Your preference & why

Lube, Lube and more Lube, when you think you have enough use a tad more (so i've been told) ;-) x

I've tried that...but it's so painful. ..

I do want to enjoy. It's just the initial penetration that is so painful. I wish I had 2 men making use of both holes at the same time.

you should be the jockey hun take it as you want to then

I'll be the jockey when I'm totally enjoying it without pain

You sound like you are not relaxed enough.
I'd suggest that you get the guy to give you plenty of oral and while he's doing so, he can use his finger to slowly apply some lube and then add some more, working it in well with his finger.
If this is too painful, you shouldn't try and go further.
If it feels ok, then i'd suggest you get onto hands and knees and he enters your pussy from behind while now using his thumb and more lube to further relax you.
If all this still feels good, then get him to place the tip of his penis against your anus, apply some lube to his penis and then while he holds it, you then push back slowly. Don't aim to get it all in in one move, take it very slow and gentle and if it hurts, stop and apply more lube if needed. Once the head is inside, you should relax and just get used to the feeling of it inside you. When ready, push back slowly again.
Depending on his size, you might not fit it all in. When it is inside, get him to withdraw a bit before slowly pushing back inside again. He should take it slow and gentle at first, then when you are used to the feeling, he can then go faster and maybe deeper,

The important thing with anal is to take it gently and use plenty of lube.

If you prefer, you can get him to lay on his back and you straddle him and gently lower yourself onto his penis at your own pace and depth.

I have used this technique to initiate a few ladies into anal sex after they had previously tried it and didn't enjoy it. Your profile says you are looking for thick, long and hard men, perhaps your chosen men are just too big for you anally for first time. Perhaps you can try with a smaller guy?

Hope this helps.

I find it best to be on top at first aswell, so you can control entry. Then move onto other positions when you are ready.
Good luck

Apart from lube, a position to try is on your side. As it reduces tension on the angus. All the other advise is sound little at a time and slow. If you really want to go for it, a vibrator will cause the muscles to be more relaxed , and enters at a speed you can totally control. Try it alone and get used to it.

You should have a look at a well know book from Tristan Taormino (an American feminist and sex educator), "The Ultimate Guide to Anal Sex for Women". It's funny and interesting. You can find it everywhere including Amazon

I've found an anal toy works well too, one that's flexible and ribbed in increasing sizes. Plenty of lube and PATIENCE, especially from the guy. Ease it back and forth as little as you are comfortable with and only try the next stage when you're completely relaxed. Combine this process with your other sex. And with each stage more lube on the way in. Moving it around gently will help spread the lube and make it smoother.

With it all the way in you can continue with other forms of play as you get used to it. If he's not satisfied with this that's his problem. When the moment is right, more lube on his dick, pull out the toy firmly but gently and then he can try to enter you, slowly and at first just the tip. After that his thrusts should be small and slow, gaining ground one step at a time. If you're not enjoying it at this point don't try any further.

As the guy I have found it difficult to stay as hard as possible for the amount of preparation it takes and not to finish too early with the other sex, but in the end it should be TOTALLY worth the effort for him. And having tried the receiving end of just the smaller toy I mentioned, I really appreciate what you girls go through, I don't envy you.

Some good advice..lube..relaxed..much teasing ..stimulation of area..patience...slow...xx

Have you tried using a vibe on your own, start with a finger size and work up , always use lots of lube. Then get your lover to start with a vibe before sliding his cock inside. Xxxx

If it is painful then there is no point really because it is going to put you off each time the word anal is mentioned. And even if you have someone who is more experienced and takes their time with you you are not going to enjoy it because all you can think about is past experiences.

The bottom line (no pun intended) is this: anal isn't for everyone. Some people like it, some people don't, some hate it, some think it gives them more pleasure than vaginal sex. Each to their own.

Like several people have already mentioned, lube is important. Unlike your pussy, your backside doesn't lube itself so you'll have to help it along a bit. Just spitting on it really isn't sufficient and it make actually make matters more painful. A good water or silicone based lube is the best, but anything that will make things slide better will help it to be more comfortable.

You also have to get used to something going up that way. Your body will automatically react to anything going up your backside as a normal reflex. it will tighten your muscle so if you then go and force your way in so to speak it it will be painful. you can get used to it by playing with it yourself by putting a couple of lubed up fingers up your bumhole or even use a small but plug so you can get used to the sensation. Once you are comfortable you can then work your way up to something a bit bigger.

Don't believe what you see in movies where a guy just rams it all the way in. There is a lot (a LOT) of preparation that goes on beforehand that isn't shown in the films.

So to make anal more pleasurable: lube, relax, take things at you own pace and if it hurts or you don't like it then stop. There are plenty more ways to have fun than anal sex.

Like I say you be the jockey hun,take what you want that way