Sticking your finger into a girl is one of the most pleasurable things I know. If you put your finger in her mouth, nine times out of ten she will automatically start to suck it, like it was your cock. I guess it’s an instinctive response, and a very pleasurable one. If a girl is very oral, she might like it if you force your finger right down her throat, half-choking her. It may not sound sexy, but if that’s what she likes, why not take full advantage?

If you follow this up by fingering her cunt, you will likely find her nice and wet. I like to bend a girl over a table, pull her skirt up to her waist, yank her knickers down, halfway to her thighs preferably. (I like to leave them on; girls usually find this humiliating, half on, half off.) I tell her to open her legs a little. Then I’ll play with her cunt a while, squeezing the lips together, tugging on them, maybe a little smacking. Then, selecting your middle finger because it’s the longest, you very slowly slide it up to the fullest extent. I like to go right in, all the way, at the beginning, then retrench. I pull back till my finger is almost out of her, then very slowly go back. Because she’s already felt your finger all the way, she is impatient for that again, but of course you tease her. Go maybe halfway, then ease it out again. Do this several times. If she tries to cheat and moves her ass back to bury your finger again, take it out altogether and smack her ass a couple of times and read her a lecture about patience. Then start again. When you are all the way in again, move your finger round and round. Now it’s time for a second finger. This will start to feel more like a cock and she will want finger-fucking, as if it is the real thing. You can indulge her a bit, but remember, less is more, and you should never let her have all that she wants. 

Some guys like to add some variation, for example using their spare hand to play with her tits, pinching the nipples and suchlike. Personally, I feel this distracts the girl from what is going on in her cunt, which is where she should be focussed.

At a certain point you will have to decide whether you are going to give her a reward or no. She will certainly be receptive to any approach to her clit, but only if it is done right. I’m not going to read you a lecture here about the technique of clit-pleasuring. Suffice to say that hopefully you have learned just how she likes it done and, after all the teasing, finally let her have the satisfaction she craves.

I’ve saved the best bit for last: putting your finger in her asshole. If you don’t know a girl really well, you might not find her receptive to this. If not, get to know her better and tell her about all the lovely things in store once she loosens up. If you have worked with her already and got her receptive, then a real treat is there for both of you. First, of course, is to use plenty of lube. In fact you can’t use too much. You might prefer to begin with some oral attention. Spread her ass cheeks and lightly touch your tongue to the little hole, circle it several times until she feel it relax just a little, then push your tongue against the hole as if you were seeking entrance. Of course neither the asshole nor the tongue is adapted to this, but it will feel good, and you may sense the hole is getting looser.

Now put some lube on your finger, probably not the biggest one to start with. Don’t rush to put it in. Instead, run the finger round and round, progressively applying slight pressure. Eventually just press the very tip against the hole and force it just a little, until just a bit of your finger goes it. This is your foot in the door. Keep working on that, renewing the lube as required, going just a little further, up to the first joint. At this point, some guys like to bring their other hand into play, working the cunt, even finger-fucking. Again, I don’t favour that because it detracts from what you are doing with her asshole. Concentrate on that. Still using the finger you started with, go deep little by little, still working more lube up inside her. Hopefully before long the finger will be in all the way. Now you can decide what comes next. It may be you try a second finger, it which case it will be the middle one, and her asshole will need to be relaxed for that. Once both fingers have fully penetrated, she should be ready for some proper finger-fucking of her ass. Start gentle, but some girls will get very excited and want you to work up to some rough treatment. Just remember, the ass is a delicate place, even if she is mad for what you are doing.

Very few girls ever learn the trick of getting an anal orgasm. Mostly they need the clit to be worked to get satisfaction. At this point you can provide that, and earn her eternal gratitude. Some guys like to work the clit with their mouth, while still finger-fucking the ass. That can be very good, girls have told me. Or let her have her vibrator, if that’s what she wants.

After she’s cum, she might be willing to let you please yourself with her, offering you her cunt or ass for your cock, whichever she prefers. She should be nice and relaxed and in the mood. I get great pleasure from ejaculating deep in her ass and then watching my semen dribble out. If I’m feeling obliging, I’ll scoop up a little with my finger and feed it to her. You’d be surprised what slutty things even the nicest girls will do when in the mood.