Chapter 27: Chapter 27 – Hugh: Let’s make a deal!

"So what do we do now? The fourth request?" Natalie wiggled her eyebrows suggestively.

"Soon. Believe me," I said. "I want to do that, too, but we should negotiate first."

"That's an interesting word. I'm not sure that I like the connotations, like this is all transactional."

I shrugged. "It's not meant like that. Some stories I like to read use the term to refer to the process of discussing what each of us wants to happen and what our limits are."

How my life had changed in such a short period of time! I was talking to a naked girl like it was the most natural, common place thing in the world and casually throwing in references to the BDSM erotica that I've read.

"I'll start," I said. "First thing is a rule. If you want me to truly be able to cut loose and enjoy myself, I need to be able to trust that you'll let me know when you're getting uncomfortable, but I understand that's difficult for you to say sometimes, right?"

She nodded.

"So the rule is that, if you start to feel that the situation is a little iffy, just starting to get too far outside your comfort zone, or you just need a moment to process, you say, 'Yellow,' and I'll back off but not totally stop. If you're really feeling like things need to stop for whatever reason, say 'red,' and that's it, whatever we were doing will end."

She just sat there silently, so I gave her a moment to think about it.

"I think that I can do that." She nodded, I thought more to herself than to me. "Yeah. That's easy."

"See? This isn't too bad, is it? Do you have any rules?"

Her mouth opened and shut a few times. "I keep oscillating from wanting to make rules against literally everything and then against literally nothing. I don't know."

"That's okay. This isn't a one time deal." I paused. "The next step is specifics. Touching. From what I gathered earlier, you're okay with me touching and kissing you anywhere I want, right?"

"Yes. More than okay. And you're the one who is insisting that we limit it to hands and mouths. I'm ready for more when you are."

I swallowed hard. She wasn't making this easy for me, but that was okay; I wasn't making it easy for her, either.

"So, just to clarify," I said, "if I wanted to stick a finger up your behind, that's allowed. No holes barred."

I had no desire to do that, but I wanted to make her more aware that she might be agreeing too easily to things she hadn't really thought through.

Her eyes went wide. "Why would you want to do that?"

I shrugged. "Some people are into it."

"Okay, then. I'm ... okay with that."

Really? I was not expecting that at all. This girl was much kinkier than I thought.

"Glad we got that clear," I said, wondering if she was going to be expecting me to do that. "Next is something that I really want to do."

"Okay, shoot."

"I want to take pictures of you."

She immediately shook her head before I could make it to my next sentence.

"Hear me out first," I said. "Please?"

"Yeah, I don't think there's any way I'll be comfortable with it, but I'm willing to listen."

"The pictures are for testing your charisma upgrade. We take shots before and after so that we can compare."

Nat grimaced. "Okay. I get the reason-"

It was my turn to interrupt her. "Don't misunderstand. I would love to take pictures of you. I'd love to have you pose any way that I wanted, to expose every part of you to the camera. I'd love to keep the pictures for my personal use. I'd love to be able to post the pictures on websites and share you with the world. But I don't think you're ready for most of that and you may never be ready and that's okay. It would be nice, but nothing we're talking about here is a deal breaker, okay? I am with you regardless of anything you do or don't do as far as this stuff goes."

"It's like we've turned your honesty switch on. Which is good. I like knowing where you stand. But..."

"Sometimes it might be easier if you didn't?"

"Exactly," she said. "Okay. Pictures. It's just that so many girls in high school had their private photos shared with everybody. I would be terrified of that happening to me."

"I understand. The internet is swimming in pictures of naked women. Hundreds of thousands of different ones. I'm sure that a good portion of them were taken by significant others who promised never to share them. I'm also positive many hundreds of thousands of significant others have taken pictures and never shared them."

"So you're saying that I should trust you."

Again, I shrugged. "I want you to trust me, but I don't expect it at this point to this degree. I mean, if it's really important to you to keep naked pictures of you from circulating, the absolute best way to achieve that is to not ever have any taken. That being said, we could use your phone and upload them to your laptop and digitally scrub them after we finish analyzing them."

She looked away briefly. "Yeah. Okay. I'll do that just as you said. And I'll do the transferring and the deleting off both devices."

"Fair enough. The next thing I really want is for you to be outside naked."

"Hugh, I can't. I'm sorry, but..."

"That's fine. It is perfectly okay for you to refuse."

"But?"

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I sighed. "I just want you to ... listen more?"

"Instead of just shutting you down immediately? But what if there's no way I'd be willing to do it?"

"Again, it really is fine. None of this is as important to me as you, in general, are to me, but I just wish I felt like you were really listening and considering, you know?"

Tears welled in her eyes.

"No," I said. "Please. I didn't mean that to be harsh. I'm sorry."

"You're right. I'm being horrible. You're all like paying attention and being concerned about my feelings and I'm all like, 'Oh. That sounds like it might be a bit uncomfortable. No!'"

"You are not that bad."

"Tell me about something we might do outside," she said. "Give me a scenario."

"We wait until tonight until it's full dark. It's clear weather. There's a nearly full moon. You wear a dress that's easy to put on and take off with nothing underneath. There's an area with hiking trails east of town." One of the tour guides that had escorted my group around campus for freshman weekend this summer had been super enthusiastic about all the outdoor stuff nearby like I gave a care. "If there's a single car in the parking lot, we bail, but it should be empty on a Sunday night. You wear your dress at the start of the hike and, maybe, if you're up to it, you hand it to me for a while."

She rubbed her hand over her face.

"I swear to make it worth your while right there on the trail," I said.

"Can I think about it?" she asked.

"Absolutely."

"I think I have a request."

"Great. Go ahead."

"I want to go directly to number four. Like right now this second you join me on my bed. What do you think?"

When earlier she had made her intentions about today clear, I was terrified. I felt way too inexperienced. I mean, I'd seen plenty of pictures and videos and read stories, but I had no actual idea what to do. I didn't want to mess up or hurt her or just come off looking like an idiot.

Then the experience points I got from her reaching Level 5 pushed me to Level 4. I pulled up my character sheet.

The system was really taking care of me, giving me the exact skill I most needed, Sex Mastery, at the exact right time. I mean, it was only Level 1, but I felt confident that I wouldn't embarrass myself too much, and, just as important, I would be able to make sure Natalie had a good time.

Without that fear holding me back, I wanted to proceed to touching probably as much as she did, but this was a negotiation, and, as my dad was fond of pointing out, the goal of a negotiation was to wrangle as many concessions out of the other side as possible.

"I don't know," I said. "I'd rather get the system business out of the way first. In an hour, maybe less, we'll be finished with the pictures and analyzing."

"Hugh, I'm being serious right now. If I have to wait an hour, I'll scream."

I frowned. "Well, relationships are about give and take, right? What are you willing to give up in return for getting your way?"

"What do you want?"

For the third time in the conversation, I shrugged.

"Okay, how about this? If we proceed directly to the bed, I'll-"

"Sorry to interrupt," I said, "but can we amend that to finishing the two open quests and then proceeding directly to bed?"

"Fine. Whatever. If we do that, I'll let you take ten pictures of me in any pose you want."

"Does that count the ones for the charisma analysis?" I asked.

"No. Above and beyond those."

Nat kept repeating the same behavior. Promising to do something outside her comfort zone, balking at doing the thing she’d promised, and then, when her juices were really flowing, being willing to go way above and beyond anything that she’d promised or even that I’d asked of her.

It was obvious that there was a part of her that desperately desired the feelings associated with the stuff she was doing, but the shy, insecure, self conscious part of her kept holding her back.

My thinking was that I should give her a safe space to experiment however she wanted, and part of that was enticing her to agree to really wild stuff.

Or, at least, that was the justification I told myself. I was more than half sure that I was just really horny and wanted to push things as far as she’d let me.

I frowned like I was weighing her proposal and finding it wanting.

"And you can take the pictures using your phone and keep them as long as you promise, like pinky swear it, that these will be for your personal use only."

I choked back a laugh at the pinky swear, but I think she took my expression as her not offering enough.

She closed her eyes. "And one of the pictures can be of me right outside my door, but you have to make sure that there is no one in sight first."

Yeah. I didn't think the terms were going to get any better that that.

"Natalie McGuire, we have a deal."

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