0:05 Welcome back to another episode of Careful Boys. We're here with Will Pepper. We just heard something pretty interesting Ath had mentioned it where would you rather have a woman who is untouched like virgin everything she's ever experienced is only with you. I mean this is like real like right after the Jihad pristine and it's um or you have a girl who had her ████ phase gained some skills in that phase. Now she's kind of known. >> Yeah. Known? But now she's devoted to you and all of those ████ skills can be used on you. >> And she's loyal to you though. She's not doing that like with anybody else but you. >> And both of them are equal both of them are equally fine equally fine. Yeah. equally fine one just has a sexual history that has But the virgin one is not that good. She doesn't know what Well she everything she learned is from him. One of them the book of her sexual
0:55 history you open up and go >> [snorts] >> and it goes like ████ dust goes everywhere. >> Yeah yeah. Wait what do you mean by like I know people that have that already hit it? Oh like your dad like your dad already hit it. Not your dad. >> dad that let's not ruin it. Oh okay. >> [laughter] >> jump we can go there later. You know people but you know Is her exes like NBA players or like Damian Lillard Damian Lillard? >> [laughter] >> He was in Utah too that's crazy. That's why that's why I said it. male comedians >> Well of course he's going to say no. No you can't make it that hard like this. We got to we got to keep it on the skill. But in her circle like you met some of her friends and then you realized she they she ran around in that circle. Except for Jason Channing Jason Channing's in that circle. Well I don't want to make it kryptonite for him right away. Like why would you want to have him to have one choice? We got to we got to balance it. You run into little a lot.
1:46 Let's [laughter] balance it. >> Wait is it like a little paw thing? Like his like if I do something like yo I I I smashed your wife before. They've been they've been there. No they're respectful though. They just like every time they say what's up to you they good to see you well every time they see her they're like it's really good to see you and they hug. How much sexual history is too much sexual history for you? I I I would prefer if you had like a few long-term partners. That's very sweet. Because as I So for you >> [laughter] >> it's better that they ████ like five long-term partners but 10,000 times versus a girl that's only had 20 partners but she only ████ 20 times. See that's different. 21 night stands or You got to put in 50 five long-term relationships but 10,000 times?
2:38 >> Does that make a difference to you? Um yeah. No but you'll you'll forget. Once you're in the mood you'll forget so you have to understand what that does physically right? Every time you're having sex with the experienced partner you might feel like you're playing a little bit operation you don't know if you're touching the walls sometimes right? But when she does something to you it's like amazing. Other side other side the innocent one you're like you're doing damage doesn't matter how little your dick is cuz you're you're doing damage cuz it never touched anything before but she's always like >> [snorts] >> wow ah and it's crazy. >> [laughter] >> wow But in my experience is I'm not even packing like that I'll be honest but it's um when they're like when you're connected it's even if you're not packing you know what I mean? She's looking for a beauty. Yeah yeah yeah. You're connected you're committed. >> think do you think sexual history could stand in the way of that feeling? Um unless they were like some some some
3:28 childhood should happen maybe. Oh Jesus. Wait explain explain explain explain. Like some some crazy trauma stuff. If that then yeah but No that's not there. They just she's like I'm going to show you what my daddy >> [laughter] >> Just previous just And she's like now let me show you what my stepdad taught me. If it's just like having a lot of previous partners about that myself does that hurt Um if it's like a crazy number then yeah but if it's like It's it's mid double digits. Like 50? Yeah. Um that's kind of a lot. >> [laughter] >> That's kind of a lot. I have like I'm not like you know I What if it's less what if it's less than presidents? >> [laughter] >> Seven something? 40 40 let's say it's 46. Almost the same. Oh oh we only have 46 presidents. We have 47 right now yeah. How about this? I guess it's fine. It's fine. Because we've had multiple presidents have two terms.
4:18 >> relative reality How many different people do you think you paid for like hand jobs and happy endings? Total? Yeah. I don't know. Whoa are we talking more than 20? You don't know because it's so many? I'm not going to I'll plead the fifth. >> [laughter] >> Don't don't hint at any facial reaction we're just going to read the room right now. All right was it like more than 20? Like based on my face? Yeah yeah don't react. Was it All right was it >> [laughter] >> All right was it more than 25? Wait hang on let You volunteered to do this. You got better go 30 now. Is it more than 31? He's nodding. NO I'M NOT YOU NODDED A HE'S LIKE MORE THAN 30. WAIT we need a we need a We need a control group. Can we just see
5:08 your resting face? Okay that's that's the resting face. Okay so make sure you don't do this when I go say and I don't don't >> [laughter] >> Try not to do that. Yeah why'd you not? Above 25 he's like Say like is it more than what's the amount of Skittles in a normal bag? >> [snorts] >> Oh ████ [laughter] dude. Use use comparisons. Is it more than the amount of phalanges you have on your body? Is it more or less than the freeway that goes through Pasadena? >> [laughter] >> All right. So so so based off of whatever that truth is all right your new wife has had the same amount of partners. >> [laughter] [laughter]
5:59 >> Good answer. [clears throat] No um no it's it's probably fine I don't know. Okay. All right. For you it seems like it what you really just are after is the connection part of it. And if that part is strong you can overlook or whatever deal or the other parts aren't important. So if they're a good person yeah Does that mean when let's say you meet somebody and you're dating very very early stage right? Do you never want to get onto the topic of body count etc. so that you never know or do you want to know? Uh I want to know. Oh You want to know? You have to get you have to go there. You don't need to know names necessarily. But you have to Say that if that knowing also means that she's going to ask you about all your stuff too. I'll be honest. Is it all is it a fair trade? Yeah. It's like a children's book right? It's like oh yeah sure here's my little children's book compared to your ████ tome. So let's say so let's say there was like let's say she only had two partners right? But each partner she's been with
6:50 them for 10 years and each partner they ████ hundreds of thousands of times. >> [laughter] >> But it's but it's love. >> That's better than like 30 partners and they ████ like two times. No. Oh Because it's like 10 years two times like y'all didn't what happened? Oh no How did you go to the like how did you not go to the finish line type of thing? So you think wait wait what you mean like that's weird that you didn't stay together? Yeah he's like why'd you go 10 years and then break up? It's too too crazy an example yeah. Like twice? Like something Like maybe you ████ maybe you ████ once a once a you ████ once a month right? >> No you're saying like a 10 year relationship versus two sexual encounters with a stranger. Yeah >> [clears throat] >> I'd rather have the the long-term one. Ah yeah. So they've been damaged for hundreds of thousands of times. Is it
7:40 damage if it's the same size penis over and over? No I guess it's like yeah I don't know it's just funny to me cuz the sexual jealousy ████ it's like they're already done. I think it's more reputationally it's that there's two more people that this word can travel to. Do you think do you think do you think it's because it's more like the guy found her precious so they treated her so she's not ████ and then other guys treated her as like one night stands it was like Bro I can tell you my experience man the exact same thing happened to me. You got treated like trash? dated her we got together I treat I thought she was so I treated her so special had this whole it's my ████ fault cuz that's what happens when you pedestal somebody. And then like first couple months of relationship we had the body count talk. ████ hundred triple digits triple digits >> That's a freeway for sure. Yeah that's
8:30 LA. It's the freeway that goes to LAX. The 405? >> [clears throat] [laughter] >> And if I couldn't deal dude I couldn't deal. >> The 710? I couldn't deal bro. I think I think what Joe is trying to say is if we do it like a car analogy do you like a car with like 10 drivers but only like a hundred miles or like one driver and it has a hundred thousand miles on the car? I think that's what he's trying to get at. Like the like the car still runs. >> It runs but you know it's been used and used and used and used and used. And they drove to Sedona and back Sedona and back Sedona and back. I'd rather have a car that was loved right than a fleet rental. >> [laughter] >> That's true a fleet rental. Yeah yeah yeah yeah. At Enterprise. >> [laughter] >> But then if you think about it right? If if she's only got like a one night stand by like five guys
9:21 whatever right? Then that means the time was spread between these five and none of them is important but then when she spends time with you she's got the skill but you're the first one that turned her whole ways around and she goes I'm going to quit my whole life for you. And then she stays so she'll suck so hard but then the other guys were like I got a little skill out of it but like I only ████ once or twice and no one stayed long enough for me to really love them. >> be willing to date somebody that you're catching in the middle of her whole phase and you're removing her from that? Yeah. But okay if you if you have have car and there's 20 drivers and even though there's only 100 miles, none of those 20 drivers wanted to keep the car? Uh yeah. Yeah. But what if what if what if Oh yeah. all wanted to keep her, but she was the disinterested one and she goes, "You ain't good enough." You ain't good enough. But what if it was? What if it was Then I guess it's
10:12 fine. >> [laughter] >> So what I'm So what I'm So what I'm getting from you is it's a power dynamic. Is it? It's a power dynamic. >> Can I ask the room a question? Yeah. Has anybody here ever gotten a rental car and then walked up to the register and been like Can I buy this I actually buy this one. >> [laughter] >> That's pretty funny. I don't think so. I don't ████ think so. Are we still talking about cars? Because we know it's a rental from the jump, right? Some of us here we rent to own. We rent to own. And some lease to buy. Some lease to buy. Can I actually buy this Ford Taurus? >> [laughter] >> You've ever been in an Airbnb? Did you say the same offer? Exactly. Actually, I have. You have? >> Oh. No, but I I just can't afford buying it, but I've been in some Airbnbs where
11:02 I'm like, "I wish [snorts] I could live in this motherfucker." >> it's the beauty of not knowing initially. Right? So like nobody walks up to the to the counter and goes, "I want the used car." It's that you find out it's a used car later. Maybe there's some majesty to that. >> Already love the car. >> You already love the car. >> When you love the car, that's not >> good that you're just like I'll I can live with this. Would you rather be with the chick who's like been with just like 100 dudes, right? You don't know nobody. It's just that's just her past. Or would you rather be with a chick who's been with like two dudes, but you know them both? Very closely? Like yeah yeah like high school friends or what? No. Do you just They're in your world. They're comedians. Oh, that's worse. No, I'm gay. So it's more like a um familiar thing cuz if she ████ 100 guys, you're never going to meet them again. This happened in Zimbabwe. You'll never see them. Right.
11:52 >> She moved to America. But she's loose as ████ though. Oh, come on. Can't keep adding ████ that >> Wait, why not? She's loose as He keeps adding dealbreakers. AND ALL OF HIS ADD-ONS ARE LIKE, "WELL, clearly [laughter] I'm going to say no." Do you want this free Rolex, but it has A BOMB INSIDE? >> [laughter] >> IT'S IT'S IT'S It's really bad. She had sex with 100 dudes. It's probably loose. >> [laughter] >> She's loose, but she also has really nice toes. But she also got ████ VAMPIRE TEETH. >> [laughter] >> SHE'S ACTUALLY A MAN. OKAY, SHE GIVES ████ every day, but she has vampire teeth. Okay, thanks. Thanks. Thanks, Anthony. Tolerating things you didn't like in a girl because she sucks so good. >> [snorts] [laughter] >> Dude, the suckback clause is a thing. Cuz that's a I want to know like we
12:42 we've all talked about that, but I wonder do you have that thing where you're like, "I don't like this this this, but God, it's so good." I was talking to this one girl and she was get She got She's really jealous. She's Vietnamese. Yeah. And then you know, just looking at just like liking a video, she gets so pissed. Oh my lord. And it turns you on, doesn't it? I'm like, "This is crazy." Cuz she's committed. Yeah, but man, that ████ was nice though. She sucks so good. Tell tell us tell us what happened. Uh it was We've been married. >> [laughter] >> Save us. Like I mean we were only together for like four months. But then it got to the point where she was like, if I didn't like all of her memes that she sent me or like like all of her stories, she'd get pissed. So you're saying all you have to do is double tap everything she sends you, you get bomb ass ████ you couldn't do that? It's more of a No. The >> [laughter] >> The stuff that she sent me was like dumb. You are not ready for marriage,
13:32 brother. When you have that kind of obsessive energy from a girl, is that attractive at all to you? It is. I mean I I think it's I think it would be nice, but also I'm like, "We got to talk every day?" Damn. >> But she sucked you like your butt hole wants to shoot through your pee hole. >> [laughter] >> Dude, she sucked so hard the sheets got caught in your butt hole, dude. Yeah. [laughter] And then after I'd be like, "This is fine." Cuz you're cramming them up there. Yeah, so then he does have the suckback clause like you. Yeah. And then like the next time it happens Yeah, the next time you're clear, you're like, "Ah, f███." So polling the room then, I think our favorite sexual activity is a ████ [laughter] because like it seems to be I think universally by guys. Yes. I think it is. I think that's like 50% of the relationship. >> [laughter] >> 50%? That's high. It's pretty up there. You break it up You break it up by 8%.
14:22 >> Penetration. >> [laughter] >> No, I think it's for ████ Yeah, I think 50% is everything you do to try to get a ████ and then the other 50% is like like plan planning your life OUT OR SOMETHING. [laughter] 50% IS IS FLIRTING to get the ████ and then the other 50 is actually getting it. >> [laughter] >> 100% relationship. Working to get a ████ and getting the ████ You take the trash out so hopefully you get a ████ later. >> [laughter] >> 99% begging. I you don't know. Hey, I washed the ████ out of them dishes before I ████ flew over here to get some head. >> [laughter] >> My dog. >> Wow, I'm learning so much. Did it work? Yeah. >> Hell yeah. And then your butt hole should I ████ MEAL PREPPED TOO, DUDE. I HOOKED HER. I was like, "I'm going to
15:12 make sure you're fed for a week." Jeez, man. What did she actually do? She threatened me with the ████ That's why I did it. >> It's a threat? Oh, that's hotter. Oh, she threatened you like, "I won't do it unless you do" No, she was like, "You want a ████ later?" I'm like, "Yes." And because out of the goodness of my heart How did she say that? She was like, "You want a ████ later?" Yeah, ████ later? Yeah yeah yeah. You want a little blowy later? And I was like, "Actually Yeah. It's a knife. >> [laughter] >> I do. I just said these ████ are rather uh straight right now. You want to crinkle them up your butt hole. [laughter] You want your butt hole to blow through YOUR PEE HOLE. >> [laughter] >> OH NO, YOU LIKE A VACUUM. OH, I JOE. >> [laughter] >> OH, JOE, YOU WANT TO GO TO THE BEAVER [screaming] PARTY. RIGHT RIGHT. BRING IT OVER HERE. RIGHT.
16:02 LET'S WATCH SOME CRICKET. Hannah would be ████ dying right now.
// end of tape