AMA - The Boyfriend Ch. 071-080

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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 App exploration, heavy flirting and a game of dares kicking off.

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 71

Cassidy talked me through what she was doing, even though I couldn't see it on her phone. It looked to me like she was on Facebook Messenger and was playing with the settings. She went through the perks, turning each one off. No more memorable kisses, spectacular-tasting cum, or special massage hands. No more lucky accidents. Then she turned off the other two that I hadn't asked her about yet, offering to tell them to me. I was already feeling shitty for this conversation even though I knew it was a two-way street for the emotions going on, so I told her I didn't need her to tell me.

"But I do want to know what it says about the girls," I said.

"Are you sure?" she asked. "It's only going to tell us what they think of me, not you."

"I just want to know what you've been living with at your fingertips," I said. "I want to know what it would be like to see it in front of me."

'Alright, Tiger. Who first?"

"Becca," I said. We'd gone the furthest together so far, and Cassidy had been right there.

"Alright. Rebecca Jones. Asexual slash Bisexual. It gives me three scores. Affection score is like... how friendly they are with me. How much they like me platonically. For Becca that's a 54 right now, which is pretty high for someone I've only interacted with offline for a couple of days. And then it gives me a Love score, which is about romantic feelings. That's a 7. Love is usually the slowest one to raise, so I have to guess it's even that high because of the interaction between the three of us. The last one is Lust, which... honestly, it's the one that changes the most based on how horny someone is and if they're attracted to you or not, and is the only one that fluctuates down with frequency. Becca has a 47 Lust score right now, and I'd bet it's because we got cut off earlier."

"Does it tell you anything else?" I asked.

"Well, it gives me the option to see the highest suggested perks I could buy for her," she said.

"What are they?"

Cassidy tapped something. "It gives three suggestions. The first one is called 'Worry Knot,' which makes her feel more confident and worry less when she gets regular sexual interaction with someone she has a moderate or higher love score with. The second one is 'Fuck and Forget,' which looks like it's supposed to help her get over past traumas through repeating sexual encounters with someone she loves, though it's got a whole complicated explanation. And - uhm, the last one is 'Sister-Wife' and makes her immediately enthusiastic about sharing her love interest with me."

I was quiet for a moment, absorbing all of this. The first two seemed to be geared towards helping Becca overcome the negatives she felt, and even the requirement of sex with a loved one to do it didn't seem that horrible considering it was particular about it being with someone she loved. There was a world where what the App was doing would happen anyways - good sex could make you feel more confident about yourself. Caring, loving sex could help someone get over their traumas. But that last one... That last one was the dangerous one.

And it was also the one that sounded the most tempting, from a selfish position.

I could have Cassidy, and I could have Becca.

Fuck me, I thought. "Now Wanda," I said.

Cassidy manipulated her phone, and her eyes went wide. "Holy crap. OK. Wanda Berenson. Bisexual. Affection score 62, Love score 21, Lust score 68."

"She said she's still trying to decide if she wants to get involved with us again or not," I said. "I think she wants to, but she doesn't want to cause problems by jumping into our mess."

"Well, that makes sense," Cassidy said. "And I get the Lust score, and maybe even the really high Affection score after last night, and how much she seems to care about us, but I'm most surprised by the Love score. Twenty-one is high for someone we've known only this long, even if we have hooked up with her once."

I had a flitting thought, but crushed it before it could even form coherently in my mind. Wanda was married and had an agreement with her husband. That was all it was.

"What about her suggestions?" I asked.

"Hmm. The first one is 'Supportive Family,' which makes the person's family much more likely to back their decisions, especially relating to their love and sex lives. The second one is 'The Glass Pussy' which makes her perfectly proportioned for the person she is having sex with - she didn't feel particularly loose last night, did she?"

"No," I shook my head. "I thought she felt tight on my fingers. Maybe she's got like... a shallow vagina though? That's a thing, I think. What's the last suggestion?"

"Sister-wife again," Cassidy said.

I gulped a little. That was dangerous.

I wanted to ask for more. To check out Cattie, and Ami. And Leia. I thought about Terra teasing me about giving me the blowjob she'd promised JC. Or Zenya and Ginnie, who flirted like hell. But peering into the app was a massive temptation that I was wary of, and more than that it felt like an invasion of privacy. I'd just found out things about Becca and Wanda that I shouldn't have a hint at. That should have been theirs to tell me if they wanted to and when they wanted to.

Then I had a thought. "Now do Heather," I said.

"Mmm," Cassidy nodded. "Good idea." She had to scroll for a moment, then stabbed her finger on the screen before reading. "Heather Adams. Lesbian. Affection score 12, Love score -1, Lust score 72. Fuck, she really doesn't like me that much but want's to fuck me pretty badly."

I grimaced. I had no idea about the numbers, but that was the read I'd gotten on Heather from the start of the trip. I could only assume my scores with her would be even lower.

"Do you want to know her suggested perks?" Cassidy asked.

"No," I shook my head. "Not right now. I don't even want to think about helping her out with anything, the way she acts."

Cassidy looked like she wanted to say something, but decided against it and instead shut down her phone and slipped it back into my pocket since she didn't have any. Then she pulled me into a hug. "I'm so sorry, Robbie."

"I know, baby. I know," I murmured back, hugging her hard.

Eventually I lifted her off the boulder and brought her back to her feet on the ground, and we did some more hiking along the smoothest path we could, circling around where the houseboats were moored. We held hands when we weren't keeping our balance, and by the time the Golden Hour was coming to a close and everything was starting to get dim enough that it was hard to see, we hit the beach about a hundred yards down from the boats.

I stopped us, and turned and took Cassidy's hands in mine as she looked up at me with a pensive expression. "Cass, this is all really hard to tackle and wrap my head around, but I still love you."

"I love you too, Tiger," she said, and let me pick her up to kiss her as she wrapped her legs around my torso and her arms around my shoulders. "I love you forever."

Chapter 72

Cassidy and I made it back to the houseboats, hand in hand, just as full dark was settling in. The girls got the party lights on the top decks running, and I ended up needing to help carry some girls back. Leia in particular rode on my shoulders similar to how Cassidy had since she was all done up in another set of fake armour.

Once I helped her up onto the back porch of the boat she turned around while sitting on her butt and leaned down to me in the water, giving me a little friendly kiss. "Thanks, Tiger," she grinned.

"No problem, hon," I said with a smile, winking at her and then turning to head back to the shore. She hadn't made a face or anything, hadn't given me any sign that things had been different. And she'd still kissed you.

"Is that the toll?" Wanda asked me as I came back to the shore.

"Hmm?" I asked.

"We get a ride, and pay you with a kiss?" she clarified.

"I'm only accepting donations today," I said with a grin.

"Well, in that case maybe I want to donate more than a kiss," she grinned and bit her lip.

I shook my head. "You, blondie, are dangerous."

"So are you, Tiger," she laughed and winked.

I did help her, though she only needed me to carry her backpack of gear. Wanda had done a lingerie shoot by herself, and was traipsing around in a pretty bra and panty combo that covered more than some of the bikinis a couple of the girls had been wearing, so she swam back herself. She did end up getting me to help her climb up onto the porch though, and I ended up with a face full of her ass as she 'slipped' and smothered me for a moment.

"Oops," she smirked, pulling away and giving me that teasing smile of hers.

"Try it again and I might take a bite out of it," I teased her back.

"Mmmm," she hummed, raising her eyebrows suggestively.

Since Wanda was the last person needing some help to the boats, I returned to shore one more time and found my wet swimsuit that I had laid out on a rock over the hike. On my way back I noticed Becca hanging out on the Singles Boat back porch, so I swam passed the Couples boat to her and pulled myself up. "Hey. Everything good?"

"Yeah, for sure," she said, and sat down next to me, dipping her feet in the lake. "I just wanted to make sure everyone got back OK, but it looks like you beat me to it."

"Happy to help," I said.

She glanced back over her shoulder into the Singles Boat living area and kitchen, but no one was there. Then she leaned over and gave me a kiss. "I had fun today," she said.

"I did too," I said. "A lot. I'm sorry we couldn't continue."

"I'm sure we'll get a chance," she grinned and then grabbed my cock through my wet shorts. "You know, I haven't had sex in a long while. I might need more than one round next time."

I was quickly getting hard as she fondled me, and I groaned a little in appreciation. "I would be more than happy to oblige," I said. "We just need to find the right time when all the children aren't underfoot."

"Well, it's not going to be tonight," Becca said. "We're doing a girls-only sleepover movie tonight, and I think I heard Heather say she wanted to do a couples game over on your boat. Which brings me to my next order of business - before people start settling down, we need to separate the boats for the night."

"I can help with that," I nodded.

"Great," she said and then kissed me again. She started to stand, but I grabbed her hand in mine and stopped her.

"Becca, I just want you to know, I'm more than a little infatuated with you," I admitted to her. "I'm really glad we met. You impress me almost as much as you turn me on."

"Guess that means I need to step up my game to be more impressive," she laughed, then leaned in while sitting on her knees and kissed me again. "I'm more than a little infatuated with you too, Robbie."

She stood and offered me a hand to stand up, and we got to work unmooring the boats from each other. Cassidy came looking for me as I was just putting away the planks from between the boats and joined me in the Pilot's Cabin as I turned the engine over.

"Hey, Tiger, just so you know Heather is planning a couples game downstairs," Cassidy said.

"Becca mentioned she heard something like that was happening," I said. "Do you want to play?"

"I think it's kind of expected we will," she said. "But I just- It's Heather. She's been boozing everyone up and keeps trying to get us all topless, and she's doing the submissive thing with Cattie. I wouldn't be surprised if she tries to manoeuvre some... let's call it Not Safe For Worksomething into whatever this game is. I just want to know what your hard boundaries are, so I can automatically shoot anything down that goes too far."

I started moving the boat forward, sliding it out from beside the other, and pulling into slightly deeper water. It gave me a couple minutes to think, and by the time I dropped anchor I turned and kissed her lightly as she sat on the counter. "Belly and up," I said. "Everything below the waist is mine, and you don't let anyone touch it or see it. Other girls other than Heather are fine to flirt with or touch above the waist if it's part of the game."

"What about JC?" she asked.

I frowned a little but shrugged. "Kissing only, no groping, but try and keep it friendly. Terra's already been kissing me so I feel like I can't just hard No or seem like an ass, but I don't like the idea of watching you with him in any way."

"OK," Cassidy nodded. "That's all fine with me. Are you sure about the girls, though?"

"I trust you with Cattie and Terra, and we've already gone pretty far with Wanda that any line I drew would feel silly. I'm not even sure where Heels would put her own line, but in a game I'm fine with it. Heather is the only one I don't want getting her hands on you, OK?"

"I love you," she said, and kissed my nose. "And I like you telling me my boundaries. It's hot. Is there anything youdo want to see?"

"I don't even know what the game is," I said. "We might be worrying about nothing."

Chapter 73

"The game is Couples Truth or Lie," Heather announced.

We'd all gotten changed by now, and had been summoned to the living area of the houseboat by Cattie. I'd changed back into my loose athletic shorts and a t-shirt, while Cassidy had put on a cute pair of striped bra and panties along with a long shirt that could double as a short dress that looked like a blood-spattered hockey jersey with Jason's goalie mask on the front. She'd used it in a Halloween costume a couple of years before and it had made it into her regular rotation of nerdy lounging clothes. She'd pulled on a pair of tight black workout shorts underneath it, and had asked me how I'd like her to do her hair, and I'd suggested the cute half pony she did. She'd smiled and kissed me before preening herself in the mirror.

The coffee table in the living area had been moved aside, the interior lights had been dimmed and someone had hooked up a laptop to the TV so it would cycle through some sort of trippy screensaver. Cassidy and I had been directed to sit together, and now all the couples (and Wanda and Heels) were sitting on the floor forming a squared circle.

"The rules are easy," Heather continued. "A couple spins the bottle and gets to ask an embarrassing question to the couple it lands on. You have to answer the question, but you don't have to tell the truth. If you lie and someone calls you out, you need to do a penalty pulled from this bowl. Every time the bowl is empty, each couple puts in a new penalty dare. Any questions?"

"How does the game end?" Wanda asked. She was dressed in a crop top sweater and short workout leggings that ended about mid-thigh, and knee-high socks. Her hair was pulled back in a ponytail, and the look was sporty-casual in an eclectic way.

"It ends when we want it to end," Heather said. "No winners or losers. But we can add shots to the game if you guys want. Any time someone spins the bottle, you take a shot."

"Let's do that," JC grinned.

There was a brief pause as shot glasses were found in the kitchen cupboards, and we all busted out the liquor we'd brought. I came back from our room with the vodka Cass had bought at the liquor store, along with cranberry juice. She grinned up at me happily and kissed the tips of my fingers as I sat back down on the floor next to her.

Once we were all back, Heather got each of the couples to write down a dare on a slip of paper, fold it and put it in the bowl. Then she knelt on the floor next to Cattie. Heather was wearing a yellow off-the-shoulder sundress that was actually very pretty on her, though she had on what looked like a stretchy grey athletic bra underneath it. "I'll do the honours and spin first," she said, then turned to Cattie. "Can you pour me a shot, babe?"

"Sure," Cattie said. She'd put on a long-sleeved black and white checkered button-down with the buttons only done up to her cleavage, and a pair of ripped-up jean capris that looked like they belonged on a girl at a punk rock show - which was a good look on her. She was also wearing her black-rimmed glasses, which I'd only seen a few times over her friendship with Cassidy, with her hair down. She quickly poured a shot of tequila while Heather produced an empty wine bottle and dramatically brought it to the centre of the floor and gave it a spin. Before it stopped, she'd taken the shot from Cattie and downed it quickly, licking her lips as she swallowed it down.

The bottle landed in the general direction of Terra and JC.

"Hmmm," Heather said, playing up her little ounce of power. "Let's kick things off spicey, but nottoo spicy. No need to scare anyone away, right?" She laughed and winked at us, and I don't even think she noticed that we only chuckled halfheartedly. "What's the craziest place you two have had sex?"

"Oh, that's easy," Terra said. "His parent's backyard during a 4th of July Barbeque. He was supposed to be checking the burgers on the grill, and instead we humped on the other side of the bushes. It had been three days we'd been sleeping in separate beds at their house and we were both horny as hell. I think we scared the rabbits that lived under the deck!"

That left us all laughing, and Terra reached for the bottle but JC stopped her. "Hold on, that's a lie!"

I almost spit out my beer as JC called it on his wife.

"The time we fucked at the baseball game was definitely the craziest," he continued. "We literally broke into the changing room and fucked on the benches."

That brought on more laughter, and Terra dropped her jaw and punched him in the arm. "You're not supposed to call Lie on your own team, Juan Carlos!"

"She's right. Now you guys need to do a penalty!" Heather declared.

"Oh, shit," JC said, facepalming his forehead hard.

Heather grabbed the bowl and held it out to them. Terra made JC reach in and pull one of the papers, and he handed it to her. "Go back to your room and switch clothes with your partner," she read. "Ah, shit. Can we skip my bra? He'll definitely wreck it."

"That's fine," Cassidy giggled. "As long as he has to put on your underwear."

"Who says I'm wearing underwear?" Terra laughed back, sticking out her tongue.

Terra had been wearing stretchy leggings and a clingy dress that highlighted her thin, athletic build, while JC had been dressed similarly to me in athletic shorts and a muscle shirt. The couple went back to their room and came back a few minutes later.

In my opinion, Terra looked pretty hot in guy's clothes. She'd used an elastic band to cinch the too-large athletic shorts around her waist, and the muscle shirt hung long enough on her to cover her ass, but the large arm holes were threatening to reveal her tiny chest with every move. JC, on the other hand, looked absolutely ridiculous. The dress, which I hoped was cheap, was stretched around his hairy chest to its limit and he'd tied it like a crop top at his abdomen with an elastic like Terra had his shirt. To be fair to him, he fit into the leggings even if they were stretched like crazy too, and they showed off every muscle including the awkward bulge of his dick. The real kicker was that he had the strings of a thong waistband riding high on his hips.