[M]y second [f]irst try at anal, and it was sooo much more enjoyable! :) | 2016

A little bit of a backstory: I started dating my best friend a while ago, and it was like one of those love stories in movies. I had a shitty on-again-off-again boyfriend who claimed he loved me, but simultaneously cheated on me all the time for two years. All that time, my now boyfriend was there listening to me rant over and over. Eventually, I realized the error of my ways and got rid of the scumbag guy. My best friend and I started to hang out everyday and one thing led to another. He swept me off my feet and put all my pieces back together.

Now that we've been dating for a while, we both decided we wanted to get a little more frisky in the bedroom. Before, with other boyfriends, I never had any sex toys. I never had toys for my own use, and I didn't even masturbate. I was made to feel dirty or weird if I brought it up or did it. My current guy coaxed me into touching myself, and I loved it. Knowing he wanted me to do it made it so much easier to do. Then we started with the toys. We went together and bought a couple dildos, some lube, and I got some lingerie. He loves playing with me with the toys, and I never knew it was going to be so much fun.

Recently, he wanted to try something else. We had been talking dirty one night, and he confessed how much he wanted my ass. He told me about when he fucks me from behind and has a perfect view of it, and how much he longed to take my ass virginity and fill me with his cum. (The scumbag guy before had tried to take it against my will, but since he was trying to go in dry, he didn't succeed in anything except hurting me. He didn't even get it in. That was the extent of my "first" try, and I didn't even want it.) So we made another trip to our local sex shop and bought some different sized plugs, more lube, and a vibrating probe to help warm me up to it.

Our next time together was phenomenal. We were laying down to a nap after getting up early, and I decided I wasn't tired yet. I usually let him know I want sex by rubbing my ass up against his cock while spooning, and he always gets hard for me right away. The more I do it, the more he writhes, and I can feel him growing behind me. Eventually, he forced me to roll over and he tugged my undies off. He went to town playing with my clit, getting me close to orgasm and stopping repeatedly a couple times before he let me finish. When he finally let me get off, I came so hard I squirted, and I've never done that before. When he felt how much wetter I was after that he pushed me over on my stomach and started fucking me from behind while using some of my natural wetness to play with my asshole a little bit. Then he grabbed the mini probe and put some lube on it. When he started to put it in, I want sure how to feel at first because I was worried about the size. He kept fucking me while gradually sliding it in with me loving it (especially the vibrating function), and next thing I know he told me it's all the way in. I came again, but he was so close he didn't even notice. He stopped to tell me he was going to cum soon, and I asked him where he wanted to do it. He got excited right away and said he thought he didn't have that option. He put on some more lube and I slowly coached him until he was all the way in my ass. He told me he wanted me to move, because he didn't want to hurt me. At first, I was worried I wasn't going to like it, but as soon as we got some movement going, I was in heaven. He started thrusting, and I could feel him get close with every thrust. He started to go a little quicker, I heard him gasp, and then I could feel him pumping me full of his thick, warm cum. Feeling him finish made me get off harder than ever before.

I was soooo satisfied with my first try! Before this, I was one of those girls who always said "NEVER" to anal. Now that I know I enjoy it, I'm much more willing to try it again. So don't knock it until you try it! :)