The 50-Something Frat Boy

Not a frat boy fan.
Not a frat boy fan.

(** First, I’d like to thank my followers for your support and interest in my writing. I feel like I’m finally able to sit down and say a little bit. Still no answers about my friend’s death, but time is helping things move along.)

Now, I’m going to tell you about another oddball I dated earlier this year.

As I’ve said before, many people have suggested that I date older men. Besides the “arrangement” site, I did meet someone about six months ago that piqued my interest for a short time. Over a three-week period, we hung out multiple times and went on one actual date. He was about 10+ years older than me, in decent shape, easy to talk to, seemed to have his shit together.

But in the bedroom, he was clueless and selfish. He was okay making out, but in the end, I did most of the work, there wasn’t much foreplay, he satisfied himself and was done. I made the excuse that perhaps he was tired, but it happened three times. The very last time it happened, I literally got up, got dressed, and went home. He asked me if everything was okay. I said yep, I just need to feed my cats (because even they gave me more attention than he did!).

A few weeks later, I was out and about and had learned that he’d just gotten out of an engagement about three months prior. Well, I was not aware of this, because I was pretty sure he’d told me he hadn’t been in a relationship in two years. So again, I was the rebound girl. I was pretty pissed when I learned that, so I sent him a text asking him to confirm this information. He said it was true. I was like WTF… how does that equal two years? Next thing I know, he walks into the place where I’m sitting, strolls up and sits right next to me, carries on loudly like a frat boy, and says nothing to me. I paid my tab, walked out, and sent him a text telling him he’s an asshole.

I never heard back from him again, nor did I run into him (thankfully) until recently. He paid the bartender to buy me a drink on him as an apology for being an ass. A week or so later, I ran into him again and thanked him. We chatted for a few minutes, mostly about work. I only told him that I write sex blogs for content, never of course mentioning this site or what I actually do on cam.

Suddenly, he became interested in me all over again, bought me another drink (I guess he thinks that’s his ticket in), and he’s been texting and calling me wanting to hang out. I’ve barely replied. Today I noticed he left me a voicemail the other day asking why I hadn’t called him back after I was done blogging one evening, because he’s really interested in reading it. He sounded like a total perv dweeb. I never responded.

Will I ever respond? Doubtful. Will I ever tell him about this site? Never!

And then there are those Sugar Daddy sites…

No sugar daddy at the Comfort Inn. ;)
No sugar daddy at the Comfort Inn. 😉

I’ve always been attracted to younger men and generally don’t date anyone more than about 4 years older than me. My entire adult life I’ve been told I need to be with an older man, because of the maturity level. But let me tell you – I have not seen much of a difference in maturity when it comes to age.

I’ve tried a spectrum dating sites over time – ranging from the typical PoF and Match and Tinder to Cougar dating. I thought I’d try out a sugar daddy site to see if I get any different results from men that supposedly have money (as opposed to half of the ones I meet that are unemployed), to see if I get treated better. I have to say that anyone that I was physically attracted to was looking for much younger women/girls 18-21. There were very few attractive men on there to begin with, and many were married just looking for a fling.

The first “gentlemen” I agreed to meet for lunch claimed he was in his early 50s (looked older) and lived about two hours away.  This was right when my job started cutting my hours, so I had some time to meet during the week. (Let me add right here that when I first meet anyone, I dress in appropriate office attire, so no one gets the wrong idea.) Of course he looked better in his photos, but I was trying to figure out if we would click. We met at a sushi place, sat in the back corner so we could speak. The place was super quiet, which made it awkward to have a conversation without everyone hearing us. First, we talked about what we did for a living and basic life things. (Oh… and he’s married, but she’s not interested in sex and hasn’t been in a long time.) I watched him eat his sushi with a fork, tried to teach him how to use chopsticks… it was a disaster… which made me think he’s not very refined for a man his age, but it gave me something to talk about.

As we finished up, the place started clearing out, but the two women sitting behind us were barely whispering, which made me think they were listening to us. Then he got on his phone and started googling something… his entire face changed from normal to lustful creepy… said something like, “So how do you want to do this? Want to get a room at the Comfort Inn down the street and see if we click? I know you could use the money.” He’d been googling hotels in the area. (Let me add right here that the area is not a place I would ever get a cheap hotel, no matter the occasion.) He wanted to leave right away.

I was taken aback, because this wasn’t the “arrangement” I was seeking. In fact, I had clearly stated in my profile what I was looking for, yet I was open-minded at the same time – and I certainly wasn’t asking to get paid to have sex with a stranger. Speechless, he could tell that I was uncomfortable by his surprising offer (not to mention that a place like the Comfort Inn would be a place to sleep when I was in college, but certainly not a place to take a woman if you’re trying to woo her.) Plus, I had clearly stated I’m not an escort, so at the same time I was slightly offended but it hadn’t completely sunken in yet. It was like the initial shock you feel getting unexpectedly slapped in the face.

I politely told him I’d have to think about it, since we just met, and it was a good excuse to get the hell out of there. Once I left and had time to absorb what had just happened, I was disgusted. I mean, how does a man claiming he didn’t want a “pro” or an escort meet someone like me and offer the same exact thing he claims he’s not looking for?

I had about an hour drive home to think about it all, sent him an email saying thanks but no thanks, and I let him know that his offer was offensive and cheap. He apologized, because that wasn’t his intention. We didn’t contact each other again. About a year later, I went back on the site and he was still on there without any changes to his profile. Some men just never learn, no matter the age.

After meeting two other men on that site, I deleted my profile. To be continued…