The Arrangement - Cover

The Arrangement

Copyright© 2016 by MarkStory

Chapter 12: Freshman Frustrations

Coming of Age Sex Story: Chapter 12: Freshman Frustrations - Mark takes a Caribbean cruise - unexpectedly by himself, after his girlfriend breaks his heart. Onboard the ship, he meets a teenage girl named Riley and her family. The family asks Mark to participate in a very special tradition, one that he's never heard of. The story covers what happens on the cruise, and what happens in subsequent years, as Mark and Riley try to maintain their relationship.

Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa   Ma/ft   Fa/ft   Teenagers   Consensual   Romantic   BiSexual   Heterosexual   Fiction   Group Sex   First   Safe Sex   Oral Sex   Masturbation   Exhibitionism   Slow  

The first year of Riley's college career was a difficult adjustment -- for her, for me, for us.

When it was time for her to move to campus, she and her mom flew into Boston and spent one night at my condo, while Steve and Jim drove a cargo van from Orlando to Amherst.

I'd offered to drive the two of them to Amherst, but Riley asked me not to, and her mom rented a car for the two of them. "It'll be weird enough having to say goodbye to mom and dad and Steve -- if you're there too, I'll be a nervous wreck. Come visit me in a week or two when I get settled in."

I agreed, and we made the most of our one night together, making love in my bed, trying to be as quiet as possible in deference to her mother being in the guest room next door. But, judging from Jen's winks and comments the next morning, I'm pretty sure she heard us.

Riley got to move into the dorm 10 days ahead of the general student population, thanks to her status as a scholarship athlete. Although she was busy with soccer practices, we found time to video chat nearly every night, and had some scorchingly-hot mutual masturbation sessions. Now that we were 18, we didn't worry about keeping our chats free of nudity, and Riley was eager and willing to set up her iPad so that I could see every inch of her tight little body while she made herself come.

Obviously, once her roommate moved in, those sessions came to a halt. When she could get a little privacy for a chat, she told me about her new roomie. "She's a pre-business major, from DC -- seems like a pretty serious student, I don't think she'll be throwing lots of parties or anything."

Two weeks after Riley moved in, her fall semester began. She told me about the classes she was taking -- still intending to go to nursing school someday, she'd settled on an undergraduate biology major. "You're certainly excellent with human anatomy," I teased.

As Labor Day weekend approached, I offered to Riley that I could come to Amherst and spend some time with her. We agreed that I'd drive over for the day on Saturday; when I asked if I should get a hotel room so we could spend the night together, she hesitated.

"It's not that I don't want to, Mark -- I really do. I miss you. But it would be weird to tell Katie that I won't be home overnight on Saturday -- I haven't told her anything about you, yet, so it would be a surprise to her."

I nodded. "I get it, Riley," I said, trying not to let my disappointment show. "We'll have the day together, and then I'll drive back home. No problem."


I pulled up in front of Riley's dorm and spotted her sitting on a brick wall just outside. The fall weather had turned a little brisk, and she was wearing jeans and a long-sleeve UMass hoodie. She looked like the prototypical co-ed, and I told her that when she bounded to my car and climbed inside. "Thanks," she said, hugging me. "It's so good to see you!"

We had a nice day together, grabbing lunch at a local deli, and Riley walked me around the campus, showing me the location of her classes, the student union, and the soccer facilities. The team had already played three games, winning two, and losing one.

"I've been on the field for a grand total of about three minutes," Riley said, frowning. "There are just so many good players ahead of me, I'll be riding the bench all year. They know the system better, know what Coach wants before she even asks."

I wrapped an arm around her shoulders. "Hey, Riley -- it's only your first year. No one expects you to be a starter or a superstar -- give it time. You're an amazing player and I know eventually, you'll get your chance to show off those skills."

"Thanks, Mark," she said. She paused, and looked up at me. "Do you want to see my dorm room before you go?"

I couldn't keep the grin off my face, and I waggled my eyebrows at her. "What do you think?"

She laughed brightly. "Down boy. You'll have to keep your pants on. Katie is probably at the library studying -- she's always studying! -- but who knows when she'd come back."

We walked back to Riley's dorm, and she swiped her ID card to unlock the front door. Her dorm was a four-story brick building, and we walked up a flight of stairs to the second floor, and down a long hallway. The white cinder-block walls and institutional-grey carpet looked very familiar to the Stanford dorm I'd lived in a decade earlier. Riley said hi to a couple of girls as we passed them, and I tried to ignore their curious expressions as she led me down the hall.

Riley unlocked her room and beckoned me inside. A typical double room, she and Katie had a window that looked out onto the grassy quad below. The room was relatively neat, Katie's side impeccably so, Riley's side a little sloppier but not bad.

We made out on her bed a little bit, hands roaming over each other's upper bodies, but I could tell Riley's heart wasn't really in it, so I pulled back. "Are you OK, Riles?" I asked. "Yeah," she said softly. "I'm just worried about when Katie might come back."

"I mean, it's not against the rules for me to be in here or anything, is it?" I asked. "I don't want to get you in trouble."

"No, we have open visitation on the weekends, so it doesn't matter. I just--" Riley's words were interrupted as we heard the jingle of a key in the lock, and as the door opened, I couldn't help notice that Riley moved away from me on the bed. "Hi, Katie," she said quickly as her roommate entered. Katie was a pleasant-looking brunette, dressed in a long skirt and a sweater, wire-framed glasses perched on her nose.

"Hi, Riley," she said, her eyes focusing on me.

"Katie," Riley said in a rush, "I want you to meet Mark. My uncle. This is my uncle Mark." I shook hands with Katie, and the three of us made brief chit-chat for a few minutes before I glanced at my watch, and then at Riley.

"My uncle's got to drive back to Boston, Katie, so I'm going to walk him out," Riley said, grabbing her keys.

"It was nice to meet you, Katie," I said, and Riley and I left the room. Neither of us said a word as we walked the length of the hallway, down the stairs, and out the door towards the visitor parking lot. Finally, Riley spoke up.

"I know what you're going to ask me, and I don't know. I don't know why I introduced you like that. It just seemed ... easier."

I nodded silently, not pointing out that it probably actually made things harder in the long run, and we kept walking. When we got to my car, I leaned against the driver's door, and opened my arms. Riley stepped into my embrace, and I kissed the top of her head. "Don't worry about it, Riley," I said. "If I have to be 'uncle Mark' for a while longer, I'll deal with it."

We kissed goodbye, somewhat awkwardly, and separated, both with an unhappy expression on our faces. Why does this have to be so difficult, I wondered.


Later that week, I got a call from Caitlin, who'd heard about our less-than-spectacular visit from Riley. "I just think Riley's really confused right now, Mark," she said over the phone. "She still loves you, but she isn't sure how to be a college freshman with a nearly 30-year-old boyfriend."

"I know," I said. "I miss her terribly but I don't want to make things harder for her."

"Riley told me that next time she'll probably let you rent a hotel room, and then you guys will have some more private time without worrying about her friends or her roommate, or having to explain who you are."

"That's good to hear," I said. "I was just really hoping the 'Uncle Mark' stuff was over with."

"I know, Mark. Just be patient with her, and remember -- she's only 18. Give her some time."

Over the next several weeks, I tried to give Riley a little more space. I didn't call or text her quite as often, and our FaceTime conversations pretty much came to an end. I didn't bring up the idea of coming to visit her again, and Riley didn't broach the subject either. Her soccer season rolled on, Riley mostly riding the bench, and I quickly learned not to bring up that topic.

So we didn't talk about soccer, we didn't really talk about her friends, and we didn't talk about "us." Our conversations were stilted, awkward, and brief.

I felt us drifting apart, and didn't know what I could do to fix it.


I trudged home from the subway station one Thursday in late October, about a week before Halloween. It had been a long, difficult day at work -- we were behind schedule and over budget on several projects, and I'd had no less than four meetings that day on difficult topics. It was after 6:30 before I was riding the elevator up to my condo, anticipating a beer, a microwave dinner, a bunch of work emails, and a restless night of sleep.

I opened my front door and stepped inside, then stopped in my tracks. She was sitting on my sofa, looking up at me.

Riley.

She was wearing jeans and a sweater, legs tucked up underneath her, shoes next to her backpack on the floor. Her cheeks were tear-stained, her eyes red, and my heart leapt into my throat upon seeing her.

"Riley? Why are you here? What's wrong?" I asked, dropping my laptop case and kicking the door closed.

She wiped at her eyes, fresh tears leaking from the corner, and didn't answer me. I sat down next to her on the couch. "Riley? What is it, baby?"

She broke down in fresh sobs and threw her arms around me, burying her face in my chest. I felt her hot tears through my shirt almost instantly, and I returned her embrace. Rubbing her back, I got bits and pieces of information out of her between the sobs.

"It's just too much, Mark."

"What is, Riley?"

"I never see you -- and I never get on the field -- and I miss my family -- and my roommate is always studying and antisocial -- and the classes are so hard --"

She went on with sentence fragments like those as I held her in my arms, kissing the top of her head, my dress shirt wet with her tears. I rubbed her back and eventually her words petered out, her breath coming in short hitches between her sobs.

She took a deep breath, and I tried not to notice how her breasts moved alluringly against my own chest as she did so. Finally, she leaned back, wiping her eyes, and looked at me, speaking calmly for the first time.

"I'm sorry to dump that on you, Mark. I just -- it's all too much right now, and you gave me that key, and said I could use it whenever I needed to, and I failed a calc exam today, and I just wanted to get away from UMass and come see you."

I held her hand. "Riley, this is exactly why I gave you that key, and you know you are welcome any time. How did you get here?"

She blushed. "I took an Uber. It cost like $110. Mom and Dad will flip when they see my Visa bill next month."

I chuckled. "I'm sure they'll understand. It's only money, and we all did things like this at your age."

"Yeah, right."

I looked at her. "Riley, let me tell you a story about my freshman year at Stanford."

"About three weeks into the semester, I met this girl Tara who lived in the dorm next to mine. Almost instantly, I had a crush on her, was thinking about asking her out, but I hadn't yet."

Riley watched me intently as I continued. "So one day, I had a horrible time in my computer science class. I didn't understand the assignment that the TA was making us do, and so I faked my way through it. I turned it in at the end of class, but I knew it wasn't right -- I knew I was going to get an awful grade on it."

"Already in a bad mood, I decided to skip my English class and go back to my dorm, maybe take a nap or get drunk or something. I open my door, and my roommate Rick is in there. In his bed, his shirt off, a girl on top of him, the two of them making out. Now, guess who the girl was?"

Riley's eyes widened. "No way! Tara?"

I nodded. "Yep. So the two of them were embarrassed of course, but neither one of them knew that I'd had a crush on her. They quickly scampered out of the room, probably up to hers to finish making out or god knows what."

"What did you do?" Riley asked.

"I decided that I had to get the fuck away from everyone," I said. "I threw some stuff in my gym bag and caught a bus up to San Francisco. I found some shitty hotel down by the Wharf and paid way too much for it, like $150/night, and stayed there for the weekend, drinking cheap beer and watching bad hotel room porn."

"You should have heard my parents when they saw that hotel bill," I said ruefully. "They assumed I had shacked up with a girl in the City for a weekend or something. That would have been a better story, but it was just sad lonely me, all by myself."

"What happened with Tara and Rick?" Riley asked.

I chuckled. "They dated for about three months, and broke up after Christmas. So I asked Rick if he cared if I took her out, and he didn't. She and I went out a few times, slept together a couple of times, and you know what -- she was a little crazy, and the sex wasn't even particularly good!"

Riley laughed, squeezing my hand.

"The point of all this, Riley, is to say -- college is hard. Relationships are hard, even friendships in college are hard. And you're a varsity athlete on top of everything, which is something I never had to deal with. It's OK to freak out. It's OK to ask for help, and it's OK to be overwhelmed. We all were, at some point."

She nodded, her lips in a tight line, eyes still watery and red.

"And Riley -- one last piece of advice. Tell your parents about the crazy expensive Uber, tell them you came to see me, before they see your credit card bill. They'll be less freaked out."

She nodded, and moved off into the bathroom to wash her face. I pulled out a Chinese delivery menu, and we ordered some food. While we waited for it to show up, I opened a bottle of wine and we made plans for the next day. "You're welcome to stay here tonight, Riley, and I will drive you back tomorrow."

Riley told me she could miss her one class in the morning, but had to be back in Amherst for a 4:00 soccer scrimmage. I agreed that I'd work half a day, then drive her to campus in the afternoon.

"You don't have to, Mark," she said. "I want to," I told her. "I don't want you to have to take an Uber all the way back. You hang out here in the morning, sleep in, whatever, while I'm at work."

"It would be nice to sleep in a bit, in your nice quiet, comfy bed," she said wistfully. "The dorm is always so noisy."

"There you go. I'll work 'til noon, we'll have some lunch and then hit the road."

"OK," she agreed. "I have some studying I can do in the morning anyway," she said, gesturing at her backpack. "But I better text Katie and let her know I'm not coming back to the room tonight. I'll tell her I'm staying at a friend's or something."

Riley pulled out her phone to text her roommate as the doorbell rang, and I moved to the front door to pay the delivery guy. Over kung pao chicken and some spare ribs, we chatted easily, laughing over old memories and stories Riley told me about her first couple of months in college.

After dinner, we cleaned up our dishes, standing companionably at the sink, Riley bumping her hips against mine. We moved back into the family room and sat on the couch, Riley draping her legs across my lap. After we'd finished off the bottle of wine, Riley made a shy request.

"Mark? Do you think we could take a bath together, like we did that one time at your old place?"

"Yes, Riley. Oh god, yes."

I ran us a hot bath and, as the tub filled up, watched Riley strip off her clothes. Her body was magnificent, her stomach smooth and flat, her ass tight, her legs long and strong. "I think college soccer is good for you," I said. "You look amazing."

"Thanks," she said, blushing.

We climbed into the tub together, each of us caressing and kissing the other softly, slowly. Neither one of us seemed to be in a rush, even though we hadn't been intimate for a couple of months. Again, it seemed to be one of those times where she knew exactly what I needed, and vice versa.

Eventually, our passion grew as our patience ran out. Riley eased me back into a sitting position against the cold porcelain wall of the tub, and she straddled my lap. Reaching behind herself and between her own thighs, she grabbed my cock, aiming the head so it pointed to her center, and she eased herself down on me. I closed my eyes in ecstasy as her tight, hot pussy surrounded my cock, and our moans echoed off the bathroom walls as we fucked.

Riley rocked her hips back and forth, working her way down until I was fully inside her, then pulled up and dropped back down, up and down. I pushed my hips up to meet her thrusts, and I watched her throw her head back in pleasure as she tilted her hips, pressing her clit against my shaft.

I clutched at her ass with both hands, pulling her young body towards me, my head dipping down to suckle at her nipples. I licked and nibbled each one in turn, loving the feel of the hard, puckered flesh against my lips and tongue.

The wet, soapy water let my hands slide easily across her tight cheeks, and my pointer finger slipped down between them, the tip brushing across her asshole. She jumped with pleasure, and I repeated the motion. The soapy water let my fingertip penetrate her anus just a little bit, and she shivered with pleasure against me. "Ohgod, ohmygod Mark that's soooo good, so nasty."

I slid my fingertip out of her ass and then pushed it back in, a little further. I felt her pussy contract around my cock, her hips quivering. "Ohgod Mark, don't stop ohgod." I pulled my fingertip out, then put it back in, in and out, trying to keep the same rhythm as my cock sliding in and out of her pussy.

"Ohhhhh yessssssss," she moaned, her internal muscles clutching at my dick. "Coming!" she cried out, and I felt her orgasm ripple through her body. I pushed my cock through her clenching walls, my fingertip a little further into her tight asshole, and I let myself come with her, my semen blasting deep inside.


The next morning, I slipped out of bed and quietly showered while Riley slept. I ate a quick breakfast and kissed her goodbye before I left, telling her to help herself to whatever I needed.

I spent a distracted morning at work, rearranging some meetings so I could leave at lunchtime. I headed home and Riley and I had sandwiches and potato chips at my kitchen table, before we climbed in my car and headed for Amherst.

As I navigated I-90 away from the city, Riley and I talked about what she could do to get back on track a little bit, and avoid any future meltdowns. "As much as I love seeing you, Riles, I don't want you spending $100 on an Uber ride every time you get a bad grade," I said, and she nodded her head in agreement.

One by one, we worked our way through what was bothering her. Her roommate, while not ideal, wasn't causing that much trouble. "Is she bad enough that you want to try and switch for next semester?" I asked.

"No, I don't think so," Riley said. "I think I'll just wait it out this year, and some of the girls on the team are already talking about rooming together next year. I think I'll probably live with another soccer player next year."

We talked about her academic difficulties -- which were relatively minor -- and Riley told me that the athletic program had tutors readily available for varsity athletes. "I just -- I've never needed a tutor before, you know?" she said. "I've been a tutor for other people, but I never needed any extra help in high school."

"This isn't high school though," I pointed out, gently. "It's okay to ask for help, and your coaches want you to if you need it. You're not any good to them if your grades aren't good enough to stay on the team," I said.

"I know," she admitted. "I'll call for a calculus tutor this week."

We talked about how much she missed her family, and that she wouldn't see them until winter break. "Do you FaceTime with them?" I asked, knowing that mine and Riley's own video chatting frequency had dropped to almost nothing.

"Not really," she admitted. "It's hard to find the privacy, Katie's always studying in our room and I feel bad for making noise. Maybe I could talk to them more from the lounge or something. I just hate that I won't be there for Thanksgiving -- and my birthday, which is the Monday after," she said. "But we have a game in Maryland on that Saturday, so it didn't make any sense to fly home for like two days and then come back."

"Yeah, that would be hard," I said. "Is the rest of the team staying in town?"

"Most are local, so they're driving to their parents for at least Thanksgiving Day," she said. "There are four of us that I know of -- all freshman and sophomores -- that will be in town. We'll eat McDonald's or something, real traditional."

I laughed, then thought of something. "Riley, why don't you and your friends come to my place for Thanksgiving, and I'll cook a turkey. I'm going to be alone this year too."

She smiled, grabbing my arm. "Really? Oh wow, that would be so cool. Hannah has a car, so she could drive us. Do you think that you could do that, you wouldn't mind?"

"I wouldn't mind at all," I said. "I'm not sure what we'd do for sleeping arrangements -- my couch pulls out into a bed, so if you guys didn't mind doubling up, we could do two on the sleeper, two in the guest room. Or you could just bunk with me, you know, for efficiency," I said.

Riley giggled. "Well, I know Missy and Parker won't mind at all to share a bed, seeing as how they're a couple."

"Oh," I said.

"But as for the other ... I don't know. It'll be less complicated if I just share the sleeper sofa with Hannah, but I'm not sure. Part of me wants them to know about you, to know all about us," Riley said, softly. "But part of me doesn't."

"I know, Riles," I said. "It's complicated. Whatever you decide, I'll be OK with."

"Thanks, Mark."

As we neared Amherst, Riley asked if I wanted to stick around and watch their scrimmage. "We split up into four teams, so I actually get to play, unlike in a real game."

I readily agreed, and she told me how to get to the soccer practice field from her dorm. "There's usually a handful of people in the stands, especially when the weather is decent like this," she said.

I dropped her off at her dorm, and she leaned over to give me a quick kiss before climbing out. "Thanks for everything, Mark. I love you."

"I love you too, Riley."

I killed a little time browsing in some shops near campus until almost 4, then headed over to the practice fields. As Riley mentioned, there were a few dozen people hanging out in the stands. I watched as the team came out, and they split into four squads, two using each half of the field for their mini-scrimmages.

I spotted Riley pretty quickly, wearing a white uniform with a maroon "17" on the back. She worked the ball up and down the field as they scrimmaged, her team on offense first. She was just as fast (or probably faster) than she had been before, but unlike in high school, most of her teammates could keep up with her. I held my breath as a larger girl sent Riley tumbling to the ground when they both went for a loose ball, but Riley popped back up, brushing the grass off her butt.

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