Hey all, I’ve recently begun my journey to twink/sissydom and had a few questions about insertion. I love the idea of being penetrated, but I’m having trouble putting fantasy into action. I purchased a small prostate massager, but I can’t get it very far in. I use lube, but it’s still tight going in, and I feel like I hit a “wall” that I can’t get past. Pushing up against it just makes my intestines sore. Afterward I just feel a dull pain in my lower back and mental satisfaction.

It hurts and I don’t know what I’m doing, but it feels so right I just can’t stop. Any tips from other, more experienced sissies?

  • GayThrowaway@lemm.eeOP
    5·
    1 year ago

    When you say you feel like you hit a wall, how deep are we talking? When you use lube, are you applying it directly to the toy, inserting it via an applicator or something, or both?

    2"-3" deep, I rub some on my hole and use a pre-lubed condom, I get the sense that’s not enough.

    For me, i hit a ‘wall’ at about 5-6in inside me that requires me to focus, relax, and position myself so my insides align to allow me to take it deeper. Positioning training is good for this- what positions work best are different for everyone.

    What position do you find works best for you? What kind of mental preparation do you do? I smoke a bowl of weed and touch myself for a few minutes to get in the mood but thats about it.

    Thank you for the help, it’s great to find this community so welcoming. I’ll definitely be sticking around!

    • chloespanked@lemmynsfw.comEnglish
      4·
      1 year ago

      You might want to try slowing things down a little; anal stimulation doesn’t provide the same instant gratification of fapping, and people who focus on going slow and enjoying themselves seem to have the best time.

      I finger myself to insert a little lube in myself, I copiously lube my dildo, insert it a bit, and then take it out and apply more lube and re-insert it. For riding, I usually ‘back it up’ on all fours against a wall, squat on it, or take it from behind lying on my side. Suction cups are awesome on dildos.

      Many like porn to mentally prepare, and dressing up. I really like sucking/ deepthroating my dildo. A bath beforehand is really nice too, but it depends on how much time you’ve got

      • GayThrowaway@lemm.eeOP
        3·
        1 year ago

        Thanks, I just get too excited and can’t be bothered to wait it seems. I have a larger suction cup dildo as well that I enjoy deepthroating, but I’m too nervous to try and ride it yet.