Pegging

Last night was a great night. We didn't have anything planned, we were just relaxing and enjoying the night. We were both horny as hell and had planned on playing some once the girls went to bed, but I wanted to take it a step further. 

There are a lot of things I have said I would never do or try, or that I just flat out wasn't interested in. One of those things was any kind of anal play. I thought it was gross, I mean, it's your ass! It's for exit only, how could anyone get any kind of pleasure out of it? I didn't understand and was very closed off to it. I was young and conservative, and not that adventurous. I would learn....boy, would I learn.

Fast forward to the first guy I dated after my first husband and I split. Greg was not my typical type. He was a tad overweight, a total geek (because there is a difference between nerds and geeks!), but he paid attention to me. He was my boss at my second job, and that made fucking him that much more exciting. For as reserved as he was, there were things he wanted to try that, at the time, I didn't really want any part of. He really wanted to engage in water sports, and I was NOT into that at all. He approached the subject of anal a couple of times, but I usually brushed him off and quickly changed the subject. One night, after a few beers and a few shots (I was still drinking at this time, among other things), he brought it up again. This time, I figured, what the hell. He told me that if I didn't like it, or it hurt too much, he would never ask me for it again. So we went for it. Anyone that has ever had anal sex knows that you need lube, and lots of it. Things like Anal Eaze help a lot because it has something in it to desensitize you, making the entry not as painful. Well, I don't think Greg took any of this into account, and I sure as hell didn't think about it, so we went at it with nothing. Thankfully, he had a smaller penis, but it still hurt. Telling him it hurt, seeing me tense up, didn't matter. He just wanted to finish. When he was done, I told him that would never be happening again.

Fast forward about another year, and I'm with Dustin. He's asking me if I'm interested in trying it again. I'll be honest, I wasn't completely opposed to trying it with him, but it was going to take a little while for me to be really excited about it. He was okay with that, and never pressured me about it. We would talk seriously, or dirty, or during phone sex, and when I was finally comfortable with the thought, and actually interested in trying it, I told him. I can't honestly tell you how long into our relationship it was before he actually fucked me in the ass, but I will say that it has been somewhat of a staple in our bedroom. 

I started thinking that since I enjoyed him fucking me in the ass, I wondered if he would. When giving him head, I started to play with his ass a little to see what kind of reaction I would get. I got a very positive reaction, so eventually, I would play a little more. I would use my tongue, finger, my little squishy vibrating butt plug once or twice. He seemed to enjoy it all. 

One night, I had him on his stomach so I could kiss his back. I started thrusting my hips into his ass, and heard a very happy moan. At that moment, I wanted to just put on a strap-on and fuck him long and hard. Unfortunately, we don't have a strap-on, so I couldn't do it. I do, however, have a glass toy that is made for anal play. I got it out, and started teasing him with it. Hearing him moan, watching his hips buck, seeing his hand go straight for his hard cock, I knew I was on to something.

Back to last night. I told him that I wanted to fuck him in the ass with that toy. He instantly got hard, and I loved it. We started playing on the couch. I was stroking him, making sure his gorgeous cock was nice and hard, and then I begged him to lick me. I wasn't begging enough, because as he got up, he slapped me, and told me to beg him more. Of course, I obliged, and he began to kiss and lick me all over. God was it good. The way he looked up at me while he was licking my pussy and teasing my ass was so hot! He made me cum a couple of times, and then it was his turn.

I lead him to the bedroom, climbed up on the bed, and immediately started licking his cock. I have never enjoyed giving a man head as much as I do with him. I've had enough practice with him that I'm finally able to deep throat, and I was doing as much of that as I could last night. I wanted him nice and hard and ready for me. I made him roll over on to his side and spread his legs. I was enjoying being in charge and telling him what to do. I immediately grabbed the toy, used the lube, and started to shove it in. I went slow at first because I didn't want to hurt him. The immediate, intense moan coming from him told me I was doing a good job. I can't describe the intense feelings that came over me as I was fucking him in the ass, but I know I want to get a strap-on to be able to do a better job of it. As I had the toy in one hand, I grabbed his cock with the other and began stroking. He turned a little and asked me if I was trying to make him cum, because he was close. I decided to stop, for now, and have him use me. 

That's when he went into Daddy mode, making sure I was enjoying his cock and getting off. But just as I was about to cum, Sir came out and demanded that I hold it in. He flipped me onto my stomach, shoved his cock back in me, and began to fuck me hard, mean, and started spanking me. The pain from the spanking made me want to cum even more, but I was still denied. It wasn't until after he came that I was allowed to cum with him rubbing on my clit. We were both completely spent and satisfied. I asked him if he was okay with everything. He turned to me, smiled, and said that I could fuck him in the ass anytime. 

Anyone that's reading, what are your feelings about pegging? Is it something you're willing to try, or is it a hard limit for you? I'm curious to see what others have to say about this subject.