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So, I gave my girlfriend her first anal orgasm yesterday, and since I read this thread a while back, I thought I'd come back and contribute in a effort to help others achieve the same.

We were out drinking last night and started getting a little carried away at the bar, so we left to go somewhere more private.  The moment we got in my car, she went down on me and so it began.  When she does this first, she's always dripping by the time I slide inside her vagina and she often reaches orgasm immediately.  No different tonight but after about 3 quick orgasms with her on top, she unexpectedly took out my penis, smiled at me, and slipped it into her ass.  No lube was necessary, as she was incredibly wet.  She likes anal sex deep inside of her, with slow, short strokes, at an increasing pace.  She was loving it in this position for a while, but I guess the angle wasn't right to reach climax, so I picked her up, and put her on her back.  Same depth, and rhythm, but in the missionary position with her legs up, my penis was putting pressure at an angle where it was stroking the back wall of her vagina.  After a couple minutes, she had the longest orgasm I've ever seen her have and afterwards, it was so intense that she needed a break for a few minutes, then wanted it again. 

I've given her anal sex on occasion before, always after she's had a few orgasms to ensure that she was really in the mood, but this was the first time she was able to get there.  So, I guess I now have some pointers for those trying to achieve the illusive anal orgasm...

1.  Prepare... My girlfriend had decided earlier that she was going to surprise me with this, and she was very clean.  This made her much more comfortable with it, and allows for no unwanted distractions.

2.  Make sure your partner is well satisfied before you start.  It's true it's more mental than physical.

3.  Don't necessarily worry about size.  My girlfriend is only 5'3", and I'm 6'3" with 8 inches to me.  She can take it all without difficulty and actually prefers deep anal sex.  In my case, I think the size and length actually helped.

4.  Use a position and an angle where the pressure is on the back wall of the vagina, in my girl's case, the deeper the better.

5.  We didn't do it this time, but if your partner is very clean, go down on her first with your tongue.  This is a good way to get her going before anal sex if she is nervous at all.  Anyone who doesn't love this should never attempt anal.

6.  Don't force it.  Let it happen naturally and it will.  That's how it happened with us.  The first time we did it she didn't like it but she was putting pressure on herself to try it.  The next couple times were better and tada, 4th times the charm.  So, have a couple drinks, loosen up, and see what happens.

Cheers everyone!

Jesse

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Hi. I've been in just about the same boat as you. Well, I was actually quite aware of anal sex and open to the idea, I just didn't know how to prep myself. I chose to do some online research before I tried anything, then practiced cleansing at home before going for the real thing. I have a really supportive and patient boyfriend, which is a real must. This is what has worked best for me:

1. If you have a massage shower head it will be immensely helpful. You can use the massage setting to direct the water into your anus, which will clean out anything unwanted. As a previous poster said, just repeat until the water runs clean in the toilet.

2. Fleet saline enemas are easy to use and cause very little discomfort. If you just follow the directions on the back of the box you should be fine. I like to shower and use the method I mentioned above after an enema, just for an extra clean feel.

I have enjoyed anal sex from my very first experience, and I think the most important factor was that I was comfortable. If you want to get the feel first, just lubricate your fingers, (Palmers Cocao Butter can be nice) three is about equal to what he will feel like inside you if he is an average white male. Then just relax! It can be really enjoyable if you take it slow.

I hope this has been helpful, and that you will have a good time with whatever you do.

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I'm a lesbian but me and my girlfriend hardly have vaginal sex. Sure we lick each other good, but what we really enjoy is anal sex. And I agree with the guy who likes it kinky and large. I've had some pretty huge stuff up there. My girl loves it when I f*** her with a  huge 3 1/2 inch wide dildo. She just rides it like it's nothing. I love to stick my wet tongue in the gaping hole that's her as****e afterwards. It drives her wild. So  think for everyone who loves being penetrated anally, gay, lesbo or straight, just wash up, lube up and ram into that lush as****e. 

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Thank you everyone for the advice. I had concerns about the best position for a beginner with anal sex, and also about the "to enema or not!" I appreciated the blunt truth and suggestions! :-)

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 How much cleansing is safe?  I'm using a shower head bidet and don't know if there's a limit to how much water you should flush through the anus safely.  

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On ur back ... ur muscles are really relaxed and your not compressing the gluts to keep ur legs up on ur side.
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You don't techincally need to douche or cleanse beforehand but I pretty much always do. It just makes me feel more comfortable. You can get more information at myanaldouche.com

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I saw your post and the many replies and actually tried anal sex with my husband for the first time. We now are "regulars". Here are some lessons learned:

1. Cleanse thoroughly before sex. I've actually tried using a colon cleanser that is used for colonoscopy prep. It worked great, but a simple enema works almost as well and can be used daily.

2. Take it slow. After time, you can build up to a more rapid event, but the first few times, comfort is key.

3. Always use LOTS of lube.

4. The best news is that anal sex is an absolutely amazing act! There is so much feeling in the anal area that the experience is otherworldly. I love the "full" feeling and my husband appreciates the fact that I have so much control over the sphincter muscles. I can grip him so tightly that he can barely thrust. In effect, I can easily control his orgasm. Finally, he is able, due to his long arms, to stimulate me during sex. I can now make him orgasm just as I am doing so. What an experience!

I suppose that the down side of all of this is that we enjoy this so very much that we rarely engage in vaginal sex any more. Perhaps the newness of anal sex will wear off over time, but I can confidently say that it will be a frequent part of our days together for years to come. Thanks for the post! :-)

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I was wondering if by people talking about drinking milk before if they meant bloating or just the idea of possibly having diarrhea...
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For myself I find enemas or douching you never completly can clean yourself. What I discovered was make sure you've had a bowel movement the day of. Then a few hours before anal sex slip a glyserine suppository up the anus just to clean out the lower bowel. Clean as a whistle, lots of lub and enjoy!

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As far as lubrication is concerned, you better off with something edible like coconut oil. If you think it's too thin, mix it with Crisco vegetable shortening, about 2 co:1vs. Warm them up to liquify and mix. It's great for regular sex also. None of the commercial ones are edible.
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i love anal and what works for me inexpensively is the alternative shower nossel,by taking the head off  and rotating the hose in a circlular motion forcing water where it wants to go while placing a bucket for exit material ,semi warm water works great for me,and  another routine i do is fill your self up bend over and tighten those inner muscles making the water flow further up,in saying this youll be surprised how much water in take u can have up inside of you,but you can flush your self out for a good  number of hours ,,remember to rinse till water runs clear,,and a toy to make sure the coast is clear,,and to better prepare you for sexual delight..

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My fiancee and I are very intimate, we explore new things all the time...anal sex is one of them, I enjoy it so much, and he absolutely can't get enough of it, but I had the same problem as you, I didn't know how to get it clean so I wouldn't make a mess, we have done it in the shower, so that the water is a natural lube, and so that any mess we make washes away, but I wanted to take it out of the shower, the only problem is that I never knew how to clean myself there fully, but now I just go in the shower before anal sex and use my finger to clean out any unwanted gross stuff, it prepared me for his penis and made sure I wouldn't be dirty. I totally agree with the boyfriend part, he based to be patient, understanding and very gentle.
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Do da boda stink after anal sex?Homina,homina,homina,homina!

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im not sure what this has to do with anything but im a women and i happen to hate trail mix .
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