I had said previously that I was running low on cash to support my escort hobby. Trying to find a woman who was going through a midlife crisis didn’t quite pan out, so I was trying to think of my options. Sugar dating was something to look into.

I know what you’re thinking. If I couldn’t afford an escort for a few hundred dollars, how could I afford a sugar baby? Through my research online, it seemed that women want a sugar daddy for different reasons and have varying expectations of the “sugar” they receive. Some want to unfettered access to your Black Card, others just want you to take them out for a nice dinner.

So again I turned to the Google machine to find the appropriate sugar dating website. And again, the results vary greatly. There are two top players as far as I’m concerned: Arrangement Finders and Seeking Arrangement. Every other site I think you can ignore. (As an aside Established Men is a clone of Arrangement Finders. Same exact site, same users, and you can log into either one with your AF login.) I will review both sites later on.

But let me back up for a bit. For those who don’t know what sugar dating is, let me explain. You know when you see an older gentleman with salt and pepper hair towing in his arm a much younger and vivacious coed? That is what sugar dating is. A relationship in exchange for compensation in the form of gifts and/or allowances.

Hugh Hefner is a sugar daddy. He is known to have three to 15 live-in sugar babies at once. He pays them only about $1,000 per week while providing them room and board.

I’m not Hugh Hefner and my budget is much smaller than $4,000 per month per girl. There are other sugar daddies out there who make a lot more than I do. Financiers, actors, businessmen. But as someone who is firmly in the upper middle class with my income, and someone who supports a wife and two kids, I really don’t have a whole lot left for sugar daddying. But I might have enough for the right girl.

The first “chapter” of this site was about escorts. Then we moved onto affairs, albeit very briefly. And the next chapter will be primarily about sugar dating. Stay tuned my friends.


From its stunt-driven advertising to its purported 20 million members in over 25 countries, Ashley Madison certainly has one of the highest profiles in adult dating sites. It was made specifically to enable extramarital affairs, and the brand itself caters to women with its bright colors, using a palette of pinks and purples.

Needless to say, it seems like if you’re looking for something extra on the side, this is the place to be. Like almost all dating sites, you can browse but you cannot contact other members. In order to do that, you must purchase credits (choose from three bundles of 100, 500, and 1,000). Messages to other members will cost you 5 credits, and instant message sessions cost even more. So choose your plan wisely.

I signed up with the hope of meeting other like-minded women in their late-30s and early 40s. Essentially plus or minus five years from my age, thinking that that’s the age in which they might be suffering from an unfulfilled marriage like me.

First off, there are plenty of profiles on there. Many—understandably—don’t have photos because the women want to remain anonymous. The ones with photos often obscure their faces (I obscured mine too). Again understandable. Thankfully there’s a private showcase option where you can control who can see your private photos.

But here’s the thing. Like almost all other dating sites on the Internet, the ratio of women to men is just as low. In other words, just like, OKCupid, etc. Ashley Madison has many more men than women, which means women get many more winks and messages than they know what to do with. For a site supposedly catering to women, they’ve done a seemingly poor job of getting more women for horny cheating bastards like me.

And all that translates to having to work hard in contacting women, crafting a nice personalized message and subject line, so that hopefully she’ll open it up and read it and give you a chance.

Of the many dozens of messages I sent out—I don’t do winks—I received very few responses. Of the ones who did respond, I rarely got into a good message exchange with them. And needless to say, I did not go on one date.

I met my wife the old fashioned way—at work. So I’ve never done the online dating thing. But I’m such a techie that online dating makes a lot of sense to me. I read articles about crafting the perfect profile and taking the perfect profile pictures. I read e-books on online dating and how to write messages that will get responses. But it’s really hard work that doesn’t seem to really pay off. The numbers are stacked up against us guys. I don’t know what the male to female ratio is on Ashely Madison, but if it’s like the other online dating sites out there, it’s likely 2:1.

There’s also a surprising number of single ladies on this site. I don’t understand why a single girl would want a married man, but I encountered a handful of genuine ones on the site. Most single ladies on Ashley Madison are either looking for a sugar daddy or they’re professional escorts. Unfortunately there’s a lot of this noise on the site.

In addition to favoriting and messaging, other features of Ashley Madison include a built-in instant messenger and something called a Fantasy Date. Fantasy Date is IM on steroids, more immersive, allowing you to switch up the background and you can put a mask on your photo. To use up more of your credits, you can also send virtual gifts to ladies if you like.

The overall design of the site is fairly dated, exposing some severe technical limitations. For example, it will only save 20 messages in your inbox.

Two more gotchas. If you initiate an instant message chat with someone, you will be charged 30–50 credits (depending on duration of chat, 30 minutes or 60 minutes, respectively), regardless if the other member responds or not. That’s right, you could be chatting with a silent blinking cursor for those 50 credits. You better know damn well that the other woman will answer your chat or you’ve thrown away money. The other issue is that if you want to fully delete your account—burn your profile, images, and messages away from the inboxes of other members—you must give them $19.00. You can simply deactivate your account for free, but apparently the other stuff might stick around.

Bottom Line: I did not have much success with Ashley Madison, Your mileage may vary. ♠♠ 2/5 spades.


Note: Some links on this blog—including the links to Ashley Madison in this review—are affiliate links. This gives me a little kickback in case you decide to sign up. Thanks for your support!


With a dwindling Hobby budget, I was trying to think of alternatives. In my previous post, I said that I was not as dapper or seductive as Don Draper on Mad Men, so I can’t really seduce a co-worker. Or more truthfully, I want to be careful because I don’t want to do something to jeopardize my connection with my children. So I try to be more careful.

It’s not like I haven’t thought about it. Or that there hasn’t been opportunity. In fact, in my mind (key phrase), there have been a couple of possibilities. One was a petite blonde named Pam. We worked on a lot of the same projects together. Sometimes we had to hang out with drunk clients, only to get a little tipsy ourselves. She was married with a couple of kids and a good-looking husband. But she was always touchy-feely and flirty with me. I could tell she liked me. But I never really acted on it, because, well, superficially, she just wasn’t my type.

Another possibility, Lana, was tall and beautiful. Super outgoing, funny, and crazy. She was single and I felt a real connection with her. But she moved away before I could bond with her more. Seems like workplace romances/affairs take time to develop, and there just wasn’t the time. I was kidding her once though when she expressed her lust for one of our clients who was married. I joked “Just because there’s a goalie, doesn’t mean you can’t score.” She stated that while many of her friends were into dating married men, she wasn’t.

Anyhow, finding a like-minded married woman would be the best alternative to paying for companionship. I’m sure there are plenty of frustrated women out there right? Bored in their marriages just like me? What about the almighty Internet?

A Google search brought me to Their tagline is “Life is short. Have an affair.” Perfect, I thought. A site with like-minded married women. A goldmine. Or so I hoped.

To be continued…


In a recent episode of Mad Men, we see a young Don Draper living as a teen with his mom in a brothel. Surrounded by prostitutes Don (aka Dick) must have seen a lot of things young men are not supposed to see. At some point he is peeping through a keyhole, watching his mother have sex with a john. Meanwhile he’s also being brushed aside by another prostitute leading her john to her room. By way of juxtaposition, we the audience might infer that because Don grew up around promiscuity, it is simply part of his value system. And throughout the series, he inevitably cheats on whomever he’s with, whether it’s his ex-model (now) ex-wife, or his ex-secretary actress current wife. Don is a cheater.

But he is also mirroring what I’ve been feeling these past few years. More specifically, the show is exploring the themes that I’ve been facing in my own life: mid-life crisis, bored with your wife, feeling lost at work, looking for greater meaning and purpose in your life, looking for a connection.

Like Don Draper I’m a workaholic. I need to be in order to sustain my life with a wife and two kids, living in an expensive state. Like Don I have become bored with my wife. Also like Don, I am at the top of my career game, yet I have this fear that people will find out that I wing it sometimes. And I do wonder what’s next. What’s my next move that will help me make something better and bigger? And like Don, I’m a cheater.

But unlike Mr. Draper, I’m not that dapper and confident enough to seduce secretaries or interns at work (we don’t have secretaries). No. I need to be much more careful, which is why I opted for escorts. Though fantasies of seducing sexy co-workers have crossed my mind, I’ve never acted upon them.

As Don Draper continues his quest to find himself on Mad Men, I think I’m in that quest too.


Cheating on my wife means I take a lot of precautions. My windows of opportunities are often limited. Am I going out of town on business? Is she going to visit her mother and taking the kids? Can I fake another dentist appointment? Also, my hobbying budget was relatively small. It began big but side income became harder and harder to come by.

Therefore I don’t take unnecessary risks on providers who have not been reviewed well. But with all the research, all my dates can’t be spectacular. I’ve had my share of duds, as evidenced by last week’s fiasco.

One escort named Georgia looked pretty cute in the pictures on her website. She had an unusual rockabilly punk look to her which I found fascinating. But when I met her in person, I was a little disappointed. Additionally the BBBJ was just OK. However, she did redeem herself by riding me cowgirl for another 10 minutes after I had cum. Which made me have a second orgasm.

Another was an escort named KT. She was well-reviewed by my peers and had lots of them. When we finally met, she really wasn’t what I was expecting. She had tattooed eyebrows which always freak me out. She made me wait while she finished her shower. But she did have a whole closet of shoes which was interesting. :)   Sex was pretty good, but she didn’t offer the girlfriend experience I was looking for.

Or when newbie Holly advertised GFE but didn’t kiss with tongue. Or when gorgeous French Lana was very mechanical and rushed me out the door with more than 20 minutes left on our date.

All this to say that not every one of your experiences with escorts will be the fuck of your life. Your mileage may vary (YMMV) as they say.


After the Mother’s Day rejection, I decided I really needed a revenge fuck. I had an opportunity this week so I took it. I found this one very sexy well-reviewed escort who advertised on a number of ERBs and sites. She looks like a cross between a vampire and a biker chick (OK very similar). Tattoos. Cleopatra eyeliner. Black leather everything. Super sexy badass rocker girl. I was looking forward to having a blast with her.

So I texted her like she asks in her ad. She responded right away and we set up a date for the following night. She’s a funny texter actually. My 40 year-old self had to work really hard to decipher messages like “kk brb GTA hry” (“OK OK. Be right back. Gotta hurry.”). There was a lot of texting back and forth after I had confirmed the time and she was running late getting ready. I should have known then from her very spaztastic texts that the night wasn’t going to go well. But I was trying to give her the benefit of the doubt.

I finally got to her apartment and was made to wait a few minutes outside her door while she finished getting ready. When Donna finally opened the door, she was definitely the rocker chick, but I was a little disappointed. Slightly heavier than her pictures—not that big of a deal—but a lot more makeup than I am usually fond of. Her studio apartment was suitable and mostly clean, but she had a couple of small animals running around: a chihuahua and a skinny kitty. I’m actually allergic to animals so while I did mind, I was being respectful and tolerated them. Her windows were open because her apartment was quite hot, being on the top floor. But since her building overlooked two freeways, the place was actually fairly loud. She also had the fan going and some loud industrial music. And she was a mumbler which made it really difficult to understand what she was saying most of the time.

I brought some vodka (her choice) so we scrounged around her kitchen for some Styrofoam cups and ice. She proceeded to ask me about my taste in music. I said I liked almost everything but not too big into hip-hop. She put on some hip-hop and cranked it up. I don’t think she was doing that to annoy me, but more so that she didn’t really retain much of what I was saying. Throughout the whole evening Donna talked a lot about herself: her depression, eating habits, weight, big-ass-for-a-white-girl, credit rating, car accidents, ex-boyfriends, johns she refused, escort agencies trying to recruit her, porn companies trying to recruit her, etc. She was quite self-centered and didn’t really ask much about me. Any questions she’d ask would be about my opinions about her. Whatever I said she took the wrong way and once accused me of having bruised her ego three times. I did not go there and drop a few hundred to be made to feel bad.

She probably has ADHD and definitely fairly low self-esteem. In fact after the first BBBJ, she was trying to get me hard again, but right in the middle of stroking my cock, as it was getting harder, she got up and dug around her closet for a few minutes for some lube. Obviously whatever progress she made in getting me hard again was lost. Then when she returned with the lube and started stroking me again, she went on a long rant about escort agencies. Needless to say I shrunk again. Then she got up again to look for some perfume or cologne or something for a couple minutes. (I left my wedding ring on, which I always do with escorts so that they know not to leave marks. She should have known better about the scents.) Finally after about 15 minutes of hearing her go on and on about her life, I got her to fuck me, Asian CG. I didn’t last long, mainly because I didn’t want to. She kept riding me though until she came, which was fine.

After that, I put my clothes on and got out of Dodge. So much for my fellow Hobbyists steering me right. Again I do want to say that this is a rarity. Most of the escorts I’ve seen aren’t this crazy and don’t have issues like this.

More semi-horror stories in the next entry, but this one was probably the worst yet, and I’m left unsatisfied.


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