@jdjohndoe13
Lemme help out. Sex is wonderful, and spreading the word so that more people can enjoy it is a great thing.
Cleanliness is paramount, so wash all of yourself thoroughly just before you go—not just your dick (but if you spend some time doing other activities first during the date, washing the dick separately just before the deed is still a great idea just so that it doesn't smell of sweat and pee). Cut and clean under your nails, including toenails, and always,
always use fresh underwear and socks. Use a nice-smelling deodorant and good perfume. Better to have no perfume than a cheap one.
If you shave your facial hair, shave it very cleanly on the day of the date because fresh stubble is very sharp and actually traumatic for delicate skin. Unless your girl is into pain, in which case it's probably fine, but at least make sure you don't scratch her somewhere unnecessary.
Always use condoms. Even if the girl is on a pill, unless you're in a loving and stable relationship, you still don't want to risk anything for either of you. Thankfully, modern condoms are
extremely good; top of the line Okamoto or Sagami stuff is only 0.01–0.02 mm thick (think plastic cling wrap thickness) and is virtually unnoticeable. Don't go for the cheap stuff unless you want to compromise your experience. And since you never know when they might come in handy, always have a couple on you.
Don't leave clothes on during sex, at least if you're doing it indoors. Yes, this includes socks (for some reason, guys tend to forget they exist at all, but it's a major turn-off for most girls). Undress the girl as well, but don't rush there. Make your girl feel like you're in control and aren't just using her to satisfy your lust.
Sex is smelly and messy. Any anal play doubly so. This is something you need to simply accept and prepare for: prepare an extra set of bed sheets just in case, always have both wet and dry tissues nearby, ideally have a separate waste basket, ensure that you can ventilate the room and safely use the shower afterwards. This is particularly important if you're doing it in a house where parents or roommates also live.
If the girl is on her period or it's right about to start, it's best to restrain yourself to hugs and kisses. Having penetrative sex during period is
still possible but, well... yeah, it's uh...
quite the sight afterwards. Been there. Pretty sure you don't want it unless you're both into horror movies and really enjoy the smell of iron.
Foreplay might seem like a very tedious thing at first, but it's extremely important for proper arousal. Eventually you'll grow to appreciate it and likely even find it more fun than the actual copulation. Don't rush getting your hand inside the panties; be generous with caresses and kisses and try to figure out what your girl responds to—there's a lot of surprising discoveries to make there for both of you. I've had one that was extremely turned on by me nibbling on her collar bones. (Do be careful with anything that might leave a mark!) I promise you that being good at foreplay leaves a far better impression than having a big dick, because that's where the difference between an experienced man and a glorified dildo comes from.
Dry fingers on dry skin = yes. Wet fingers on wet skin = yes. Dry fingers on wet skin =
NO. If you're touching anything mucous: lubricate, lubricate, lubricate... Saliva is not necessarily the best thing to use because it's rather thin and dries quickly; if you're playing with the clit, lightly dip your fingers in the vaginal opening to lubricate them until it feels completely slimy. (How to tell if it's slimy enough? Nothing should catch on the skin of your fingers.) If there isn't enough juice there yet either, then just move elsewhere for the moment or gently caress her around the big lips. If she's wearing silk panties, caressing over them can also be quite pleasant (buy her a pair if she doesn't have any!). There are times when you can use a synthetic lubricant, but if a girl isn't wet it's usually a sign that you haven't yet made her wet.
I guess it should be obvious, but
never go inside with an unwashed hand. If you've just picked something up from the floor with that hand, or touched anything dusty, or scratched your butt, please go and wash it, or use a wet wipe if you can't. Ensure that you don't have any dirt remaining under your fingernails; that shit is nasty, mate.
More on topic of clits, their sensitivity varies
wildly from one girl to another. Some wouldn't mind if you nibble or strum it like Yngwie Malmsteen does to his guitar, others won't let you touch it directly until they're close to cumming. You'll have to figure out the right approach every time, but the general rule of thumb is stimulation has to be proportional to the state of arousal. Keep your hands off the clit at the beginning of the foreplay, gradually work your way towards it, and go wild when she's close to the climax.
Experimentation is good, but always make sure your girl feels comfortable with whatever you're doing to her. She might not express it directly, so be on check for situations where she repeatedly tries to move your hands or face away, makes some noises that sound somehow wrong (or suddenly stops making the
right ones). This is a very sensitive subject and people rarely feel comfortable listing what they dislike in fear of upsetting their partner, so you might not receive a sincere response even if you ask directly. Paying maximum attention is always important and will bear fruit in other ways as well.
Don't suddenly make your girl do anything she wouldn't do to you by herself. E.g. if you want her to suck you off and for some reason she just never does, suggest it verbally first and see what she says about it (e.g. some have an easily triggered gag reflex—might as well give up on it in that case). Or, if you want to be more subtle about it, put her in a 69 so that it feels less like a dominating gesture and gives more freedom of expression.
Speaking of 69s, if you don't want to choke your girl, put her on top or on the side (this also helps compensate for a significant height difference). Never do it while standing up, contrary to what you may have seen in porn. And don't do this after taking a shit unless you take a shower or wash up with a bidet. (On this note, bidet attachments for toilet bowls can be had for as little as $30–50 and pay for themselves completely in toilet paper savings over a couple years. Your girlfriend will also appreciate it very much.)
Don't talk or blow air inside the vagina. Don't put anything in any orifice in general unless you're completely sure it's welcome there. How to be sure? If the girl asks you to or gives confirmation when you suggest it. You don't have to suggest it verbally, but pay complete and utter attention to how she reacts.
Be careful with petite girls: don't put your weight on them and remember that they aren't as deep as tall girls. Never put your weight on boobs and stomach in general. Never use boobs as handles.
Don't say anything stupid, start any unrelated conversations, or make unnecessary jokes during the act even if your girlfriend has amazing sense of humor. You'll have plenty of opportunities to do this later.
If you came first, which tends to happen a lot at the beginning,
always help your girlfriend get there with tongue or fingers immediately. Don't leave her hanging! If she comes first, slow down a little—although it's easier for girls to continue immediately after climaxing, brisk pace might still feel unpleasant.
Similarly to foreplay, "aftplay" is a lot more important than it seems at first, as it essentially solidifies the turbulent emotional state you both end up in after the climax. Hugging and kissing ensures that even if you've made any blunders during the act, the overall impression will stay positive. Turning away from your partner or starting doing something unrelated immediately is a major turn-off even if you're the god of fuck. Even if you feel the need to wash up or put the used condom in the basket, trust me, it can wait for a few minutes; sex is about human touch and attention first, and everything else second.