have, the more appealing you will be. So it’s not a question of percentage — you can’t seriously think there’s a way to measure the number of women who go for this, can you? I prefer to ask, What percentage of cross-dressing men have a clue about what they’re doing, aesthetically? It’s a question of quality versus quantity. If you are among the elite number who has that special something when dressed like a gal, you are ahead of the game, and that’s more important than knowing how many women are willing to play. (That inane math stuff again!) Style can trump circumstance.

Do I seem to skirt the issue? Well, the thing is, you have a hobby or pleasure that not every woman will relate to and you need to avoid the sort who will run shrieking from the room. I think you need to include in your dating plans not just women who already know they like cross-dressing but women who might get into it because they’re turned on by you. I have noticed that effective cross-dressing men possess a twinkle in the eye and a flirtatious, playful intelligence that can be quite seductive.

It’s not about finding a woman who merely “accepts” cross-dressing. You don’t want a partner who looks at your cross-dressing as a “lie back and think of England” ritual that she tolerates. It’s about meeting a woman who likes you, is turned on by you — and you just happen to be a cross-dresser. You’re also looking for a woman who is open to new experiences and pleasures. Now you could, conceivably, hook up with a narrow personality who happens to be turned on by cross-dressing. Nothing wrong with that up to a point, but she might have little else in common with you. You need to have more in common to have a lasting interest in each other. If you make a fetish of your fetish and reduce your romantic needs to that alone, you risk settling for less than you deserve.

You could run a classified that defines you as a cross-dressing straight guy right upfront, or you can hint at the issue by mentioning favorite books, performers, movies and boutiques associated with cross-dressing. For example, if you advertise that you’re a man seeking a woman for a relationship and you’re a RuPaul fan, you’re saying a lot right there without being blunt. I prefer this imaginative approach — as opposed to presenting yourself as a person with a menu of needs — and you can use it in any conversation with a new girlfriend as a way to break the ice.

There is too much confession and not enough conversation in this world! Get into the habit of discussing your kinky secret without being personal. Your fetish is not just a personal issue — it’s a cultural phenomenon. Rather than blurt out, “By the way, I’m into cross-dressing. Can you handle it?” you might talk about the history of cross-dressing, the dating mores of female geishas and male kabuki performers, a new book that you saw (such as Miss Vera’s “Cross Dress for Success”) or the winner of this year’s Turner Prize — a potter, husband and father, Grayson Perry is also known for his cross-dressing skill. If you take up the subject of Perry, focus on how convincing he looks in a white dress, not how strange he might seem. Through conversation, you will soon find out how open or closed a woman’s mind is. Then you can decide whether — and when — to reveal your own interest. She might surprise you by knowing a few things about cross-dressing herself. Think of it as constructive flirting.

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I don’t want to have an affair. For one thing, I don’t want to mislead another woman into thinking I would ever leave my wife, because I just won’t. I don’t want to. What I do want is to have sex a lot more frequently than I am having it, and I want to experience somebody new. I want that first excitement that comes from undressing a new person for the first time (or even 20th — it doesn’t wear off all that quickly). What kind of clothes they wear, their underwear, how they kiss, how they smell, what gives them pleasure. While my youth certainly didn’t rival Casanova’s, I was fairly active, and this lengthy period of inactivity is difficult.

I would be racked with guilt should I arrange a meeting with a call girl, but the very fact that I’m even thinking about it is a sign of something. Also, I am a little intimidated by the whole “call girl” scene; I wouldn’t have any idea how to contact one. (I certainly don’t want to call a random ad!) How would I know which ones are reputable vs. the ones that are more marginal, and so on. (And how can I go to bed with a woman that I can’t kiss? That seems so odd to me.)

If you have any insight, I’d love to hear it.

Frustrated but Faithful

Dear Frustrated,

Going to bed with a woman you “can’t kiss” seems odd? Well, sex with a prostitute is supposed to be “odd” — different, anyway, from married sex, romantic sex, procreational sex, affair sex and many other forms of sex. Commercial sex has its own logic, rhythm and language.

Sex with a woman you want to kiss can be very enticing even if it does not yield a kiss — the first, second or 20th time. If you’re attracted to a woman and turned on by the prospect of seeing her, that’s what matters. Who knows? Maybe, if you get to know her, she will make an exception and, eventually, kiss you. But be prepared, when paying for sex, to play by different “rules” — think of marriage or dating as chess and prostitution as backgammon. You might do things with a prostitute that you never do with other women while things you do with other women are not always part of sex with a prostitute. For that matter, many prostitutes will try things with customers that they won’t even broach with their boyfriends or husbands. Prostitutes and their customers inhabit a separate erotic zone.

Alas, there are serious risks attached to cruising for a paid sexual encounter in the United States whether you search the streets, the classified ads or the Web. The majority of advertisers are probably genuine but you could be answering an ad placed by a very industrious vice cop. Police departments have been known to sponsor phony bordellos and escort agencies in order to find victims for their customer stings. You could also be the unwitting target of a scam artist who steals your money. The safest way to pay for sex in the United States is within the walls of a legal brothel in Nevada. OK, this is not to everybody’s taste and Nevada is not always convenient — but it’s legal. Outside the United States, Holland and Senegal are two countries where prostitution is legalized; others are Germany, Curaçao, Greece and parts of Australia.

You say you would be racked by guilt yet you’re still curious about commercial sex. If you decide to go through with this, you must be careful not to inflict your ambivalence on a sex worker. If you talk too much about your guilt or your marriage, it may spook her. Many prostitutes are sentimental creatures who like to make their customers happy. Even if you endure your pleasure in a guilt-ridden funk, you should let her feel good about what she’s doing. If you pay for sex, try to be the kind of customer prostitutes look forward to seeing.

Keep in mind, if you were arrested for patronizing a prostitute, it might be discovered by your wife, and it would probably upset her. And in some cities the police will disclose the arrest to your employer. Guilt can make a man “want” to get caught or punished without realizing it. Some people may think that guilt is just part of the deal when you pay for sex. Not me. I think guilt is a twisted form of resentment. I’m not convinced that you are ready for the sexual adventure you contemplate. Try to work through this guilt or at least get a handle on what it means. Unexamined guilt can be hurtful and dangerous.

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In his defense, I happen to know that he never really got a chance to practice just kissing before he first became sexually active as a young teen and he has to undo years of habit (he’s a widower).

How can I teach my man how to kiss me?

Need to Be Kissed

Dear Need to Be Kissed,

Yours is a vexing problem experienced by many: You are attracted to — and physically aroused by — someone who leaves you feeling rather dissatisfied. You may hunger for sexual contact with him and you’re (mostly) compatible in bed. That you find his eagerness endearing says you care for him. In many ways, it sounds like a good relationship. And yet, you say, a special ingredient is missing.

First of all, I think you can enjoy sex even if that longed-for ingredient isn’t there. This, for me, is the difference between good sex and great sex. This might also be the difference between an interesting, meaningful relationship and that great sensual love of your life who may appear when you least expect. Lots of men and women settle for good sex in the absence of amazing sex, and that’s not the worst choice you could make. It would be horrible if you were settling for bad sex — but this isn’t bad sex that you describe. It’s good enough until a better fit comes along.

My question to you is, do you really need to be kissed? Before you define yourself as a person who needs to be kissed, perhaps you should ask yourself why. Is it, perhaps, a notion picked up during an earlier phase of your sex life? In high school, perhaps? Do you have orgasms only when kissing is involved? What happens when you just don’t kiss him? If you have orgasms, perhaps you don’t need to be kissed by this particular man. Perhaps you prefer to be kissed (by someone who knows how) but can do without it. What is it about kissing that you like? Is there another way to (almost) fulfill this desire by doing something else with him?

There may be a way to modify his style of kissing. If, for example, you take the lead — without discussing it, kiss him on the mouth exactly as you like to be kissed — he may “get it.” Perhaps you’re trying to reach his mind by combining words with physical demonstration when it’s really just his lips that need a good talking to with your own. Get into the habit of kissing him like this — and just don’t let the annoying stuff happen. When he kisses in a way that turns you off, gently pull away and get busy with some other pleasure. Nibble his neck if you must while contemplating your next move. Don’t discuss or try to “negotiate” — just make it happen. Who knows, you may succeed in brainwashing his lips.

Yes, I know, it’s not as exciting as being kissed by Mr. Right, but it may be pleasurable in some small but significant way to take the initiative with Mr. (Almost) Right. I also realize that small pleasures are tantalizing but not satisfying. But perhaps he’ll respond by kissing you the way you like to be kissed.

What if he never does? Don’t be too hard on yourself — or him. I’ve had many partners who respond to my hints, requests and cues but I’ve also found that some are just learning disabled when it comes to a particular aspect of pleasing me. Imperfect sexual partners do exist. I think it’s smart and kind — to yourself and to him — if you take what pleasure you can from imperfect sex without investing too much in the situation at large.

Remember also that he may have developed a habit of kissing that comes from years of intimacy and practice with another partner who liked it that way! The very thing you find irksome in bed may have been totally another person’s cup of tea and what if he spent years providing this cup of tea? Some people approach sex as emotional attachment, some as social skill. It sounds like he’s the attachment type and you’re the skillful type. Attachment types can get attached to a way of kissing, touching, performing oral sex or whatever — and he may never be as versatile as you’d like him to be. It’s maddening, but there you are. There is only so much you can teach a person to do in bed. Maybe he’s slow to learn and maybe you can refine your teaching skills — but maybe you’ll have to accept that you are incompatible when it comes to kissing.

If you decide to enjoy this man “for now” — while leaving the door open for new sex partners — be gracious. Encourage him to kiss you below the neck. Your body might surprise you. Pleasure can be intensified by removing one of the “usual” elements from sex, by resisting some action (like kissing) which you regard as normal. If you continue to have sex with him while keeping your options open, be tactful, discreet — and fair. Leave him with good memories and create some for yourself.

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