Chapter 6: Conversations and Examinations

After reading the FAQ (three times!) I leaned back on the sofa and exhaled sharply. Part of me couldn’t believe this was real; another part of me was thrilled and hoping against hope that it was genuine. It seemed too good to be true, ridiculously so.

I thought about the entire thing for a couple of minutes, turning the pros and cons over in my mind. I quickly realized I didn’t even want to consider any other option -- I was going to assume that this was legitimate, and see it through until the end. The opportunity was once in a lifetime, and I couldn’t pass it up. Although it could be a trap, a ruse that would end with me in prison, my life ruined, that didn’t seem likely -- this was an awful lot of work just for trapping an anonymous guy like me.

I picked up the phone and dialed the number for Riley and her parents’ cabin. After half a ring, I heard a sweet voice answer. “Hello?”

“Hi Riley,” I said, smiling. “Is your dad around?”

“Yeah. He’s right on the balcony. But before I get him, Mark ... ohgod I have to know ... what’s your answer? Can you tell me?”

I paused only for a second, and gave the only answer I could. “Yes, Riley. The answer is yes.”

“Ohmygod Mark. Oh, thank you. Ohmygod.” She pulled the phone away from her face for a minute, and I could hear her excited voice in the background.

She returned to the phone. “Daddy wants to know if we can come to your room. Is that OK?

“Of course. See you in a few minutes.”

“Bye, Mark.”

As I hung up the phone, I pondered the amazing situation I found myself in -- a beautiful, sexy young girl was thanking me for agreeing to have sex with her.

I pulled off my tie (which I’d neglected to do in my hurry to read the Arrangement website) and straightened up the room a bit before my guests arrived. They knocked on my door, and I invited them inside. Jim and Jennifer sat on the small sofa, and Riley and I sat on the edge of my bed, close to each other but not touching. Her grey dress rode up a bit on her legs as she sat down, and I couldn’t help glancing at her thighs.

Jim looked at his wife, and she began to speak. “Mark, first of all, thank you for saying yes to this Arrangement, and thank you for having an open mind about the whole thing. I know it’s kind of mind blowing.”

I nodded, and Jennifer continued. “I want to tell you why Jim and I, and Riley, decided to take this approach for her.”

“Steve and Caitlin started dating two years ago,” Jennifer said. “He was 21, she was only 16. As you can see, the idea of a bit of an age difference doesn’t really bother us, for either of our kids.”

“Riley and I found out, after they’d been together for about six months, that Caitlin had a really, really bad experience losing her virginity.”

“She was raped,” Riley said softly.

Jennifer frowned. “Riley, that’s not exactly clear. But it was a very thin line -- the young man who took Caitlin’s virginity either raped her or persuaded her in inappropriate ways. It certainly wasn’t 100% consensual on her part, and she didn’t enjoy it at all.”

“Fortunately, Steve has been good for her, he took things slowly with her, and he’s made her realize how wonderful sex can be. Jim and I have always tried to be open with our children about sexuality, having ‘the Talk’ with them at an early age, and answering any questions they might have. We always told them that sex is a wonderful gift, and that we certainly wouldn’t insist that Steve and Riley would have to wait until marriage, or until any specific age. Jim and I both lost our virginities as teenagers -- it would be hypocritical to hold our kids to a different standard.”

“We understand that teenagers have sexual desires, and wanted our kids to have the knowledge they needed to act on those desires in safe ways.”

“That’s wonderful,” I said. “My parents didn’t talk to me about sex at all.”

“That’s very common,” Jennifer said. “But after we learned about Caitlin’s difficult experience -- at 14 years old! -- Jim and I started worry about how Riley would first experience sex. We didn’t want her to have an experience like Caitlin’s. In mentioning this to a friend of ours, she first told us about the Arrangement, which she’d used for both her teenage son and daughter.”

“It sounded like a much more enjoyable sexual experience for young people, and we began researching it. Once we thought it would be a good idea, we introduced Riley to the concept when she turned 15 last year. After some initial hesitation, she realized it was a good idea too.”

Riley spoke up at this point. “It sounded so weird at first, you know -- you and your parents deciding on who takes your virginity? Someone else in the room watching? But then as more and more of my friends had sex for the first time, I realized that most of them had a pretty crappy first experience. I don’t want my first time to be 5 quick minutes in the back of some dumb jock’s SUV, you know?” she finished, blushing.

“I do know,” I said. “A lot of first times are just awful.”

“Was yours?” Riley asked, shyly.

Now it was my turn to blush. “Um, no. My first time was actually pretty amazing. I was a freshman in high school, and a friend of my sister’s -- a junior -- was at our house for a sleepover. They got a little drunk and she snuck into my room after my sister passed out, and, well ... you know!”

Riley and her parents chuckled, and Riley pointed out that she had just finished her freshman year.

“But you see, Mark -- there’s an important point there. Your first partner was someone older, someone more experienced. As you read on the ISPOTA website, that’s a critical part of the Arrangement,” her mom said.

I nodded, and Jennifer continued. “So, Riley got on birth control when she turned 15, and for the past six months, we’ve been looking around for a suitable Expert. We had a couple of previous candidates, but for various reasons, we eliminated them before asking.”

“I wasn’t really happy with either,” Riley said.

“We told Riley,” Jim said, “that we would watch for suitable candidates on this cruise. Having a week on the ship would give us time to evaluate a young man like yourself, and the cabins could allow for some privacy when needed. It’s fortunate that you’re traveling alone, and not sharing this cabin with a friend.”

I smiled. “That’s the last thing I thought when I got onboard -- I was pretty miserable to be taking this trip by myself.” Riley patted my hand with her own, and I shivered slightly.

“So,” Jennifer said, “Here’s what happens next. Tonight, you need to fill out the ESQ so the committee can review it.”

“OK,” I said.

Her husband picked up the conversation. “Tomorrow, we can go ashore in San Juan and see a doctor for your medical exam. I’ve already found one that speaks English and can take walk-in patients. Meet me in the lobby at 9AM.”

I nodded.

“After that,” Jim continued, “we wait on the paperwork. The approval from ISPOTA, and clearance from the doctor. The doc will also need to confirm that you’re actively on male birth control.”

“I am,” I agreed.

“If all goes well,” Jennifer said, “we’ll have the approvals the day after tomorrow, in the morning, while the ship is docked in St. Maarten. In the afternoon, we’ll make arrangements for you and Riley to have your ‘private time.’”

Riley and I both blushed, and Jennifer continued. “It’s somewhat convenient that we’re docked in St. Maarten on Thursday. The age of consent in the Netherlands Antilles is 15.”

“Do you think we’ll have any legal problems?” I asked.

Jim shook his head. “No. As Jennifer mentioned, the AOC in St. Maarten is 15, but that’s just an extra failsafe. Really, while we’re in international waters, there isn’t a legal concern.”

Jennifer spoke up and interrupted, “One of the difficulties we’ve had with considering an Arrangement back home is that the age of consent in Florida is 18. So with any potential Expert, if we did this back home, we’d be asking him to do something illegal. That’s why we hoped to work this out on the cruise.”

“Right,” Jim continued. “And most importantly, remember that no one will ever know about this except the four of us in this room, plus Caitlin and Steve.”

“They have to know, too?” I asked.

Jennifer nodded. “Yes. Given her background, and her closeness to our family, Caitlin is the best choice to serve as Chaperone. Really, here on the ship, she’s the only choice -- Jim and I are ineligible, and I don’t really think Riley wants her brother in the room during her first sexual experience.”

Riley shook her head “no.”

“Oh. I forgot about that part,” I said, blushing again as I considered the ramifications of the cute redhead watching this adorable blonde and I make love.

We chatted about a few more aspects of the Arrangement, and then Riley’s parents stood to take their leave, both shaking my hand and thanking me. Riley didn’t immediately get up, and she looked at her parents. “Can I have a little time alone with Mark?”

Her parents looked at each other, and Jim spoke up. “Ten minutes, and be back in the room. No more.”

She agreed, and Jim and Jennifer departed. Riley took my hand and led me out on the balcony, where we leaned on the rail and looked at the waves below.

“So, Mark, what do you think? I know this must be so weird for you -- but I’ve been thinking about it for months in general, and specifically about you since I saw you first looking at me at the pool the other day.”

“Honestly, Riley? I am a little freaked out,” I said, “a bit overwhelmed, a bit concerned if I’ll be good enough for you. But more than anything else, I’m excited, I’m honored, and I can’t believe how lucky I am to get to be your first.”

Riley threw her arms around me and hugged me tightly, her slim body pressed up against me. “Mark, you’re so handsome, so sweet, so sexy, I just know my first time is going to be wonderful.” I returned her embrace, luxuriating in the feel of her curves pressed against me, the feel of her silky hair under my chin.

After a moment, we released each other, and stood at the rail in companionable silence for a few more minutes, her head resting on my shoulder. I glanced at my watch, and offered to walk her back to her room, so her parents wouldn’t worry. She agreed, and we walked back to her cabin. As we arrived outside her door, she glanced down the hallway in both directions. Seeing no one, she grabbed my head and pulled me down for a quick kiss. “See you tomorrow,” she said.

Back in my cabin, I filled out the “Expert Selection Questionnaire” on the ISPOTA website. It included questions on background information, my sexual history (including details on my first time), marital status, and health conditions. I answered all questions honestly, including the total number of people I’d had any sexual contact with (12); the number of people with whom I’d had intercourse (7); how many times I’d had intercourse with a virgin (1); and my age at first intercourse -- like Riley, I was 15. That latter point soothed my conscience a little, even though I’d had sex with a 17-year-old, not an adult, my first time. Still, I was ready at 15, so why couldn’t Riley be too?

The questionnaire concluded with a question asking me, in my own words, to state why I’d make a good Expert. Again, I answered it honestly -- that was all I could do.

I have grown very fond of Riley during the short time that I’ve known her. She’s beautiful, smart, funny, and very sexy. She has a wonderful family, and her parents obviously care for her very much and are 100% in support of this Arrangement -- in fact, it was their idea! I consider myself a considerate and generous sexual partner, and have always believed in putting my partner’s pleasure before my own. This is even more important with someone like Riley, who is experiencing sex for the first time. I’ve been with a virgin once before, and understand the need to take things slowly, to ensure that she is ready for intercourse and will feel pleasure from it. I would never do anything to hurt Riley, and if she’s uncomfortable with any part of our encounter, I will stop immediately. I understand being asked to participate in this Arrangement is a very important honor, and that Riley (and her parents) trust me a great deal. I won’t do anything to violate that trust.

After that, I clicked Submit, sending the ESQ off to the committee who would decide whether or not I could Riley and I could be together. Obviously, they had no legal control over us. But just as obviously, I knew that if the committee denied me, Riley’s parents would not allow me to take her virginity. They were 100% committed to this strange and wonderful process.

Now, so was I.

I didn’t get a whole lot of sleep that night, as my mind raced through the possibilities. I’d only known about the Arrangement -- and thus the possibility of intimacy with Riley -- for a few hours. But now, I wanted it as much as I’d ever wanted anything in my life, and I’d be devastated if they denied me for some reason. I knew Riley would be as well.

I had another quick room service breakfast the next morning, and showered and dressed in casual clothes. At 9:00, I headed down to the lobby and found both Jim and Jennifer waiting for me, dressed similarly to how I was.

“Good morning, Mark,” Jim said. “Sleep well?”

“Not particularly,” I admitted. “A lot on my mind.”

“Second thoughts?” Jennifer asked, somewhat anxiously.

“None at all,” I said, shaking my head. “Just the opposite -- really, really hoping that I get approved as Riley’s Expert.”

Jim nodded. “Great. Well, let’s head off the ship. I’ve made you an appointment with a local doctor. Jennifer and I will take care of the financial arrangements, and then we’ll leave you at the doctor’s office, and see you back on the ship this afternoon.”

We walked off the Marvel and into the bright sunshine of San Juan. Jim quickly got us into a taxi, telling the driver (in Spanish) where we needed to go. After a short drive, we pulled up in front of a glassy 12-story medical building, no different from those I’d been to in the mainland United States.

We rode the elevator up to the 8th floor, and Jennifer sat with me in the waiting room while Jim took care of the paperwork and payments. “Are you nervous?” she asked me quietly.

“About the exam? No, not really.”

“No, about the whole process,” she asked.

I looked at her, Jennifer’s face completely earnest, searching my own as she looked back at me. Her hair was darker than Riley’s but she had many of the same facial features, just a few decades older.

“I am,” I admitted. “I told Riley last night, this is a huge thing for her, and I want to be sure I’m worthy. She only gets one ‘first time.’”

Jennifer nodded. “That’s very noble of you. Mark, I’ve been married to Jim for almost thirty years. But before I married him -- and also while we were split up for a couple of years -- I’ve had many other sexual partners.”

I blushed -- this woman didn’t hesitate to speak frankly on topics that many people avoided!

“One thing I’ve always realized, is that someone’s personality generally carries over into the bedroom. I learned early on that conceited assholes tend to make awful, awful lovers; while nice, friendly, sensitive guys have given me my greatest experiences.”

She continued. “I know we haven’t known you very long, but everything I know tells me that you fall into that latter category, and that’s why Jim and I are trusting you with our most precious gift -- our daughter.”

I nodded, overcome with emotion, and didn’t even try to speak.

Jim came over to us a few minutes later, and the two of them headed off. I waited another 20 minutes before an attractive Hispanic nurse took me back to the exam room. She did the usual stuff -- pulse, blood pressure, temperature, weight, etc. -- making notations on a chart. She also took a small blood sample from the inside of my left elbow.

Finishing up, she glanced at her paperwork, then pulled a small sample cup from one of the cabinets and handed it to me.

Casting her eyes downward, she handed it to me, and said, “You must provide -- sample. Please come with me.”

She led me down the hall, past a few other exam rooms, to a door marked “private” at the end of the hallway. The nurse gestured for me to enter, and as I did so, she closed the door behind me, saying “please lock.”

I locked it and flipped on the light. Expecting to see a bathroom, I was surprised instead to see a room featuring a small recliner in the center, facing towards a TV. The remotes for the TV and DVD player were on a small table next to the chair, adjacent to a stack of magazines featuring scantily-clad women on their covers.