Gay Date Horror Stories Vol 1: The Guy Who Wouldn't Take Off His Hat


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So one day i finally asked "What the fuck is going on with you and this hat bruh?"  Now I'm a man that loves himself a hat, espcially a fitted.  I've amased quite a collection.  Like how some guys like watches or sneakers, I like hats.  So I understand rocking a cap, its an accessory.  But accessories are meant to be worn and taken off. 

So me and ole boy met through a mutual friend at a Pride event a couple of years ago.  He was down from Philly with his bois, bout 6"3, kinda thick, of course he had a beard down to his kneecaps because, Philly.  Anyway, we rap for a lil bit exchange numbers and promise to hang out while he's in town.  He and his boys walk away and

my friend goes "so what did you think?"

Me: Well he's def my type but I need to see him without his hat on.

My friend: Hmm I don't think I've ever seen him without a hat on.

Now history has shown us that anyone can look good in a hat.  Example:  Look at Neyo here:

Yes, the Champagne Life

Now look at this pic of Neyo without a hat:

This is more like that Sutter Home life

Guys that wear hats with thick beards that never take them off are usually bald or going. Which is cool because I love rubbing a bald head. Not to mention a lot of guys look sexy with a bald head. 

That wasn't the case here.

So we start hanging out, He used to travel from Philly to where I lived at the time for his job..and I was always in Philly at tht time to see visting my grandmother who was dying.  Whenever either of us was in the other's city we would go to the movies, dinner,  no sex we just chilling. So I'm seeing this guy quite a bit and I'm  noticing, he has not taken his hat off once since we've been seeing each other. 

He had added me on Facebook by this time so I went perusing through his pics and there was a definate trend.  HATS.  AT ALL TIMES.  Driving in his car: Hat. Hanging out with friends.  Hat.  Work: Hat.  I'm talking he even had a hat on in his baby pictures ya'll.

At this point the hat thing is starting to bother me a lil bit. 

So we've been traveling back and forth to see each other for a couple of months and I'm like ok the only way I'mma see him without a hat is if we fuck and I spend the night or something, he's gonna have to take his hat off then right?  Wrong.

I'm at his crib, we've been drinking and smoking and i'm like ok perfect opportunity he's relaxed.  I'm rubbing on his meat through his shrots, we're kissing and shit and I get ready to pull his dick out to give him some head

Him: I need to take a shower first

Me Ok you wanna take one together

Him Nah I like to shower alone.


But forreal I was like "oh ok, i guess"

So he gets in the shower and leaves the door open so I'm thinking ok Imma get a pieak of what this guys head looks like.


I was laid out on his bathroom floor like this when I saw him with that hat still on.  He was literally in the shower with a hat on.  It wasn't water proof and it was soaked.

He didn't notice me but he did turn off the shower so I bolted out of the bathroom back to his room and tried to look sexy laying across the bed.  I'm butterball ass naked.  He comes in the room dick first and he had taken off the hat he had on in the shower but :


I'm thinking his this fool a magician or something.  Normally they pull rabbits out of hats but he pulled a hat out of a hat.  This would have been the perfect moment to ask him about the hat however, at the time I hadn't had sex in 9 months and he was standing in front of me dick on brick, and my asshole was purring like a kitten going "you need to get fucked more than you need to know whats under his hat." forward and

...I'm riding him like his dick owes me money and HE STILL HAS ON THE HAT.  So I'm thinking to myself "I gotta find away to get this hat off of him"  So i lean over and wrap my hands around the back of his neck and slowly try and inch the hat off of his head.  Well that was taking to long so I just grabbed it and pulled it off. 


So if you're just joining us this guy took a shower with his hat on, pulled a hat out of a hat and then had on a wave cap under that hat.

And then he put his hat back on.  I said "You're going to keep your hat on even while we're fucking?" Him: Yup.

So we kept fucking because he had that bomb D.  But I was still curious and I was so close, and if he had on a wave cap under this wave cap I was leaving on the first thing smoking.

We finished up and laying down, he's like "now we can  get some rest" and he turns off his lights, but he still has this hat on.

Me: Bruh, you are not sleeping with that fuc....

Before I could finish his dick was back in me and I lost my train of thought, but when we finished again I was back on the hat.  I'll fuck you with a hat on but I'm not sleepin with you with this hat on

Me: Ok that was nice but about this hat?

Do y'all know he tried ot poke me again.  Now I loves dick and dick loves me but you are not gonna dick me down to shut me up

Me: We're not fuckin again until you take off that hat.

Well of course he took the hat off then. 

Before I could actually look at his head I could smell it.  It was a mixture of DAX Super Supreme Extra Sckrenf Wave Pomade, Blue Magic, Pink Moisterizer, a bacterial infection, and sweat.  I look over at his head and he's got patches of hair, bumps and open sores on his head and without the hat he looked 10 years older.


He saw my face and immediately went into this story about how he had started going bald and the then sores poped up and he was afraid to go to the doctor because he was afraid it was something serious


and yes I was rocking a fro at the time


Me: Yes that looks pretty seriuos and you should get it checked out first thing tomorrow. 

I grabbed my shit and bounced.

Needless to say I never messed with anyone after that who wouldnt take their hat off.


A few months after he that incident he sent me some pictures of him with his hat off and his scalp cleared up...

We fucked again lol

Special Thanks to Kevin M. for the story!



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