A Debrief and a Quest

I awoke with a start on Sunday morning. I realized why after I opened my eyes. Emma was there in my room, sitting in my chair next to the bed, looking down at me. She was dressed in similar fashion - sports bra and spandex running shorts, although they were different ones from the day before.

“Morning,” she said to me with a smile.

"Jesus you scared me," I replied.

"How could a little girl like me scare a guy like you?"

"I'm just not used to seeing someone else in my room when I wake up, is all. How did you get in here?"

She just shrugged. I watched her look around the room.

"There are a lot of tissues in that trash can over there," she said to me. I could see the return of the now infamous wicked grin to her face. "Did you have a little fun after Mike and I left last night?"

I didn't want to answer that question. I had been a little embarrassed at just how much I needed release after the events of the previous night.

"I asked a question, Mike. It wasn't rhetorical. I want you to answer me. Should I go inspect the tissues and examine their contents?"

"No," I replied sheepishly. I didn't want her seeing how much I had cum after my voyeuristic session the night before.

"So then answer me," she demanded. "Did you jack off after Mike and I left last night?"

"Yes," I admitted.

"How many times?" she asked.

"I ... ummm ... I'm ... not sure," I lied, stammering my response.

"Bullshit," she said to me. "How many times?"

"Four," I admitted, already feeling the deep red of the blush rushing to my face.

She chuckled heartily.

"So something clearly got you excited last night, didn't it Isaac? I wonder what it could have possibly been. What were you thinking about while you were jacking off those four times?"

I knew better than to try to avoid answering her. That typically only made things worse.

"You ... and ... Mike,” I said quietly.

She smiled.

“So tell me, Isaac, truthfully. If I had asked you if you wanted to watch Mike and me at the beginning of the evening, what would you have said?”

“Probably no,” I answered.

“Because it hurts to even think about, right Isaac?”

“Yes.”

“And yet,” she went on, “it was also incredibly exciting. Exciting enough to make you jack off four times in one night thinking about it.”

I nodded, still at least a little ashamed to admit that.

“And I know that about you, Isaac,” she explained. “Which is why I want you to trust me. You need to learn the things about yourself that will turn you on and the things that won’t, but you’re too afraid of the pain you might feel to find out in your own. The thing is, I need you to find out before before I can ever fully commit to you again. Do you understand that?”

“Yes,” I agreed. I’d already figured that much out on my own.

“So that’s why we’re doing what we’re doing Isaac. It’s what I need you to do before I can trust that we can actually make our relationship work.”

“I get that.”

“Good,” she said, “because we have to talk about something that’s going to be a little difficult.”

“What’s that?”

“Prom,” she replied simply.

Shit!

All these years I’d never really even considered the possibility of asking someone to prom. Because of that it hadn’t even entered into my thoughts that I should ask Emma to prom.

“God,” I said apologetically, “I completely forgot about prom.”

“I know that Isaac. I’ve been waiting for you to ask me for a long time, and you never even mentioned it. At first it was just an annoyance, but it’s become more than that.”

“What do you mean?”

“Someone else asked me?”

“And you said yes?” I asked.

She shook her head.

“Not at first. I put him off, waiting to give you a chance to ask me. But you didn’t. Then when we broke up, and I figured I had no reason to wait any longer, so I accepted the invitation.”

“Who is it?”

“I’m not going to tell you. Unless, of course, you want to complete a quest. I will tell you, however, that it is someone new. He is not in my normal group of friends.”

“What kind of quest?” I asked.

“One you won’t like,” she said very seriously.

That scared me, more than a little. If she was admitting I wouldn’t like it, then it had to be something difficult.

“Well, that’s a little frightening,” I admitted.

She just shrugged again.

“We’ll start this quest by having you answer a few questions. Every right answer will get you closer to what I need you to do. If you get an answer wrong, you’ll just have to wait until after prom to find out who I went with.”

“Or I could just go to prom,” I suggested.

“Except that we are dating now, so you can’t ask anyone else to go with you, unless of course you want to break up with me.”

“But you’re going to prom with someone else,” I argued.

“Who I only said yes to because we were no longer dating at the time. So do you want the questions or not?”

“I want them,” I said. I was already incredibly nervous about this. I could feel the butterflies in the pit of my stomach.

“First question,” she said. “What’s the most logical conclusion of a prom date with a girl like me?”

That was an easy question.

“Sex,” I said, quickly and confidently.

“Correct,” she said with a smile.

“Would the fact that it’s at the end of a prom date make me think it should be more special than my usual weekly get togethers?”

“Yes,” I replied, once again very confident.

“Good answer. On to question three. Would it make it more special if I could have a place to go after prom that was comfortable, private, with no fear of interruption, where I could take all the time I wanted to carry out that logical conclusion to my prom date?”

I was getting a little anxious at this point. She was basically telling me she was going to prom with someone else, was planning to have sex with them, and wanted to make it really special. The answer to the question was still really easy. I was beginning to think she was intentionally giving me easy questions to make sure I fulfilled this particular quest.

“Of course,” I said in answer to question three.

“And what would you think would be such a place?”

Another easy question. We already knew of multiple people who made reservations at a hotel on the night of prom. It was almost a rite of passage for those who could get away with it without their parents going ballistic about it.

“A hotel,” I said.

She smiled.

“Easy questions so far, right Isaac?”

I nodded.

“Then let’s keep going. Here’s question five. Would I be okay with it being a cheap motel, like a Super 8, or would it be much more special if it was a fancy hotel?”

Another softball. She’d had sex in cheap hotels with her Friday night hookups in the past. That wouldn’t be very special at all. She would want something nice.

“You would want it to be a nice hotel,” I said.

“Mmm, you know me so well,” she said with a smile. “We’re getting close, just a couple more questions. Are you ready?”

“Yes,” I said.

“I haven’t told the guy I’m going with that I intend to have sex with him. Would it be fair of me to expect him to pay for a fancy hotel without any idea about whether or not we will be using it?”

Oh god. I had begun to be suspicious about where this was going. I was almost certain I knew it in that moment.

“Not really,” I replied. Maybe a guy would spring for a cheap motel on the chance he could get lucky, but an expensive hotel? Not a chance, unless he was certain of the outcome.

“And do you think I can really afford to pay for a nice hotel myself, in order to make it a special night?”

“No,” I replied, a sinking feeling of dread washing over me.

“But do I know someone who could easily afford a nice hotel, and whose relationship with me is such that they might be willing to do it to help out a close friend?”

I was right. I had figured out where this was going. I was quite sure that all the color that had rushed into my face earlier in our conversation was completely gone in that moment. I wondered if it might look as white as the sheet that was still covering me as I laid in my bed.

“Yes,” I said quietly, knowing what my quest was.

“I think you know your quest now, Isaac. I’ll consider it complete when you send me the reservation details of a hotel, assuming it’s nice enough to be suitable for the occasion.”

She stood.

“I rode my bike today,” she said to me, “so I won’t be needing a ride home. I’ll text you the name if you decide to complete the quest. Otherwise, you’ll just have to ask someone after prom to know who I went with. Let me throw in a little bonus for choosing to complete the quest.”

“What’s that?” I asked.

“I’ll make sure to get some photos and video to upload to your shared drive if you do. Otherwise you’ll be left to use your imagination.”

She turned and without another word, she left me alone in my room once again.

I couldn’t possibly agree to pay for a hotel so that another guy could fuck her after their prom date, could I?

That would have seemed impossible earlier in our relationship, but I figured the real answer to that question could be found in the tent that had recently grown in the sheet of my bed, right in the middle of my hip bones.

Oh, god, I really was going to do it, wasn’t I?

I was.

And I did.

I had to spend a pretty penny on the reservation. She had almost **** me into that by not telling me which hotels would be nice enough for her to accept that the quest was fulfilled. She did let me know that I would have to pick one that met her requirements, however.

While on my way to pick up my parents at the airport that evening. I stopped at the Omni Hotel. It was one of the nicer ones that was relatively close to where we lived without being outrageously expensive. I stopped on the way to the hotel and made a reservation in her name, and paid cash for it. I couldn’t have that show up on the credit card my parents gave me, now could I?

When I got back from the airport with my parents, I forwarded the confirmation email the hotel had sent me about the reservation to Emma, and then I waited. It was less than an hour later that I received a text from her with only one word.

Owen.

Fuck!