Ah, remember the ‘Ode to Anal: The Formative Years‘? I’ve been meaning to write more of that series for ages. Well, I’m bringing it back.

Have you ever noticed that you project your fantasies on people? When I was younger and wanted a boyfriend, I used to fantasize about going on a date with Elijah Wood and having hotsex, or I’d look at a strange man and just think he was hot.

Now, I fantasize about my hand in Elijah Wood’s ass, and when I look at men all I think is “Huh. He looks like he’d let me fuck him in the ass.”

This is really the story of how I got to that point.

Jordin, my first boyfriend, back in the day was obsessed with my ass. Go figure. He wouldn’t fuck me ‘proper’, but he asked on a regular basis if he could fuck my ass.

But even at the tender age of sixteen, I was informed enough to know that he didn’t know what he was doing, and that I would so wind up getting hurt. Also, at the time, I thought anal was gross. Silly me. As you read in my previous OtA post, I eventually changed my mind, and became more and more interested in it.

However, anal sex didn’t come up in a relationship until much later, when I was dating Daniel. By this time, I was not just interested, but fascinated with ass. It had become a fantasy for me, to play with men’s asses. (Now, however, it is an obsession.) Daniel, ah, Daniel let me play with his bum. It was both the first time I was ever, in anyway, inside a man, and the first time anyone had been inside him, aside from himself. It was just a finger, maybe two, but was all I needed to get the ball rolling.

It was, for me, sweet, intense…I felt like I was given a gift, to be allowed to be the first. It was one of the best times of our short relationship. And it was the physical beginning of my bum fun passion.

However, it wasn’t until Franklin that I experienced it for myself. Franklin was the first of the few men who have fucked my ass. See, while I adore my anal, it isn’t something I do with everyone. I can, and will, name every man who has ever been in my ass. Not so for penis in vagina sex. (That list includes names like ‘The keyboard guy in that electronica band from myspace’)

Franklin was fun. We had much love and trust between us (still do) that we were able to do this. Yet, for some reason, the majority of our anal experiences took place giggling and drunk at the end of a late night. Srsly, not a good idea. Invariably, we’d be too drunk to remember lube, and I would cry, he’d stop, and then I’d still want to have more sex.

With Franklin, it was particularly intense, because I truly believed that I would be with no one else, and that this would be something I would share only with him. It was, I imagined, a perversion of how a virgin bride must feel. “Here. I am giving you this - no one has touched me here before. I am yours.” (I was much younger and more naive at the time. Give me a break)

I think this is why I enjoy being given someones cherry. I feel honoured when I’m able to share a new first experience with someone.

Franklin and I had another first - he was the first boy with whom I strapped it on. Oh yes. I went out and bought Babeland’s ‘Bend over Beginner’ kit, which, by the way, sucks balls. The only good thing about it is that its purple. The dildos it came with are very small and thin, which I guess *is* good for a beginner, but man, I felt insufficient wearing them.

The harness that comes in the kit is terrible. It doesn’t stay in place well, and I find it uncomfortable. The straps are always getting loose while I’m using it. It did come with a small bullet vibe, but its just strong enough to be irritating through velvet, and anyway, I’m a bit bigger than most girls, so I tend to wear it a bit higher up so I have better control over it, so I don’t feel it. I actually took that part off, so now its nylon straps around an O ring. It works well enough, but god do I need a better one. I’m an anal artist, and how can I work my craft with such substandard equipment?

Thank god Miss Jo taught me how to make a harness from rope!

But then again, at this point, I’m not really a beginner anyway.

So yes, I got the kit to use on Franklin, and a dream was born. To fuck men’s asses. That’s it. I don’t want much out of life.

We had some good times with that kit. Ah, I remember one time,I wore the harness under my clothes to a brunch my job was having. When I left, I called Franklin and told him to be waiting naked with the door unlocked…and he totally did! We only did it a few times but it fed the need, and damn did I hit the ground running.

I’ll stop with the bad metaphors now.

Coming Soon: Ode to Anal - Sebastian, and what anal means to me