"I've tried it before and actually learned to relax and enjoy it, but only with one particular guy. He loves anal sex and was very experienced! The difference with him is that he made his priority to make sure I was relaxed, that I trusted him and was having fun. I tried it again with another person and had to shut that down immediately as that level of trust or care was absent. Although the physical dalliance between Mr. Anal Sex guy and I have stopped for a few years, we're still friends who check up on each other!" says Penelope from Los Angeles.
27.“From a straight guy’s perspective: Like a lot of the previous comments, there’s an element of the taboo involved in it. Anal isn’t quite as accepted in ‘mainstream’ sexual discussions yet, and as such remains a bit out of reach for many curious individuals. Having already done anal on occasion with my girlfriend, the taboo is still there but has been transferred from a ‘mysterious and unknown’ sort of taboo to a ‘so rare as to be mystical’ taboo. On the pleasure side of things, it provides a nice change in sensation from vaginal, oral, and manual stimulation. And while it may not provide as much physical pleasure, its infrequency offsets that since it’s not something you’re typically used to like one of the above three. Also, the intimacy factor can’t be overstated. Because it’s such a rare occurrence for most guys (myself included), it carries a lot of weight when your girlfriend/wife/FWB/etc. gives you the opportunity. It requires more trust and communication than regular sex, and oftentimes your SO is sacrificing some of their comfort (and possibly dignity) to give you pleasure. It’s honestly both thrilling and humbling.”
In addition to nerve endings, pleasure from anal intercourse may be aided by the close proximity between the anus and the prostate for males, and vagina, clitoral legs and anal area for females. This is because of indirect stimulation of the prostate and vagina or clitoral legs.[7][8][9] For a male insertive partner, the tightness of the anus can be a source of pleasure via the tactile pressure on the penis.[10][11] Pleasure from the anus can also be achieved through anal masturbation, fingering,[3] facesitting, anilingus, and other penetrative and non-penetrative acts. Anal stretching or fisting is pleasurable for some, but it poses a more serious threat of damage due to the deliberate stretching of the anal and rectal tissues; its injuries include anal sphincter lacerations and rectal and sigmoid colon (rectosigmoid) perforation, which might result in death.[12] Lubricant and condoms are widely regarded as a necessity while performing anal sex as well as a slow and cautious penetration.[13]

Spreading STIs. Infections and diseases that are shared during sexual intercourse — such as HIV, gonorrhea, chlamydia, and herpes — can be shared through anal sex. In fact, anal sex is the sexual behavior for transmitting and getting HIV for both men and women. People on the receiving end (or “the bottom”) of anal sex are more likely to become infected with HIV than the inserting partner (or “the top”).
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