You need your mind and muscles to be as relaxed as possible to keep your hole from clenching. Try a hot bath, a massage, or some foreplay to help you get your stretch on. Be generous with the lube
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. Once you pass the widest part of the dildo, your body should be more relaxed, which allows you to explore the sensations in your own time. Explore filling and stretching sensations. Once your dildo’s inside, the sky’s the limit!
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One great way to practice and stretch your hole is using Anal Stretching Toys and dildos, Anal plug-ins and Inflatable Dildos. The best of it all is you will enjoy it and experience great pleasure! But how to do it safely so that your hole develops quickly?
How To Stretch Your Asshole In A Nutshell. To stretch your anus, empty your bowels and give yourself an anal douche or enema. Relax and warm up. Lube up and slowly insert anal stretchers until you meet resistance. Let it rest or gently wiggle it around. Once you are happy with that level of stretch, push further up or get a bigger toy.
DIY Anal Stretching Dildo Kits. If you're into the idea of multiple toys to assist you along your stretching journey, you'll find that your options, well, open up. As with any anal toy, you'll want your toy to have a great, big flared base.
“Dildos with too much length or girth, when inserted without the right amount of lubrication, can cause small tears in the anus or vagina,” she explains, adding that trainer kits can be used to slowly (and safely) stretch your holes to help them handle larger dongs.
Well, to make my foreskin opening larger --- I stretched it. I suppose the same principle would apply to your vagina. Find something, like a dildo if they are readily available where you are, that is just the right size then get a slightly larger one and keep going up.
Answer (1 of 4): It’s not only okay, I’d say it should be encouraged! The more practice you have stretching and training and masturbating your ass, the better and easier it is to have anal sex.
If you’re relying on a dilator to stretch vaginal tissue, focus on keeping the pelvic floor relaxed. If you’re relying on a dilator to boost pelvic floor strength, practice performing Kegel exercises. When the vaginal stretching session is complete, clean and store the dilator according to the manufacturer’s directions and repeat daily.