For comfort in entering anally, it works to be really turned on before anal entry. Deep kissing, squeezing nipples, rubbing the vulva and having vaginal sex for a few minutes first really helps to relax the anal muscles. Using lots of lubricant, the penis can push slowly, and if there is any tightness at all, withdraw and wait until the woman feels ready to do it again. The second time again entering slowly will be more relaxed and ready. If the woman rubs her vulva hard as entry happens it will more likely be pleasurable . If not, withdraw and try again when ready. Certainly it helps to have a caring partner who you can trust to be gentle. Once you are warmed up you can go pretty hard and it’s likely to give you a really great orgasm, more than you get vaginally.
So I withdraw and push in a well lubed but pretty big thick black vibrating polyurethane offset rotating dildo, which once it’s five inches in I switch on and it’s buzzing gently and (invisibly) twirling around offset inside her anus – and STILL it’s her first time and now she’s bloody mad for it. I get the vibrations and the whirling to maximum – she’s almost babbling with pleasure. All on her first anal date!!
The Mishneh Torah, a text considered authoritative by Orthodox Jewish sects, states "since a man's wife is permitted to him, he may act with her in any manner whatsoever. He may have intercourse with her whenever he so desires and kiss any organ of her body he wishes, and he may have intercourse with her naturally or unnaturally [traditionally, unnaturally refers to anal and oral sex], provided that he does not expend semen to no purpose. Nevertheless, it is an attribute of piety that a man should not act in this matter with levity and that he should sanctify himself at the time of intercourse."
A male citizen taking the passive (or receptive) role in anal intercourse (paedicatio in Latin) was condemned in Rome as an act of impudicitia (immodesty or unchastity); free men, however, frequently took the active role with a young male slave, known as a catamite or puer delicatus. The latter was allowed because anal intercourse was considered equivalent to vaginal intercourse in this way; men were said to "take it like a woman" (muliebria pati, "to undergo womanly things") when they were anally penetrated, but when a man performed anal sex on a woman, she was thought of as playing the boy's role. Likewise, women were believed to only be capable of anal sex or other sex acts with women if they possessed an exceptionally large clitoris or a dildo. The passive partner in any of these cases was always considered a woman or a boy because being the one who penetrates was characterized as the only appropriate way for an adult male citizen to engage in sexual activity, and he was therefore considered unmanly if he was the one who was penetrated; slaves could be considered "non-citizen". Although Roman men often availed themselves of their own slaves or others for anal intercourse, Roman comedies and plays presented Greek settings and characters for explicit acts of anal intercourse, and this may be indicative that the Romans thought of anal sex as something specifically "Greek".
Reduce your risk of cutting or scratching your partner by trimming your nails. Long nails might tear the thin, delicate tissue of the anus, which could lead to bleeding. It also increases the risk of spreading bacteria that could cause infections. Be sure to wash your hands well and scrub under your nails after anal sex, too, especially before inserting them into the vagina or mouth.