AMA - The Boyfriend Ch. 271-280

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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 relationship conversations and check-ins, date prep, and a long-awaited threesome begins.

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 271

"We need to talk about something else," I said.

Things had calmed down after a few minutes. Not that we'd gotten wild or were sobbing or anything. And thank God I didn't have another panic attack or anything. Now we were lying snuggled up and holding hands under the covers.

"Anything, Tiger," Cassidy sighed. We hadn't exactly come to a conclusion on the topic of how she felt about all of the relationship stuff deep down, but there wasn't really a wayto do that.

"Cattie is in it with us now, and I know you want her to move down with us," I said. "And I think it would be amazing if that's what she wants. There are logistics to figure out, but that's small stuff. But we're about to have a date with Becca, and she wants in too. We all know it. So what doesthat look like?"

"Well, you tell me," Cassidy said, squeezing my fingers. "Do you want her to move in with us as well? Or is stuff with her going to be more slow-going, like long distance?"

"Well, that's a question for her," I said. "If I had my way though..."

"You'd want her with us too," Cassidy guessed, and I nodded. "Same with Wanda. And I know, it's the subject we're not supposed to talk about because she's not broken up with her asshole husband. But if we're talking about planning for the future, we need to plan for her too. Wanda is going to want to move in with us. Long distance won't be enough for her. That's at least four of us, maybe five, and doesn't even account for Ami or Leia." She lowered her voice, getting a little closer to me so she was whispering. "Or Terra."

"Cass," I said.

"I know, I know," she said. "But it's another variable. Hell, we could include Zenya in that too even if it might not happen at all. Though the difference of planning for four and eight is a lot bigger than seven and eight."

It was, quite honestly, a little disconcerting to consider that it would be easier to manage a poly relationship with over half a dozen women than it would be with three.

"So at least four of us together, almost certainly five, and maybe up to eight... or nine," Cassidy said.

"We're gonna need a bigger bed," I groaned.

"We're going to need a bigger house," Cassidy countered.

We had savings, but not savings like that. I made decent money at the Hotel, especially after my last promotion and raise, and Cassidy made about three-quarters of what I was right now. It would have been more - probably a lot more - if she dressed in more scandalous costumes but she'd always played it safe with that. We couldn't afford a bigger place at the moment, just the two of us, and-

"Tiger," Cassidy said, interrupting my thoughts. "Stop stewing and brewing. It's logistics, we'll figure it out."

"OK," I said.

"I don't think we can talk any more about what the greater relationship looks like without others here," she said. "Or knowing who wants what. I'll just say that I'm excited to have Cattie with us because it'll be like having a sister who I love in the house, and adding more than that is OK with me. We'll figure the rest out."

"Alright," I agreed, thinking of the feeling of waking up with Cattie, Cassidy and Wanda in bed with me that morning. Of seeing Wanda in the dark of the room at the same time. God, I wanted that. "Then there's one last thing before Cattie gets here," I said.

"The App?" Cassidy guessed.

I nodded, squeezing her hand. "I'm sorry I need to ask, but... things are all still the same, right? With the perks?"

She frowned and nodded, and I could see the guilt in her eyes. She wasn't mad at me for asking, she was mad at herself because she knew she needed to.

"Then we need to decide if we're telling them or not," I said.

Cassidy swallowed and nodded again, then sat up and little and I joined her. "I... Look, I think it should be your decision, but I do have thoughts," she said. "And the reason I say it should be your decision is becausewe aren't going to be dating them, you are. But I think it's... Fuck, I think it's dangerous to tell them. It's messed with my head for years, and yours almost every day since I told you. The App isn't making them love you - at worst, I think, it's making them feel more comfortable and friendly withme so they feel more comfortable doing stuff with you because I approve. Comfortable isn't the same as love, though. If you weren't who you are, then maybe they'd have sex with you but not fall in love with you. This week would have been a little more towards the minimum of what I hoped, instead of this maximum; just a bunch of sex, not love."

"But if it isn't affecting them, then it's not something they need to worry about," I pointed out.

"Except that's only rational if you believe the App is realand buy into the rules and logistics of it. As soon as I prove it's real somehow, each of them might feel a lot different about it."

I nodded along, knowing she was right. Taking a long breath in and out, I had to consider that after everything this week, telling them about the App could blow it all apart. The simplest bad-case scenario was that they all thought I had hidden the fact that I was insane and they got the Ick and ended things. Everything else got worse from there.

"I can see your brain working again, Tiger," Cassidy said. "Can I guess what's on the tip of your tongue?" I nodded and she pressed her lips together for a moment before guessing. "But they deserve to know."

"They do," I sighed out, nodding.

"Probably," Cassidy said. "But... sometimes the truth hurts. You deserved the truth as soon as I woke up and realized what an absolute cunt I had been back when I stopped with the App, but I didn't know how to handle telling you. And just becausewe need to have Radical Honesty because of my fuckups, doesn't mean they want to live that way. Telling them removes their agency in being able to decide if they want to know as much as not telling them."

"Fuck," I sighed, knowing she was right. "Isn't that philosophically moot, though? If telling and not telling both remove the choice, then they are equally good and bad and we're just back to deciding whether to tell them or not."

"Then there's the question of who you tell," Cassidy said. "Just girlfriends? All of them? What's the threshold?"

I didn't have any answers. And with time running out before Cattie would come to us, I doubted we would figure it out.

"If you want me to do it, just tell me," Cassidy said. "OK? I can do it, and maybe separate it from you a bit. I'm the bad guy with this, not you. Whatever you decide, Tiger."

"OK," I nodded. "I'll figure it out."

Chapter 272

The knock on the door was light. "You guys ready for me?" Cattie called softly.

I got up and went to the door, sliding it open and pulling her in. She'd put her bikini top back on, and she barked a laugh as I hauled her into my arms and spun her around once before carrying her to the bed. I wasn't actually lifting her up all that much so I set her down and cradled her face, kissing her with little pecks as I leaned her backwards until we both fell onto the bed.

"You may want to close the door," Cattie giggled between the kisses. "Your ass is out."

"Let 'em look," I growled playfully, but after a few more kisses and laughs I stood up and slid the door shut.

Turning back to Cattie, I took in a breath and couldn't help but smile as I looked at my girlfriend sitting on our bed, looking at me. "OK," I said after letting out the big breath. "This might be an emotional talk. Do you want to do it snuggled up in comfy clothes, or naked, or something else?"

"I assume you guys do this naked?" Cattie said, glancing from my naked body to Cassidy, who was still half under the covers but topless with her tits on display.

"We do it all sorts of ways," Cassidy said. "But this one is my favourite."

"Sometimes I might want comfy sweaters and sweats, but right now I think I want naked," Cattie said. It was the work of moments to strip her out of her bikini and soon we had her between us under the covers of the bed. I was lying on my back, propped up on some pillows a little, while she was leaning into with her chest to my side, and Cassidy spooned up behind her.

"God, this feels good," I said after we settled in.

"No complaints here," Cattie said.

I reached up and ran my fingers through her bangs, pulling her silky black hair from her eyes so I could look into them clearly. "OK, beautiful," I said. "It's been a couple of hours. First things first, how are you feeling about confronting Heather and Sherry?"

Cattie took a long breath in and out and then distracted herself a moment longer by pressing her lips to my chest, kissing it softly.

"Cattie, babe, thinking things through is encouraged but delaying isn't," Cassidy said quietly, stroking Cattie's hair.

"Sorry," Cattie said. "I'm just... I'm still adjusting. This is a new dynamic that I'm not used to."

"Adjust as much as you need, at your pace," I said. "We want to check in on you, but that doesn't mean it has to be here and now, or like this, or anything else."

"No, no," Cattie said, "This is good. Um. I'm... I don't care about Heather. I was serious about what I said, and I'm going to stick to it. I nothing her. Literally the only thing I feel is that I regret I was with her when I met you guys to begin with. That relationship delayed this one. She was a speed bump in my life, and I'll forget her as soon as I'm driving away."

"You have a right to process things," Cassidy said. "You canget to nothing, you don't need to start there."

"I know," Cattie said. "But, I mean, I'm not feeling empty here. I feel like it's a crude analogy, but I'm trading up here. Heather was a mean old beater car that guzzled my money, embarrassed me constantly and was an anchor. Now I've traded up to a relationship that's a super flying car with all the gadgets and whistles, and this conversation is like a lifetime warranty. Not that I see you guys as a trade up, but you get it, right?"

"I get it," I chuckled. "No regrets yet?"

"Not a single one," Cattie said definitively.

"And what about this afternoon?" Cassidy asked. "I know you know what you're getting into, but it's different seeing it. How did you feel seeing him with Zenya?"

"Other than horny?" Cattie asked with a blush, looking back at Cassidy over her shoulder, then turning to me. "You both looked so hot together, Tiger."

"I guess that answers that question," I chuckled. "If something happens with Zenya again, and she's open to it, would you want to join in?"

"Tiger," Cattie said, lowering her voice. "Master. I will have sex with anyone you want me to, as long as you're with me."

"Good answer," Cassidy said, squeezing her friend tight.

"No," I disagreed. "It's not good enough. I appreciate it, but that's not what I asked. Catherine, is Zenya someoneyou would want to fool around with?"

Cattie blushed again, a little deeper this time, and nodded.

"I never want you to feel like you need to have sex if you aren't feeling it," I said. "Sex isn't something you should ever feel compelled to do. Even with me. We only stand for the best sex possible, and that means it needs to be enthusiastic."

That, for some reason, broke Cattie and she started crying, clinging to me. I shifted a little so I could get my arm around her as she curled up against my side and chest, and Cassidy started hugging her tighter from behind.

We both soothed her, trying our best to let her get out what she was feeling, until the soft sobs died down and she was sniffling. Cassidy slipped out of bed and rushed to the washroom, coming back with a wad of toilet paper and getting back under the covers, breaking the long strand into sections so Cattie could blow her nose.

"I'm sorry," Cattie said eventually.

"For what?" I asked. "You needed that. Do you want to talk about it?"

Cattie shook her head. "I nothing it. Now."

Part of me wanted to pry. I had to assume it had something to do with Heather. The way the bitch had spoken during their fight had been disgusting. Her view of sex and their relationship had been so warped, and even what little I knew of Dom/sub dynamics had made the way Heather treated it sound broken.

"I love you," I said to her. It wasn't the first time I'd said it while she'd been crying, but she was looking at me now as I said it and I pushed it at her with my gaze as well, trying to drill it into her mind. "If you ever do want to talk about it, either of us will listen. Or we can find a therapist. Cass and I are starting with a couple next week."

"Thank you," Cattie whispered.

"Now promise me you'll tell me if something is off if I approach you for sex," I said. "That's the only way we can fix it."

"I'll tell you," Cattie said. "I promise."

I kissed her forehead, then let her wipe her nose and lips again before she leaned up to kiss me on the lips.

"Now," I said. "What about Sherry?"

Chapter 273

Cattie was a lot more confused and hurt about Sherry than Heather. She really hadn't even started to process that betrayal yet, and when we opened the floodgates the mourning started. She didn't wail and scream, but she was deeply wounded and Cassidy and I spent the next hour just holding her. Occasionally we talked a little, and I had to turn off my 'problem-solving brain' to just sit and be with her as she processed.

Cattie's family was kind of messed up. Sherry was only her half-sister for a reason, and Cattie had done everything she could over the years to be a good older sister even when they were split apart because of custody agreements and parents moving around. I couldn't fathom what had been going through Sherry's mind throughout the week. When I'd first met her in the parking lot of the boat rental place she'd seemed just a little shy, but cute and sort of bubbly. What had changed? And when had that change really started? It couldn't have happened over the course of the trip, it had to have started earlier than that.

I didn't say my suspicions out loud. It might have further hurt Cattie instead of helping to just explain things.

Heather was an aggressive predator without any sense of sexual boundaries, as far as I could tell. How likely was it that she'd set her sights on Sherry long before this week and been laying the foundation of getting her into bed?

Cattie eventually got up and took a shower, feeling gross after all the crying. I wanted to go with her, or at least have Cassidy with her, but she just shook her head and asked for a bit of alone time. Cassidy snuggled into my side as soon as Cattie shut the washroom door and cried a bit again herself, though this time it was in empathy for her friend. By the time the shower turned off in the washroom, I was up and knocked on the door. She opened it, and I entered to dry her off with a towel myself. She cried again, happy tears, as I pampered her. Then we went back out and Cassidy met her in a big hug, promising that we'd both always be there for her no matter what.

This time, before getting back into bed naked, I made the executive decision that we needed to at least put some underwear on. Once that was accomplished we sat on top of the sheets and I held Cattie's hand.

"There's one more thing I wanted to check in with you about," I said. "Tonight Cassidy and I have a date with Becca. Unless something dramatically bad happens, the expectation is that I'm probably making things official with her as well." I had to stop and take a deep breath. "You're my girlfriend now, baby. That means if you have a problem with me having another romantic partner, your feelings and opinions matter a lot. It's also a big change...thing in the future. What do you think? What do you feel about that?"

Cattie's shoulders relaxed a little as I talked, and when I finished she leaned over and kissed me. Cassidy, watching with a big grin, squeezed my other hand.

"Tiger, I knew that was coming before I bought in on Us officially," Cattie said. "Becca and Wanda are your girlfriends already as much as I am."

"We don't talk about Wanda yet," Cassidy stage whispered to Cattie with a smirk on her lips.

Cattie rolled her eyes at Cass but turned back to me with an apologetic smile. "Sorry, I know where you're at with that. Overall, I'm in love with you and I'm dating you. I'm also best friends with Cassidy, and I'll be the loudest person cheering when you marry her, and when you say go I'll happily have sex with the two of you. I'm not looking for romantic connections with the others, but the same goes for them. Becca and she-who-is-not-available-yet are both lovely and if they are in for some fun with you then I am too. I think I'll probably stick with the same rule as Cassidy though. Only when you say yes, and only when you're there. My heart and my body are yours, that's what it means when I call you Master. Hell, that's what I mean when I call you Tiger."

"What if I give you free rein to play with them whenever you want?" I asked.

She smiled sweetly and shook her head. "I'd still come to you and ask nicely. Every time. Because I respect you as my partner."

Now it was my turn to lean in and kiss her.

"Told you it would be fine," Cassidy said with a smirk once our lips parted.

"Baby, I will swat that ass," I joked.

"Oooh, promises!" she giggled.

I just shook my head and looked back at Cattie. "Will you be OK tonight during dinner? Heather might decide to make a scene and we won't be there."

"I'll stick with Wanda," Cattie said. "And Terra too, probably. Any updates on her, by the way?"

I grimaced and shook my head. "We had a hard talk this morning. The door is still... I dunno, ajar? But she has a lot of decisions to make and the reality ofthis is different for her."

"Do you mind if I talk to her about it?" Cattie asked.

"Baby, you can talk to anyone you want," I said.

"But about you," Cattie insisted.

"Yes," I agreed.

"OK," Cattie nodded. Then she reached and pulled both Cass and I into a hug. "Thank you for this. I love you both."

We hugged it out, then decided we'd been in the cabin for long enough. Cattie quickly pulled out a cute, witchy black tank top with a cage of straps in the form of a pentagram over her cleavage and paired it with her bikini bottoms, while Cassidy threw on her Jason hockey jersey, realised how heavy it was even with the knit holes, and then changed to a crop top and jean shorts.

When we left I split from them - it was still a little over an hour until dinner and I had a couple more conversations I felt time pressure on. Less than a day left in the trip, and juggling eight (maybe nine) women all at different stages of relationship was fucking complicated.

Chapter 274

I found Ami sitting with Wanda up on the top deck. It felt weird to be surprised by that momentarily, but it also kind of made little butterflies flutter in my stomach seeing them together. They were so different, but I really was falling for them both.

"Hey, Robbie," Ami said, looking up from her book. She was in her reading outfit, which was topless, though with how quiet things were she had the peace to read and suntan at the same time.