Search Results for Jason Windsor in Videos

Videos where Jason Windsor is featured in the scene.  —  Total Matches: 18.

Jason Windsor ChaosMen
Wow! Jason was fantastic! He was really into doing the photos and solo, and had great energy during his solo. He has a hot body and despite his big cock, he is a versatile bottom. His ass is perfect too, and like a good bottom, he was eager to show us his hole. He tends to like fit daddy types that are bossy in bed. So, for all you bossy tops, this guy is for you! Jas....View Video
Jason and Mitch ChaosMen
Jason's solo was amazing! And now I am equally impressed with Jason Windsor's cock-sucking skills! As usual, any time Mitch is in the room, there was instant chemistry. They start by jerking-off across from each other, when Jason got on his knees and started sucking on Mitch's cock. Jason has got skills! He could easily deep-throat Mitch. Take notice of his ass too, h....View Video
Jason and Kevin ChaosMen
I was very eager to get Jason Windsor back in after his very hot oral video. The guy just oozes dirty boy sex! I paired him with Kevin Texas. It was kind of cool to see them together with their opposing sleeved tattoos on their arms. Jason loves to bottom, and says he likes to be dominated. Kevin had just the perfect vibe for him. Jason started by sucking on Kevin, an....View Video
Jason and Kyle ChaosMen
Jason Windsor is such an amazing bottom! So, I have him lined up with all my best tops! I was super eager to pair him with Kyle Wyncrest. Kyle is always on his 'A' game, and really knows how to fuck. I also like the way Jason just jumps in with instant passion, which is also something Kyle always does. Lot's of kissing and cock-sucking in this video. Once again, the T....View Video
Jake and Jason ChaosMen
I feel so lucky to have more than a handful or really fantastic models right now. It has been so easy pairing both Jake and Jason. They bring so much energy and genuine passion to their shoots that it was a no brainer pairing these two guys together. And like any shoot with lots of sexual tension, they started flirting and making out even as we were getting ready to g....View Video
Jason and Trent ChaosMen
Jason stayed an extra day to give Trent Marx a blow-job. We thought that Trent might not suck dick initially, but of course once I interviewed him, I knew he wanted to suck a cock to get-off. Trent is an eager cocksucker, so he started by sucking on Jason's big dick. That got Trent hard, and Jason returned the favor. They sucked each other 69, and then Jason stood so ....View Video
Jason and Max ChaosMen
I was eager to get Max back in the studio. I knew I had to find a Bottom that could handle his big dick. And Jason is such a powerful performer and was eager to play with Max and scale Mount Everest that is his cock. They start by making out and then Jason slides down and sucks Max until he is bone hard. His dick of course, grow exponentially! Max returns the favor an....View Video
Gino and Jason ChaosMen
Jason tops! Gino bottoms! Jason has gotten a lot more confident topping, surprisingly because he has a new girlfriend. Gino agreed to bottom for a portion of this video, though you can tell it has been a long time since he has been fucked. Jason had to keep is slow and steady on Gino's poor ass. Jason is a great bottom, but that dick of his is huge, and Gino had a big....View Video
Merrill and Jason Active Duty
Merrill Patterson is a new recruit and Jason Windsor is right there to welcome the stud to squadron. He's real excited to be on the AD roster, loves to fuck hard, and he's ready to give Jason's ass a try. Featuring Jason Windsor, Merrill Patterson. Original release date: July 25th, 2021.View Video
Damien Tops Jason Active Duty
Description not available. Featuring Damien White, Jason Windsor. Original release date: October 10th, 2021.View Video
Drake and Jason ChaosMen
It actually didn't take me too long to get Drake back in the studio, but he had been busy shooting scenes elsewhere. For once, I really was glad. He got a lot more experience and was a great deal more comfortable shooting this video. Which was great because, as usual, Jason was on top of his game! Jason loved sucking on Drake's cock, and I think Drake was impressed wi....View Video
Get It On Active Duty
Jason Windsor and Tyler James, my my. These two studs can't keep their hands off each other. In fact, they were even fucking while the cameras were off! But, can you blame 'em? Featuring Jason Windsor, Tyler James. Original release date: January 9th, 2022.View Video
Aaron Plows Jason Active Duty
Aaron Andrews is still a little nervous coming in to shoot. But with Jason Windsor around, he relaxes super quickly. Watch as these two studs have some mind-blowing sex. Featuring Jason Windsor, Aaron Andrews. Original release date: February 20th, 2022.View Video
Twink Training Active Duty
We hope you enjoy this Training of the Twinks compilation we made for you! Featuring Jason Windsor, Tyler James, Johnny Riley, Johnny Thompson, Axl, Nick Gunner, Dominic, Princeton Price, Michael Stax, Jacob Stax, Brian Austin, Colt, Kaden Saylor, Trent, Damien White, Scott Finn, Ryan Jordan. Original release date: June 29th, 2022.View Video
Friendly Fire 15 Scene 2 AEBN
Active Duty is proud to present Friendly Fire 15 - where highly trained men reserve their loads for only their most trusted fellow soldiers. Produced by: Active Duty. Featuring Jason Windsor, Merrill Patterson. From the film: Friendly Fire 15.View Video
Reenlisted 15 Gay Hot Movies
Damien White dominates Jason Windsor in a hot scene where everyone finds their pleasure until there is an explosion of cum. Nick Clay pounds out Justin Lewis with his cock like Lewis has never experienced before. Brandon Anderson and Chris Damned, these two men are sexy as all hell. And? Brandon hasn't cum in a week! It's the perfect opportunity for Chris to show his ....View Video
Friendly Fire 15 Gay Hot Movies
Nick Clay can go all day in Friendly Fire 15. Lucky, lucky Johnny B. The soldiers screw on the squeaky cot and cum like good cadets. Merrill Patterson is a new recruit and Jason Windsor is right there to welcome the stud to squadron. He's real excited to be on the Active Duty roster, loves to fuck hard, and he's ready to give Jason's ass a try. Brandon Anderson and Hu....View Video
Friendly Fire 16 Gay Hot Movies
Jason Windsor and Tyler James, my my. These two studs can't keep their hands off each other. In fact, they were even fucking while the cameras were off. But, can you blame 'em? Blain OConnor is certified horny. Chris Damned? Also certified horny. The two together? A spectacular combination of charm, muscle and most importantly, sex. Hugo Santana is a fiery, passionate....View Video