Anal FOMO: My 30-Something Anal Crisis

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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; I 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 baby oil makes my skin feel so soft. Technically, I’m killin’ 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 too. Oh, and he gets to lay his hands on my body for a while, so everyone’s a winner.

That’s how it started last night. 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 made a weird, old-lady clicking noise as I got into bed, setting the unromantic tone even further, and he offered up his hands for a massage. I didn’t turn him down. I never do. I always feel amazing once he’s gotten his hands on me, working my aching muscles hard with his expert touch. He rolled his hands over my shoulders, placing light kisses on the back of my neck. Slowly and, at times, painfully, he worked 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.

It’s funny because I don’t actually think he’s aware of the power that his hands hold. There’s this spot that always does something to me, right at the bottom of my back, kinda the top of my butt cheek. He needs to pull my underwear down a little to hit it just right, and when he massages the oil in, really grinding his knuckles into my muscles hard, 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 quite wet between the legs.

I don’t even think he meant to do that last night, but his probing fingers were doing so much more than just massaging my muscles. They also appeared to be massaging my libido quite nicely, sticky pools forming in my underwear.

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 like he wasn’t sure he’d understood the message right, so I repeated it, pushing back again, this time releasing a low moan too. Message received, loud and clear.

He used both hands to lift my ass into the air for the best view. He treats it 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.

Bless him, I should probably let him loose a bit more.

My face was pushed into the bed, both arms reached behind me. I used one hand to play with his balls, the other to wank him off as best as 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 massage it in. I could feel it inching its way closer to the forbidden spot that I keep for really special occasions. If you’ve been a reader for a while, you’ll already know of my anal apprehension. If you haven’t, I’ll add a few links to the bottom of this post. But last night, apprehension wasn’t what I felt. Was it excitement? Anticipation? Experimental curiosity? 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. That’s not how I usually react. 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. Cock-anal play, not just fingers and tongues.

My mind swung back to something that I happened to see on Pornhub a few weeks back; a new ‘type’ of porn I hadn’t entertained before. I’m not sure what it’s called. Ass play? Crack fucking? No, not that. That sounds like something I’m definitely not into. I’m a soft drug person, not a hard drug person.

I don’t know the ‘technical term’ (maybe you can help?), but his cock slides in between her ass cheeks until he explodes 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. I’ve always been a very big fan of a cumshot. That’s generally the part that gets me off when I watch porn. The thought of Bear’s cumshot in my ass crack? That’s ALL I wanted.

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 lips open, my middle finger pawing at my clit. I was so eager to cum. A little too eager. The awkward position made it tough to hit just the right spot. I kept making myself jump with over-sensitivity too, hitting my bud just a little too aggressively.

My left hand had been grasping at Bear’s cock, leading it so that it nestled nicely between my cheeks. 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 firmly in place 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 it 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 anal sex.

It wasn’t perfect. It was awkward. It was bumpy. I felt like fifteen-year-old teenager again and I didn’t cum, but my first REAL anal experience in a long time was certainly more pleasant than a few of my past experiences have been. Bear did cum. 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. I initiated it, something that I didn’t think I’d ever do. After my previous hospital and anal sex experiences, I’ve had the hardest time associating my butt with something sexual, a problem that I also encountered trying to write this blog post. What sexy words are there for your asshole? That’s not a rhetorical question. That’s a real question. Please answer it.

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. I don’t want to give it all up yet, but I do want to give it up at some point. I 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. I have my eye on a set of three butt plugs that I’d really love to give a try soon. I remember trying anal toys a few times on my own, and I enjoyed using them too, climaxing real hard and, at times, physically forcing the toys out of my body with my orgasm. 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. 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. I want to enjoy it too. I want to have the best anal experiences. It’s my time now. I know that I enjoy it somewhat because my limited play time has shown me that. I have a partner that I trust now. A partner that pushes my boundaries, but only by a little bit each time. I set those lines. It’s like he knew this would happen all along, and now he’s sitting back and smiling as the plan slowly rolls into action. That’s probably not the case. I doubt he’s that smart/cunning/manipulative. I just feel like I’m missing out on something that might actually be quite nice. Better than nice.

I’ve got FOMO.

Anal FOMO: My Anal Crisis.

Anal FOMO My 30-Something Anal Crisis

P.S. I did cum, 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 could be the most silent and still orgasm I’ve ever had. Bear didn’t wake up. I did take great pleasure in telling him today though.

Further anal reading:

2 thoughts on “Anal FOMO: My 30-Something Anal Crisis

  1. Mrs Fever

    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. 😉


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