One of my friends asked me for tips about breast play and cunnilingus, and this is what I came up with. After reading it, she said I should put in on Literotica, so here it is. If you have any more ideas, by all means, say so in a comment! We'll all benefit.
Breast play
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-Don't go straight for her breasts as soon as you start kissing; there's no need to rush things, and she'll probably enjoy it more if you take your time. If you haven't had a breastable (yes, I just made that word up) relationship with her for very long, go especially slowly; see how she reacts each time you move your hand a centimeter closer to her breasts, and be sure to get explicit permission before you actually touch them for the first time. If you already have an established sexual relationship, you won't need to be so careful, but grabbing boobs right away still tends to kill the mood. Kiss, put your hands on her back, on her shoulders, on her waist; if she's happily going along with that, then she could well be up for breast play next.
-It's worth noting that everything has its exceptions; if you've had a sexual relationship for a while, playfully touching her breasts out of the blue and then kissing her might be a fun way to start a lighthearted exchange of affection and bodily fluids. I wouldn't try it on a second date, though.
-Like with most other forms of sexual touch, I suggest starting breast play very lightly, barely touching the skin with the fingertips. It arouses that area of the body without giving too much stimulation too quickly, and it's a great way to tease and make her want more. It's also a very soft touch, which many people find sensuous and reassuring.
-When you start using your whole hands on her breasts, be gentle but firm. Massaging/kneading motions combined with squeezing usually works well. (It works well for fondling her butt, too.) If you're doing this from behind, you can easily kiss her neck and ears, and hold your body close to hers.
-All of this so far can be done while she's wearing a bra, but of course it will be even more intimate and fun if she's topless. Do you and she both want that? If you (individually) do and she's not already taking it off by herself, try touching the strap and giving her a questioning look (or the side of it, if it's a strapless bra). That's a good way to ask permission without risking violating her personal space or breaking the mood.
-I hope removing brassieres is easier for you than it is for me, because I still have trouble with that. If you have trouble unhooking it, don't make a big deal of it. Remember, she's probably had trouble with it, herself. This is a great time to share a laugh and realize that you're both only human; it can really help to take the pressure off of both of you.
-It's probably best to stimulate her entire breasts with rubbing, squeezing, and maybe lightly running your fingernails over her skin, before you focus on her nipples specifically. When you do stimulate her nipples, you'll probably want to start gently, as with everything else. Brush your fingers lightly over them, rub them, pinch very lightly, then maybe not so lightly. Some people even like having them twisted; see how she reacts to the pinching before you try that. Yes, some women like a more direct approach and will be happy if you go straight for the pinching, but until she makes it clear to you, I suggest starting light and sensuous.
-Using your mouth is a wonderful part of breast play. Kiss every square inch of her breasts, maybe with licking or even nibbling, before you get to her nipples; try maybe kissing/licking your way around them and gradually homing in. When you do, start with the aureole; aureoles are sensitive and sexy, and overlooked far too often. Try circling its border with the tip of your tongue a few times, then lick and kiss all around her nipple; then kiss, suck, and lick the nipple itself (especially if it's hard). Sucking long and hard can be very pleasurable for many women (and men), and a lot of people even like having them bitten a little bit.
-Remember, there are two breasts, and they both deserve your attention. You can use your hand on one while using your mouth on the other and then switch, or use both hands for both breasts. Just make sure that both breasts get equal attention overall.
-I've heard that some (large-breasted) women like having their breasts pushed together and both nipples sucked at the same time; I haven't tried this, but it sounds like fun, doesn't it?
-Go back and forth between using your mouth and just your hands. This should help keep it going for as long as she wants without her getting too used to the stimulation either way.
-If you have breasts of your own, then I imagine that rubbing them against hers must be all kinds of heavenly. Sadly, I can't be certain.
-Some women's breasts are more sensitive than others', and some women have more sensitive nipples than others do. Be gentle at first and work your way up to whatever you're both comfortable (and pleasurable) with.
Cunnilingus
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-One way to see if she's up for having her genitals touched is to fondle her ass and or her stomach and slowly move your hand closer to her crotch, and watch her reaction as you get closer.