The Perfect Match Pt. 02

This is the conclusion from Part 1...

Throughout my various trips to Vegas over the years, I've had many "morning after" breakfasts. They usually take place at some breakfast buffet and contain a combination of laughs, feeling hungover as shit, and a whole bunch of "What the fuck happened last night?" This Vegas morning after breakfast had some, but not all of that.

After Dave and I retired to our own bedrooms last night, it took awhile before I fell asleep, mostly because I was still replaying in my head everything that had happened. One upside to having that extra time was I was able to drink a lot of water, so amazingly I didn't feel hungover at all the next morning. In addition to feeling fine physically, mentally I was ok as well. I didn't feel nearly as awkward as I would've expected, and while I wasn't exactly going out of my way to discuss the details of our mutual masturbation the night before, Dave made a couple vague comments about how it was a fun night, but that was about it. For the most part, we had only just talked about other aspects of our Vegas trip.

About halfway through breakfast though, Dave apparently thought the time for small talk was over, and decided to dive right into the conversation. "So here's what I think the plan should be." He said.

Initially, I'm a little unclear as to which plan he's talking about. Is he talking specifically about the plan to somehow convince our wives to agree to a wife swap? Or is he talking more vaguely about how we need to address what happened, the sharing of our wives' pics and jerking off together, and whether we should admit what happened to Jenny and Sara? Or maybe it's one plan that encompasses both?

"Ok, what were you thinking?" I answer back, figuring I'll know the answer to my question soon enough.

"I'll talk to Sara and suggest we organize a weekend getaway at a VRBO for the four of us, like maybe to Napa? I'll make sure it has both a pool and a hot tub, and as long as it's totally private, that should give us the opportunity we'll need. We'll have plenty of wine, maybe we suggest a little skinny dipping, and I think we just let things play out from there."

After hearing Dave's explanation, it's clear he's still all-in on pulling off this foursome, and that's his only focus. And to be honest, I had zero second thoughts about still doing this as well, so I was excited to hear he's still into it. I knew there might be some logistical issues though.

"I love the idea." I tell him. "I'm a little worried childcare is going to be an issue though. We don't have anyone easy to just watch the kids for a weekend like that."

Dave heard this and clearly ponders it for a minute. Then he says, "Fuck it. Let's do the whole families. I mean our kids go to bed by 8 anyway, I don't think that's an issue as long as the house has room for them."

"Yeah I don't think having the kids sleeping inside the house is a big deal if we're out by the pool."

"Ok nice. I'll look at some rentals and find the perfect place. I'm sure Sara will love this idea, so I won't have to convince her at all." And then Dave chuckles and says, "The weekend getaway that is, the wife swap will be a tougher sell."

"Yeah, this all sounds good to me." I say, but I still had some reservations about whether this should be a plan we try to pull over on them, or if it might make more sense to just come clean? "What if we just told our wives what happened? Would that be so crazy? I obviously don't know Sara very well, but there's a chance that I could tell Jenny and after initially getting mad about the sharing of pics, she might actually be intrigued by the idea of this foursome?"

"Oooommmph." Dave responds with an exhale. "Don't get me wrong, I do think there's at least a small chance Sara would agree to something like this if I just came out and asked her... I mean, and I swear I'm not making this up, I think she has kind of a crush on you."

This totally catches me off guard. "What??? What the fuck are you talking about?"

"No seriously. She's always talking about how you have this perfect form when you run, and how she's trying to copy you and how you make it look so effortless."

"So? That doesn't mean she wants to fuck me." I respond.

Dave continues to explain, "Trust me, I know my wife. There's something there. And besides, she's in great shape and you're in great shape. I'm clearly not, so you don't think that appeals to her? Come on, it must."

"Dude, I don't know..." I say trying to both reassure him that his wife still finds him attractive, and also show my skepticism that she is attracted to me. I mean, it wouldn't be the worst thing in the world for both me and this whole scheme we're concocting if she is, but I had my doubts.

"But anyway, I'm just worried that Sara will flip her shit if I told her I showed people the pics I have of her." Dave says, returning to his reasoning on why he can't just admit everything.

"No, I get that. I'm scared as hell about that aspect with Jenny as well." I say. "But even with that, would it totally screw you over if I did tell Jenny what happened?"

"You do you, man." Dave says reassuringly. "I wouldn't ever want to ask you to keep something from your wife that you didn't want to."

I was really relieved to hear Dave say that. I felt like that conversation could've gone one of two ways really quickly, and he easily could've brought up some bro-code bullshit and attempted to guilt me into not saying anything to Jenny.

"Ok, well I honestly have no idea how, or even if, I'll approach it with Jenny, but if you wanna look into this Napa weekend, I'm all for it. I mean, even if the wife swap doesn't happen, it would still be a great time."

"Yeah for sure. Let's get it on the calendar and we can figure it out from there."

And with that, we wrapped up breakfast and had our initial plan in place. From there, we had a pretty casual last few hours in Vegas before our early afternoon flight home. We did continue to chat a lot, including a number of sex-specific topics. Once Dave brought up the wife swap at breakfast, it was as if the dam broke and we were free to talk about everything, even while dead sober. I had had those types of chats on Omegle before, but those were over text with anonymous strangers, so this was quite different.

We talked about our sexual history and about our ex-girlfriends. We found out that we both had vasectomies after our second kids, so neither one of us ever worries about birth control anymore. I asked Dave if many of his friends knew about his ridiculous penis, and he said hardly anyone knew other than Sara and his exes. He mentioned that he never played any sports after middle school, so he's never really done the whole showering in a locker room thing. He did show me that he had made a Reddit profile and had posted a number of times to r/massivecock and r/sizecomparison before. He never posted any pics with a face, but they were still pretty fucking crazy to see.

At one point we discovered we both like to smell our wives' dirty parties whenever we see them in the laundry. And despite his aversion to eating ass, Dave and I both shared a love of smelling and licking pussy. We talked about how hot it would be if one time we got together, we both brought a pair of our wives' used panties from home and took turns sniffing each of them. Would they smell basically the same, like some generic pussy smell? Or would we be able to tell whose is whose with our eyes closed and just by the scent alone. It would be super hot to find out. Overall, it was pretty crazy talking about these sorts of things so openly with a friend.

The flight home was uneventful and I was happy to see the family. I filled Jenny in on all of the gambling, drinking, and eating stories, but didn't initially mention anything regarding the whole other side of what went down. I was still debating about whether or not I should tell her, for so many reasons, but I figured I didn't need to decide immediately.

Later that week, Jenny came up to me very excited and told me that Sara and Dave had invited us to join them for a weekend in Sonoma. I acted excited, as would be expected, but I did mention that Dave had told me in Vegas that we should get the families together for a trip like that. Jenny was ecstatic, and when she showed me the link, I have to say I was quite impressed with the place as well. It was a beautiful villa, and sure enough it had a heated pool, plus a hot tub. We were looking at the VRBO link, and so we could easily see the average price, which was four grand a night. It's mind blowing to me that people spend that amount of money on a whim, and it was very generous that Dave and Sara would include us in this, but I couldn't help but think of that money as helping us to buy us our wife swap. It's kind of funny, crazy, and depressing all at once.

After some back and forth between Jenny and Sara, we confirmed the VRBO for a Friday and Saturday night in just a couple of weeks. That wasn't a lot of time for Dave's and my master plan to come together, and it also meant I had to decide soon whether I was going to tell Jenny the real reason behind this weekend getaway, or just follow Dave's approach and try to have this foursome unfold spontaneously. It was not an easy decision and one I spent a number of nights thinking about in bed before I came to my decision.

Ultimately, it came down to one thing. I actually thought that telling Jenny what transpired in Vegas might be our single best chance to pull this ridiculous wife swap off. Maybe I was crazy to think that, but I thought Jenny would probably see through any scheme we had, so my only hope was to be upfront with her in the first place. Generally speaking, telling the truth is obviously the right thing to do, so in this case where maybe, possibly, it'll help us with our foursome as well? It seemed like a no-brainer.

So I decided that I was going to tell Jenny. Realistically, I knew I would probably never be 100% honest, because I always seem to try and spin a narrative slightly to avoid total responsibility. That's just how I am, and I usually accomplish this with lies by omission. I'll never say something that is demonstrably false to Jenny, but I'm sure if someone was auditing my life they could point to any number of instances where I left out the full truth. I honestly don't know if this makes me weak and kind of a liar, or if this is something that perhaps every human being on earth does.

So we're about a week and a half out from our weekend family getaway, and Jenny and I just happened to be in bed at a reasonable time getting ready to watch a show. I figured now was as good a time as any, so I started right in. "I have to tell you about something that happened when Dave and I were in Vegas."

"Uhhh, ok." Jenny initially responds. Then a second later after she processes what I said, adds, "That sounds kind of ominous."

Now, I had thought about how I wanted to start this confession/explanation off, and I figured I would begin with the part that I was confident wouldn't get Jenny upset. It also had the benefit of being embarrassing to me, which I was hoping would help deflect or shield me from any potential anger about the subsequent things I was planning on revealing.

"When we were in Vegas, Dave and I jerked off together. Like in the same room."

Jenny's reaction was probably how I would've guessed it to be. She just goes, "What???" While simultaneously showing total confusion and stifling laughter. Then she says, "Like you touched each other's penises?"

"No, no, no, no, no." I quickly clarify. "We touched ourselves but were next to each other and could see each other."

"Still." She says. "How the fuck did that happen? Have you done this before with other friends?"

"No. Never." I respond. "Ok, first off, we were quite drunk."

"Yeah, could've guessed that. Still doesn't explain it. Go on." Jenny says, and she's now leaning forward almost as if she's excited to watch the season premiere of her favorite show. She doesn't appear to have any hint of anger, which again is probably what I would've guessed knowing her and knowing how surprising this news would be. She looks captivated instead.

I continue on, "So Dave was telling me that he apparently has a huge penis. And I didn't know this before this trip."

"Wait, wait, wait." Jenny interrupts. "He's just bragging to you about how big his dick is?"

"No, no, not at all." I say. And here I have another chance to say something that I think will help dampen any anger down the road. It's a statement that is both true and embarrassing to me, so despite how cringeworthy it is to admit, I think coming clean about it is more than worth it in the long run. "I kind of saw it in his shorts and asked him about it."

"What??? Who are you?" Jenny asks now in full blown laughter.

"I know, not my finest moment." I say. "But anyway, so he's doing the exact opposite of bragging. He's going on and on, even getting emotional, about how much having a huge cock sucks, and how he and Sara can barely have sex, and how he's convinced she's not attracted to him. All this stuff, and it was clearly real, and I felt really bad for him."

This whole explanation is all mostly true, but certainly slanted to help elicit some type of understanding and sympathy. I keep going.

"And so, you know me. You know what my number one fantasy is. So big shocker, I'm drunk and I tell him he has to fuck you. And I tell him I would love to watch him do it."

"You didn't! You said that?" Jenny said with a shocked face and now a slightly less amused look. "Wait, so he and Sara like can't have sex? Like physically can't??? How big is his dick?"

"It's enormous. Like borderline greenie sized." I answer, comparing it to Jenny's favorite 10-inch dildo.

"Shut the fuck up." Jenny says, and for the first time in this conversation I think I see the slightest bit of arousal in the emotional roller coaster she's on. "So what did he say when you told him to fuck me? That's so ridiculous by the way."

"Uhhhh, he told me he would..." And then I paused for a moment before continuing, "but only if I fucked Sara."

"Ha. You guys are sooooooo lame." Jenny says with a mocking tone.

At least so far, there's still no sign of Jenny being upset in the least, but I haven't gotten to the biggest sin yet, so I was still plenty worried how it was going to turn out in the end. Before I even got to the pic sharing part, I had to navigate through the part where we discussed eating Sara's ass too. So I tried to frame that as delicately as I possibly could.

"Yeah so Dave was talking about all the ways that he thinks Sara is disappointed in him, and he mentioned that she's always asking him to lick her butt, and he thinks it's gross, and I mentioned that we have the opposite problem where I want to do that to you, but you think it's gross." I'm trying my best to make this sound reasonable, and I'm completely twisting the order events, but it's tough. "And so that's where Dave gets the idea for me to fuck Sara, so I can lick her ass, and I want him to fuck you because his penis is the perfect match for your pussy, and yes, I get it, we're ridiculous, and I know we're ridiculous because we ended up jerking off in front of each other so you don't need to tell me that."

"Ok, ok." Jenny interrupts as she merciful cuts off my rambling explanation. "Well I appreciate you telling me, and so now I have to assume this whole Sonoma weekend is part of your lame plan here?"

"Just don't be mad at Dave, you have to understand I was the one who first suggested that he fuck you, so I set the whole chain of events in motion. I can't explain to you how emotional he was getting talking about how much he hates his penis. It was unlike anything I've ever seen."

Jenny responds, "Oh I'm not mad, I actually find the whole thing quite entertaining." And then she smiles and says in the most playful mood since the conversation, "You're such a nice guy though to be willing to lick Sara's butthole for Dave. I mean she's probably the prettiest friend I have, so I'm sure you wouldn't enjoy that one tiny bit."

At this point, things have gone as smoothly as I ever could've hoped. Jenny clearly isn't mad and is even making jokes. I seriously contemplated just bailing on the plan to tell her about the picture sharing, but for once I actually manned up and faced the consequences.

"There is one more aspect I have to tell you, and it's definitely the worst part." I say, and as I do I can see Jenny's mood dampen quite a bit.

And then before I say anything else, something dawns on her and she says in a much more stern tone, "You didn't???"

I figure she already knows what I'm about to say, so I just tell her. "When we jerked off, I showed Dave the pictures I have of you." And then I continued with the part that probably wasn't as obvious, "And he showed me some he has of Sara."

Jenny says nothing in immediate response and just looks at me. I simply say, "I'm sorry."

Another ten seconds go by, and I'm still waiting for her reaction. And then finally she says, "That's so fucking not cool."

"I know, I know, I'm sorry." I apologize again. And to be honest, so far her reaction is not as bad as I had feared.

Jenny then asks, "Have you ever showed them to any of your other friends? Like at any point before?"

"No, never." I answer, which because she specifically asked about my 'friends' is technically not a lie, but I think certainly falls under the lying by omission category. But there was no way I was brave enough to admit right now to having also shared them with random strangers online.

"Get up." She instructs me. But not in a way that seemed like I was supposed to leave the room. I didn't know why she wanted me to stand up, but of course I did it. So as I'm standing by our bed, Jenny then gets up and walks over and turns on our bedroom lights. "Take off your underwear."

I drop my boxers to the ground and now I'm standing there in our bedroom naked, and then I see what's going on. Jenny lifts her phone and snaps a naked picture of me. "Start jacking off until you're hard." She then tells me. "I want these pictures to be as embarrassing as possible."

So I start jerking myself off, and not surprisingly it doesn't take long for me to get hard. The idea that Jenny is taking some sort of sexual revenge route is way better than I thought her reaction might be, so I am both relieved and turned on at this development.

"Ok, sit down. Like with your legs in a butterfly." She tells me. And so I do, and now she's snapping pictures of me sitting on our floor, my knees pointed out, and I'm just holding my dick in my hand. I agree I do look pretty ridiculous right now so I'm sure the pictures aren't very flattering.

"Hmmmm." I hear Jenny say as she's audibly thinking about what to do next. "Ok, let's see how flexible you actually are. I want you to lean your head down and try to lick your own penis."

I certainly didn't see this coming. "I don't think I can reach it, I'm not THAT flexible."

"Well give it a try. Go." Jenny demands.

So I give it my best shot. I stretch my back out and lean forward as far as I can. I can get my face pretty low, but it's out too far in front of my cock. As I have my head down there I hear her taking more pictures, and then she tells me to stick out my tongue as I'm so close. So I do as I'm told and I reach my tongue out, but can't quite reach my tip. Now if I had a 9-inch penis, I'm sure I would've been able to reach it, but as we all know, I don't.

"Ha. These are perfect." Jenny laughs as she starts looking at the shots she taken. She then turns the phone around and shows me one and says, "So do you mind if I send some of these to my friends? Or maybe I can send them to some of the other dads at school?"