Alright, so I've been in a serious relationship for some time now. About 2 hours ago we just tried anal sex. It went about as poorly as possible. Allow me to explain.

First off, you have to know that, as a really perverted guy, I obviously want anal from my girl. Problem is (well not really) that I am totally in love with this girl and shes comes from a prude/christian background (although she really isn't). Given her background shes never had birth control, and we've always used condoms. As we plan to live together later this year we made a pact to get birth control ASAP and hold off on sex till then (asking a lot).

It turns out, we are both really horny people. But, so far we've stuck to our pact and not had sex. But earlier tonight the horniness just took over and she just jokingly said, "we could try it with my butt." I can barely fathom the libido required for this statement as my gf has never even considered the idea previously.

So she suggested it and then I obviously agreed. Ten minutes later we were ready with petroleum jelly and a condom. Here's where things got sketchy. We had never, ever tried anything anal before so the whole thing was slightly awkward (I had to use my fingers first, that was creeping her out). Long story short, she was very, very lubed up and I was a little better than half-mast (bit over-eager on my part). In any case, we were on a time schedule and when I was only able to fit in about an inch of myself comfortably she called it quits.

Now here's the amazing part, she doesn't seem to be against a second attempt considering our temporary ban on actual sex.





So what should I do differently next time? anyone with experience could you give me some pointers?

Certain lube or condoms I should use? Good postion for this? Any way to make the whole easier/more fun for her?

I heard that the petrol eats away at the rubber...

definatly use more lube and use your fingers next time again. and go very slowly to.

It actually sounds like it went great. What was the problem?

It honestly couldn't imagine it going any better for first timers.

If you really believe it went terrible, you have been watching too much porno. You can NOT just shove your cock in and ram it in and out unless she is disgustingly experienced in anal sex. We are talking months of training here.

Seriously, wack off, and thank the lord you have such an amazing girl. You are lucky as hell man, and we all would kill to be in your "position".

Edit:
Also, get her to masturbate while you are trying to have your way with her ass. She may take some time to get used to that, but I would assume it would make her experience more pleasurable after time.

Which 4th world backwater/private school do you come from (do you even have interwebcest access? ) that you would think that vaseline/PJ is in any way/shape/form a good lube? That you don't know that it is not to be used with Latex?

That typically rubbers have a little notice saying only 'Water Based Lubes' are to be used? Have you read that & figured, "Hmmm... petroleum? That's water innit?" :p

Have you never gone into a store & noticed that PJ isn't with the lubes in the rubber section?

Astroglide or KY, 'k?

Don't get me wrong, I don't think it went terrible at all, especially considering it was the first time either of us had tried it. If anything I guess its just ALOT more difficult to accomplish than anyone ever lets on.

So basically try again but with more lube (KY next time) and go a little slower?

*And don't worry, I regularly praise the lord over how amazing/kickass my girl is, wife material for sure :).

i did it for the first time the other night with my boyfriend, and it actually wasn't that bad. more discomfort than pain. you just have to go really, really slow. i don't have much advice actually...it was way better than i thought it would be but i think that's just the level of comfort we have with each other. plus the 2 glasses of wine and the hard lemonade.

oh, and uhhh...i would advise against the "warming" type of ky...

What you could try and do is say...massage her. like all over, don't just fondle her boobs. do it for a good hour or so. get her really relaxed. maybe a bit of a drink or weed if she's into that? (not too much).

she'll probably more relaxed, more horny after that teasing all body massage. it should be easier to get it in and go well.

Friend, I'm well aware that condoms and Petroleum jelly do NOT mix. We had no intention of actually having full-blown anal sex. It was both of our first time and we just wanted to try it to see if she would be ok with it ("test fitting", if you will). Petrol jelly was the only thing on hand, and when my long term partner who has never given any inclination of attempting anal sex says, "Hey I'm horny, lets just try this." I'm damn well not going to miss the chance.

That said, KY is a def must next time.

Well, I don't have any links (down lower in each daily webpage of j orlin grabbe www.aci.net/kalliste/ ) but that website, if Goog doesn't find any you like has links. It's not being updated so it might take going back in the 'chives.

Goog should find you sites that recommend fingers in first. You might even try to get just a little lube inside first? Though ...have you seen Tucker Max's 'Famous Anal Story'?Maybe over weeks... It can take a while for some. Whereas I've seen a Brazilian quoted as saying, "Brazilians care nothing for the vagina." So, it is possible...some women even prefer it that way? :p

It's not uncommon in some Latin countries for women to save their hymens/avoid pregs that way.

Growing up i used to watch port LONGING to bang a girl in the ass.

My last girlfriend let me do it. It was pretty damn kinky but honestly i must say that the pussy is better. Fucking an ass is pretty fun though.

Friend, I'm well aware that condoms and Petroleum jelly do NOT mix. We had no intention of actually having full-blown anal sex. It was both of our first time and we just wanted to try it to see if she would be ok with it ("test fitting", if you will). Petrol jelly was the only thing on hand, and when my long term partner who has never given any inclination of attempting anal sex says, "Hey I'm horny, lets just try this." I'm damn well not going to miss the chance.

That said, KY is a def must next time.

Ya man, don't listen to the shit talkers about your PJ choice. That is what the doctors use in hospitals when they insert stuff in your ass. Your girl most likely doesn't have any STDs, the condom will still work fine for stopping any cum from dripping into her vag.

Also listen to rabbitweed about the massaging. Being relaxed is the most important part really. She may tell you she is relaxed, but subconsciously clenching her asshole. Deep breaths, thinking about something else etc.

I don't know if girls and guys assholes are built differently, but one time at the hospital, they just threw me up on a bed, whipped my pants down, threw some petro jelly on my asshole, and 3 docs took turns having their way with me, with 6 students watching and learning. :) Good times for a 17 year old guy. It really isn't so painful, unless you are hung like a horse.

I mean, think about times you have passed a huge shit. That doesn't feel good, but it ain't the end of the world, you just gotta stop pushing, and most of the pain goes away instantly.

yeah same..the one thing i leanrt from the perverted sex ed lessons where a fat lady rubbed a cock up and down with a condom on until it snapped.

oh well, do a barrel roll in her pooper next time for ultimate win :)

You need a less viscous lube, and more of it.

When you think you have enough, put 2x what you have on there.

You need to get the inside of her all lubed up too, so reapplication of lube as you're progressing is for the win.

Body control is a must and you won't have a good experience until she figures out how to control her muscles down there.

Petroleum Jelly should not be used as lube. Ever. Get some fucking ky. Start with fingers or toys until she is loosened up enough for you to get in her. For me this is usually 3-4 fingers depending on how slow i want to go. Then take it very slow.

Id recommend fingering her at the same time so she has SOME fun and you get to do it again.

Id also DO A FUCKING GOOGLE SEARCH for a guide to anal sex. Im sure youll find one.

I could give you more, but i need a smoke break BADLY.

You lucky bitch. you got a second shot at it. I didn't even get a first 'cuz my girl did it with another guy and didn't like her first time. Prick.

Petroleum Jelly should not be used as lube. Ever. Get some fucking ky. Start with fingers or toys until she is loosened up enough for you to get in her. For me this is usually 3-4 fingers depending on how slow i want to go. Then take it very slow.

Id recommend fingering her at the same time so she has SOME fun and you get to do it again.

Id also DO A FUCKING GOOGLE SEARCH for a guide to anal sex. Im sure youll find one.

You are like the reverse black hole of bad advice. Why should Petroleum Jelly NEVER be used as lube? As I have said 500 times, that is what hospitals use, because it works very well and keeps costs down.

Also, why should he do a google search, when he already posted here? Guides can't give you the personal advice that only comes from talking to real people. Guides are usually set to ideal situations, not 2 "kids" having a quickie.

He also shouldn't bother himself with fingering. First, a girl can finger herself better than a guy can, especially when that guy is trying to focus on pushing his penis slowly into her anus. Second, if he loses focus on the penis pushing, he is going to fuck up and accidentally push too hard/fast/deep and seriously own her ass.

Mods, please don't consider this spam because I cut/pasted my response from another thread. Its just this topic keeps coming up so often. Here is what I said to someone else a week or so ago with a similar question.........


Obviously alcohol and/or drugs helps. It lowers their inhibitions, makes them hornier, and numbs them up a bit allowing for a little bit more "pain" in the process. After that you have to understand this isn't a 5 minute task. Your plan is to TEASE their ass, so much to the point they'll be BEGGING for your cock. Allow yourself at least an hour of foreplay if you want your ultimate goal.

Start out with either a massage, or having that ass in perfect position in a 69. Massage it, caress it, if she is into light spanking...smack it a little. Remember to keep the heightened sensitivity up by spending a little bit of time on her pussy too. What you are trying to do is mix the feeling of pleasure into the realm of the unknown. Now if you REALLY want this anal bad enough, there is something else you'll have to introduce to her butt before your fingers....and that is your tounge. Don't worry if you haven't done it before, it is NO BIG DEAL! As long as you ain't with some skank and has decent hygeine or has showered recently. You can start kissing, licking, nibbling on her ass cheeks while massaging them with your hands. Do this for a while, letting her enjoy the sensation.

When you finally make your way to her crack this is where the tease really begins. You have to work your way to her asshole slowly. When you finally get there, don't stick your tounge in, just do circles around it, again teasing it. All the while you should still be massaging her cheeks, maybe spanking, and of course occasionally playing with her pussy. Finally start reaming her ass with your tounge. If you started in a 69, you can do the "oopsie" attempt. Going from her pussy, past the taint, that way if you get a negative reaction to the tounging you can just chalk it up later to "my bad, I got lost in the moment". This should be no less than the 1/2 hour mark, and by now you should be getting your cues from her if she likes it. If she is moaning like a banshee enjoying this new found sensation, keep on going.

Once that ass is nicely lubed with your tounge, then go for the fingers. Start out with just one, and do NOT penetrate immediately. Just like before, tease it a little. Just tap the outside of her asshole a few times. You are getting it ready for insertion. Slowly insert to about your first knuckle, and really start working her pussy at this point. Try and time some light spanking with further insertion of that finger. When you get that first one in, see if you can suck on her clit, finger her ass, and another finger in her pussy. Go from 1 finger to multiple, again not rushing it.

An hour of this ass play and she should be begging you to butt fuck her. If you do it right with her sucking your cock while getting her ass ready, you should NEVER need any KY at all in the process. And when the day comes she is such an anal whore to the point where she jumps on top of you and puts it into her own ass rather than her pussy.....you can thank me then. : )

Good luck!

don't use petroleum jelly..

use some other, water based lubricant.

agreed on the no KY Warming Gel..shit burns like a muthafucker on your dick -_-

and..it will burn her to

You sodomized a young Christian girl?!?!

I'll be praying that her dad finds out and kills you. :)

Use your fingers first. Start with one, two, three, then insert. Sounds cheesy but it's the way to go (that's what I heard on the radio anyways).

I live in Vancouver, I wasn't aware our radio stations were broadcasting such obscene messages though. Which channel did you hear it on?

Grab your dick and shove it in as hard as you can and if she screams punch her and say "SHUT THE FUCK UP BITCH".

Girls like the whole dominating thing...

What position did you do it in? Try performing it in the the spooning position, she'll be more relaxed that way...leave doggy style for at least six months of 'hardcore' training/pornos.