Last Loads

[TheHole]

Chicago, March 3-6, 2021, Heart ‘O Chicago Motel:  29 Loads.

 

Midway was busier than La Guardia but, unlike La Guardia, all the restaurants were closed, even the take-out places.  Going out across the city was like going into New York, so different than Texas or Georgia.  The L was empty; Roosevelt station was empty; the second L train was empty.  I got off the L at Thorndale, and crossed a dozen or so blocks of residential apartment buildings until I reached my destination - the infamous Heart ‘O Chicago Motel.

 

An older man, with long, scraggly fingers and dirty, thin blonde hair spilling over his shoulders, checked me in. His waist was probably as thick as one of my thighs.  He reminded me of the sleazy hotel keeper on HBO’s Deadwood.  The entire time he was checking me in I was thinking about sex with him, his thin arms wrapped around my chest, the skin dangling against my body, my plump nipples squeezed between his long, wrinkled fingers, his cock entering my Hole, his nasty breath filling the air I was breathing, his toxic seed pumping into my Hole.  I suddenly realized how truly hungry for cock, any cock, the Hole was right now.

 

The room had an actual, metal room key, and the door knob was one that could be left unlocked.  That would be convenient. Like most cheap motels the furnishings were basic, with a small table and a bed.  The walls were painted paneling.  The bathroom had yellow subway tile accentuating a toilet, bathtub and sink, all yellow.  It was kind of cute, in a mid-century Mod sort of way.

 

Up the street from the motel was a White Castle and Starbucks.  That would be convenient.  I posted my ads, prepared the Hole, and waited for cock.

 

The evening went like my first evening in Chicago.  Slow.  A dude listening to dance music on his Beats pumped me with four loads.  He would come, clean up in the bathroom, get dressed, then let me kiss his cock ‘one last time.’  The first three times he hardened again.  Next thing you know he was in the Hole, pumping in another load.  The fourth time he didn’t get hard, and he left drained of all his seed.

 

Then it quieted.  Hours passed with no cock.  A dude hit me up, but he wanted me to travel.  I wasn’t traveling. A cute latino from Grindr stopped by, pumped in a nice load.  Later an Asian stopped by, pumped in his nut.  

 

I woke up early on Friday, thinking the cock in Chicago was going to be as lame as the cock in New York. Three cock stopped by on their way to work - a BBC, an older gent, and another black guy.  Around 9am, the dude that wanted me to travel the night before hit me up.  He wanted to know how many loads I had in.  He was disappointed that it was only three, but he wanted in.

 

He gave me specific instructions. He wanted me completely naked - no jockstrap - on the bad, ass up, on all fours when he walked into the room.  I complied. The door opened. Light streamed in.  Then he was shoving the thickest cock of the trip in the Hole. And the Hole was his. His strokes were long and deep. He adjusted the Hole to his needs - spreading the legs, pulling them close, pushing the back down - getting just the right angle. He would instruct the Hole to push, push hard.  It pleased him. He was digging inside for cum. He found it.  He would instruct to push harder.  On the out stroke, he would spit on his shaft, push it in. “Give me that Hole.”  This continued for 45 minutes, and hour.  It hurt.  When he was ready to nut, he pushed my head down, lifted my back. The Hole was high in the air. He was drilling deep, and hard, crushing his cock deep inside. I screamed. He nutted.

 

Three more cock stopped by after him. After the last one, he asked me to travel to him again. This time I obliged, riding an uber with cum leaking down my thigh.  In his apartment I stripped, mounted his bed like I had been mounted earlier on the motel bed. He wasted no time in positioning me to his liking, pushing his thick cock deep inside, instructing me to push back, push the cum out.  He knew what the Hole was, a repository for cum, and he liked that.  For another hour he fucked, digging the anonymous loads out of my ass with his shaft.  He didn’t speak to me afterwards.  I gathered my clothes and left.  

 

Back to the Heart of Chicago. I figured it would be another slow night, like last night.  I bought a six-pack of beer. At the motel I opened the bathroom window to keep it cold.  Since it seemed so slow I added my room number to the Grindr and Sniffies ads.  Usually that doesn’t result in anyone stopping by, but I would see if it worked in Chicago.

 

I got a few teases as the evening progressed, but the only one coming over was the dude from Grindr last night, and that didn’t work out too well.  I hadn’t douched all day, trying to keep the cum inside. I hadn’t eaten either, so I didn’t know if I actually should douche.  Well, I should have. He didn’t appreciate that little accident.

 

Near 11pm a dude fucked me. He nutted, and went into the bathroom.  A knock came at the door. I assumed that it was open, but the guy must have locked it.  I unlocked it.  A dude came, stripped, and started fucking me.  The first dude came out of the bathroom, saw the guy, got a little perturbed, dressed and left.

 

That’s when it started.  The door was unlocked.  Another dude came in almost immediately after he was done.  Then another. And another.  It was cock after cock.  Cock was almost constantly in the Hole. I’d occasionally lift my head, glance around the darkened room.  Sometimes there would be shadow figures around the bed, watching, sometimes there wouldn’t.  Cocks would enter my mouth, leave my mouth.  There were big cocks, big loads, small cocks and small loads.  I tried counting, but lost track.  Some cock hurt, some didn’t.  Some guys slapped me around, others fucked gently.  One dude pissed in my mouth.  One dude sank his teeth into my back until I screamed.

 

It quieted down about 2am.  Then a few stragglers who had been parked in the parking lot waiting their turn, came in, one-by-one. First a large black man that had been put-off by the group action earlier. Then a tall, skinny black man with a long cock. And, last, a bear that had (apparently) been trying to slide into the Hole all night, but had to wait until I was alone.  I’m pretty sure I undercounted the loads, but there was at least 11 that night. 

 

But there was one more.  I knew who wanted the Hole now. It was 2:30am. I was tired. I was sore.  But it was my responsibility to provide him with that Hole, to provide to him the cum that the Hole had collected.  I summoned an Uber.

 

At his apartment I assumed the position on the bed. He fucked like he did before, his thick, long cock drilling in slow, deep, making me push back, pulling that cum out.  It was uncomfortable.  I had lost my poppers earlier.  My thighs hurt.  He move my legs open, then closed.  The shift in position helped a little. He went to piss.  I stretched my legs.  He came back. I offered the Hole.  He was in and out.  Thirty minutes passed.  I couldn’t take it any longer.  My hips hurt, ached. I did what the Hole shouldn’t do; I started whining. He said if it hurt I could leave.  I did.  I failed.  I should have been more prepared to give him what he wanted, what he needed.  I should have endured the pain.  But I didn’t.  

 

Twenty-nine loads in Chicago.  And I still failed.