Also , consider that every person has natural variations in anatomy . The actual shape and anatomy of your rectum and anus may not be completely compatible with his erect penis . Like others have said . If it hurts or feels raw ? It ' s cause tissues are likely actually being damaged . You don ' t want to make it worse ! Now . You can work on training your body to relax and grow more accustomed to penetration to see if it something you can do safely at some point . But you will need to work on it . Regularly and carefully so that you don ' t injure yourself . It ' s about finding a toy you can insert comfortably . Using it daily . For increasing lengths of time . Switch to a slightly larger toy . See how long you can keep it in comfortably . Slowly increase the time factor . Your increasing your flexibility and capacity in your butt by increasing the size of the toy . Muscles , and tissues need to be stretched and relaxed to safely accommodate your partner . But going to big to soon can cause physical injury and tearing that may heal on its own . Or could cause scarring or perforation that is a serious medical injury requiring medicalsurgical intervention . Sepsis kills . Rectal perforation or prolapse is a background concern to consider when pursuing this kind of play . Size increase just means your Butt can hold it . Time and duration are important as well . The muscles inside your body also need to be acclimated to it as well . A penis thrusting even gently and slowly is a situation those body parts are NOT used to dealing with . A great deal of the muscle control in that part of the body is automatic . Your body feels a mass and nerves say something is at point a and should be moved along . So when nerves a fire . Muscles b react . Your body has been doing it that way since you were born . Just cause it ' s sexy time . It doesn ' t stop . There ' s is a ton going on down there that you have no direct control over till you train it otherwise . People can tell you to relax . But that only stops voluntary muscle stuff that might trigger a painful tense up . You also need to work on the automatic reactions your body has to the Sensations , and stimuli that Penetration causes . These things cause automatic reactions in the musculature of the rectum not just the sphincter of the anus . While your sphincter may have relaxed enough to allow Penetration , the smooth muscle of your rectum walls on the inside could be spasming or over stretched . Leading to pain and discomfort . You have to give your body time and manageable , safe , injury free experiences over time to figure out how to recognize the difference between the two and when and how to handle sexy time differently then what is left of dinner the night before . Poop happens . Get over itSome people due to their natural variations can adjust to or handle anal easily . Others can work on it . Some probably never will or shouldn ' t even try due to their own natural variations in anatomy . There is no shame or failure in that ! Just some thoughts . I didn ' t even touch on the impact mental stuff has on all this . Excitement , pleasure , hornyness , and such all play into the hormones and endorphins of sex . Those same things trigger all kinds of reactions all over your body . Which brings includes your butt too .