Indispensable tonight’s-the-night tactics, based on real-life, experience. By Lynn Snowden Picket
ONE OF THE BEST MOMENT IN LIFE IS THAT SWEET, thrilling realization that you and your guy are going to wind up in bed together for the very first time. This revelation and the accompanying rush of pleasure could come about after you’ve been dating for three months and he calls to suggest that you stay over after your date this weekend. Or it might be on your fifth date, when he winks at you from across the table at a candlelit dinner & you think: Tonight. Or this intimate epiphany could surprise you as you’re finishing your third frozen margarita, and, wow, the room is suddenly hot, and you’re hot, and the guy from the mail room is certainly hot, and he’s such a great dancer, and is that an available taxi? One of the hallmarks of maturity is knowing how to handle the consequences of your lust and your judgment at a time like this. Speak to a wide range of women and men on the subject of The First Time With Someone New, as I have, and it’s clear this can be tricky terrain indeed. But the next time you find your-self hiking into the valley of sex with a new man, you’ll carry the wisdom of others who’ve been there, had jitters about that – and, most important, come back to discuss it.
FIRST, LET’S COVER THE BASICS: LIQUOR, LINGERIE AND HANDCUFFS. You don’t want to be smashed at a moment like this. Alcohol may loosen inhibitions, but too much of it can mean nausea, failure to reach orgasm and the inability to remember whether you achieved orgasm when you’re nursing a hangover the next day. Not to mention the fact that a pounding headache tends to usher in strong feelings of regret that you slept with him in the first place. Also, if he’s drinking a lot, the orgasm potential will diminish further, as he may not be able to sustain an erection, which definitely puts a damper on the evening.
The first time with a guy is a sexual “getting to know you,” and it’s the steamy passion that takes center stage, not fancy positions or kinky variations. This is not the time break out handcuffs, announce your desire to try anal sex or present a monogrammed cock ring purchased for the occasion. Unless, of course, these are particular preferen-ces that the two of you have discussed in detail, on many occasions, for hours on end. And in that case, to neglect their introduction at this special moment would be remiss. Most of us, however, don’t have those sorts of first dates. When in doubt, stick to the basics. Mother are famous for saying that you should always wear nice underwear in case you’re in an accident. Most women have long suspected that ER doctors may not, and should not, take the time to notice the state of your bra and panties, but your date certainly will, and you don’t want to ruin this first impres-sion. ”I always make sure I’m not wearing granny under-wear if I even suspect sex is a possibility,” says one friend of mine, which, of course, raised the questions as to why she even owned any granny underwear. “I don’t,” she said, a little huffily.” I threw it all out once I lost my virginity.” It should be said that it’s never too early to throw out all of your sad-looking under-wear. After all, your apartment could catch fire when you’re half-dressed, and you don’t want the firefighters talking about how you could have tied your panties to the bed and lowered yourself out the window.
HIS PLACE OR YOURS? OR NEITHER? As tacky as it may sound, you should ask yourself if you actually want to spend the entire night with your guy. If you’re unsure for any reason – maybe you have an early-morning business meeting, or you’re not quite ready for him to see you without eyeliner – don’t suggest your place. (In one of her standup routines, Janeane Garofalo riffs on the pitfalls of letting a guy in the door, comparing herself to a bartender at last call as she tries to rouse him out of her bed: ”Come on! Let’s go! You don’t have to go home, but you can’t stay here!”)If you’d also like to completely avoid the delicate issue of whether he wants you to sleep over, you could opt for sex alfresco: a bottle of wine, the two of you and a blanket stretched out under the stars. There’s even the time-honored, but not terribly comfortable, backseat of a car (as long as it’s not in the parking lot of the bar you just left.) In most circumstances, though, roommates or the lack thereof are often the biggest factor when it comes to the location. Alice, who’s just out of college, says, “I knew my roommate was staying over at her boyfriend’s, so even though I slept in the living room, I figured it was safe to invite this guy, who has two roommates, to my place. Right when we were naked and things were just about to happen, the front door burst open! My roommate came home, crying. She’d had a fight with her boyfriend. “The romantic mood went out the door, along with her new man, who knew better than to stay.” But the next we went out,” says Alice, “he tucked a key to a really nice hotel in my napkin. It was extravagant, but he said he wanted our first time together to be perfect.” And it was, sort of. More on that later.
PERSONAL GROOMING, OR WHAT YOUR PUBIC HAIR SAYS ABOUT YOU. Men should realize that one of the big reasons a woman says no to sex is because she needs to shave or get a bikini wax. “One time I was making out with a guy, and all I could think about was if I could sneak into the bathroom to shave my legs,” says Mira. “I decided I couldn’t, and I was too hairy to have sex, so I said I don’t want to rush things.” And yes, there are women who deliberately avoid shaving to ensure that raw lust doesn’t overcome the plan to wait a few more dates before taking the plunge. One woman, Stacy, assured her boyfriend (now husband) that she was absolutely not in the habit of sleeping with a guy on the first date, even though that’s exactly what she did with him. “Feel,” she instructed him the morning after, running his hand over some serious leg stubble. “Does that seem like I planned to do this?” He could only conclude, rightly so, that he had swept her off her feet. Interestingly enough, the men I surveyed said they couldn’t recall leg stubble ever being an issue once both parties were naked. As one guy, Sean, puts it, “My God, who’s paying attention to her legs at a time like that? If other parts are hairy, well, that’s different.”
Sheri, a woman who’s had electrolysis on her bikini line, says that when she impulsively, and uncharacteristically, had a sex with a guy on their second date, he told her that he was a little put off – and why? Because the fact that she had “obviously shaved” proved she was “expecting it.” The poor guy didn’t understand the modern technology in the field of hair removal. When I told this story to my friend Pat, he cautioned that “a guy who would make that kind of comment is a guy with more problems than you probably want to deal with.” He also concurred, with typical male candor that no guy wants s to be surprised by “a really hairy beaver.” Okay, we get the point.
WHAT TO BRING, AND WHY YOUR PURSE SHOULD HAVE A ZIPPERED COMPARTMENT. A law of physics governs both condoms and tampons, causing them to fly out onto the floor if anyone at all is watching when your purse tips over. Hence, the zippered compartment. If you’re concerned about guys equating your carrying condoms with your having loose morals, you might defuse this absurd, yet common, reaction with humor. At the moment he expresses even mild surprise that you’re so well prepared, say, “Are you kidding? I’ve been carrying this around in my wallet since I was 15! I can’t believe I’m actually going to get to use it!” Don’t assume your date will have condoms (men can think about sex 24 hours a day and condom shopping will not come up even once); a little planning ahead will spare the two of you the mood-killing effort of hunting down an all-night drugstore. In addition to condoms, you should also carry lubricant, and, yes, there are travel-size tubes at the drugstore. Lubricant is a must with condoms, as it decreases the risk of breakage and makes them feel more comfortable for all parties involved, especially you. And while you’re shopping, buy a little travel toothbrush as well.
Some people I surveyed suggested a few atmospheric additions: If you’re going to his place, take a little travel candle, one that’s in a little container with a screw-on lid, and some matches. Men and women thought a romantic CD merited inclusion, too. One woman, Kathy, learned to “always bring an extra pair of underwear. The first time I spent the night at my boyfriend’s, we left a trail of clothes to his bed, and when we woke up the next day, we saw that his dog had eaten the entire crotch out of my panties! They were just gone. I was wearing jeans, and jeans do not feel great without and underwear.” Duly noted.
THE WORST HAPPENS: MR. SOFTEE MAKES A SURPRISE APPEARANCE. As nervous as you might be to sleep with someone new, remember that men have a lot more to worry about at a time like this. He may be a little too excited and have an orgasm as you slide on the con-dom, which is what happened to one woman I know. ”He was mortified!” she says. “He wanted to die! I told him I was flattered, and that we had plenty of time, plenty of condoms, and not to sweat it. We just kept kissing and everything, and soon he was ready to go again, and then it was terrific. ”
A guy will also be worried that you don’t have an orgasm, or you’ll laugh out loud when you see him naked, or you’re accustomed to really fabulous sex that he can’t possibly match, and sometimes, he’ll get himself so anxious and overwrought that his penis will opt to sit the whole thing out. And in case you’re wondering what happened to the couple who decided to have their first encounter in a ritzy hotel room: The surroundings and attendant expectations proved a little daunting for the man in exactly this sort of way. So they watched some TV, took a bath, ordered from room service, and went to bed – as in, to sleep. “He was great in the morning,” says Alice. They’re still dating a year later. As far as your own pleasure is concerned, it never hurts to draw a general map for the guy – who could use a clue or three – toward your own orgasm-land. You might start with: “You know what really makes me crazy?” and then, by all means, tell him. The women whose lovers had experienced sexual difficulties all added that the guys wound up being wonderful lovers in the long run, so don’t think that your first time together is a reliable indicator of sex in the future. As for the men I talked to, none of them admitted to ever having any “first time” mishaps. (Yeah, right. It’s always the other guy’s problem.) But everyone, male and female alike, agreed that the most important consideration isn’t about personal grooming or where the act will take place, but your state of mind.
YOUR EXPECTATIONS: WHAT ARE THEY, EXACTLY? OKAY. NOW, BE HONEST . . . This critical bit of knowledge goes a long way to ensure the preservation of your sanity and dignity of the morning after the night before. Chances are, you’re hoping he’ll want you forever, with all of his heart and soul, even if you don’t want him in a meaningful way. (And, yes, this is exactly like applying for a job you wouldn’t take in a million years and feeling bad when the company doesn’t call you with an offer.) Contemplating the possibly that he may only see you as a good-time girl makes many women feel unlovable. You don’t ache for him down easy.
So, first evaluate whether you’re viewing this as a giddy romp or as Step On toward cementing the seriousness of the relationship. Let’s say it’s the latter: While it may seem like a scary, bold move, you can avoid further heartbreak if you confess your hopes and feelings to him. You don’t have to make a speech; just indicate that you’re not looking at this as a casual one-nighter. (If you can’t decide what you want, you may want to wait until you can before you hop into bed. If you think sex will help you decide, proceed at your own risk.)
“We we’re fooling around on my couch,” says Carol, “and things were definitely progressing to the point of no return. I was so crazy about him and also so attracted, and I really wanted to have sex with him, but thought I would die if he didn’t call me afterward. Before I knew it, I just blurted it out: ‘You will call me, right?’ I was mortified at my lack of cool, but he looked me right in the eye and said, ‘Oh, absolutely.’ Then I suggested we move off the couch and into the bedroom.” (Postscript: Not only did he call, but two years later he proposed.)
Women believe that if they speak up about their expec-tations, they’ll scare the guy off. If he’s that easily frightened by your stating that you expect some sort of ongoing relationship after the two of you have sex, you’ll at least avoid discovering the wasn’t “thinking of you that way” when it’s too late. Far better to hear the news before you’ve danced the naked limbo.
Another cautionary note: If you think you’re fine with the idea of a one-or-three-night stand, you might ask yourself if you’re really, really sure about that. “I know now that I can’t just have sex with a guy,” says Rose, who’s in her thirties. “I once slept with a guy in the army who was about to be shipped off to Saudi Arabia. He was obviously having some fun before he left, and I thought, at the time, that I was too. But then I wrote him letters and tried to keep up this whole long-distance relationship thing because I couldn’t admit to myself that I was just a one-night-stand.” Be aware of your own emotional makeup: Just because someone else could enjoy this sort of wild fling doesn’t mean you have to force yourself to. Know yourself. Know your partner. And remember to keep your body smooth, your zippered compartment packed and your extra underwear handy.
Oh, and one last tip: If you spend the whole night together, and you’re lucky enough to wake up before he does, take the opportunity to creep into the bathroom. My friend Alicia swears by this move: “I brush my hair, and I take any sort of moisturizer or anything he has in the cabinet and put it on some toilet paper to wipe any mascara away from under my eyes. Hair gel will tame eyebrows. A squirt of toothpaste in my mouth, and I crawl back into bed. Then I wait a few minutes and nudge him awake and yawn and stretch, as if I’ve just woken up myself! One guy said, ‘Wow! You’re incredible. You don’t even have bad breath in the morning!.”
Via
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