Corporate condom boy went bare for me

[raw773]

I finally got into a tight little hole that only wanted condoms. It was so worth it. Here's how I did it. Thanks to @Nclchub and @verslut for the tips in the other thread, How to actually use a condom.

So this younger guy works a big-company corporate job, is very clean cut, and likes to go by the rules. He has never heard of a cock cage, has never done poppers, and when I playfully teased him about spanking him with my belt, he freaked out and said "it's a hard NO!" He also refuses to talk about fisting (I want him to do it to me). So pretty vanilla. Still, he's crazy hot and he's into me too. I am willing to play by his rules... to an extent.

First time we fucked, I let him fuck me with a condom on. I think it was the first time I've used a condom in ten years. It was fairly nasty but still nice getting fucked. Afterward I was massaging his back, and out of nowhere he blurts out, "You can fuck me but you must use a condom! OK???" I was amused. I wasn't close to fucking him.

Over the next week we were sexting and talking about how it was my turn to return the favor and top his ass. I was busy with my own stuff and could not get around to his place for a while so it was a few days. We finally got together over the weekend.

You guys had given me good advice about putting lube in the condom and getting ready for it. I also decided not to JO at all so I'd have more cum brewing in my balls. It couldn't hurt.

We're messing around and finally get ready to fuck. I'm lying on my back and he's straddling me. Out comes the lube... he lubes me up and lubes up his own hole. Then, he just sat right down on me and started humping himself -- without the condom. About ten or fifteen seconds later...

Him: "What! Where's the condom?"
Me: "You just lubed me up and sat down, bro. You knew damn well there was no condom."
Him: "Well you should have warned me!"
Me: "I thought you knew what you were getting into. Sorry. Let's play by the rules."

Ha. So we stop. Out comes the condom. Now he's lying on his stomach. "Please just hurry and fuck me," he said. I complied, rolling it down onto my shaft. It sucks so much, guys. He has a hairy asshole and I love the scratchy feeling of that on my cock. But I did my duty and rubbered up and fucked him.

And it wasn't terrible. The extra lube helped. I plowed him pretty good, and he started calling out my name. "Oh, raw773 🙃, keep fuckin' me, keep fuckin' me..." I was getting into it, slow, deep, fast, jackhammer.

He started getting a little whiny though, and I know when bottoms get to squirming around something is wrong. I couldn't tell what it was. I pulled out and relubed. He said, "Can we maybe take a break?" I said "Sure, man." He reached back and ripped the condom off himself and threw it on the floor.

Then we kissed and cuddled. Now we're rolling around, being silly, and making out. He maneuvers himself so we're lying side by side with him in front.

Me: "Let's play a little game. It's called 'just the tip.'"
Him: "Uhh, I don't think so."
Me: "Come on. I'm just going to brush my cock back and forth. It won't go in."
Him: "OK."

So I did exactly that. Just smearing my cock around gently on his hole. He started humping a little but not in a way that would get it in.

Finally I'm lined up with his hole. I am totally still. And he backs up about two inches -- right onto my swollen, angry cock!

Me: "What are you doing?! This is supposed to be 'just the tip.' Don't you realize it's already in you?"
Him: "What? It is???"

But he made no effort to pull off. Just lay there and acted confused. Then he deliberately pushed back another inch.

And when he did that, guys, I slammed it all the rest of the way home.

From there on I turned this little condom queen into a bareback bttm. He kept rationalizing it: "Well, I guess if the seal has already been broken, there's no harm in going further." Or, "You know, I think the condom was really affecting both of our performances."

Ultimately he was begging for my load and I gave it to him: deep, deep fuckin' inside, where it wasn't coming out easily. I spent the night and we fucked maybe eight times on and off that night and into the next afternoon. When I left, he was calling himself "a little BB bad boy!" He had three loads in him when I left.

So the lesson of the story is: If a condom guy needs that to make himself feel comfortable and safe, think about giving him what he needs. It just might get your cum all the way in where it really belongs.

 

[alwaysready]

interesting. i see that your status is 'don't ask don't tell.'   i also see you are lookinig for victims.  i wonder if this will turn out to be one of them?  you think he fucks around with other guys? probably if he does now it is raw.  so hot.  no one really wants a condom on.   not real sex.  you should not shield the LifeForce from entering another, and doing its work--whatever that might be. 

[raw773]

32 minutes ago, alwaysready said:

you think he fucks around with other guys? probably if he does now it is raw.  so hot.  no one really wants a condom on.

Ha. He told me, "Well, now that the barrier's broken, I guess there's no reason to look back." But said if I hook up with anyone else, I better wear a condom.

I think I agreed. Can't remember.

[Greim]

So hot!