Man #33, Just Because There’s a Hole…Part 2

23 08 2012

So, if you were here yesterday and you read Man #33, Just Because There’s a Hole…Part 1, you should have a pretty good idea that we will be covering some delicate territory today, and by delicate territory I mean where your poop comes out. I would like to warn my readers that today we’re going to be moving into an NC-17 rated or maybe even X-rated topic just because I think what happened on my date with Man #33 needs some discussion…

…and I need a cocktail.

I don’t care what you say. Part of the reason I have a blog is so I don’t have to deal with this shit alone. You should go mix yourself a cocktail too.

I’ll take a break here while people get their drinks and anyone who hasn’t read Man #33, Part 1 goes and gets up to speed. After reading Part 1, you have a choice. You can either continue reading at your own risk, or you can opt out until tomorrow when I will be posting pictures of kittens.


So, where were we?

Oh, yes. Man #33 and I were conversing at Starbuck’s when he suddenly asked me if I would be willing to stick a finger in his ass.

Then I promptly shot chai out of my nose. You might say I was unprepared for the question.

And this, THIS, male readers, THIS is why I hate being asked on a coffee date. It’s not because I’m some prissy bitch who thinks a man needs to spend a bunch of money on dinner. It’s because this is the kind of shit that happens on coffee dates. Coffee dates are for freaky, little men who put as little effort as possible into trying to get laid. They’re for men who are not interested in a relationship and who can’t be bothered trying to impress a woman with dinner, because these men really just want to get fucked in some odd fashion.

I have had several girlfriends tell me they were propositioned for sex in the most inappropriate, why-don’t-you-just-go-pay-a -prostitute way, after merely having coffee with a guy. Even from my own dating chronicles I’ve had two coffee dates now that have turned almost immediately inappropriate, Man #26, The “Masseur” and Man #33, Sphincter Probing Guy. I can understand that dating can be rough on men’s wallets, but the coffee date just reeks of a cheap creep who has some freaky thing he wants to ask for or do and just doesn’t give a shit.

And guys, don’t get all pissy with me for despising the coffee date. Get pissed at your stupid brethren with no game who have fucked up the coffee date for the rest of you. It’s their fault, not mine.

Whew! Ok. Now that I have that off my chest, you might be wondering how I responded to Man #33.

Well, first, I wiped chai from my nose, and since shooting hot chai into the upper regions of my nasal cavity made my eyes water a little, I had to dry my eyes too. Then, with my usual sarcasm sort of stunned out of me, but still inappropriately laughing on the inside, I dryly said, “No, I can’t do that for you,” while trying not to laugh because that would have forced more chai up my nose.

“Ok,” he said, “I had to ask.”

It was strange. He looked so normal. I scrunched up my brow, looked at him quizzically for a second, and asked, “Does this usually work for you?”

“Not usually, but sometimes,” he said.

And there you have it. The fact that occasionally Man #33 will find a woman who is willing to stick a finger in his ass has given him the “confidence” (I’m not sure that’s the right word) to go out on coffee dates and ask women to probe him.

My friend, Sam, asked if he was German.

“He seems very efficient,” she said, “if it’s something he has to have, it’s probably better to ask right away than get 6 dates in and find out the woman won’t do it.”

True enough.

After my date with Man #33, I got to thinking about this ass probing thing. Obviously, this is something that is so important to Man #33 that he has dropped any sense of social decorum, and while, publicly, most heterosexual men act all bravado and jittery about having things stuck up their asses, privately, I am hearing about men wanting this more and more.

I also have enough gay friends to know that the male g-spot can best be accessed via the anus, and stimulating it when a man is about to cum can give him one powerful orgasm.

If I actually chose to wield that kind of power, I might scare myself. (Sorry. That was my inside voice.)

At this point, I’m not saying I’m pro or con to sticking a finger in a man’s ass. I have to think this through. Come along with me on my thought process, please, and bring your cocktail. You’re going to need it.

So, going back to what I know from my gay friends, I know enough to know that a prostate or male g-spot orgasm is supposed to be the best. It’s supposed to make a man’s orgasm stronger and more intense. However, what I have also heard is that in the midst of male-on-male lovemaking things can start to smell…well…a little shitty.

Now, again, from conversations with my gay friends, I know there are some preparatory things that can be done to make everything a little more presentable and pleasant, maybe a shower, maybe some waxing or a shave, maybe some anal bleaching, maybe an enema…maybe you don’t eat the frijoles at the Mexican restaurant. You see what I mean, right?

And here’s my problem. Half the time heterosexual men can’t even be trusted to shower their sweaty ball sack before asking for a blow job. How the hell can we expect that they will wipe their ass, let alone have an enema, before asking you to stick a finger up their butt?

And, I realize that not all homosexual men take these steps either, but I do know that they tend to pay a lot more attention to making the ass presentable than their hetero counterparts.

It’s all about hygiene, people…and orgasms…, which brings me to another thought. What is the best way to stick a finger in a man’s ass when having sex without sacrificing your own orgasm? Like, let’s say you’re in missionary position…do you reach over the back or under the balls to access the man’s ass? I don’t think my arms are that long. Or, what if you’re on top of him and you try to reach back to stick your finger in his ass? That not only seems somewhat acrobatic, but it would also cause you to lean back, taking friction off of you clit, and again, you might be sacrificing your own orgasm to give him his.

I consulted the Kama Sutra on this and none of the positions are shown with a finger in the man’s ass. I think a sideways, kind of scissor position might work, and make it easy to digitize the sphincter, but then what about my clit? Is it going to get what it needs?

You see, I may not be a prissy bitch, but when it comes to my orgasm, I am a selfish bitch.

And I did a little internet research…if you are reading this at work, I don’t recommend searching for “male g-spot orgasm” or “male prostate massage” and opening any links right now. You could get in big trouble.

But I searched the internet, for how a woman could give a man a g-spot orgasm, and as I suspected, most of what I found were images and videos of men on all fours, hairy ass in the air, junk hanging down, with a woman standing behind them with a huge butt plug and some lube.

See what I mean? Where would my clit be in all of this? Standing behind a man dressed as a dominatrix perhaps.


Not really my thing. That’s not going to be sexy or romantic for me. In fact, standing there, looking at my man (when I finally find one) in such a vulnerable position is probably going to be a huge turn off for me.

Ok, but there are supposedly health reasons for “milking” the prostate.” This is something else you should not Google while at work. Apparently, regular milking of the prostate has benefits that keep the prostate healthy and prevent prostate disease by regularly emptying the contents of the prostate gland. As it turns out, your standard lovemaking ejaculation doesn’t get everything emptied out, but a prostate milking does.

Huh. Well, you want your man to be healthy, right? So is this something you want him to do on his own or do you want to be involved?

So, then I had to give this some thought. Let’s just say, hypothetically, that you are in a relationship where your man is a very giving lover. He goes down on you regularly, and is just as interested in your orgasm as you are. What if you want to return the favor by helping him get a male g-spot orgasm?

So, that question led me to a website called Mangasm. This company sells a wide variety of male sex toys, including prostate stimulators. Now, I’m a little embarrassed to admit that I watched a couple of the videos, but, I think, a man could insert one of these gadgets before having sex, do all the things needed to get his girl off, and still get his g-spot orgasm too.

A fucking win-win.

So here’s the bottom line. Asking someone to stick a finger up your ass on a first date is WRONG. However, what two consenting adults choose to do to bring each other pleasure in the privacy of their bedroom is not for me to judge, and obviously there are tools out there to make it happen and still preserve your manicure.

Finally, I feel I need to apologize to my more squeamish readers. Did you know that you can kill a tree using copper nails?

It’s true. Given that copper can kill a whole tree, it’s quite possible that the two weeks that copper penny sat in close proximity to my brain as a toddler has caused some irreparable damage. This may account for the twisted way in which my brain works.

However, a couple of years ago, I took the Myers Briggs Personality Assessment. I’m pretty sure I’ve mentioned this before. It turns out I am an INTJ. This is what the description of my personality type says:

INTJ Have original minds and great drive for implementing their ideas and achieving their goals. Quickly see patterns in external events and develop long-range explanatory perspectives. When committed, organize a job and carry it through. Skeptical and independent, have high standards of competence and performance – for themselves and others.”

I guess this explains why dual orgasms are so important to me, but it also helps explain why my mind ran through all of these different mangasm possibilities. Wikipedia also has a nice article on the INTJ personality. I’ll just apologize again for how my mind works.

Basically, if we were all sitting around a conference room, trying to decide whether or not to put a finger in a man’s ass, I would be the person, at the last minute, just as everyone else decides to go for it, who will slowly raise a hand and say, “We should get some latex gloves…


…a hangnail.”



13 responses

23 08 2012
Allison Peacock (@Allison_Peacock)

Don’t go hating on the coffee date. See…now totally circumventing the idiots-who-ask-dumb-questions-on-a-first-date thing I actually LIKE coffee dates.

For me there have been far too many awkward dinners with men I knew in the first minute I’d not go out with again. And if to boot the chemistry is bad or awkward, or they have few socially redeeming qualities – a coffee date is over quickly, no harm, no foul.

Think of it this way, what if you had been stuck at DINNER for two hours with this guy? Would that have made it more palatable? The point is…freaks are freaks no matter the setting.

So the setting is about me. And about how much I’ll invest without having spent time together in the same room with someone I don’t already know. The more discriminating you get and the closer you get to #100 I’m sure you won’t have these things happen. But, darlin’, at 67 to go, do you want to have all those dinners with potential freaks!?

Don’t throw the baby out with the bath water. Just ditch the freaks!

23 08 2012

I will just refer you to Ditto Ditto’s comment after Man #33, Just Because There’s a Hole…Part 1. It is my experience that men who are not interested in a relationship opt for the coffee date. I agree that dinner is a bit much, but I have had too many bad coffee dates.

23 08 2012

Guess if he didn’t ask, he’d never know…. better to find that kind of thing out on a first date, than waste your time getting to know him for 6 months and then have him spring it on you!

Love reading your blogs… always look forward to what’s happening… NEXT..

23 08 2012

Yeah, I suppose. It’s just kind of rude to spring that on a woman right away like that.

23 08 2012

We gay guys never have that problem, if you know what I mean:)

I really enjoy reading your blog. I look forward to your future posts.

23 08 2012


24 08 2012
Elder Baud

Excellent, thorough analysis. I think I learned a few things.

24 08 2012

I know I learned a lot while doing my research.

24 08 2012

holy crap :o)

graphic, yet informative blog (can’t say you didn’t warn us)!

24 08 2012

I hope you had your cocktail.

24 08 2012
Man #33, As Promised, Part 3 « My Dating Prescription

[…] in Man #33, Just Because There’s a Hole…Part 2, I didn’t promise anything in the way of kittens, but given that I took the blog beyond its […]

25 03 2013

Love your blog. I’m not giving up on the coffee date though. I don’t see how you can give up on it either. A hundred dinners, movies, wine tastings, and after work drinks with people you haven’t even met before? No thanks.

25 03 2013

I’m haven’t given it up. I don’t like them, but I go. Besides, 100 coffee dates would be pretty damn boring.

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