"Now... Do My Bottom."

by Disco

This is my story of how I came to love anal sex.

Jack and I had a friend, I'll call him Coyote. Coyote was talking one day about how he loves anal sex because it's a good substitute during his lady's Time of the Month. Jack and I were both disgusted.

Jack was, at one point, so disgusted that the mention of anal sex would cause him to lose his boner. Anal sex - and Coyote - became a running joke between us for a couple months. Then, one day, Jack says to me "All of this talk about anal sex has actually made me curious about it." And, suddenly, he wanted to try it.

I said to him something similar to what Glitter would say to a man who wanted to up-the-bum her. I said, "You can fuck me in the ass when I can fuck you in the ass."

This shut him up for a couple more months.

And then, suddenly, he asked me if I would actually be interested in pegging, and if I were sincerely interested in pegging, he would be sincerely open to fulfilling my fantasy. Provided I also fulfill his. And thus got me thinking about it. I did research, I watched that episode of Sex and the City where Charlotte is contemplating letting a guy do her anally and the four of them have a whole discussion about it in the back of a cab about five times, I let him start experimenting with rimming and fingers, etc.

So, months and months after this, I was tied up, I was really into the moment, and I told him to just go ahead and do it. Just fuck me in the ass. So, slowly, and gently, and with much direction, he did. It was the first and only time I have had anal sex. It was very painful, but also it was good.

I remember the next day feeling slutty because of it. We broke up not long afterward and I remember thinking, what an awful waste - to give that to somebody and have them leave you. It was, somehow, more important to me than my vaginal virginity.

But then, my dildo became friendly with my ass. And suddenly I loved ass play. Loved it! Didn't have anybody to share it with anymore, but loved it even on my own. I started small, and I got bigger, until I could comfortably fit a whole dildo inside. Initially, it was only an accessory to the real stimulation of clitoral rubbing, just allowing a bigger and quicker orgasm. It wasn't until one day I was cybering with Jack - a cyber in which he told me what to do, and I did exactly what he said, no more no less - when he told me to fuck myself in the ass with the dildo but not to touch my pussy. The combination of what had happened before, doing exactly what he told me, and just the delicious feeling of it was the first time I came from purely ass play.

I never looked back. I routinely play with my ass. I even like anal porn at this point, something I once loathed. And I think the moral of this story is that those things which repulse you, if you open your doors to them and throw away some of your conditioning to be 'pure' and 'good,' may one day bring you deep pleasure. And there is nothing wrong with that.

IMPORTANT NOTE:

Anal sex is a high-risk sexual activity, and is very high-risk when performed without protection. The ass is a very delicate place; rips, bleeding and tears are easily inflicted as well as damage to the sphincter muscles. Many diseases are easily contracted during anal sex. Outside of the possibility of physical damage and diseases, as well as regular STDs and HIV/AIDS, anal sex may be linked to anal cancer. Anal sex should, under all circumstances, be done consensually, safely, and gently, with much proper lubrication. I believe the saying regarding lubrication for anal sex is 'If you think you have too much, add more.' On top of all of this, avoid cross-contamination always. Do not move an object (be it a penis, a toy, or a finger) into the vagina or mouth after it has been in the ass without first changing condoms or cleaning the area, as this can lead to infections &c.