Yes, its that time again. Wendy’s thinking about anal, and her favourite anal partner, Sebastian.

I’ve been thinking about Sebastian quite a bit these days, because we won’t be seeing each other either for quite a while, or ever again, depending. He’s in a relationship now, and he managed to behave in such an oafish and fuctardish way, I’m not sure if the lure of that sweet ass will bring me back should he call again. We’ll see. When it comes to him, I am weak, and this is partially why.

(The other part is the fact that he is my hands down physical ideal. That boy’s body makes me melt.)

Sebastian was the second man I ever had anal sex with, and to date, the only man I’ve slept with who was as passionate about anal sex as I am.

There were many things about our relationship that were wonky. For example, I called what we had a sexual relationship. That, to me, is what it was. He…I’m not sure what he called it, but the use of the world relationship scared him. No matter what I said, he couldn’t quite understand that it didn’t mean ‘dating’ or ‘commitment’.

He often behaved badly, inter-personally, and I let him get away with it because he was pretty.

We hurt each others feelings.

He didn’t care much for cuddling or kissing, which are two things I adore.

He was extremely paranoid about keeping his predilections a secret, while I sing my love of anal whenever I can. (That caused some contention. Srsly. But I ain’t keeping quiet for anybody. Not even him)

He didn’t seem to get that I was not upset by the state of things. We thrice had conversations about how while things were great, I did not want to date him, at all. The only time jealousy ever entered the equation, on my part, was because he was also playing with a girl I had fallen for. I was jealous of him, not her.

I think he thought I fancied him much more than I did.

But at its core, it was basically, one of my most honest sexual relationships. We each knew what we wanted, and what we were getting. We had perfectly complimentary fetishes. He got off on a girl fucking his ass, and I got off on fucking a man’s ass. We both also got off on more traditional anal sex, and we did have some pretty hot PIV sex as well.

We needed each other almost more than we wanted each other, because neither of us are people who could live with out anal eroticism in our lives. Well, I can’t say that for certain on his part, but I think it would be a sad day indeed if Sebastian wasn’t getting his ass fucked on a regular basis.

Within ten minutes of meeting him at my first orgy at Jefferson’s, I had the majority of my hand in his ass.

It progressed rather quickly from there, but that is my first memory of him. Sprawled on his back, cock in one hand, poppers in the other, hair fanned out, with four of my fingers buried in his asshole. It is an image burned in my mind forever, because it was one of those moments where everything clicks into place, and you say “Yes. This is where I want to be. This is where I need to be. This is what I want.” Not him. Ass. Men’s asses. Oh, I knew I liked it, but I hadn’t really experienced it like that before.

I didn’t even know his name at the time, but I knew right there that if I had any say in it, there would be more to come.

Oh yes, there was much more. You can see it all here. We played often, for nearly a year on and off, and I learned quite bit about myself. I learned that I could top, at least when it came to him and anal. I learned that I could fit a hell of a lot more in my ass then I ever thought I could, if you don’t tell me what you’re doing back there. I learned that I could have an orgasm from anal penetration alone. (Granted, it only happened once, but considering I’ve only come from penetration of any sort about three times, that says something to me.)

There was an awesome intensity to our play. We’d get together, and nearly every time it was a clothes ripping, someone getting tossed down on the bed, a dick shoved in their mouth and violated in delicious ways.

Once, we went ass to mouth.

Oh yeah. We went there. Granted, it was his mouth, and his ass, but we went there.

That boy has an ass so clean you could eat Christmas dinner there.

While I have had, and do enjoy light and sweet anal at times, I definitely have a very visceral, animalistic relationship with it. Things with Sebastian, at least in bed, were never sweet, gentle or romantic. There was an intensity, a pressing need that drove us. A very pure, very base physical demand.

Goddamn was it hot.

Sebastian is one of the few men I ever participated in phone/cyber type sex with. Generally, I find those activities boring. I don’t get much out of talking about what you want me to do to you - get your ass over here, and let me DO it! But with him, it was a delicate way for both of us to explore our kink and talk about taking it to the next level.

Large insertions. Oh yes. We would talk about toy’s we’d like to buy for me to use on him, really big scary looking butt plugs that he’d want me to destroy his ass with. He was the one who brought up shopping for big toys, reasoning “If you are going to really destroy my ass, you’re going to need the right tools for the job.”

If I could explain how turned on I was at that…

I’m more of a hands on kind of girl - I wanted both my hands in his asshole. I bet we could have gotten there too, had we had the time.

While we fantasized about taking his ass to the next level, he brought mine a step up as well. He was a man who I might not trust with my secrets or my heart, but my ass was another story. He filled me with cocks, his lovely un-cut bio cock and the silicone ones he brought with him, all progressively bigger. I remember that night well.

It was three in the morning. God knows how we wound up playing that late, but we were, and he had me on my knees, working me with one of his larger toys. I was screaming bloody murder, in a good way, because he found out the quickest way to my g-spot was through my ass. Eventually I had to yell at him to stop. I was wrung out, sweaty, tired beyond all reason. He pushed me right up to the edge of squirting, which I have never done before. I knew I was there, but I couldn’t relax enough to let go, partially because it was *so* intense, and partially, because it was three am, and I was so not sleeping in that wet spot. I had towels down, of course, but I had a good feeling they wouldn’t have helped much, not this time. Not with a dick in my ass, a hand in my hair, and his voice growling in my ear.

That was a good night. I think that was a cuddly night too.

When he left in the morning, he forgot his cock here. It’s always fun to send a text reminding someone they forgot their cock at your house. Though it did give him an excuse to come back over.

Alas, however, all things must come to an end, and I do believe our time is over. I always knew it would happen. I can’t say I’m totally fine with it. Seriously, it is hard to let go to that kind of intense sexual connection; at least for me, since it was my first of that sort. I’m sure there will be others, eventually, but this one, with Sebastian, was a first.

Much like Jordin, my first boyfriend, Sebastian will always have a little place in my heart, and regardless of what happens, I’ll always be able to look back fondly on the times we had. They were very special, and very important to me.