The Intentions of An Older Woman

Beyond Borders & Bedposts Issue #6

If this is your first time joining us, you’re going to want to start by reading the first issue which you can find HERE.

Later that evening, my buddy Aaron returned from his mouth dance with the “on-street ladies of opportunity”

Me: “How’d it go?”

Aaron: “Fantastic! Best five dollars I’ve ever spent! You need to consider going next time”

Welcome back!

So from the last issue, I was asked a couple of questions.

#1 Did I figure out what happened with the Hawaiian punch vomit on the walls?

#2 That night after clubbing, did I have a run-in with Miss Kentucky?

As much as I could piece it together, I had passed out on my bed fully clothed and full of Hawaiian punch.  Then sometime in the night, got too hot, stripped down naked, and then needed to vomit. I was probably sleepwalking and thought I made it to the bathroom but didn’t and vomited against the wall in several places and then grabbed the blanket and covered myself up in the corner of the room.

No, there was no interaction with “Miss Kentucky” that evening. She was not at the neighbor’s apartment all the time, only on special occasions. And if she had happened to be around that evening, I don't think I would have given the performance either of us would have hoped for.

Ok, now back to where we left off last week.

…I got up, walked over to the pregnant “Ghetto Fabulous”  girl’s apartment, and knocked on the door…

She opened the door and invited me in.  

As I entered, I saw my friend Jay sitting on the bed smiling.  

Me: What are you doing here?

Jay: Just hanging out, but I’m heading to McDonald's, getting a shake. Enjoy!

Me: I’m coming with you

Pregnant girl: You aren’t going to stay?

Me: I’d love, to but I gotta talk to Jay

Pregnant girl: Whatever

Jay and I departed and headed to McDonalds

Me: Anything I need to know about buddy? Are YOU fucking her?

Jay: Nah man, I just think she’s interesting

Me: Yeah, she is interesting, but this situation doesn’t feel right to me, I’m out.

Jay: I understand.

The thought process was. I would like to have sex, and this opportunity seemed doable. I would have the opportunity to see what it’s like to have sex with a pregnant gal. However, the situation seemed off. There was something in the air and it wasn’t magic, it was like a whisper of a warning.  So, my mind and body were pushing me toward it but my gut overruled and had me bow out.

My day-to-day life was going pretty well. I was managing to stay out of trouble.

Oh and to answer the question you are probably wondering, NO, I never did have sex with that pregnant chick or any pregnant chick ever. Sorry to disappoint you. 

So I still don’t know if it feels any different, but according to Google, it can feel different for the woman but no real noticeable difference for the guy. If I ever find out for sure, I’ll check back in and let you know.

Anyway, back at the apartment, some of the fellows and I decided we would check out the online dating market, perhaps this would be more effective in providing some ladies for us.

Chat rooms were popular at the time and we would all join a chat room together and try our luck. Each of us had our specialty techniques we would try out to get noticed. 

One guy, Dave would always ask girls for their email and then would email a picture of his dick to the girl. When I think about it now, he was ahead of his time, I don’t think many people were doing that back in those early days of the internet.  I’ll tell you this though, it did NOT seem to enhance his ability to get dates.

Jay had pretty good luck online, because he was open to a thicker (full-figured) type of woman, and there was no shortage of those, so he had plenty of options.  

My opening line entering a chat room was “Do any of you ladies like cheese? Let’s talk!” and although it sounds stupid, it would always get their attention and someone would talk with me.  

If a girl was really friendly and cool, I would ask “How much do you weigh?” 

Usually, at that point, they would call me an asshole and say I was superficial (which is correct), and then Jay would sweep in and let the ladies know that there is nothing wrong with being a big, beautiful woman and that he would like to learn more about them.

One day I met a woman online who was a bit older. I was in my mid-20s and she was in her mid-30s, attractive, successful, and she also happened to be married.  She wasn’t looking for anything “serious”.

So did I talk with her after learning all of this?  Of course I did.  This is part of growing up, there are lessons to be learned out there in this world and I was determined to learn some. 

I wanted to see what she wanted from me, what her angle was, and where this path would lead.

After a few days of standard conversation, we exchanged photos.  Keep in mind this was 1999 so these were actual physical photos sent through traditional mail, not digital photos.

That went well and we had all the usual standard discussions about hobbies and eventually graduated to erotic talk.

She caught me off guard when she told me she wanted to get me a gift. 

Whatever I wanted, she would get it for me.

Well, that’s the first time in my life anyone had ever said anything like that to me (and I don’t think anyone has said it since) but I figured I would test her and see how serious she was.

I asked for a bottle of Johnny Walker Blue Label scotch. Which at the time was about $185 per bottle.  That was a LOT of money in 1999.

Without any hesitation or further discussion whatsoever, there was a bottle of Johnny Walker Blue Label delivered to me the very next day. I was impressed!  

I was also terrified! 

It honestly scared the shit out of me because I thought “What am I going to have to do for this? What do I owe her?”

This was a good lesson because I think of this every time I see a guy buy a girl an expensive gift out of the blue.  Oftentimes, the girl will stop talking to the guy and the guy is confused as to why.  But I know why, it’s because he scared her.

Anyway, I didn’t know what to do. She wanted to meet up in person.

I told her NO. Sure you can judge me all you want and talk about what YOU would have done but it was too much for me. An older, successful, married woman, buying me expensive gifts.  It was too much for me to process.

My thoughts at the time were: This has never happened to me before. I have no reference for this experience and I don’t know how this would play out.  If I step forward into this situation, what are the consequences? Because there will surely be a price to be paid and on the surface, it seems like it would simply be sex, but it could be much more, especially when you’re dealing with someone who is married.  I don’t want to be that kind of guy.

Currently, I feel like I am open to accepting expensive gifts from anyone who wants to give them, and I can appreciate it these days more than when I was younger.  (In case you’re wondering)

I told the woman that I didn’t feel comfortable moving forward and she said she understood and that was the end of it.

I think about her from time to time and hope she is well.

A few days later, I was having a beer in my apartment trying to think of new and improved ways to meet women. I got a visit from a buddy who lived downstairs from me, we’ll call him Aaron. He had some interesting news to share.

Aaron was a pretty cool guy who was a tall, husky, gentleman of color, and he loved oldies music. Everytime he would swing by, he would always suggest we listen to some oldies.  Today's song was "Float on" By the Floaters.  That song came out in 1977, long before Aaron was born but you wouldn't know it from his excitement.  After the song started playing and he sang and danced along, he had some interesting news to share. 

Aaron: “Hey bro, there are crackheads downtown giving blowjobs for five dollars. 

Do you want to come with me? I know you’ve been looking for some action.”

Me: “Absolutely not”

Aaron “Why not?”

Me: “Five-dollar crackhead blowjobs? That’s a horrible idea!”

Aaron “Aww Man! You’re missing out!”

Me: “I’m happy to miss out on that nonsense, but come back and tell me about it when you’re done”

Aaron “You got it!”

Me: “Happy Hunting!”

I couldn’t help but wonder how that was going to turn out. And should I have gone? On the surface, it seems like a bad idea but maybe I’m wrong. It hadn’t occurred to me that engaging street people for sex would be an option. The risk/reward matrix seemed to not balance out correctly, plus it just seems gross. But what do I know?

Nothing to do but wait and see. And while I was waiting, I went a couple of apartments down to spend some time with the Boston girl. 

We would hang out from time to time, sitting on her front porch with a beer and talking about life.

During the discussion of the day, I told her about women’s bathrooms in their homes.

This is usually one thing that women overlook when they are expecting a visit from a man to their home. It never occurs to them that the man will lift the toilet seat to pee. Women never lift the seat, so most of the time, women are unaware that there tends to be collected “residue” under their toilet seat that the guy will be exposed to when he uses their bathroom.

Naturally, she was horrified because her bathroom just so happened to have that implied condition and I had used it moments earlier.

We all can learn from this, glad I could bring it to the forefront of awareness. 

Not all heroes wear capes.

My thoughts on Boston girl? She was decent looking, and really cool. I thought, there could possibly be a time and place where something might happen between us, but it wasn't going to be today because you shouldn't have sex with your neighbors. But I may need to re-evaluate that rule in the near future.

Later that evening, my buddy Aaron returned from his mouth dance with the “on-street ladies of opportunity”

Me: “How’d it go?”

Aaron: “Fantastic! Best five dollars I’ve ever spent! You need to consider going next time”

Me: “That’s never going to happen, I’ve got too much pride for that”

Aaron: “Yes, yes you do, and that’s what holds you back from greatness”

Me: “Is that what it is? Not getting blowjobs from addicts is what’s holding me back?”

Aaron: “Yes”

I bid Aaron a good evening and wished him well.

The next week he stopped by to inform me that he had needed to get medical treatment for an issue that had developed because of his little adventure. 

It reinforced my decision to not join in on that activity the next time I was invited.

Aaron however, was not discouraged, he took a month off and was right back at it again. 

I gotta admire his dedication.

(To be continued on the next issue…)

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