Answer (1 of 2): There are many things you need to know since you are asking this question. 1. Your dildo needs to be flexible, you simply cannot shove a rigit long dildo up your ass.
Use an enema. Make sure you lay down or get your ass above your belly. This is to clean out all the potential blockage in your lower intestine and rectum. 2.) Use a SOFT dildo. No glass, no plastic, preferably silicone or rubber. Make sure you're not allergic to the material the dildo is made of before you insert it.
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Play with some smaller toys, and get your asshole nice and relaxed. Squirt some lube directly into your ass. A shringe, or turkey baster will help here. Lube around your ass, in your ass as far as you can reach. Lube the whole dildo end to end. Lie on your back with a pillow under your tush. This will keep the lube flowing into you. Begin inserting.
Answer: Same way you get to Carnegie Hall - practice, practice. I use butt plugs rather than dildos, they are better at staying put once they’re in there, and they always have a flared base to keep the toy from slipping in too far.
Once you’re ready, spread out in a comfortable position and slowly begin to insert your dildo. You can try lying on your back with a pillow under your bottom, with your legs raised and spread, or you may prefer to squat down over the dildo so you have complete control of the depth.
Try to insert the toy an inch or so over the course of about 3 or 4 minutes. If met with some resistance — which is totally normal — gently remove it, apply lube again, and try again.
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Tasted my own sperm, can't sleep -.-. Throwaway account because shy :/. Two nights ago I [M19] had sex with a [F23], no penetration we cuddled, rubbed each other. I went down on her and after she was pleased she went down on me. After I came, in the heat of the moment I grabbed her and french kissed her.
You want to be in a comfortable position that allows you to open up completely before you insert the dildo inside you. You can try lying on your back and placing a pillow under your rear to give yourself more height, which also helps you slide the toy deeper inside you.