AMA - The Boyfriend Ch. 091-100

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All characters are 18 years or older.

This story is a continuation of the AMA: The Boyfriend series. I would highly suggest starting with Chapter 1 if you have not already. This collection of short chapters was originally published on a daily basis, and are collected here for Literotica. In these chapters you can expect more App exploration, a sexy photoshoot, MFF oral, cute and flirty conversations, kisses and cuddles,.

The AMA was originally conceived of by Fantasy; this is just my version of the popular idea. Kudos to him and his original versions!

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Chapter 91

We went back in front of the mirror and I began working with Cassidy's hair again as she used her phone. Since I couldn't actually see anything - it looked to me like she was scrolling Instagram this time - there was no point in me just sitting there. So as I carefully worked my way along her scalp, Cassidy narrated to me what she was doing.

"Alright, so that's all the Perks I bought you turned back on," she said.

"Just for my own sake, could you tell me exactly what the lucky one is?" I asked. "I just don't want to get bitten on the ass by it at work or something."

"Um, OK," she said. "It's called 'Lucky In Love.' It says that any time you are included in a randomized event, such as a game of chance, you'll never be the big loser and if it could lead to a positive relationship encounter you are considered the House. And the House always wins."

I blew out a breath and nodded. So it wasn't just a 'win all the games' sort of thing. I wasn't about to lose big on anything, at least not in the long term, but I wasn't going to be some statistical anomaly that would get the attention of my bosses at the Casino either. That was the last thing I needed - someone back in Vegas deciding I was a cheat. I'd never work again.

"OK. I mean, it sounds great, and obviously it worked last night," I said. "What about the last one?"

Cass hesitated for a moment. "Are you asking me to tell you what it is?"

I knew she'd been having a little bit of fun amongst all this by letting me 'discover' them as we went along, but I was starting to get a little tired of questioning what was going on. "Hon, last night was an eye-opener for me. Apparently, even without the App I still kiss really well. And everyone we've been... intimate with in one way or another didn't seem surprised like anything had changed. Terra was still flirting and kissing me. Same with Wanda. Cattie didn't even seem to think there was a difference."

"Tiger, that's because I only picked things that made you more of who you are. I tried to tell you that," Cassidy said. "Look, we've been together a long time, right? Well, that means that you and I have been practising our kissing, and sexual stuff, together for a long time. We've been completely comfortable with each other with that stuff for years and years. There are a lot of people, even in long-term relationships, whoaren't like that. Plus, not to bring up the elephant in the room, but I also had a lot of experience with learning how to kiss other girls. I definitely picked up and passed along some things to you, especially in that first year. I wasn't trying to do that, but I can only assume I did. The Kissing perk just enhances that a little bit and makes them remember it more vividly. If someone sucked at kissing maybe it would do more work, but you don't. Same with everything else you do."

"So what you're saying is that we've practised sex together so much that I'm just that good?" I asked, a little deadpan.

"Tiger, you're a fucking Stud," Cassidy said, looking at me in the mirror.

I wiped at my face for a moment, trying not to let it go to my head. Cassidy had always said things like that to me, especially during and after sex. I'd always taken the compliments, but assumed it was just couple talk. Maybe it turned out it wasn'tjust couple talk.

"OK," I nodded. "But yes, I do want to know what the last perk is, please."

"OK," she agreed, then scrolled for a moment on her phone. "The last one is called 'Satisfaction Guaranteed.' It ups your stamina based on the number of partners you're having sex with so that you can guarantee all of your partners get the attention they want. So if it's just you and me, or you and Cattie, it probably isn't doing much. But if everyone on the boat got in our bed at the same time, then you'd be the last person to tap out at the end of a long night."

I snorted a little, smirking at the idea of me just running a personal reverse gangbang on six women and being fresh as a daisy afterwards. "That one sounds ridiculous," I said.

"Only because you don't think it could happen," Cassidy pointed out. "But I didn't want the opportunity to come up for you and you pop a couple of times and then are tired out."

I hugged her from behind, then went back to doing her hair. "Cass, you're crazy but I love you."

"That's because I'm crazy in love with you," she smiled back at me.

"What's the App say about us?" I asked her.

"I- I haven't looked since the last time you asked me," Cassidy said, giving me a worried look. Last time I'd been all sorts of question marks instead of numbers for my stats. Having seen the App in action, and learned more about it, I couldn't help but realise more and more how utterly upsetting that would have been. It would have been like... well, like I'd been lying about an affair for years or something.

"Check," I nodded to her. "Please."

"OK," she said quietly, and tapped on her phone a few times. "Oh," she said. Then I was scrambling to catch her as her legs gave out from under her and she was crying, sobbing into her arms as she covered her face.

"Cass," I said. "Cass. What's wrong?"

"Nothing!" she sobbed, and she moved her arms and I could see her face and she was ugly-happy crying. "Nothing's wrong, Robbie. It- It- You love me. Y-y-you love m-me!"

I bundled her up in my arms and picked her up, sitting back on the bed again. It hurt, right down in my heart, that she needed to see it on the App to really know it. That my words weren't enough. But she also had relied on it, like a drug or a tool you took for granted, for so long that I could intellectually understand the why.

"Of course I do," I whispered to her, holding her close.

It took several long, wavering breaths for her to start getting herself together. Finally, she smiled at me weakly. "I guess it's a good thing I didn't do my makeup first, huh?"

I chuckled, imagining what sort of damage that tearful outburst would have caused to carefully applied makeup. I wiped the tears from her cheeks and nodded. "Probably," I chuckled softly.

"Do you want to know anything else?" she asked me, bending down and grabbing her phone from the ground from where she'd dropped it. She looked at the screen again and hugged it to her chest for a moment, savouring the sight of whatever more scores on the App said.

"Maybe later," I told her, helping her stand up fully again. "We're going to need to get out there sooner than later, and I still need you all dolled up, Mary Jane."

"I'll make sure I'm picture perfect just for you, Tiger," she grinned at me.

Chapter 92

Cassidy was pretty without makeup. Sure, her eyes were naturally a little squinty and her lashes weren't the thickest, and she had soft freckle blemishes, but she was still pretty. Especially to me.

But with full pin-up makeup?

Va-va-voom.

Thankfully JC seemed to have gotten his shit together enough after he'd fallen asleep at the end of the game last night that he had gotten the boat back in position near the beach. Soon enough we had the outside lights on the boats blazing, lighting up the waters of Lake Powell around us, and I was stripped down to my shorts and helping the girls go from ship to shore.

Cass was one of the first I brought across, followed by our camera bag. Then I was helping Heels, who said good morning to me but I noticed was eyeing me a bit. I tried to play off the fact that she likely knew without a doubt that Cassidy and I had had sex with Cattie the night before. Terra wished me a good morning, giving me a peck on the cheek, but JC was around to help her.

Wanda was the next out of our boat, and she waved me inside when she saw me from the living area. I climbed up out of the water and gave my legs a swipe with a towel so I wasn't tracking water inside, then went to her.

"Morning, stud," she said with a grin, opening her arms and pulling me into a hug.

"Good morning, gorgeous," I replied, and soon we were locking lips as she planted a massive kiss on me. My hands went down to her waist, then one onto her ass, and she hummed happily against my lips.

"What's on the schedule today?" I asked her once we broke apart. She was dressed in a t-shirt and bikini bottoms and holding a bag of her equipment.

"Micro bikini," she said. "Want to see?"

She knew as well as I did that there was no way in hell I was going to say no, but I still answered. "I would love to."

"I'll give you a private show later on one condition," she said.

"What's that?"

She leaned close, lowering her voice. "I want to hear about what happened in your room last night."

"Wanda," I sighed. "I don't know if I'm comfortable with kiss-and-tell."

"What if, and I'm just spitballing here, you tell me the story while I'm laying on your bed, fingering myself?" she asked. "Just an idea."

I groaned softly, imagining what that would be like. "Let me think about it."

"OK, Tiger," she grinned, then gave me another quick kiss.

Since Wanda was in a bikini she made her own way to shore but asked if I would carry her gear bag over my head which I happily did. She met up with Cassidy on shore and I left them talking. I had a feeling that 'idea' of hers wasn't exactly too far-fetched.

Back on the boat, I realised that the only people left on board were going to be Cattie and Heather. Part of me wanted to avoid them - well, not Cattie, but them as a couple. No matter what Cattie was saying about it, Ihad just fucked her last night and Heather had probably heard it. The more I brewed on that, the worse I felt about it.

Sure, Heather had pushed us into that circumstance, but it still felt... Well, it felt fucking cruel.

So I took a moment to steel myself, took a deep breath, and headed back towards the rooms. It was quiet, even at their door, and I realized I hadn't heard shouting. I also hadn't heard any crying.

I softly knocked on the door. "Heather. Cattie," I said as soft-but-loud as I could. "Everyone else is on shore now. If you need any help this morning, I'm about to go check with the other boat."

The door burst open just enough for light from the hallway to spill in a small slit and show me a pale line and one eye of Cattie's face. "We're not working this morning," Cattie said quietly. "Thanks though, Robbie."

"OK," I said. "Just, uh, shout if you need anything."

"Will do," she nodded.

I hesitated, but then mouthed slowly,'Are you OK?'

Cattie quickly nodded and mouthed,Thank you. Then she shut the door.

I tried not to make any guesses about what was happening in there. It wasn't my relationship, I had to keep telling myself. It was easier to convince myself of that knowing that Cassidy would probably be able to find out more than I would throughout the day.

Outside, I noticed that Becca had squeezed the Single's Boat a little closer to the beach, shortening the distance and that JC was already helping women across.

"No Cattie or Heather?" he asked as I waded over.

"Nope, not this morning," I said.

"Cool," he nodded. I had a feeling Terra hadn't filled him in on the end of the night yet.

Ami was waiting for me over on the Single's Boat deck. She was dressed in a simple pair of cotton shorts and a sweater, but had a big storage bin with her. She smiled widely when she saw I was coming to help.

"Morning, beautiful," I said. "Want a ride on my shoulders?"

"Sure," she grinned, and soon she was sitting on my shoulders, just her ankles and feet in the water, and I carefully lifted her storage bin ahead of me. Once we were on the beach I carefully put the bin down and for a second I panicked as I felt her going over forwards on me, but then Ami did a full-on handstand into a bridge over and ended up on her feet.

"Holy crap," I said, eyebrows raised. "That was so graceful."

"Thanks," Ami smiled, then tentatively stepped up and gave me a peck on the lips. "And thanks for helping carry my stuff."

"I'll get you on the way back, too," I promised.

"OK," she smiled, biting her lower lip for a moment like she was thinking, then she pecked me on the lips again, pushing her body a little closer this time so that I could feel her tits against my chest for a moment. "Have fun with Becca and Cass. Becca said you're her Spider-Man this morning?"

"I am," I said.

"Maybe I should find a superhero for you to pose with me," Ami said. "Would you want to do that?"

"Absolutely," I told her. "Just let me know if you have any ideas, Ami. I think you'd out-glam me in any picture ever, but I'd be happy to help out."

Chapter 93

I left Ami on the beach to get sorted and passed by Zenya getting carried by JC, with Leia following behind them carrying a piece of luggage over her head. "Whoa, need some help?" I asked her, quickly putting a hand on the luggage to help steady her.

"No, but yes," Leia sighed. I took one side of the big bag and helped her carry it to the beach. It was relatively light, just awkwardly sized to lift away from the water.

"Anything cool in here?" I asked her.

"Yes, but it's not mine," Leia said. "I'm helping Zenya this morning, and she's helping me tonight."

"Cool," I said. "Hey, do you want to hang out a bit later? I haven't spent that much time with you and I want to. I think you're pretty cool."

"Sure," she nodded, blushing a little. "Just come find me. I think you're pretty and cool, too."

"Not what I said," I teased her.

"I know," she laughed and winked. "Ginnie mentioned she got a little taste of your handiwork, by the way."

"She did, huh?" I asked.

"Mhmmm," Leia nodded. "Sounded a little more up close and personal than what I got. Any chance of you evening us out?"

"Maybe," I told her, and then openly eyed her up and down. She was wearing bikini bottoms and a crop top, her hips extra obvious in the outfit. "Let's talk with Cassidy and see what we get up to."

Leia bit the inside of her lips and nodded. "OK, sounds good."

I went back to the Single's Boat one last time, finding Sherry standing there and giving me a look. A look that I immediately recognized as trouble, and since nothing had really happened yesterday between us, other than me refusing to just randomly stop in the middle of driving the boat so that she could chat up the college guys earlier in the day, there was only one reason for her to be pissy.

"Good morning, Sherry," I said, trying to be polite if not sweet.

She narrowed her eyes at me, which was a pretty big expression considering her anime-large eyes that usually worked in her favour. "Did you seriously hook up with my sister last night?" she asked.

OK, so Heather probably told her, which meant she likely had a very large bent on who was at fault for the whole thing.

"You should probably talk to your sister about that," I said. "But I will say we all played a game that got a little out of hand last night. Most of us had fun, and everything anyone did was consensual."

"But you still hurt my sister's relationship," Sherry said bluntly.

I rubbed my forehead and sighed. "I can't really talk about that because I don't know, Sherry. It's their relationship. You need to talk to Cattie about it. Do you want my help getting to the beach?"

"No, I'm going to work up on the top deck," she said, turning on her heel to go back into the boat. She stopped in the doorway and turned, looking back at me in the water. "Stay away from my sister, Robert. Mess up your own relationship and keep your nose out of other people's." Then she slammed the door, though slamming a sliding glass door was harder than it looked and it was more just a rough slide.

Back on the beach, I found Cassidy and Becca waiting for me up out of the surf. The sun was just starting to warm the horizon, a glow starting in the sky. Golden Hour was almost upon us.

"Good morning," I said as I walked up. "Mary Jane. Mary Jane," I nodded to them. Both women were looking stunning. Both of them were wearing copper-red wigs properly styled to look natural, and Becca was wearing a similar-but-different Spider-Man shirt except hers had been hand-cropped and was frayed at the bottom hem and chest, showing off just a touch more cleavage than Cassidy was along with a similar red bra. She also had a crop leather jacket hanging open over top.

"Morning, Tiger," Becca grinned, and glanced at Cassidy who gave her an encouraging nod. Becca stepped forward and grabbed the front of my shorts, pulling me close and into a warm, long kiss that immediately had some tongue involved. Her hand slithered from her grip on my waistband and into the shorts proper, quickly wrapping around the root of my cock and giving me a squeeze. "I dreamed about you last night, you know," she said quietly with a smile.

"You did, huh?" I asked.

She nodded. "Want to make my dreams come true?"

"That depends," I said. "Am I carrying you two back to the boats right now, or are we doing this photoshoot first?"

She laughed and backed off. "OK, work first. Good point. Plus, you need to get properly dressed." She went back to Cassidy, who was holding a knapsack along with our equipment bag, and Becca pulled a Spider-Man bodysuit out of it. "Take off those shorts and put on your uniform, Tiger," she said, handing it to me. "It's time to go to work."

"I think my Spidey Senses are tingling," I said, glancing down at the bulge my cock was making in my shorts.

Cassidy and Becca both snorted as they started laughing.

Chapter 94

The good news was Cassidy had encouraged me to wear a pair of my tight briefs, so I wasn't naked under the Spidey Suit with my dick making a super obvious penis-shaped bulge.

Once I was changed, with both women giving me little wolf whistles as I did it, we hiked up a little way to a taller rock formation that wouldn't cast a shadow over us and that we could use as a backdrop. We just barely got our cameras set up and our tripods deployed by the time both of them looked up and said it was time.

We started with me as the photographer, and Cassidy and Becca posing as twin Mary Janes. They did some cute poses, and some meme poses pointing at each other shocked. Becca had a few more props, like a framed picture of Spider-Man that they fake cried over. Then they did a few sexy ones, staring into each other's eyes and looking like they were about to kiss. They didn't - it was a pretty standard Cosplay Model thing that I'd seen Cassidy do with other models a hundred times.

Then we set up the cameras on the tripods and we took some group shots with the three of us. Serious. Silly. Sexy. Having two Mary Janes draping over me, pawing at my Spidey Suit, biting their lips and giving me 'fuck me' eyes... Well, it was tough to stay focused. And tough not to get obviously hard.

Next, we quickly shot more duo pictures, this time with me and Cass, then me and Becca. These included me getting the mask rolled up to my nose and getting some kisses from both of them, including some classic Spidey Upside-Down kisses like in the first movie with Kirsten Dunst. The ones with Cassidy Becca directed me to do some weird things with the wall, and she swore that she could edit the photos to make it look like I was hanging from the wall. Cassidy didn't know how so Becca's duo photos couldn't be directed properly for that sort of thing and she got a few more of the sexy photos instead.