My first experience was with a woman who was very tight and had never had more than 3 fingers....(bear in mind that were both lesbian and my hands are actually wide for a womans)
I started most of the time by making sure she was relaxed and very very ready for sex, I had teased her for a day or two at least before hand.
My first attempt was successful.
first ten mins-ish; just oral (standard knees bent position)
next 20 mins of oral; at the same time I pushed my fist against her, just as a medium pressure threat. (should be able to feel/gauge measure her manipulable diameter, i.e. the spongy area that gives way a little to your slight pressure)(not so hard that your knuckles are bruising her bone) (too hard and it will hurt and turn her off, too light and she will not benefit)
she should respond (physical unconscious response) by little pulses and widening(the spongy area under your fist) for the potential penetration.(but don't penetrate, or even part her lips or do anything that may makes her think that you will) if she anticipates it she may clamp up.... just start with the thought that you just want to pleasure her, not test her limits.
she may find (as is normal) that just the pressure is an extreme turn on and almost enough to make her cum or beg for penetration... it's a lot more of a turn on than is recognized by most people.
Okay so test how relaxed she is and turn her on more by adding a pulsing pressure with your fist against her. (if her legs close its too hard if she feels relaxed and maybe pushes back towards your fist that is good)continue.... the moment she feels relaxed and wet, discretely lube your hand without a loss of contact from her body orally.(have it ready between her legs)
(20-30 min estimate, can be up to an hour)take your 4 fingers... and as you apply oral stimulation still, just part her a little and let them rest on her entry for 60 seconds ..then push them into her as far as is comfortable, don't try to stretch her yet. (BIG TIP; never tense your fingers, use the force from your shoulder and tricep, relaxed fingers are so much more comfortable and easy to welcome than tensed hard ones)
Also the formation of your fingers is important too, index finger should be touching little finger (not tense,once in her tightness practically holds them in place) if right handed palm facing left and index finger should be between 1 and 3 oclock upon entry(usually 1), obviously you may have to weigh up her angle as you enter.
so...you have your four fingers maybe an inch in...just hold your pressure against her, continue oral. break the push from your fingers every 30 seconds and relax your shoulder, exit slowly, apply more lube and then enter again... repeat until that is easy and your fingers are going in a couple of inches and you can get a slight twisting motion, only use that to spread the lube on your fingers around her(be aware that too much twisting and too much entering and exiting and a lack of lube will hurt and turn her off... get as much lube inside her as possible..(a lube that is oily and has a staying consistency is usually best) all movement should be based on lubing her up and not trying to make her cum or trying to achieve a stretch yet.
she will naturally let you in further if she is relaxed and lubed and turned on...... just feel her allowances and push them a little, and hold them in place, its like stretching a calf muscle after a run it needs to adjust to your lengthening of the muscle...(power/pressure from the shoulder remember, not the fingers)
At this point i advise that her feet are on(not over) your shoulders and as you give her oral it opens her right up.
Difficult part; so your index finger will usually be between the 1 oclock and 3 oclock still. It will get to the point where your knuckles begin to enter.... (lube lube lube again before you go further in)But as it gets to this point or immediately after, her depth is going to limit your entry and you will need to curly the tips of your fingers in upon themselves......and you need to place your thumb too.
so when the knuckles have gone in once or twice, add more lube(smear it around the knuckles with your other hand or as before) and you usually find that the arch of your hand allows a slight hollow for the tip of the thumb. Add the thumb and push in back up to the knuckles and hold, and continue as before with the applying pressure and holding and releasing a little and then applying again.. (your thumb may feel like it is going to break off and your fingers may go numb... (your fault
you brought it on yourself) as you are a guy i recommend that you spend the day bending your thumb into the middle of your hand and squashing your hand together to practice the necessary restriction in size that will be placed upon it.
so...you feel your very lubed up knuckles almost entering.. you lube some more and continue oral and you hold pressure against her, she will be tight but will relax after 30 seconds ish. As they slide in past her major inch of muscle resistance, the tips of your fingers are going to be in a very awkward place.... (probably the most dangerous point) as if you push to far you will pierce her bowel and if you curl them in in may hurt her.... and any length of nail is going to injure her.(make sure you have filed them down until they have no edge to catch on anything at all.)
Okay.. so as you know when you enter a woman you have two directions to go in.. one direction is in and up and pressing against her vaginal wall, the second is in and back towards her anus..... you should have gone back towards her anus!!!!!!!! and have most likely at some point felt a small rosebud shaped womb entry point....
When your knuckles start going in, start to curl you index, middle and third finger in upon themselves just the last knuckle of them (may want to practice that too.) extremely hard and awkward bit.. hardest bit!
At this point you should be fully inside of her or as near as without being so.....do not twist or do anything silly as if she clamps up you will damage her upon tying to leave.. at no point she she have clamped up... if she has you are doing it wrong and should leave it until another day.
So when you are inside or nearly inside .... you don't want the bony knuckles causing more than minimal bruising so either stay in a position where they are just outside or inside of her bony opening.... that will be most comfortable for her. and just work her bearing that in mind... the pressure on her from inside or out is going to be nice, but the knuckles repeatedly grating on her bony area is going to be unpleasant.
The fleshy joint of your wrist to hand will be bearable once inside and fingers curled and will fell nice as you pull it out of her as long as it is small movements and doesn't keep going past the thumb joint.... and also once inside the movement backwards will be more pleasurable than the movement forwards as forwards will bruise her stomach.
Ask her how she is feeling repeatedly, sometimes a finger in her ass will help her relax more, sometimes she will come like that and others she won't. depends on how stretched she is to begin with... however after the first time it gets easier.
When exiting and relieving her of your knuckles go very very slowly, and watch her face or apply oral to distract. make sure you apply proper aftercare (cuddles ect) because fisting is probably the most intimate thing a woman can let you do..........
second time around, chances are you could fist her standing.... legs spread hands tied to a suspended rope..... just kneeling under her and applying oral and working your way up to a fist... Advantage; she can adjust her hips and angle and can usually really fuck them fully this way.... complete in and out movement of your fist and keeping fingers straight.... and the rope catches her wobbly legs when she orgasms, beware of how much length she has internally though.... a pierced bowel isn't going to be a first aid job.. Whist i fisted my last girlfriend until her feet where off of the floor i knew her body and limits better than my own.
I don't advise working from one finger upwards in the first scenario as it tends to graze and provide too much pre friction.....
my knowledge is experienced based not book based) i would always advise reading up on it as it is a serious subject with serious long term disabilities when done without due care and attention.
BE SAFE AND HAPPY......
