More Sisters, Less Problems

My wife, Alex, and I had never been what would would call particularly well off. We weren't destitute by any means, but we certainly weren't living in the lap of luxury. We had a modest sized, if fairly overpriced, apartment, working mundane office jobs to pay the bills. But despite that, we were happy.

We had been together for eight years, married for six of them, and while we both wished we could afford a home, or newer cars that would need less frequent, and expensive, repairs, we were happy as long as we had each other. Things hadn't been easy, a costly medical procedure that Alex needed put us into considerable debt and destroyed our savings, but we had managed to scrape through and having each other as support made that all the easier.

Alex's family had no idea. They knew, of course, but none of them had ever really dealt with the sort of financial issues we had put up with. The house her parents were living in had belonged to her grandparents, and her dad had received a sizable pension when he retired which had set them up pretty much for life. Her sisters also had some trouble understanding our situation. The oldest sister, May, was married to a successful lawyer, and even though they were still dealing with student loans the two of them, and their two kids, lived very comfortably in a large house just outside Boston. Her other sister, Hannah, had a good job, and her husband was an employee with a well known local construction company, so they were both bringing in good money as well. Granted, May and Hannah tried to be understanding, but neither of them really had the experience. May and her husband had gotten married and inherited some money from his grandfather, Hannah had gotten a great job right out of college and never had to look back.

And then there was Annie, their cousin. Annie had recently gotten married, much to the family's joy, and her husband was loaded. How loaded, you ask? They had a destination wedding, in a castle, in Ireland, and he didn't even bat an eye at the idea.

All this made some conversations with her family a little tricky. I had moved to the St. Louis area a year before meeting Alex, and while my family had never really struggled, and my parents had done fairly well for themselves, I had never really known true decadence on the scale of Alex's sisters and cousin. Although, to Annie's credit, she had only recently started living that lifestyle having been married for just over a year by this point. And while they never intentionally rubbed it in any faces, seeing pictures all over social media of their trips all over the world did sometimes make one wonder how out of touch they may be.

But they weren't bad people, in fact they were all quite lovely people. Annie could be a little abrasive at times, but we all got along quite well. May was the only one who didn't live in the area anymore, so whenever her family came to visit it was always a big event. Days were taken off of work, parties had and the likes. We didn't get a ton of time with her and her family, so we always wanted to make the absolute best of it.

This year, after May gave us the dates that she'd be back in town, the planning started early. Her kids and mine and Alex's daughter were roughly the same with my daughter being five and May's kids being seven, which was great, and Hannah's son had just turned three. May had mentioned a night for just the adults to celebrate her upcoming 45th birthday, somewhere outside the city and leaving the kids with their grandparents. My in-laws were more than happy to watch the kids, and the planning began.

Everywhere we could find that looked good wouldn't be available until the day after we were hoping to get set up. That left us trying to figure out where to go and what to do, since the other option was just sitting around at Hannah's house. That was when Annie chimed in on the group chat the sisters had set up, saying she had a friend who owned a nice, big, place about an hour's drive outside the city, and that if we wanted she'd be happy to reach out to him and see if we could borrow it for an evening. With a handful of "that'd be awesome!" replies, Annie said she'd reach out to him. It took a couple of days for her to get back to us, but she said he'd be happy to host a little get together if they were okay with him being there. Seeing as it was his property, none of us really had any objections.

May and her family made it to town, and while the grandparents took the kids to a local children's play zone, we adults grabbed some lunch to finalize plans.

"So yeah," Annie said "we go to Garret's place Wednesday, have some fun and celebrate our girl. He's even offering to put people up if everyone gets a tad too hammered."

"It's very nice of him to offer his place for this." Said David, May's husband.

"He's a nice guy." Annie replied.

The group consisted of Alex, May, David, Hannah, her husband Jason, Annie, her husband Nate and myself. So there would be nine of us at this shindig. While we tried to rope a few more of Alex's cousins into the party, having to plan it for the middle of the week made it tough for people to pull off. If Alex didn't routinely take at least a little time off when May was in town her boss might have fought her on it, and my boss was just happy to see me actually use some of my PTO since I only ever seemed to use it when I was far too sick to be able to go into the office.

"Garret bought this place to be a rental," Nate said "but he's between renters so it's open for our use."

Garret and Nate had been friends for a few years at this point, both being well to do property owners in the area. Nate owned some six or seven properties that he rented out, plus the house he and Annie lived in. Apparently he and Garret had met over their shared financial situation and really hit it off. Alex and I had sometimes joked that if Annie had gotten married before us maybe Nate would have given us a house, he had plenty to spare. He was a nice guy, though, so we tried not to begrudge the fact that housing was already in short supply and people like him and Garret were buying up multiple properties just to not live in them at all.

"Couldn't we have done this at one of your properties, Nate?" Asked Hannah.

"The only one I've got that would be big enough for this to be comfortable is currently booked that whole week. Everything else would be a tad cramped."

Hannah and Jason had offered to host if things fell through, but it was clear that they really didn't want to. Hosting eight people having drinks and getting a little rowdy, as we sometimes had a tendency to do, could be a bit much, and part of the appeal of doing it literally anywhere else was that they would have basically zero responsibility. They needed a break as much as the rest of us, with a very active three year old it was clear they needed to get away.

"Do we need to bring anything?" I asked.

"Other than ourselves?" Alex added in with a smirk.

"Probably any specific drinks you want. I think Garret mentioned that the plan to keep it pretty simple and he's just going to order a shit ton of food from a pizza place nearby." Annie replied.

"Lots of bread sticks." May chuckled around a mouthful of food, rather unlike her.

"Oh, actually," Annie said, turning back to Alex and I "if you guys wanted to provide games for the evening that would be great."

"Yeah, sure." I said with a smile. Alex and I had a pretty sizable collection of board games, including several party games more suited to an all adult audience. It seemed like a solid plan for us to provide such things, and we were always happy to have people to play with. We had amassed our collection over the years, but had always had trouble nailing down a friend group to play with on the regular, so many of our games saw little play as they didn't really work well with just two people.

We hammered out more details as we continued our meal, and eventually we had basically everything figured out. We were all pretty excited, it was always nice to get together as a group and just have some fun without having to worry about kids or grandparents who might not approve of some of our language and discussions. We didn't need judgment, we needed some relaxation.

The day soon came, Alex and I picking up May and David and the four of us driving out together with Hannah and Jason not far behind us. Annie and Nate had gone up earlier to help Garret get things ready, with the rest of us heading out in the early afternoon after a quick lunch with the kids and grandparents to say goodbye for the evening. Even if we didn't get too drunk to drive home, we had prepared to just stay there overnight anyway because driving home at night wasn't always what one might call fun.

When we arrived both Alex and I were astonished at the sight we saw. The building looked like a log cabin, but it was massive. It was probably as big as our entire apartment building, minus one floor, and I couldn't even begin to try and guess how much this beast cost. There was a detached garage that could easily fit six cars, a huge horseshoe shaped driveway that could accommodate another dozen cars and a sprawling front yard with beautiful full grown trees.

As we got out of the car I leaned over to Alex and whispered "who the hell needs this much house?"

"Someone with nothing better to do with their money, I suppose." She replied.

May and David seemed impressed with the cabin, but less flabbergasted than Alex and I clearly were. Two different worlds.

Upon entering the cabin we were met with a beautiful natural wood interior, which, despite the obscene size of the place, did make it feel a touch rustic. As we ventured further in we found Annie and Nate talking with who could only be Garret. They waved us down enthusiastically and introduced us to our host for the evening.

Garret was a fairly unassuming man. He had pale skin and hair that was more white than brown anymore, and wore a pair of thick rimmed glasses that were clearly in style somehow. He was average height, a little stocky, and clean shaven. He was also quite polite, greeting us with smiles and handshakes and, once Hannah and Jason caught up to us, offered a tour of the cabin.

We followed along behind him as he guided us through the building, pointing out the various rooms and the functions. From everything as mundane as bathrooms to the game room in the basement with a pool table, darts and foosball. It really did come across as a vacation home and not someplace someone would live, which made sense since that was Garret's intention with it after all.

When we made our way back to the kitchen and dining area there was another woman standing in the kitchen, fixing herself a drink. She was tall and slender with black hair that hung elegantly down to her shoulder blades.

"And this," Garret said in his quiet voice "is my girlfriend Isabella."

We all exchanged greetings with her, and she seemed just pleasant and polite, if slightly detached, as Garret. Afterwards we all gathered in the living room and sat and chatted for a little bit, Garret asking us some basic questions about our jobs and the likes, the weather in Boston and so forth. Basic small talk type shit.

"And how did you two meet?" Garret asked me, gesturing to Alex and I.

"Oh," I said after taking a swig of the beer in my hand "we met at a blood drive. We chatted for a bit and decided to stay in touch. We had been talking just as friends for a couple months before I decided to ask her on a date."

"He was very sweet." Alex added with a chuckle, patting my thigh.

"Savings lives and finding love, what a story!" Garret exclaimed. "And I understand you two brought some games for the evening?"

"Yeah, we grabbed a selection so people can vote on what they want to play." Alex replied, and as she did I got up and grabbed our bag with the games in them. I removed them one by one and laced five different games on the table in the center of the room.

Everyone looked over the options, and Isabella pointed to one and asked what it was.

"Oh, that." I said. "It's a 'how well do you know your partner' type game. There's a deck of cards with prompts, everyone writes down their answers and tries to see if they know their partner well enough. The twist is that this version has some more adult cards in it as well."

"Adult?" Annie asked with a smirk.

"Yeah, it's got some interesting stuff in it. We've only quickly browsed through it once." Alex replied.

"Well I think that sounds quite interesting, and fun." Garret said.

Everyone else seemed to agree with him, which actually shocked me a little. Jason wasn't normally into these types of games because he often felt awkward, but the chance to show how well he knew Hannah I guess made him agree with basically no argument.

We decided to wait until evening to play, and so we went about our ways around the cabin. Alex, May, David and myself went out onto the back porch for a bit, with Alex and I being in awe of the size of the yard and the ten person hot tub and large fire pit that were the clear showpieces of the backyard. Eventually Alex and I made our way to the game room and played some pool, as was one of our favorite things to do together, until we heard Hannah's voice call from upstairs that the food had arrived. When we made our way back up to the kitchen we saw the spread, and Annie hadn't been lying. There had to have been at least six pizzas, a couple of orders of bread sticks, some cheese bread, and some sort of cinnamon treat. Garret grabbed a handful of plates and told everyone to help themselves, which we happily did.

As we ate in the living room we all chatted some more, mostly discussing movies, and just had a good time together. So far the night was shaping up be exactly what we had wanted it to be, and we couldn't be happier. Once we had our fill of pizza Annie suggested we play the game we had all agreed on earlier. I pulled it back out of our bag, having put it away earlier to keep it out of the way, and we all made our way to the dining area. The table that Garret had in the dining room could easily sit over a dozen people it seemed, and I wondered who was renting a place like this that needed that much space. We all sat down around the table next to our respective partners.

"Alright," I said as I opened the box and handed Alex the cards to shuffle "we're going to need some paper and writing utensils."

"Got you covered." Garret said as he stood up and walked into another room. When he emerged once more he had a spiral notebook in one hand and a fistful of pens in the other. He sat back down, tore us each a page of the notebook and laid out the pens for everyone to take their pick.

"Rules of the game are pretty simple: we go in order drawing a card, then you'll write down your guess for what you think your partner will say and your own answer for the question. If a couple both get their partner's answer correct they get a point." I said once everyone had gathered their supplies. "Any questions?"

"What's the score to win?" Jason asked.

"Ten." I replied. "But I'll make an exception for you and Hannah and set you guys to needing 50. Everyone agree?"

The table all laughed, and we were ready to go.

It was interesting seeing how much we all knew about our partners, especially when the questions were less mundane and more sexual. Annie and Nate clearly didn't discuss sex as much as they just had it, as things like "what is your partner's favorite sexual position?" they both got wrong. Even on some of the more mundane questions couples were struggling, but nobody was getting mad about it, thankfully.

Then came the question that would change the entire evening. The card drawn asked very simply "how many people has your partner had sex with?" Everyone wrote down their answers, and we started going around the table to see if we were right. When I came to me I revealed seven for Alex, which she corrected to only six and I realized I had misremembered the one guy she had dated for a while but never ended up sleeping with. Then Alex told the table her answer for me: one. Garret seemed surprised.

"She's correct." I said.

"Really?" Garret asked, almost amazed by the answer. "You were a virgin when the two of you met?"

I nodded.

"How?" Isabella asked. Not in a judgmental way, but genuinely curious.

"I've always been socially awkward. And in my youth I was determined to prove I was better than other guys and always heard girls talk about how men were pigs who only wanted to get laid, so I made it a point to never push it. Of course, I was also oblivious to the signs when girls did want to sleep with me, which bit me in the ass more than a few times."

"And this didn't bother you?" Isabella now turned her attention to my wife.

"I was surprised at first, wasn't sure how a cute guy like him could still be a virgin. I think if we had met basically any other way I would have thought he was just out looking for sex."

"How long were you two together before you finally slept together?" Garret asked.

"About a month." Alex replied.

"So you've only ever had sex with Alex?" Garret asked me.

"Yeah, she's the only woman I've ever been with." There was no shame in my voice, nor should there have been. I loved my wife, and if she was the only woman I ever knew intimately I wasn't going to complain. We had discussed, while we were dating, maybe seeing if I could sleep with someone else to get some comparison, but I was happy with what we had going and nothing ever came of it.

"Interesting." Garret said quietly. "Sorry, didn't mean to derail the game. Shall we continue?"

And so we did, with the game eventually ending in a victory for May and David. After we had packed the game up we all made our way back to the living room, chatting and drinking as we had been before. Probably half an hour or so into our chatting, Garret stood up and looked at me with a devious look on his face. It was slightly distressing at first, but then he blindsided all of us.

"I have a proposal to make." He said.

"What kind of proposal?" May inquired.

"I'm glad you asked, May. Tyler, I can't get it out my mind that you've only been with one woman your whole life."

I shot him something of a glare, my eyes narrowing a little at what I perceived as a slight against me.

"I don't say that to be disparaging," Garret said with a calming hand gesture "but it is interesting. Most people who get past high school with their virginity in tact are the hyper religious type, and judging by how you swear and drink I'm going to assume that wasn't a factor in your youth. But I want to make you and offer."

Everyone seemed a bit confused, and for a moment I was wondering if he was going to try and offer me Isabella in a scummy sort of way.

"More accurately, this offer is for you two." He continued with a sweeping gesture towards May and Hannah, who sat side by side on one of the couches between their husbands. "I am prepared to make you a generous financial offer to give our friend here some more exposure."

"What the fuck does that mean?" Hannah asked, more confused than upset.

"If one of you goes upstairs right now with Tyler and has sex with him, I will give you both fifty thousand dollars."

The room went silent. I expected Jason to get up and punch Garret right then and there. Despite his jokes and laid back demeanor, he was fiercely protective of his wife, and I'd seen him lose his cool over lesser words.

"What?" May's voice finally broke the silence.

"I'm prepared to sweeten to pot as well," Garret said after taking a sip of his drink "if you let him cum inside you I'll double it."

One of the three sisters went to offer some retort, but Garret cut her off. "And I'll go even better if you both go with him. Five hundred thousand if you both go upstairs right now and show your brother in law a good time."

"Garret, that's enough." Nate chimed in, as the rest of us seemed completely speechless. "This joke has stopped being funny."

"It's no joke, my friend." Garret said. "I'm dead serious. And if you girls both go upstairs with him and let him experience a woman other than his lovely wife, and one of you lets him cum inside you: I'll give you each a million dollars."

"Now we know it's a joke." David said. The number was so ridiculous, and to offer it to three complete strangers to have sex with each other? It made almost no sense. The tension left the room a little and we all waited for Garret to laugh to let us know he really was kidding.

The laugh never came.

"One million dollars to the three of you, I can make it happen." Garret said, his tone more serious than before.

"He can," Annie said "he's got that kind of money."

I continued to be surprised when none of the three of us guys got up and decked Garret, and equally surprised that neither May nor Alex, as Hannah was less inclined to such acts of violence, didn't leap up to hit him either. Instead there was just an awkward silence that filled the room, only broken by the sound of Isabella sipping at her glass of wine.

What he was offering was crazy. I'd be a liar if I said May and Hannah weren't attractive woman. Alex and I had even talked about it before, and I had, in the past, masturbated about them both a handful of times. I loved Alex, and the sex was great, but sometimes you get someone in your head and you just need to get the release so you can move on. I'd never forgive myself if I had slept with Alex and had images of either of her sisters in my mind. Someone rubbing one out about one of them seemed more innocent, for lack of a better word. But the idea of actually sleeping with either of them? Never crossed my mind. Not only were all three of us happily married, but it just seemed completely out of the realm of possibility.

What happened next blew everyone away a little.

"Can we talk with our spouses real quick?" Alex asked.

"Of course!" Garret said with another hand gesture.

The three couples broke off to our own little corners and began to talk among ourselves.

"This is insane." I said.

"Yeah," Alex agreed "but I'm wondering if we should maybe hear him out."

"What?!" I said, almost a touch too loud. I was shocked she would say something like that given the situation.

"It's weird, yeah, but listen to me on this, okay? We'd talked in the past about you sleeping with someone else just to have some more worldly experience-"

"When we were dating," I cut her off "but we're married now. We have a kid, Alex."

She raised her hands up, palms out to calm me down. "Yes, but just let me finish."

I took a deep breath, and nodded.

"We talked about you getting some more experience. May or Hannah might be a good option. We know their both happily married as well, so there's no risk of people getting divorced over this and running off with their former in-laws. Plus, and let's be real this is the biggest factor, fifty grand is life changing money right now. We could pay off the rest of my medical bills, our credit card debt and still have some left over to put into savings. We could be debt free for the first time in years."

"And all it would take me is me fucking one of your sisters." I said.

"A price I never would have considered before tonight, but the offer is in front of us."

I wasn't sure how to feel about her saying this. Her sisters were attractive, yes, but this whole scenario still seemed insane.

"I think we girls need to talk." May said, referring to her and her sisters.

"Let me talk to them, I'm sure they'll both say no and we can maybe just all go home and act like this never happened." Alex said.

"Okay, do what you guys have gotta do."

Alex and her sisters walked to the far side of the house, away from listening ears, and the husbands found ourselves also gathering together. We stood in silence for a moment, the three of us moving our gazes from our wives to Garret who seemed perfectly content to wait out an answer. Annie and Nate sat together, talking quietly and looking between the trios of husbands and wives. It was all surreal, and again nobody had resorted to violence. Nothing was said between David, Jason and myself. What would we even say?

The girls walked back over, together and stopped a few paces away from Garret.

"If you need to discuss with your spouses again by all means, I won't stop you." Garret said.

And so we broke off into our respective pairs again. And I was completely unprepared for what Alex was going to tell me.

"So, me and the girls agree that while this is all odd as hell, it's an offer too good to turn down."

"So which of them agreed to this madness?"

"Both."

I was stunned. I expected one of them to offer to take one for the team at best, but not both of them.

"You mean I'm going to-"

"Have a threesome with my sisters? Yeah. And, we also agreed to bring it to you guys about meeting the final condition."

"You mean me cumming inside one of them?"

Alex nodded. She clearly wasn't thrilled about the idea herself, but their discussion must have made them all come to the same conclusion: that it would be worth any awkwardness.

"Think, Tyler. A million dollars? We could pay off all our debt, put some into savings and still have money left over for a damn good down payment on a house. We could finally own a home. We could be on the path to better lives."

All at the expense of me having sex with her sisters, I didn't say out loud.

"And one of them agreed to a creampie?"

"After I reminded them of your vasectomy, it seemed like something to consider. It wasn't an easy decision by any means, but we could all change our lives with that kind of money. And with no risk of pregnancy..." she didn't finish her sentence, but I knew where she was going.

It all seemed so surreal to me. The fact they had even considered it to begin with, but to offer one of them up for something that seemed so intimate? But I trusted Alex, and I trusted her sisters. They were smart, and if even one of them had wholly objected then this entire conversation wouldn't have been happening.

"That being said," she said after a moment "this all rests on you guys."

I looked around the house to see the other two couples still in their own conversations, but I saw Jason nodding to whatever Hannah was saying to him. His arms were across his chest, and he didn't look particularly pleased at this whole thing, but Alex was right: that kind of money was a game changer. Even if David or Jason didn't agree to the creampie thing, if they agreed to the threesome then half a million bucks was hard to argue with.

"If you're uncomfortable with any of this, you say the word, we grab our shit and we go home." Alex said softly, placing a hand on my shoulder in a reassuring manner. I put my hand over hers and looked into her eyes. The idea wasn't ideal, but we both knew that it was too good to turn down.

"This whole thing is uncomfortable," I said "but you're right. Any amount he's offering would totally change our world. I don't love the idea of sleeping with your sisters, but getting out of debt is too good to pass up."

"On the bright side, at least my sisters are hot. Could be way worse." She said with a light chuckle, her laugh pulling one form me as well. "So, we agree to whatever decision David and Jason make?"

I nodded.

May called Alex and Hannah over, they chatted very briefly relaying the news of their husband's decisions. I walked over and stood with Jason and David again, expecting them to hate me in this moment. But neither seemed upset with me, although all three of us were a tad upset with Garret. Even if we were willing to take him up on one of his deals, who the hell makes that sort of offer to complete strangers?

"We've come to a decision." May said. "After discussing among ourselves and with our husbands, we agree to the terms."

"Excellent!" Garret said, a tough too much glee in his voice. "And which decision have you all come to?"

Annie went to protest, but May waved away her words.

"You're offering a million dollars, and we're prepared to accept." May said.

I turned and looked at David and Jason. Jason still looked annoyed, and gave little heed to my expression. David, meanwhile, looked at me and gave a shrug.

"It's a lot of money," he said "even if we're not thrilled with the means of getting it. No offense."

"None taken." I said.

"Same situation here. It's not ideal, but at least I know I can trust you." Jason said. "But once we have that million in our bank account I'm finding this guy and beating the shit out of him."

I stifled a laugh, and David smirked. I had expected Jason to put up the most fight, to outright decline the whole thing, to tell Hannah they were leaving. David and May were pragmatists, so while still a little surprised at them agreeing to it, of the two couples they made the most sense. Jason was protective of Hannah, I had seen him nearly come to blows with a friend of his at a backyard barbecue when they had made a crude remark about Hannah's breasts since having their kid. The fact he agreed to any of this was amazing, but by the end of it all I wouldn't be complaining.

"A threesome with a happy ending. I must say, I'm surprised you all came to this agreement, but I'm a man of my word and will pay accordingly." Garret's voice broke my concentration and drew me back to the discussion at hand. "I do have just three small stipulations."

"Stipulations?" Alex asked, ire in her voice at him adding more to this.

"I'm offering a lot of money here, I think I'm entirely within my right to have terms. If any of them are not agreeable then you can back out, I'm not unreasonable."

"And what are these stipulations, exactly?" I chimed in, noting the annoyance in my own voice. "Because I feel like you could have mentioned these before we discussed all this."

"Probably," Garret said "but I've always had bad timing. Firstly: each participant must both give and receive oral sex. I know some people try to skimp on that. Second: each of you ladies must be pleasured in a minimum of three positions. Tyler, I trust you have your cell phone?"

"I do," I replied "what of it?"

Garret grinned a little, it actually made me a tad uneasy. What did he want with my phone?

"My third stipulation is this: you must record each act for at least thirty seconds. Each instance of oral, and each position."

"What?" Hannah said.

"Again, I'm offering a lot of money here. It'd be far too easy for the three of you to go upstairs, rattle and bed and fake some moans and claim to have done the deed. If I'm going to give you all a million dollars I don't think it's entirely unreasonable to expect some proof."

"You fucking pervert." Jason growled. "You plan to jerk off to it later?"

"Not at all," Garret replied, shrugging off the insult "I simply want visual confirmation and then you can delete the footage forever."

I looked over to the girls, who leaned in and whispered among themselves for a moment. "Fine." Said Alex, surprisingly.

Garret smiled again, and then turned to look at me. "Tyler, may I see you in the kitchen?"

I nodded and followed him out of the main area and into the kitchen. Boxes of half eaten pizzas littered the counters, empty beer and wine bottles, partially consumed bottles of vodka and gin sat together. He reached into a cabinet and grabbed a small glass, filling it with water at the sink. He turned and walked over to me, having put his own drink on the counter when we entered, and reached into his pocket. He pulled out a small package, the kind single doses of pills come in. He held his hand palm up with the packet and a pill clearly visible.

"What's this?" I asked, more confused than angry in the moment.

"What I'm asking is a tad unorthodox," he said "this is to help with any possible performance issues. Despite those two being attractive women, they are your sisters in law, and I understand that may cause problems."

"Enhancement?"

"Nothing insane, just to help you rise to the occasion."

I took the packet from his hand, tearing into it and popping the pill into my mouth before taking the offered glass of water and washing it down. I put the glass on the counter and stared into Garret's eyes. He had a point, if I was going to do this I couldn't risk not getting hard. Pissing away a million bucks because I couldn't get it up? That'd be the single most embarrassing thing to ever happen to me.

"Why are you doing this?" I asked.

"Because I think you should know the pleasure more than one woman. I'll be honest, I didn't expect any of you to actually accept. I was ready to play the whole thing off as a joke, blame it on the booze and let it go. The fact you all agreed to it caught me a little off guard."

"Why is it so wrong I've only slept with my wife? What the fuck is so bad about that?"

"Nothing," Garret replied "but I saw a chance and took it. Hell, taking chances is how I got to where I am today. I'll be honest, if I thought I could convince Annie to be the one to go with you I'd have gone with that angle. But she's a touch too prudish I think, and her and Nate are plenty well off enough."

"Look who's talking." I scoffed.

"That's true. I am well off in life, and while I know your sisters in law are as well, I know that you all have kids and debts and that any sizable amount of money could go a long way for you all."

I wasn't sure how to feel about his logic, but it was sound. Alex and I had often found ourselves wondering how we would raise our daughter in an apartment as we saw our hopes of owning a house dwindle every year with an ever more fucked housing market.

"Even David and May," he said "they may the best off of you all, but if their house burned down they'd have to deal with all the bullshit and hassle of finding a new home. Nate and Annie? They could just move into one of Nate's other seven houses with basically no effort on their part. You guys can actually use this kind of money for the better, even if I will admit I wouldn't be opposed to seeing video footage of Annie getting some."

I didn't comment on that last part. Annie wasn't ugly by any means, so I could get where he was coming from there. Hell, he had made good points overall, even if his means to getting us the money were odd and completely out of left field.

"Why did you have that pill if this was all spur of the moment?" I asked, the realization dawning on me.

"Well, I suspect Isabella and myself will have some fun of our own, and I have been known to suffer from performance issues, so I always keep at least one handy."

His answer was surprisingly candid, but I suppose he was never going to see me after this whole situation so what did he care?

"Now go, don't want to keep May and Hannah waiting."

I nodded and walked out of the kitchen to see the girls, along with David and Jason, standing together in a group. I was sure everyone downstairs would have words for Garret while we were off doing the deed, but hopefully nothing that would cost us the money. As hot as May and Hannah may have been, not getting the promised payout after fucking them would make the whole thing even more weird.

I walked over to join them, and Alex kissed me and gave a reassuring smile. I knew she wasn't thrilled with this, but we both knew that it would ultimately be for the better.

"At the top of the stairs, if you turn left and go all the way down the hallway there's a bedroom for you to use. It's the best option."

"Why is that?" Hannah asked.

"Because it's position in the house means we shouldn't be able to hear anything." Garret replied.

"Well," I started, gesturing towards that stairs "should we get this over with?"

Hannah and May both nodded and the three of us made our way to the steps after kissing our respective spouses once more. As we walked up the stairs May took the lead, I was behind her and Hannah pulling up the rear. Given all that was going on, it should be no surprise that my brain took notice of May's ass. Her jeans hugged her hips, and the denim really accentuated her buttocks in a way that made it near impossible to not stare considering she was just far enough ahead of me that her ass was eye level. It made me wonder if Hannah was looking at my ass, although I doubted it even given the situation.

We followed Garret's instructions and found ourselves in a large bedroom at the end of the hallway. A reclining chair sat in one corner, a king sized bed in the middle with the headboard practically touching the wall, a large shelf full of various kitsch from god knows where along the wall directly to our left upon entering, some paintings hanging on walls and a TV mounted on the wall directly across from the bed. If it hadn't been for all the shit on the shelf and the ornateness of the paintings and size of the TV it would seem like a fairly unassuming room all told.

We closed the door behind us and May took a step ahead and turned to face Hannah and I.

"Okay," she said "if we're going to do this then we need to lay down some ground rules. First, I think kissing is out."

"Agreed." Hannah and I said in unison. Sex was one thing, but kissing just seemed so personal and romantic.

"The next thing," May said as she slipped her wedding ring off her finger and held her hand palm up with the metal circle in the center "give me your rings."

"What? Why?" Hannah asked.

"Because for the sake of making this work we have to not have constant reminders of our spouses downstairs. For the next however long this takes, the three of us are single. It'll at least lessen the weirdness a touch."

She was right, and I agreed with her as I pulled my own ring off and placed it in her hand. Hannah stood for a moment, futzing with her own ring before nodding and taking it off. With the three rings in hand May walked over to the shelf and placed them down with a light clink.

"Now, let's all just take a deep breathe and remember that this is for the best."

We all breathed deep together, exhaling at the same time to try and shake our nerves. The realization of what was about to happen had hit me, as well as the pill that Garret had given me. These two were both very attractive, so I wasn't sure if the pill actually did anything, but I chose to believe it was for the sake of feeling a little less unfaithful to Alex in the moment.

"The most important thing is this: we're doing this, and it'll be a little weird at first, but ultimately while this isn't the ideal way for all of us to change our lives we might as well try and enjoy ourselves."

May was right. If we continued to focus on it being weird and awkward, then it'd always be just that. If we just let go a little and had some fun, maybe this whole situation could at least be enjoyable.

"Not to sound crass, but which of you wants the creampie?" I asked.

"May will be getting that honor." Hannah said.

I looked to May quizzically. I honestly thought it would be Hannah, as May was always the most prudish of the three.

"It's basic logic. I live far away, we don't see each other that often, and by the next time I'm in town maybe any lingering weirdness will have faded."

She made a good point. Her and her family only came to town once or twice a year, and while Alex and I had been out to Boston to visit them it was a rare trip indeed. Hannah, on the other hand, lived less than half an hour away from us, and we spent many weekends hanging out at their house, especially during the warmer grilling seasons. Seeing Hannah that often knowing I had fucked her would be uncomfortable enough for a bit, but knowing I had shot a load inside her would just amplify that ten fold at least.

"So, the real question is this: how do we get this started?" Hannah asked as she stepped past me to stand next to her sister. They both turned to face me like I had an answer.

May was fairly tall, with a somewhat athletic build. She had been hellbent on staying in shape as much as she could after having her kid, and she had a fairly toned body with perky breasts. She had wide hips and a surprisingly full ass, combined with long runners legs she was quite the treat. She had a slightly angular face with with long brown hair that came down to her chest. She was quite the looker, especially for a mom creeping up on 45, she kept in good shape and took good care of herself. I had seen her in swimsuits before and always appreciated the view, but never thought I'd actually see her naked.

Hannah was almost the opposite of her sister. She was fuller bodied, with a bit of a belly and curves for days. She had plump B cup tits that had filled in since becoming a mom. Her face was much rounder and she had dirty blonde hair she often kept in a messy bun. Like her sister she had wide hips, and her ass was on the good side of big without being disturbingly big. She had thick cellulite thighs, but all her fullness came together in the right way. What extra weight she did have she carried well, and I wouldn't describe her as fat by any means. I had seen her in many swimsuits over the years as well, Alex and I had spent a couple summers at her old apartment hanging out at the pool with her and I'll admit it had sometimes been hard to hide the boners she could induce.

Both girls wore jeans that looked good on them. May's were flared at the bottom, and Hannah's were faded and torn exposing some of her legs underneath. Hannah wore a shirt that I can only describe as the color of dijon mustard, with a slight V cut at the neck that didn't plunge super far, but did afford a nice little peek if she bent over just right. The top of her bra cups pressed against the somewhat thing material of her shirt, hiding very little from sight. May's shit was likewise fairly thin material and gave a hint of the bra underneath, with three quarter length sleeves in a lovely purple that cut just low enough to expose her collarbone.

Speaking of hiding boners, there was basically no hiding the one pushed at the fabric of my pants now. Knowing that this was happening made me rock hard, and there was nothing I could do about that.

"Should we start just all masturbating together?" Hannah asked.

"I dunno," May said "that seems a little weird."

"Well, we know someone who doesn't seem to need any help." Hannah said with a smile and pointed to my crotch.

May looked down and her eyes went wide, and as she raised her head to make eye contact with me a smirk sat on her face. "Already, huh?"

"Garret gave me something to help with any performance anxiety." I said. It was mostly a lie, I was convinced the pill had nothing to do with how erect I was. I was nervous, for sure, but I was also about to have a threesome with two beautiful sisters. Most guys would kill to be where I was. "How about this, why don't I grope you guys a little. See what we can do to get your engines going."

The girls looked at each other and then back to me.

"Worth a shot," Hannah said "you have free reign."

I took a slight step forward, until I was in easy arm reach of both of them. Hannah stood on my right, May on my left near the shelf. I too a breath, and reached out. I started fairly innocently running my hands along their bodies, feeling the differences in their stomachs, running my hands along their sides, down to their hips and past that to their thighs. Both girls seemed into it, neither shying away from my touch. With this knowledge I grew a little bolder, pushing my hands up their bodies and cupping their breasts in my hands. I gave each of them a squeeze, being met with giggles from the girls as I groped their chests. Hannah had more give than her sister, but both felt good in my hand thus far. I let my hands wander and explore, at one point groping one of Hannah's breasts to a soft moan while my other hand slid down between May's legs and pressed against her crotch. She let out a little gasp at the touch, but she didn't tell me to stop. Eventually my other hand wandered south on Hannah, and soon both my hands were groping at their crotches.

"This doing anything for you two?" I asked.

"Oh yeah," Hannah said quietly "it's doing good stuff."

Then I felt May's hand on my own crotch, rubbing at the throbbing erection in my pants. I gasped a little at the unexpected touch, but my cock reacted to it in a way that May clearly found favorable.

"Do you think Hannah should suck you off?" She asked me as she rubbed at my crotch.

All I could do was nod.

"Then get out your phone, gotta make sure we get this on video."

I reached into my pocket and pulled out my phone, opening the camera app as Hannah lowered herself down onto her knees in front of me and began to work at my belt. Quickly she had that undone and had the button on my pants popped and was slowly unzipping my pants. May lowered herself down next to her sister at that moment, wanting to be at the best view for the reveal. Once the zipper was past a certain point my cock sprung up through the hole in my boxers, getting excited sounds from both of them.

I'm no super stud, not hung like a horse or anything like that. I've always been on a chubbier side, and at full mast I clock in just over six inches. I'm totally unremarkable in that regard, but neither May nor Hannah seemed bothered by it. I had had a discussion with Jason once and he had told me he was about six inches, and so I was sure my size would work for Hannah. May I wasn't so sure about. I always assumed David was pretty well endowed, but she showed no signs of disappointment or anything like that.

I hit the record button on my phone as Hannah reached a hand up an began to stroke me, I moaned as her hand touched my skin and began to slide along my cock. It took a lot of concentration to keep the girls in frame as she did so, and she knew how to jerk a guy off quite well. Good speed, motion and little applications of pressure as her hand moved up and down on my shaft. Then, as her hand moved from the head down I felt the warmth of her breath before her soft lips enveloped the head of my cock. I moaned again, louder as I felt her mouth slide further down my throbbing mass, following her hand. She got most of it, I'd say probably a good four inches, into her throat before sliding back up. I couldn't believe my sister in law was on her knees sucking me off, but god damn did it feel good. I saw her glance up at me at one point, her eyes smiling and that round face gliding along my dick with ease.

As Hannah slid her head back and forth on my cock, I felt May's hand slide up the loose leg of my boxers and her slender fingers made contact and started to fondle my balls. I moaned again, not entirely sure the two of them weren't going to make me blow my load right then and there. Then May pulled her hand out on my underwear, and with a smile she reached down, grabbed her own shirt and lifted it up and over her head. She wore a semi lace black bra that did wonders for her, and even from the angle I was at I could see that lovely toned tummy of hers. At least I could when I could keep my eyes open as Hannah continued sucking my cock like a champion. Then I watched, through the screen on my phone, as May reached behind her back and undid her bra, letting it slide forward and pulling it off of her. She had beautiful retrousse breasts, and due to their smaller size they had just the perfect amount of sag that allowed her light nipples to point up at a pleasant angle. I felt my cock throb in Hannah's mouth as I took in the sight of May's tits, and Hannah moaned around me as she continued to blow me.

Soon Hannah pulled me free of her mouth, letting out a satisfied "ahh" like one might hear after taking a refreshing drink of water.

"Was she good?" May asked.

"Very." I said, watching as Hannah licked her lips.

"Well then I guess it's my turn. But let's get all this out of the way."

"Wait," Hannah said "when did you get topless?"

May laughed a little at the fact that Hannah had been so lost in giving me head that she hadn't noticed her sister stripping down right next to her. Then, at May''s behest, the girls helps me step out of my own pants, and May grabbed my boxers and gave them a good tug to pull them down before I stepped out of those as well. Now I stood before them, nothing hiding from the waist down, with Hannah's saliva still on my cock and May sitting topless before me.

May reached up her own hand and gave her a few strokes, then she put both of her hands on my waist and leaned forward. She stuck out her tongue and ran it up the length of my cock, from the base to the tip of the head. With tongue still out she used it to guide my cock right down her throat as she slid her head down towards my pelvis. Likewise, she managed about four inches of me in her mouth before her head started to slide back and forth on me. Hannah had let her tongue get involved a little, but May was using it to her advantage. I could feel it along the bottom of my shaft as she glided her mouth along me in the most pleasurable ways. She pulled me from her mouth, held my cock in her hand and ran her tongue up and down the length of it before looking over to her younger sister who watched, almost entranced.

"Hey," she said, snapping Hannah's attention for a moment "get that shirt off. Let Tyler see what you're packing!" And with that her soft lips wrapped around my cock again and she moaned as she took every last bit of me she could into her mouth.

Hannah looked up at me with a smile as she listened to May moan and suck. "You want to see my tits?"

"God, yes." I moaned as I felt May's tongue wiggle against my cock in her mouth.

Hannah wasted no time in taking off her shirt and tossing it across the room with a giggle. The bra that held her breasts was a medium blue with pink accents that really caught the eye, but I didn't have long to take in the pattern on it before she had unhooked it, slid it off and tossed it off with her shirt. Her fuller body now on display, the curves, the perfect bit of pudge to her stomach, and those round, full B cup tits with beautiful hard nipples. They sagged just a little bit, but not too much, and they looked even softer than my groping through shirts would imply. I had seen Hannah in bikinis many a times, I had gone to concerts and the likes with her and seen her dance around. I knew how bouncy her breasts could be before she had her son, and now I wanted to know how much better they moved after growing a tad bit.

But the girls, apparently, still weren't done with the oral just yet. When May ended her first go she, more or less, handed me off to Hannah who wasted no time taking me back into her mouth. May reached up and took my phone from me, getting a full profile shot of her sister sucking me off. Hannah had one hand on my cock, gliding along it with her mouth, and now the other reached up and began to grope my exposed balls. Both hands and her mouth working to make me feel good, and it sure did feel good. Then the girls switched again, Hannah taking my phone and getting a profile view of May as she pushed to take every inch of me down her throat that she could, likewise reaching up with one hand and fondling my balls with her slender fingers, juggling them between her digits as she let her lips and tongue work miracles.

Hannah stopped the recording, which had been going on for well past the thirty seconds Garret required of us, and tossed the phone onto the bed. May pulled me from her mouth, but kept playing with my testicles while Hannah reached up and began to stroke my saliva coated cock again.

"You know, I believe it's time that we got our fun. Don't you?" Hannah asked.

"I must agree. And the rules do state he needs to eat us out, don't they?"

"Well," I said between moans "I wouldn't want to break the rules. But that means we need to get you ladies out of your pants."

Both sisters let go of me and stood up, now standing before me in their topless glory and letting me get a real good look at their breasts. I wanted to reach my hands out and play with them, or lean forward and take one into my mouth, but I knew there would be time for that. In the moment I want to get their pants off, and I wanted to know their tastes.

They gently guided me back until I was sitting on the edge of the bed, and without prompt I removed my own shirt to be the first one naked of us. The girls stood before me, Hannah now on my left and May on my right.

"So," May said "how do we want to do this?"

"Turn this way," I said, gesturing for them to face me "and I'll get you girls out of those jeans."

They both laughed a little and turned to face me, and I started working at Hannah's pants. She wore no belt, so it was straight to the button, and once that was done I was able to slid her zipper down with ease. I hooked my fingers into her belt loops and tugged at her jeans. She had to reach down and help, wiggling her hips a little to get the fabric off of her. She wore a pair of cute tie-dye panties that took me a bit by surprise, but they gripped her hips well.

I then turned my attention to May, getting her belt undone as quickly as I could. The button and zipper of her jeans put up little resistance, and soon I was pulling the denim off her wide hips and exposing the partially lace black panties that matched her bra. Once she had stepped out her her jeans, playfully kicking them to the corner of the room, I had them both turn around so I could get a good look at their asses.

May's ass was a little tighter, but still pleasantly shaped. Hannah had a much fuller ass, but it was lovely. I slid my fingers into the waistband of Hannah's panties and pulled them off her ample rump, getting a full view of that spectacular ass. I knew she was a little self conscious of it, having mentioned that she disliked how big it was sometimes, but I found It perfect for her body. Her ass and thighs both thick and spectacular. Then I turned to May, gripping her panties the same way and yanking them down. While her ass wasn't as big as her sister's, it was still surprisingly full given the rest of her body. A firm bubble butt greeted me as her panties slid down, and I spent a moment admiring the view I had of both of them.

I raised my hands at the same time, and then gave them both a good slap and squeeze. Hannah's ass had more give, as I suspected, but both of them felt wonderful in my hands. Both girls let out a little squeal of delight as my hands made contact with their skins, and Hannah uttered an "oh!" as I gave their buttocks good firm gropes. I reached over and grabbed the phone, starting up a new recording, and then gave them each another spank on video, noting the difference in how their skin moved.. Hannah's ass jiggled with the impact, and May's stayed much more stationary, although with a little ripple along her smooth skin.

Then came the moment I really wanted on film. I had them both turn around to face me again, getting my first real looks at them in all their naked glory, from their beautiful breasts and lovely bodies, their faces, and finally their pussies.

May was completely bald, as I knew she was. She and Alex had talked about shaving, and May had made it very clear that she was totally shaved because she hated having pubic hair. But even knowing that beforehand couldn't prepare me for the sight. Totally bald, with pink lips nestled between her muscular thighs.

Hannah, on the other hand, was shaved, but not bald. She kept her hair well trimmed and managed, a short tangle of dark blonde hair in a triangular shape that pointed right to her cunt. Lovely lips peeking out from the hair and her cellulite filled thighs.

My cock throbbed relentlessly at the sight of the two of them. There they just stood, right in front of me, not a bit of clothing on them expect for their glasses. I let my eyes wander up and down each of them a couple of times, really taking it in, my cock dying for some attention in the moment as their sexiness overwhelmed me a little.

"You like?" Hannah asked.

I nodded. They were more stunning that my imagination could have ever come up with. Two sexy women, absolutely embodying the term MILF.

"Hannah, take the phone." May said. Once she had taken the phone form my grip May looked down at me. "And you, lie down."

I did as I was told, settling my head onto the pillows on the bed. Hannah came around the far side of the bed, now sitting on my right side as I lay there, my cock at full attention and waiting for what was coming. Then May climbed up on the bed, and with a smile she proceeded to lift one leg up and over my head, straddling me as she hovered her beautiful bald cunt just inches from my face. Her aroma wafted over me, and I could see how wet she had gotten.

"You recording?" May asked her sister.

"Sure am." Hannah replied.

"Good. Now Alex has made mention of your skill with your tongue, and now is you chance to show me if her claims are true at all. You ready?"

"Just bring that sweet pussy down to me and I'll show you how right she is."

I saw May waggle her body a little, and then with a "prove it" she lowered herself down. Her pussy made contact with my mouth and she let out a gasp, followed by a moan and an "oh god" as I let my tongue loose on her. She tasted sweet, and I lapped at her juices and put my tongue to work on her clit. I moved it all over her crotch, from her clit to licking her lips to pushing it between her warm pink slits and probing inside her snatch. She moaned loudly, reaching a hand down and grabbing a handful of my hair. My own hands were wrapped around her legs and holding onto her toned thighs as I ate her out. She gently bucked her hips a little, her body reacting to the touch of my tongue, and I would adjust accordingly to keep getting a taste of her. Eventually I adjusted my arms and moved my hands up her body, sliding them along her toned stomach, feeling it move against my touch as she gave into the pleasure, and finally up to her chest where I grabbed hold of her lovely pert breasts. I squeezed them as my tongue ran laps around her clit, I gently pinched and tugged at her nipples as I felt her juices saturate my tongue. I listened to her moan and gasp, I felt her as she pressed her pussy against my mouth harder, I heard her say things like "right there," "keep licking" and "Alex wasn't lying" between moans. I felt the distinct sensation as her other arm reached back and she gave my cock a good couple of strokes.

"Oh fuck!" She moaned at one point as my tongue pressed hard against her clit. "Right there! Keep doing that! For the love of god do not stop!"

I obeyed, giving her breasts one more good squeeze that elicited a soft moan before bringing my hands back down and grabbing her nice wide hips. I kept licking how she told me to, listening to her breathing getting harder and faster. She had taken her hand off my cock, still gripping my hair with her other and saying "just like that, just like that!" I kept going, she pressed her snatch against my tongue more, her breathing grew short and quick, and I heard her say "oh god, Tyler, make me cum!"

With one more hard lick I felt her body contract and buck, and she moaned louder than she had at anything else thus far. I heard her other hand slam against the wall as she slumped forward, panting and moaning. I let my tongue take another quick lick which made her shiver and moan before I climbed off me.

With my vision no longer obscured by her amazing legs, I could see Hannah sitting there on the bed, her legs open, holding the phone and having filmed the entire thing. I looked straight down at her pussy, beautiful pink lips slightly spread and glistening. Watching her sister ride my face must have gotten her pretty wet, and having now tasted May I had to know how delicious Hannah was as well.

"May, take the camera." I said. She reached a hand out and took the phone from Hannah. I got up, walked to the foot of the bed, grabbed Hannah by the ankles and, with a gleeful little scream, dragged her to the foot on the bed until her legs were hanging over the side. I dropped down to one knee and pushed her legs apart to get another good look at her.

"He's that good, huh?" Hannah asked.

"Oh yeah. Alex is definitely getting a good deal here." May replied as she caught her breath. "Ready when you are." She said, clearly directly at me.

"I'm ready." I said, and I leaned forward until my mouth made contact with Hannah's soft pink folds.

She tasted sweet as well, and hr whole body jerked a little as my tongue darted out of my mouth and took a good taste of her. She moaned as I ran it all along her lips, one hand grabbing one of her nice thick thighs, the other resting on her soft belly. I listened to her moan as my tongue explored, savoring her taste and flicking at her clit playfully. I tried all sorts of things, seeing what reactions they got from her, and while all seemed to be enjoyable there were absolutely ones that made her moan louder than the others. One was circling my tongue along her clit, rolling it on my tongue. As I did she I could feel her back arch, and at one point between moans and gasps I heard her simply say "finger me while you eat me."

I moved my hand down from her stomach, and not wanting to disappoint, I slid my middle finger between her lips as my tongue worked her clit. I felt her wetness on my digit, I could feel the juices rolling down my hand and to my wrist, and once I was certain she was welcoming my finger I added my ring finger as well, pushing knuckle deep into her beautiful MILF pussy. She moaned louder as my fingers moved inside her, hitting her G-spot as my tongue continued to pleasure her clit.

"Fuck me, that's good shit." She moaned, and I kept doing exactly what I had been.

Then I heard the sound of May getting off the bed, and I could feel her behind me. She knelt down, and while I couldn't see her as my eyes were closed in ecstasy and I was focused on devouring Hannah's pussy, I did feel her body gently against mine. Then I felt her hand wrap around my cock once more. I moaned into Hannah's cunt as her older sister began to jerk me off, and Hannah moaned louder as my fingers curled and hit her pleasure zones.

"Does she taste good?" I heard May whisper in my ear. I presumed, as I couldn't feel her other hand anywhere, that she was still filming while this was happening. "You like eating my little sister? You've eaten both of them now, tasted them on your tongue. You want to fuck her don't you?"

I moaned an affirmative as I kept doing what Hannah was enjoying.

"You can't fuck her yet. You need to make her cum like you made me cum. Once you do that you can fuck us both. Can you do that? Can you make her cum?"

I moaned again, continuing my efforts on Hannah, being met with moans from her and more verbal affirmation. She urged me to keep going, that she was so close, so I did. I kept licking and fingering her, listening to her moans and her voice as May stroked me faster and faster.

"Right there!" Hannah moaned. "Right there! I'm so fucking close!"

One more circle with my tongue, and one push with my fingers and Hannah was done. She moaned, practically screaming, and I felt her pussy contract around my fingers. As I pulled them free I felt a little ejection, a small squirt of fluids on my tongue that I savored. May let go of my throbbing cock and I could hear hr standing up.

As I got to my own feet I saw Hannah, panting, hands gripping the sheets and a smile on her face.

"Right?" May said.

"Holy fuck." Was all Hannah could reply.

They had little time for any other words, I was so caught up in the moment that I simply grabbed my cock, aimed and slid it into Hannah's waiting pussy. She moaned loudly, her eyes going wide as she felt my cock split her folds and push into her. She was still fairly tight, I knew all three of the sisters did their kegels so I wasn't entirely surprised, but it felt good pushing my way into her MILF cunt. It only took a couple of thrusts before I was balls deep inside her, her legs spread to either side of me as I felt her body grip me in pleasure. I began to thrust hard, but slow, slamming Hannah's pussy and making her moan with every impact. I watched her belly and her round tits jiggle with each thrust, listened to her moan, the sound of our bodies colliding as I fucked her. I didn't want to go too fast and risk blowing my load early, we needed to meet Garret's rules if we wanted our payout.

The view was quite lovely, her full, curvy, body on display, her tits jiggling as I slammed into her again and again. The feeling of her warm snatch taking in every inch of my cock as I slid in and out of her, pulling so far back with every motion that I practically popped out of her each time, only to then push all of me back into her wanting folds. Feeling my cock rubbing along the walls of her pussy, watching another bounce of her breasts. All the while May sat on the bed next to Hannah, moving the camera back and forth to get good shots of everything that was happening. I picked up the pace a little bit, but not too much, as watched as Hannah's belly and breasts moved with the action.

I felt her legs wrap around me as she pulled me tight, and she moved her hips with me as I fucked her more. It was almost like I was in a trance, unable to stop myself, and I just kept going and watching as her body reacted to mine. Eventually her legs let go of me, I grabbed her by the hips and gave her another couple of good, hard, thrusts that had her white knuckling the sheets once more.

"Okay, I gotta get a turn with that." May said. Without another word she handed the phone to Hannah, who struggled to keep her grip on it for a moment before rolling onto her side and watching as May took me by the hand. She walked me over to the wall next to the bed, pressing her back against it and lifting one leg. I put my hand on the underside of her thigh to offer some support, and then took a moment to just enjoy the view. Her fully exposed body now on display for me, and I wanted to savor every second of seeing her this way.

I squatted down, scooted forward and gave her pussy another good lick, tasting her again and letting my tongue flick against her clit to a gentle moan. Then I stood up, and got in closer. I never thought I'd actually get to have sex with May, let alone in this position right out of a porn video, but this was how she wanted it and we were here so I wasn't going to complain. She reached a hand down, and gently took hold of the throbbing mass that was my cock so she could guide me between her legs. She lowered herself down a little, and I shifted to accommodate. Our height difference wasn't that much, which made this a tad awkward, but damn it we were determined to make it work. With a little more readjusting we both gasped as I felt her wet lips open to take me inside her. We were able to get most of me inside her, and I moaned as I felt her pussy welcome me. She moaned as my cock brushed against her walls, and after a brief moment of getting used to each other I began to move my hips as much as I could, sliding in and out of her. I couldn't go particularly fast or hard in this position, but it felt amazing, and something about the angle we were at was clearly doing things for her as well. I moved my free hand up and groped one of her tits as I fucked her for the first time, squeezing as I pushed inside her again and again.

It felt incredible, but something about it felt oddly intimate. Maybe it was the fact we were face to face, maybe it was the fact we had to take it slow, but it felt personal somehow. If we hadn't agreed to the rule earlier I would have been tempted to kiss her right then, slip my tongue into her mouth as my cock slipped in and out of her pussy. We kept at this position for a minute or two, but I knew what I wanted and I felt like I was in a position to take it.

I pulled out of her, my cock slipping free of her folds and soaked in her and Hannah's juices. I let got of her thigh and breast, and she lowered her leg to the flood for stability. I then grabbed her by the hips, pulled us away form the wall, and flung her onto the bed. She let out a noise that was equal parts surprise and glee as she landed on her back and bounce don the mattress next to her sister. I quickly scrambled over, climbing onto the bed and pulling her long legs apart. I saddled up between her legs and pushed my hips forward, my cock finding the mark and slipping between her lips once more as she gasped at the sensation of my re-entry. This time I let her take all of me, moving forward until our pelvises met. I saw Hannah adjust to get a good angle of us on the camera, and with no fanfare I began to thrust hard and fast.

I knew I couldn't blow yet, we still hadn't met the conditions of the deal, but now I was fairly confident that I could really fuck these two without fear of busting too early. So I laid into May with all I had, fucking her as hard as I could. I was greeted with a chorus of "god, yes!" and "fuck me!" as I worked her bald cunt hard. Between her face contorted into a smile as she begged for my cock, to her hands gripping the sheets good and hard it was nothing short of a miracle that I didn't cum right then and there. Not to mention her breasts. My eyes wandered south to her chest to see her pert tits moving splendidly for their size and shape, motions to match the intensity of the pounding I was giving her.

I slowed down a little, but kept up the intensity, holding her hips and slamming her hard and slow like I had with Hannah.

"Good, isn't it?" Hannah asked as her sister got the same treatment she had received.

May could barely get the words out between her moans, but finally her voice slipped through with a "Better than I would have imagined."

I turned to look at Hannah as I continued to pound May. "You want your turn again? Maybe a little harder than last time?"

"Yes, please!" Hannah said, seeming surprised by her own eagerness.

I pulled out of May, took the camera from Hannah's hands and gave it to her sister who lay panting on her back. She managed to take the camera and aim it right at us, which was perfect.

I gently pushed Hannah onto her right side, then lifted her left leg up a little as I straddled her other leg. I moved forward, dragging my balls along her thigh until I felt my cock touching her wet snatch once more. With one more adjustment I pushed between her folds and deep inside her, then lowered her leg a little which applied pressure on us a surprisingly pleasant way. I wrapped my left arm around her leg to help support it, sat up on my knees a little and began to thrust as hard and fast as I could.

"Holy shit!" Hannah gasped as I laid into her. The position maybe wasn't elegant, but it was getting the job done. I could look down and watch her tits in profile as they jiggled furiously with my thrusts, and as I fucked her I reached my right hand up and gave her ass a mighty smack, which only in that moment did I realize that May was seeing her from behind and would have gotten it on camera. I gave her full ass a good hard squeeze as I fucked her for all I was worth.

May got up at one point and moved around us to get Hannah from the front, getting a panoramic view of her little sister taking a cock like a champ. I kept fucking her, noticing how this position felt different than having her on her back, that it felt like I was rubbing the inside of her pussy in a new way that was pleasant for us both. I gave her ass another slap, the sound filling the room for a brief moment, mixing with the wet slapping sound of our fucking, not to mention our moans and words of affirmation.

I lowered myself down a little, and Hannah moaned louder as my cock placed a little more pressure on her vaginal wall in a new way. But the more remarkable sensation was that of my balls now gently grazing the inside of her thigh as I fucked her. Not enough to cause friction burns or anything, but just enough to give a little tickle that felt good as I worked her pussy. I kept going, keeping up the pace and intensity as she demanded between moans, taking in the view. In profile I watched her round tits jiggle, and with a slight adjustment of my head I could get a view of her belly jiggling as well with each thrust. I gripped her ass hard with my right hand, feeling how the soft flesh of her buttocks gave way to my grip. For a brief moment I wondered if I was going to cum, if I was going to just fill Hannah's pussy by mistake, but I knew I couldn't yet.

Eventually my hips needed a break and I slipped free of Hannah's grasp, her pussy trying it's damnedest to keep me inside her, and as I pulled free my cock sprung up and slapped against the inside of her left thigh with a wet little sound. I moved myself off Hannah and flopped onto my back for a moment. I didn't even think about it, and yet without missing a beat Hannah got onto her knees and straddled me.

"I guess it's only fair you get a little break," she said as she hovered her pussy just beyond my wanting cock "and let us do the work for a minute."

She reached down to make sure I was on target, and then lowered herself down around me until she took me entirely once more. She began to buck and grind on me, slowly at first, but picking up speed as she got to grips with the give of the bed under her knees. I let my eyes wander all over her; from those thick thighs, to her shaved snatch, wide hips, up her pudgy belly to her beautiful breasts and finally to that round face with a smile that spoke a thousand words. She picked up speed, moving herself up and down a little as she rocked her hips back and forth, and soon her tits were bouncing hypnotically as she rode me. My hands instinctively moved to her thighs, gripping them as she kept moving in all the right ways. It was sublime, the feeling and the visuals mixing together to paint a hell of a picture. I felt the bed shift a little as May took up a spot to film next to us. I wondered how much footage we would actually have, considering Garret had actually asked for very little in the grand scheme of things.

"Does she ride good?" May asked me.

"Fuck yeah she does." I said.

Hannah leaned forward a little, placing both her hands on my chest and bouncing as much as she could. I moaned loudly as she rode me, finding it hard to keep my eyes open through the pleasure of it all. But I forced them open, I wanted to see her as we fucked.

She continued to ride me, eventually leaning back a little and giving me a better view of her pussy as it slid up and down on my glistening cock. I watched her belly and tits jiggle and wobble as she moved those amazing hips, pushing my hands up her legs as much as I could and just enjoying the feeling of her. Then she slid forward, taking every inch of me between her legs again and holding there as I felt her pussy contract around me a little. She looked at me with her cute smile, and took a couple of deep breaths.

"Okay," she said "mama's hips need a rest for a minute. You wanna see how May rides?"

I nodded.

Hannah dismounted, taking the phone from May and settling in where her sister had been sitting just a moment before. May, meanwhile, took up Hannah's previous position. Like her sister before her, she reached down to make sure we were properly aligned and then lowered her bald pussy down onto me. I felt her warmth, her wetness, her pussy's desire for my cock as she slid down my length until she had all of me inside her again.

Much like Hannah she started with some bucking, getting used to us and the new position. Once she seemed pleased with what she was working with she came to a stop and looked down at me with a grin.

"You wanna see how I ride?"

"God, yes. Show me how you ride a dick, baby."

With that she shifted her long legs ever so slightly, and began to bounce proper. Her legs gave her the lift she needed, her toned muscles from years of running letting her move up and down effortlessly, sliding up and down with ease. She was able to lift herself up so that barely an inch of me was inside her when she hit her apex, and then she'd come crashing back down with a satisfying slap of flesh and fluids.

Over and over, up and down, gliding on my cock expertly. We both moaned loudly as she rode me with the skill of a porn star, and the sensation of her was nearly overwhelming. I forced my eyes open again to take in the view. She reached back to place her hands on my thighs as she bounced on my cock, giving me a great view of her body. Her hairless snatch moving up and down on my cock, her toned legs lifting and lowering her in perfect rhythm, that flat tummy twitching a little every time she came back down and took all of my cock inside her. The smile plastered on her angular face knowing that I was enjoying how she rode me spoke volumes. Her breasts, while smaller than Hannah's, bounced perfectly with every motion. They weren't full by any means, but god damn could they move when she wanted them to.

She leaned forward, putting her hands either side of my head, our faces again mere inches from each other in a way that almost begged me to kiss her. I felt her pussy glide along my cock as she bounced on me with all her skill. Was this what David had been getting all this time? Lucky son of a bitch. I could feel her breath on my face as she panted and moaned, those sounds almost drowning out the sounds of our bodies colliding again and again as she rode my cock.

She sat back up so I could take another full view of her body, this time grinding on me like Hannah had been, looking me in the eyes.

"To your liking?" She said as she gyrated her hips.

"Very much so."

She ground on me a little more, then began to bounce once more. Again I watched her tits bounce as she slid up and down on my hard cock, the perfect amount of movement for their size and shape. She kept at it for a little longer, switching almost effortlessly between bouncing and bucking as she went, before she finally needed a rest. Even in as good of shape as she was, her legs were probably on the verge of cramping up.

"Hannah," I said "you think you're up to another ride?"

"I suppose I have one more in me." She said with a chuckle.

"Give me the phone." I said. She handed it to me and I made sure I had a good angle. She went to straddle me once more, but I stopped her. She looked confused. "Turn around."

The expression on her face was equal parts surprise and giddiness. "You want me to ride you reverse?"

"Yeah," I said "you've got a killer ass. I gotta see that thing in action."

Without another word she lifted one leg, pivoting on her other knee until she was facing away from me. She lowered her leg on my other side, taking up her position. I felt her hand graze my cock, just her fingertips running along the underside of my shaft, and she turned to look over her shoulder at me. Lust, anticipation and something akin to a "thank you" filled her eyes. I felt her fingers nudge my cock ever so slightly as her cunt took me into it's warm embrace once more. I moaned as I watched my dick disappear and all that I could see at my crotch was that amazing, full, ass of hers. A wry smile on her face, vanishing only for a brief moment as she gasped whens he took me into he folds once more.

Then, through the screen on my phone, I watched as she began to grind on me once more. Her ass rocking back and forth, I could feel the way I ground against her insides as she moved those lovely hips. This view was just as good as the one from the front, even if I was missing out on the spectacular movement of her tits, watching that ass move made me throb inside her in a noticeable way given her little gasp at the same moment. I had wondered if I'd be able to fuck her doggy style. Her ass was so full that I wasn't convinced I'd be able to, but Jason had mentioned them doing that position before, and he was around the same length as me from conversations I had heard. But this was a guaranteed position to work and let me see that ass of hers, and so far I had no complaints.

I had even less when, to my surprise, she leaned forward, running her hands down my legs until she was gripping my ankles and leaning as far forward as she possibly could. She lifted her body up, my cock becoming visible for a brief moment before she slammed back down on me. She did this over and over, and I watched as her beautiful, fat, ass jiggled every time. I watched as the ripples moved across her skin every time she brought her hips down on me, the way her butt cheeks jiggled and moved as she bounced her cunt on me, moaning as I rubbed something in her in just the right way. It was incredible to watch, and even more incredible to feel. Listening to hear moan as she rode me just made it all the better.

She sat back up at one point, bucking her hips on me again, and she turned to look over her shoulder at me once more. The look on her face as a combination of a wry smile and pleasure, her mouth slightly agape and her eyes having trouble focusing as she ground on my cock. Her hands disappeared, but I could tell one hand was now cupping one of her breasts from the angle of her arm, but the other reached down and rubbed at my balls as she rode me. I nearly blew my load right then and there.

"I want you to fuck me like you fucked May," she said "I want that hard and fast on my back shit she got."

It took a moment for my brain to process what she had said, I was so lost in the pleasure of how she was riding and touching me, but once it all clicked I nodded to her. I handed May the phone, reached my hands down and gave her ass a couple gentle slaps to indicate to get off. She dismounted, seemingly very excited, and asked where I wanted her.

"Back where I had you the first time." I replied, pointing to the foot of the bed. She quickly got into position, her waist hanging slightly off the edge of the bed, her feet planted on the floor as she waited for me to take my spot. I rolled off the bed and walked over to get between her legs once more.

I assumed my position and pushed my cock back inside her with a moan, feeling her body welcome me once more until I was balls deep inside her again. I gave her only a moment to take in the sensation, and then I began to thrust. Hard, fast, furious, exactly how May had gotten it. I placed my hands on her belly and fucked her as hard as I could, pushing my body to it's limits and regretting nothing. I watched as her soft tits bounced and jiggled as I slammed her sweet snatch again and again, watched as her eyes basically rolled back in her head and her mouth hung open in a near silent scream of pleasure.

My hands moved up her body, grabbed hold of her breasts and groping them as I kept fucking her. I was taking in every sensation I could with her, reveling in the feeling of her pussy around my cock, the softness of her breasts in my hands, the way her moans and voice floated to my ears over the sounds of our bodies colliding.

"Yes, that's it!" She moaned as I plowed her. "Fuck me hard! Fuck me like you fuck Alex!"

Two things clicked in my brain at that moment. First was an instinct to stop at the mention of my wife's name, but I was in too deep and that was drowned out by the second: giving her exactly what she requested.

I slowed down for a brief moment, moving my hands from her breasts down her body until they were on her thighs. Then I guided her legs up, until they were pointed straight up and pressed against my body. I wrapped my arms around Hannah's thick legs, and then did what she asked. I fucked her how I fuck her sister.

I plowed Hannah harder than I had before, with more gusto and lust than before. I fucked her hard, fast and without mercy. Again, my sense were getting overwhelmed in the moment. The feel of her skin against mine, the sounds of her moans, the warmth of her pussy as I slid in and out of her, the distinct sound and feeling of my balls now slapping against her ass with every thrust. Her ankles were either side of my face, letting me look down upon her glory as I fucked her. And I felt her body twitch and spasm as she came, her pussy tightening around me as she was rocked with pleasure.

It nearly pushed me to the edge. I couldn't take much more, and I knew how this was going to end.

"May, give her the camera," I said between breaths "I'm so fucking close!"

"How do you want me?" May asked.

"Doggy."

I hadn't even noticed that she had changed positions on the bed earlier to get a good up close profile of me fucking Hannah, and she quickly scrambled to get into the new position. She placed the phone on the bed next to Hannah's hand, and she reached over to get it into her grip as I let go of her legs and pulled out of her.

A quick step to the side and I was behind May. She was on her hands and knees on the bed, her lower legs hanging off the foot of the bed, that delightfully fully and firm ass on full display for me. I had only a second to appreciate the view, and what a view it was, before I took my sensitive cock into my hand and guided myself into her waiting folds. Taking her from behind felt like a whole new game, a whole new sensation, and we both moaned as I pushed every inch of my cock inside of her. I wasted no time getting moving again, fucking her good and hard. Her ass didn't move like Hannah's, being smaller and firmer, but the little bit of motion I got out of it while thrusting was pleasing to the eye.

I grabbed her ass with both hands, giving her firm, toned, runners buttocks a good squeeze and slapping her right cheek to see how it would feel. Her head was tilted back, and I could hear her moaning over the wet slapping of our genitals, I could see the muscles in her back tensing up as it arched involuntarily. She felt amazing, looked amazing, and my eyes wandered away for a moment to see Hannah, sweaty and still panting a little as she made sure to get the action on camera. Her body was glistening with sweat, and the wet spot on the sheet between her legs spoke volumes. I turned my eyes back to May, gripping her ass tighter as I picked up speed.

I moved my hands to her hips, holding tight as I fucked her. There was no denying what was coming, I could feel my body tensing in preparation for the climax. I picked up the speed a little, as much as my poor body could manage, and finally felt it.

There was no denying that May felt it as well, a surprised little sound escaping her as she felt my cock throb inside her and unload warm cum in her pussy. But my body had gone on autopilot, it wasn't receiving the signals from my brain, and I just kept thrusting as I came more and more. I could feel the cum we were pushing out of her body, feel it along my cock and dripping down onto my balls as I continued to fuck her. More and more, pulsating in May's beautiful cunt as I filled her to burst, and then she came as well. Her body clenched around me, her pussy gripping me tight as it worked to milk me of every last drop of my semen.

Finally my body got the clue from my brain, and I pushed deep inside her, every inch of my throbbing, pumping cock buried between her folds. We both moaned, and then the room went silent for a moment. We sat there, just letting the feeling soak in. Then I felt the distinct touch on Hannah's hand on my balls, sending a shock wave through my body and eliciting one last spurt of cum into May's uterus, her walls gripping around me to make sure her body was getting all of it.

When I finally was able to move again I pulled back and felt my cock slide out of May's pussy. Hannah was there with the phone to get the perfect shot, my cock exiting her sister, followed by a thick glob on white cum spilling out of her now that the way was clear. Some had escaped during the actual fucking, as evidenced by what was on my cock, and little bits splattered on both our legs.

I watched as May gave up, slumping forward onto the bed on her belly. I took a couple of steps back form the bed until my back hit the wall, and then I let myself slide down to the floor as my legs finally gave out from under me. I sat there, eye level with May's pussy on the bed, her ass above that. Hannah sat on the bed, she had stopped filming and put the phone down. She looked back and forth between us a couple of times, her eyes occasionally stopping at the puddle of cum on the bed sheet.

"I gotta say, from a viewer's perspective that looked pretty intense. And was pretty fucking hot." She said.

"It was both of those things," I managed to say after what felt like an eternity of trying to get my voice to work "and felt amazing. At least for me."

"What about you, May?" Hannah asked.

She just lifted a hand and gave a thumbs up.

We all sat in silence for a couple of minutes, catching our breaths and letting the realization of what had happened sink in. We were all going to be better off for it in the long run, but it did hit us all that we had just had a threesome and I had cum inside one of my sisters in law. Once my legs felt like they were going to work again I picked myself up off the floor and made my way to the bed again. My legs were wobbly and weak, and I was sure once the adrenaline fully wore off I would be sore as hell and in desperate need of hydration. I took a seat on the bed near May, watching her body as she breathed deep.

"I'm going to take that thumbs up to mean you aren't disappointed." I said.

She turned her head to the side and spoke. "Not at all. It's a little weird thinking about it all, but I can't say I'm disappointed in the slightest in that regard."

"That's reassuring to hear." I said, and then, without thinking, gave her ass another playful slap.

She rolled onto her side, giving me a look that didn't seem angry, but just read "really?" Why had I done that?

"Sorry," I said "you have a really nice ass and it was just there calling out for it."

"You're fine," she said a moment later as her features softened "I suppose you've earned it. And until we leave this room I guess it's okay. But once we're out that door? Nothing like that can happen again."

I nodded, and Hannah added a "So get your spanks and gropes in now while you can."

She had said it almost in jest, but I took her at her word, reaching an arm over and giving one of her tits one more good squeeze. She just chuckled at the bravado as I let go of her breast.

May finally got on her feet again and said she needed to go clean up. There was a bathroom one door down the hall we had passed on our way to the bedroom, and she made her way there to take care of things. That left Hannah and I alone in the bedroom for a minute, and when she got on her feet she looked down at me and smiled.

"One more for the road." She said as she turned and presented her ass to me. I gave it another good slap and grab, cherishing the moment a little.

I would see Hannah again soon after this, and I'd have the mental image of her naked body burned forever in my memory. I'd likely never forget how she felt, how she tasted, how well she sucked a cock. Maybe one day I'd get to tell Jason that he was a damn lucky man to get that on a regular basis, but I suspected that wouldn't be for a long time.

May came back in after using the bathroom and I watched as the two of them got dressed. Taking in my last looks at their nude forms, final glimpses of their breasts, their bare asses, and those beautiful MILF pussies.

"Aren't you gonna get dressed, Tyler?" Hannah asked as she pulled her shirt back on.

"In a minute," I said "my legs are still pretty mad at me. And my hip is none to happy."

The girls both nodded, walked over the the shelf and picked up their rings, slid them back on to their fingers and made their way downstairs.

I joined them, and the rest of the party, about five minutes later. I had laid on the bed for a bit, letting my body rest and letting the smell of sex that permeated the room fill my nostrils. Finally I got up, got dressed, grabbed my ring and went back downstairs.

"I understand the deed has been done?" Garret said.

I nodded.

"And the proof?"

I pulled up the gallery on my phone and handed it to him. "Check for yourself, all your rules were met."

He took the phone and began watching the videos. He commented how a couple of the files seemed pretty long, to which none of us gave any comment. He scrolled through, fast forwarding through some parts of the longer clips, and I watched his eyes go wide as he got the end and was clearly watching as I came in May. With a satisfied smile he handed the phone back to me, turned his head to Isabella and nodded. She tapped her own phone a couple of times and nodded back to him.

"Your money should hit your bank accounts by morning. We worked it out so after taxes you'll get the full million, as promised. I hope that, despite the oddness of the situation, the three of you at least enjoyed yourselves. You were up there for a decent while."

None of us said anything, despite my wanting to confirm that we, or at least I, did have a good time.

"Well, then the deal is done. You can delete those videos now if you so choose."

I held my phone up and deleted the files as Alex stood beside me and watched. First from the gallery, and then from the trash, forever removing them from my phone. She kissed me on the cheek, and said we were leaving. I offered no argument and followed her, May and David out to our car. As David was loading the few things we took with us into the trunk I heard Alex and May talking, Alex asking how it was. May said it was good, and that Alex had been right about my tongue.

As we climbed into the car I saw Hannah and Jason get into theirs, and one by one we pulled out of the driveway and started to make our way back home.

The drive was relatively quiet. I was sure Alex and her sisters would discuss the whole thing further, they loved sharing like that, but it was clear May didn't want to talk about it in front of David at the moment. I couldn't blame her. And as we drove along the dark roads I felt a pang of guilt. Not only over what we had done, but over the fact that those videos weren't gone forever. During the time I had been alone in the bedroom, I had uploaded to them a cloud drive. I loved my wife more than anything, but I'd have been a damned fool to get rid of such compelling video. And now I wouldn't need to rely entirely on my memory for the full glory of May and Hannah.

Was it kind of shitty to do? Yeah. But can you blame a guy for wanting to preserve such a night?