Anal Sex Advice (Continued)



How to Have Anal Sex by Nymphenomenal

This continues my previous post, “On Anal,” which covered: Considerations | Prep days before | Ready to start when | General arousal and vagina first | Anal tease | Use plenty of lube

Anal entry by fingering:

Anal sex should start slow and small. Slowly insert a lubed pinky finger into her anus. (Make sure his nails are short and smooth so they don’t scratch her inside.) If she can’t tolerate a finger in her ass, she won’t like anal sex. If she’s ready for more, you can work your way up with anal sex toys like butt plugs to gradually stretch open her anus. It may be uncomfortable at first, but it shouldn’t hurt. Stop if it ever starts to hurt! If she starts to bleed rectally, stop and wait until it fully heals before trying anal sex again. Done correctly, she may feel sore but she shouldn’t bleed. However, slight bleeding and spotting is very common, and usually clears up within a week. If it doesn’t heal in a week, or it hurts a lot, go see a doctor right away.

Anal sex positions for penile insertion:

If neither sex partner has tried anal before, the woman should start on top. If she has had anal sex before, you should start with her preferred sex position for anal entry. If he has had anal sex before, but she hasn’t, and she trusts and prefers him to lead, then he can start on top. Being on top gives her more control, though being on the bottom may make it easier for her to relax her anus. Try these four positions to get started on anal sex:

With her on top, try (1) the cowgirl position, so she can ease herself down onto his penis and go at her own pace. When she’s ready, he may flip her over to a better position for him to thrust or do what he wants.

With him on top, try these positions, from least to most uncomfortable for her: (2) lying face-down flat on her stomach (with her butt up), then (3) doggie-style position (with her butt out at him), and then (4) missionary position (with her lying face-up on her back, with her legs tucked up to expose her butt).

Anal technique, pumping, and sensation:

GO SLOW! Even if she’s aroused, relaxed, and lubed up, she may still feel a lot of discomfort, so he should be patient and go slow for her. Her anus may be very slippery and feel very good so tight (especially compared to the vagina), but he should control himself to enter gradually and carefully, especially if it’s her first time ever trying anal sex, as accidentally slipping in can be traumatic for her.

Insertion of the whole tip of his penis may be the most uncomfortable for her, as it stretches open her anal sphincter up to the size of his shaft. Slowly dip his penis in and out of her, starting with shallow thrusts and slowly pumping in his penis a little deeper every time. Whenever his penis slips out of her anus, be careful to reinsert it without touching her vagina, to avoid introducing fecal germs into the vagina, and to avoid spreading fecal matter that could stain your bed sheets. His angle of insertion can also hurt her if the angle is too sharp. She might feel slightly sore from anal stretching at first. As his penis goes deeper into her anal canal toward her rectum, she may feel like she’s pooping, though she isn’t pooping. If she enjoys taking a good dump, she may find this sensation very pleasurable. After a few minutes, her anus should feel adjusted and relaxed, and then she may find it comparable to vaginal sex but in an adjacent bodily cavity. It’s a thin wall between the anal canal and the vaginal canal, so your dick could be indirectly stimulating her g-spot on her front vaginal wall. Some women can even orgasm through anal penetration, especially with simultaneous stimulation (of her clitoris, vagina, mouth, and skin/whole body). Note that men who are anally penetrated can have their prostate stimulated and massaged, which is not only pleasurable but also healthy, as it deters prostate cancer. Best of all, the man penetrating can cum in her anus without the risk of pregnancy (though anal sex still risks transmitting STDs, plus anal warts and anal cancer, plus fecal infection, so condoms are still highly recommended).


After he cums and finishes in her anus, his penis (or his condom sheath) will be covered in fecal germs (invisible) and also possibly some poop (visible). This is harmless as long as: the used condom is thrown away, and his anally inserted penis is immediately washed off with warm water and soap (and NOT reintroduced into a vagina!). Remember to never reinsert anal probes back into a vagina without first cleaning up and at least putting on a new condom!

After sex, she should cup under her genitals on her way to the restroom, in case his cum drips back out of her. Like for vaginal sex, she should immediately pee to avoid UTIs. She should queef any air pumped into her vagina and/or anus, try to drip out his cum, and possibly even poop. Remember to only ever wipe front to back (never back to front), due to fecal germs! Even better if she can also wash the area with warm water and soap or take a shower.

Note that she may feel a bit sore, and even bleed or spot a bit, which are normal, shouldn’t hurt, and should go away within a week. However, if you: have heavy bleeding, are hurting, feel like you have a tear or cut, feel itchy, or have sores, lumps, or unusual discharge, see a doctor as soon as possible, in case you need to clear up an infection. Make sure the issue is gone, she’s not spotting, and everything is back to normal before you resume having anal sex.

Keep in mind that anal sex may be uncomfortable but should never hurt! A woman may not enjoy it her first time or two, as her anus may need to be stretched out (like a virgin’s hymen may need to be torn from the first few times she’s been vaginally penetrated). But, if after a few tries, a woman still finds no pleasure in being rimmed, fingered in the anus, or having anal sex with you, then anal sex probably isn’t her thing. Then you should stop suggesting it, but give her plenty of credit for having given it a shot and trying something new to spice up your sex lives. Here’s hoping you both discover the joys of anal sex! –Nymphenomenal


Author: Lord Beardschlimmer Wilhelm Bartholomew III

Leading the charge against societal decay!