How to Have Anal Sex: Without Hurting Her

I’ve received lots of questions asking me how to have anal sex without hurting her. I’ve found that, like I was, many people are nervous and confused about anal sex. So, I decided to write a brief recollection of my experience. It happened about 8 years ago. Although I’m still having anal sex, I don’t do it very often. It’s something I enjoy periodically, but it’s not something I HAVE to do.

So every time I desire anal sex, I usually go through the same steps. So let’s get on with it. Here were the steps I took before engaging in my first anal sex, anal intercourse experience. Take note that anal intercourse didn’t happen within the first few sessions. It actually took a few months before my boyfriend penetrated my ass with his cock. So that’s why patience is vital. Believe me; it’s worth it in the end. It’s also a lot of fun working up to that point.


Before I get involved in any type of anal play or sex really, I make sure I’m clean as a whistle. When I’m clean, I feel more confident, sexier and more ready to get myself dirty. Cleansing usually consists of emptying my bowels, or at least trying. Quite often during any kind of initial anal penetration, I feel like I have to move my bowels. I believe it’s just that.a feeling. So as long as I take of business ahead of time, I know that’s just a feeling and not a call to answer from nature.

After that, there’s taking a shower or bath no big deal. I make sure I soap myself up down there and I usually even stick one soaped up finger in my anus real quick and I know that I’m clean. Just make sure that you rinse yourself good. Leaving soap behind can be irritating to some. That’s the simplest way to clean up and get ready.

Some folks would rather give themselves an enema, which is much more involved. In fact an entire article can be written on that alone. The most important thing about enemas is to make sure you do it hours beforehand so that you’re totally emptied out by the time you play. Also, follow all instructions to a tee!

Anal Play

First, my boyfriend and I engaged in a little anal play consisting of him applying latex gloves, lubing up his finger real good and rubbing his finger around my anus and holding a vibrator, like the Tantus Little Secret (, against my anus. The first few times there was NO penetration whatsoever and I can say that all those extremely sensitive nerve endings are in and around the anus, so even if you don’t experience penetration right away, which you absolutely shouldn’t your first few times around, it’s an extremely pleasurable experience. I found, and still do, that just holding a vibrator against my anus makes my orgasm more intense. Yummy!!!! So no penetration the first time around. We really took our time and enjoyed the process. This  lasted a few weeks.

Finger Penetration

When I was comfortable with anal play, then we moved on to inserting just one finger into my anus. So my boyfriend donned those latex gloves again, lubed up those fingers and as Tristan Taormino, the anal sexpert has instructed in “The Ultimate Guide to Anal Sex for Women( once anything, a finger, a toy, a penis is inserted into the anus, all motion should be paused, letting the receiver adjust to this new sensation and then when ready, the giver can kind of start wiggling finger around a little and tapping on the walls of the rectum. This is exactly what we did and it was so exciting that it brought me to orgasm almost immediately.So much for working my way up, I was finished before I even started. Wow!!!

More Fingers

After a number of sex sessions, which was also at least a couple of weeks and it would also depend on how often you have sex and what kind of time you have for each session, I was then able to accept more fingers. We did the same thing, applied that latex glove, lubed up each finger and then slowly penetrated my ass, then wiggled and tapped the fingers. We applied more lube to my anus before each finger was inserted. You can NEVER have too much lube. Once I was comfortable with that we moved on to the next phase. Now remember, these are totally different sessions of sexual play. I really didn’t move past a step in the same session, except here. Once I could take a couple of fingers, I did try an anal toy.


I tried traditional anal beads first because they were separate little balls, but for some reason I didn’t find them to be as exciting as I had hoped, so I moved on to a butt plug, like this one ( That’s what I needed! I liked the feeling of fullness in my ass from the butt plug. The plug also works really well because it’s made of silicone and can be fully cleaned and disinfected after use.

The anal beads didn’t work out for me because at the time, I was ready for something to be put in my ass and to stay put. The beads were popping in and out and all that activity just didn’t feel good at the time, it was actually annoying.

Anyway, using lots of lube, I slowly, very slowly stuck the plug in my ass. Then my boyfriend, with clean hands, rubbed my clit and then we started having intercourse. Wow, did that feel exquisite while having vaginal intercourse! After a few more sessions, I felt I was ready for the cock.

Anal Intercourse

In order to prepare my ass for this, on the same night, I went through all these steps listed above before I allowed my partner to thrust me with his cock. We used lots of lube, he wore a condom and we took our time. By going through all these steps beforehand, there was absolutely no pain or unpleasantness, only tons of exquisite pleasure. I think that was the most intense, full body orgasm I ever had, ever!

The position that I chose to have anal intercourse for the first time was ‘Woman on Top.’  That may sound odd to some. Many are thinking ouch too deep, too deep! Although true, it wasn’t painful or unpleasant. My boyfriend sat on the bed with his back up against the headboard, he applied the condom, I drenched his cock with lube and straddled him. I, very carefully held on to his cock as I, slowly.very slowly sat down on his penis. In order to help me slide down slowly, my boyfriend assisted me by putting his hands under my ass checks so that if my legs got tired, I wouldn’t come crashing down on him.

I’m not all that in shape or muscular in my legs and I didn’t have a problem at all. I’m rather petite, so that was not a problem for him either. Once I got the head of his cock in, which is in all honesty the thickest part and this holds true for dildos as well, we paused. At that point I was able to slowly position myself so I could come down on my knees while straddling him and then when ready, I could easily slide down onto more of him. The most important thing here is that my boyfriend, as difficult as it was, never pumped, never lifted his body.

He just sat still and allowed me to come down on him. I rode him, that way I had FULL control over the depth and the speed of penetration. He was so excited about the experience that he climaxed rather easily. Once I was on my knees and felt comfortable, I did ride him a bit, while I did that I lubed up my hand, the one that wasn’t touching his cock or was maneuvering around my anus, and rubbed my clit.

The whole experience, which was probably one the most intense that I’ve experienced, didn’t last too long because my virgin behind got WAY too excited and I reached an extremely satisfying climax. After that, it was time to slowly and gently lift myself off my boyfriend’s cock because after orgasm, anal penetration just didn’t feel that great any more.

Some Final Thoughts

Before I wrap things up here, I just want to ask you to please take note that we only fooled around with anal intercourse when we had TIME. If we were only having a quickie, anal penetration was not explored. Anal play was, but penetration took time and that’s not something I was going to rush into. My boyfriend, wanting me to have a wonderful first experience, let me lead the way the entire time so that I would remain comfortable and excited about the journey. He enjoyed it also, seeing me experience all these new forms of pleasure and really getting off on it.

This was all a hot show and experience for him as well. So that’s my story and I’m sticking to it! I hope something within is helpful to you and I hope that you understand that anal sex can be extremely pleasurable  if done with care and patience. Remember, anal intercourse is not supposed to hurt, if it does stop all activity and take things back a step until you’re comfortable. If you have to stop all anal play and resume at a later date. It doesn’t have to be done in one session, in one night it shouldn’t be.

I wrote this article because I wanted to stress that amount of time I took before I actually had anal intercourse and how much I enjoyed and my boyfriend enjoyed the journey there. That’s what it’s all about. It’s not about reaching the final destination but the fun and the exploration that it takes to get there.

I must thank Tristan Taormino and Nina Hartley because without using all their educational materials, I would have rather unaware of all the problem spots and difficulties that come into play when having anal sex which could have resulted in me having a bad first experience and leaving me to never want to try it again, like many people out there.

So below I am highlighting those resources so that you can gain the same knowledge and have an experience that’s as awesome as mine was. I always say…Get educated before you get busy…and my experiences have been very positive because of that.

What You Could Read Next…

External Resources:

* Tristan Taormino’s Expert Guide to Anal Sex DVD ( – This is her newest instructional anal sex DVD. It’s hotter than the others and has lots of updated information and ideas.

* Tristan Taormino’s Ultimate Guide to Anal Sex For Women Book  ( – This book is great to keep for a reference or if you don’t want to watch a DVD featuring anal sex.

* There’s also Tickle My Tush Book from Sadie Allison (, if you’re looking for a more get to the point of it all kind of guidebook.

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My name is Ann Andriani. Since 1999, I've helped millions of folks sort through their questions and curiosities about sex. I hope that you enjoy your stay with me and benefit from my thoughts and sex advice.