My Pun-ishment [m/f] [part 1 of ?] | 2016

So this story starts with a pun. Or rather, with multiple puns. See, among my group of friends, I am somewhat known for always making puns. Some love it, others roll their eyes, but one guy in particular seemed to not like them. Or, he loved to pretend that he didn't like them. In my kinky little group of friends, every time I'd make a bad pun, he'd respond with "that's a paddling".

One day, I began to wonder exactly how many puns I made on a regular basis. And, if he DID paddle me for every pun I made... could I take it? Having never been spanked more than a few times at once, I began to wonder. One day, I let it slip "You know, I'm considering letting you cash in on these". And that is when the punishment began.

The rules began thus: for every pun I made, +1 to the pun counter. If he made a pun, it was -1. On his birthday (June, when March is when this started) he would get to cash in. But come mid-April, the count was high, and I was worried as to how many I could take. After all, I had never taken so many before. He offered to alleviate some of them ahead of time, so the count would be lower on his birthday.

The spankings began at a friend's birthday celebration at a kinky bar. It was Firefly themed -- myself dressed as Zoe, he as one of the Hands of Blue. So based on costume, the set up seemed very fan fiction. I expected a few spankings, and then back to the party.

He had me pull down my pants and bend over a covered pool table (not an unusual scene for this bar) and I obliged. Smack! Well, I thought, that wasn't too bad. Smack! Still, not bad. Smack! Okay, now I'm starting to get how fourty or so of these could be painful, but still... I can do this.

I was determined to prove myself, show that I could take every last spanking that he handed me. I was not going to back down easily. In fact, I found myself slipping into a sort of different state of consciousness... it's hard to explain, but time was moving differently, like every five minutes for them was maybe one minute for me. He upgraded to a flogger, cords stinging my ass in streaks. Then a paddle, one thin and stingy, one heavy and thuddy. And then, finally, the canes. I think the ones he used on me were made of arrows, but I know he had heavier aluminum ones too. It felt like he had only been caning me for a couple of minutes, but I found out later it had been much longer -- quite a lot, for my first time being hit. During the scene, he had remarked quite a bit at how wet my pussy was getting. He'd stroke the outside of my soaked panties with a single finger and give that smile that I would learn to love over the next few weeks... "You really liked that, didn't you?". And he was right. I did.

After a scene as intense as that, we calmed down -- cuddling, water, idle chat. At the end of the night, we retreated to the back of my car, where our cuddle and talk quickly became naked play time. That first time, we didn't even really have sex. But he dug his fingertips into my pussy, hitting spots I never thought existed. I had heard how good he was with his hands (in more ways than one) but here I was, experiencing it firsthand, and it was more than I had expected. Enough that I no longer believed past experiences, where I thought my partner had been hitting my G-spot -- that wasn't it, THIS was it. Or if it wasn't it, it was something far greater.

A couple of weeks later, I had planned on going out for drinks with him and a friend after work. Only, last minute, my friend couldn't make it, so it was just him and I. After sufficient drinks, we went back to my car again to cuddle, which of course turned into fooling around. The parking lot was rather crowded, so we moved the car to the parking garage of an abandoned mall nearby.

Clothes were removed quickly. His hands were all over me, as they often were, massaging my tits as he sucked on my nipples, then cupping my ass, my bottom lip between his teeth. He'd thrust his fingers into my pussy, nibble my neck, ask me over and over what I wanted and I could only think of one thing. "I want to feel your cock inside me."

Finally. He slipped on a condom and I straddled him, taking him in slowly. It had been a while since I'd had sex, so I was kind of trying to savor it. And god damn, did it feel good. If there's one thing I remember, it's the initial feeling of his cock slowly stretching my pussy as he first thrust inside me, trying to take each other in as much as we could all at once, but not too fast either.

We switched positions a couple of times. I was on my back at one point, then straddling him again, but we kept pressed up against each other. I didn't want to let go, and I didn't want him to have to pull out to change positions. It had been a while, and I missed having something for my pussy to grip onto as I came, something where, when I would pulse, would pulse back. Way better than a vapid plastic cylinder.

After involved a lot of precarious clean up. Sweat and cum were everywhere and we ended up using a spare shirt of mine to clean up in lieu of a towel (this is also how I learned to always have a towel in your car). I remember, even at the time, realizing that this was the start of something. And, you know, for (perhaps) the first time in my life, my horrid taste in puns got me laid.

This is the beginning of a really long story... let me know if you guys are interested in hearing more! :)