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Dilators help with psychological fears by preparing you more for what to expect, giving you total control over your body, and erasing any fear or embarrassment in the eyes of a partner. Physically, they allow the sphincter to accommodate a penis over time and should help bottoming get easier

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First, don't neglect foreplay. Instead of going straight for the ass, try a few other activities you enjoy, like oral sex, to get your body turned on and receptive to a new kind of stimulation. In the world of sexual adventure, modern life has removed those old taboos about arse play. Experimentation helps you realise your full sexual potential. It makes no difference if you are gay or straight, bi or trans, pleasure does not define your sexual orientation. A butt plug is a great way to start exploring and working out what you like and what works for you. They can be used before sex, during sex, after sex or even just whilst out shopping. After all, enjoyment doesn't have to be restricted to the bedroom. Richel, O., De Vries, H. J. C., Dijkgraaf, M. G. W., Van Noesel, C. J. M. & Prins, J. M. Risk Factors for the Presence of Anal Intraepithelial Neoplasia in HIV+ Men Who Have Sex with Men. PLoS ONE 8, e84030 (2013). Schmelzer, M., Schiller, L. R., Meyer, R., Rugari, S. M. & Case, P. Safety and effectiveness of large-volume enema solutions. Appl Nurs Res 17, 265–274 (2004). Noor, S. W. & Rosser, B. R. S. Enema Use Among Men Who Have Sex with Men: A Behavioral Epidemiologic Study with Implications for HIV/STI Prevention. Archives of Sexual Behavior 43, 755–769 (2014).

After play, always wash your butt plugs and your hands with warm water and ample soap. If you have a vagina, avoid transferring bacteria from the butt to the vulva or vagina, since that can cause infection. (This means you and your partner need to wash your hands before rubbing any of your other genitalia.) Schmit says you can toss silicone plugs in a dishwasher, and our favorite three nonporous materials — tempered glass, silicone, and stainless steel — can be boiled to disinfect them, provided that they don't contain motors. Where can I buy a butt plug, and which one is right for me? It’s also helpful to consistently eat a high fiber diet that includes foods such as whole grains, broccoli, and beans — as this regulates bowel movements and decreases the likelihood of soiling during sex. Fiber helps bulk up stool and decreases liquidity, further minimizing the chance of a mess. In general, men should consume 30-40 grams of fiber per day, and women should consume 25-30 grams of fiber per day.

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After foreplay, lubricate the outside of the anus and your partner’s penis. It’s important not to stimulate the bottom’s penis while attempting penetration. During penetration, if the bottom’s penis is stimulated, he is likely to experience the bulbocavernosus reflex, or the involuntary contraction of the anal sphincters. This reflex is more pronounced in uncircumcised men, and will make bottoming more painful and difficult. Next, start with something smaller than a plug: Lube up your finger, or ask your partner if you can borrow theirs. Circle the anus with the finger, glide it gently in and out of the anus, then add another finger. Podnar, S. Clinical elicitation of the penilo-cavernosus reflex in circumcised men. BJU Int. 109, 582–585 (2012).Gently allow penetration to the point of minimal discomfort. It may be more comfortable for the bottom to control penetration by sitting on their partner’s penis. Within a minute, the sphincter will relax and the penis can be slowly inserted fully. If you have a vagina, the butt plug is also a wonderful way to experience double penetration: Slide one in after applying lube and wear it during vaginal sex with a penis or dildo. You can also simultaneously stimulate your clit with fingers or a vibrator. Many people love receiving oral while they have a butt plug in. That said, you don't need a partner to enjoy butt plugs — they make for excellent masturbation companions. In fact, solo sex is a lovely way to explore anal play. The bottom line is that anal pleasure through butt plugs is something anyone can enjoy. What should I know about lube? If for any reason anal sex remains painful or you notice the appearance of lumps, bleeding, or an ongoing itch, see a healthcare professional immediately for a thorough anorectal examination. Find Bottom Friendly Medical Support After anal sex, shower normally with a gentle soap. Clean the outside of the anus very gently — do not attempt to scrub. Do not use enemas, including soap suds or Fleets. Get tested for STIs every three months if you are having anal intercourse with more than one partner, and every six months if you are monogamous. You can easily find a gay-friendly or gay-identifying doctor through Lighthouse to avoid negative discrimination or stigma. What If Bottoming Still Isn’t Blissful?