Bear My Dating Life NSFW / Sex True Tales 

Anal FOMO: My 30-Something Anal Crisis


It’s been 17 months. That’s how long Bear and I have been together. Something like that. He keeps count more meticulously than I do. I’m useless with dates. I’m useless with most things that are important, especially as far as numbers are concerned.

17 months doesn’t sound like that long when you think about it. At the same time, it’s the longest time in the world. We moved in together way too early — around the six-month mark — but I wouldn’t say it hindered us at all. It might have helped us, in fact. 17 months isn’t long enough for us to be able to say, “I told you so” to the people who doubted us for moving in too quickly, but it’s certainly a step in the right direction. That’s what I reckon anyway. There were people who gave us “a matter of weeks,” and we’ve definitely outlived all of those bets.

It still amazes me how, even after 17 months, we still manage to find new things out about each other. That’s why 17 months can sometimes feel like a lifetime. By this point, most relationships would have fizzled out, the best sex already laid out on the table, personalities well and truly explored.

That’s not the case with Bear and I. There are still territories new and unexplored. Nervous requests. Lingering fingertips in forbidden places. Last night, for example, we did something brand spanking new. And, no, it wasn’t spanking. But it was amazing. As mentioned in my Tweet, it involved Bear, my butt, and a bottle of baby oil.Anal FOMO_ My 30-Something Anal Crisis 2

We always have a bottle of baby oil next to the bed. He gives me a massage most nights, and I love the way that the baby oil makes my skin feel – super soft, like velvet, touchable. Technically, I’m killing two birds with one proverbial stone: I’m getting a good massage out of it, my knots well and truly worked out; and he’s nicely moisturising the skin on my shoulders, back, and butt, plus he gets to lay his hands on my body for a while, so everyone’s a winner.

That’s how it started last night: with a massage. We’d already had our unromantic late-night banter:

“I need to get in the shower but I’m really lazy. I’ll have one in the morning, but don’t put my cock in your mouth, okay?”

“Oh, it’s cool. Same here. Don’t go tropical. I’ll rub your balls to sleep?”

“Sounds good, I’ll give you head rubs too.”

*  “Tropical” = 

My body was aching and sex wasn’t the first thing on my mind, but he has magical hands that do magical things. I always feel amazing once he’s got to grips with me, working my sore muscles with his expert touch. He rolls his hands over my shoulders, placing light kisses on the back of my neck. Slowly and, at times, painfully, he works his way down my body, ever-so-slightly grazing the side of my breasts with his fingertips under the clever guise of making sure every inch of my back had been attended to.

I don’t actually think he’s aware of the power that his hands hold. There’s a spot he touches that always does something quite magical to me, right at the bottom of my back, at the top of my butt cheek. He needs to pull my underwear down a little to reach it and hit just right, and when he massages the oil in, really grinding his knuckles in, it just does … something? It’s a little painful, but mostly enjoyable, and as well as sending shooting, sharp messages right through my lower back and butt, it also seems to make me wet. Every time. 
I don’t think that’s the outcome he expected to happen from the massage last night, but his probing fingers were doing so much more than just massaging my muscles; they were also massaging my libido quite nicely, sticky pools forming in my underwear, my body switching between flushing red hot and shivering with cool chills. 
I pushed my ass back a little into his hands as he massaged me, a little unspoken message between lovers that signalled: “Sure, go right on ahead. You’ll get no objections here.” Tenderly, he rubbed his hands over my hips. It was almost as though he wasn’t sure he’d understood the message right, so I repeated it, pushing back again, this time releasing a low moan too. 
This time, the message was received, loud and clear.
He used both hands to lift my ass into the air to get the best view. He treats my body like a Christmas present when he undresses me, slowly peeling my underwear down, bit by bit, leisurely revealing that gift inside that makes him purse his lips together and mutter something incomprehensible although probably rather explicit. I’ve started to really enjoy listening to those incomprehensible sounds and looking at that face — the face of a man that knows he’s being allowed to bend the rules a little and is damn fucking excited about it.
My face was pushed into the bed, both arms reached behind me, and I used one hand to play with his balls. The other, I used to attempt to stroke his shaft as best I could in my awkward position. I couldn’t stay like that for long, just long enough for him to drizzle a good helping of baby oil over my ass cheeks and start to massage it in. 
I could feel the liquid gliding across my skin, inching its way closer to the forbidden spot I keep for really special occasions. He’s very well aware of my anal-apprehension, and he’s more than happy to take things at my pace, even avoiding the issue entirely when I’ve made it certain I’m not in the mood for that. But last night, apprehension wasn’t what I felt. I think it was excitement? Or anticipation? Experimental curiosity, perhaps? His fingertips around my ass didn’t make me feel uncomfortable; I found myself pushing back into them – not moving away from them – a body reaction I couldn’t help or overcome, but that’s not how I’d usually react. I think, if we’d have been playing with something more suitable than baby oil, I probably would have considered experimenting with REAL anal play. Maybe. More anal play than usual, anyway. Cock-anal play, not just fingers and tongues.
My mind swung back to something that I happened to see on a porn website, a few weeks back; a new ‘type’ of porn I hadn’t entertained before. I wasn’t sure of the ‘technical term’, but I watched as a cock slid in between the ass cheeks of a woman who seemed to be enjoying it a lot, before exploding all over her ass cheeks, hole, and back. 
All of a sudden, that’s all I wanted: to recreate that scene in that porn video that had made me bite my lip so hard it bled when I played with myself as I watched it. I’ve always been a very big fan of a come-shot, and that’s generally the part that gets me there when I watch porn. The thought of Bear’s come-shot in my ass crack? That’s ALL I wanted. It was all I could think of. 
I reached my ass a little higher in the air, allowing Bear’s cock to fall right against it, also using the opportunity to reach my hand down to my clit. I used my first and third fingers to hold my labia open, and my middle finger to gently slide laps around my clit. I was so eager to come. A little too eager. The awkward position made it tough to hit just the right spot and I kept making myself jump with over-sensitivity, hitting the spot just a little too aggressively.
My left hand had been grasping at Bear’s cock, leading it so that it could nestle nicely between the cheeks of my ass. It was almost like he could read what was going on in my head, grabbing the oil and added more to the mix, making things so slippery that I almost I impaled myself right on to him. Holding him as firmly in place as I could with my left hand, frenziedly finger-fucking myself with my right, he took control, thrusting himself back and forth, rolling up and down in between my cheeks. Each movement passed him over my hole perilously, forcing me to keep still. One wrong move and his cock would be in the exact place I didn’t want it to be … yet. I was treating this as a test; if I could handle the sensation of him sliding up and down over my hole, we’d be one step closer to full, penetrative anal sex.
It wasn’t perfect; it was awkward, bumpy, a bit nerve-wracking for us both. I felt like a fifteen-year-old teenager again, and I didn’t come, but my first REAL anal experience in a long time had certainly been more pleasant than a few of my past experiences had been. 
Bear did come. Loud. Proud. Painfully grabbing fistfuls of the flesh on my ass and hips and juddering against me, hot jets trickling down between my cheeks and mixing with my own wetness. It wasn’t frightening, it didn’t hurt, I wasn’t scared. I was excited. This time, I initiated it, something that I didn’t think I’d ever do. 
All of a sudden, anal sex isn’t this big scary thing that I wish I was a part of — a secret sex club that I want to experience so badly, that I really want to give a chance, but can’t. Maybe I can now? Maybe I can give it that fair shot to see whether or not I enjoy it, once and for all? I feel like this is the weirdest 30-something crisis ever, but it’s a genuine one. The anal one. My anal crisis. There are worse crises to have, I’m sure.
He says that fucking my ass isn’t important, but I really want to let him. It’s become this ‘thing’ that I don’t think he knows about, but I can’t stop thinking about. I don’t want to give him everything yet, but I do want to do that at some point. I just want to take my time. I want us to take our time. I want to play, getting more and more adventurous with each play date, first using one of the many butt plugs that I’ve had my eyes on recently. I remember trying anal toys a few times on my own, and I very much enjoyed using them too, climaxing hard and, at times, physically forcing the toys out of my body with my strong orgasmic contractions. 
I’ve been too nervous about anal play with almost every partner I’ve had, to enjoy it properly. But not Bear. He doesn’t make me nervous because he’s clever. He’s taking his time, letting me set the pace. By telling me he’s just not that bothered, it’s MADE me bothered. It’s on MY radar. I read blog posts all the time, of women that have the best anal experiences, and now I want to enjoy it too. I want to have the best anal experiences. 
It’s my time now.

I’ve got FOMO.

Anal FOMO: My Anal Crisis.


P.S. I did come in the end. Bear fell asleep as I rubbed his balls and, with one leg still draped across his, I unhurriedly circled my clitoris to an overwhelming orgasm. It might be the most silent and still orgasm I’ve ever had. Bear didn’t wake up. I did take great pleasure in telling him the day after, though.

Further anal reading:

“Let’s Try Anal!”

Everything BUTT… (Yes, I’m talking about anal sex)

Related posts

2 Thoughts to “Anal FOMO: My 30-Something Anal Crisis”

  1. Re: technical term

    ‘Frottage’ is usually the word I use. It basically means “sexual gratification by means of non-penetrative rubbing.”

    The “don’t penetrate” glide you describe is delightful when performed on/by other slitty bits as well. 😉

  2. hi! it is my first time to visit your site really great and cool.

Comments are closed.

%d bloggers like this: