Guys, would it be weird for me to ask him to pick out a sex toy for me?

We have tried anal once before (spontaneously jumping in the deep end not recommended) Anyway since then he’s been saying things like do you want me to stick a finger in or sometimes rubbing this dick on that area “jokingly” I feel like that is something he wants to explore more but I’ll need some warming up to it. Do you think he would want to help me/pick out a butt plug for me to use or would that be something I should do alone? There is something sexy to me about him picking it out.
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Most Helpful Guys

  • I can't speak for him but I would enjoy helping pick it out. My wife and I have a lot of anal sex and anal play and we use a lot of toys, but I usually do the shopping and buying.

    Whatever you choose to do, if you think you want to give anal a serious try I would strongly suggest not just warming up before you do it, but actually taking some time to train your ass for a while first. That means getting some toys and using them to gently stretch your ass while you masturbate by rubbing your clit so you can have some orgasms. That's important because it associates the sensations of anal stimulation with pleasure in your brain. It will make the process more fun and make anal sex more enjoyable later on. My wife tells me the combination of anal and clitoral stimulation gives her the best orgasms now by far, but it took her a little while to get there.

    As far as toys go, the best choice for you at this point would be a butt plug that has a small tip and tapers to roughly the diameter of your boyfriend's penis. It's a bonus of it vibrates.

    • Thanks for the advice! I asked him and we are going together on Friday!

    • Nice, good luck. By the way, I buy most toys online via Amazon.

    • Thank you for MHO.

  • He could but might not be the toy you like, just make sure if you do anal again try and clean out your colon, otherwise if he goes in he's gonna get shit on his dick and your gonna shit stuff out during.

    I'd say practise on yourself, try and get used to something penetrating that area, start with something small and work your way up to something the size of your boyfriend's dick.

    Also use lube, don't go on dry

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What Guys Said

(17)
  • No, that seems fun.
    Easy way to talk about what you like.

  • Not necessarily

  • I think I should share in it! It can be a sexual experience. But, you know him better than we do.

  • Not at all as long as you are sexually involved or at least interested in the relationship moving in that direction.

  • Very weird

  • Depends upon guy's mind. My ex asked me for a sex toy explaining that she needed when alone. I bought one for her.

  • Heck no, I think that would a total turn on, especially If I got to watch you use it. :)

  • I assume we're talking about your boyfriend here. Now why on Earth would that be weird with your own boyfriend? I'm sorry, but if you feel awkward about something like this WITH YOUR BOYFRIEND, then there's something wrong with your relationship.

  • Not weird at all. I have done that for a shy girl: I bought (as a present) for her a small dildo. I was comfortable picking it out, I have had experience with sex shops, and she was too shy / afraid to enter one. She trusted me with my judgement.

    Go for it, ask him for that favour if you trust his judgement.

  • He would be all for it for your showing him that you are willing to get better at anal.

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