Let's Go Offroading!!

I grew up in a town highly populated by Hispanics and subsequently, Catholics. The mentality of most of the girls that I went to school with was that their virginity was supposed to be "saved" for marriage. Many of them belonged to "promise" groups where they would pledge to remain virgins until after their nuptials.

My town also had a high teenage pregnancy rate, so I'm not sure how well those pledges were working.

Oddest for me was the day that I was discussing sex with a group of my girlfriends and another girl chimed in about how she thought that we were being vulgar for speaking in public about having sex. The look of condemnation that she shot us was amusing to me since her boyfriend and I had grown up on the same street and I knew that she was no angel herself.

Having mostly male friends comes in handy when shooting down snooty, self-righteous bitches.

See, Ricky (my friend, her boyfriend) had told me that they had indeed had sex. He came to me one day with a strange look on his face and asked to speak to me privately. As we were kicking at the concrete fence of his backyard while standing in the alley, he looked up and finally blurted out:

"Have you ever asked a guy to fuck you in the ass instead?"

The funniest part of that phrase to me was the word "instead." After we talked more I discovered that his precious angel had balked when he pressured her for sex. She insisted that it was important to her that she remain a virgin until she was married. He felt rejected but relented to the situation. It was then that she turned to him and said that there was another way that they could go about things.

Yes, his little angel turned him into a back door man that night. After asking me if I had ever been poked in the rear, he then asked if he could technically claim that he'd lost his virginity. I really didn't know what to tell him. At the time I'd never gone that route. I'd had plenty of vaginal intercourse, but I'd never let anyone drive on my back road.

The next time that I was with my boyfriend, I asked him if anal sex was something that he wanted. He looked as confused as I did when Ricky disclosed his info to me. "Do you want to?" he asked. I shrugged. I was never one to turn down trying a new experience. Up until I had talked with my friend, anal sex had never even crossed my mind. For being an experienced girl, I was rather stupid in that area of knowledge.

So we proceeded to try. Condom firmly in place, braced in doggy position, I thought it would just be easy as cheesecake. Come to think of it now, cheesecake should never be referenced with anal play. The insertion was a problem, I kept wincing and jerking away and finally he gave up. I chalked it up to something that I just wasn't built to handle and settled for the already fun-filled "normal" sex that I had already been having.

It wasn't until I turned 19 that I was asked to give it another go. It was a new boyfriend and we'd been dating for over 4 months when he finally broached the subject. Apparently one of his first girlfriends had been one of those good little Catholic girls who would only let him fuck her in the ass. He hadn't had an opportunity for another good fudge packing until I came along. Being that I had been open-minded with our sexcapades up until that point, he'd finally felt comfortable enough to ask me to oblige.

We ended up in a very similar situation, only this time full insertion was achieved. I was not the happiest of campers. By the second stroke I was insisting that he cease and desist. He pouted, groaned and pleaded for another shot. I crossed my arms and shook my head. I figured I had made up my mind about anal and decided in that moment that it wasn't for me.

That was... until Bi-Boy. (Gotta love D. He was also the one who introduced me to my first threesome for those of you who didn't read that post.)

One night after seriously partaking of the herb, D started to service me orally. Not being a fan of the act but also being rather incapacitated, I allowed him to do as he so pleased. And as he so pleased happened to be rather pleasing to me. I was relaxed and comfortable.

Then he decided to add a finger. Well, three fingers. That's right. The boy laid a "shocker" on me.

My mind was too hazy to argue. I lazily swatted at his head and asked him what the hell he was doing. He kept his head buried, his tongue working and did not answer. His hand moved slowly, the fingers probing softly. My mind started to race.

"I like this. I shouldn't like this. Why do I like this? No. No. No. No. I don't like this. I really... um.... shouldn't.... yeah..."

While arguing with myself inside my head, I had one of the most intense orgasms that I'd ever had up until that point. My muscles went crazy, my vision went black and the waves of bliss rolled over me. I had discovered that I might very much indeed enjoy having my ass manipulated.

After that, I wanted to have the shocker employed every time. Why? Because it damn well WORKED every single time. We eventually progressed to anal sex, but this time there was no flinching from me. I had been, according to D, "broken in properly" by then.

I still enjoy anal play to this day. It is the way to push me over the edge if you have been working for awhile and stalled in your progress. While I prefer to have "normal" sex, anal is something that I will most definitely get in the mood for. Yes, I have been known to flip over and growl: "Fuck me in the ass!"

But I bet you already guessed that, didn't you?



Discussion of the Day:

Do you enjoy anal sex or anal play? What was your first time down the dirt road like?