Chicago Boy
@chibryboy.bsky.social
thots. prayers. sex | 🖤 a dirty DM 😈
📍Chicago
📍Chicago
Reposted by Chicago Boy
Reposted by Chicago Boy
December 15, 2025 at 6:35 AM
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What's for lunch
December 18, 2025 at 9:02 PM
What's for lunch
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"Make me cum Dad"
December 6, 2025 at 6:36 PM
"Make me cum Dad"
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December 17, 2025 at 2:24 AM
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December 17, 2025 at 2:26 AM
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📚 “Ephεbophiliα” ✏️
is the primary sexual interest of an adult in adolescεnts.
In men, this interest specifically focuses on yοung men who are post-pubescεnt, in the mid-to-late tεεnage stages of physical & emotional development—which is not linear—or early yουng adulthood.
is the primary sexual interest of an adult in adolescεnts.
In men, this interest specifically focuses on yοung men who are post-pubescεnt, in the mid-to-late tεεnage stages of physical & emotional development—which is not linear—or early yουng adulthood.
October 16, 2025 at 2:15 PM
📚 “Ephεbophiliα” ✏️
is the primary sexual interest of an adult in adolescεnts.
In men, this interest specifically focuses on yοung men who are post-pubescεnt, in the mid-to-late tεεnage stages of physical & emotional development—which is not linear—or early yουng adulthood.
is the primary sexual interest of an adult in adolescεnts.
In men, this interest specifically focuses on yοung men who are post-pubescεnt, in the mid-to-late tεεnage stages of physical & emotional development—which is not linear—or early yουng adulthood.
Reposted by Chicago Boy
All the best lubricants
you’ll ever need
Are in Daddy’s warm spit,
And his precum and seed 💦
you’ll ever need
Are in Daddy’s warm spit,
And his precum and seed 💦
December 18, 2025 at 10:17 AM
All the best lubricants
you’ll ever need
Are in Daddy’s warm spit,
And his precum and seed 💦
you’ll ever need
Are in Daddy’s warm spit,
And his precum and seed 💦
Reposted by Chicago Boy
Mr. Mendez, the school Counselor, is always so nice to me! 🥰 We’ve been having a lot of fun together ever since he started rubbing my shoulders in his office one day…
And I can always count on him to write me a note to get me out of Math class! 💯
And I can always count on him to write me a note to get me out of Math class! 💯
December 18, 2025 at 2:33 PM
Mr. Mendez, the school Counselor, is always so nice to me! 🥰 We’ve been having a lot of fun together ever since he started rubbing my shoulders in his office one day…
And I can always count on him to write me a note to get me out of Math class! 💯
And I can always count on him to write me a note to get me out of Math class! 💯
Reposted by Chicago Boy
Virgin boy-pussy: mint in box, never opened… until big brother ripped the plastic off and took it for a test drive balls-deep.
December 18, 2025 at 4:09 PM
Virgin boy-pussy: mint in box, never opened… until big brother ripped the plastic off and took it for a test drive balls-deep.
Reposted by Chicago Boy
I was just supposed to drop off a file at my boss’ apartment. I was gonna slip it under her door and be gone. 😅 But then her son heard me, invited me in, and let me tell you what— he was such a fucking tease! 🥵 Just absolutely taunting me with his lil round ass…
It didn’t take much to get the hint!
It didn’t take much to get the hint!
December 18, 2025 at 8:17 PM
I was just supposed to drop off a file at my boss’ apartment. I was gonna slip it under her door and be gone. 😅 But then her son heard me, invited me in, and let me tell you what— he was such a fucking tease! 🥵 Just absolutely taunting me with his lil round ass…
It didn’t take much to get the hint!
It didn’t take much to get the hint!
Reposted by Chicago Boy
I dunno what it is with me and Art teachers, but damn! 😳 Mr. Johnson has been fucking insatiable lately! 🔥 He, like, will not stop fucking me to tears— it’s pretty amazing, actually. But I swear, if Daddy finds out, he’s gonna be furious! 😰
He’ll be so fuckin’ jealous…
He’ll be so fuckin’ jealous…
December 18, 2025 at 8:27 PM
I dunno what it is with me and Art teachers, but damn! 😳 Mr. Johnson has been fucking insatiable lately! 🔥 He, like, will not stop fucking me to tears— it’s pretty amazing, actually. But I swear, if Daddy finds out, he’s gonna be furious! 😰
He’ll be so fuckin’ jealous…
He’ll be so fuckin’ jealous…
Reposted by Chicago Boy
“You will find that if you really try to be a father, your son will meet you halfway.”
November 27, 2025 at 7:15 PM
“You will find that if you really try to be a father, your son will meet you halfway.”
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December 19, 2025 at 1:41 AM
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May 24, 2025 at 4:43 AM
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The thing about glory holes is that I ALWAYS lose a whole day to over-eating…
December 18, 2025 at 1:33 PM
The thing about glory holes is that I ALWAYS lose a whole day to over-eating…
Reposted by Chicago Boy
Should I go to the gym or stay home and keep going with this?
December 18, 2025 at 1:38 PM
Should I go to the gym or stay home and keep going with this?
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Sometimes you just have to get rid of it.
November 12, 2025 at 3:42 PM
Sometimes you just have to get rid of it.
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November 23, 2025 at 5:14 AM
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the way I’ll be such a good boy so I can swallow and suck
December 18, 2025 at 10:41 AM
the way I’ll be such a good boy so I can swallow and suck
Reposted by Chicago Boy
Reposted by Chicago Boy
December 18, 2025 at 6:20 AM
Reposted by Chicago Boy
🇺🇸 Twink
🇪🇸 Joven
#gay #gayoutdoors #gaycruising #gayexhibition #gaybreeder #gaybareback #gaypig #gayfist #gaybottom #publicsex #exhib #exhibtionism #exposed #pissing #outdoornaked #gayporn #porn #publickexhibtionism #outdoorsex #outdoorcum #nakedoutdoor #fist #gaymilitary #ass #gaycum #cum #gaypiss
🇪🇸 Joven
#gay #gayoutdoors #gaycruising #gayexhibition #gaybreeder #gaybareback #gaypig #gayfist #gaybottom #publicsex #exhib #exhibtionism #exposed #pissing #outdoornaked #gayporn #porn #publickexhibtionism #outdoorsex #outdoorcum #nakedoutdoor #fist #gaymilitary #ass #gaycum #cum #gaypiss
December 18, 2025 at 6:25 AM
Reposted by Chicago Boy
Nothing feels better than pumping a big internal load deep into @don_dave_x.bsky.social amazing ass in the heat! 🥵💦🍑🔥
justfor.fans/berlinloads?...
justfor.fans/berlinloads?...
December 16, 2025 at 5:21 PM
Nothing feels better than pumping a big internal load deep into @don_dave_x.bsky.social amazing ass in the heat! 🥵💦🍑🔥
justfor.fans/berlinloads?...
justfor.fans/berlinloads?...