The Arrangement
Chapter 15: Senior Year and Beyond

Copyright© 2016 by MarkStory

Coming of Age Sex Story: Chapter 15: Senior Year and Beyond - 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 summer between Riley’s junior and senior years was a wonderful three months, the first time Riley and I truly lived together. All of the lingering questions about our relationship were answered, I knew we’d be together forever. Although we weren’t engaged (yet!) we might as well have been, and we weren’t shy about being affectionate in public or in private.

Of course, only two days after Riley moved in with me, we straddled that “public / private” line, having sex on my balcony shortly after dark one night. I knew it was a fantasy of Riley’s, and so after we’d cleaned up from dinner, I pulled my own clothes off, then started undressing Riley, not saying a word as she looked at me curiously. The excitement and delight in her eyes as I took her by the hand and led her out to the balcony was wonderful to see.

The balconies in my building were semi-private, screened from the neighboring balconies by brick walls on each side, though the railing facing the cityscape was plexiglass instead. I laid down on the lounge chair and Riley climbed on top of me. We made out until my cock was hard and her pussy dripping, and then she slowly slid me inside her, riding me until we both exploded with pleasure.

The balcony sex became a frequent diversion for us that summer, and we eventually got more daring, moving out there just before dusk. A few times, we fucked standing up, Riley’s hands braced on the balcony rail, her breasts bouncing just behind it.

As far as I know, no one ever saw us!


We had a wonderful visit with Riley’s folks, showing them some of the touristy sites around Boston. As Jennifer had said to me when they arrived, they were really, truly very happy for us both, and they welcomed me into the family enthusiastically, though (again) unofficially!

A week after her parents visited, we headed out to California. My sister and her fiance Danny were getting married in Santa Cruz, and once Riley and I got together in the spring, we made plans for her to come with me. We decided to fly out a few days early -- Riley hadn’t spent any time in San Francisco since she was a little kid, and she was also curious to see the area where I grew up and went to college.

We held hands on the flight from Logan to San Francisco, and Riley confessed that she was nervous about meeting my family, especially my mom and my sister.

“What if they don’t like me?” she asked. “I’m so much younger, what if they think I’m just a kid?”

I leered at her. “First of all, no one would look at you and think ‘just a kid, ‘“ I said, making her blush. “Secondly, my sister especially knows how I feel about you, knows the depth of our relationship, and couldn’t be happier for us. I’m sure she’s relayed a lot of our story to my mom, too -- Steph has always been terrible with secrets.”

Riley laughed, and we leaned back in our airplane seats in companionable silence.

The trip to California was great. We spent two days in San Francisco, acting like goofy tourists in love. We rode the cable cars, walked out onto the Golden Gate Bridge, ate seafood at Fisherman’s Wharf, visited Chinatown, and wandered through the Haight and the Castro. Our room at a boutique hotel near Union Square had a lovely view of the bay (and the Bay Bridge) from the 11th floor, and we left the windows open as we made love on the four poster bed, the cool salt breezes adding to the overall romantic effect.

After two nights in San Francisco, we moved to my mom’s house in San Jose. Mom was as cordial and welcoming to Riley as she could be, and despite the frantic wedding preparations all around us, she invited Riley to lunch on our first day there, telling me I wasn’t invited. “We need some girl talk,” she said, and so I met up with an old college friend still in the area.

That night, as we snuggled under the covers in my mom’s guest room, Riley told me about the lunch. “Your mom is so sweet, and so happy for us,” she said. “She asked me if I thought the age difference was a problem, and I said I didn’t. When I told her that, she said ‘good enough for me’ and then waved down the waiter to get us a bottle of wine.”

I laughed. “Yep, that’s mom all right. She’s pretty easy going.”

The next day, I showed Riley the house where I spent my childhood (my parents had sold it long ago, after Stephanie and I moved out), and then we drove to Palo Alto and walked around Stanford for a bit. I showed her my old dorms, the engineering buildings, and we walked through the bookstore to pick up some Cardinal paraphernalia.

Riley looked around the campus wistfully as we walked back to our rental car, hand in hand. “Don’t you kind of wish we’d gone to college together?” she asked. “Spent the night in each other’s dorm rooms, skipped class together, graduated together, all that stuff?”

I nodded. “Sure, Riley. But we’re getting some of that experience -- after all, I have spent the night in your dorm room, and I intend to do that a lot more next year,” I said, wiggling my eyebrows at her.

She laughed, smacking me on the shoulder with the Stanford Bookstore bag she was carrying.

My sister’s wedding was a beautiful ceremony, Stephanie looking radiant in her white gown. I didn’t know Danny too well, but he seemed like a good guy and clearly adored Steph. The wedding was small, maybe 50 guests or so, followed by a casual reception in the church social hall. My sister made time to chat with Riley, hugging her like an old friend the first time they saw each other.

Late in the reception, I was dancing with Stephanie while Danny and Riley moved around the dance floor. I watched as he twirled her, her lightweight dress swirling around those gorgeous legs, Riley laughing with delight.

“She’s so perfect for you,” my sister said softly, bringing my attention back to the bride in my arms. “I’m so happy, Mark. For you and for me.”

I smiled at her. “I’m happy for us both, Steph. Danny is so good for you, and I’m so glad that Riley could be here for this. I love that you, and Danny, and Mom have made her feel so welcome this week.”

“Odds are, Mark, if you love someone, we’re going to love them too,” she said. “We’re pretty alike, you and Mom and I. And I think Dad would have loved her too.”

“He would have,” I agreed. “And he would have told me how good her cleavage looked in that dress.”

Stephanie laughed aloud. “He surely would have!”

A short while later, we blew bubbles at the bride and groom as the headed off to their waiting limo, and their upcoming honeymoon in Hawaii, Riley clutching my arm tightly. I could see from the look in her eyes that the romance of the afternoon and evening had affected her, and knew we’d be making love (as quietly as possible!) when we returned to the guest room at my mom’s house.


The rest of the summer went by fairly quickly, as we settled into a routine. Riley’s internship at the hospital was only 25 hours per week, so she had some spare time that she filled with a workout routine and a little Boston tourism. Most days, she was home before I was, and she always tried to surprise me with something when I walked in the door.

Sometimes, it was Chinese takeout from our favorite local place, ready and waiting on the kitchen table.

Sometimes, it was a home-cooked pot of spaghetti.

Sometimes, it was Riley herself, naked and waiting for me on the couch or in the bed. A couple of times, she texted me pictures as I was on my way home. Maybe a shot of bare legs stretched out on my coffee table; or a tantalizing swath of her naked upper chest and shoulders; or, more daringly, just a single nipple, closeup.

After one such encounter, after we made love on my couch and were recovering, sweaty and panting, Riley giggled and turned to me. “Remember when me sending you a picture text like the one today would have been illegal?”

I laughed. “I surely do. And I wouldn’t trade how we met for anything, but I am so glad we don’t have to hide things anymore.”

“Me too.”

“In fact,” I continued, “Since it’s legal, I showed your nipple to everyone on my train.”

“Mark!”


We had a wonderful (if too short) visit to Florida to see Riley’s family in August. Caitlin and Steve’s baby was adorable, and at nearly 8 months old Emma was crawling up a storm, trying to get into every cabinet, box, and container that wasn’t nailed shut. Cait and Steve looked pretty exhausted, but also deliriously happy.

One day, while Riley visited some high school friends, I chatted with her parents about our summer, the upcoming school year, and beyond.

“Jen and I are assuming Riley will want to move in with you next year, after she graduates,” Jim said. “She’d probably be able to find a job pretty easily in Boston.”

“That’s my assumption too,” I said.

“We’d of course like to have you both closer, but I know Riley really seems to like Boston, and your job is there,” Jen said. “When Jim retires in a couple of years, we’ll be able to come visit more often.”

“You’re always welcome,” I said.

We chatted for the rest of the afternoon until Riley returned, with her friend Jessie in tow. “I just wanted to come in and say hi to ‘Uncle Mark, ‘“ Jessie said, making exaggerated quotation marks with her fingers. I blushed, and greeted her with a hug. “Hi, Jessie. It’s good to see you again -- how’s UCF?”

“It’s great,” she said. “And I’m so happy for you guys, finally being together.” She turned to Riley’s parents. “I knew that ‘Uncle Mark’ stuff was crap a long time ago, before we graduated,” she said. “I could tell they were doing it.”

“Jessie!” Riley exclaimed. “Don’t say that in front of my parents!”

Jim and Jen laughed. “It’s not a big deal,” Jen said. “Jessie, of course we had to keep it quiet back then, for obvious reasons. But it doesn’t matter now, and we’re all just as happy for Riley and Mark, too.”


After our Florida trip, it was unfortunately time to move Riley back to Amherst for her senior year. Once again, she’d be living with Hannah, Missy, and Parker, and their soccer practices began in mid-August.

Riley and I packed up her things, though I encouraged her to leave what she could at my place -- most of her winter clothes, for example. I drove her to Amherst, both of us kind of melancholy that our wonderful summer had come to an end. We had nine more months of being two hours apart, and neither of us were looking forward to them.

As we pulled into a loading dock spot next to Riley’s building, I took her hand. We’d both been quiet for the last 30 minutes or so. “Hey, Riles -- look at me.” When she did so, I continued. “It’s just one more school year. We’ve been through the hard part already. I’m going to come visit as much as I can, and you can come visit me once soccer is over. We’ll figure out how to be together at Thanksgiving, and Christmas, and Spring break. And then in May, we’ll be living together for good!”

Riley nodded. “I know all that. But this summer has been sooo nice, and it went too fast. I wish you had work in Amherst again this year.”

I sighed. “Yeah, me too.” My company’s project at UMass had been completed the previous spring, and we didn’t have any current projects on campus. “But I’ll come to visit as much as I can, I promise.”


On average, I drove to Amherst every third weekend or so that fall, but the schedule was dependent on the soccer team -- obviously I wasn’t driving over for the weekends when Riley and the rest of the team were out of town! Riley was completely comfortable with me staying in her bedroom, and the other girls in the suite were cordial and welcoming to me. They often held team parties on Friday nights, and before long, all of their friends simply accepted me as Riley’s boyfriend. (I did see Peyton a couple of times, which was slightly awkward; after a while, she simply stopped coming to their parties that year.)

For the second year in a row, the girls had made some changes in the apartment. Missy and Parker shared a bedroom, pushing a twin bed across the hall from the fourth bedroom, and pairing the two twins to make a king-size equivalent. The fourth bedroom, then, was an “extra” and the girls used it as a spare room / extra closet.

The first couple of times I stayed there, the other three girls (Hannah especially) had made jokes about squeaky bed frames, and Riley blushed bright red, realizing they might have heard our “activities.” But, she quickly learned to tease them back, and Hannah had frequent overnight visitors, so all four of them accepted the teasing gracefully.

On a couple of weekends, when the team didn’t have a game, I’d rent a hotel room and Riley would come spend a night or two with me there. It was a nice change of pace, plus we had a bigger bed to play on! Although I loved snuggling with Riley in her twin-size dorm bed, I often woke up with a reminder that I wasn’t as young as I used to be, with a crick in my neck or an ache in my back!

On one such weekend in mid-October, I arrived in Amherst late on Friday night and checked in to the Residence Inn. I texted Riley and hopped in the shower, washing off the grime of the day while I waited for her to arrive. I had just dried off when I heard a knock on the door; wrapping the towel around myself, I hurried to let Riley in.

“Mmmmm,” she purred when she saw how I was dressed. She slipped into the room, kicking the door closed behind her as her hands roamed over my bare chest. She was wearing a silky blouse and tight jeans, and I caressed as much of her as I could reach.

Riley tossed her overnight bag onto a chair and kissed me, walking me backwards into the room. I felt her hands at the towel, and it dropped to the floor, leaving me naked. Riley’s hands moved over my cock, which quickly stiffened in her hands, and she dropped to her knees in front of me. “Mmmmm, is this for me?” she asked reverently, placing kisses on my shaft.

“God yes,” I moaned as I felt her hot breath on my cock. I tangled my fingers in her hair as she began sucking me, my cock stiffening fully inside her wet, hot mouth. She bobbed up and down on my dick, her fingers teasing the base of my shaft and my balls.

She pulled her mouth off my slick cock with a “pop” and looked up at me, stroking my shaft lightly. “Mark, this probably isn’t the fairest time to ask this -- but, um, do you think Hannah could, like, join us tonight?”

My cock throbbed in her hand, and Riley giggled as she felt it. “Do you mean -- join us?” I asked, emphasizing the word and making vaguely sexual gestures with my hands.

Riley nodded. “She really wants to, she wants to be with me and be with you, and I told her we’d all have to be together, that was the only way.”

I closed my eyes and imagined the situation, the pleasures of a threesome obvious in my mind from past experiences. “God yes, of course she can, Riley -- as long as you’re cool with it!”

Riley’s eyes twinkled as she sucked me back into her mouth, pulling her phone out of her pocket. She pulled her mouth off my dick long enough to say “Hey Siri -- call Hannah!” and I laughed as she then immediately plunged her mouth back over my cock.

Hannah’s voice came over the speakerphone. “Hello?”

Riley pulled her mouth off my cock, again only for a brief moment. “Hey Hannah -- guess what I’m doing right now,” she said, and then resumed sucking me, making exaggerated wet sounds as she did so.

“I don’t -- wait, that kinda sounds like -- ohgod, are you sucking him off right now?”

Riley pulled off again. “Yep!” she said proudly, “and I think he’s getting close,” she said, pushing her mouth back onto my shaft. I moaned in agreement.

“Ohmygod, that is so hot,” said Hannah from the speaker phone. “So um -- did you ask him?”

“Mmmhmmmm,” Riley moaned around my cock, loud enough for Hannah to hear.

“Ohgod,” Hannah repeated.

Riley pulled her mouth off again. “So listen to me make him come in my mouth, and then get your cute little ass over here. Room 322.”

She pushed her mouth back onto my cock, sucking me even harder, and Hannah and I both said “oh god,” simultaneously. Riley waved her phone at me, and I held it in my left hand, my right hand tangled in Riley’s hair, urging her on. Faster and faster she sucked me, both hands now free to play with my balls, and I felt them pulling up against my body.”

“God, Riley,” I moaned. “So close now, ohmygod so close.”

“Holy fuck,” Hannah’s voice came from the speaker phone.

Riley sucked me harder, hands cradling my balls, fingertips pressing just behind them, and I lost my control. “Ohgod coming now Riley, oh fuck oh fuck,” I cried out, as my cock lengthened and thickened in her mouth. My climax slammed upon me, my come bursting out in spurts, filling Riley’s mouth. She swallowed to keep up with my load, and my cock pulsed with pleasure as I felt her lips and tongue moving against my shaft.

“Ohmygod, just listening to that was so fucking hot,” Hannah said over the speakerphone. “I’m already getting wet, you guys.”

Riley swallowed one final time and let my shiny cock slip from her lips, reaching for the phone. Before I handed it to her, I echoed what Riley had said a few minutes ago. “Hannah? Get your cute little ass over here.”


That first night with Hannah led to several other threesomes throughout the girls’ senior year. Hannah was a flexible, enthusiastic, and very orally-fixated lover. She loved eating Riley out, loved sucking my dick, and loved it when either of us went down on her. Although she and I had teased each other a few times in my condo, I didn’t really think I’d ever have a chance to see her naked, and so that first time in the hotel room was an amazing revelation, a memory that I still treasure.

Her body was lean and firm, a bit harder than Riley’s but still curvy. Her hair was brown and hung straight to her jawline, and she was about two inches shorter than Riley, with smaller breasts, muscular thighs, an amazingly tight ass, and a cute little bush trimmed into a neat, dark brown triangle. She was stripping her clothes off the moment the door closed behind her, proclaiming, “Ohgod, I need my pussy eaten!”

When Riley and I looked at each other, deciding who should do it, Hannah moved onto the bed, spreading her legs obscenely. “I don’t care -- either of you -- someone -- no wait, both of you! Yeah, both of you eat me!” she said, her fingers playing across her bush.

We looked at each other and shrugged, stupid smiles played across both of our faces. I’d never gone down on a woman in tandem before, and marveled that Riley was still leading me into new sexual experiences. So, our sides pressed together from shoulder to ass, Riley and I knelt on the floor between Hannah’s thighs and went to work, our tongues dancing over her inner thighs, then meeting as we licked across her slippery lips and clit.

It was an amazing, erotic feeling, almost as though Riley and I were making out with each other, and with Hannah’s pussy, at the same time. As we licked her together, making her clit stand out for attention, I felt my cock harden again, and Riley grabbed for it as we ate Hannah, stroking me. I moved one hand between Riley’s thighs, and played with her own slippery lips, as we continued to eat the brunette splayed out in front of us.

Hannah quickly shuddered and cursed through one orgasm, raising her hips off the bed and pushing them into our faces. She didn’t seem to want us to stop, so we kept going. As another climax approached, I left the job to Riley and moved behind her, running my fingers between the blonde’s thighs. Her own pussy was dripping wet, and she eagerly moved her thighs apart, anticipating my next move. As she knelt on the floor, eating her roommate, I knelt behind her, between Riley’s legs, and fisted my cock, pushing the tip against her wet pussy.

Riley moaned with pleasure into Hannah’s pussy as my cock head slipped between her own lower lips, and Hannah looked up from the bed to see what was going on. “Oh yeah, Mark,” she moaned. “Fuck Riley. Fuck her good, fuck her and drive her face right into my pussy.”

All three of us moaned as I pushed my cock into Riley, her wet tight channel surrounding my cock. She lowered her face back into Hannah’s lap and busily licked the brunette’s pussy, Hannah’s hands clutching at her own firm tits.

In and out, I stroked my cock deeper and deeper inside Riley, until my balls were resting against her firm, smooth ass. I pulled out most of the way, then pushed back in, out and in, repeating this cycle as both girls moaned with the sensations.

“God, so good,” Hannah moaned, tossing her head from side to side as Riley licked her. Hannah’s short brown hair was slick with sweat and stuck to the side of her neck, as her head lolled back and forth on the bed.

I moaned in agreement as my cock slid in and out of Riley, her tight pussy clutching at my cock with each stroke, my balls smacking against her perfect ass.

I’d already come once in Riley’s mouth, of course, and so she reached climax before I did this time, shrieking in pleasure as her pussy rippled around my cock. She paused her ministrations to Hannah’s pussy and I held still inside her, not wanting to move, knowing she’d be sensitive right after her orgasm.

We must have made quite a sight: me kneeling on the floor, thighs pressed against Riley’s ass, my cock still hard inside her. Hannah, spread-eagled on the bed, with Riley’s face pressed against her thigh, her pussy open and drooling. Hannah caught my eye and smiled at me, asking, “are you on the pill?”

I nodded, I’d been on male birth control for years.

Her eyes lit up. “Riley, can Mark come inside me? I love the feeling, and most dumbass college guys aren’t on the pill, so I have to use a condom.”

In a tired voice, Riley readily agreed, and we repositioned ourselves. Hannah liked being on top (“again, most college guys are dumb and don’t like it that way”), so I positioned myself on the bed on my back, my cock hard and slick and pointing to the sky. Hannah swung one leg over and straddled me, and I shivered with pleasure as Riley took my cock in her hand, aiming it towards Hannah’s slit.

I put my hands on Hannah’s waist, stroking her hips, and as I felt the tip of my cock touch her wet lips, I looked at Riley. “Is this OK?” I mouthed. I realized that in our previous threesomes with Caitlin, I hadn’t ever been inside anyone but Riley.

Riley nodded, her eyes gleaming with excitement. “Yes,” she whispered. “I want to see it.”

Riley caresses her roommate from behind as Hannah bounces on Mark’s cock, during their first threesome experience.Slowly, Hannah sank down on to me, my cock sliding inside her, Riley’s fingers caressing us both. All three of us moaned as my cock filled Hannah’s pussy. She was hot and wet and tight around me, different from Riley but still so good.

As Hannah settled into a rhythm moving up and down on my cock, Riley moved behind her, straddling my knees. I watched, fascinated, as she planted small kisses along Hannah’s shoulders and back, Riley’s fingers playing with Hannah’s breasts, rolling the nipples between her fingertips. Hannah threw her head back and moaned in pleasure as Riley pinched each of her nipples in turn.

I moved my thumb down to Hannah’s pubic mound and pushed it through her tuft of hair, playing it across her hard clit, and I felt her pussy get even hotter. Meanwhile, Riley briefly abandoned Hannah’s breasts and started rubbing all over her torso, touching her shoulders, her abdomen, her shoulders, her back. Our hands briefly touched as I stroked Hannah’s pelvic region, and Riley grinned at me.

As I thrust my hips off the bed to meet Hannah’s movements, I knew both of us were getting close, her pussy starting to erratically throb around my cock. I felt Riley’s fingers brush against my thighs as she clutched at Hannah’s ass from behind, and I saw Riley glance downward and smile, a devilish look on her beautiful face. Suddenly, I felt Hannah jump, the temperature in her pussy increase another few degrees, and she exclaimed, “Oh god Riley! Oh god you’re touching my asshole, that’s so hot and so nasty and so fucking hottttttttt...”

I slammed my cock into Hannah harder, grabbing her hips to help me gain leverage, and I felt her quivering with delight. “Oh god, Mark, I’m going to come, ohmygod you guys I’m going to come so hard...”

“Me too, Hannah, oh I’m about to blast off inside you with Riley watching...”

“Yes, Mark, oh yes give me your come I want it so badly, fucking come in me.”

I was teetering right on the edge of control when Riley chimed in, pushing me over the edge. “Give it to her Mark, give her your come, let your big hard cock explode inside her, you’re fucking my roommate, come inside my sexy little teammate.”

“Oh god,” I moaned, feeling the machinery of orgasm kick in, knowing that I was powerless to stop it. “I’m coming!” I cried out, my cock flexing and spasming inside Hannah’s tight passage, my come blasting out inside her.

“Oh god he’s coming oh god it’s so hot it’s in me so hot oh my goddddddd,” Hannah wailed as her own orgasm overtook her, her pussy throbbing around my dick, her own lubrication splashing across my cock and balls, as Riley rubbed her back and kissed her neck, whispering into her ear.

The three of us didn’t get much sleep that night, nor during any of our other nights together throughout that school year. Most of the time, we got together when I rented a hotel room in Amherst. But a couple of times, we used either Riley or Hannah’s dorm room, the three of us making some very interesting arrangements on one of their tiny beds!! Or, when we needed more space than a twin mattress could provide, we pulled the blankets off the bed and coupled (or tripled!) on the floor.


Throughout the fall season, the soccer team played amazingly well. They were led by a great senior class (anchored by Riley, Hannah, Missy and Parker) who knew this was their last chance to win a national title.

The team stormed through the regular season, losing only three games, and tying once. Riley was a scoring machine, averaging nearly a goal per game, and Hannah had her best season as a college athlete as well. They were the number one seed heading into the NCAA “College Cup” tournament, held in Philadelphia that year. The games would be played over two weekends; the early rounds the weekend of Thanksgiving, and the semifinals and final the following weekend. The UMass team was hoping to be playing both weekends in Philadelphia, and I promised Riley I’d be there for both.

Since the games were in her hometown of Philadelphia, Hannah was planning to spend a couple nights of the holiday with her parents, and she got their coach’s permission for Riley to come along as well. The girls encouraged me to come with them, and after making sure it was okay with Hannah’s family, I agreed.

“I’ll move to a hotel room after Thursday night,” I told Hannah and Riley. “You all will be at the team hotel, and so there’s no need to stay at Hannah’s parents’ house by myself.” I looked at Riley. “Do you think your coach will let me take you out to dinner on Friday, for your birthday?”

Riley frowned. “Maybe, if our game is late in the day Saturday.”

“I’ll help convince him,” Hannah piped up. “Maybe Coach will even let you stay over with Mark on Friday night, since it’s your birthday and all.”

“Maybe,” Riley said, though she didn’t sound convinced. When she wasn’t looking, I glanced at Hannah and winked; she knew exactly why I wanted Riley to spend the night with me on the 27th.


Early in the fall, I started thinking about mine and Riley’s future together. As her parents had correctly predicted, Riley was planning to find a job in Boston after graduation and move in with me permanently. I was definitely all for that -- but I wondered if we should make things even more official once she graduated.

So, I started looking at wedding rings. I confided in Hannah, Jennifer, and Caitlin, and they helped me shop for a ring and also plan out how and when to propose to Riley.

One day in early November, while Riley was at a study session, I was sitting in her dorm room with Hannah, the two of us video-chatting with Caitlin and Jen. I’d showed them the silver ring I’d purchased, with a three-quarter-karat diamond in a marquis cut, and the three of them oohed and ahhed appropriately. Then, we started talking about when to propose.

“Obviously, Valentine’s Day is no good,” Jennifer said, “since that’s the day Tom proposed to her.”

“Right,” Hannah said. “But, on the other hand, it’s the day she ran to Mark and their relationship became permanent. So maybe it is a good day?”

“I shook my head. “No. I mean, we’ll always celebrate Valentine’s Day of course, but I don’t want to propose on that day. I’m thinking more about on her birthday.”

The three of us planned and schemed for the best way to get some alone time with Riley on her birthday. “Coach will let her spend one night with you that weekend,” Hannah assured me. “We won’t play until the afternoon on Saturday -- we’ll have a high seed and a first round bye -- so it will be no problem.”

 
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