03 February 2007

The 40-Year-Old Anal Virgin

I'm a firm believer that to fully appreciate sex, you have to have a good sense of humor. And you can't be terribly modest. These two traits are also useful if you're planning on blogging about your sex life. For some reason, ascribing to these beliefs doesn't make it any easier for me to be slightly embarrassed by the fact that Amy's and my initiation into anal sex together came at the behest of watching the comedy The 40-Year-Old Virgin.

The movie is a rarity, in the sense that it's a Hollywood comedy that I find quite funny, even laugh-out-loud at times. I've never gotten into those LCD comedies that have been all the rage over the last few years, like American Pie, Dumb and Dumber, and Something About Mary. I've started watching each of them on pay cable movie stations, but abandoned each for their sheer lameness. So when I picked up Virgin off HBO one night this past autumn, it was on the faith of the word friends whose opinions I respect. Its short length definitely had that going for it. But in all honesty, Amy and I weren't holding our breath for genius.

And while we're talking about low expectations, neither of us figured much would be happening in the sex department that night. It was Friday, always the night of the week when Amy is her most tired, having been wrung out many times by work and the kids. On top of that, she decided to open a bottle of red wine to consume while watching ... a relaxant that I (and probably she) believed would elicit drowsiness rather than horniness.

The bottle was consumed over the course of the film, but -- and this probably speaks to the strength of the movie -- we were both awake and laughing right up to the final scene, a hilarious outdoor dance number performed by the cast, apropos of absolutely nothing else in the story. Amy and I were sufficiently relaxed and punchy to recognize the glory of the moment.

Amy was also sufficiently horny to push me down on my back on the couch and pounce on top of me the moment the credits were rolling. She started in right away with strong kisses from alcohol-loosened lips. Then she was rubbing her body against my clothed hardness. Then she sat up, and off flew the top and the bra.


Back down on top of me, she fed me her tits, encouraging me to bite -- something that, with her still nursing, doesn't happen often (she's usually too sore). So when she requests it, it's a good sign that she's particularly wound up. Well, that and the fact that she then stood up and ordered me to get my clothes off. A few lollipop-sucks of my already hard cock, and she was back on top, hustling me inside of her, and once again feeding me her tits, with that breathy voice right next to my ear, encouraging me to do a good job.

This went on for awhile, and then out of nowhere, she says:

"Don't freak out when I say this."

I froze. What the Hell is coming next? "Okay ...."

"Do you want to try fucking me in the ass?"

You know, I nearly come in my jeans just typing that sentence.

Alright, I thought, that's it. I've died. I'm in Heaven -- and it turns out that Heaven is exactly what I'd always thought it would be: One giant edition of Penthouse Forum.

How does one respond to one of his biggest unrealized (even if it is mainstream) fantasies being offered up ... without even asking?

Well, one responds by summoning up as much import in one's voice as possible, and saying in a quiet, controlled voice: "If you're ready to try, I would love nothing more." She kissed me again.

It was my job to go get the lube and a condom. I mastered time-travel on that jaunt to our bedroom. You can bet I was as quiet as possible too, floating by a sleeping child's room. Because wouldn't it be just perfect right now if one of those little cherubs woke up and needed Mommy or Daddy?

Safely back in the living room, I kissed Amy again.

"So, what do you want me to do?" she asked.

"Get on your hands and knees," I said, and I laughed inside at my sudden business-like approach. I was focused, like those emergency first-responders who have practiced and practiced for a terrorist attack, and now they were finally putting into action what, to date, had only been theory.

And there she was, with her ass facing me. She's good at following direction.

God, that beautiful ass. I couldn't resist kissing the globes, gently biting them, as I knelt on the floor by the couch and flipped the top on the Astroglide. I squeezed a bit directly onto her asshole and massaged the ring for awhile before slipping one finger in. We'd been this far before: Often while fucking Amy doggy-style, or sometimes while going down on her, I work a finger or thumb into her anus. She's always been fine with it.

"How you doin'?" I asked after a couple of minutes of fucking her with a single finger.

"Great," she said.

"Okay," I said. "I'm adding another finger now. Gotta loosen you up and get you ready."

She concurred, and then added: "For someone who's never done this before, you seem to know exactly what you're doing."

"Oh believe me," I chuckled under my breath, "I've done extensive reading and research in preparation for tonight." I must have added the right amount of comic desperation to my voice, because she laughed again.

I lubed up my middle and index fingers and gently pushed in. My free hand caressed her back, her sides, and occasionally swept underneath to her breasts, keeping up a steady stream of stimulation. A few minutes later, I checked in with her again.

"It feels good," she said, sounding a little surprised that two fingers had gone so well. "Try another finger?"

"That's what I'm doing," I said, already adding lube to my ring finger. I took the three-fingered penetration quite a bit slower, adding more Astroglide to her asshole in the process. After a minute or so, she was taking it like a pro. Her ass was also starting to move back against my hand.

I asked, "What do you think? Ready?"

"Sure," she said. If she was nervous, she was hiding it. I know I was nervous. It's hard not to imagine this scenario so many times and not be a little freaked the first time it's happening. I felt like a teenager about to have dinner with the supermodel whose picture is taped to the inside of his locker.

I put on the condom, positioned myself behind her and lubed my cock really well, adding another dollop to her ass. It was certainly in everyone's best interest to make sure that we were not underlubricated. I wanted her to like this. I wanted her to crave this.

The tip of my cock disappeared past her ring.


"Yeah." No sign of stress at all. I pushed another inch in. "Good," she encouraged. I was still nervous.

"Why don't you push back against me at your own pace," I suggested. And instantly I was in to the hilt. Holy fuck. That was much easier than I had expected. Either her ass is made for fucking or I got her primed well enough ahead of time. Hopefully both.

The first thing I noticed was the heat. It seemed warmer than her pussy. The second sensation was the tightness. Thank god for the lube, or I think the friction would have made her sore pretty quickly. Either that or it would have pulled the condom right off. This was pretty intense.

"Are you gonna start moving?" she asked with a smile in her voice.

"Yeah. Sorry. Enjoying the moment." Of course, I kept it slow at first, but shortly Amy encouraged me to pick up the pace -- she was fine.

And before I knew it, I was seriously and intensely fucking my wife's ass.

After several minutes, it was clear that I was not coming anytime soon. Amy even helpfully added some good dirty talk, and I responded in kind, spanking her ass a bit as I laid into it. I don't know if it was the alcohol in my system, or the intensity of the moment, none of the above, all of the above ... but there was no way I was going to shoot my load before she got tired. (My erection was having no problem at all ... I just wasn't gonna climax.)

So Amy offered, "How about I go down on you for awhile?" I realize I was wearing a condom (and in hindsight, it's probably why she wanted me to wear one), but it took me by surprise that Amy, usually so skittish about the inside of the butt, was so quick to offer a post-ass-fuck blowjob.

She wasted no time enthusiastically gobbling me, and I lay there thinking about what had just transpired. By dwelling on it, I came after only a few minutes. The ejaculate sprayed all over my belly, and to no one's surprise, there was a lot. One spurt landed on my shoulder.

I don't really recall what else we said that night, but you can bet "thank you" was uttered more than once. And actually, Amy thanked me too. Her impression was that it was quite pleasing, and that she definitely wanted to try some more of that.

We've tried one other time since. We were in a different room a week or two later, watching some porn when I suggested it. "Sure," she said in her most sporting, GGG voice. The same process followed ... One lubed finger, and then two.... But after taking two for awhile, she said: "I'm sorry, but this isn't comfortable for me tonight. I don't think it's gonna work." She sounded disappointed. We surmised that the alcohol the first time had everything to do with it: Inhibitions and muscles were significantly looser with a half-bottle of red in her.

A couple of humorous items: We've since purchased The 40-Year-Old Virgin on DVD, laughing all along about its watershed place in our relationship. And red wine has garnered a new connotation. When we look at the wines available for an evening meal, we pass on the reds. We're saving one of those for a private night. Soon. I hope.


Anonymous said...

Oh nice, D. Now I know why you've referred to this movie once or twice. That was a true concurrence of lucky events -- the wine, the movie, the more-than-adequate preparation. I think many are turned off by a difficult first experience with anal -- I glad it went so well for the two of you.

I was also extremely pleased to read your description of how it felt from your perspective... that's something I've asked the couple of men who have penetrated me that way, and I've never really been given a great description of the difference in feeling (for the man) between anal and vaginal.

LadyXandria said...

What a titilating tale. I thoroughly enjoyed it.

Odysseus said...

not my cup of tea, personally, but you make a good story. nicely written.

Bekah said...

I thoroughly enjoyed that as well.

Denis Connor said...

LFM -- It's hard to do justice with any words to the difference between vaginal and anal penetration. But it's something I'd definitely like to work on. Now, to arrange for some practice....

Xandria, thanks for enjoying it. And Odysseus, thanks for hanging in there anyway. I'll get something more to your liking soon, I think....

Bekah -- Thanks for commenting when you stumbled upon me. Looking forward to seeing more photos over on your blog.

Christine said...

I miss anal sex, a lot. Sigh... There's is only so much one can do by herself. My current boyfriend barely has a sex drive and I'm on overdrive.

Denis Connor said...

Christine -- Then that boyfriend needs to live up to his end of the bargain! He better be the most amazing guy in the world if he's not putting it to you the way you need it.... (And tell him I said that!)