Chicago 4 & 5 - Bottoming for a Bottom / Triple Load Score

Just to move this tale along, I'm combining two parts.  I hope that's ok with you. I'm pretty sure you won't mind.

Pt 4

My conference had a few hours before kick off and I was, well, horny.  A guy who looked decent was a few hundred feet away, but looked ok.  A little under my target height, perhaps 5'6".  Dark hair and beard were a big plus and a handsome-ish face - though it would turn out to be a better picture than reality

The dick turned out to be decent once we got past the formalities and me just grabbing his crotch. A little over 6", but fuck was it thick. I wanted it in more than my mouth.

As it would turn out he was a bottom. He thought I would be fucking him, or at least he'd be blowing me.  He was wrong.

To my testament, I had him rock hard with my mouth and my hand.  Within minutes, he was on the bed, pants still on but down to his thighs. Mine were off and I climbed on top of him, straddling his dick.

With spit from my hand to his dick for lube I eased myself back onto him and took him to the root.

He might have been a bottom, but his dick betrayed some aspects of topping. Yes, I did most of the work, but he wasn't complaining.  I just started riding that cock.

His idea wasn't to cum too soon.  Mine was to get the load faster than I'd normally want. I like the fuck. I like the process. With him, I just wanted to the load. Once I knew he was a bottom, I kind of lost interest in him as a partner. I wanted the TOP experience. Basically I was the pushy / aggressive bottom who acted like a top to get the dick and seed.

His idea was not to cum too soon, but again, his body betrayed him.  I could see it in his face. I could feel it in his cock. I could hear it in his breathing. He was there.  I took him over the finish line, adding yet another load to my ass.

He lay there as I put my pants and shoes back on.  He said he was in town for a conference, right here in this very hotel, he said.

Fuck.  I'd have to see hi again.


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Pt 5

During said conference,  my phone was kind of blowing up. The apps showed a new guy in town. I think we all know how that can be. The one no on has had (ok, you know differently, but they don't!) and the one they'll never have to see again.

Sure there were lots of flakes, as I sat their answering things in text while someone at the podium droned on about something or other. The subject of the conference wasn't nearly as drawing as sex.

One guy had me going back and forth. His pics were vague. His stats were good: blond, 5'10, 175, 7". He was a few miles away but wanted to come by. I told him what time I would be free, but he needed to be by sooner.   During a break, I stole away from the conference and back to my room.

Again, the door was slightly open. I was on my knees on the bed, shoulders down, ass up, lubed up. He wanted me in a jock. I didn't have one to be in.  The door creaked. I heard "wow!".

I heard the pants drop.

Unlike the early morning guy who was hard to start with, I had to drop to my knees and get the guy all the way up. Once I did, he went in. Oddly, I was still tight to start with - but he still went all the way in.  He loved it. So did I.

And the man could fuck. And he did. Me. In ever position.

The first load - oh yes, there were more than one - was just the way you saw it above. From behind and deep. Me on my knees.  He growled loud enough for anyone in the hall to hear, should they be passing by.

There was no rest for me.  When he pulled out, I went back down to my knees and took him in my mouth to clean him off, which I did. But he never lost his hardness.  After a minute or two he simply said, "up!".  I stood up.

He had me on my back on the bed. Face up. Legs up.  His dick up.......my ass.  I took another pounding.  I didn't get the second load then.  We did it on my side. We stood and I had hands pressed against the window for anyone to see, should they be on the 5th floor of the adjoining parking garage. It was there he dump his scum into me for the second time.

My hole was starting to really feel it by this point. I was open. I was lubed internally.  And he was still hard.  But I went back down on him, because I do like ass-to-mouth, and want the guy to feel me clean him off so he can pack away knowing I got it all.

This was not that time. Not yet.

He walked over to the sofa, something I almost never use ever in any hotel. He sat down and patted his leg.  The inference was clear:  sit on his lap.

This time I rode him. First cowboy style, and then facing him.  That went on for a good 10 minutes.  My legs were cramped but I kept going.  So did he. Pushing up when I slid down, I'd say we were a well oiled machine, but it wasn't "oil", per se.

I know it couldn't have been huge, but he announce his third impending orgasm.  This one I didn't feel, but I'm not sure who could have. Besides his two other loads, I had the conference guy's still in me too. 

I'm not one of these guys where cum leaks out of his ass and runs down the legs.  I keep that seed in me.

There was one more ass-to-mouth and I was done. Well he was done. He said he had another load in him, but he had to go.  I would have taken a fourth, just because I never have from one guy.  But it wasn't to be.

By this time, I missed most of the afternoon conference.  I didn't even bother going back.




Load Count

Oral:   01
Anal:  07
Total:  08