Early on in our relationship, my boyfriend and I decided to have the sexual fantasy talk – an important discussion for any couple. Snuggled up in bed, he asked me, “What’s something you want to do that you’ve never done before?” I didn’t hesitate in responding with, “Double penetration,” because I knew it wouldn’t bother him. I doubt there’s anything I could request that would be “out-of-bounds” for my kinky little bastard.

But he took so long in confessing his sexual fantasy that I was beginning to think he wasn’t going to ‘fess up. Come on! What could be so naughty that someone would actually be afraid to talk about it with me? I’m a nymphomaniac of the kink variety! I’m the most sexually depraved person I know!

“I’ve always wanted to be fucked with a strap-on,” he finally whispered, instantly stunning me into silence. Oh. I can’t imagine what my face looked like (but thankfully, we were facing away from each other, so he probably can’t imagine it either!) I didn’t know what to say. I’d never played with a man’s ass before, let alone fucked it. I tend to be more submissive with men (and save my dominant side for the ladies.) I’m used to possessive, prone-to-growling, alpha males, and my new boyfriend wanted me to hold him down and have my way with him?

Oh.

I finally managed to squeak, “That’s not so bad,” and he rolled over to flash me an incredulous look. “You didn’t laugh at me,” he whispered in awe, and that’s when I realized how big a deal this confession was for him. This was his big secret, the one fantasy he had never shared with anyone before me. I was special.

How could I possibly say no?

But this was passing out of my comfort zone, and not because I’m opposed to asses. (I’m no stranger to anal, myself.) Growing up, I was a tomboy. One of the guys. I’ve worked hard as an adult to feminize myself. I crave to be seen as a girly, delicate creature. Strapping on a fake dick doesn’t strike me as either girly or delicate.

Over the next couple of weeks, we casually surfed the internet and priced different strap-ons. We even measured his dick so we could find a dildo close to the same size. But we didn’t buy anything. Not yet. “Maybe for Christmas,” we both agreed before placing the fantasy on the back burner. (Much to my relief, at the time.) And in my spare time, I read several things on the internet and in magazines about male anal play, and my view of it started to shift. I began to respect the courage my boyfriend had shown in coming out to me about his fantasy, and I began to understand that him wanting me to stimulate his ass was as reasonable a desire as me wanting him to stimulate my pussy. I was still a bit wary of the whole strap-on thing, but anal play in itself no longer bothered me. It even began to work its way into my nightly dreams. Soon I was fantasizing about fingering him, fucking him with a dildo, and even rimming (which is a story in and of itself!)

But my first foray into male anal play didn’t come until a few months later when I was giving Mr. Kinky Bastard a back massage. I had managed to strip him down to nothing, and I was slowly working my way over his back when I decided to head south towards his ass to massage there as well. He moaned and spread his legs for me, and my curiosity was sparked. “Do you want me to finger you?” I asked, and he moaned his affirmation.

It only took me a few minutes to clip my fingernails down to nothing and find the bottle of lube he keeps stashed in the closet. But then I was back in between his legs again and nervous as fuck. My hands were shaking and lube went everywhere – except where I wanted it to go. If he had been so inclined to go sliding down a chute on his bare ass at that moment, he would have been well-lubricated for it. But I finally managed to get some on my fingers and on his asshole and then, well, there was no backing out. I used my middle finger for the deepest reach. And it actually felt good. Tight. Slick (from the half bottle of lube I had dumped everywhere, no doubt.) I slowly worked him up to two fingers, and after a while, when he could no longer stand it, he rolled over, pushed me down, and proceeded to fuck my brains out.

Afterwards, I looked back on the experience and realized, surprisingly, I had really enjoyed it (and obviously he had, too.) He placed a lot of trust in me by submitting himself like that. and I had done something for him that no one else had ever done before. It bonded us on a level I had never achieved with another lover. It made our relationship special. Since then, there have been more fingerings, a little bit of rimming, and several promises of dildo penetration in the near future (and I’m hoping Santa will bring me the strap-on for Christmas.)

Yes, my boyfriend dreams of strap-ons. And so what? It doesn’t make him less of a man. In fact, I respect him more for embracing and confessing his fantasies and desires to me.

My advice to everyone is to keep an open line of communication with your sexual partner. Have a sexual fantasy? Talk it out with them. And ladies, if your man comes to you with a desire for anal play, don’t be afraid or disgusted. Instead, be proud that your boyfriend/fiance/husband trusted you enough to let you in on his deepest desire, and then help him to achieve it. Trust me. It’s not as scary as it sounds.