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sirjess.bsky.social
Sides Welcome
@sirjess.bsky.social
For those drawn to surrender: a space to explore devotion, connection, and the art of relinquishing control. For the few ready to embrace true freedom. Novice Adult Filmmaker/Sir/Traveler/Passionate Love Making.
Pinned
Skanksgiving: Two tops warming each other up before the main event. By the time our bottom arrived, we were already charged and ready to make it an afternoon he wouldn’t forget. #gay #cock #softdom @niceguy7654.bsky.social
Day 2: Cumming on the socks a boy that keeps stirring me gifted me #socks #boy #foot #gay
October 31, 2025 at 1:27 PM
Post JO before gym. Soft cock, first load of many to come: Came on a pair of socks one of my boys presented me. #softcock #cum #load #socks #boy
October 30, 2025 at 11:15 AM
Reposted by Sides Welcome
You don’t kneel until I say so. But you can look. #legs #muscle #men #gay #chicago
October 15, 2025 at 2:36 PM
Reposted by Sides Welcome
Leg Day has been paying off #legs #thigh
October 22, 2025 at 2:14 PM
Leg Day has been paying off #legs #thigh
October 22, 2025 at 2:14 PM
You don’t kneel until I say so. But you can look. #legs #muscle #men #gay #chicago
October 15, 2025 at 2:36 PM
Friends, subs. I’m looking for guidance. Do you know of any poppers delivery options in Chicago? Share your knowledge with me 🤤 #chicago #gay #sexualhealth #poppers #delivery
August 27, 2025 at 5:21 PM
🤤
August 27, 2025 at 4:43 PM
New Favorite Position with my boy #boy #anal #dom #sub #gay #bb
August 5, 2025 at 2:15 AM
Ubering one of my boys for an hour of play then Ubering them back home is called efficiency. #gay #smut #sex #sub #boy #sir
August 3, 2025 at 4:47 PM
Third sublevel of the parking garage. Concrete floor. Bed dragged in. Two chairs angled for watching or waiting. Chicago pulsed above us, but he was busy being mine. Called out of his shift. Didn’t need the uniform tonight. #chicago #gay #bluecollar #sex
August 2, 2025 at 2:09 AM
Morning Session With My Barber:

Woke up with my lower back wrecked—either from the 5 rounds or how hard my boy was squirming. Barber asks, “You alright?” I say, “Yeah, just threw it out last night.” He goes, “Lifting something?” I go, “Yeah… my boy. Five loads deep.” Now he’s the one squirming.
July 5, 2025 at 3:11 PM
Making my boy spasm is like having a fireworks show on the Fourth of July 🇺🇸 #sir #boy #anal #gay
July 5, 2025 at 2:43 AM
Afternoon. You behaving, or just walking around hard and bored again boy? #dom #gay #sub
June 4, 2025 at 6:17 PM
Need a boy to piss on 🤤
March 26, 2025 at 8:14 PM
The things that went on last night….ran out of boy butter. Wish my boys would have let me film. #cumdump #sex #foursome #hotel #chicago #gay
February 7, 2025 at 7:05 PM
Reposted by Sides Welcome
Untitled (Nude with Oranges), 2017 Gabor Gozon (French)
January 4, 2025 at 8:18 PM
Good boy: following his commands. Relish the freedom while it lasts—soon, you’ll be fully sealed, a perfect symbol of your surrender and devotion @lthrbttm4u.bsky.social #caged #piss #dom #sub #boy #gay #cock
January 3, 2025 at 5:03 PM
Working from bed today. Haven’t busted a load in four days. #precum #cock #gay #raw #breed #cum #chicago #wfh
December 26, 2024 at 9:37 PM
Surrounded by stacks of filthy inspiration, I’m deep in my research, waiting for my boy to show up and serve like he’s supposed to. No excuses. Just submission. #Research #Pornography #Dumb #Boy #GayBlueSky #Hotel #Chicago #pornography #hotel
December 22, 2024 at 5:55 PM
Post Bate Load: Not Bad for a night of breeding. Boy didn’t want to film-however made me shoot a massive load in the steam room last night. 13 loads later: I’m ready for another round of breeding. #cum #dom #breed #cock #sex #gaysex #load #raw
December 22, 2024 at 3:37 PM
In the steam's suffocating heat, your teeth clamped onto my nipple, sharp and unyielding. My hand stayed on my cock, slow and steady, even as the pain spread. When I came, it was explosive, my body convulsing, raw and spent.You held your bite, leaving marks I'll feel for days.
#dom #sub #gay #bate
December 22, 2024 at 3:06 PM
Nothing like good ole’ research to get sir cock hard #dom #cock #gay #blueskygay #art #raw #stroking #chicago
December 22, 2024 at 12:05 AM