Pain during receptive anal sex among gay men (or men who have sex with men) is formally known as anodyspareunia. In one study, 61% of gay or bisexual men said they experienced painful receptive anal sex and that it was the most frequent sexual difficulty they had experienced. By contrast, 24% of gay or bisexual men stated that they always experienced some degree of pain during anal sex, and about 12% of gay men find it too painful to pursue receptive anal sex; it was concluded that the perception of anal sex as painful is as likely to be psychologically or emotionally based as it is to be physically based. Factors predictive of pain during anal sex include inadequate lubrication, feeling tense or anxious, lack of stimulation, as well as lack of social ease with being gay and being closeted. Research has found that psychological factors can in fact be the primary contributors to the experience of pain during anal intercourse and that adequate communication between sexual partners can prevent it, countering the notion that pain is always inevitable during anal sex.
The emotional overture I feel before boarding a roller coaster is about the same as I feel right before embarking on anal sex: excitement, followed by mild hesitation and nervousness. But! The thing about every single roller roaster ride I've been on (so far) is that I've loved them all. No matter how many butterflies are tap-dancing on the bottom of my stomach as the ride lurches up a steep hill, the thrill I feel at the end of the ride is always worth it.