Coconut oil and basically anything in your kitchen, for example, can't be used with condoms. You can lie flat on your stomach, get in doggy-style, or do missionary — and that is the order of what will hurt the least to the most. All of this means that anal penetration stimulates your G-spot from new, highly sensitive angles, making an orgasm much more plausible than you might think. Latex-safe, waterproof, and thick, this silicone-based lube can be found in drugstores across the country, and it's as affordable as it is awesome. We did the same thing, applied that latex glove, lubed up each finger and then slowly penetrated my ass, then wiggled and tapped the fingers.
10 things you should know before you try anal sex for the first time. I’ve received lots of questions asking me how to have anal sex without hurting her. I’ve found that, like I was, many people are nervous and confused about anal sex. Anal sex or anal intercourse is generally the insertion and thrusting of the erect penis into a person's anus, or anus and rectum, for sexual pleasure.