Its not going to be painless but you can use lubracation to make it a lil more comfortable until you exercise your anal area.

There is a product called "anal Ease" go to local fun store. And buy some good lube while there.. Make sure you tell him going down the dirt road isn't like normal. Start with only the head VERY VERY slowly. And he's only going to be able to use half of his penis probably... Well unless he's got a foot then about a quarter of it. Make sure he realizes this is a very slow ordeal gently in and out. NO PUMPING of any kind. Also try different positions. I have used the normal missionary position with success from her. But you can also try normal doggy style, or standing on the floor and lying over the bed.... Hope this helps. and remember it is still a good idea to wear protection when doing this if it's a casual thing alot of diseases are transmitted by this.

Make sure he uses a good quality water based lube, such as KY (regular..not the heating one) and have him start with using ONLY his little finger. If he also goes down on you and then works his pinky finger in after starting the attention to your clitoris..and getting you aroused to begin with...it will probably help a lot. He needs to keep his finger movements slow and gentle..I mean REALLY SLOW.....until YOU are wanting more of it. He will probably also need to keep in mind that if he wants to have this little adventure...it needs to be ALL ABOUT YOU AND YOUR PLEASURE...until YOU are comfortable, aroused, and both physically and emotionally fully willing to move towards him using his penis there. If he is fairly large, you will probably want to "practice" with him only using his finger...and moving up to his larger fingers or even two after several times of SUCCESS with just the pinky one. This is not something that most people are comfortable "rushing" into...he has to give YOU time to get used to it physically and to learn to associate it with having an orgasm.

Preparation is the key... Ok the embarrassing part... You need do to an enema... Either give it to yourself or have your b/f give it to you. Once I got over the stigma of having him give me the enema it sort of becomes part of the foreplay. Ok once that is over and you've gone to the bathroom here is where the fun begins. You as the girl who is going to let him up you from behind now get to be totally receptive. You lay on your side, pull your knees up exposing your rear totally to him. He starts with a well lubricated finger and he gently goes in and out. This serves two purposes... 1) it gets you used to something going up you back there. 2) it relaxes and loosens you. He continues with two fingers and maybe three. All of this is slow with lots of lube. You just get to lay there and enjoy the feelings. There can be some embarrassment if you have not had a guy doing this to you before but just relax... he wants in you and will do this gladly for you. After the fingers have him switch to a vibrator and if you can afford it have two sizes. Once that is smaller and one that is bigger. Again these are well lubricated and he slips them in and out of you gently and slowly. Finally it is time. I suggest you get on all fours and he comes at you from behind on his knees. The first time will be more like a chance to slowly slip it in you and not much "pumping" will occur as you will be sore... If you are relaxed and lucky then yes he can slip in and push up you aways, slowly of course listening to your reactions. It might take doing this a few times to get used to it before it can really become sex... I mean my first time was more like exploratory surgery. He prepped me.. slipped the head in about 2 inches and that was enough... The next night we did a little more and finally on the third night he was pumping and I could take it. It was about the 4th time for me when it became truly pleasurable. While I loved the feeling of having him go up there it wasn't until he'd done it 4 or 5 times that I actually had a climax from it.

Do not use Anal Ease or any numbing agents: Read this post. It tells you what you need to know about anal sex: http://mflife.wordpress.com/2006/10/12/anal-sex-101/

This is something that will definitely have to be worked on, don't use any numbing agents, that helps him, not you. you could actually have serious harm done to your rectum. starting w/fingering and working on putting more than one in at a time might help, but make sure he makes you cum before you even start this. after a woman comes her endorphin levels rise considerably which can allow her to see something pleasurable as opposed to painful. if he really wants this, he will take the time w/you to make it pleasurable for you too, if not, he isn't worth it and don't bother wasting your time on him.

hey it must be a new craze going on with the guys wanting anal, my advice is to prep yourself while hes playing elsewhere just poking yourself with your finger, guys don't realise how painful bum sex can be if your not wet enough, i find it really turns them on while they watch you do this, hey just be patient though, the first couple of times i did this i couldn't walk for a few days after, yeah you'll get used to it.

well first you need to be relaxed and ready and use a lot of lub, also he needs to be very very slow and paiant ok, john

I wouldnt use any anal ease or numbing products as this will dull the sensation aand pain in the area... you need to know if its hurts and stop if it does... you just need to start real small and use alot of lube and have alot of patients ... even buy a small dildo and play with yourself, if you know what you can and cant do this will make you far more confidient and more relaxed when you are dooing it with you BF.. for instants if you work your way up to being able to take a dildo the size of you mans penis then you aint going to worry about taking it... then you will really enjoy yourself..

Go slow and prepare yourself in advance... as someone earlier said you should give yourself an enema... use lots of lube on both him and in your ass... you can do the standard on all fours which is nice but another way I have found to work is to be in the missinalry position on my back with my legs spread and have him do my ass that way he or I can play with my clit making it better for me... hope this helps and o it may suck the first time or two but keep at it

foreplay and some rim. it,s your first time take all the time you need. while you two are at it start to feel up each other,s bun,s hey,what a soft touch.! lube and a finger at a time before you know it, you are relaxed. next get on top because you control point of entry because you want too.! another butt lovin couple!!