There is a right way and a wrong way to take a girl's anal virginity, no matter what combination of chromosomes she may have been born with. Doing it the wrong way can be a painful and traumatic experience that can permanently turn her away from anal sex. Done right, though, it can be a wonderful experience for both the man and the girl.

The first thing for you men to remember, and I cannot stress this enough, is to GO SLOW. You cannot rush this! You have to be ready to stop and back off a little, even when you're on the verge of breaking through and making that bitch's ass your own. A little patience and discipline will go far here, and we all like a little discipline, don't we?

For you girls, some prep work is in order. You can't leave this sort of thing up to your man, he's going to be impatient and will blunder about if you don't do your job. A girl's comfort and safety is her own responsibility! SO clean out that cute little tushie with some warm water and maybe a little touch of something sweet smelling. I like to use water for the first couple of rinses, and finish up with a lightly scented douche.

The problem with lubrication is that your tight little ass will clamp down on his big, thick cock as he slides into you. Oh dear, I'm getting a little wet and flustered just thinking about it!! But your ass will act like a tight little squeegee, wiping the lube from his cock so the further in he goes, the less lubricated he is. You do NOT want a dry cock pushing past your inner sphincter ring, unless you're a true pain slut. So what to do?? Read on!

Once you're all nice and clean, you really, really need to do some "pre-lubrication". Your man will probably not know about this, but it's important. You can't just lube up his dick and the outside of your ass and expect things to go well. Use your finger (watch those nails!!) or a slim dildo to work some slippery lube like Astro Glide or K-Y Gel up past your little rosebud, into and past the ring. You will want to lube yourself ALL the way into your inner area! It's not even a bad idea to squirt a little inside. Trust me, the time you spend lubing up will pay off later on.

If you can, get your man to be a little patient and loosen you up with a finger or two before moving in to claim his prize. If he does, take the opportunity to have him push in a little more lube. You really can't use too much here. Too much lube in a pussy will make it too slippery and lose that needed friction, but that's really not the case with an ass, and especially a virgin ass!

It's best to pick a position that will let you have some control over the penetration. Doggy style is good, because it lets you relax and push back onto his cock and gives you an "out" (move forward) if he starts pushing too hard. Cowgirl style is okay too, but sometimes it's hard to relax your ass muscles while keeping your balance. Missionary is OK if you really trust him... but he's going to take what he wants at his own pace, and there's not much you can do about it.

When that big dick first starts to open up your tight little ass, it feels wonderful! You'll feel the head of his cock pressing against your opening. You want to relax and let it enter you, slowly. Pause when you need to in order to get accustomed to feeling it work its way inside. There is an outer and an inner sphincter muscle, and this is where things often go wrong. Getting past the outer ring is usually pretty easy and feels great for everyone. But this is where the man really needs to be able to hold off and let you relax some more. Trying to shove past the resistance of your inner ring will get really painful. Just try to relax your muscles and gently wriggle your way onto that big, hard cock. If you need to, pull off a little way and push back onto it, working it back and forth until you can take it all.

Once inside you your man will want to stroke deeply. Be sure to let him know if it's hurting you. He will need to go slowly and gently at first. Let him know that once he gets you opened up he'll be able to fuck you deep and hard, but it will take a few minutes.

There's nothing quite like that first time when a man takes your virginity and makes you his. It's a time a girl never forgets, whether for good reasons or bad. Make it a good memory for you or your special girl!

There is the pleasure of receiving your man's seed. That can be intoxicating in its own right.
Secondly, your own cock may become very hard and you may beg to be relieved one way or another during or after. I think during is distracting myself, but you may not be given a choice by your man.
Thirdly, you may experience the so-called handsfree prostate orgasm. You will ejaculate in an almost relaxed way. It is very enjoyable and a lot of people choose to call this a sissygasm. Whether you have this or not, you will almost certainly dribble pre-cum as your prostate is rubbed by his cock. Some people seem to have regular sissygasms, many are frustrated because they don't and feel they should. Don't believe the hype, they are rare.
Fourthly, you may experience a different kind of orgasm. Now, some people deny this can happen. Well, they are wrong, as I know from my own experience and from comparing notes with others.
You will feel deep inside you a welling up of sensual delight. Time can seem to stop and you float free of the compulsions of male sexual desire. Sometimes it builds slowly, sometimes in waves. At other times you can go into convulsions, these can be frightening, but leave you washed out with pleasure when they subside. It is difficult to describe these orgasmic states, but you can have one or many during one fuck. The source of these varied feelings is uncertain, but I am sure they don't arise from the prostate. If you read accounts of female orgasms you will find them similar, this includes women having anal sex.
You may wonder why I am putting such an emphasis on this last type. Well, only a minority seem to experience it. If you have these powerful feelings you will find almost nobody writes them into stories or factual accounts. When you do find them, they are ecstatic. You cannot make this happen, but if you are aware it can and have some idea of what to expect, it may happen to you.
In any case, all the responses I have described are a source of joy to a sissy and their partner.