https://www.fapbox.com/tags/prison-inmate/ Thu 04 Jun 2026 13:48:14 +0200 https://www.fapbox.com/videos/33820389/cruel-captivity-prisoner-subjected-to-cigar-and-cbt-torment/
My captive male, hooded with a potato sack and restrained by his now useless cock, endures the intense sensation of an anal hook with rope to the chained hook above him and his balls tied tightly to the bedpost behind him, all the while being teased and tormented by Mistress Diana, smoking a fine cigar. Teasing him with the hot smoke and intense heat of her cigar, dancing dangerously close to his vulnerable areas, she creates a thrilling and intense scene of power play, fear play and control. Let the games begin. ]]> Tue 01 Apr 2025 01:18:40 +0200 https://www.fapbox.com/videos/33820389/cruel-captivity-prisoner-subjected-to-cigar-and-cbt-torment/ https://www.fapbox.com/videos/33757370/double-domme-6-carpetbeaters-2-prisoners-hd/
2 naked, guilty prisoners bend over the orange prison trestle for their sentences for, amongst other things, online cheekiness and calling Mistresses "snakes." The Mistresses show no mercy as set after set, they work through 5 different old-fashioned carpetbeaters... some made from woven cane, some plastic, and even one from wire. The prisoners protest, they plead, they squirm around but nothing can stop this ruthless punishment. They're left black and blue and bruised, their bottoms quivering and glowing like red hot embers from a fire. ]]> Tue 11 Mar 2025 20:23:00 +0200 https://www.fapbox.com/videos/33757370/double-domme-6-carpetbeaters-2-prisoners-hd/ https://www.fapbox.com/videos/33733603/caning-scene-from-black-site-2/
During his Black Site Prison detention, the prisoner Handtrampled had to undergo a cruel caning and beating in Shift 5. ]]> Thu 06 Mar 2025 18:56:29 +0200 https://www.fapbox.com/videos/33733603/caning-scene-from-black-site-2/ https://www.fapbox.com/videos/33791018/leaving-stepson-with-a-gift-he-ll-never-forget/
Part 3 of 4 in Victoria Voxxx's feature entitled "Falling For Stepmom" My stepmom came back to visit me again in prison, and we get to have a CONJUGAL visit today!  Unfortunately, however, they only are allowing her to come to see me right outside my cell.  She is sizzling in her white silk blouse with no bra, and I can see her nipples through her shirt.  She clings to the bars, trying to get as close to me as possible, and whispers her adoration and thankfulness for me.  My stepmom tells me she'll leave me with a gift I will NEVER forget, and takes out her tits so I can feel them, then gets on her knees to take out my cock and give me the blowjob of my LIFE through the prison bars.  She gets sloppy on my cock and sucks a big cumload out into her warm mouth, then drips it out of her mouth so I can see it.   ]]> Wed 05 Jun 2024 05:20:55 +0200 https://www.fapbox.com/videos/33791018/leaving-stepson-with-a-gift-he-ll-never-forget/ https://www.fapbox.com/videos/33767220/the-prison-guard-1-amy-said-goodbye-to-her-old-prison-inmates-and-went-to-a-new-prison/
]]> Sun 18 Feb 2024 01:29:36 +0200 https://www.fapbox.com/videos/33767220/the-prison-guard-1-amy-said-goodbye-to-her-old-prison-inmates-and-went-to-a-new-prison/