Q: How old were you the first time you had anal sex? And why do ass to mouth blowjobs turn you on?

A: I must have been “barely legal” when I tried it. It wasn’t my idea, but the guy I was going out with then was 15 years older than me and seemed to be very experienced sexually. As I soon found out, he wasn’t. I think we’d been together for a month or two and the anal experiment happened a couple of days before I finally decided that he was a jerk and broke up with him. Anyway, this is how it went: He asked me one night how often I’d had anal sex before. I told him that I was an anal virgin. So he frowns and tells me he’s “surprised” and wouldn’t have thought I was that “inexperienced”. And, he added, he’d show me if I wanted him to. I thought to myself, well, why not. I’d rather try it with someone who knows what he’s doing instead of some schoolboy who’d be even more embarrassed than me. Cut to the bedroom, a couple of hours later. He told me he had to be “really hard” for this to work and made me blow him. He always needed a long time to “get really hard” and this evening was no exception. After more than half an hour of sucking his dick he pulled me up from the bedroom floor where I was kneeling and flipped me onto my stomach. Then he pulled my ass up towards him. I was of course expecting him to fuck my pussy first, but he went straight for the back door.

I was starting to wonder about lubrication, since even a normal fuck is usually uncomfortable if there isn’t enough juice to ease penetration. Before I could finish that thought he literally became a serious pain in the butt. And I mean serious! I was biting the pillow and hoping this was just the penetration phase and things would improve. Of course they didn’t. Then the pain stopped and I realized he’d gone soft again. He was cursing quietly and told me it was my fault, because I was “pushing him out” all the time. He grabbed my head, spun me around and put his dick in my mouth. I was disgusted. Eeek, that thing just came out of my ASS! He pumped my head up and down and told me that he’d give me another chance - as soon as he was “really hard” again. Which - again - took a long time. I salivated like crazy during that second blowjob since I wasn’t going to swallow anything that had previously come out of my butt! This kinda made things easier when he spun me around once again. His cock was now dripping wet and he actually succeeded in pushing it into my asshole while I was chewing up the pillow. There was some lubrication now but it was far from ideal. One thing I was grateful for is that he had a small cock. Not tiny, but slightly below average size. So when he started slamming against my buttocks he couldn’t do any damage and the pain I experienced at first became endurable as I relaxed.

I reached a state where I became indifferent to what was going on and decided to wait it out. Fortunately he came after 10 minutes or so and squirted his load into my ass. I was relieved that I wouldn’t have to blow him again. Especially now that his cock had been so deep inside me. He collapsed on top of me and asked me if I’d enjoyed my “first time”, as he called it. I said, “no”. He rolled off of me and got up to get dressed. I vaguely remember him saying something brilliantly inventive like: “Hmf, well, I’d had better before. You need quite a lot of practice if you want my opinion”. Well, hmf, I didn’t care about his opinion and told him to leave. There is a lesson to be learned from this. First of all, anal sex is something you should try only with someone you really know and trust and who sincerely cares about you, especially if you’re a newbie. As paradoxically as this may sound, anal sex needs to be the most gentle form of intercourse - at least for newbies. If you don’t start out slowly and communicate a lot during penetration it’s simply not gonna work. If you have a ton of experience, you may be confident enough to try it on a one-night stand. But that’s a decision you have to make for yourself. The second thing that needs to be said is that you cannot over-lubricate! Lube up! Lube up! I can’t stress this enough. You wouldn’t believe how many couples fail and never try again because they thought a little spit or a tiny drop of lube would do the trick. It doesn’t. Lube up! Then enjoy. It’s a wonderful experience - as long as you don’t offer your asshole to some fucked up dickhead who hasn’t the slightest idea what he’s supposed to do, or not. So, why on earth, you wonder, do I enjoy ass to mouth blowjobs today?

To be honest - I don’t know. Maybe Freud has some answers. But I don’t consider my sexuality pathological and anal sex gives me a lot of pleasure these days. Quite possibly it’s the relationship I’m in now, which makes me feel cared for and respected. And since I’m a sucker for oral sex the combination of the two makes perfect sense, to me at least. I don’t particularly find delight in tasting myself, but the knowledge that I’m doing the really dirty stuff gives me that extra kick when I need it.