Anal Sex: What's the Big Deal?

Explicit content warning

04/06/25 • -1 min

How To Sex

Fred Requests a woman's point of view to help him understand.

Then Maye weighs in with good memories and advice.

By BOSTON FICTION WRITER & MayhemLass Listen to the Podcast at How To Sex.

Fred’s Question

Dear BFW;
I've never tried anal sex before. It never appealed to me. Actually, I never have given it much thought until I perused the anal sex category here at Literotica and found it so popular.
I am a bit embarrassed to admit it, but I have never even had sex doggie style either. Yes, I realize that doggie style sex is an overwhelming favorite for hordes of people but not for me. It is not that I did not try having sex doggie style, it just did not work for me; my cock did not reach far enough for me to feel like I was fucking her. I mean, really fucking her. Okay, it reached but it would not go in far enough for me to feel that feeling of deep and satisfying penetration. It felt weird. I mean, I do not have a small cock. My cock is a little bigger than average at 7". Yeah, she seemed to enjoy it, but I was not receiving the same feeling that I receive when doing it missionary style and being able to really pound her.
"Sorry, Honey, scoot down so that your head doesn't bang the wall."
Moreover, although all the women who I have ever been with were clean, having just showered, shaved, douched, and flossed, whenever I tried having sex with them doggie style, I always received an aroma of excrement, which is a total turn off. I mean, I really do not want to smell shit when I am boning someone, and I am not even having sex with them anally; I am just trying to do it doggie style. Yet, when you start pounding away, pumping your pelvic area against her hips, you are going to get a whiff of poopies. And even if she is the most beautiful chick, that is gross.
"Geez, Beyonce, what the Hell did you eat last night? You smell like a 3-day-old Taco Bell."
I remember growing up and that was one of the worse ranks you could say to someone about their mother.
"Shut up Carl! Your mother takes it up the ass."
Way worse than saying that your mother wears combat boots, taking a cock up the ass was a big insult. That is, until a Greek kid moved into the neighborhood and we were playing; and then we started arguing over something stupid and one kid said to the Greek kid.
"You mother takes it up the ass."
The Greek kid, Nick, I think his name was, shrugged and walked away because, apparently, she did take it up the ass. He probably thought the kid was complimenting his mother instead of insulting her.
I remember that movie back in the late '70's, Midnight Express with Billy Hayes. He played a college student who went through Turkey hoping to score some drugs, Hashish, and deliver them back to the United States, only he was caught. Boy, those Turks fucked everybody up the ass; it did not matter if you were a man or a woman. What did he call Turkey, a country of pigs? Anyway, any time you dropped anything in that country, you were best just to walk away from it and pretend that it was not yours rather than to bend over and pick it up only to find a Turkish cock up your ass.
"Fred, Is that your money clip?"
"Hasad, I don't know who that money clip belongs to but it is not mine."
"It has your name engraved on it, Fred."
"Hey, Hasad, do you think that I am the only person in Turkey named Freddie?"
"Yes."
"Okay Hasad, then, kick it over here and I'll lie on the ground with my ass to the pavement to pick it up."
Anyway, call me ignorant and I am sure that I will piss off a lot of people who are into anal sex but I always thought of anal sex as a gay thing or as a Greek thing and never as a another choice selection to my sexual menu.
"Honey, can I fuck you up the ass tonight?"
"Gee, Sweetie, wouldn't you rather have a blow job?"
"Okay, Honey."
Now that I think of it, that movie with Burt Reynolds, Deliverance, I can hear the banjo music, now, showed those mountain men fucking anything that moved up the ass.
"Look, Darryl, a deer. Shoot it."
"Nah, let's track it and catch it. Then, we'll fuck it up the ass before we kill it and bring the meat home to Maw."
Oh, and that scene in Quentin Tarantino's, Pulp Fiction where that shopkeeper takes the black dude down the cellar and he calls his friend, a cop, and the...

Fred Requests a woman's point of view to help him understand.

Then Maye weighs in with good memories and advice.

By BOSTON FICTION WRITER & MayhemLass Listen to the Podcast at How To Sex.

Fred’s Question

Previous Episode

What Are Sex Toys?

Can a device make it better for us?

By Anonymous. Listen to the Podcast at How To Sex.
A battery-charged vibrator
Sex toys — also called adult toys or “marital aids” — are objects people use to have more pleasure during sex or masturbation. Sometimes sex toys can also have medical uses if you have a sexual dysfunction or medical condition. There are many different types of sex toys, and people use them for lots of different reasons.
It’s totally normal to use sex toys, but it’s also totally normal not to — it’s a personal decision, and everyone’s different. As long as you’re using sex toys safely, there’s nothing harmful about it.
Why do people use sex toys?
All kinds of people may choose to use sex toys, for many different reasons. For some, using sex toys is the easiest (or only) way they can have an orgasm — this is especially common for women. Sometimes people use sex toys to help them masturbate. People also use sex toys during sex with their lovers.
Some people with disabilities or limited mobility use sex toys to make it easier to masturbate, have sex, or do sexual activities or positions that would otherwise be harder or not possible for them.
Sex toys can also help treat the symptoms of certain disorders, like erectile dysfunction, genital arousal disorder, hypoactive sexual disorder, and orgasm disorder. And some people find that sex toys help them deal with the sexual side effects of certain medications, health conditions, or menopause — like a low sex drive or decreased sensation in their genitals.

What are the different types of sex toys?

There are thousands of different sex toys out there. Some of the most common ones include:

Vibrators (aka vibes, personal massagers) — Objects that vibrate (move continuously/buzz) to stimulate your genitals. It’s very common for people to use vibrators to stimulate their clitoris and other parts of their vulva and vagina. But vibrators can also stimulate the penis, scrotum and testicles, nipples, and anus. Vibrators come in all shapes and sizes. Some can go inside a vagina or anus, and others are meant to be used outside the body.
Dildos (Objects that go inside a vagina, anus, or mouth.) Dildos come in many shapes and sizes, but they’re often shaped like a penis. Some look like realistic penises, and others are more abstract. They can also be slightly curved, to help stimulate your g-spot or prostate. Dildos can be made out of lots of different materials, like silicone, rubber, plastic, metal, or, break-resistant glass.
Anal toys Sex toys made specifically to stimulate and/or go inside your anus. Anal toys include plugs (usually called butt plugs), anal beads, prostate massagers, and dildos with a wide base. You need to use lube to use anal toys safely. And it’s very important that any toy you put in your butt has a flared base (meaning it’s wider at the bottom) or some other way to pull the toy out, so it can’t accidentally slip all the way in. If a sex toy goes all the way inside your butt, it could get stuck and you may have to go to the doctor to get it out.
Sleeves (aka masturbation sleeves, penis sleeves, or strokers) — Soft tubes that you put your penis into. Sleeves come in all shapes and sizes, and often have different textures on the inside for more sensation. Some even have vibration or suction. There are also strokers that are specially designed for a larger clitoris or smaller penis, particularly for intersex people or trans men on hormone therapy.
Penis rings

Next Episode

The Ten Best Positions For 'Anal-ysis'

The Ten Best Positions For Anal.

By Daniel Fucking Davis. Listen to the Podcast at How To Sex.

All you faithful readers know I’m a big fan of knocking on a girl’s back door. It feels great. It’s naughty. What’s not to like about it?
Nothing... for the guy.
For the girl, anal can often be traumatic. I’ve posted a bunch of times on how to prepare for anal sex. You can type “anal” in my search bar and get a ton of info. But let me highlight some things:Anal sex requires preparation to keep it from being messy.

Anal sex requires relaxation and trust. If the girl isn’t relaxed... if she tenses up... that’s when it hurts.
Anal sex requires a lot of lube. Lots of lube.
Anal sex requires you to begin small. A finger in the ass. Then two fingers. Then your cock.
Anal sex requires you to start slow. Slide it in and pump with short, slow strokes.
Anal sex requires foreplay. Because again, a woman needs to be really relaxed and into it before her ass will open.

What I haven’t written about in much detail is good positions for anal. I’ve said, “If it hurts, try the woman on top.” But beyond that, nothing much. That changes with this post.
“I want to share with you ten positions that can be great for anal.” They’re great for a variety of reasons: intimacy, pleasure for him, pleasure for her, comfort, etc. I’ll spell out the benefits of each one. They are listed in no particular order. But if you read the articles about preparing for anal that I have written and then learn these ten positions, I guarantee you that you can comfortably (and erotically!) add this very enjoyable aspect to your sex life.
1. “The Reverse Cowgirl Rump Rider”

He lies on his back, legs together. She straddles him, facing away and bounces with his dong-a-long in her bonk-a-donk.
This position is great for her, not only because it lets her control how deep and fast her ass is being fucked, but also because it provides a great angle. He’s going straight in, with a slight upward press. Should be comfortable.
It’s a great position for him because of the view - her bulbous back pillows being split by his love meat.

2. “The Sphincter Spoon”

The key to this spooning technique is that the girl pulls her legs up close to her chest, maybe using her arms behind her knees to hold them. When the legs are pulled up like that, the external spincter muscle (i.e. the asshole) loosens some.
When the guy slides in, he goes as deep as possible. But motion is limited.
This position is all about intimacy. There is a ton of body contact. He can whisper in her ear or kiss her neck. Guys, you also can play with her nipples or even reach between her legs and rub gently.
This is a great starter position for the first anal of the night, precisely because there isn’t much motion. It lets her slowly relax her booty.

3. “The Super Sodomy Side Slide”

In this position, the girl lies face-down, then pulls one leg up some. So her one leg is straight down. With her other leg, she’s pulled her knee up close to even with her waist. This tilts her slightly onto her side. The guy then straddles the one leg that is straight down. He spreads her cheeks, and slides in.
What makes this position great for her is how relaxing it is. He can rub her back while he’s fucking her ass. It also doesn’t allow for very deep penetration.
For him there are two pleasures. First, as he pumps, his scrotum is going to be rubbing against the smooth skin on the back of...