“Why is does everybody want to stick it in my ass?!” – Or something to that effect, was recently asked of me by a very close friend. The once taboo act of anal sex seems to be the trending thing these days. The Boyfriend is obsessed with it.
Since our very first sexual encounter, during post-coital pillow talk (or lack thereof as we were on an ill-equipped, pillow-wise, boat), I had proclaimed that I had no interest whatsoever when it came to taking it up the rear- In fact, I had plenty of interest in exactly the opposite: avoiding it for as long and as permanently as humanly possible. He reacted fairly nonchalantly, he’d been there and done that and it wasn’t that great. Liar.
Whilst he had been there and had done that, apparently it was that great because I soon found out, after getting to know him better, that anal sex was indeed one of his favorite things of all time— fast forward through plenty of discussions, persuasion, encouragement, and promises of endless pleasure (“The one girl I used to do it with would squirt, it was that good”) he finally talked me into trying it out. He was experienced and talked me through how to go about it, making sure my bowels were clean, lots and lots of lube, etcetera…
So I went and bought the strongest laxative I could find in the pharmacy (I’ll spare you the details), and headed over to my guy’s place for some first-time fun. After doing my research about it on the internet and seeing just how many people (women, men, straight, gay, young, old) enjoyed stickin’ it up the butt I had decided that this was something I was going to enjoy. I was pretty excited about my venture, considering how inexperienced I was in most aspects of sexual activities.
We started slowly; one finger, two fingers, three… getting used to things and making it easier for the final member. Lots of gentle ins n’ outs, before the big finale. Once it was in, all I can remember thinking is “ohhh gawsh, feels like I need to take a dump. Nope, now it doesn’t. Now it does.” It was like the unbearable need to go to the bathroom, followed my relief on the pull out and then back to the unbearableness, over and over again, followed by “What is that burning sensation? Why am I burning?!” I thought perhaps it was the chili flakes I’d eaten on a meal earlier, but this happens pretty much every time I have anal sex, regardless of what I’ve eaten previously. It didn’t hurt at all (it was a little tender afterwards but that’s about the extent of any form of pain I can think of), it was just unbelievably uncomfortable. My first impression of anal sex was awful. I hated every minute of it and just wanted it to be over. The second time was not as bad, but I still hated it. In fact, the third and fourth times weren’t much better.
The first time I actually enjoyed it was in Thailand. We were both drunk and, ahem, “elevated” and were having all kinds of sex all over the hotel room. He had bought some lube in anticipation that I’d be willing to try again. I don’t know if it was due to all the relaxants coursing through my blood, or the Thai air, but for the first time ever I was enjoying penis in my ass. We tried again sober and I was back to finding it uncomfortable again. When we tried again I took a muscle relaxant and once more enjoyed it.
Since then I’ve had a few more encounters. Some of which I’ve enjoyed and some of which I haven’t. Once, it even ended in our first argument with him insisting that I’m only doing it to please him and I’ve never actually enjoyed anal sex, which isn’t particularly true. I don’t know why, but anal seems to be a gamble with me, sometimes I’ll enjoy it and sometimes I won’t. I don’t know what the variables are (watching anal porn all day before-hand seems to get me in the mood), but occasionally it’s just plain uncomfortable for no apparent reason. When it is enjoyable, it’s only fun for so long before I start rolling my eyes, hoping for it to be over– which brings me to another point: It’s never over! Butt-sex doesn’t even make him come! I don’t understand what the allure is.
My most recent dirt-road adventure included one of the massive dildos he brought me from Singapore which went in the rear while he went in the front, first time double penetration, for the win– now that, I enjoyed, as did he.
Final conclusion? In my personal opinion, anal is okay. But, taking into consideration all of the effort that goes into preparing for it (making sure you’re clean, it doesn’t hurt, etc) is just too much bother for what you’re getting. The most I get out of it is a different sensation when I play with myself… if it wasn’t for my fingers or double-penetration type shindigs, anal would provide me no pleasure whatsoever. Everyone is different, though.
So those who are looking to explore away from the river and take the dirt-road, I’d say try it out. You might be one of the lucky fuckers who gets to squirt ’cause of it (and maybe someday I’ll get there myself. It’s my only real anal-motivation if I’m honest), you might love it, you might hate it and not want to try it again, you might hate it and want to try it again. Either way, I hope my experience in this field has the potential to help someone else out there. I hope you do enjoy it if you choose to try it out, the ladies on the porno’s seem to have a blast.