Ask Dr. Tony vol. 17

Ahhh, it’s been so long. The doctor is once again back in effect , here to answer all of your questions concerning love and shit like that. As always, I’m not licensed in anything. Not even driving. But, I’d like to think I have a keen grasp on reality and the ability to tell you how it is with honesty and balance. So, if you have more questions like the ones below, send them my way: It’s anonymous and can only help in the long run.
Okay? great.

I gotta Que…I’ve been seeing this guy for a couple months. He’s a little more invested than I am and he’s starting to get pretty relationship-y. I like him a lot, but I want to keep it casual for now. He has a kid and I’m not quite sure yet if I’m down with that. I’ve been completely upfront with him on how I feel though. Anyways, we’ve started having deep convos about our past relationships and that. I find myself wanting to know more and ask questions. For example; he’s a super attractive/charismatic guy and I’m really curious to know how many notches he has on his bed post. What’s the etiquette on questions like this? And if I just want to keep this relationship casual, is it any of my business? He has no problem asking me these types of questions, and for the most part I’ve been answering them. But if I start asking them am I sending out the wrong message?

first off, LOL @ “for the most part I’ve been answering them”. You know you’re lying to him about your past! It’s all good, I just thought that was funny.

As for your question, personally, I don’t think peoples pasts are a big deal. I think asking about past sexual partners (in a “How many people have you slept with?” kinda way and not in a detailed “I need to know everything that your genitals has done” kinda way) is harmless and not that invasive to anyone who’s an adult. Seeing as he has a kid, I’d say the skeletons in his closet can only go so deep. If he fucked a 1000 girls, who cares? He’s got a kid now so things are probably different.
That said, some people like to play their cards close to their chest. Some people get offended at the idea of even discussing such matters. some people are over protective, whiny pussies.
I think if he’s asking you shit and you’re answering (even if you are bending truths), you can ask him right back. I mean, you’re curious, right? Technically, it’s not any of your business but if you think you can handle whatever info he gives you like an adult, then I don’t see why not. HOWEVER, if you’re just doing it to bait him into an argument or have things to possibly hold over him in the future, you should just not do it. Also, if you’re doing that, you’re the worst.
As for asking these questions and keeping things casual, I don’t think that’s a big deal either. I’ve asked girls i’ve never even hooked up with those questions. The key is keeping the dialouge casual and not making him feel like he’s being judged. I’d like to think your typical male doesn’t read too much into those type on inquiries. After all, what’s leading him on when you’re already sleeping with him? As long as you’re still fucking him, he’s gonna still think you like him at least a little. So, perhaps, if you’re worried abut that and not that serious about him, you should consider that before anything involving personal questions.

I know this guy who is my age, mid twenties, and he is dating this old woman (on her late fifties).
Man, I see the like every week partying or whatever and I mean, what the fuck????

That’s my question hahaha

yeah, pretty much.. young people with old people (I mean +30 years older than them)

Personally, I don’t get it. Whenever I see a couple like that i assume the older person is going through a stage and the younger person is dealing with some childhood trauma via their dating choices. Daddy didn’t love you. Daddy loved you TOO much. Mommy left. Uncle bobby was a piece of shit. Whatever the case, a lot of people have things happen to them that seems to suspend them in time, emotionally. To me, any person that’s willing to date someone so extremely older than them has issues. Even if they claim some bullshit like “You don’t find love, love finds you!” as an explanation, I’m not buying it. They’re either fucked in the head or devious.
That said, if it’s just some kinda sexual exploration thing on both sides, then I see no harm in it. I mean, shit, granny porn exists for a reason. If I’m a young dude who’s into old bags, why would I not have sex with them? And you can’t blame the old people for wanting to have sex with younger people. That’s pretty standard across the board. However, when i see some “deep love” shit between people of extremely different ages, I’m not buying what their selling. I buy that one of them is into it earnestly but the other is either waiting for money or enjoying the fruits of youth.

What do you/ most men think about female ejaculation or “squirting”? I’m a squirter (I absolutely hate that word) and I don’t know whether to flaunt it in bed or hide it. Sex is a huge deal to me. I don’t sleep with many guys, but if I find a person that I have great sex with, I want to make the most of it. I can be pretty shy, but I’m very outgoing when it comes to sex. The best sex I’ve ever had has been when I’ve allowed myself to squirt. I love it. But, is it a turn off? Or do guys like this?

I’d say there are two camps on this. The guys who like it and the guys who don’t (duh). However, I feel like most men are into it. Not even as a spectacle but as a source of pride that we can make a girl do that. The guys who don’t like it are gonna be the uptight guys who are weirded out by sex to begin with. The types who don’t REALLY like vagina’s but are still attracted to women. Does that make sense? I’m not talking about closeted gay dudes. I’m talking about guys who like sex and the act of putting their dick in a vagina but, beyond that, don’t really wanna deal with the vagina. Those dudes might be turned off by it. Luckily for you, they are the minority.
I’ve had a little experience with a squirter and the first time she did it, i felt like i had unlocked some magical rubik’s cube in her pussy. I was psyched. Sure, it was a little messy but I think most dudes will exchange that for knowing that they were able to make this rare thing happen with a girl. We are a very ego driven breed. Even in sex. So when we can achieve something that not every guy can, that’s a good deal for us. Just as long as it’s not spraying in my face like an open fire hydrant. Then i feel like it might get a little weird.

Alright Block, here’s what I got going on. I met this friend of my cousins a few months ago, and promptly told my cuz that i was gonna have to holler at her friend. She warned me to be careful, because she had gotten divorced not too long ago (bout a year) from a dude who turned out to have some secret drug addiction. So I got her to go to a few shows with me, led to dinner and a movie, which ended up in my bed rollin around till bout 5am. Good shit. so we’ve been kicking it pretty regularly since, and i can tell she genuinely likes me. I really do like her, but my emotions are a little harbored bc im not sure what to expect with this chick. She’s smoking hot, bangin body, great job, traveled the world, smart as fuck, listens to good music, has a great perspective on life, blah blah blah, she’s basically way out of my league. Obviously she had a rough, yet very short marriage. Here’s the kicker: I’m 27, she’s 39…. what should I be expecting out of this? I’m kinda looking for something steady, grown tired of playing the field lately. But I don’t know what to think about seriously dating someone who could’ve been my babysitter. I feel like I should just hold on for the ride and see how long it lasts. She’s already inviting me to things that are 2 months away. Hit me with your thoughts

Well, this relates to the early question. Personally, I would not put too much stake into the longevity of this relationship. I’d just enjoy it for what it is. The thing is, she’s 39 NOW. In ten years, she’s almost 50. Seeing as you’re 29 and not a recent divorcee of a drug addict, there’s no way your heads aren’t in different places. You might wanna get married and have kids one day, right? Well guess who won’t be able to have kids? Also, You allude that that divorce being messy so I can somewhat assume she’s been through some shit. She might be simply having fun with some young dude or she might be clinging to anything she can cause she was so devastated by her divorce. Regardless, i don’t see room for long term stability in a relationship like this, considering the details. She’s wounded. It’s not her fault but she is. If i were you, I’d keep enjoying her time but know that , eventually, it will have to come to a close.

What’s with “girl talk”?? When a group of guys are talking and a girl they are friends with walks in, even if it’s some greasy / deeply offensive talk, they may pause for a millisecond but will generally carry on. When a guy walks in on a bunch of girls talking, even if he’s good friends with them, a lot of the time they will zip it up and look at you like they were just about to solve world famine but you farked it up by walking in. What is with that?

I don’t think it’s that black and white. I think, on both sides, there’s a time to zip it up and time to open up a conversation between the sexes. Chances are, if a room or girls clam up when you enter the room their either in the midst of discussing some salacious shit they did or they’re talking about you (or someone you know). As a self appointed and un-educated sociologist, I’ve been privy to all sorts of girl talk. I’d like to think I’ve sat in on the real thing more than a few times. I can tell you that it’s never as fucked up as what guys talk about but it’s far more detailed. The things they care about don’t even register on our scale. I’m not saying girls are sitting in salons talking about their feelings. Not at all. They’re talking about the same shit we are, just completely differently. For every frank discussion of dudes dick sizes (which they do talk about, sorry!) , there’s a whole other side of them explaining minute details that made huge differences to them that I’d venture to guess most men didn’t even realize existed.
I think it all comes down to women just being more sensitive to the situation. Even though what they’re talking about might not bother the man walking into the room, they might assume it does. So the talk ends. But, honestly, I think it’s more a case of “This motherfucker that owns a dick does not get to hear this info”. Regardless, let the bitches talk, bro.

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