Chapter 10: Friends and Temptations

May, 2021 (a little over four months later)

“Oh my god, yes,” the blonde shouted. “Harder Mark, fuck me harder!”

I looked down at her tight ass as my cock slipped in and out between her thighs. She was on her hands and knees at the foot of my bed, and I stood behind her, slamming my cock in and out. She tossed her head from side to side in passion, one hand grasping at her swinging breasts.

“Ooohyeah, almost there,” she moaned, and I felt her pussy rippling around my cock. I pushed into her harder, feeling her orgasm overtake her, and then gave a few short strokes, triggering my own climax. I poured my semen into the condom, aftershocks rippling through my body, slowing my thrusts, eventually bringing my hips to a halt.

I eased my cock out of her pussy, and she let herself fall to my bed, face buried in the pillow. “That was so good, Mark,” she moaned. I pulled the slimy condom from my cock and let it fall to the carpet, climbing into bed next to her.

“Is your alarm set for 6?” she asked me sleepily. “I’ve got a meeting first thing tomorrow, and have to run back to my place to change first.” I told her it was, and she quickly drifted off to sleep.

I’d been casually dating Michelle for about three months. Our first date was a couple of weeks after I worked up the courage to introduce myself to her at the gym. She was a lawyer at a financial services firm in Boston, about 5 years older than me (though she certainly didn’t look her age, thanks to a fanatical workout routine).

The first three times we’d gone out, we’d refrained from any physical intimacy. On our fourth date, we made out a bit in my car when I dropped her off at home, her hands roaming freely over my crotch. On our fifth date, she invited me to spend the night, and we’d been getting together a couple of times a week since.

Sometimes we went out, to dinner or a move, or to a bar. Other nights, we spent the night at one of our apartments and ate pizza or leftovers, before retiring to the bedroom.

I’d wisely moved Riley’s pictures off my nightstand before having Michelle spend the night at my place the first time, though she did ask about the picture on my fridge. The “niece” excuse seemed to satisfy her.

As I laid there in the dark, my cock sticky and soft against my thigh, I wondered if tomorrow would finally be the “morning after” where I’d break up with Michelle. We didn’t have much in common -- she was much more politically conservative than I was, for one thing, which had led to a few nasty arguments. But we also wanted different things out of life -- she was looking to get promoted, make lots of money, live in a fancy house and buy a boat to take up to the Vineyard every summer.

When I asked her once about kids, she remarked that she’d never get her body back into shape if she got pregnant, and the discussion ended right there.

The sex was regular, and it was certainly better than no sex at all. But she was fairly unremarkable in the sack; we only ever did it missionary or doggy style, and my cock had never touched her lips. Even though I was still on birth control, she wasn’t (“the hormones fuck up my weight,” she said), and she insisted that I wear a condom every time we fucked. I hadn’t worn one of those things in years, and I hated ‘em.

One thing we both loved was me going down on her -- she got a Brazilian wax on a regular basis, and it was very enjoyable to eat her smooth, silky pussy until she came all over my face. A few times, I’d lick her while stroking myself, timing it so we’d come at the same time.

So, although I enjoyed the sex, and most times I enjoyed her company, I knew there was no future in our relationship. Better to break it off sooner rather than later, even if it hurts her feelings, I told myself. It wasn’t her fault; it’s just that we weren’t all that compatible.

Deep down, in a part of my brain that I tried to suppress as much as possible, I knew that the simplest explanation was probably also the correct one: she wasn’t Riley.

Over the late winter and into the spring of that year, Riley and I kept in touch. But things had definitely cooled a little bit; our frequency of calls, texts, and video chats slacked off from the previous six months. Still, she surprised me with random texts throughout the day on a fairly regular basis. I sent her a small teddy bear and a card on Valentine’s Day, and she texted me a picture of the bear, saying, “i love him -- and i love you!”

I did tell her when Michelle and I started going out, and when she asked a few weeks later if I’d fucked her yet, I sheepishly admitted that I had, just the night before. Not jealous at all, she clapped her hands together, then stripped off her pants and underwear and demanded that I tell her all about it while we played with ourselves. Hesitant at first, I quickly got into it when I realized how excited Riley was getting. “I wish I could have been watching your cock slip in and out of her,” she said, shuddering in her chair, and I realized that she had a voyeuristic streak to go along with her exhibitionist tendencies!!

She did admit to me, in late February, that she and Trevor had “gone all the way” for the first time. Unlike her, I didn’t want the details, but I felt I at least had to ask how it was.

She blushed, and admitted, “Not great. He came in about a minute, and of course I didn’t.” I chuckled, and she glared at me. “Sorry,” I said, holding up my hands. “I was a teenage boy once too, I know what it’s like. He’ll get better.”

She nodded. “I know. And he is very sweet, wanted to make sure I was OK with everything. I think he’ll be ... teachable,” she said, laughing.

On Friday night, a few days after our final lovemaking session, I worked up the courage to tell Michelle I didn’t think we should date anymore, over dessert at a local bistro.

She was pretty pissed off, and asked me repeatedly, “Why? Are you screwing someone else?” as half the restaurant turned to look at us.

“No,” I said honestly. “I just don’t see any future for us. We want different things.”

She shook her head, standing from the table. “You’re a damn fool, Mark. You don’t know what you’re throwing away here, and you’ll never do any better than me.”

Despite being pretty sure I’d done the smart thing, I was depressed when I got home. My inner voice wondered, Was Michelle right? Am I throwing away the best relationship I could ever have? Is this all because I can’t get over Riley?

Grabbing a beer out of the fridge, I slumped down on my couch and set my iPad on my lap, sending Riley a FaceTime request. I had to talk to her, had to see her.

The screen blurred into focus and there was Riley’s smiling face. “Hi Uncle Mark,” she said. I could see she was wearing the pink PJs I’d given her for Christmas last year. Behind her, three other girls squealed and moved quickly out of the frame.

“Riley, we’re not dressed,” one of them protested.

“Seriously, you can’t just turn on a camera and let a guy see us,” another voice said.

“They’re right, Riley, but your uncle is kind of cute,” a third voice added.

Riley laughed, and looked at me. “Sorry about this, it’s a sleepover.” She winked at me, and flipped the camera around to face the other girls again. “You can tell him yourself. Uncle Mark, say hi to Jessie, Samantha, and Taylor.”

“Rileyyyyyyyy,” they shrieked in unison, again trying to move out of the frame. I caught brief glimpses of smooth, teenage thighs disappearing beneath nightgowns and nightshirts as they shuffled offscreen. “Hi girls,” I said brightly.

Riley laughed again. “OK, sorry you guys. I’ll be right back.” She flipped the lens back around, and I could tell she was walking out of her bedroom, closing the door behind her.

“So,” she said, still laughing. “How are you? It’s nice to see you,” she said, slumping down to a seated position in the hallway outside her bedroom.

“OK,” I answered automatically. “Well, I mean, kind of. I broke up with Michelle tonight.”

Riley’s eyes instantly clouded over with concern. “Oh, Mark. Oh, I’m so sorry. Why? I mean I guess I know why -- same reason you told me last week?”

I nodded. “Yeah. We just weren’t right for each other.”

She smiled at me, sadly. “I know. You knew it wasn’t permanent from the beginning. But you had to hang around long enough to find out how she was in bed, right?”

I laughed. “Definitely, and we had a pretty good time in bed.”

“Good,” Riley said. She lowered her voice and continued, “Maybe you learned some new things to show me, some day.”

I blushed, thinking of Michelle’s smooth, bare pussy. “Maybe!”

“Seriously, though, Mark -- are you going to be OK? Do you need me? I can stay on the phone with you for as long as you want.”

“No, Riley, I don’t want to keep you from your friends. I just wanted to see you for a minute. You have girl sleepover stuff to do, like strip each other down and have tickle fights or something.”

She laughed. “Wouldn’t you like to stay on FaceTime for that?!?”

I readily agreed, and we laughed together. “Really,” she said quietly, “it’s funny you called right now. We were just talking about sex, and I admitted that I lost my virginity on the cruise last summer. The three of them assume it was to a boy my own age. I also told them about Trevor.”

I nodded, getting excited as I imagined teenage girls discussing sex. “Are the others -- have they had sex?”

Riley smiled. “You dirty old man!” she said. “Jessie definitely has -- she’s had the same boyfriend since 8th grade. Pretty sure Samantha and Taylor are virgins, though I know Sam has at least given her boyfriend a blowjob. We’ll probably talk about it tonight.”

“Wow,” I said. “I wish I were there!”

She looked at me tenderly. “I do, too. You’ve had a rough night.” She paused for a moment, looking back at her bedroom door. “Hey? Can I call you back from my iPad in like 5 minutes? Maybe the girls and I can do something to cheer you up.”

I agreed, and with a quick exchange of “I love yous,” we disconnected the call.

Five minutes later, she called me back, and when the video focused, I saw Riley backing away from the camera. The other three girls were lined up along the edge of her bed, two of them shifting nervously from one foot to another.

“Uncle Mark, I told the girls you broke up with Michelle tonight, and we all feel bad. So we want to do something to cheer you up.” Riley joined the other three next to her bed, and they turned around, facing away from the camera. Three of them were wearing nightshirts or nightgowns, Riley was in those short pink PJs, and my eyes greedily drank in the sight of their smooth legs and tight little butts.

“Ready girls?” she asked. “1... 2... 3!!!”

As they got to “3,” the other girls flipped up their top garment, briefly exposing their underwear to me. I caught sight of a pair of blue panties, a high cut pair of pink ones, and a shimmery white pair of boyshorts. However, my attention was quickly diverted to Riley, standing on the far right. She’d hooked her thumbs into both her shorts and panties, and lowered them together, flashing me a couple-second glimpse of her smooth, pale ass, and that inviting gap between her thighs. My cock swelled to full hardness quickly, and I reached down to adjust myself.

Her three friends let their nightgowns drop back into position, and Riley quickly pulled her shorts and panties up. “Riley,” one of the other girls said, noticing her motion. “You can’t show your uncle your naked butt!”

“Well, I just did,” she said, unapologetically. “He’s had a rough night.”

“And you think your bare ass can fix everything?” a second girl said, as they all laughed. Riley walked back over to the iPad, winking at me when she neared the camera.

“Well, Uncle Mark?” she asked. “Did our butts cheer you up?”

“Oh, definitely,” I said.

“Ask him if he got hard,” someone said from the background, as the other two girls giggled and pretended to scold her.

I looked at Riley for a second, her face close to the camera, blocking out the view of the others, and I mouthed “thank you” to her, then blew her a kiss.

“Oh, definitely,” I repeated again, loud enough for the other girls to hear. They giggled some more, while Riley blew me a kiss and mouthed “I love you. Goodnight,” before we closed the connection.

Later, when I got into bed, I opened my nightstand drawer and pulled out the two pictures of Riley and I that I’d hidden away. I stared at them for a while -- the formal night picture and the one of her kissing my cheek the last morning. Finally, I propped them back up on my night stand, angling them so I could see them from my pillow, and drifted off to sleep.

Well, not immediately to sleep. I must admit, I took myself in hand and stroked myself to orgasm, thinking about three panty-covered rear ends, and one pair of pale, bare cheeks.

As Riley’s sophomore year drew to a close, we continued to keep in touch on an occasional basis. She still liked to surprise me with text messages at random times, and her digital notes were always a bright spot in my day.

She broke up with Trevor two days before school ended; when I asked why, she told me “I don’t really want to talk about it.”

A few days later, I got a phone call from Jennifer, who explained that Trevor had been seen making out with another girl at the movie theater, and word got back to Riley. “Poor thing,” I said. “She must be heartbroken.”

“She’s not really,” Jennifer told me. “She was pissed, and rightly so, at him for cheating on her. But she was aware that Trevor was a short term boyfriend, and nothing more.”

“Oh,” I said. We were quiet for a couple of minutes, and then I brought up something I’d been thinking about. “Jen, I know you guys are going to Europe next week. The day before you leave -- June 11 -- happens to be the one year anniversary of, um ... well, of mine and Riley’s first time. Our Arrangement.”

“Oh, I know, Mark. And Riley knows too. She was wondering if you remembered.”

“I’ll never forget that day as long as I live,” I told her honestly. “So I was thinking of sending her a little something -- maybe a pendant, or a pair of earrings -- to mark the occasion. Do you think that would be OK?”

I could hear the smile in Jennifer’s voice. “Mark, that would be more than OK -- it would be wonderful, and it would mean a lot to Riley.”

I smiled. “Okay, thanks. I’ll pick something sentimental but appropriate, and make sure it gets to her before you guys leave. Have a wonderful time!”

In the end, I purchased Riley a small gold heart-shaped pendant with a script “R” engraved on the front, on an elegant chain that would look lovely on her neck. I wanted to have “6-11-20” engraved on the back, but I was worried a friend would see it, and then how would she explain the significance of the date? So in the end, I decided not to include the date. I knew it would be meaningful to Riley either way; and, now she could pass it off as a gift from her very friendly uncle if she needed to, without it seeming weird.

On the morning of the 11th, I was at work when she texted me. She and I had already made plans to FaceTime that night, in advance of her family’s departure. The text simply read:

“June 11. What a good day.”

I smiled, my cheeks reddening as I thought back to that day. We texted back and forth for a little bit, then the workday pulled my attention away.

Mid-afternoon, I was back at my desk when my cell phone rang with Riley’s ringtone. When I answered it, she was giggling and talking and sobbing into my ear, all at once.

“Thank you thank you ohmygod you are so sweet and I can’t believe it and this is so beautiful and I love you and I miss you and I wish you were coming with us.”

We chatted for a couple of minutes, and then agreed to talk more on video chat that evening.

That night, she showed me the pendant, making exaggerated motions to pull her neckline away from her body. I got a good look at the pendant and an even nicer view down her shirt.

“Rileyyyyyy,” I warned her.

She let her collar snap back into position. “I know, I know,” she pouted. “But I miss you so much!”

“I miss you too, sweetie. But I know you guys are going to have a great time in France and Spain and Italy, and I can’t wait to hear all about it!”

I got a little glimpse into their trip to Europe from pictures Riley posted to Instagram and Twitter. Seemed like they had a great time, dividing their visit equally between tourism and relaxation.

A few days after we got back, we finally had a chance to FaceTime. We made small talk for a couple of minutes, but Riley’s face was tight with nervous anticipation, and I could tell there was something she was dying to tell me.

Finally she couldn’t wait any longer, and she blurted it out. “I went to a topless beach, Mark!”

I smiled, Riley’s exhibitionist tendencies finally getting a way to manifest themselves. “How was it, Riles?”

She excitedly told me about the experience -- she and her parents had made friends with another American family in the south of France, staying at their same hotel. The other family had a daughter Riley’s age, and another daughter a couple of years older. The three of them had asked their parents for permission to go down to the local topless beach, and the parents had agreed.

“It felt so wrong -- but so awesome -- to be walking down the beach in nothing but my bottoms,” Riley said, her eyes glittering as she told me the story. “My nipples were hard as soon as I took my top off, I was so excited.” I pictured Riley strolling down a public beach with her beautiful 16-year-old breasts on display, and reached down surreptitiously to adjust my growing cock.

“We hung out for a couple of hours that first day, and then a little bit longer the next day,” she told me. “On that second day, these French guys came over and starting talking to us, and one of them -- Pierre -- was talking mostly to me.”

“Uh huh,” I said, chuckling. “I bet I know where his eyes were staring, too!”

She giggled and blushed. “He was looking at my boobs, for sure. The guys were all wearing those little Speedo bathing suits, so we were looking a bit too, you know?”

I nodded. Despite an undercurrent of jealousy hearing about another guy, her story was turning me on, and my hand dropped to my crotch again.

This time, Riley noticed my arm movement. “Ohmygod Mark, are you touching yourself? Is this turning you on?”

I nodded. “Of course it is -- don’t stop now!”

She laughed. “Ok. So Pierre asked me if I wanted to come back to his apartment, but I promised my parents I would stay on the public beach with Rachel and Stephanie.”

“His apartment? How old was this guy?” I asked, the words sounding ridiculous as soon as they came out of my mouth.

“Maybe like 21, 22? He’s in college,” Riley said. “So anyway, when I told him I had to stay on the beach, we were both kind of bummed. But then he said there was a more private part, further up from the water, where we could go. It was sort of up behind this stand of palm trees, kind of in sight of the others but not right with them.”

Riley told me the two of them had moved over there, and Pierre had starting stroking her arm, and they kissed a little bit, his hands moving over her nipples. “He told me my boobs were nicer than my friends’,” she said, giggling.

“His hands felt so good on me,” she said. “He was like you, so gentle and slow, and not like Trevor, who always acted like he was in a hurry and needed to rush things.”

I nodded, stroking my cock through my shorts.

“He asked me again if I could go back to his apartment, but I really couldn’t,” she continued. “He bent over and started kissing my nipples, and I was looking down at his bathing suit. I could tell that his dick was getting -- getting really hard, the tip of it was starting to poke up from the speedo, so I put my hand on it and started rubbing it.”

“Oh god, Riley, this is hot,” I said, pulling my shorts off and stroking my cock in earnest.

“I know,” she said, sliding around in her chair, pulling her panties out from under her nightshirt and showing them to me.

We stroked ourselves as she continued her story, telling me that Pierre had played with and sucked her nipples while she stroked him through his speedo. “A few minutes later, he started pressing against the front of my bikini bottoms,” she said.

“He moved his fingers in circles on the front of my bikini, pressing against ... pressing against my clit. When he slipped a finger inside my bikini and started touching me ... directly,” she said, blushing, her arm moving faster, “I knew I was going to come, right there on a blanket on the beach. It was so hot, Mark, being kind of exposed in public. No one seemed to be paying attention to us, but they might have been. I wouldn’t have known.”

I stroked my cock as she went on with the story, telling me that she came all over his fingers, and then reached inside his speedo and stroked his cock. “He was ... big, Mark,” she said, blushing. “And he wasn’t ... circumcised, like you are and like Trevor is. He licked my nipples and I stroked him. I wanted to make him come, but he said it was too public and he couldn’t take his cock all the way out, couldn’t make a mess right there on the beach.”

“He told me he wanted to fuck me, and said again we could go back to his place. I told him my parents would kill me, but then I had another thought -- maybe we could go back to our hotel room? I figured if I told my parents where we were going, maybe they would be OK with it?”

“Wowwww,” I breathed.

“I know,” she said. “So I put my top back on and he slipped on his shirt, pulling it down so it covered his boner, at least mostly. We told Rachel and Steph we were going back to the hotel, and I went and found mom and dad by the pool. I introduced Pierre to them and pulled my mom aside, asking if I could take him back up to the room.”

“What did she say?” I asked.

“She didn’t say anything at first, just looked at me. I think she could tell I’d been fooling around with him already, and she asked me if I’d stayed on the public beach the whole time. I told her I had, that I told Pierre I couldn’t go back to his apartment, so I brought him here instead. I think she was impressed, and after she whispered something to my dad, she said we could go upstairs. As we started to walk into the hotel, she grabbed me and whispered ‘make sure he uses a condom, ‘ and that was it.”

“Wow,” I repeated. “Your folks are amazing, Riley.”

“I know,” she agreed. “So Pierre and I went upstairs, and we had each other’s clothes off within a minute. Mark, ohmygod his dick was so big when I finally saw it, I wasn’t sure if it would fit in me.”

“I licked him and sucked him for a bit, and then I asked him if we could ... if we could go out on the balcony.”

I smiled. “You sure like outside sex,” I said, thinking of our own balcony adventure on the Marvel.

“I know, Mark. He wasn’t as good as you -- and I don’t love him -- but ohmygod it was the middle of the afternoon and the balcony looked over the beach. We were on like the 10th floor, so it wasn’t easy for anyone to see us, but I leaned on the railing and he fucked me from behind, and I looked out over all those people.”

“His dick was so big, it kind of hurt at first, but then it started to feel good and he reached around and played with my clit while he fucked me. His balls were so heavy and they were slapping against me the whole time.”

“I came within like two minutes, feeling that warm sun on my naked skin and that cock inside me, and then he came inside the condom. I didn’t like that part as much, I couldn’t feel it in me. But the outside fucking was so exciting, I’m sure at least some people in the hotel heard me shrieking when I came.

“Oh god,” I moaned, thinking of how loud Riley could be when she climaxed. I felt my cock swelling. “I’m going to come too, Riley.”

“Me too, Mark,” she said. “I want to be outside with you some day, touching you, having you touch me, lick me, eat me, fuck meeeeee...” she wailed as her orgasm crashed over her. Watching her face contort in passion sent me over the edge, and my cock exploded, come spurting over my pelvis and stomach.

“Goddddd,” I breathed. “You are so fucking hot, Riley,” I marveled.

After we both cleaned up, we chatted about the experience a bit more, her only such encounter while in Europe. “Are you jealous, Mark?” she asked me softly.

“No. Well, maybe. A little,” I admitted. “But I love that we can share these kind of things with each other, and I’m glad you had a chance to have some fun. I just want you to be happy, and safe.”

She nodded. “I love you, Mark, and I can’t wait to see you again.”

“I love you too, Riley.” We talked about when we might be able to visit again, but nothing immediate came to mind. She had a busy summer planned, and soccer and school would start again in August. This December, I was supposed to go to California to visit my parents and my sister, so a repeat winter break trip was likely out of the question.

We chatted for a few more minutes, finding no immediate solution, and eventually said our goodnights.

Through July and August we kept in touch, trailing off a little bit as Riley got busy with soccer practice at the end of August. She made varsity again of course, and expected to be a full-time starter this year. She started dating someone from the guys’ soccer team, and things seemed to be going fairly well.

Her parents kept their promise to buy her a car -- they got her a 5-year-old Corolla, and she gave me a FaceTime tour in her driveway, excitedly showing me all the features. The perverse part of my mind noted the relatively small back seat, and I was grateful her parents hadn’t purchased her a giant SUV!

I shared my exciting news with her -- I’d been promoted at work to a project manager, replacing an employee that had moved away. The promotion meant I moved out of a cubicle and into my own office, with a door and a window, even. Sure, the window just looked out into the alley between us and the building next door, but it was better than nothing.

The new job came with a nice salary increase as well, and I started looking around at condos for purchase, maybe something on the red or green MBTA line, to give myself an easier commute.

But, the most exciting part of the new job, and the part that was directly related to Riley, didn’t come up until late September. My boss knocked on my open office door, and when I waved him in, he stepped inside and closed the door behind him.

“Hey Mark -- how are things?” We chatted for a few minutes, about personal life stuff and the new job, which I’d been doing for about three weeks at that point.

“We usually send our new project managers to the ASCE management seminar,” Bob said. “It’s three days, gives you a chance to learn some management techniques, meet some other people in similar positions, etc., etc. We get a discount for being ASCE-affiliated, and it’s always worked out pretty well for us in the past. Are you interested?”

“Sure, Bob, thanks. That sounds great.”

“Good deal. The next one is coming up at the beginning of November, it’s three days, like a Wednesday-Thursday-Friday. You can extend through the weekend if you want to.”

“Cool, I might. Where is it?”

Bob glanced at his paperwork. “Oh, this is nice -- gets you away from our November weather, and someplace warm.”

“The conference is in Orlando, Florida.”

I didn’t hear much of what Bob said after that, because my conscious brain was repeating the same word, over and over again.

Riley.

Riley lived in Orlando -- I could see her on this trip, just two months from now! A dim part in the back of my brain reminded me what her parents had told me on the cruise -- that the age of consent in Florida was 18, so anything sexual would be illegal.

Still, even without the sex, it would be so great to see her.

I looked up details of the conference online. As Bob had said, it started on Wednesday, concluded on Friday. It was at a conference hotel down near the theme park area, south of Orlando proper. I knew Riley and her family lived in the northern suburbs, and I pulled up Google Maps to see how far away I’d be.

I texted Riley when I got home, asking her to FaceTime me when she could. When my iPad rang about an hour later, I grabbed it and answered it.

“Guess what?” I said, before even saying hi to her. “I’m coming to a work conference in Orlando in November!”

Riley squealed with excitement, dropping her iPad as she clapped her hands. She picked it back up, laughing, and I gave her the details of my trip as I knew them so far.

Of course, it was a school week for Riley, and I had conference obligations all day, so our time together might be limited.

“So let’s see,” I said. “Wednesday night, there’s a dinner and reception that I probably have to go to. But Thursday and Friday nights are open, and I can stay for some or all of Saturday.”