The Anally Challenged

So….Anal sex.  Yeah, I was never really interested.  It looked painful. And kind of dirty.   Not in a “ooh that’s too naughty” sort of dirty but more of a “that’s not very hygienic” sort of dirty.  But after 10 years of turning around and exclaiming, “Hey! Wrong hole, buddy!” I decided that I was ready to take on a little anal action.

Why the change?  What made me think, “Hmm, a cock in EITHER hole might be really hot,”?  Erotica.  The written word is a beautiful thing, isn’t it?  Something that sounded painful to my uneducated mind for all of these years all of a sudden became desirable and sexy.  My husband thanks erotica everyday for my constantly growing desires in the bedroom.

But it wasn’t as simple as jumping right in.  How could it be?  I KNEW it was going to hurt.  I mean, come on.  It’s not like there is any natural lubrication back there.  And how did we begin?  I felt like I needed a beginner’s manual.  Fortunately, there are numerous people on the internet that want to educate the world on how to have enjoyable anal sex.  So I Googled the shit (no pun intended) out of the subject and made a mental plan.

First we started with the dirty talk.  You know; where we TALKED about me taking it in the ass.  Not gonna lie.  It was hot.  Still is hot, actually.  Dirty talk is fabulous.  Post for another day, I think.  The talking went on for months.  Because let’s be honest.  I was scared shitless (again, no pun intended).

Then the husband took off on an extended business trip.  And let’s just say I was bored.  And horny.  A bored and horny me is apparently quite adventurous.  Out came the anal lube (that we had bought but not used yet) and the vibrator that I (we) never used.  I took my time and holy fuck.  It was amazing.  Not only was it amazing, it was fun to tell the partner in crime what I had been up to 😉

Finally the business trip was over.  We tried a couple times with the vibrator and both found that double penetration is wonderful indeed.  But our vibrator is smaller than the real deal and it took a few more months before I decided I was ready for the next and ultimate step.

And then I decided that I was ready.  We made a trip to our local sex shop and bought some toys to ease our way into the final phase.

This one for me: 

This one for him:

I should really see if the Partner in Crime will write his review on this not so recommended product…

And this for us:

These calmed my overly OCD tendencies….

On the big night, we used the Tushy Teasers.  They were meh for me (we might discuss later how they were for him).  We skipped the plugs and moved to the vibrator and then…holy shit that hurt!  Yeah, we did it.  We took our time.  And I was fine until the last couple inches.  Then it just hurt like hell.  And I was getting tired and wanted to be done.  Poor partner in crime was more than willing to keep going slow and was very encouraging.  He is awesome like that.  But it hurt and I am a big baby so I made him stop.  Well I did let him come first – I am such a giver, right?

All in all it wasn’t a horrible experience.  But it wasn’t a good experience either.  And I definitely learned a few things.

1) I enjoyed it (until the end).

2) I think that I want to try it again.

3) I need to be less ambitious and work my way up a little more slowly.

4) When we do it again I will be sure to use an enema before hand.  Yes, it was recommended to me and I decided to ignore that advice.  Never again.

So at this point I still consider myself anally challenged.  Not forever though.  We’ll get there again and I am determined that next time will be a 110% success.

2 thoughts on “The Anally Challenged

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