•

New sissy with questions about insertions

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?

5 comments

WallsToTheBalls

•

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?

Anal is largely mental partially physical. You have to train yourself to relax and stretch. Inserting lube inside you is also a big help. Lubing up a toy directly makes it easier, but you’re still fighting unlubed skin until you’ve penetrated yourself far enough to spread it around, and it’s almost never enough just in the toy.

Use an egregious amount of lube. Like, tons of it. Get a large syringe, fill it with lube, and squirt it inside you. You literally cannot use too much.

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.

Anyway that was a mind dump, let me know if you have any other questions, and to to the Lemmy sissy community 🥰

GayThrowaway

•

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

•

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

•

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.

stockings_n_summer

•

You've taken the first step, which is great! Anal can be tricky, but it is very fun.

See if you can use your breath to control your ass muscles. Breathe deeply, from your stomach, not your upper chest; your shoulders shouldn't move when you do this. While you're breathing deeply, see if you can contract your ass muscles when you breathe in, and relax when you breathe out. Once you've got the hang of this try siding a finger or small toy up there while you do it. Let us know how it goes!

And remember, if it doesn't have a base, it can go up without a trace...