We Did It Again! – My Second Time Getting Pegged

This is pegging. Pegging is amazing.
This is pegging. Pegging is amazing.

And this time I blew up. She fucked me to orgasm. But let’s start at the beginning because this was a night of great sex, not just me getting pegged.

It started when I walked into the bedroom and there she was getting dressed in some sexy lingerie. I hadn’t seen her wearing lingerie for a while so I knew we were in for a good time.

As we had last time, we had been drinking that night and the easy going feeling was still with us. We’d had quite a few “Let’s do it.” moments then let it go without anything happening for my ass, so this time when she said “I’m going to fuck your ass.” I decided we had to do it this time.

But when she asked me, I had to tell her that I wasn’t ready yet. “Let’s fuck first.”

And it was some good fucking.

Lots of lube. A massager-vibrator in the mix. And orgasms.

Fucking in missionary, she held the massager under us and pressed it against my cock as it slid in and out of her juicy pussy. Somehow, it made my cock somewhat numb and I was so hard and fucking her so hard with no threat of busting.

Moving the massager to her clit, she came. “Can you cum again?”

With the massager back on her clit again and my cock that felt like it was on steroids stroking through her folds, she came again.

The massager-vibrator now on the sideline, I fucked her to one more orgasm. “Oh, fuck. I’m done.”

Orgasms seem to be quite physically exhausting for my wife and sometimes she just seems to keep cumming in one continuous roll but three┬ádistinct orgasms is something we’ve never done before. Anyway, as she said, she was done. Time to switch.

We got up, she strapped up with the Red Rider (review here) and we lay back down.

I lay on my back and she kneeled between my knees. At first, she was having fun being rough and pushing my legs back hard like she was forcibly going to have her way with me. But when it comes down to it, she is very careful not to hurt me.

It took a little while to get the angle right – it’s best when she is standing on her knees rather than sitting so the dildo is angled down at first.

Once we got everything in the right place and in the right way, she was off. Last time, perhaps because she was playing with my cock the whole time, I was hard the whole time. This time, getting the dildo up my ass took a little bit longer and she seemed worried she would hurt me. Anyway, during that time my cock went untouched and was soft and floppy by the time I asked her to start stroking me.

But pretty soon my cock was back and again, with her fucking my ass and stroking my cock it felt really good. Not as overwhelming as the first time but it was still really good.

And this time, I came.

With her stroking my cock and fucking my ass, I came.

Unfortunately, at some point, and I do not remember, I said stop. I’m pretty sure I meant to stop fucking my ass but she stopped everything. After the first shot of cum went rocketing out of me, she stopped stroking. The rest of my orgasm pooled on my belly.

I also remember it felt like I squeezed the dildo out of my ass with the first contraction. And I don’t like it. I already knew that I don’t like cumming with anything up my ass from solo play but she wanted me to cum while she was fucking me last time so this time, when it came so easily, I thought I’d go along for the ride and try it out again. But no, I still don’t like it.

So my ideal pegging session would be me fucking her, her fucking me then ending with me fucking her or her sucking me.

7 thoughts on “We Did It Again! – My Second Time Getting Pegged”

  1. How about this…a FMF threesome where as you fuck one woman, the other is fucking yours ass? I bet you wouldn’t mind cumming with a cock in your ass like that! ­čÖé

    1. Now that is a very enticing picture you paint! I’d definitely love to try that and I know it would feel amazing while it was happening but I still don’t think I’d enjoy the orgasm with the dildo up my ass.
      It’s just something that has never felt right for me. I love playing with my ass and getting pegged when I’m in the mood but only until I’m really close. Then the anal play ends and I like to come without anything in my ass. It’s just what feels best.

    1. Sorry, no, that’s not us. My wife doesn’t like cameras in the bedroom and I’m not sure I’d post anything of me getting pegged… at least not yet. I’m still learning how I feel about it and am not sure I want a permanent record of me getting pegged floating around.

  2. Great site dude, I read the whole thing in one sitting. I would say “we” are somewhere like your first post.
    My wife has mentioned once that she would love the control of shagging like that… But doesn’t know if she would actually want to do it.
    Anyway, it has helped me and I might bring it up in conversation soon

    1. Hi gangel123, thanks for stopping by.
      Yeah, pegging is a strange thing to bring up in a hetero relationship. Especially in the world we live in. Talking about these things on the internet with some relative annonymity is great and let’s us learn some great stuff without “gotta be super straight” peer pressure getting in the way. What wrong with a little anal pleasure! On top of that, if it works, it’s a great new dimension in your relationship.
      But saying that, I think you have to have a mature relationship to try this breaking of social norms.
      Good luck with that conversation. I suggest approaching it light-hearted-almost-jokingly. Kind of keep checking to see if she wants to try, see how serious she is then, jump online and buy one together. That’s when you know it’s gonna happen and she really knows you’re for real.
      Have fun!
      p.s. If you want a suggestion for a first dildo and harness, my wife and I have been using this strap-on set. We bought it because it was cheap and is phthalate free (which means it’s “safe”) but after using it, I really like how it feels. The small curve it has isn’t uncomfortable and may just make it hit the g-spot all that easier.

Leave a Reply

Your email address will not be published. Required fields are marked *