Let’s Talk About Sex…in the butt.

Allow me, Modest Minx, to pop! the proverbial cherry on this blog’s entries about anal sex.  Not to take away from the other Dirty Old Moms’ love of “in the butt,” but having had some awesome anal this past week, I wanted to share my take on anal as someone who is still very timid about the act.

As far as my sexual experiences may go, I’m a total newbie to the whole anal world.  As a teenager who was hopelessly addicted to the Interwebz, I met my fair share of pervs (and I say that only because men older than my parents giving a young teen girl sex advice is definitely a perv in my eyes).  To be straight and make a somewhat long story short, this guy was actually a friend of mine on-line.  I recall a time when he told me how great it felt when he stuck his fingers in his ass and recommended that I try it, too.  To be honest, I don’t even remember how we got on this topic.  I was 13 or 14 years old and had never even had sex!  But anyway – being the prude that I most certainly was at that age, I acted appalled and offended that he would bring up this taboo subject and be so open about it.  In reality, or IRL, as they say, my curiosity was piqued.  I experimented when I was home alone, using lots of Vaseline (the only sort of lube I could use without anyone noticing some was gone), and I really didn’t see what the big deal was.  It felt like I had a finger in my ass!  Not to mention the uncomfortable positions I had to get in to reach my fingers back there – positions resembling a human pretzel do not necessarily make for good masturbation positions.  I was fairly disappointed but never researched further and let the whole matter drop for several years.  (I would like to add, though completely irrelevant, that this man eventually named his crossdressing character after me, because it has always somewhat flattered and amused me!)

At the age of 18, my best friend and I traveled to my college campus for a pre-visit the summer prior to my attendance there.  Another good friend of ours already lived in the same city and we stayed with him and a gay couple he knew at their house.  My girl friend and I, we slept on the pull-out couch.  But our friend and the couple all slept in the same bedroom and I raised more than one eyebrow at the noises that erupted from the bedroom that night.  The following morning, one of the guys got up and went into the bathroom.  The noises coming from there HORRIFIED me!  Is THAT what anal sex does to you?  How it makes you feel?  How long does it last (I thought to myself after 20 minutes of this guy in the bathroom)?  I never wanted anything to do with it, ever again.  A finger had been one thing and had been disappointing.  Clearly, a penis was a whole different story and was NOT something I ever thought I’d enjoy.

This memory became one of many in the forefront of my thoughts regarding sexual relations until I was 19 and dating a guy who was fairly on the straight and narrow when it came to sex (you know – receive oral, don’t give; missionary and occasional doggy style; no funny business).  So you can imagine how shocked I was when he whispered, “I wanna fuck your ass” right before he ejaculated on it.  At first, I assumed this was a communication error since he was from Jamaica and often used terms we don’t use here in the U.S.  Doggy style?  Sure…  So I replied, “Yeah, do it!”  He was fairly gentle and used his own semen for lube, so it didn’t hurt at all as he started to ease his penis into my ass – but that’s not QUITE what I thought he meant.  At that point in my college free-for-all, I was still more about pleasing the men I slept with than receiving pleasure myself and I didn’t stop him.  So no, it didn’t hurt as many claim it does but it felt like I was, for lack of a better term, “prairie-dogging” a giant shit.  Over and over and over again until he came his second time that night.  He rushed into the bathroom to clean up, leaving me feeling awkward and dripping from all the wrong places.  I felt shamed and pretty disgusting and vowed not to do it again.

My two closest girlfriends often shared their experiences with each other and gushed about how much they enjoyed a good anal session every once in awhile.  I began to doubt my decision of never.  “Never say never,” right?  I thought Hmmm…  Maybe with someone I was sure I was going to marry… so I could avoid the shame aspect I had felt after the act in my previous relationship.  But the opportunity didn’t come up again for quite some time.

On a completely related note, what makes my boyfriend bi-sexual?  According to him, the different sensations that come from anal play (both ways).  We often engage in ass-play on him but never me.  I would flinch and move so he couldn’t even get near my ass.  But I’m trying to accept the fact that he likes anal play, a fact that I knew prior to the beginning of our relationship so I decided to surprise him the other night.

Well, we got so wrapped up in my other new love (69, anyone?) that that didn’t exactly work out.  But the following night, I made sure it worked.  I had him focus on pleasing me for awhile before I squeezed the lube into my hand, rubbed some on my asshole (okay, I’ll admit – I rubbed A LOT on my ass.  I was kind of nervous) and focused on him for a few.  When I got into the position and he thought it was going to be just another bedtime romp, I told him to aim for higher.  He is a very attentive and gentle lover when the time calls for it and he eased into it (hardy har har) really well.  It felt….good!  No, it felt great!!  Everything I’d read and heard to prepare did not do it justice.  It didn’t feel like a giant shit!  It didn’t hurt or TEAR (my ass hurts just thinking about that possibility) and I was actually able to enjoy an experience my boyfriend had been VERY patiently waiting for.

What was I so nervous about??  Well, possibly that I WOULD tear…or that I’d never be able to shit again…or perhaps that he would pull out and the anal sex experience would turn into a horribly shitty situation (literally) and he would be so disgusted and grossed out that he would immediately leave me for the porn stars that have unrealistically clean anuses.  Um, yeah.  Really.  I was afraid of these things.  Our solutions?  Plenty of lube and a condom.

It’s truly amazing what sexual barriers one can overcome when determined to overcome their fears.  It’s amazing each and every time I try something new, something I had been afraid of in the past, and I discover it’s a new favorite – I was missing out on it all this time!  What worked for me to get to the point where I was willing to try anal isn’t what will work for everyone who is nervous about trying it.  But my advice to those people would be as follows:

1. Use. A. Lot. Of. Lube!!!!
2. Use a condom (Aside from the many STD/Is that exist, your partner can get E. Coli from anal sex as well)
3. Try it with a partner you can trust, someone you are completely comfortable around and you know will listen to you if you say STOP (or, in my case, MORE and DEEPER   )
4. Relax and HAVE FUN!

Ask Dirty Old Moms your anal questions or give your own anal advice to first timers or those re-visiting the possibility after a bad experience.   We love to talk about all things in the butt.