Well first is you need to relax about it. The best thing to do is keep your mind off of it all together, he needs to make you cum a few times buy oral or whatever, when he is munching down there tell him to put well lubed finger in your ass, then as you lossen up a lil try two. after he he can get these in with ease you should be relaxed back there. Now as he tries to insert his well lubed penis keep the distraction going with clitoral stimulation.

Great answer so far. Id like to add that some annilingus may be a good start off too. Once he gets to using his penis, go slow and he should thrust VERY! slowly with VERY! small motions as its working its way in. You almost cant even call it thrusting, its more of a gentle wiggle. This will take a good amount of time and may hurt a little or feel weird until it loosens up. Keep talking to each other and let him know how your feeling and how the speed is going. Do what you feel comfortable doing and have fun.

handyman11 and sassafrass gave good answers. I will reiterate two things: relaxation and lubrication. You should use plenty of both. One mistake a lot of guys make is that they go too slowly when pushing their cocks in. Your b/f should NOT push his cock in gently and slowly, as nice as that may sound. He should make sure you're both well lubricated and that you're ready to go, and then he should push his cock all the way in in one steady movement. Have fun, and good luck. It took my wife a few months to get into anal sex when we were dating, and now she cums like crazy when I ass fuck her, and she loves it. You will, too.

Sure it will fit... it will just take time... I personally love anal sex and the orgasms I get from it are actually more intense than those I get vaginally. Here's how... First one answer said: Relax. That is extremely good advice. We are all hung up on how "gross" and "dirty" our rear ends are. As a girl you are about to let a guy up inside of you there... it can be a little nerve racking and embarrassing. So relax... Prep... I know this sounds gross but if you are going to try anal sex, do an enema. Get a regular fleet enema from the store and follow the directions. If you are daring let him give you the enema. My b/f turns it into a doctor/patient game and I'm of course the patient and I get a very thorough anal inspection and enema... all part of the prep Once clean, prepare. This is where it is good to be the girl. You get to just lie there and let him slip fingers and dildos up you back there until you are nice and relaxed. I love this part. I usually lay on my left side with my knees up and let him get access. He starts with well lubricated finger, then two, then three. We have a small tube with a long tip he can slip up me to inject more lube and he pushes it deep up me with his fingers. Then he goes to small vibrator then a larger one. The prep is easily 15 minutes, sometimes more if we are into it. Then I'm ready and he's ready. I get on my hands and knees either on the floor or on the bed and he comes up behind me. This is the embarrassing part. I push like I'm trying to go to the bathroom and he pushes in at the same time. This is one good reason for the enema... you don't want stuff magically appearing at that point!!! But still I sometimes pass a little gas or air as I push.. It is embarrassing but just laugh and know that what is going to come will be worth it. Once he gets the tip in he has to take his time and go in slowly... there is air and you are tight. More than once I've had a guy push in too fast and it hurts and you make rude noises as the air comes out... Thats embarrassing too. But if you take your time he'll be in you and he can even go full length but that is your call on comfort. I love the full length feel and I get him to reach his hand around to my clit and while he is pushing up me from behind he gently massages my front and wow oh wow... it is great. I let him cum in there. Some girls don't and some have never tried it. First thing it feels a little wierd. I can feel him ejaculate and hit my anal walls. I like it, my best g/f while she likes anal doesn't like that feeling. The worst for me is the feel of the cum when it does finally come out. Usally I'm sitting on the toilet when it does and it jsut feels kinda slimy. No having anal like doesn't leave you spread open and unable to hold in gas and poop... well i'd say that I'm more likey to let gas slip after anal sex than I would be if I hadn't had it in a while but my point is you won't be losing control of yourself. It is enjoyable. It is giving a guy the most private of places in your body. Jen

i used a graduated lobe butt plug (see link below) on my g.f. paired with light and intermittent clitoral stimulation during insertion. once it was fully in, i made her come with more clitoral stimulation while i stroked myself and came all over her ass cheeks. that was it the first couple of times. once she was comforatable with that i brought her to the brink of orgasm the same way, slowly removed the butt plug and inserted myself, SLOWLY, gaining ground, then backing out partly, and pushing further in. no hurry here, and plenty of lube. we're at the point now where i can just lick her ass and pussy really good, apply some lube, and sodomize her directly. she has some great orgasms this way, so do i. be prepared that your b/f will get way into it at first, wanting it all the time or coming very quickly. make sure he satisfies all of your passions in the process. wash with soap and water soon afterwards. you may find you want vaginal sex very soon after finishing, so you want to be ready. http://store.babeland.com/butt-beads/ripple

Lube. Lots of lube and have him work a finger, then an other and an other in. once he has at least three in then have him lube himself and go for it! Remember some girls just can't take it!!