First Time Anal Giving Or Receiving...Keep it between the Lit Ditches!

Before it happened I hadn't even actually thought about it. I had gone to lunch with some friends and in sharing some love life details one of them admitted to losing her anal cherry to her boyfriend at the time and how she had not really been a fan of the whole ordeal. However, this got the wheels in my head spinning as my current boyfriend was an ass guy and often complimented mine. I went back and forth in my head on how to proceed.

Later on I was at a party with my boyfriend and feeling good with a few drinks and a bit on the horny side. He loved this mood because it usually meant I was going to drop my pants for him. This also meant when he recognized the mood he'd begin asking me here and there when it was time to go home. Being somewhat a playful person when he asked about leaving I asked him why and he said I knew why and he wanted to fuck me. Time to make the call. I said how about we go home and you can have my ass. This totally caught him off guard and broke him for a second or two but then he got excited and asked if I was sure and I said yes.

We were quick to excuse ourselves and get to my house and inside my bedroom. The kissing and foreplay was fun but I could tell he was eager for the main dish. With this I told him it was time and gave him some lube before assuming the position. It felt like forever there on my hands and knees hearing noises behind me but waiting. Soon he was close and I felt his cock travel the length of my butt before settling at the entrance/exit and applying pressure. The initial entry was painful and gave me some regret in the moment of my choice but as things settled and he found his depth the pain subsided and it actually began feeling pretty good.

The moment was not too long as he was excited and worked up. In the end it was probably for the better to have a slow start. He clamped down on my hips and announced he was cumming and I could feel his body shuddering as well as his cock pulsing inside of me. I was surprised how much it turned me on mentally to know what was going on. He finished emptying his balls inside of me and we seperated. He told me he had loved that and wanted to know my thoughts and if this was something that was going to happen again. I told him I was not opposed to it at all but it was going to be slow going.

As expected I was a bit sore there for a day or so following but I did like what I had done and continued to do it and enjoy it more actually both physically and mentally.
 
I let my college boyfriend have my ass the night I broke up with him. I was afraid I wouldn't find another guy I could let me kinky side out for. I thought I was crazy kinky with some of the things I tried and liked with him.
It wasn't bad wasn't as good as vaginally though. I don't think it did too much for the college boy.

Then I started dating the Soccer Coach from the high school. I learned I hadn't really done anything kinky yet. He introduced me to a world of kink and literotica.

When Coach first took my ass, it hurt so much at first.
I remember standing at the bathroom sink trying to relax and finally asking him to stop.
He didn't pull out, he said he was already in. But he did give me time to get used to him and he rubbed my clit to keep me enjoying things.
I was so turned on by what I was allowing him to do. He was so handsome, so powerful and his cock was so perfect.
We didn't try anal very often. but I did learn it was possible for me to cum that way.

Now I love it when Dom fucks my ass. I cum so hard for him. I love when he is taking my ass and he makes me look into the phone he is using to videos me. I love being made to describe what he's doing to me.
 
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My first ass fucking was special; it was in the back alley on a random weekday. It was wonderful
 
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