videos / jamieolive66

jamieolive66 vid #25503241 Sliding out the sound without hands

Sliding out the sound without hands

jamieolive66 vid #12332057 350 ball slaps with metal ruler

350 ball slaps with metal ruler

jamieolive66 vid #10174003 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 vid #10516251 Urethra Training 4 (Week 2): Adding droplets of water to spread

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

jamieolive66 vid #14097004 Relief after 3 hours of butt plug

Relief after 3 hours of butt plug

jamieolive66 vid #15209672 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 vid #10118710 22 Feb (Day 2 of Training): 600x purple dildo fucks

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

jamieolive66 vid #10875522 Masturbating while drinking pee (+ bonus rope bondage) (Task

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

jamieolive66 vid #12231775 1200 ball slaps, 6 edges (part 2 of 2)

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

jamieolive66 vid #12298895 Deep throat training with anal beads, plus the orgasm I earned

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

jamieolive66 vid #14004238 Enema Part 3 - 65ml

Enema Part 3 - 65ml

jamieolive66 vid #14165254 Brushing nipples with toothpaste after 45 min of clothespins

Brushing nipples with toothpaste after 45 min of clothespins

jamieolive66 vid #15069015 2x 3rd notch + 2x full length sounding + orgasm

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

jamieolive66 vid #15216200 Piss enema with chili flakes

Piss enema with chili flakes

jamieolive66 vid #15237776 Ass fucking, 40 ball slaps

Ass fucking, 40 ball slaps

jamieolive66 vid #15321484 Vibrator on cock + plug in ass

Vibrator on cock + plug in ass

jamieolive66 vid #15326568 2min of strong vibes followed by 2 edges

2min of strong vibes followed by 2 edges

jamieolive66 vid #15460545 2 edges as punishment for failing the training

2 edges as punishment for failing the training

jamieolive66 vid #15461773 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 vid #15929804 Another morning edge

Another morning edge

jamieolive66 vid #16055600 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 vid #17585914 Slaps Pt.4

Slaps Pt.4

jamieolive66 vid #18214231 Inserting 2.5 ice cubes into my ass

Inserting 2.5 ice cubes into my ass

jamieolive66 vid #20012537 400 slaps to the balls

400 slaps to the balls

jamieolive66 vid #10142888 Celebratory orgasm for reaching Apprentice rank

Celebratory orgasm for reaching Apprentice rank

jamieolive66 vid #10375640 9+ min of intense burn

9+ min of intense burn

jamieolive66 vid #10466492 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 vid #10523403 Some action before calling it a night (didn’t realize camera

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

jamieolive66 vid #10912962 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 vid #10944649 Ball slapping punishment: 3 sets of 20

Ball slapping punishment: 3 sets of 20

jamieolive66 vid #11602684 r/39st_chambers 30 Member Milestone Task Part 1

r/39st_chambers 30 Member Milestone Task Part 1

jamieolive66 vid #11602730 r/39st_chambers 30 Member Milestone Task Part 2

r/39st_chambers 30 Member Milestone Task Part 2

jamieolive66 vid #11602760 r/39st_chambers 30 Member Milestone Task Part 3

r/39st_chambers 30 Member Milestone Task Part 3

jamieolive66 vid #12124917 Balls of Steel Training (138 slaps)

Balls of Steel Training (138 slaps)

jamieolive66 vid #12213873 Edge, 1040 ball slaps, Orgasm

Edge, 1040 ball slaps, Orgasm

jamieolive66 vid #12239185 Ass prep: Hair trimming and 3x 100ml enemas

Ass prep: Hair trimming and 3x 100ml enemas

jamieolive66 vid #12242623 Spending the night plugged (going for 8 hours) [By u/JamesC12369]

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

jamieolive66 vid #12243295 400 ball slaps

400 ball slaps

jamieolive66 vid #12243379 1 of 2 pee drinking for today

1 of 2 pee drinking for today

jamieolive66 vid #12258365 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 vid #12267853 Ass “cleaning” with wet wipes

Ass “cleaning” with wet wipes

jamieolive66 vid #12269460 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 vid #12272075 Ending my 12 hour butt plugged total for the day

Ending my 12 hour butt plugged total for the day

jamieolive66 vid #12309106 Intense and humiliating ass to mouth dildo training - 225 reps

Intense and humiliating ass to mouth dildo training - 225 reps

jamieolive66 vid #12345036 100 ass thrusts and 50+ mouth thrusts, using saliva as lube

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

jamieolive66 vid #12350164 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 vid #12350259 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 vid #12688746 575 slaps, 2 edges, 1 orgasm

575 slaps, 2 edges, 1 orgasm