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Skippy

@sonskippy.bsky.social
447 followers 146 following 401 posts

Submissive son to @bostonleatherman.bsky.social. A leather, rubber, bondage, and kink enthusiast exploring and looking to connect with Dads, Sirs, Doms, Masters, sons, boys, and slaves.

PostsRepliesMedia
Skippy @sonskippy.bsky.social · 13/09/2026
Autumn seasonal colour change?…nah….much prefer how a Sir’s marks go from red, to purple, to yellow. Thank You, Sir!
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Skippy @sonskippy.bsky.social · 12/09/2026
IYKYK….Folsom Europe in Berlin…..
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Skippy @sonskippy.bsky.social · 11/09/2026
That’s gonna leave a mark! Oh wait….it already did!
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Skippy @sonskippy.bsky.social · 27/08/2026
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Skippy @sonskippy.bsky.social · 28/07/2026
Ritual. Kneeling before Dad to put His boots on His feet, lacing them just as He likes. In the same position to take them off….right, then left, and the privilege of being allowed some deep relaxing breaths.
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Skippy @sonskippy.bsky.social · 28/07/2026
Had the opportunity recently to spend some time honouring the boots of the first Master i ever served - almost 20 years ago. GRATITUDE!
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Skippy @sonskippy.bsky.social · 14/07/2026
There is nothing like a solid hour of bootworship in front of my Dad, while He enjoys a cigar with another LeatherMan…has me attend to both sets of boots…and getting fed ash by both of Them.
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Skippy @sonskippy.bsky.social · 12/07/2026
Current POV…Dad is working, meaning quiet. Forward angle, and reverse angle, while i wait for the laundry to be ready to put in the dryer.
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Skippy @sonskippy.bsky.social · 11/07/2026
So far…a perfect Saturday. On my back while Dad opened and stretched my hole…on my hands and knees for a post-stretch paddling….sucking Dad’s cock to completion…and the current POV - massaging and kissing Dad’s feet til He fell asleep. Now just to kneel here and keep quiet til He wakes up………….
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Skippy @sonskippy.bsky.social · 29/06/2026
That is difficult to get behind, considering the move from private favourites, to public follows. And then there’s this…
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Skippy @sonskippy.bsky.social · 28/06/2026
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Skippy @sonskippy.bsky.social · 28/06/2026
This has been circulating, and i think Recon should publicly address it. Privacy has been reduced with the new upgrade in more than one manner…but this is very concerning…
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Skippy @sonskippy.bsky.social · 23/05/2026
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Skippy @sonskippy.bsky.social · 23/05/2026
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Skippy @sonskippy.bsky.social · 11/05/2026
Not a lot of bondage needed…i wasn’t going anywhere.
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Skippy @sonskippy.bsky.social · 11/05/2026
Gotta pay attention in the drive-thru…never know what you might see….
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Skippy @sonskippy.bsky.social · 06/04/2026
Some discipline, followed by a few hours in the straitjacket, restraints, and white noise headphones while Dad went an enjoyed some social time with other Sirs and kept tabs on me live streamed to His phone.
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Skippy @sonskippy.bsky.social · 28/03/2026
First foray into silicone gear - and initial impression is 😈.
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Skippy @sonskippy.bsky.social · 25/02/2026
Perfect way to relax….
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Skippy @sonskippy.bsky.social · 30/01/2026
me & m’ Dad!….MAL2025!
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Skippy @sonskippy.bsky.social · 25/01/2026
Relaxed vibe…semi-hypnotic lights and music…and an eagerness to be opened up brought me to the brink of my first fist! Workin’ on it!
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Skippy @sonskippy.bsky.social · 22/01/2026
Mid-beating in the lobby at MAL. Pink pecs…but Dad decided it was time for the drooler gag by @mrsleather.bsky.social - Photo credit to @mrkristofer.bsky.social - thank You, Sir!
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Skippy @sonskippy.bsky.social · 19/01/2026
BLUF social at TRADE…MAL 2026. www.kaloramaphoto.com/TRADE/BLUFDC...
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Skippy @sonskippy.bsky.social · 19/01/2026
Final night at MAL. Great cigar social…dinner…chat with so many hot LeatherMen. Another fun event!
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Skippy @sonskippy.bsky.social · 18/01/2026
Gear off after night 2 at MAL - took 68 (IYKYK) strokes of Dad’s strap across my chest in the lobby…bruises already beginning to show. A true highlight?…being fed three loads of piss by @mrkristofer.bsky.social…thank You, Sir!
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Skippy @sonskippy.bsky.social · 17/01/2026
POV before my training started last night….
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Skippy @sonskippy.bsky.social · 16/01/2026
Enjoying the drive to MAL…Dad’s ALWAYS in the driver’s seat!
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Skippy @sonskippy.bsky.social · 29/12/2025
This is mine, Sir….where i belong!!!!
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Skippy @sonskippy.bsky.social · 26/12/2025
Hope all the Sirs, (and boys), are out there crushing it over the holidays……
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Skippy @sonskippy.bsky.social · 26/12/2025
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Skippy @sonskippy.bsky.social · 19/12/2025
i was introduced to the sensory feast from receiving a beating by an amazing Master on the Cape. i am filled with a gratitude that comes from knowing a Mentor is invested in my development and unlocking my potential. Thank your Doms and Sirs, boys…we are indeed fortunate for their tutelage.
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Skippy @sonskippy.bsky.social · 05/12/2025
Great visit to SpeXter @spexter.bsky.social in Munich yesterday…super friendly staff…and picked up a couple of items to add to the packing list for MAL! If you’re in the city - recommend a look!
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Skippy @sonskippy.bsky.social · 29/11/2025
So bored…and horny in the airport lounge that i am now imagining what each guy that passes by would look like in leather or rubber. Preparing for arrival in Munich!
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Skippy @sonskippy.bsky.social · 19/11/2025
Non-kink shot enjoying a perfect day for wearing leather…and over my shoulder - a bourbon coming right up!
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Skippy @sonskippy.bsky.social · 12/11/2025
Two workouts today….at the gym, and at home with my #crackstuffers Smooth Riders - sm, med, and working on the lge. A boy needs goals.
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Skippy @sonskippy.bsky.social · 11/11/2025
Ready for some hole training in Dad’s collar, Dad’s cage, and custom armbands - thanks to @mrkristofer.bsky.social and @fdaddylondon.bsky.social
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Skippy @sonskippy.bsky.social · 09/11/2025
How a sub centres itself. 😈
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Skippy @sonskippy.bsky.social · 05/11/2025
Poppers, bondage, milker, full rubber and some time spent in storage and under the sublime control of @stiefelkopp.bsky.social in His dungeon, made for a happy gimp. A truly amazing Sir.
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Skippy @sonskippy.bsky.social · 26/10/2025
POV LOctober housework, preparing for dinner guests….
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Skippy @sonskippy.bsky.social · 14/10/2025
Dad smoking up His right glove…right before it got clamped over my nose & mouth.
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Skippy @sonskippy.bsky.social · 14/10/2025
Sealed in rubber.
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Skippy @sonskippy.bsky.social · 06/10/2025
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Skippy @sonskippy.bsky.social · 08/08/2025
Ashtray service when Dad or other LeatherMen are enjoying their cigars is one of my favourite ways of being put to good use.
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Skippy @sonskippy.bsky.social · 06/08/2025
Stills from a video…those amazing moments during a beating when i feel the sting of Dad’s implements…and the touch of His gloved hands. boy Bliss!
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Skippy @sonskippy.bsky.social · 06/08/2025
Giving the Master’s boots a thorough polish….
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Skippy @sonskippy.bsky.social · 03/08/2025
i had a traumatic first experience with chastity - a Dom who applied it in heavy bondage, and proceeded to deliberately injure me and act without my consent…my Dad has since used careful, meaningful application to help me embrace it, and gain deep understanding of its intensity in a healthy dynamic🙏
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Skippy @sonskippy.bsky.social · 03/08/2025
Gratitude. Genuine, for the Man and Master who truly set me on the path.
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Skippy @sonskippy.bsky.social · 02/08/2025
An evening of bourbon and chat for three Sirs…and bootworship for this sub, Sir!
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Skippy @sonskippy.bsky.social · 31/07/2025
TBT, if that’s still a thing….great session with a visiting Dom about five years ago.
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Skippy @sonskippy.bsky.social · 30/07/2025
Happy place.
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