You have to get past another muscle group to get into the sigmoid colon, then if it's like about 18-20 inches (whew!) it has to go past another curve to get into the descending colon. This is possible if you go slow and use a LOT of lube, like J-lube for instance.
Answer (1 of 6): Going anonymous this time, cause people I know might be watching. I’m a 26 year-old straight male and I’ve been doing anal for many years now, both to myself and several of my sexual partners, so I’ve got plenty of experience in this area, especially when it comes to deep penetr...
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Lube. Use lots of lube. Cover the dildo in lubricant and put some in your ass too. The type of lube you use will depend on the material of your dildo.
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.
Lube, lube again, and lube some more. Like most dildos, XL dildos and fist dildos are generally designed to provide internal satisfaction. Unlike most dildos, large dildos are almost certainly going to stretch your body on their way in, which makes it imperative that you use lubricant, and plenty of it.
To get your sphincters all nice and loose, make sure you are as relaxed and aroused as possible. Use whatever floats your boat: music, a glass or two of wine, or a heart-to-heart talk. Some foreplay and oral sex should definitely help too. As a rule of thumb, the more at ease you are, the more relaxed your anal muscles will be.
To start, lay down and have your partner lube up one or two gloved fingers. Slowly insert the finger, hold it, then slowly draw the finger back. Repeat. If you combine this with a hand job the feeling of pleasure is doubled. Lube should be reapplied as needed - and be sure to talk about what feels good, what doesn't and when you're ready for more.