AMA - The Boyfriend Ch. 061-070

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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 boob-touching, flirting, fingering, and some questioning about the App.

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 61

"I mean, if you're offering," I said, trying not to nervously chuckle. Considering everything else that had happened so far on this trip, touching Ami's boobs wasn't even that crazy, but it was still more than I would have thought proper or possible thirty-six hours earlier.

I sat down on the couch next to Ami, and she sat up a bit more to present them to me. "Go for it," she said. "No one else is enjoying them other than other women who want to feel what they're like."

She took my hands in hers and put them right on her tits. "Damn," I said, more surprised than I necessarily wanted to sound. "They feel really nice."

"Right?" Ami laughed. "I told you, I wanted the big anime titties so I splurged on the best I could get. I was already decently sized, so going up to my ideal size didn't take too much."

I was cupping her tits, squeezing them softly, and without thinking I ran my thumbs over her nipples. She sucked in a breath, and I stopped. "Sorry, too far."

"No, it's just- It felt good. Don't worry about it," she said.

I kept squeezing and running my fingers along her boobs for another minute or so, then sat back. "I could do that all day and be happy," I laughed.

"That's how I feel!" Ami laughed with me. She leaned back, making no moves to put her shirt back on yet. "Um, Cassidy isn't going to freak over this, is she?"

"No," I said, shaking my head. "Honestly, I'll probably tell her as soon as I get up there and she'll want a feel at some point, too."

"Hah, well, as long as she asks first. I'm not a fan of surprise titty honks," Ami grinned.

"I'll make sure she knows to be polite," I chuckled and made to stand.

"Robbie, you don't think..." Ami trailed off.

"What's up?" I asked.

"Nothing, don't worry about it," Ami said.

"Alright, come on," I said. "You can't say something like that and then not follow through. I'm going to be questioning everything for the rest of the day if you don't ask me."

She rolled her eyes and smirked a little. "Now you're asking for me to tease you about it."

"Hey, I can tease just as good as you can," I said.

"Oh yeah?" she said. "I don't think- yikes!"

I interrupted her by picking up one of the beers and quickly pressing the cold glass to one of her nipples. She erupted into giggles after the brief contact. "Careful, when these things really get going they can cut glass."

"I'd like to see that," I said, then felt heat flush to my face. It might be the most forwardly flirty thing I'd set yet that wasn't a frank conversation.

"Naughty boy," Ami shook her head.

"Alright, now I really should get up there. Thanks for offering me a feel, they are truly spectacular."

"Thank you," she grinned. "If you want another one, just let me know. I'd be happy to oblige."

I took a chance and after I stood, I leaned down and gave Ami a kiss on the cheek. It was her turn to flush just a little bit but covered it with a smile. "The glasses are super cute on you, by the way," I said as I left back out onto the porch.

Upstairs, I saw that the speedboat had pulled in close again and Becca was trying to keep track of who was where. I silently held out a beer for her and she accepted with a thankful smile and a squeeze of my forearm. Then I went and re-joined Cassidy and Cattie at the chairs, handing Cattie the second beer. Cassidy had gotten talked into one of Heather's icy drinks and was sipping on it as slowly to keep from getting tipsy.

"JC got up on the skies," Cassidy told me, standing up to let me sit down again, then sliding back into my lap. "He's pretty good, but I bet you'd be better."

"I'm happy where I'm at," I said, giving her a little hug.

"I bet you are," Cattie laughed. "You know it's not fair that you rub all those snuggles in my face, right?"

"You want to switch?" Cassidy offered. "You can snuggle in with him all you want, babe."

Cattie actually considered it for a moment before sighing and shaking her head. "No, that would just make Heather jealous and act out. She'd be walking around topless and leading these guys on even more than she already is. You know, for a lesbian she really likes attention from guys."

I could almost feel Cassidy swallow down a snarky comment.

"Speaking of attention from guys," Terra said, coming over from where she'd been lounging against the railing of the boat talking with Leia and one of the guys.

"Speaking of it what?" Cassidy asked.

"No, that's it," Terra said. "All the guys keep staring over here wondering why Robbie is surrounded by pretty girls who won't give them the time of day."

"Well, it makes sense that you came to join us," Cattie laughed. "What's your excuse?"

"My boyfriend has been seduced by a big engine and planks of wood strapped to his feet," Terra grinned.

"You want to finish your massage from yesterday?" Cassidy offered.

"No, no," Terra sighed. "Not with all these guys around, anyways."

"Well, we did Becca's shoot while you were all off on your hike. It went really well," Cassidy said.

"Oh, do you have pics already?" Cattie asked. Both of them were planning to participate, though I doubted they would be quite as intimate as Becca.

"No, we handed the memory card over to Becca since she'll be the one editing and posting them," I said.

"I got some really great shots though," Cassidy said. "Super hot, super artsy."

"Cool, can't wait for my turn," Terra said.

"You want a turn on the tube, little missy?" one of the guys said, wandering over from where he'd been talking with Ginnie.

"God, no," Terra said. "With my luck, I'd face plant and have black eyes for the rest of our trip."

Terra drew the guy away from the group, knowing we were the 'anti-fun' crowd at the moment, shooting us a knowing wink over her shoulder.

"God, she has a nice ass," Cassidy said, watching Terra leave.

"Yup," Cattie nodded. "I would eat a meal out of that ass crack."

Both girls looked at me expectantly. "What?"

"Oh, come on," Cassidy said. "Objectify our friends with us."

"Fine," I smirked. "She's got such nice buns she should open a bakery."

Both Cass and Cattie looked at each other, then burst out laughing at the same time.

"Too corny, Tiger," Cass said.

"That was the closest thing to a Dad Joke pickup line I think I've ever heard," Cattie giggled. "Please tell me you have more."

I sighed and started wracking my brain. "Let's see..."

Chapter 62

"Cass, you're falling asleep," you said. The Dad Joke pickup line conversation had faded off and now, with the sun still beating down on the hot afternoon, my fiancee was drifting off.

"MMm, just a little bit," Cassidy said.

"How strong was that drink Heather made?" I asked.

Cattie, who was still sitting next to us with her feet up, sighed heavily and adjusted her own position. "She makes them way stronger than necessary."

"I'm gonna go take a nap," Cassidy mumbled. She shifted in my lap and kissed my cheek. "I'm sorry I didn't stay Sober Cassidy for Sober Robbie."

"Not your fault," I smiled, giving her a squeeze. "You sipped that one drink for over an hour."

"M'kay," she said, and then yawned. She got up and moved towards the stairs, and I stood up to make sure she wasn't stumbling or going to fall. She made it fine, and I sat back down.

"Oh look, a free lap and hands," Cattie grinned and moved her feet from the Adirondacks armrest to my lap.

I rolled my eyes but smiled, taking her feet in my hands and starting to massage them. It was funny how much closer I felt to her in the short time we'd been on the trip - before this week we'd been friends, but she'd been Cassidy's best friend through their work. That meant there was a bit of a barrier, if only because I was the secondary aspect of the friendship.

"Look, I'm just gonna say it," Cattie said. "You're fucking good with your hands, Robbie, but I don't get how you gave Leia an orgasm just from this."

I snorted and gave her feet a tug, pulling her lower on her chair and towards me playfully. "I don't think it had all that much to do with me. Her feet are just her erogenous zone or something. That and Cassidy's dirty talk."

"Now that would have been interesting to hear," Cattie chuckled. She sat up a bit, looking around to see who was near us, before laying back again in her slouched position. "Speaking of dirty talk... any developments in her plan?"

I glanced around as well. Becca was over on the other boat's top deck, supervising the whole rowdy group of people swapping out on the boat and tubing. I understood her stress - we weren't really her clients or anything, but if something went wrong on the trip she was the one in charge. She handled it well, or else I would have probably been feeling even more Big Brother-y than I already did.

No one was immediately near us, Wanda and Heels being the closest as that same college guy was chatting up Heels some more doggedly as they hung out in the pilot's cabin in the shade.

"There has," I admitted to Cattie. "I don't want to kiss and tell, though."

"Well, I know about kisses," Cattie smirked. "I was one of them, remember? You're a great kisser, by the way. Anything else though?" She lowered her sunglasses to look at me.

I sighed, still working her feet in my hands, pushing my thumbs into the soles. "Just between us?"

"Of course," she frowned.

"I mean Heather too," I said.

"Not my secrets to tell," Cattie said.

"Then yes," I said. "I've, well, we've had a couple more... encounters."

"We?" Cattie asked in surprise. "Cassidy was there for both of them? Wait, when did you have time for two threesomes on this trip? It hasn't even been much longer than a day, and less since I found out I think."

"They weren't threesomes, really," I said. "The first one was late last night and was mostly just hand stuff. The second time was earlier today and was oral only."

Cattie narrowed her eyes, considering me as she quirked her pouted lips to the side. She was still wearing her bikini bottoms, which left her long, pale legs bare, and I started massaging up her ankles to her calves. "If it was late last night, that means you did something with someone on our boat," she said. "And since I know it wasn't me or Heather, and I doubt it was Terra or JC, that only leaves Wanda or Heels. And since we all went on that hike except for you, Cassidy and Becca then I have to assume the second one was our fearless leader. Did you go down on her, or her on you? She's fucking hot, honestly. Nice job."

She laughed as I must have gone flush. "No comment," I said.

"Good for you," Cattie said. "Stick to your morals. How did Cassidy take it?"

"Good, I think. I've tried to stay checked in with her," I said.

"And she's not pushing you, is she? How much did she get involved?" Cattie asked.

I squeezed Cattie's calf. "I had some worries about the same thing you are, I think. So far, she's only been hands-on with me; I don't think she's just doing this to try and get with women herself again. Honestly, I'm still- I still hurt, and I'm conflicted as hell about how I should be feeling at any moment, and I don't know if I should be trusting her but I do. If she wanted to she could have moved on from me years ago, but she didn't and she's trying her damnedest."

"It's because she loves you," Cattie smiled sadly. "Fuck, I wish-"

"Cattie!" Heather called from the other boat. She was standing over near the pilot's cabin on the Single's boat, and when we both looked over she waved with a stern look on her face.

"Ah, shit," Cattie grunted, but waved with a smile. "She's jealous."

"Why?" I asked. "Does she know about this morning?"

"No, and that's not something to be jealous of," Cattie said, pulling her legs from my hands and standing up with a sigh. "It's the kiss from last night. She thinks we're uneven now, even though she agreed she put me in the position. She wants me to spend more time with her but also knows she can't just dominate all of my time. She probably just noticed that Cassidy isn't here anymore. It's gonna take a bit to calm her down."

"Whatever you need," I said. "Could you just... do me a favour?"

"What's up?" she asked.

"Caaattiieee," Heather called again, making it sing-songy, and Cattie waved again without looking, holding up a finger to tell her to hang on.

"Don't let Heather make you go topless around these guys if you don't want to," I said. "I don't like seeing you uncomfortable."

Cattie smiled, though it seemed a little sad, and patted my shoulder. "Deal," she said. Then she turned and walked off, and I watched her bum in those tight bikini bottoms for a moment, but she caught me as she looked back and lowered her sunglasses to wink at me. Then she diverted toward Wanda and Heels, slapped Wanda on the ass and whispered something to her before darting to the gangplank between the boats.

Chapter 63

Before Cattie had even made it over to Heather, Wanda had extricated herself from her conversation with Heels and one of the college guys and quickly walked over to me. She was still wearing those baggy athletic shorts, which I had to assume was to hide her ass from the random guys, along with her red bikini top and sunglasses.

"Hey there, sailor," she said with a grin. She slid her butt onto the wide armrest of the Adirondack chair and leaned her elbows onto her knees and her chin in her palms.

"If I'm the sailor, does that make you the lady I've got back in port?" I asked.

She laughed, her grin flashing. "Maybe it does," she said.

I reached up and took one of her arms, and she sat up as I began to massage her hand softly in both of mine. "What exactly did Wanda say to you to get you over here so fast?" I asked.

"She said that our favourite guy needed to be entertained," Wanda said, and took her hand from mine and stood back up. "Sit forward. You keep putting those hands to work for someone else, now it's my turn."

I followed her orders and sat my butt forward on the chair, and she climbed up behind me and slid her legs under the arms so that I was sitting between her legs.

"Now lean back slowly," she said, putting her hands on my shoulders. I could hear the smile in her voice as she guided me back until I was leaning back against her chest, the breasts pressed against me lightly as I stopped short of putting my actual weight on her. "There it is," she said quietly in my ear, and started kneading my neck.

"Mmgh," I said, wincing as she found a knot quickly.

"Jesus, Robbie. You are tense as hell."

"Yeah, I'm a little... stressed," I admitted.

"Too bad we can't take care of it in a more fun way," she whispered in my ear.

I couldn't help but smile at the implication.

"Now," she continued as her fingers pressed higher up to my hairline. "What's on your mind?"

"A lot," I said.

"Do better than that," she urged me. "I know you can. I have a hard enough time getting my husband to open up about his feelings. I'm not looking to enter the arena to drag yours out, too."

"I'm a worrier," I said. "Cassidy told you. I've got Older Sibling tendencies."

"Who are you worried about?" she prodded. "I'm right here. Where's Cassidy?"

"Taking a nap down in our room. I'm not worried about her right now," I said.

"I hear a 'But' in there," Wanda said. Her fingers moved up higher into my hair massaging the back of my scalp. "When do you worry about her?"

"Never," I said. "At least, not since..."

"Since you found out she cheated," Wanda finished for me.

I nodded, and she pushed her fingers higher and firmer along my scalp and through my hair. "I'm still thinking about that," she said. "Whether it's a good idea if we do anything else."

"I understand," I said. "It's a lot."

"I'm not saying no," she clarified. "God, Robbie, you and her together? You're magnetic. I'd want to sleep with you either way, but I think I've gotten wet by accident more than a couple of times today thinking about last night."

I reached back and patted her outer thigh. "I have to admit, I've been thinking about you as well."

"Good," Wanda said, her voice getting a little huskier as she whispered again. "Because if I do decide to do more, I hope you'll be ready too."

I closed my eyes and debated whether to tell her or not. The tipping point was knowing that secrets were what caused all the bad emotions in my situation to begin with. I had to tell her the truth, or things could turn worse instead of better. "I need to tell you something," I said.

"Well that sounds ominous," Wanda said. "Is it that you already got a blowjob from Becca and blew her mind when you ate her out?"

I twisted around to try and look at her, and she was grinning. "She told you?" I asked.

"I've known Becca a lot longer than you might think," Wanda grinned. "We came up online around the same time and have roomed together for more than a few Cons over the years. We've never done a shoot together so most people don't know about it."

"Are you OK with...?"

"With Becca getting hers? Absolutely," Wanda said. "I've been telling her for a while that she needs a good fuck to wipe out all the bad mojo her ex left. You are planning on fucking her, right?"

"We're taking it... slow," you said.

Wanda rolled her eyes. "Slow my ass. You've already hit first, second and third base on this trip. I'd put money on you rounding home plate by the end of the day."

"That's not what I'm trying to do," I protested.

She glanced around, then leaned forward and gave me a soft, sweet and short kiss on the lips. "I know, Tiger," she said, picking up Cassidy's nickname for me. "That's why I think I'm probably going to fall into bed with you as well. Now turn around so I can keep massaging you. If we keep going like this you're going to be tenting those swim trunks of yours."

I sighed and did as I was told, and she went back to massaging my scalp. "Now. If you're not worried about me, and you're not worried about Cassidy, who is it you're worried about?" she asked.

"Everyone," I said.

"That's a big list, Robbie," Wanda said. She trailed her fingers down my back and then up and under my shirt, softly scratching my back. As a massage it was completely ineffectual, but fuck did it feel good. "Planning on sleeping with everyone on this trip?"

"No," I said, shaking my head. "It's not like that. I just think some of the girls are a little more... cavalier in trusting than others are."

"I think the word you were looking for is naive," Wanda said. "And that's true, but even Sherry is old enough to drink and old enough to make her own decisions. Plus she has her sister here to look out for her."

"I didn't say my worries were rational or reasonable," I sighed.

"Heels might fuck that guy," Wanda said. I could feel her chin rest against my back as her fingers travelled to my sides. "Is that something you worry about?"

"I mean, I don't like the idea of anyone on the trip taking a risk like that," I said. "We don't know anything about these guys."

"Well, some of us do. At least those of us who have bothered talking to them," Wanda pointed out. "Robbie, you need to relax. Until someone asks for your help, then you can go ham wild if you want."