Ideally, you'd like to make that initial pickup push work for you again and again. It's what you do with her undivided attention — away from prying eyes and back at your pad or hers — that will determine just how often she'll come back for more.
Since you can't glean these details through observation at a bar (at least, not at the bars I go to), here's a typical evening that not only ensures her repeat business (or pleasure rather), but will make her want to please you from that night on.
First, the night, then the analysis.
Welcome home
Upon entering your very cozy and tasteful pad, you take her coat and offer her some wine. While you're getting that and putting on some soft jazz, she looks around a little. This prompts you to offer her an "official tour," which ends back in the living room.
You dance with her to the soothing tunes, running your hands and then just your fingers over her back, then neck, while you take in her scent. A kiss follows as surely as day follows night.
You move to kissing her neck, behind her ears, and under her chin, then you bite her neck gently. You compliment a body part of hers that you find especially attractive, then give it lots of attention with your lips and tongue. You suggest you finish the apartment tour, leading her into your bedroom, where you light some waiting candles.
You undress, caress and impress...
Changing gears
Her breathing speeds up, you remove your shirt, then, after a while, hers. Having moved the music to your bedroom stereo, you continue to dance for a while, until moving on to the bed seems natural.
You massage her shoulders and neck with a scented, edible oil that lets you kiss and lick her on sensitive zones that don't usually get the attention they deserve: her ankles, the backs of her knees, the nape of her neck.
Changing gears
Her breathing speeds up, you remove your shirt, then, after a while, hers. Having moved the music to your bedroom stereo, you continue to dance for a while, until moving on to the bed seems natural.
You massage her shoulders and neck with a scented, edible oil that lets you kiss and lick her on sensitive zones that don't usually get the attention they deserve: her ankles, the backs of her knees, the nape of her neck.
You start to tease the undersides of her breasts with your fingertips, then her nipples with your tongue and a slight nibble. You gradually hone in on her butt, then her inner thighs, brushing across her vaginal lips as you move from one side to the other and back.
You suck her vaginal lips, penetrate her with your tongue, and then move your finger inside her as your tongue moves to her clitoris. Inside, your index finger hooks upward toward her belly button, moving back and forth as you massage her G-spot, while you gradually increase your intensity on her clitoris in response to her reaction.
Playtime
Now that she's beyond "warmed up" and has actually reached "hot and bothered," you fetch some ice cubes and let them melt as you trace them across her body.
The suspense has peaked and she can't stand it anymore. You tease her vagina with your member, and then finally enter her. In keeping with the mood, you keep it slow for a while, occasionally changing positions from front to rear to side entries. After so much warming up, you enjoy an extensive session of lovemaking.
The sexual breakdown
Now let's examine what you did to make her so hot.
1- You arrive groomed
Before you ever have sex, make sure you're properly groomed and smell good. It all starts there and frankly, none of what follows will work if you stink. If you've just come from work or aren't feeling 100% about the odors you're emitting, you can always suggest that you start things off with a shower (this is not recommended on the first sexual encounter).
2- You set the mood with music
Music is key, and jazz or trance music are generally your best bets. These musical genres make you look both cultured and sensitive, and you can vary the type depending on the woman and the particular evening's mood. In general, don't choose anything too jarring: some Billie Holiday or soothing sax from the swing era (Lester Young, Ben Webster, Coleman Hawkins) are general lady pleasers, as are any of the CDs from the Serve Chilled series. The music will not only put her in the mood, it will muffle her moans, making her feel less shy to do so and enjoy the experience even more.
3- You compliment her
An original physical compliment is very powerful, but mean what you say.
You lit those candles, used your hands and ate your pie...
4- You caress her with your palms and fingertips
The back and neck are very sensitive areas and great erogenous entry points. Caressing and massaging such entry points is key to being a gentleman and heightening sensitivity in more explicitly sexual areas.
5- You dim the lights/light candles
This will help her if she's self-conscious about her body, not to mention that candlelight is just plain romantic any way you slice it.
6- You undress slowly
By this I mean that you pull articles of clothing off slowly (socks first), and you don't rush to do so. There's something very sexy about being all worked up but still partly clothed. Also, she'll be much more comfortable removing clothes that seem to be getting in the way rather than acting as protection.
7- You massage her
Like caressing, massaging proves you like her body so much that you want to touch it all over — not to mention that it feels great.
8- You give her oral pleasure
Women love guys who love to give them oral. Move in to the area gently and softly, and make sure to respond to her. It's okay to ask her about her preferences, especially for less demonstrative women.
9- You get kinky
Blindfolds, ice cubes over her nipples (or wherever you want to excite her), feather tickling, and tying her up are all options. Be your intriguing self and you'll pique her interest to try out new things.
10- You keep intercourse interesting
While you obviously know there's much more than just the missionary position, don't be too eager to try every position in rapid succession and record time. Remember that women get turned on by repetitive rhythm — just like men, but more so. If you change positions too frequently, she'll never have the chance to get into it.
It often turns out that a position that's good for one partner is good for the other — the physical sensations and excitement are mutually stimulating. You'll know when you've found that sweet spot. Go with it for a while.
One such position that I've found often leads to a sweet and intense spot is the Supported Doggy Stretch. To get into this position, your woman starts off in the doggy position. Place your hands on her waist and lift her legs up so that she can wrap her feet around your butt (for a picture of this position and many others, sign up to The Player's Lounge).
Although this may be difficult at first, the sensations this position provides are enough to keep you going, or coming, as the case may be. In this position, I recommend that you penetrate her slowly and deeply.
11- You make her orgasm
Remember that for women, the mind is the biggest erogenous zone. Compliments or comments that show her desirability, such as: "I've wanted to do this since I first saw you/all evening" will turn her on.
If she doesn't orgasm from penetration alone (and of course many women don't), you can always manually stimulate her clitoris while you penetrate her from behind.
In the end
All of this is just one possible scenario, and obviously you have to be able to improvise. Those who cannot are simply not player material. But the underlying message is that, just like investing, if you give a lot at the beginning, the interest will come easily enough. Remember; givers get asked back and often end up getting their fair share too.
