Learning to like anal

I’ve never been a fan of anal. My first experience was one of nightmares. One night, when I was fresh out of college I was raped, repeatedly. He raped every part of me including my ass.

Not too long after that experience, I met a guy and fell in love. Occasionally, he would ask me about doing anal. Needless to say, whenever anal sex was brought up, a big ole “NOOOO!” was the first and only word out of my mouth. I never told him about what had happened to me. Not because I didn’t trust him, but because it was still so fresh in my mind that I couldn’t share the experience with anyone.

But over time as I felt more and more secure and safe with him, I decided to try anal… for him. He hadn’t done it before and I knew he really wanted to. I told him I was scared but that I trusted him.

Like a very good boyfriend, he did his research, asked me questions, and when I was finally ready, we made plans. He was gentle, sweet, loving and caring. Everything that a first time should be. I don’t remember too many details about it, as it was a long time ago. I do remember that it didn’t hurt very much and at some point I got used to it. We never did it again. We were still young and between having an amazing sex life, not like feeling that vulnerable, and dealing with a condom (I was on birth control) and/or the potential mess of anal, anal sex just wasn’t for us.

In the last year of my marriage, I was trying to spice up our sex life. I asked my husband to have anal. He obliged. It was awkward and honestly, it was quite painful (because neither of us knew what we should be doing). But after a few moments, I began to relax into it and the pain started to fade away. Then he came. That was the one and only time we did it.

Skip forward to this year.

I’ve been on a sexual journey to explore what I like and don’t like with a completely open mind. I’ve read some amazing adult contemporary romance stories that had such explicit anal scenes, I couldn’t help but be turned on. So my interest in anal sex has been piqued.

While in a conversation with a friend of mine, I learned that she really enjoyed anal. Since my two consensual experiences were decent, I decided to try it again. I started researching tips to enjoy anal and read several blogs about anal experiences.

Then I went in search of a good partner. Not surprisingly, it’s quite easy to find guys who want to do anal. But how was I supposed to know who would provide a good experience? Eventually, I settled on a gentleman that has been in the lifestyle for many years, is into BDSM and really took aftercare seriously.

After developing a rapport with him, we finally met up. We hit it off and I knew I was in good hands. We went back to his place. Good music, soft lighting, and strong drinks set the stage. A perfect environment for my first time having anal with a near stranger.

Getting down to business

Since we had spent so much time talking about how I wanted to try anal again, I assumed that was what we were going to do first. But to my delight, he suggested that we have a nice good fuck first to get all the jitters out. He was right. After that first orgasm, I was nice and relaxed.

So do you think the next step was to bust out the lube? Nope. Next on the agenda was some serious attention to my deliciously, wet pussy. While he was down there, he cautiously began to play with my ass. A little licking, a little touching. His slight ministrations built up my anticipation. Knowing what we were going to be doing, brought on a couple more orgasms.

It was only after several orgasms, that he took out the lube. He showed me a very slim dildo and squirted some lube on it. He had me lay on my back and bend my legs. And ever so gently, he began to insert it. He didn’t force it in. He watched my face as he slid it in. When he met some resistance, he’d wait a moment until I’d relax so he could slide it in more.

Lying there so exposed with a man would normally cause me to make up some excuse to stop. But he was so gentle and patient that I knew with certainty that even though he was the one doing the actions, I was the one in control. I could say wait, or stop, and I knew that he would. Because of this, I was able to relax and just feel my way through the experience instead of thinking my way through the experience.

On to the main show

After gently getting my ass ready, he slid the dildo out. He had me get on all fours and with a generously lubed up condom on, he began to slowly slide in. He was significantly bigger than the dildo, so with a bit of stopping and starting, I began to adjust to his size. Before I knew it, his cock was balls deep in my ass.

He grabbed a massage wand, put it on my clit, told me to hold it in place. Then he began to fuck me.

With the wand building my orgasm, I was able to tighten and relax my ass in response to his thrusting. With each thrust, I could feel my orgasm getting closer. As my abs tightened with anticipation, I could feel his cock getting even harder, and his thrusting picked up pace. I was so close but I didn’t want to come until he came. So I held on until the moment I felt him tense up.

The moment I felt him thrusting deep, I let my orgasm free. It was so intense. I could feel every part of my pussy contracting as the orgasm continued to roll through my body.

Practice makes Perfect

After such an incredible experience, I knew I wanted to have anal again. And I have. They haven’t all been as mind blowing as that first one this year, but I’ve learned things that I like and don’t like. So for that, I’m thankful for each experience. I’m glad I stepped out of my comfort zone. And I’m grateful that I’ve basically erased the negative associations from my first anal experience.

While anal is not my favorite dessert, it’s on the menu now.