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You can buy it here and, yes, I really do sign every single one of them myself. I have signed thousands of copies since the book came out in late September. So go buy the book today if you want a copy to arrive before Christmas.
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If you have any anonymous mailbag questions you can email them to email@example.com, anonymity guaranteed. Okay, here we go.
“I need your advice on a situation at home. Here’s the background: my wife and I are mid-20’s and have been married for a couple of years. There’s another couple that we have both deemed our “best friends” that we see multiple times a week (both pre-kids right now). Recently my wife tells me that she had a dream where my best friend and I are both “pleasing” her. She seemed surprised that she had dreamt it but she just kind of brushed it off like no big deal.
Here’s where I should add that I’ve dreamt about her and her best friend (my best friend’s wife) multiple times but I’ve never mentioned it.
Here’s my question: After her dream, is it okay to tell her about mine now? I feel like it could end badly. I also feel if there was ever an opportune time to mention the idea of swinging, this would be the time right? And if I do, is there a chance she asks for me and my best friend to do what we did in her dream? Because that’s not the ideal threesome but is the trade off worth it? (That’s if our friends are even interested in this idea). What do you say, ole wise one?”
First, you can certainly tell your wife about your dream too. In fact, the next time you’re hooking up I’d explore it as a a fantasy you might share with one another. That’s probably the ideal time to tell her about your dream too. Hell, you can even say your dream happened after hers and say her dream must have unlocked a fantasy of yours as well.
Second, both of you may be interested in hooking up with this other couple, but it’s a big leap to assume that another married couple you’re friends with in their twenties also wants to swing and hook up with you. So I think you need to figure out whether this is a fun fantasy you guys can share and remain private between the two of you or if it’s something your wife would actually like to make happen in real life. There’s often a big difference between the two.
Then you need to think about how this might impact your relationship with the other couple and how you would broach a subject like this with them.
Third, you can’t only hook up with the husband. Either you both hook up as couples and swap with one another or you don’t do it at all.
My advice on what to do if you’re both interested in exploring it?
Let the women hash it out over drinks one night and let your wife see if they have any interest in a group sex playdate with the two of you.
If the answer is yes, I think they can take it from there.
If two good looking women start kissing while everyone’s drinking I’ve never seen or heard of two men who have ever thought that was a bad idea.
“My wife and I are in our early to mid 40’s, 2 little girls (7 and 5). as with most couples in this situation. living life has taken a backseat to raising kids, stressful jobs, etc. My wife has told me she is unhappy cause my temper is shorter and I am grumpy a lot of the time (not screaming or hitting mad, just generally dissatisfied). She wants me to change my attitude, which i am working on.
Well I told her one of the reasons I am unhappy is because the sex has fallen way off since he girls were born. So we both decided to change our attitudes to make our life better. So far so good. I told her that there was no reason why we two consenting married adults cannot try to fulfill our wildest sexual desires. So I told her my desires, nothing too out there, and we have been having a lot of fun with it. Well I also want her to be happy so I asked her what her sexual desires were. And thus we come to the question. She wants to use a strapon with me. Now I am razor straight and had never even considered it before, and I cant really back out at this point without causing some serous marital problems. So should I just smile and go for it? Or is this just too weird? is this a normal thing for women to want?”
I’m not an expert on this — thankfully — but I think every woman who wants to wear a strap on and fuck her husband in the ass hates his guts.
So I think your wife probably hates you.
I just don’t buy into the idea that this is about sexual pleasure for her, I think it’s about humiliating you. This seems like the kind of story that comes up after you’re divorced when your wife is sitting around with her girlfriends and says, “I knew marital counseling wasn’t going to work, but he wanted to fulfill all our sexual fantasties so before we got divorced I strapped on a dildo and fucked him in the ass until he squeeled like a pig.”
Honestly, that’s a huge badass way to go out. I think that story would absolutely KILL on the divorced women wine and cheese circuit.
So I think if you’re going to get fucked in the ass by your wife, you have to up the fantasy quotient here. At an absolute minimum I think you need to bring a third girl into the bedroom before you get fucked in the ass. You can’t be trading her dressing up like a cheerleader for your anal virginity.
That’s just an awful trade, like Jon Gruden giving up Khalil Mack and Amari Cooper for a single first rounder each and putting the Bears and Cowboys in the playoffs as a result. Or the Boston Red Sox selling Babe Ruth for cash.
You don’t want to spend the rest of your life with your own version of the Curse of the Bambino, anal sex version.
“Been following you for a long time and a huge fan. I have a question for you. My girlfriend and I have been dating for a little over a year and recently moved to a new city together and live in a one bedroom apartment. We both started working and everything is going great.
Here’s the issue. She asked if her guy friend from high school who she “knows really well and would never try anything,” can stay at our place for a football game in our town. Normally I wouldn’t care. My girlfriend is kinda a tom boy and in school, she got along great with my friends and vice versa so it’s not like I’m all anti her having male friends. However, I’m going to be out of town that weekend and therefore it would be just her and him in the apartment.
Now, I am not the jealous type and am very confident in our relationship as it is but still, this would be a dude essentially sleeping in my apartment without me there. We’re in a safe financial position (both of us are in our mid-twenties already making six-figures) and are looking towards the future so it’s not that I don’t trust her. Would it not just be the most beta move to allow her to invite him over? I’m leaning towards telling her no because, well, obvious reasons I just don’t want a freakin guy staying in my apartment with my GF unless it’s her brother or dad or something like that. How do I essentially say no without her getting pissed and, if she does get pissed, is that the most fucked up thing to get pissed over?”
I definitely think you say no.
Look, it could be this guy has completely innocent intentions, but what if he doesn’t? What if he, like most guys I’ve ever known, is perfectly willing to sleep with a random girl he’s sharing an apartment with if the opportunity arose? That’s especially the case if your girlfriend is hot, in which case there is a 100% chance he’s willing to sleep with her no matter what he says otherwise. (I don’t believe men are ever platonic friends with attractive women. I think women can definitely be platonic friends with men, but I think men are always willing to sleep with attractive women, even if they are good friends with them and women think they would “never try anything.” Do you know how many kids – and marriages — there are in America from guys that women thought would “never try anything?” This dude, in my opinion, is like a friend buzzard on the side of the road, willing to pounce at the first sign of potential sexual availability from your girlfriend.)
I’m even suspicious of the staying over angle. Come on, he doesn’t have a single dude friend he can stay with in the city instead? He can’t get a hotel room? I’m just not buying it, I don’t trust him or his intentions.
Stand your ground, he can’t stay there when you’re not there.
If your girlfriend is mad at you for this opinion, just say you’re applying the relationship golden rule, you’d never ask her to have a girlfriend of yours stay over at the apartment when she wasn’t there. (Of course you wouldn’t do this because you would totally try to sleep with this girl if she were willing to sleep with you and would totally assume that your girlfriend would think this was what you were trying to do too. Confession: I have several good girlfriends from high school and college, but all of them were unwilling to sleep with me. I totally respected their decision, I wouldn’t want to sleep with me either, but the only reason I ever became friends with them was because I tried to sleep with them and they rejected me.)
Just know that once you make this decision your girlfriend will keep score and no girlfriend of yours will ever be able to stay in your house and visit for the rest of your lives together. Not ever. Women never forget shit like this. You could be 98 years old and you’re inviting another 98 year old to stay at your place because her husband just died and your wife would be like, “Oh, no you don’t. Remember 70 years ago when you didn’t let Tim stay over at our place? That harlot can stay somewhere else!”
So just be aware that you’re making a decision for life, but also know that you’re definitely making the right decision.
“About 7 months ago I went with a buddy on a vacation oversees and I met this girl (who is American). We met the first night and stayed at the same hostel, and ended up having a bunch of sex over the course of 3-4 days.
When we went our separate ways we stayed in contact through social media, snap chats, and occasional texts.
A few months back she posted on social media about needing a travel partner for an upcoming trip and I volunteered my services. Last week, the trip is booked for just the two of us in a tropical region. Leading up to the trip I figured that we would pick up where we left off. We spend the first night together and she didn’t give me any vibes that she was really interested, so finally on the second day I just put it out there and asked if she wanted to have sex.
She had a confused look on her face and simply said no. I felt pretty awkward about it and kind of ruined that night. The next day I brought it back up and apologized for making it awkward, and she basically said it was fine and that she was just on her period (which I don’t think is true) and that maybe we could have sex in a few days. Things were a little less awkward after that and after a few days we ended up having sex a few times. The sex really wasn’t that good and it seemed like she really wasn’t interested in doing it. The questions I have are: 1.) Was I in the wrong to assume that we were going to be having sex on the trip? 2.) Is this a potential “Me Too” moment where the only reason she had sex with me is because I made her feel obligated to?”
You didn’t do anything wrong, but this girl wants more than a sexual relationship with you.
She probably regrets sleeping with you that quickly and hoped that when you went on vacation together something more would be kindled and you might end up in a legitimate relationship. When you got on vacation you gave off the vibe that you weren’t interested in anything more serious than casual sex and this was a turn off to her, which is why she didn’t sleep with you the first night.
When you badgered her about having sex, this was even more of a turn off to her and she hoped that by not sleeping with you it would cause you to realize that you actually liked her for something more than sex.
When this didn’t happen eventually she felt guilty she’d gone on vacation with you and not had sex so she had disinterested, feeling obligated to have vacation sex with the guy I’m with sex, and I would suspect that your relationship is pretty much over now.
She wants to find a guy for a serious relationship and now she knows you aren’t that guy.
(Note: I could be wrong here, but in addition to being the King Solomon of the Internet I also think I’m better at deciphering female emotional moves than 99.9% of men in America.)
Having said all of this, this IS NOT a me too thing. If women sleeping with men out of obligation or guilt is a me too violation now, this means that like 88% of all marital sex after children are no longer being conceived is a me too violation as well.
And for the women reading this, yes, every man really does expect to have sex on every day of the vacation, particularly when kids aren’t involved, otherwise it’s not a vacation to us.
So if you’re going on vacation with a man and think “you’re just friends” just be aware that he doesn’t believe that.
The sex is why he’s taking the trip with you.
Send your anonymous mailbag questions to firstname.lastname@example.org and if you want an autographed copy of my book to arrive before Christmas, go buy it today becasue it’s the last day we can guarantee the book will arrive before Christmas.