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jamieolive66

Sliding out the sound without hands

Sliding out the sound without hands

jamieolive66

350 ball slaps with metal ruler

350 ball slaps with metal ruler

jamieolive66

9min or so having an anal electrode in while having a vibe on

9min or so having an anal electrode in while having a vibe on

jamieolive66

Urethra Training 4 (Week 2): Adding droplets of water to spread

Urethra Training 4 (Week 2): Adding droplets of water to spread

jamieolive66

Relief after 3 hours of butt plug

Relief after 3 hours of butt plug

jamieolive66

Cumming with a mouthful of piss, then drinking all the piss and

Cumming with a mouthful of piss, then drinking all the piss and

jamieolive66

22 Feb (Day 2 of Training): 600x purple dildo fucks

22 Feb (Day 2 of Training): 600x purple dildo fucks

jamieolive66

Masturbating while drinking pee (+ bonus rope bondage) (Task

Masturbating while drinking pee (+ bonus rope bondage) (Task

jamieolive66

1200 ball slaps, 6 edges (part 2 of 2)

1200 ball slaps, 6 edges (part 2 of 2)

jamieolive66

Deep throat training with anal beads, plus the orgasm I earned

Deep throat training with anal beads, plus the orgasm I earned

jamieolive66

Enema Part 3 - 65ml

Enema Part 3 - 65ml

jamieolive66

Brushing nipples with toothpaste after 45 min of clothespins

Brushing nipples with toothpaste after 45 min of clothespins

jamieolive66

2x 3rd notch + 2x full length sounding + orgasm

2x 3rd notch + 2x full length sounding + orgasm

jamieolive66

Piss enema with chili flakes

Piss enema with chili flakes

jamieolive66

Ass fucking, 40 ball slaps

Ass fucking, 40 ball slaps

jamieolive66

Vibrator on cock + plug in ass

Vibrator on cock + plug in ass

jamieolive66

2min of strong vibes followed by 2 edges

2min of strong vibes followed by 2 edges

jamieolive66

2 edges as punishment for failing the training

2 edges as punishment for failing the training

jamieolive66

Cum on dildo, inserting into ass, and sucking on it for a punishment

Cum on dildo, inserting into ass, and sucking on it for a punishment

jamieolive66

Another morning edge

Another morning edge

jamieolive66

Edging again, it’s been 2 weeks since I’ve came/ruined

Edging again, it’s been 2 weeks since I’ve came/ruined

jamieolive66

Slaps Pt.4

Slaps Pt.4

jamieolive66

Inserting 2.5 ice cubes into my ass

Inserting 2.5 ice cubes into my ass

jamieolive66

400 slaps to the balls

400 slaps to the balls

jamieolive66

Celebratory orgasm for reaching Apprentice rank

Celebratory orgasm for reaching Apprentice rank

jamieolive66

9+ min of intense burn

9+ min of intense burn

jamieolive66

Urethra Training 3 (Week 2): Decided to do a bit of sounding,

Urethra Training 3 (Week 2): Decided to do a bit of sounding,

jamieolive66

Some action before calling it a night (didn’t realize camera

Some action before calling it a night (didn’t realize camera

jamieolive66

Day 2: Pee drinking while balls getting shocked (Task by u/TallConfidence9748)

Day 2: Pee drinking while balls getting shocked (Task by u/TallConfidence9748)

jamieolive66

Ball slapping punishment: 3 sets of 20

Ball slapping punishment: 3 sets of 20

jamieolive66

r/39st_chambers 30 Member Milestone Task Part 1

r/39st_chambers 30 Member Milestone Task Part 1

jamieolive66

r/39st_chambers 30 Member Milestone Task Part 2

r/39st_chambers 30 Member Milestone Task Part 2

jamieolive66

r/39st_chambers 30 Member Milestone Task Part 3

r/39st_chambers 30 Member Milestone Task Part 3

jamieolive66

Balls of Steel Training (138 slaps)

Balls of Steel Training (138 slaps)

jamieolive66

Edge, 1040 ball slaps, Orgasm

Edge, 1040 ball slaps, Orgasm

jamieolive66

Ass prep: Hair trimming and 3x 100ml enemas

Ass prep: Hair trimming and 3x 100ml enemas

jamieolive66

Spending the night plugged (going for 8 hours) [By u/JamesC12369]

Spending the night plugged (going for 8 hours) [By u/JamesC12369]

jamieolive66

400 ball slaps

400 ball slaps

jamieolive66

1 of 2 pee drinking for today

1 of 2 pee drinking for today

jamieolive66

Butt plug removal after 7.5 hrs continuously, 10 hrs if including

Butt plug removal after 7.5 hrs continuously, 10 hrs if including

jamieolive66

Ass “cleaning” with wet wipes

Ass “cleaning” with wet wipes

jamieolive66

Reinserting butt plug (2 hours to go), pee drinking 2 of 2, caning

Reinserting butt plug (2 hours to go), pee drinking 2 of 2, caning

jamieolive66

Ending my 12 hour butt plugged total for the day

Ending my 12 hour butt plugged total for the day

jamieolive66

Intense and humiliating ass to mouth dildo training - 225 reps

Intense and humiliating ass to mouth dildo training - 225 reps

jamieolive66

100 ass thrusts and 50+ mouth thrusts, using saliva as lube

100 ass thrusts and 50+ mouth thrusts, using saliva as lube

jamieolive66

0:00 Enema + ATM, 1:58 ATM after releasing enema, 6:56 ATM after

0:00 Enema + ATM, 1:58 ATM after releasing enema, 6:56 ATM after

jamieolive66

Enema liquid in mouth: 0:00 Round 1, 2:12 Round 2

Enema liquid in mouth: 0:00 Round 1, 2:12 Round 2

jamieolive66

575 slaps, 2 edges, 1 orgasm

575 slaps, 2 edges, 1 orgasm

jamieolive66

400 slaps, with 3 edges in between

400 slaps, with 3 edges in between

jamieolive66

Ants

Ants

* T O P L I S T * T O P L I S T *