My first time anal was in HS with my bf. He also took my virginity...........lucky boy..........
It was interesting as he did not ask to do it, I asked him to do it. Of course, he's all like, "SURE!!" HS boys will stick it anywhere wet and warm.
I wanted to see what it was like. I knew enough you could not just ram it in there......LOL. I actually spent a good 20 min getting myself ready. With a gloved hand and lube, I put a finger in, then two, then three. I figured that was how big he was. He arrived, we kissed and when he pulled my panties off, I said, "Let's try anal."
I did not know the best position to be in. So, I lubed him, got on my stomach, opened my legs for him, and asked him to go slow and listen to me.
He got close and I told him I was going to touch myself as he goes in so it distracts me. This perplexed him a bit and he paused. I had never touched myself in front of him before. So, he asked me to turn over so he could watch. I did and he loved it.
That was the first time I realized guys like to watch us take care of ourselves.
So, I cum and turn back over. He guided himself to my ass, but had a bit of time getting his cock to enter me......(does that make me a tight ass bitch??) Finally, his head entered me...........and it hurt. I asked him to stop for a bit, he did, and then went in again. It was better the 2nd time going in. I started to enjoy it and went back to touching myself as he was in my ass.
Let me just say I was not expecting such an intense orgasm. I HAD to make a huge loud moan while gasping for air. We were both shocked and he even asked if I was OK.
He continued and did cum soon after. He came inside me and I was not expecting to need to run to the bathroom so fast. (this might be TMI) I had to tighten down back there, and then move slowly to the bathroom with my butt cheeks firmly clinched. It was a little more unpleasant than I thought it would be.
So, he did ask again a few days later. I said ok as long as I can get myself ready first. Well, he was more than happy to "help". He got the glove and lube and then put one, two, then three fingers in my ass to get me ready.
Over the years, I have learned to enjoy anal a lot. I have done some weird stuff back there. I guess I'm an anal girl, LOL. Even today, part of the foreplay for my husband and I is him putting an anal plug in me. Then, we have normal sex. When I touch myself, I put an anal plug in and then go to town on myself.