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Rank: Rookie Scribe
Joined: 7/11/2008
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and our first tries have been painful...
he tried using his fingers in the shower,
sometimes it would hurt..
any ideas?
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Rank: Moderator
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Lube!! Lots and lots of lube!! And I cant stress that enough! He must also have tons of patience!
♥ Listen, touch, and look around in the air and on the ground. If you watch all nature's things, you might just see a fairy's wings. ♥
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Rank: Lurker
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and you have to relax.
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Rank: Forum Guru
Joined: 2/9/2008
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Location: Miles From Nowhere
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Try analeze....it is a lubricant designed for anal sex...it has some numbing qualities to it that will help with the initial entry....just dont use too much or he won't be able to feel anything...lol.
And yes....patience...and LOTS of foreplay....it helps if you are really aroused.
~~Tech
~~Tech
Two wrongs don't make a right, but three lefts do...
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Rank: Forum Guru
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Relaxation
Inebriation
Lubrication
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Rank: Lurker
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Nothing else to add here, just do what they say, and remember: don't try what they do in the pornos. He doesn't have to slam it home like they do. Excite yourself and your pussy and maybe you'll both get off to the different sensations.
And try the "three times" rule. If you don't like it after trying it three times, don't do it anymore. You have that right.
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Rank: Advanced Wordsmith
Joined: 7/1/2008
Posts: 75
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For a great anal fore-play, ask him to try a little oral-anal. It lubes everything very nicely and It is very exciting. Also if he can't bring himself to lick you there, then he doesn't deserve to put his dick in there. 
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Rank: Active Ink Slinger
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PLay with his ass in return. Once he knows what feels good in his ass he will be more accompanying to yours.
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Rank: Lurker
Joined: 11/30/2006
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1. I don't do brown-eye on a girl. It's just not my bag. And yet, I do enjoy anal on a woman sometimes.
2. Despite what Cosmopolitan said, nobody plays with Rocco's ass. That's not my bag, either.
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Rank: Advanced Wordsmith
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Me thinks Rocco has some issues. LOL 
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Rank: Rookie Scribe
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I like what you said gfire =)
and ALSO.. what if he doesn't want his ass played with?
=(
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Rank: Rookie Scribe
Joined: 7/15/2008
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First you mus be wanting to
use pleanty of Lube
use Oral Anal to relax
Find the position that feels the best
Go at easy, until your comfortable with it
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Rank: Lurker
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Welcome, Gfire and Dog. Nice to have you with us. Heck of a subject to debut with, but we're glad you're here!
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So I've been hesitant but when my bf did this he used oil and lots of it. Worked like a charm :)
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Rank: Moderator at large
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Don't feel that he has to go for your ass straight away.... if he goes down on you while gently fingering and lube-ing your bottom, then fucks your pussy for a while till you really get relaxed and into it, (he could GENTLY but firmly use a well-lubed dildo or vibe in your ass as he does this... THEN go for your rosebud with his cock....... If you're totally relaxed and aroused it's easy.... He should tongue your ass first.... If he wants it, you need to know he loves it...
Don't make too much of a big deal of it.... Let him prepare you over time and when you feel you really want him to take you there let him know....
Missionary with your ass slightly in the air is a good way to start because you can hold his hips and make sure he's being gentle enough...
If he really knows what he's doing he can enter you there without being 100% tumescent, (hard) which will be easier on you and get fully hard after he's inside you....
When he's there and working it, make sure he doesn't ignore your pussy and clit with his hand...
Or make sure YOU don't!!!!
Also, I find that talking to her really helps.... First tell her how beautiful she feels there and how beautiful she is.... Invariably, as she gets into it a little bit of dirty talking can make things interesting.... It's a sliding scale.... Beautiful Girl... Naughty Girl... Dirty Girl... Little Whore.... (Whatever works!!!!)
Just DON'T ever go from the Back Door back to the Front Door!!!! That causes problems, even if you've douched your backyard throughly beforehand... (Which you should have!!!)
Final thought.... I wouldn't try it in the shower until you really know what you're doing.... Have a few drinks or whatever you do.... Make sure he romances you and you feel comfortable, secure, loved and really horny.... Don't rush it..... Don't say 'tonight's the night' 'cos that creates expectation and nervousness.... Take it s l o w l y......... (And don't worry.... When you get good at it it's like Rodeo!!!!)
Works consistently for me....
xx SF
(Next week on Dr. Stephanie's World Of Sexploration We'll Be Talking About Stem-Ginger....) LOL!!!
"I would do anything for love, including the thing Meatloaf won't do... (In fact, I sometimes insist upon it...)"xx SF
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".... It's a sliding scale.... Beautiful Girl... Naughty Girl... Dirty Girl... Little Whore...." Hahah Stephanie 
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Lube, patience, foreplay, lube. Lube. You can't just stick a finger in whilst in the shower, and baby oil stops working with water.
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chefkathleen wrote:and you have to relax. I agree. whatever "system" you wanna use (fingers, dildo, lube) nothing will really work until you feel absolutely relaxed. So I guess your partner should nor rush in (unless that is what you actually like, of course) and calmly enjoy the new experience with you. The longer it takes, the better it will feel (at least that how it works for me).
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Rank: Lurker
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I will have to keep all that was said here in mind. I would like to try it sometime but the women I know wont let me due to my size.
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Monocle wrote:Relaxation
Inebriation
Lubrication I would add desire. you gotta WANT to try it to get past the first time.
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Sparingly and gently use enema of warm water to cleanse but not hurt or over clean. Next, fill enema with half coffee and half whiskey and then get comfortable on your side preferably and take all that you can slowly and hold for as long as you can. Let this relax you and then, lube and slow play will get you where you want to be. : )
Torture the data long enough and they will confess to anything.
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myself wrote:Sparingly and gently use enema of warm water to cleanse but not hurt or over clean. Next, fill enema with half coffee and half whiskey and then get comfortable on your side preferably and take all that you can slowly and hold for as long as you can. Let this relax you and then, lube and slow play will get you where you want to be. : ) I thought the "Half coffee/Half whiskey" thing sounded interesting so we tried it and indeed it works.... But we've been told we're no longer welcome at Restuarant Antonio..... LOL!! xx S
"I would do anything for love, including the thing Meatloaf won't do... (In fact, I sometimes insist upon it...)"xx SF
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Rank: Lurker
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Try wearing a butt plug for an hour or two (or even the whole day - its a bit of a weird a feeling at first but it feels good and definitely help you get in the mood) before you plan on doing it and yes use lots of lube too!
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Rank: Advanced Wordsmith
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Location: LA, United States
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yes the butplug is great first have anal sex
i am kimyy love hang out with pplz but u ignore me all the time and send me friend invite i dont know u going get delete soo fyi mosty u guys keep try add me to firends go away
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Unless you are totally cumfortable doing it then dont because you wont enjoy it.Just before give yourself a nice long warm water enema,it will clean you out as well as relax you and make things easier..If he wants to fuck your butt then make him let you his,,buy yourself a strap-on and make him give it up if he wants to do you
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All the above advise and turn about is fair play if he won't let you do his ass with a strap on then no go!
Bunny12
 Bunny Rabbits cute and fuzzy they want to love you but they have razor sharp teeth - don't piss them off!
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Real talk, its going to always hurt if you don't completely relax... I advise LOTS of lube and some chill time. Also, and I can't stress this enough, take it SLOOOOOOOOOOOOOOOOOOW. Also, like Bunny12 said, you should get something in return! If he doesn't agree, neither should you!
TheSexiiEbonii ;)
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So, obviously, this is simply what has worked for me and getting my wife comfortable, but it's a pretty pragmatic approach and let's me know whether my wife is physically ready for anal. I am sure there are some gay bottoms that would disagree, but just because my wife can sometimes participate in anal sex, does not mean she can always do it. 1) Start with one finger and some good lube while giving her head. I prefer probe thick. Its the thickest water based lube that I have found. 2) Slowly work it in in timed movement with fingers or a toy in her pussy. If she has fantasies of being in a dp sandwich, this should be great for her. 3) Depending on the size of your toy collection, you might have something that will be a good next step. Basically as soon as I have one finger, I will try either a fav toy, or a second finger, again, slowly pushing it in. 4) If the 2nd finger, or a dildo/vibe that is similar size (maybe a little smaller) than my hard cock goes in there without pain or complaint I know I am good to go. On top of that, it usually does not take long for her to have a pretty intense orgasm from getting dp'd and licked at the same time. I have found that the anus (or at least my wife's anus) is very unlike her pussy in that it really does stretch out quite a bit during play and sex. She'll start off feeling VERY tight, even for a single finger, but often, by the end of a session, my dick (been a while since I measured but it was 7.5" when I was 18) goes in and out easily, just as easily as her pussy. And on top of that, she enjoys a good pounding once we're there. Good luck. 
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Dont just go for it! Lots of foreplay, lots of lube, start with 1 finger...Gently! then 2 then try for it go slowly, remember to realx...Have fun but if you dont like it babe, dont do it!
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Good anal play is learned and gradual.. it should happen over a period of sessions and not just the first time right out of the box.. literally.. tongue.. fingers.. beads.. plug.. vibrator.. and then cock.. it should be an anticipated pleasure for both of you.. and the best lube for anal is olive oil.. it slides easily.. and it's edible.. but always keep in mind it is the ultimate privilege you are offering him.. make him honor it..
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