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Q: I recently let this girl kiss me after she blew me and I almost threw up. It got me thinking, is there anything more gross than that? And what's the most disgusting thing you've ever done while in name of sex?
A: How much time ya got?
There have been some circumstances where I've had to do certain "things," overcome certain "obstacles," that I'm not particularly proud or ashamed of. Not to say I've done anything just "for the story" or that there was any "shit play" involved (that's gross, airborne fecal matter has no place in my life). But yeah, I've made some morally questionable and reprehensible decisions out of necessity, because ME SO HORNY.
Anyway, here is one of my most egregious offenses against common decency:
Five years ago, on a Thursday night, I'm out to dinner with clients from a publicly traded hedge fund in Manhattan. We're at one of the more highly regarded sushi establishments in the city, and since the meal was on our company's dime we drank like pigs. Every last one of us.
After the bill was paid and the higher-ups from both sides decided to split for the night, all of us plebes still wanted to keep getting after it, you know, to really make Friday HURT. So off we went to a bar called Puck Fair to continue our alcoholic onslaught.
We're at the fair of pucks -- I don't know how long, I was drunk and had no concept of time -- when from virtually nowhere, this mid 30's coug comes walking our way. She was spicy; wearing a tight red dress, sexy heels, and her makeup looked like it was applied with a shotgun. In other words, she was perfect.
I don't remember what we talked about or how the introduction was even made, but I do remember buying her a drink and then seconds later making out with her in the middle of a sparsely crowded bar. (Disgusting Offense #1)
I knew what had to be done; I invited her to come back to my place. She countered and insisted we need to go to her place. Says something about her "roommate." Since I didn't give a shit if we fucked in a bed or on a pile of burning trash, we hail a cab and head to her apartment.
She lived uptown, which meant we had about a 15-minute can ride from Puck Fair. Not one to squander time, my would-be concubine starts making out with me while clawing at my dick from outside my pants. (Didn't want to pull my dick out in the cab, because you know, she's such a lady.) Since I'm a gentleman, I followed suit and pulled the over- the-skirt rub move. Really got after it. Tenderly, of course.
When we got out of the cab, and walked into her building, she quickly acknowledged the existence of her doorman and we hit the elevator.
That's when the gloves came off. And by that I mean, on the ride up in her elevator, I put my hand down her underwear, discovered a tampon string, and yanked it the fuck out. Clearly that couldn't wait till we got in her apartment. She took it in stride. Looking back, her choice to wear a red dress seems a lot more calculated than it did at the time. (Disgusting Offense #2)
When we got to her floor, we got out of the elevator and, tampon still in my hand, I flung it down the hallway. I don't know what I was thinking, or why I did it, but I flung that fucker like a fifth grader flings a ketchup packet across the cafeteria during lunch. Didn't even see where it landed. Didn't care. It was out of my life forever. (Disgusting Offense #3)
As we walk into her apartment, I'm thinking this will be 20-minutes max; get in, get out, wash my dick with bleach, and get on with my life.
The moment we open the door, my eyes catch eyes with an older lady sitting on the couch, then they shift to a corner of the room and notice a baby sleeping in a crib. THE FUCK!?
The old lady is her babysitter. She introduces me (awkward, unnecessary), pays her, and then she leaves thinking terrible old lady thoughts. So now it’s me, this chick, and what appears to be her sleeping infant.
After no more than a minute of “what a cute kid” pleasantries, we went into her bedroom and I did my best to fuck her without thinking about the blood on my condom-less junk, her sleeping baby, or the C-section scar that was smiling at me. (Disgusting Offense #4, on many levels).
When it was done, I went home and immediately went to bed...without washing my dick. (Disgusting Offense #5)
It was a nice evening by most standards.
Q: Should a bro like to cuddle?
I'm not talking about cuddling up next to that slam pig from last weekend but if I have a chick I actually think is cool, after all that rolling around, when it’s time for bed I always go for the spoon. I know dudes who don't at all. I would feel like a dick just showing them the cold shoulder. Most girls melt when you pull that freshly tapped ass up into you. That make me weird?
A: What’s this? Acting like a human being by showing some common, post-coital courtesy to a girl you kind of respect? You fucking disgrace. You're out of the goddamn will, stupid pansy.
Sorry, I got carried away up there. Reacted the same way my dad did when I was in college and he figured out that I trimmed my chest hair. Guy lost his shit, said some things I’m sure he regrets. Take me out of the will? What is he nuts?!?
Truth is, cuddling up to a chick that isn’t just “some bitch” doesn’t make you weird. It makes you not seem like a one-track-minded scumbag to her. Although that approach DID work wonders for Patrick Bateman, most dudes will not go far with it. Moreover, some girls require something other than your barely serviceable, semi-soft 6-incher for them to keep sleeping with you. Could be dinners, drinks, or in some cases pillow talk and spoonery. Just be careful that these innocent spoon seshes don't blindside you by turning into a full-blown relationship.
Q: So, I've had this girlfriend now for a year and six months, I like her, but nothing more just because we're two different people. My question is, what's the best way to break up with her?
Side note: I might have cancer, so I don't really know what to do with that either.
A: Always get right to the point. Don’t let her refute your rational why you want to break up or try to talk you into “working on it” because you’re obviously past that. So many dudes get caught up in the tears and fail to completely pull the trigger because they feel bad their breaking someone’s heart. Yeah, it sucks, but what also sucks is making a girl cry, staying with her because you’re a pussy, and having to now deal with a chick that thinks you don’t want to be with her.
Breaking up with a girl is no time for cowardice. It’s like ripping a Band-Aid off a freakishly hairy leg; the moment is going to suck, but it will end faster if you just do it quickly.
Be semi-truthful (she doesn’t need to know every gory detail as to why you think she’s just awful) and then don’t contact her for weeks. The decent guy in you is going to say, “maybe I should see how Sarah is picking up the pieces.” DON’T. She will get over it. Just make sure you point out all the reasons why the two of you as a pair don’t work when you break it off. Over time, and with distance, she’ll realize these things as well.
As for the whole cancer thing, GO TO A DOCTOR. The sooner you know the better (obvious). Also, don’t go on WebMD, everyone that goes on WedMD loses their shit because every symptom leads to Cancer, MS, Lou Gehrig’s disease or HIV. I’ve honestly misdiagnosed myself so many times with HIV that it’s embarrassing.
Q: Seriously J.Camm, pull your thumb out of your ass and answer one of my damn questions and this question is of the upmost priority. I am a bro in my mid 20s and I have (sadly) started to move out of my boning chicks with self-esteem issues and into the “I want a relationship” phase. That isn’t the issue. I met a girl who is a solid 7.5 as far as looks go. I know I could easily find a hotter chick but everything else about her is perfect girlfriend material. She loves sports, can cook, all-around solid catch. We exchanged numbers and have been on a couple dates and texting daily. Finally I had this girl alone for the first time and things started to get hot and heavy pretty fast. Right at the point where I would reach for a condom this girl takes my dick and starts putting it in raw dog. I just went with it. Half way through I asked if she was on the pill or if I needed to pull out. She told me I could cum inside her so obviously I pounded it out and busted a huge load in her. So the question is. . . should I take it as a compliment that this girl let me creampie her the first time we did it or should I be more worried about who else she has had unprotected sex with? Would this be a deal breaker or just icing on the cake? As a sidenote, her vag was tight so I had no reason to believe she was a complete slut.
A: Don't sass me, you son of a bitch. I get so many questions that it is impossible to answer them all. Well, not impossible, but it would take more time than I have to give. Consider it poor luck, or poor submissions on your part, that week after week I continue to overlook yours. This week, I'm answering yours because you insulted me, which, as everyone knows, is the way to my heart.
What fascinates me is you’re only concerned about contracting an STD. I guess there are some you can’t do away with and that abortions are always an option, but what if you DID get this girl pregnant and she wanted to keep the kid? I don’t have either, but I’d venture to guess having a child when you don’t want one has to be worse than herpes. At least herpes leaves for a while, a kid never does.
As far as I’m concerned, the fact that she wants it raw doesn’t make her a slut, it makes her human – unless she is trying to get pregnant without telling you, then it makes her a MONSTER. My guess is she trusts you, likes you, and wants to be more than just the girl you bang twice a week. That's why she let you do what you did.
Lastly, the elasticity of her vagina won’t really tell you if she’s a whore or not. I mean, sure it could, but for a mid 20's chick to be ruined, that thing would have to have gone to hell and back to not return to its normal state after sex. Vags are resilient like that.
[Girl in Red Dress image via ShutterStock]