Chapter 25: Chapter 25 – Natalie: You want me to do what?

"You have got to be kidding me," I told Hugh.

"Why are you acting surprised? I told you a while ago that I'm going to spank you."

"The quest clearly referred to swats, not a spanking, and it said nothing about me going over your knees."

He shrugged. "And? Are you going to refuse? If I had put that in the quest, would you have balked?"

The answer to all of those, strangely, was no.

"Okay," I said. "You're right. I'm going to do it. But I'm not going to call you sir, and I'm definitely not going to count out the swats or thank you after each one."

His mouth widened into an "O." Oops.

"You read spanking stories," he said.

It wasn't a question, and, even if it had been one, my face heated so much that it surely turned scarlet, completely confirming his accusation.

Hey, even single girls sometimes had needs, and, while I didn't look at porn or anything, I had found some sites with stories that were ... interesting. And even my super conservative mom had read that 50 Shades series. I would never admit it out loud to him, but, sometimes, I thought about being spanked or being tied up or being spanked while tied up when I ... well, you know.

"I wonder what other kinks you're into," he said. "Maybe I should make it a quest. The title would be, 'Tell Me All Your Kinks.' I like it."

Yeah. No. I could just envision that conversation. Maybe you should buy some handcuffs and rope. Have you ever heard of a thing called a one bar? I've read about girls being confined by one with their hands cuffed behind them and a vibrator attached to the front and...

Yeah. No.

My face must have shown my sheer terror at the prospect because he relented. "How about this - if you're over my knee before I reach the count of five, I won't send that one."

I waddled over to him as fast as my spread legs could carry me and plopped my bare stomach atop his shorts, my slightly bent knees on one side of him and my hands braced against the floor on the other. The bottom of my little titties rested against his legs, and his erection pressed into my stomach. I couldn't help but reflect that he kept finding positions for me to assume that were somehow worse than the one I'd just thought was the most humiliating possible. He truly had a gift.

He rested one hand on my shoulder while the fingers of his other one traced patterns on my lower back. "Oh, I just had an awesome idea."

Somehow, I didn't think I'd find it quite as "awesome" as he did.

"We'll introduce a penalty," he said as his circling fingers got closer and closer to my bare butt. "As long as your panties don't fall down to your knees, I won't issue any other quest than the ones I've already got planned. If the panties do fall, though, you have to choose your worst nightmare. Pick between masturbating for me or telling me your deepest, darkest kinks."

"You said that, if I got over here before the count of five, I wouldn't have to do that. You promised!"

"And you don't. You can choose to masturbate for me instead, and you only have to do a penalty at all if you let your panties fall."

Laying over his lap like I was left me really exposed back there. All he had to do was lean a little to his left, and he'd probably be able to see everything I had. Everything. And his deal meant I had to keep my legs spread wide.

"Pick one," he said.

"I won't fail."

"I still want you to pick one just because I want to know."

I hesitated for a moment and then mumbled my answer.

"What was that?" he asked. "Speak up. I couldn't hear you."

"I said touch myself." I couldn't bear to use the word he did.

"Interesting choice."

God! He was so smug. How had I ever thought of his confidence as sexy?

Of course, the fact that I was literally dripping wet down there kind of made it seem like I still did.

He didn't say anything else, but the repositioning of his hands made me tense. He lifted the one near my shoulders off me entirely and moved his right hand to rest on my leg. Very high on my leg. Very, very high. And he was cupping my leg so that, while his palm was firmly on the back of my thigh, his fingers extended between my legs. If he shifted that hand at all, he'd be touching a very sensitive and interesting place.

Finally.

Slap.

My ponderings on the positioning of his left hand made me lose track of what he was doing with his right, so the first swat startled me. It wasn't hard, and it didn't hurt or anything. The sound, however, seemed quite loud in my small, quiet apartment, and it was just, somehow, so unexpected.

I jerked, raising my butt a little, and, when I came back down, the edge of his finger definitely made contact. And he didn't move it, either.

"Wow. I can literally feel heat radiating from inside there, and it's so ... moist," he said.

He'd never lifted his right hand after the swat, and, as he spoke, he started casually stroking my bare backside. Between that and the sheer humiliation of my position and being spanked and the fact that a boy's finger was literally touching me there, I nearly lost it. I moaned.

He immediately moved his left hand down my thigh and lifted his right one. "Sorry, no. Not yet. I'm working on fulfilling your expectations in order, and it's not time for the fourth, yet."

My mind spun. I'd hit Level 5, so that was my first expectation complete. And he was doing a great job of not self-editing his dares, fulfilling the second. Well, I assumed at least. I hoped. Otherwise, I really didn't want to know what he'd come up with if he considered that this constituted taking it easy of me.

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That left only getting me naked. Okay. Worked for me.

I began to close my legs in order to let me panties fall, but he applied pressure to the inside of my thigh with his left hand.

"Are you sure you want to do that?" he asked. "Remember the consequences..."

Oh. Right. His penalty. Touching myself in front of him.

The thought of the complete, total, utter humiliation of performing such an act with someone watching warred with the need that was building down there. My reticence to disgrace myself in such a manner won, but it was a near thing.

I had to do something, though.

"Hurry," I said. "Please."

God! I was literally begging him.

Hugh hesitated for a moment before seeming to come to a decision, and the swats came fast after that. I didn't count, but there were a lot. I assumed thirty.

The experience was ... interesting. I was definitely, somehow, even more aroused at the end than I had been at the beginning, but I wasn't sure why. Some combination of shame and exposure and his hands touching bare parts of me definitely did it for me. I wasn't sure if I would ever be brave, of stupid, enough to request that he do it again, but I wouldn't exactly fight him, either.

"You can stand now." His voice was husky.

Good. Considering how affected I was by this, it would have been completely demoralizing if he wasn't reacting the same way.

I did, and a blue box soon appeared.

Look, the thought of removing my panties and finally being officially naked in front of him was still scary and embarrassing. I know; it sounded stupid even to me, but, even though no important part of me was covered, I could still think to myself that at least I wasn't totally nude, which provided a weird sort of comfort. I was about to no longer have even that small falsehood to console me.

On the other hand, I was so ready for this. The sooner I fulfilled my third expectation, the sooner we moved to the fourth, and I was prepared to do literally anything to get to that point.

Luckily, the first step of the quest was physically and emotionally the easiest of the day. All I had to do to get the panties to fall was to close my legs, which would hide myself from his view somewhat and was, therefore, something I'd been wanting to do for quite some time now. I quickly did so, and the small, white, lacy garment fell to rest at my feet.

The next part was harder. There was just something symbolic about stepping out of the panties and leaving them behind. It was total and complete surrender. It was saying, "Here I am in all my glory. Not even a vestige of my clothes remains."

Honestly, though, I was ready to surrender that and more. I wanted to. I needed to.

I removed first one foot and then the other and took a small step forward.

Oh no! I'd done it. I'd stripped completely naked for a boy. My hands flew up to cover my face.

The quest wasn't over yet, though. I didn't know if it was Hugh's desire for neatness or if he realized how impactful the seemingly small act that putting my panties away with the dirty clothes was for me that caused him to add that part of the order. Either way, it was a meaningful gesture. Instead of my clothes being right there where I could see them and put them back on whenever I wanted, they were out of sight, another step removed from me both physically and psychologically. This gesture was saying, "Not only did I get naked for you, but I'm ready to stay that way until you otherwise give me permission."

It was so hot.

The panties were on the floor slightly behind me. I started to step backward so that I could kneel and grab them.

"Wait," he said. "Turn around so that you're facing the other way."

I did.

"Take a step backwards toward me."

I did.

A blue box popped up.

One hundred? I didn't get it. I'd already showed him the same view yesterday when I was teasing him in my towel. Why was it so high?

Oh well, maybe the system was starting to become more generous. Great.

Following the exact instructions of the quest, I bent over, sticking my butt practically in Hugh's face. There was a problem, though. I couldn't reach the floor. My arms were too short, and I wasn't quite limber enough.

I stood back up. "I can't do it."

Maybe that was why the reward was so high? Because the quest wasn't possible?

"Yeah," he said. "You absolutely can. Easily. Just think about it for a moment."

Okay, he clearly saw a way for me to accomplish this that I wasn't getting, and I was pretty sure he didn't mean I should spend a couple of months in a yoga class. What was the trick?

It suddenly came to me, and the sheer horror of it dawned on me. The quest clearly stated I had to keep my knees locked. It said nothing about keeping my legs together, and, spreading them apart would lower me enough to reach the floor. But that meant I'd be spreading my legs and bending over with that part of me literally in Hugh's face!

Uh...

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