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The first time is usually scary, disappointing, and some people many even hate it! But for me, after trying it again and again, using different methods and techniques, I finally figured out how to have pleasurable anal sex nearly every time. Now, anal sex is very satisfying for me! This guide will help you understand how to have. See the vibrator section earlier in the book for a refresher on what goes well with first time anal sex. Tip amateur anal sex tumblr #75: When penetration is performed on men, it is with the intention of stimulating the prostate, which is located in the rectum and up about two inches, similar to the female Gspot. When it is performed on women, the. Use a dildo or vibrator on yourself while he s having anal sex with you. Although some women can orgasm from anal alone, most times, they need other forms of stimulation to climax. Using a dildo or a vibrator on yourself while having anal sex is a great way to ensure you and your man are both having a good time. It equates to the way some girls felt the first time someone performed oral sex on them. They report feeling nervous at the time, wondering if their bodies were normal, and how the person would react. Many women feel similarly about their anuses. Be sure that the person you do this with for the first time is someone that you. We took everything they said, combined it with our own knowledge and came up with the ultimate guide to gay anal sex: How To Bottom Like A Porn Star. It s in the form. I then went on to write my first gay sex book, Men Are Pigs But We Love Bacon (Kensington). Chapter 6: How To Bottom for the First Time. 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. Other forms of anal sex include fingering, the use of sex toys for anal penetration, oral sex performed on the anus (anilingus and pegging.