I used to work with this girl, who talked about how her and her boyfriend (who was a manager at another store) would have anal sex all the time. I was intrigued by this, partially because I thought she was crazy, but also assumed that she was fairly vanilla in bed. The two of them had nearly a decade in age between them, and she ALWAYS had some story about a fight. I had the “pleasure” of meeting this guy once, on a triple date, it was awkward, and he spent most of his time making a point not to talk to anyone else. Needless to say, I decided, anal sex or not, I didn’t like the man.
Fast forward almost 2 years and I met him again. It was a chance meeting, a flirty exchange, and a quick goodbye. He ended up getting my number from a mutual friend, and he asked me on our first date.
I wanted to fuck him right away, after all, I had heard the man lived for anal sex, and I was a big fan of anal sex. We waited for about a month before we crossed that line, and when we did it was good sex, but not even some anal play. I came to the conclusion that “Can I put it in your ass?” wasn’t exactly a question you ask the first time you have sex. I also realized that I was making excuses as to why a man hadn’t fucked me in the ass, which brought a little smile to my face.
After a few months of dating, and no anal sex, I casually brought up the story that his ex used to tell me, about their anal adventures. At first he just looked at me, and then he said “Oh wait, you’re serious, I’ve never been into anal, in fact, I’ve only had anal sex once and it wasn’t with her.”
I found myself being both very bummed out, and then mad. Part of my attraction to him was the idea that he was into anal, now all he had was his personality, the okay sex, and the fact that he was physically cute. Sadly I have to say my desire for him slowly faded over the next few months, until one day it just wasn’t there. I still think the man is very nice, but I have no desire to touch him ever again.
Is it bad to “unlike” someone when you find out they don’t like something you do? Or is it bad to base your desire on someone based on what you’ve heard?
While I was at work one day recently a chat popped up on my screen: “Pick: long/skinny, short/fat, medium/ribbed.” I was stuck staring at my screen, feeling my whole body getting warmer, the real question, was I more flushed with arousal or with embarrassment?
I made my decision but was given no more details, no matter how much I pleaded, begged, or threatened (I said I was going to withhold blow jobs). He wouldn’t even give me a hint of which hole was going to benefit from this rash decision. I began thinking about the possibilities, I had hoped it was something for my ass, my lover knew I had been working on stretching it out to make room for his huge cock.
About a week later I felt a buzz on my phone, an email, from him, it’s subject “Look What I Found in the Mail.” I felt a jolt of pure pleasure run down my back, arching it a little, which was out of my control and oh so good. I looked around, making sure I would have a private moment to enjoy the picture that was sure to be in the email, thankful suddenly for technology and instant gratification. When the picture finally loaded the jolt turned into full arousal, it was a cockring dildo, double penetration was all I could think about.
He hung on to the toy for a couple of weeks, waiting for the perfect time to use it. Knowing he had this toy in his possession, but wouldn’t let me play with it only made me more frustrated. He told me I had to be good, I had to stretch out my ass and earn the right to play with the toy.
Last weekend we planned on taking the whole weekend, no plans, other than to fill my ass. I hoped that the work I’d been doing would earn me the right to get the double fill, and wouldn’t you know, it did.
The toy was a great addition to our weekend of fuck. He filled my pussy with his hard cock, kept rock solid by the dildo cock ring, and filled my ass with the nice sized ribbed dildo (by the way, I picked the medium/ribbed toy).
We did have some trouble getting the dildo to stay in my ass then I was on top, but it was easy for me to hold it in there an bounce. When he flipped me around and fucked me from behind the dildo slid in and out with ease. I could feel every inch of him inside me, making every hair on my head stand on end.
This toy was worth the wait, and the work.