Trans

You know, I've never been with a trans person.  I don't know any, and there are none in my life.

But, the other night, a random thought just came into my head.  I don' even know where this random thought came from.  It was just out of the blue.

When I first started all of this "monkey business" of getting head from strangers via Craigslist, I used to visit this one guy.  I called him "Norm" as he reminded me a little of a younger Norm from Cheers.

Well, all of a sudden I was recalling the encounter, and boom it hit me.  I think Norm was trans.

10 years later, I have an epiphany.


http://onehookupatatime.blogspot.com/2011/05/craigslist-experience-1.html

I re-read my notes.  The hookups actually occured in June or July of 2009.  I hope Norm is doing well.

I also wonder why the hell I would think of that now.

Some BJ Action

So, this has never happened to me before, but yesterday, at work I was out shopping for a 1980s style boom box.  You know the kind John Cusack held above his head in the movie "Say Anything."

Something like that is difficult to find.  It's not so old you can find it in the antique stores, but not so new that it's plentiful in the thrift shops.   I checked a couple of mid-century modern shops with no luck, and then remembered this funky junk store in town.  It's a store that is a mix of Antique Store, Thrift Store and Yard Sale all in one.

The small parking lot in back was empty, so I parked and went in the back entrance.  I looked around in the back room, and found an area of electronics.  I saw film projectors, turn tables, old stereos, but alas, no boom  box.   Just for fun, I continued looking around. 

I went the to front of the store, and strangely, there was no one at the counter.  Not a soul around.  Weird.  I ventured to the other side of the building and went from one room to another, all filled with stuff for sale, and then walked through yet another door, and was startled to find a guy in a red t-shirt and glasses sucking off a thin blond guy who was looking at his phone!

It took me a second to process what I was seeing, and as they noticed me entering the room, the cock sucker immediately pulled off from the guys dick, which was left hanging down, covered in wetness, and as he tried to stand, and stumbled back.  The guy getting his dick sucked was just leaning against the wall looking at his phone, and seemed unfazed.

"Oh, I'm sorry!" I said, as I backed out of the room still a little confused by what I was seeing, but wanting to give them back their privacy.

Immediately I burst out laughing.  I didn't try to control my laugh either.  I wanted them to know I found the situation amusing, not horrific.

"Oh my God, I'm so embarrassed, I'm sorry. I so embarrassed!, said the cock sucker.  "Did you come in the front door?  We didn't hear you."  He tried to assemble himself, and apologize.

"No, I came in the back door.  Don't worry about it.  Looks like  you were having fun."

I awkwardly asked about boom boxes, and he showed me to the electronic area that I had already scoured.  He kept apologizing, and I kept laughing and telling him it was okay.  I said thanks and scurried back out.

I hope they got to finish what they started.

Jack bottoms.....

When I first met Amigo, and we were getting to know each other, over our first coffee date, we were quite honest and straightforward with each other.  Amigo let me know he was a "bottom".  He had little interest in dating another bottom. 

I, of course was/am a total top.  I tried to bottom a couple times, with the same partner, and once was a total failure, and once, I believe penetration happened, but it was short-lived, painful, and embarrassingly, a little bloody.

I'm afraid, I just wasn't built to bottom.

Not that I don't want to.  I see all those guys in porn, moaning with pleasure.  I read the stories about "unbelievable waves of pleasure."

I've expressed this desire to Amigo.  He's not particularly huge, smaller than me in fact, and we've alway joked around that one day, we were going to try.  I was going to try to bottom, and he would try to top me.  He even toys with my hairy ass sometimes, but I alway swat his hand away.  It feels a little foreign to have some  strange fingers roaming around down there.

He was alway asking, but it never really seemed like the right time.  Week after week he would say it was his turn, and then I would wave him off.

But, lately, I've been thinking about it.  Why not just try it?

Last week if he once again asked if he could fuck me and  I said yes.  I wanted to try. 

He looked like a deer in the headlights.  "Really?"

"Sure, let's do it.  Just be gentle."

Pause.   "No."

Turns out, he was bluffing all along!  He doesn't even want to try.  And, when I pressed him for a reason, he said he didn't want to turn me into a bottom!  He's afraid I will love it, an that will change our dynamic in the bedroom.  Haha!

I guess it could happen.  I'm a bit fan of  Reddit's Gay Stories Gone Wild.  Many times I've read how anal virgins were exposed to this previously unknown pleasure, and now they are itching for dick.

Perhaps Amigo is right.  Perhaps I don't need to travel down that path.  After all, we have a good thing going and we both pleasure each other.  I guess there is nothing wrong with that.

So, no.....Explorer Jack did not bottom.  Is not a bottom, will probably never bottom.

Butt, that's okay.

Just some photo I found online, to entice you to read my entry.  :)