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Yeah, I'm interested in learning how you escalate, pwscottiv.
I never really get any practice with oral. I used to think I shouldn't because it would make me seem like a beta male. I really like the your "But I AM going to have to eat your pussy..."--lets her know you're still in charge. Brilliant.
OK, so first, you need to make sure that your finger nails are trimmed down and smooth. I've had complaints when I've forgotten to do so. Another thing that's also very important, actually the most important for the whole process, is to calibrate the amount of pressure you're using (i.e. when you're licking her clit and when you're fingering her g-spot). You'll almost always want to start off using very little pressure. When she's on the brink of cumming, if you apply a relatively large amount of pressure, you might be able to give her the best orgasm she's ever felt in her life. IF you apply too much pressure too soon (like if you get impatient and are trying to force her to cum) she could push you away and refuse to let you continue. I'll repeat, do not try to FORCE her to cum. The goal is to tease her and make her WANT to cum to build up a lot of sexual tension and then get her to release it in a tidal wave all at once.
So, assume at this point I've gotten the girl into bed by one of several methods... And I've escalated the kissing and touching and at a minimum everything above the waist is off... Sometimes I've just taken the pants and panties off in one motion because they were resisting having their pants taken off at all, but I usually am able to get the pants off and leave the panties fairly quickly.
From that point, I run kisses down her body... Starting at her neck, spending a decent amount of time at her breasts, her sides (flanks) (which are more sensitive than you'd think), and belly... I also keep going back up to kiss her higher, so she doesn't think I'm only just going down to her pussy... I've had several girls try to pull me back up if I just make essentially a line of kisses toward her pussy.
Once I get down there (panties are probably still on at this point, but not always), I kiss her inner thighs, eventually almost "accidentally"brushing up against her pussy (possibly still through the panties). Oh, also, this is a REALLY good time to, umm, "smell the roses" if something doesn't smell "right", then you can always go back up and stop the escalation without embarrassing her. The couple of times that's happened, I told her the next day in a very empathetic and compassionate way. Honestly, every girl gets yeast and bacterial infections, even if she's not having sex sometimes... And sometimes girls don't even know it.
Anyways, at this point if everything is good down there, I'll go to take off her panties... This is usually where I experience the most resistance. You can use the standard LMR techniques or, what I've found very effective is the whole "I'm ONLY going to eat you" tactic. Most girls convince themselves, that it's not sex if there's not penile penetration, so let them think that's as far as it's going to go... Because, once you get the panties off you're almost always golden (almost always).
After you get the panties off is a VERY good time to ask her if she has EVER had any sort of STD and to find out when the last time she was tested. The reason this time is so good to ask, is that by taking her panties off, she's pretty much resigned herself to at least having you lick her. If you ask before this point, it could potentially break the mood she's feeling and make the LMR more difficult to negotiate.
From there, I spend at last a couple minutes just building up to actually licking her pussy. This gets girls super hot. I just kiss all around the general area (inner thighs, lower belly, etc) and occasionally "accidentally" touch either my nose or tongue on her pussy.
The first real licks are VERY gentle... Just barely touching. I do many of the licks all the way from her vaginal opening up to just past the top of the clitoral hood.
After about 30-60sec of that I start licking with more and more pressure, still NOT at all focusing on her clit, but occasionally licking it "accidentally". This includes circling around her vaginal opening and licking/sucking her lips.
After about a minute of that I start focusing more on her clit. I try to keep the same rhythm of about 60 strokes a minute to start out. What works really well is to NOT lick in just one place. Have your tongue hit at a little bit different place each time... This helps to make sure you don't desensitize one area and it feel much better for her. What's important is to keep a regular rhythm. I keep this pretty slow rhythm going till just before she's about to cum.
After a minuite or so, then I'll put my index finger (first finger) in her all the way to the knuckle and sometimes pump it in and out a few times. Depending on how she reacts, I might do it only a few times or maybe like 30 times, it just depends on if she really likes it or not (some girls don't really have relatively much of a response to just having a finger going in and out of them) Sometimes I continue licking her clit while I introduce the finger and sometimes I'll stop licking... It doesn't seem to matter a whole lot.
While contiuing to lick her clit, I'll start rubbing her g-spot, or just a little bit deeper than it. The g-spot feels somewhat spongy and is the size of a walnut/plum. It's about 2-3 inches deep or most of your finger. I use the same technique on the g-spot that I use on the clit... Use a constant rhythm, but vary the location of your finger for each "rub". Use a "come hither" finger movement (like you're trying to pull her to you). Remember, do NOT use too much pressure too early. EVEN is she looks like she wants more... The goal is to TEASE her right now... NOT try to make her cum... Like I said earlier, if you try to make her cum too soon, it will probably ruin the experience for her. Much of the calibration you need to do is based on experience, but you can be nearly 100% sure that you aren't ever going to go too slow... So when in doubt, go slow (as far as increasing the amount of pressure you are applying to her clit and g-spot).
After that, I'll continue licking her clit and rubbing her g-spot, with the method I described above (constant speed, but varying the location slightly for each lick), except I'll also start varying the pressure of the licks and g-spot "rubs" as well. You want her to want your tongue and finger. I've noticed that many girls will push their pussy towards my face when I reduce the pressure of my licks... So I continue to tease them with the reduced pressure and occasionally "accidentally" give them a lick that's a bit harder than the others... Each one of those "accidental" licks usually elicits a pretty decent moan from most girls. I also use a little different pace for my finger and tongue to make it seem like a lot is going on down there all at once... For example, my tongue might be going at 60 licks per minute and my finger might be only rubbing at 30 per minute. For many girls, if they haven't cum already, they will very soon. Do NOT try to escalate the pressure/speed too fast. Let her cum on her own. If you're doing this correctly, 99% of the time the girl IS going to cum quickly.
If 5-10 minutes go by using the preceding technique and she hasn't cum, then you can try increasing the speed and pressure... I've found that it's better to increase the speed of licking her clit (and NOT increasing the pressure very much) and increasing the pressure I rub her g-spot with (but NOT increasing the speed).
When she starts to cum (which with some girls occasionally difficult to tell, because they're so quiet about it), then I usually increase the speed and pressure to a pretty high degree. I lick as fast and as hard as possible and rub her g-spot with maybe 3 or 4 times the pressure I had been using. If you do this before she starts to cum she's going to pull away from you super fast, cause it's going to be painful for her... But if you do it right when she tenses up, she will probably have the best orgasm she's ever had in her life.
Women are very similar to men with respect to them becoming super sensitive after they cum. I'm sure you've had the experience of a girl giving you a hand/blow job and rubbing you for too long after you cum... It feels kinda lame... And you stop her. Therefore, if you want to make her cum again (I had an ex who I made cum about 30 times in a row once using this technique), then you need to avoid rubbing her for too long. At the same time, you need to make sure she gets every last wonderful muscle contraction... So from the time that I increased my speed and pressure to 100%, I start slowing down over the period of about 10 seconds, but you'll need to calibrate for the girl obviously, because some will have a longer/shorter orgasm than others. I never take my tongue off her clit and I leave my finger on her g-spot, even when I've slowed down to the point where I am no longer moving either (within about 10 seconds after her first contraction). It's better to slow down sooner than later.
I leave my tongue and finger there without moving them for at least 30sec. And then, to gauge how sensitive she is, I will move either my tounge or finger just ever so slightly with VERY MINIMAL PRESSURE. If she doesn't jump or jerk, then try a bit more. The goal her is to stay BELOW that threshold where it's going to be uncomfortable... You do not want her to feel like she wants to push you away.
Also, as a side note, by this time your finger is probably "stuck" to her g-spot... By applying so much pressure for so long, I think most of the vaginal fluid is pushed away from the surface... The skin over the g-spot is able to move, so eventually your finger is staying on one place, even though your finger is still rubbing the g-spot... DO NOT try to remove your finger from the surface forcefully. If you want to fuck her after the first time she cums, then wait a little bit and rock your finger back and forth to re-introduce her natural lubrication onto the area below your finger or it WILL be uncomfortable for her.
Back to giving her multiple orgasms... Slowly increase the speed/pressure back to where you were licking and rubbing her at a somewhat slower pace. You may escalate faster this time, because most girls cum faster on subsequent attempts... Just remember to definitely tease her for a while to re-build the level of tension in her body.
You can use this technique over and over and over, but realize that the more you stimulate her, the more sensitive she'll be after each attempt. Therefore, you'll need to be much more careful when calibrating how much pressure/speed you should be applying.
Typically, on the first time I'm with a girl, I make her cum like this 2-3 times, wait a bit for her to recover and then fuck her. Then I'll wait for both of us to recover and fuck her again, depending on the night, sometimes that goes on till way past when the sun comes up. If you're interested in seeing a particular girl more than once, then this technique is guaranteed to have her cumming back for more.