My Pun-ishment [m/f] [part 2 of 5ish?] | 2016

Click here for part 1

Last we left our heroine, she had made an agreement with a friend to have him paddle her once for every pun he caught her making. But she made so many puns, he felt sorry for her, and offered to alleviate some ahead of time. After zeroing her pun counter one night, she found herself more than a bit turned on by the spankings. Which meant that, more than a few times, they would have wild passionate sex in the back of her car. It is now the beginning of May, 2014. Let's see where she's at, shall we?

There was a dungeon event in a nearby city coming up, and my friends and I were itching to go. Despite the theme being fem dom (female domination), not only was sadistic friend going to come with, but he agreed to let me hit him. At first, the agreement was to just have one scene, but it seemed he had a plan. He offered to let me zero my current pun counter once again, this time on him. In exchange, I would have to go to a later event with him, collared for the whole night. Of course, I agreed.

The count was at eighteen when the femdom event came around. But when we arrived, I was too shy -- I had never been to a dungeon before, and everyone else seemed to know what they were doing. There was a woman flogging a man chained to a Saint Andrew's Cross, two girls doing a more intimate scene on a bench... and here I was, feeling like a total noob. I had another female friend who was also new, and equally nervous, so we constructed a scene where we would both get to hit my new boy toy.

On the drive up, my friend and I had been talking about role play and interrogation scenes, so when we had our guy lying on a table in nothing but his boxers, she brought up the idea of bringing that into it. We were two sexy ladies interrogating him. Seemed simple enough, but the scene got more confusing as it played out. We started spanking his ass and punching his back. "Your kind has sensitive asses" my friend remarked, and this comment of hers turned into calling him an alien. So, we were sexy ladies interrogating an alien.

I picked up a soft cotton flogger and started hitting his back. As we made generally demeaning and threatening comments, there was mention of tentacles. Now, my friends all know about my affinity for squids (hell, it's in my username) so this was no surprise, but this changed the story. Over the course of the scene, it was revealed that we were alien government agents trying to get some sort of information out of my friend. Flogs were swapped out for crops and canes, and the amusing banter between the three of us drew a crowd. My mood shifted rapidly between giggling at the absurdity of our scene and wishing I could just flip him over and fuck him right there. I had played the dominant role before, but for the first time in a long time, I was getting rather turned on doing it.

As the scene ended, we realized we'd need a conclusion. Some alien secret he could tell us. And so, he spilled. "Alright, alright, I'll tell you the password to the airlock." he cried, half laughing in his acting. I repeated after him as he spoke next. "One" "One..." "Two" "Two..." "Three" "Three..." "Four" "Four..." "Five." "Five... wait, one two three four five? That's the kind of password an idiot would use on his luggage!" I had to try not to laugh as I gave my response. We exchanged the highest of fives over the Space Balls reference, and I found myself weirdly turned on by the dorky exchange.

We wandered off to one of the couches for cuddling and snacks. As more and more people arrived, I grew shy. Both my friends had scenes with others as I watched on (my female friend doing a Captain America and Madame Viper interrogation scene). However, I couldn't think of anyone else I wanted to do a scene with, and as the hours ticked past midnight, the dungeon started to empty out. I felt more secure in the smaller crowd, and finally decided I wanted my 18 beatings in before the night ended.

I had him stripped down to boxers, on all fours on a bench, when I realized I didn't know which of my implements to use. I asked if I had a preference between my cane and my crop, and when he had none, I went with the cane -- what I thought was more painful. After spanking and scratching him a bit warm him up, I hit him with my cane a couple times. Then I realized, I only had to hit him with my cane 18 times... any other implements didn't count. So, after pointing out this loophole, I grabbed the crop and went at it. And he started to squirm.

The crop, he told me, actually hurt more than the cane. Which worked out to my advantage, because I could hit him with it as many times as I wanted. And, knowing that, he started to squirm. I tried to calm him with my nails, but that did little. So I laced my fingers into his hair, and every time he squirmed, I would pull. Still, he would not stay still. I tried wrapping one arm around him as I used the other to whap him with my crop, and eventually it felt like I was riding a mechanical bull, trying to keep him still while hitting him. I switched back to the cane for a few hits, but then switched to the crop once more. I wanted to make this last as long as I could.

As we drew closer to the end of the eighteen, I was having a hard time keeping him calm. But then, I had an idea. I put down my implements, and slipped a hand under him, wrapping my fingers around his cock. "Stay... still..." I whispered menacingly into his ear, tightening my hand and sliding it slowly as I did so. "Oh... you're hard..." I smirked, amused. And to think, he had claimed he didn't like being hit as much as he liked doing the hitting. Maybe he was enjoying this more than he'd like to admit. When I pulled away to grab my cane again, I felt his hand on my thigh, sliding up until his fingers were rubbing me through my soaked panties. But I couldn't have any distractions. I shoved him down, so his hard on was pressed up against him, and hit him with my cane again and again, until he was up to seventeen. Then, I switched back to the crop hitting him again and again, knowing how close he was, cruelly not letting him have it. And then, suddenly "Eighteen!" one last thwack with my cane, and we were done.

We didn't get much cuddling in before the dungeon closed and we had to go home, and I didn't see my friend until he came over a couple of days later. We started out cuddling on my bed, making up for the intimacy we didn't have time for days prior, but of course we got distracted when he started massaging my tits. I climbed on top of him and we started making out, pulling off each others clothing and slipping on a condom before I took him inside me. I stayed on top for a bit, but taking advantage of the extra room that a bed provides, he flipped me over such that now, he was on top, and we both came pretty quickly.

Ever the oral fixator, he wanted to go down on me. As he licked and sucked on my clit, he slipped a finger into my pussy, followed closely by a second finger. The continued stimulation was a bit much for my pussy, and I pulsated and tightened around him. He built me up to my climax, fingertips pressing into my G-spot, my moans escalating into screams as he drew out my peak to almost a full minute, causing me to squirt all over him in the process.

As I recovered from the intense orgasms, it struck me that this was my first time having sex in my bed at home. I also realized that since this was both of our days off work, it meant we often enough had a day off work on the same day of the week, which gave us a regular enough time to have sex. So clearly we would have to do this again. And again. And again. And we did. But I'll tell you all more about that in the next installment. :P