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All characters and all works are fictional. No real life situations or events.
Total Albums: 6 +
Spanking Oliver 6
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Max comes over to say he is sorry for calling Oliver names. He agrees to get spanked, but the punishment won’t stop there…

spanks, restrained, pillory, locked in stocks, humiliating, kissing feet, gag, collar, paddling, chastity tube, footrub, blowjob, walking on four like dogs, crossdressing, handjob, facial, latex mask, cheerleading, childish outfit, peeing in shorts, shoving wet underwear in mouth, public nudity, femdom, submissive teenager, rope, baby powder, buttplug, diapering, playpen, sucking thumb, threesome, cuffs, piledriver sex position

$0.4 USD Pics/Vids: 34
Spanking Oliver 5
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Troy and Oliver go to Hanky Spanky and try different costumes. The endorphins from sex make them confident and relaxed. They have a lot of fun together, however Troy is still in the closet and Jenny doesn’t stop bossing around…

bounded, pillory, crossdresser, swollen bum, hardcore assfucking, exhibitionist boyfriend, humiliation, fucked by dildo, cockcage, bdsm outfit, jail, sixty nine, femdom, handjob, paddling, allergy to vinyl, rash, tight shorts, school nurse, stockings, incest, stepdad copulates with stepson, kissing in front of the whole class

$0.4 USD Pics/Vids: 24
Spanking Oliver 4
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Oliver is going to the beach with Jenny. He is picked on by older schoolmates for what he’s wearing, but he finds a friend in the end…

butt plug, pink girlish speedo, beach volleyball, paddling, bdsm tools, crossdresser, gay boyfriends, mom jerking off son, humiliation, kissing on the lips, changing undies, red butt, pissoirs, tied, rope, blowjob, chastity cage, lingerie, socks in mouth, incest, fucked by stepdad, caught, pillory, writing lewd words on body

$0.4 USD Pics/Vids: 36
Spanking Oliver 3
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Mom catches her femboy in her lingerie! What does he deserve? A tennis racket or a leather strap? Maybe a ping-pong paddle…

caught masturbating, boner, punishment, crossdresser, embarrassment, bunny costume, bdsm, measuring penis size, bounded, ropes, huge cumshot, red butt, fingering bumhole, paddling, spanked publicly, femdom

$0.4 USD Pics/Vids: 36
Spanking Oliver 2
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Oliver will work to earn the money for fixing Mark’s car. He also believes he deserves at least 100 bare-ass spanks with a paddle…

blue jeans, belting, red marks on bum, boner, stepdad, masturbating on porn, jerking off with a banana, pillow humping, spanked, blowjob, facefucking, sixty nine, crossdressing, sissy boy, caught while ejaculating

$0.4 USD Pics/Vids: 25
Spanking Oliver 1
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Oliver was normally a happy kid, but his parents’ recent divorce left him lonely and confused. He already knew he was gay, but still hadn’t told anyone. He began exploring porno sites and jerking off most evenings…

watching porn, masturbation, latchkey kid, 11yo, bending over, spanked hard, grabbing ear, white undies, intentional misbehaving, red butt, humiliation, embarrassing boner, cumshot, baseball bat

$0.4 USD Pics/Vids: 25