Chicago—May, 2022

Sometime during our bathhouse play at CLAW, Cowboy Boots asked if I would like to be his roommate at IML.  I told him I had planned on going, but to just a couple of events of the leather weekend—and thought I’d stay in a cheaper hotel.  Well, he had a suite at the host hotel and the man he thought he’d be sharing it with had made other plans.  I told him I would think about it.

Once I was home, I realized I did want to spend a little more time at the event.  I sent CB a text saying I’d be happy to split the room with him.  He wrote back that he would like to treat me.  And that I should bring the sling. 

It was already packed and ready to go.

Cowboy Boots had gotten an extra day, so I drove into Chicago on Wednesday—the day before most folks arrived; a day that is for the organizers and vendors to set everything up.  I was curious to see if the hotel would be busy.  I arrived safely and with less city-driving hassle than usual.  The Congress had had a much needed renovation since I had last been in it.  I got there before CB and went up to inspect the room.  It was indeed a two room suite with two walk in closets.  The view towards Lake Michigan was lovely.

CB arrived.  He was concerned there was only one queen-sized bed when he had told me there were two doubles.  We ended up having a rollaway out in the living area as well.  That way if I needed to go to bed, Cowboy Boots could continue taking random loads out there before he joined me in the big bed.  It worked perfectly.  The sling was also set up in the living room and available. 

I have eaten dinner and it’s time for sex.  I decide to start easy.  There are not a lot of men on BBRT and not enough men in the hotel yet to go cruising, looking for an open door.  I talk to someone who is helping one of the vendors do set up, but he doesn’t actually know his schedule for the evening.  Cowboy Boots is prepping to have a night of open door as a cumdump. 

In the flashing lists, I see a man who I know.  We have fucked, but we tend to talk more via a sex forum as he lives several states away.  He is here.  And he is even in our tower of rooms.  I go down a few flights.  His door is ajar.

Eroswired is sprawled on the bed, ass up.  I am in my flight suit, so I can just do one zipper and be naked enough to fuck.  I kneel behind him and dig my tongue into his full ass.  He can’t have been sure when I opened the door if it was me, but now he knows.  He groans.  Lots of men don’t bother to use their tongue on him.  They should.  He responds with moans and perhaps a “It’s all yours, Sir.”  I eat my fill.  My cock is oozing precum.  I want to give it to him.  I stand up and smear it onto his pucker.  I kneel again and eat some more.

Now I’m ready.  I stand up and slide into him.  He takes me, working his ass to make it a most pleasurable entry.  I hold to let him adjust---but he’s already ready.  The man was trained well.  Literally.

I begin to pump into him.  He groans again.  I let out an involuntary moan myself.  My cock is responding to his skills—his squeeze and release or the slight push back onto me.  He keeps it varied.  I never know what’s coming.

I fuck the hole of the man trained to service any man’s cock.  Hard.

That thought actually brings me very close to spewing my seed.  But for some reason my mind shuts down the impending orgasm.

We fuck for quite a bit longer, but it is suddenly much more just pleasant friction.

I pull out.  He cleans me.

We chat a little.  It’s his first IML.  I remind him that this is a bonus day—I have never been here this early.  The hordes arrive starting tomorrow.

*

I go back to the room.  As I open the door, it hits a soda can.  Ah, Cowboy Boots is expecting others and has his early warning device out.  I find him ass up on the bed.  Waiting.

I let him know it’s me by sinking to my knees and licking his ass crack.  He’s wet.  I can’t actually tell if it’s cum or lube.  I don’t care.  I just want to eat his ass.  I love the wetness and moan out my pleasure in doing him.

He tells me that he’s been fucked a lot—he’s not sure if anyone unloaded.  I don’t care—and tell him so.  He tastes so damn good.

I stand up and fuck him. 

My cock loves the juices of his ass.

I pump my cock into him over and over…

The original post is here:  From My Side of the Sling: IML Wednesday: Two Familiar Asses (felchingpisser.blogspot.com)  June 17, 2022