My Dating Life NSFW / Sex One Ball True Tales 

The Riding Crop

5-minute read



“Is that your boyfriend over there?” my work colleague asked me, pointing to the door.

“Oh my fucking god, yes it is. Why’s he still dressed like that … ?”

On the first night that One Ball was at mine, he decided that he would pick me up from work still wearing his military uniform.

“I know you’re not done for another fifteen minutes, but take a look in that bag and give it some thought while I go and grab us a couple of coffees,” was all One Ball said as he passed me a carrier bag, turned on his heels and walked away.

I took a peek in the bag. Just one item: a riding crop. A black leather riding crop. I could feel my cheeks flush as I tried to discreetly hide it in the office and away from the prying eyes of the people I worked with, but I knew that they knew there was something naughty in the bag.

As I worked my way through my work closing to-do list, I felt my phone buzz in the back pocket of my jeans. I knew it would probably be a message from One Ball so I ignored it. Then it buzzed again, a couple of minutes later. And then again, a couple of minutes after that. He wasn’t going to stop until I’d read them.

“I’m going to cane your ass tonight as you bend over my knees.”

“I know you’re trying to ignore me. I also know you’re thinking about that riding crop. Shall I wear my uniform still?”

“How wet are you?”

I responded:

“Seriously, stop. The sooner I get this done, the sooner you can get your hands on my ass.”

Thankfully, he stopped. Until I walked out of work and he got me in the car, of course, and then he couldn’t wait to tell me – in detail – of all the things he planned to do with me when we got back to mine. The first thing, of course, was to see how smacky that riding crop was.

“Bend over the table, I wanna hit your ass,” he said to me. And still in my work uniform – jeans and a shirt – I did as he directed. I bent over the table and accepted five hits from the crop. They started off lightly and progressively got harder, and from hit three onwards, I squirmed, imagining how the riding crop would feel directly on my skin and not over my jeans.

Sadly, I didn’t get the chance to feel the riding crop directly on my skin. He had other ideas. Still fun ideas, yes … but not riding crop ideas. In fact, the crop was mostly forgotten about from that point onwards. I was thoroughly disappointed.

“I want you to sit on my face,” he said, and I kindly obliged, waiting for him to settle himself back-flat against the bed before straddling him. I did a little more than just sit on his face; I rode his face. It was incredible. With my arms against the wall, knees either side of his head, grinding my cunt back and forth over his lips and tongue … I came so hard that I gushed all over him – twice. I almost drowned him, but that didn’t stop him from having a cheeky, boyish grin on his face when I finally gave him some room to breathe. I don’t normally ‘let go’ like that, but it was fun. I had fun. And it felt so good. I’ve been blessed with a boy that knows how to use his tongue, and also knows where my clitoris is; I want to make the most of that as much as I can!

I wanted to repay the favour so I moved down his body, kissing my way down his bare chest until I finally got to his jeans and tugged them down. More than anything I wanted to make him cum in my mouth. The fact that I haven’t yet is driving me crazy. I’m the queen of giving head … it’s the thing that every guy tells me I’m good at. So why can’t I make him cum that way? It’s frustrating the hell out of me.

I gave it a shot, though. Using my hands to jerk his shaft as I sucked and lapped around the tip of his dick, I managed to get him close a couple of times, but still, no cigar.

“Let’s try a different position. Can I try something different?” he asked me, hopefully.

And once again, I kindly obliged.

“Position me wherever you want me.”

And he did. He put me in the position I had been in just a little while before – back-flat against the bed, head on the pillows. And then he squatted over me, shoving his dick in my mouth as he did so. Not quite as ready for it as I should’ve been, it made me gag and splutter, but that just seemed to spur him on more. I didn’t mind at all; the more dominant he becomes, the hotter he gets to me. And I really put my all into making sure he got his big finish, groaning and spluttering, opening my throat to let him go deeper and deeper, using my hands to caress his balls and grab his ass as best as I could with his legs restricting my arms.

But still, no cigar. After a while of trying REALLY hard, on both sides, his legs started to shake and buckle and we both knew that he was going to fall on me if we carried on for much longer. So we stopped. And once again, he finished himself off with his hands, spraying all over my chest and stomach, leaving me wondering why the FUCK I couldn’t make him cum.

We chatted for a while as we lay on the bed together afterwards. He told me that he wanted to try anal with me, a conversation that seems to be coming up more and more in recent weeks. I’m trying to put it off for as long as I can, mostly because I think I gave in a little too early with The Guy I Couldn’t Get Rid Of, and then anal became the ONLY dish on the menu for him, wanting it all the time. I enjoy anal as a now-and-then kinda dish, not an everyday kinda dish, you know?

Thankfully, I’ve managed to put it off with One Ball quite successfully for a while. He learned the hard way that the lubricant I have in my toy box [Liquid Silk] doesn’t agree with him. There was a ‘posh wank’ while I was at work that left him with red, itching, peeling skin on his dick … so we probably shouldn’t use that lubricant together. But he’s bought new lubricant since then and other butt-related toys, and now I know I’m just delaying the inevitable. He wants to put his dick in my ass and I’m only going to be able to put him off for so long. What’s the deal with anal anyway? Why does everyone seem to be obsessed with it? And by everyone I mean the boys I’m dating. They’re all OBSESSED with it. They all want to do it.

What’s wrong with my vagina?

Why does my ass always have to take centre stage?

But anyway, anal aside, that’s the story of how I didn’t get to experience the joys of a riding crop in all its glory, almost drowned my boyfriend while he was eating me out, and got one step closer to making my him cum in my mouth.

It’s been quite a journey, really.

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