Chapters tagged lost bet

by MissAriel

Chapter 41

“Looks like I found something,” he says. “No.” I shake my head. “I’m not ticklish. You’re wasting your time.” But he ignores me and begins lightly moving his fingers in that spot and I start twitching again. Fuck. It tickles! He actually found a spot. No one has ever tried to t...

by MissAriel

Chapter 42

Oh no. Not another one of these, I think. His deals are always terrible. The last time we made a deal, I ended up getting spanked butt naked over his lap. Screw that. “Not interested!” I spit back defiantly. Josh starts brushing his fingers on the underside of my leg more rapid...

by MissAriel

Chapter 43

“Okay, stop, stop, what’s the deal? What do you want?” I ask pleadingly. “First, I want you to say, I’m fucked and I need your help,” he says. Josh is elated. He’s finally broken through. I lost another game that I thought I couldn’t lose.

by MissAriel

Chapter 44

I grit my teeth. I do as he asks. What else am I going to do? Drive home naked? “Josh, I’m fucked, and I need your help.” He looks at me expectantly like he’s waiting for something. Oh my God, seriously? He wants me to say that word again. “Josh, I’m fucked and I need your help,...

by MissAriel

Chapter 45

What. The. Fuck. There was no way I was going to let him do that in a million years. No, I can endure this. I shake my head. “No deal,” I say. I could feel my pussy getting wet at the thought. My body is betraying me, but no, I am absolutely not, under any circumstances, going...

by MissAriel

Chapter 46

“Let’s see if this will loosen you up,” Josh says, holding a toothbrush in his hand. The hell is he going to do with a toothbrush? Brush my teeth? What kind of sicko is this guy? To my surprise, I feel the bristles of the toothbrush gently massage my leg and it's the most inten...

by MissAriel

Chapter 47

Oh my God, this tickling is unbearable. I squirm and trash, but I know it’s fruitless. I’m beginning to resign myself to the fact that I’m going home naked tonight. I burst out laughing again, and this time he snips the front clasp of my beautiful pink bra. That was $50, asshole....

by MissAriel

Chapter 48

“I don’t. I promise, I don’t think I’m better than you,” I plead. I try to defend myself, even though I don’t really believe my own words. To be honest, while I think he’s cute, he's right. I did feel like I was out of his league. Yet here I am, tied up naked and being tickled l...

by MissAriel

Chapter 49

He pulls out the toothbrush again and I wince. No, no, no, anything but that. I look at the clock and it still says 40 minutes are left. It feels like an eternity. He’s been fondling my tits for like ten minutes. I would never let someone do that on the first date, yet I’m lettin...

by MissAriel

Chapter 50

I assumed the whole point of stripping me was so he could touch my body without my clothes getting in the way, but instead, he continued using the toothbrush. Are you fucking kidding me? “No way, you’re not going to keep tickling me? You already won, dude, come on," I beg. “Yea...

by MissAriel

Chapter 51

Looking at the clock in the moments between tickling, I see that there’s still 25 minutes left. It feels like an eternity, but barely any time has passed at all. At this point, I’m so horny and , I’ll do anything to make the tickling stop. I swallow my pride. “Josh, ple...

by MissAriel

Chapter 52

Even after all he’s put me through, even after I’ve given him everything he wants, he’s still going to make me fucking beg him to fuck me like some slut. Well, I guess that makes me a slut. “Josh, I’m begging you, please fuck me with a dildo. Please do it rig...

by MissAriel

Chapter 53

“Well, that earned you a 10-minute break. Time to get back to the tickling,” Josh says cheerfully. “No! That wasn’t the deal! I let you fuck me with a dildo so you’d stop tickling me! You’ve got to be kidding me!” I yell. I can't believe the betrayal. I literally only agreed to...

by MissAriel

Chapter 54

“Josh, please, please, I’ll think of something better,” I beg. The clock still says 14 minutes. It’s only been one minute, but it feels like it's been an hour. How could anyone endure this? Who knew a freaking toothbrush of all things could devolve me into such a pathetic state...

by MissAriel

Chapter 55

I keep throwing out options at random, willing to try anything to get out of this predicament, and in a panic, I say something that I immediately regret. “Fuck me in the ass with a dildo, Josh,” I say in desperation. I gasp. I can’t believe I said that out loud. I’ve never let...

by MissAriel

Chapter 56

Josh isn’t pleased. He immediately starts tickling me again with that damn device. I fold immediately. “20! 20, Josh, I want 20 spankings. Please. I want you to do it right now,” I say. I look to the dresser for the clock, which still says 13 minutes. This is going to f...

by MissAriel

Chapter 57

“Thank you, Josh,” I say in utter defeat. Smack, thank you, smack, thank you. This is truly the worst. Between each spank, he rubs his hand all over my firm butt, and I’m never sure exactly when the next slap is coming. The anticipation of not knowing when it's coming is awful....

by MissAriel

Chapter 58

My thoughts are going at a million miles a second. I burst out the first deviant act I can think of that I think he might go for. “I’ll jerk you off and you can come on my tits,” I say. Humiliating. Utterly humiliating. And yet I'm praying he'll go for it. But he just continues...

by MissAriel

Chapter 59

“So, not to be the bearer of bad news, but you said you’d go for a drive with me,” Josh says with a grin. I curse myself for making that addition. “But you know, I’m a fair person, and you’ve been a good sport. If you can get me off before the timer runs out, you can go home,”...

by MissAriel

Chapter 60

I stare at him in shock. No way. He’s really going to follow up on that? Even if it’s nighttime, anyone could see me if we stop at a traffic light. I don’t particularly want any other strangers seeing me naked tonight. But from his tone, I can tell Josh is serious. Suddenly, I fe...