Open to, but Can’t Seem to Do, Anal

Pleasing him is important, but I can’t seem to make it work

Holly Bradshaw
Sep 12, 2019 · 9 min read
Image by andreas160578 from Pixabay

know — anal sex is not everybody’s cup of tea. I’m a coffee drinker myself. I LOVE coffee. Tea is…well, it’s there. It exists. It doesn’t thrill me, but I know my partner would absolutely love to have tea with me. He’d be over the moon for a little tea every now and then. So I’d like to give him some.

My experience with anal sex is…complicated.

We all have an opinion about it, right? Maybe you love it. Maybe you’re a lucky duck who can orgasm from anal penetration.

Maybe you have no experience with it and the idea scares you. Or grosses you out. Or excites you! Maybe a little of all three?

My guy is all about the booty. Not in an unhealthy way — he’s never pressured me or tried to force the issue of anal sex, but I’ve never had to ponder whether he’s a butt man or a boob man.

It’s obvious in the way he loves to fondle my ass during intercourse. The way he loves to pound me from behind. The way he prefers I give him oral sex — on the bed with my ass in his face, my thighs on either side of his torso.

I’m not sure what it is, but nearly every man I’ve ever been with has had an interest in the sexual exploration of my hind-quarters.

Based on what I’ve read from fellow sex bloggers I love, I think it’s some sort of legal requirement to write at least one reflective piece on anal sex.

See? These are some of my favorites.

I’ve tried it before

I had a terrible experience with my ex-husband. We were teenagers when we married, and there were a lot of red flags I didn’t pay attention to, including the way he pressured me into different sexual acts.

Halfway into the second year of our marriage, my ex started demanding I let him fuck me in the ass. The two times he tried, he couldn’t get even an inch deep. That part of my body was like a fortress that could not be penetrated.

Unlike my manipulative and coercive ex, my long-term partner has always been a curious, passionate, and respectful lover. He’s never once made demands or made me feel guilt and shame for not meeting his sexual needs.

And, shocker, I’m much more interested in obliging his fantasies than those of my ex.

I’m a determined gal

A while back, my partner and I planned a night to try anal sex. Again.

We’d tried it before, a couple of times, but it always felt too uncomfortable for me, and we never got very far.

He’s used his fingers on me before, which was uncomfortable but bearable. He’s also explored a very strange (to me) interest in using his tongue.

With analingus, I can only stand a few seconds before I get the heebie-jeebies and pull away from his mouth. He’s left with an even harder erection at that point, because he got to momentarily enter forbidden territory before being booted.

During this particular date night, we came up with a game plan to make our attempts at anal sex a reality. We’d done our research, and we had a few ideas to ease me into it.

We were confident. We were going for it. We were going to do anal, for real this time. Anal sex was coming!

Photo by Matthieu Huang on Unsplash

After a nice dinner out, we enjoyed a visit to our local sex store. I typically order online, but every once in a while we’ll go to the store together and discuss our sexcapades in front of the kindly sales staff. It’s a little thrill.

We purchased a smooth purple silicone dildo, about 1.5 inches in diameter. We would still have a ways to go transitioning to his cock, but I was sure that with a bit of practice, a lot of foreplay, and copious amounts of lube, I could move the several sizes up from dildo to penis.

After we got home, I enjoyed a glass or three of white wine. He undressed before getting into bed, and I removed everything but my black stockings. (I have a huge collection of stockings and garter belts — I’m into lingerie about as much as he’s into asses.)

We started off with some good old making out. Honestly, we don’t do enough of that, so I was very much enjoying it. He kissed my mouth, my neck, and then trailed his lips down to my nipples, sucking on them as he massaged me gently between my legs.

He slipped two fingers inside my vagina and removed them, rubbing my slickness over my clitoris as he continued playing with my breasts.

After a few minutes, I pushed his head down between my legs. For the record, I know he likes this. We’ve communicated about it. And I like physically letting him know that I’m ready for more.

I came about 5 minutes later. Then he went for the lube.

We started with the dildo. I rolled over and got on all fours, and he inserted it slowly into my ass.

It entered me easily enough — a very tight fit, but not too painful. He played around with it for a bit, easing it in and out of me and moving it in a circular motion. Next, he left it inside me as he guided his cock into my vagina.

I felt full, and I eagerly met each of his thrusts as he fucked me.

After a few minutes of that, he needed to slow down. “Or else I’ll come,” he shared. Needless to say, all the ass play was doing it for him. He pulled out, and we agreed to go for the gold.

He eased the purple dildo out of my ass before pouring more lube.

“Relax,” he said.

“Easy for you to say,” I retorted, only half-joking.

“Breathe,” he whispered, nudging the head of his cock against the ring of muscle at my center.

I agreed with his advice — the need for breathing, for relaxing. That made perfect sense to me. I tried to do both.

I managed the breathing, anyway.

He pressed in slowly. I felt the pain right away, but it wasn’t too bad. Then, after pausing for a few seconds, he pressed in some more. My breathing quickened, and I emitted a sound that was obviously not pleasure.

He stopped right away and asked if he should pull out, but I said no. I remained still, doing my very best to get my body to relax, to adjust to his size.

This might be a good time to explain that I’m a pretty determined gal when I want to be. I’m a runner, and I enjoy pushing myself as an athlete. I’m the same way with non-physical goals. When I want to achieve something, I work incredibly hard to make it happen.

Giving my partner anal sex after being with him for years of no pressure and nothing but safe, loving, consensual sexploration was something I was going to do, dammit!

The pain subsided, and this time I took the lead. I pushed back into him, testing my limits. I looked back and asked how far he was in.

Really, I meant: How much more do I have to take?

He held his hand up and indicated the length with his thumb and forefinger. Maybe an inch and a half. More inches left to go than I cared to think about.

I took a deep breath and pushed back more. He pushed forward.

And suddenly, without warning, I felt a wave of unbearable pain tearing through me.

I cried out in agony, a sharp ache throbbing deep within. It was a huge jump from the uncomfortable sensation of stretching muscle only moments before. This felt like being stabbed, beaten, and burned inside — all rolled into one.

I panicked and jerked away from him, sprawling onto the bed and gasping for air. I’d literally had the wind knocked out of me. Like I’d just gotten a hard blow to the stomach.

My poor partner, clueless as to what to do, put a hand on my back and asked if I was okay. I rolled onto my side and took slow, deep breaths, and the pain quickly subsided. The whole thing lasted less than 30 seconds.

I explained what I’d just experienced, and we both voted against pursuing it again that night.

He washed up quickly and came back to bed. With no residual pain on my end (pun intended), we happily continued our lovemaking, with him fucking me from behind.

The vaginal penetration felt as lovely as ever. Despite the snafu, we were both still horny from the night’s buildup.

Just before he climaxed, he pulled out and came on my ass. It took less than a minute for him to get off — evidence of what just a mini anal adventure does for him.

Anal sex education

It’s been a while since we’ve tried, and I’ve been doing some studying up. I read and write all day for work, so one thing I love to do is listen to good, informative podcasts from people with lots of experience.

I found the Shameless Sex podcast a few days ago, and it’s absolutely fantastic. In this episode, Charlie Glickman, PhD, covers anal massage, breathing techniques, hygiene questions, useful toys for anal play, etc.

With the help of this information, I’ve come up with a few theories as to why I’m having so much trouble.

  • I can’t relax those muscles. A negative experience with anal sex can cause your muscles to freeze up in anticipation of pain. Even the stress of the day can affect one’s ability to relax that area of the body. These muscles are part of the autonomic nervous system, which regulates certain organs and functions (like our genitals and sexual response) without us having to make a conscious effort. Basically, the anus’s default setting is tight and tense, and relaxing for penetration is a skill I’ve yet to master.
  • Not enough lube? I’m not too sure about this one. I think we used more than enough, but maybe we need to try silicone-based, which stays on longer.
  • Take a few more steps to size up. We went from a finger, to a 1.5-inch dildo, to a penis with, let’s just say, some impressive girth. Maybe we need to work on those steps in between with more toys.
  • My body isn’t super flexible. I’m not great at yoga. I’ve never been able to do the splits. And I know my skin isn’t very elastic, because I have the stretch marks to prove it. Maybe my back door just isn’t built for a penis. Some people, no matter their gender or sexual orientation, just don’t enjoy being penetrated there.

It’s not just the destination — the trip needs to be stellar

I’m not ready to take anal sex off the menu completely. It’s nice to have the option, you know? Most of the time I’ll choose coffee, wine, or an IPA. But there’s also tea there, for when we want it.

My main motivation is that it’s something my partner would get a ton of pleasure out of, so I’d be willing to make it an occasional special. Maybe like a seasonal thing. Anal sex could be the pumpkin spice latte of our sexual activity.

Either way, I love the fact that my partner makes me feel safe with him, and comfortable enough to explore. Even if we don’t hit a certain sexual goal, we can always try again.

And again…


Conversations about sex from all around the world