The Arrangement - Cover

The Arrangement

Copyright© 2016 by MarkStory

Chapter 13: A Sophomore Separation

Coming of Age Sex Story: Chapter 13: A Sophomore Separation - 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  

As difficult as Riley’s first year of college was for us and our relationship, her second year ended up being even worse.

Over the summer, we kept in touch, somewhat infrequently. She was busy with soccer, with work, and with catching up with high school friends. We didn’t talk more than once a week, maybe about half that time video chat. When we did talk, we got along well and the conversation flowed easily. I think a little of the pressure was off us both, with us being 1200 miles apart.

Becca and I continued to get together as well, once or twice per week. Despite her insistence that we weren’t in a relationship, I grew fond of her and knew that if she weren’t moving to California, we might’ve had some potential. I gave her lots of information about Stanford, about fun spots to hang out in Palo Alto, and she seemed appreciative. Our sex was varied and fun, though our conversations tended to focus on one or two topics and quickly got pretty stale.

Still, we had a teary goodbye in August, on our last morning together. She was driving her car cross-country to Palo Alto and would be leaving in a couple of days. We promised to stay in touch via email and Facebook, and I wished her luck in graduate school.

“Good luck to you, too, Mark,” she said, hugging me tightly. “I hope you get what you want someday.” I’d made veiled references to a girl at UMass and a complicated relationship, but I didn’t give her too many details about Riley. In a way, I felt disloyal to them both whenever I discussed one with the other, so I avoided doing so.

Later that same Saturday, after I’d said goodbye to Becca, Riley called me. After some pleasant small talk, I asked her when she was coming back to Amherst.

“So that’s kind of why I called, actually. I’m flying into Philly on Friday and staying at Hannah’s for the night. She and I will then drive up to Amherst early Saturday morning. I was wondering, do you think you could come over and help us move into our room?”

Of course, I agreed.

The next Saturday, I drove over to Amherst and met Hannah and Riley in the early afternoon outside their new dorm. Both of them hugged me, Riley squeezing me tightly and kissing me on the cheek. “I missed you,” she exclaimed.

“I missed you too, Riles.”

Hannah maneuvered her car into a space near the loading dock elevator, they checked in and picked up their keys, and I helped the girls carry boxes and boxes up to their new room. As sophomores, they qualified for slightly better living arrangements -- they had a two bed room that shared a bathroom with the room next door.

It took us an hour or so to unload Hannah’s car, and then another couple of hours to get things organized in their small room. I helped the girls get their TV hooked up, their fridge plugged in, and get most of their boxes unpacked. We were pretty sweaty and dusty when all was said and done, and Hannah claimed first dibs on the shower. She took her clean clothes into the bathroom; as the door locked behind her, Riley slumped bonelessly into my lap.

I hugged her, gently. “That was a lot of work, right?”

She nodded, nuzzling her face into my neck, and I felt my cock stiffen beneath her firm ass. She felt it too, wiggling her butt against me.

“Hannah asked -- she asked something kinda weird on the drive up here,” Riley said softly. “She asked if I’d want some ‘private time’ with you this afternoon.”

“She did?” I asked. “Does she know about -- about us?”

Riley shrugged. “We’ve never talked about it, but she always uses air quotes when she says something about my ‘uncle Mark.’”

I nodded. “She kind of said something like that to me when you guys were leaving after Thanksgiving last year, something about me having a really good night. So she might have known you snuck into my room.”

“That makes sense,” Riley said. “That’s probably when she started doing the ‘uncle Mark’ thing.”

“So,” I said, trying not to sound over-eager. “What did you say when she asked about private time?”

Riley looked at me, smiling. “I told her that would be nice, that you and I had a lot of ‘catching up’ to do.”

Twenty minutes later, I moaned with pleasure as my cock slipped in and out of Riley, the blonde bent over against her shower wall, the water beating down us as I fucked her. “Ohmygod, Mark, so good.”

I grunted in agreement as I continued pushing in and out of her, my balls slapping against her perfect, tight, upturned ass. I couldn’t help but compare Riley to Becca, my most recent sexual partner, and Riley came out ahead in nearly every category. Her skin was smoother, her ass nicer, her legs more firm, and her pussy so much tighter. Her lips gripped me on each outstroke, and I pushed through them on the reverse each time, reveling in the feel of Riley’s hot wet channel around my cock.

I reached around Riley’s torso to fondle her dangling breasts, and just for a moment I was surprised at how small they were, my recent experiences with Becca and her DDs fresh in my mind. I quickly pushed those comparisons out of my head, fondling Riley’s hard nipples between my thumb and forefinger, making her squirm with pleasure.

She pushed her ass back at me, meeting each thrust, demanding that I fuck her harder and harder. I increased the pace, complying with her requests, feeling my cock stiffen even more as I stroked it in and out of Riley.

Riley dropped one hand between her own legs and played with her clit, her fingertips brushing against my shaft and my balls. I felt her internal muscles spasming and kept pushing my cock through her wetness, listening to her cry out in pleasure as the orgasm racked her body. “Ohgod Mark, oh so good so good ohmygod!”

Her cries of pleasure set off my own climax, and I pushed deep inside Riley as I felt my release pour into her.

We were dressed and clean when Hannah came back about an hour later, and the three of us decided to pick up a pizza for dinner. I insisted on buying -- they were poor college students, after all -- and I only put up a token resistance when they asked me to stop and get some beer for their fridge as well.

We took the bounty back to their room and sat around, eating pizza and drinking beer. Riley and I sat next to each other, close but not quite touching, while Hannah sat across from us. She took a long pull from her bottle of Sam Adams and then set it aside, looking at us. “So, I’m guessing you two had fun ‘catching up’ this afternoon?”

Riley blushed and looked away; I took a drink from my own beer to cover the sudden grin which broke out across my face.

Hannah laughed. “Riley’s blushing, Mark’s smiling, so I think I have my answer!” When neither of us confirmed her guess, she continued. “I have to know -- what’s the deal with you guys?”

I looked at Riley, who didn’t immediately answer. “Well,” she eventually began. “It’s complicated.”

“But he’s not really your uncle, right?”

I shook my head. “I’m not. Let’s just say -- let’s say we’ve been friends for a long time, very good friends.”

Hannah laughed. “Hmph. I’d like to have a ‘good’ friend like you, judging from how much Riley’s blushing!”

All three of us laughed, and Hannah continued. “Seriously though -- how old was Riley when you guys first met? Mark, how old are you -- that picture in your bedroom, Riley’s a lot younger.”

Riley looked at me with wide eyes; I’d never told her that Hannah asked about our formal picture last year. “Well, Hannah -- I’m 29, and Riley’s now 19. When we met ... well, in that picture Riley is 10 years younger than me.”

Hannah laughed. “Of course, duh. That doesn’t tell me anything!”

I glanced at the clock. “Um, it’s probably about time for me to head back to Boston, so maybe you guys can talk about this without me?”

“You chicken,” Hannah said lightly.

“Hey now,” I said, “no need for name-calling. Especially to the guy who bought you pizza and illegal beer.”

“You’re right, you’re right,” she said, holding her hands up in surrender. “I guess I shouldn’t be surprised you bought us that beer -- it’s probably the least of your sins concerning minors, huh, ‘uncle Mark?’” she said, winking at me.

Again, Riley’s blush and my smile were probably the only answers she needed.


Riley quickly got busy with soccer practice, telling me that she might be a starter this year; the team had graduated several players in the spring. “At the very least, I should play a lot more than I did last year,” she told me, the excitement in her face visible on my iPad screen.

“Great,” I said. “I’ll try and come to some games this year.”

The next day at work, my boss made those plans a lot easier. “So, Mark,” he began. “We got the sub-contract from Robinson Brothers out at UMass for the new academic support building. We’ll be doing site prep, utility relocation, and some other...”

Charlie went on talking about other details of the project, but I didn’t hear a whole lot after he said the word “UMass.” Fortunately, he recapped what he needed from me at the end of his spiel, and I tuned back in.

“So, I’ll need you over in Amherst for like four weeks or so, probably early September to the first of October. We’ll have a bunch of planning meetings and some initial site work, trying to get done what we can before winter gets here. This will likely be a two-season project, so we’d finish up next spring or fall.”

“We’ll put you up in some extended-stay hotel out there, you can come back to Boston on the weekends if you want, or you can stay in town and go out and pick up college girls or something,” he said, winking at me.

Oh, if you only knew the truth, I thought to myself, chuckling lightly at his jokes.


The four weeks I spent working in Amherst flew by, but were a great time for Riley and I. The work kept me busy during the day, which was OK since she had classes all day. But we’d get together 3 or 4 times during the week, either in my hotel room or in her dorm. Since Hannah was in on a little bit of our secret, Riley didn’t seem to mind me coming over there, though I still got some odd looks from the other girls on her floor. I was too young to be someone’s dad, but older than the typical students at UMass, so the other residents didn’t quite know what to make of me.

I got to know Hannah better as well as I spent so much time on campus, and I could see why she and Riley got along so well. She was smart like Riley, with a wicked sense of humor. From veiled comments the girls made to each other, I also inferred that she was pretty sexually active, even though she didn’t have a boyfriend. A couple of times, when Riley told Hannah that she’d be staying over at my hotel and not coming back to the dorm that night, Hannah would point out that she didn’t expect to be back in the room either!

Riley and I had some amazing sex all over my room at the Residence Inn, in the bed, on the L-shaped couch, and in the huge shower. I gave her a key to the room, and she used it as a study space during the day as needed -- the hotel was either a long walk or a cheap Uber from her dorm room. She cooked me dinner a couple of times, using the room’s kitchenette, and it was an amazing surprise to come “home” from work, and find Riley making dinner wearing just a hotel robe -- or less. Though we weren’t living together full time, I couldn’t help but wonder: Is this what it might be like for us, someday in the future?

She was insatiable once we got behind closed doors, and several mornings I’d head off to a meeting at the project site with an ache in my groin but a huge smile on my face.

On one memorable occasion, I fucked Riley from the rear, standing behind her, my body pressed against her as she pressed her front against the cold glass of the room’s window. Her nipples dragged up and down against the hard surface as she looked down on the parking lot from our 5th floor room.

“Ohmygod,” she moaned. “It’s so cold on my tits and anybody down there can see me if they look up and ohmygod this is so hooottttttttt.”

I grunted in agreement and kept fucking her, bending my knees to keep us at roughly the same height, slamming my cock in and out of her until we both cried out in ecstasy.

Mark watches with pleasure as Riley dominates the soccer field for her college team.I also got to see the soccer team play several home games, and Riley’s prediction turned out to be accurate -- she was the starting right midfielder for the team this year. Hannah got a lot of playing time as well, a defender on Riley’s side of the field. The team won 4 out of the 5 games I was able to attend, with Riley scoring goals in two of them, and both she and Hannah were thrilled with how the season was starting.

I saw Riley’s teammates Missy and Parker, who’d stayed with me last Thanksgiving, a couple of times after games. I didn’t meet any other teammates, nor Riley’s friends in the dorm or from her classes. I got the feeling that she was still trying to keep our relationship separate from her college life, and I didn’t push it.

It was great having Hannah in on our secret at least, and there was no problem with me being in their room. A couple of times Riley and I even fucked in her dorm, knowing that the other girl was at class or in a study session. That was incredibly exciting -- for both of us -- as we eagerly thrust against each other in her narrow dorm bed, the springs squeaking, my sweet little college co-ed spread-eagle below me as I slammed in and out of her.


Unfortunately, my four weeks in Amherst came to an end all too soon, and I moved back to Boston. The project wouldn’t need my input again for a year or so, and even then, it wasn’t certain that I’d need to stay in town for a month again.

Riley and I went back to our long distance arrangement. Around three weeks later, the weekend before Halloween, I drove over to Amherst to see a home soccer game. I didn’t tell Riley I was coming -- indeed, I didn’t make the final decision to go until that morning. I was bored at home, and wanted to see her, so I hit the road in time to make the 2PM kickoff. The team had a tournament in North Carolina over Thanksgiving weekend, so unfortunately, we couldn’t repeat our holiday from last year, and so I wasn’t sure when we’d see each other again.

It was an exciting game, UMass beating Richmond in overtime. I got to see Riley score a goal in the second half, a laser like shot that she slammed into the upper left corner of the net. I watched and cheered with excitement as her teammates swarmed her, Riley’s smile visible even from my bleacher seat.

After the game ended, I hung around, hoping to get a chance to say hi to Riley. I made my way down to the field, greeting Missy along the way. I saw Riley near the far end of the bench, talking to a guy that looked roughly her age, maybe a bit older. She was laughing at something he said, touching his elbow, and I couldn’t control the jealousy that flared through my gut.

“Hi, Mark!” Hannah said brightly, stepping into my field of vision. She was sweaty from the game, bits of grass in her hair, but she looked happy.

“Hi, Hannah. Great game!”

“Thanks -- I didn’t know you were coming today, Riley didn’t tell me.”

“I didn’t tell her, just decided to drive over this morning as a surprise. I’ll say hi to her when she’s done over there,” I said, gesturing to where she was still talking to that guy.

Hannah nodded. “Oh. Good to see you!”

“You too,” I said, sitting down on the bench. I watched Riley out of the corner of my eye, and could see her nodding her head as the guy asked her a question. After another 5 minutes, their conversation broke up, and the guy headed off the field. Smiling broadly, Riley picked up her duffel bag and started walking towards the locker facility, and that’s when she saw me.

“Mark! Hi Mark,” she said. She dropped her bag and gave me a quick hug. “I didn’t know you’d be here -- I mean, it’s good to see you but I didn’t know,” she said. I wondered if there was a slight tone of guilt in her voice.

“Yeah,” I said. “I didn’t have plans today and wanted to see you play, so I decided on kind of a spur of the moment thing to drive out. You played great -- that goal was awesome!”

“Thanks,” she said, shyly.

“So,” I said -- “do you want to catch dinner or something after you’re done here?”

“Oh, um,” she said, her eyes darting in the direction where the guy’d walked off, and I knew what she was going to say before she said it.

“I kind of just made plans for tonight,” she said. “Um, I kind of have a date.”


The rest of our conversation there on the field was awkward, and I think we both were relieved when I said I had to go. We hugged goodbye, and I drove back home, my feelings unsettled.

Eventually, via phone and email conversations with Riley (and a couple with Hannah) I learned some more about this guy. His name was Tom, and he was a grad student at UMass. Riley had met him at some sorority party, and he’d been coming to most of their home games. The day I’d been there had been the first time he’d asked her out.

Conversations with Riley over the few weeks were a bit weird. I could tell she liked Tom, she went out with him a few more times, and she wanted to tell me about him. At the same time, I knew she felt awkward doing so, and I didn’t really want to hear about him. The whole problem was that we’d never properly defined our relationship -- were we a couple? Friends with benefits? Some other undefined category? Neither of us had ever really known.


Riley’s birthday fell on the day before Thanksgiving that year. She was turning 20 -- my sweet little teenager was leaving her teen years behind. I’d sent her a pair of earrings and a card, and I called her that morning, wanting to catch her before the team left for their tournament.

“Hello,” she answered sleepily.

“Hi Riles,” I said, glancing at the clock -- it was 10AM, was she still asleep? “Sorry if I woke you, I just wanted to say happy birthday to my favorite no longer teenager!”

She giggled softly. “Thanks, Mark. And thanks for the present!”

“You’re welcome,” I said. In the background, I could hear a muffled low voice, and I could barely hear Riley whispering something. With a sinking feeling, I realized she’d had an overnight guest.

“Well, anyway, I uh, won’t keep you. Happy birthday, and good luck in your games. I love you.”

Riley paused at the other end of the phone, and her reply broke my heart a little bit. “You too. Bye!”

At my desk at work, I set my phone down and buried my head in my hands, trying not to picture Riley and Tom in that bed together. They were probably already naked, and she’d set the phone down, turning to him, embracing him. He’d make some stupid joke about giving her what she really wanted for her birthday, and then they’d make love in that dorm bed, the same one where’d I had made love to Riley, only a couple months ago.

I got really drunk that night, and I woke up on Thanksgiving morning with a splitting hangover. Since I was alone that year, it didn’t hugely matter -- not like I was cooking a turkey or anything. I moped around the house most of the day, and had a pretty crummy weekend in general.


A month later, I was in California visiting my family for Christmas and New Years. My father’s health had taken a turn for the worse in the past year, and my mom and my sister had moved him into a managed care facility. We didn’t really expect him to celebrate any Christmases past this one, so it was a dark and depressing time for all of us.

One night, between Christmas and New Year’s, my sister and I were the last ones awake, polishing off a bottle of wine. We talked about her boyfriend -- he was a nice guy, and she expected him to pop the question pretty soon, maybe even on New Year’s Eve.

“What about you, Mark?” she asked. “Are you seeing anyone?”

I sighed. “Tough question, Steph. Kind of. I mean, not really -- she has a new boyfriend now, apparently.”

Stephanie gestured towards me with her wine glass, prompting me to continue. So, over another half bottle of wine, I told her the story of Riley and I. I didn’t tell her about the Arrangement portion, but told her everything else -- how we’d met on the ship, how young she was when we met, how she moved to UMass and I thought that would be great for us, how hard it was for me to integrate into her college lifestyle, and how much it killed me -- absolutely killed me -- that she had a boyfriend.

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