First time pegging.

Discussion in 'Oral Sex' started by SillyHooker, Jun 14, 2014.

  1. SillyHooker

    SillyHooker Guest

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    My boyfriend, after some time dating, confided in me that he liked anal. It took me a moment to wrap my mind around, but found that in the idea of bending him over actually turned me on quite thoroughly. I bought a feeldoe, and after using it for the first time last night, now have two questions.

    Question 1: Tips for keeping it inside me when he's got such a tight ass and I'm soaking wet?

    Question 2: Tips for making it ultra enjoyable for him? He said he really liked it, and he looked and sounded (through the gag) like he was having a great time, but I want to make sure that I won't hurt him, and that I can fuck him the best that I can.

    And yes I'm into anal as well, but my ass is still very tight. He can only slide two fingers in before it becomes too much for me. We're working on that. (Which is actually how I found this website, was googling how to stretch my ass a bit.)
     
  2. Jah Wobble

    Jah Wobble Guest

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    Answer 1) Get a harness. Even with a Feeldoe, my gf likes using a harness to help keep it in place.

    Answer 2) Stop being such a girl and over thinking everything. If he said he really liked it, then he really liked it. He'll let you know if you're hurting him. If you want to fuck him the best you can, then use your words and ask him what he likes. Does he want to be called your little ass-slut? Does he want his hair pulled? Is he imagining you're a guy? Is he getting off on humiliation or submission? How often does he want to be fucked like this?

    More importantly, is play time over once he gets off or does he help get you off as well?
     
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  3. amandatrans

    amandatrans Member

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    my gf fucks my ass with a strapless one, it does move a bit but is great when its up me, she worries as well but dont, if it hurts im sure he will tell you
     
    Seanjohn likes this.
  4. SillyHooker

    SillyHooker Guest

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    This isn't something that was spur of the moment, and I will answer your questions as I know some of the answers already. I do talk to him about what he likes, but sometimes outsiders can give excellent suggestions that neither one of us might have thought about.


    I'm going to call him that and see if he likes it. He doesn't have enough hair to pull, but I will be choking him next time. He's not into guys. It's the submission, although I wouldn't be surprised if he'd want me to try to humiliate him a little as well. And I don't know yet, but he has implied that he would like it to be a regular thing.

    And more importantly... ;) Yes, we usually start out with a lot of foreplay, he's very good with his mouth, and is an amazing kisser.

    Last time after he had an orgasm via strap on, I gave him a few minutes to gather himself, while gently stroking his back, and arms. And then rode him until I was done.

    Also I will look into a harness.
     
  5. pailee

    pailee Member

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    We are into pegging as well. There are a lot of paths in this type of sex, just like in vanilla sex. You have almost mirror world open. I think everyone find their own kinks. Oral sex, domination, bondage, specific positions, etc. From our experience I can suggest that you need to make yourself the one in charge and demanding. It will probably turn him on even more and if something will be wrong he will tell. You might want a safe word. Sometimes it is exciting to be able to say something like: "It is to big." etc. but it is just a part of play, so you need to know how to signal when something is really wrong.
     
  6. *MAMA*

    *MAMA* Perfectly Imperfect

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    Lmao @ OP's screen name. Im kinda sad I didn't think of that first.
     
  7. Razzberries

    Razzberries Members

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    My wife and I just bought a Joques Spareparts harness to use with the a Realdoe. Works great!
     
  8. Seanjohn

    Seanjohn Members

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    The first few times me and the wife did it she was saying she's nervous she was going to hurt me. I told her" baby, I've been doing this for more than 10 years, you can't hurt me with that" lol. He will moan and flinch some but that means he's enjoying it. Your not hurting him until he says your hurting him. Rough him up a bit. I like when it hurts a little,it makes me even hornier
     
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  9. g65389pon

    g65389pon Members

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    Hardest orgasms ever and she has made me cum more than once. We use a realdoe and some where we got the idea, she took a tight fitting pair of panties and cut a hole in the front for her cock to stick out. It must work pretty well because she doesn't complain and she cums almost every time.
     
  10. Tallguy38

    Tallguy38 Visitor

    Damn that sounds hot and incredible!
     
  11. g65389pon

    g65389pon Members

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    It is you should try it
     
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  12. Tallguy38

    Tallguy38 Visitor

    I’d love to get my wife into that!
     
  13. g65389pon

    g65389pon Members

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    Ask her that’s what I did. If you don’t ask or find a way to bring it up in conversation then you’ll never find out
     
  14. Seanjohn

    Seanjohn Members

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    Tell her a friend of yours started it recently and he likes it and see what her response is. If she's totally grossed out then wait a little while and bring it up some other way. Or just be straight forward and be like " I'm tired of always doing the pushing, I want you to do it some to" lol
     
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  15. Tallguy38

    Tallguy38 Visitor

    We use vibrators on each other, suppose it wouldn’t be that far of a reach
     
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  16. Dr-McPeggin

    Dr-McPeggin Members

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    I hear you 100% there, as my wife is the same way. Her biggest fear is that she’s going to hurt me.
     
  17. theamos

    theamos Members

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    My old bf wanted to try it
    I got a strap on about the same size as him
    He has now bought several bigger ones
    I joke he can take more than me
     
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  18. Seanjohn

    Seanjohn Members

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    My wife has known for a long time I like dildos but for a while we never got into it and she never realized what I was able to take she got a bit jealous when she realized I could take our biggest in the backside
     
    theamos likes this.
  19. Deejay88

    Deejay88 Visitor

    How did you feel when he asked you to do it
     
  20. MacDi

    MacDi Members

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    That's a great idea. We've been thinking about trying a feeldoe but weren't sure if it would stay in place on her end.
     

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