Here are a few hints for having a go at vaginal fisting
This piece is speaking to a woman with a male partner
If that's not you, adapt it a little. It's not hard to do. 

Oh, and I know nothing about anal fisting, so don't take my advice about this as a guide for that.

Choose the right partner.

Unless you know your partner can be trusted utterly to both notice if you are hurting, even a little, and to stop when he does, you'd be best to forget it for now.


Really want to.

This is the biggest factor to be considered in any sexual act, in my opinion. If you don't really want to, it's likely to fail, either physically or emotionally, leaving you both that bit worse off than you were before you tried.


Find the smaller hand.

Most people have a "smart+weak" hand and a "strong+dumb" hand - a few have the smart and strong on the same side, but they are rare.
Establish which is your partner's weak hand. In most right-handers it is the right hand which is less strong and therefore smaller.


Make sure his nails are clean, short and not sharp.

Sounds really really obvious, but it's not simple to remember in the heat of the moment. Dirty nails can spread infection. Longish nails can cut you, and ragged nails with sharp bits have no place near anyone's soft parts.


Lube up.

If you think you might need some more, pour it on.
If you think you probably don't need some more, pour it on.
If everything goes "squelch" every time you move, pour it on. 
If you both need snorkels.... you probably have enough... but pour some more on anyway, just to be on the safe side.

Latex gloves.

Personally, I would find the idea of gloves a total turn off, no matter whether they made things work or not. However, some people say that using gloves makes things slipperier in general, as well as giving added protection from sharp or dirty nails.
Of course, if you are using latex gloves as a barrier to infection against an STD, remember not to use an oil-based lubricant.

Positioning.

It's important that you find a position to be in which is both comfortable for you, and gives your partner free access to you. 
To maintain eye contact try lying supine with your legs apart, as for missionary position sex, while your partner kneels between your thighs with his knees tucked under your legs. This should be comfortable for you, and raises your bottom a little and tilts your vagina slightly downward, making the angles he has to navigate just a little less... angular


What can go wrong.

The primary dangers of fisting are damage in and around the vaginal opening. 
Minor damage can come in the form of tiny tears in the vulval and vaginal skin, tenderness associated with the stretching of the entrance of the vagina and/or with a lack of lubrication, and bleeding caused when fissures occur. 
Severe damage is the actual tearing of the vaginal muscles sometimes leading to incontinence and usually caused by an overeagerness to achieve full insertion of the fist without allowing the muscle tissue to relax and adjust.

Men, on the whole, have big hands. Some men have extremely big hands.

No matter how much lube you use, and no matter how hard you try, how slow you take it, no matter what preparations you make, his hand may just be too big to fit right inside you.

And if it is, trying and trying will lead to frustration.
Now, I know one hears such comments as "If a baby fits through there, there shouldn't be too much trouble with a whatever" but this discounts the fact that during pregnancy and labour hormones are released into ones body which help the tissues to stretch.

Because, on a totally physical level, stretching is really what it's all about.

And if his hand doesn't fit... so what?
It's obvious you have a lover who is at least willing, if not eager to experiment with you. 
You will find many other pleasures to enjoy together :)

And anyway... trying's half the fun.
All in all, Trina's w/u is the best one I've read about vaginal fisting. It is great for beginners, and should be followed if you're not that experienced. There is one thing that can make your first encounter a bit less fear-provoking. It's called a...


Safety Word.



A safety word is basically used to put a complete stop on all action. Ideally, it should be a word that you wouldn't normally use in the bedroom. My favorite is "orange". I do NOT recommend "ouch" "woah" or anything along the lines of "Oh, God! That feels so good."

A different word, let's say "soccer" could be used as a pause word. Especially in fisting, it helps to take your time. This pause word can let you get more comfortable or it can give you the chance to tell your partner something vital. ("I've got to pee", not "I think we should have meat-loaf for dinner".)

So, ladies and gents, bust out the astroglide and enjoy!

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