Dildo Challenge

The size difference is off the charts. That’s why I belong is chastity.
The size difference is off the charts. That’s w ...
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Sissy Donna
Sissy in chastity vs dildo
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Mistress E Have a seat on it and show how a good sissy takes a cock
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Sissy Donna I did, Mistress. I have quite a bit now. It’s really big!
Sissy chastity dildo humiliation
Sissy chastity dildo humiliation
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ineedpanties
Chastised Sissy Permanently
Strapon goddess humiliates inferior dicklette
Strapon goddess humiliates inferior dicklette
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SPH JOI
Small Dicklette Captions
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Tiny dick83 my tiny cock needs to be humiliated
Small pinky dicks can not compete with big man meat
Small pinky dicks can not compete with big man meat
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SPH JOI
Penis Rating & Humiliating
Help Donna deep throat some dick
Help Donna deep throat some dick
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Fem Sissy
Sissy Cock Sucker Training
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Femdoms Rule Gag on it sissy slut
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Show Your Tiny Dick Liked and here's a comment for another one. Gag on that rubber cock lol
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Juliegurl Take it all the way in
It doesn’t get smaller than this. No seriously, it doesn’t.
It doesn’t get smaller than this. No seriously, ...
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Sissy Donna
Sissy chastity boy
Dildos feel better than small dicks
Dildos feel better than small dicks
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SPH JOI
Small Dicklette Captions
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2small4u my ex also preferd her dildo. my job was eating pussy
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Tiny dick83 it's true my wife prefers to stick her big dildos in her pussy rather than my tiny cock
Tiny Prick Terry vs Big Dick Dildo
Tiny Prick Terry vs Big Dick Dildo
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Terry the Fairy
Tiny Dick Terry
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Precisedb30 I’ll suck those big fat balls while I jerk my hung cock and sit on that long rubber
Sorry sweetie, 3.5 will never equal 9.5. You will always be a micropenis sissy loser, DJ. Now gu ...
Sorry sweetie, 3.5 will never equal 9.5. You wi ...
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Sissy Donna
Dildo challenges and comparisons
Compare your cocklette to my dildos
Compare your cocklette to my dildos
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Show Your Tiny Dick
Tiny Cocklettes
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Tiniestdickwimpever I can't compare to your dildos or real men's size cock's but I can compare my fully erect mi...
Sissy Webcam Trainers
4 versus 10. I don’t think 4 will ever come close. I can dream though!
4 versus 10. I don’t think 4 will ever come clo ...
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Sissy Donna
Dildo challenges and comparisons
10 inches versus 1 1/2. It’s not really a competition, is it?
10 inches versus 1 1/2. It’s not really a compe ...
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Sissy Donna
Sissy in chastity vs dildo
Dildos compared to my dicklette.
Dildos compared to my dicklette.
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Jerkieboi
Dildo Comparisons (toys were ex’s)
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cjack Cute little dick!
Dicklette Failed the Dildo Challenge
Dicklette Failed the Dildo Challenge
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Show Your Tiny Dick
Dildo Challenge
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Sissy Donna That’s exactly how well I would do. Maybe worse actually
Penis Ratings
Dicklette vs Peter & Lex
Dicklette vs Peter & Lex
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Jerkieboi
Tiny Penis Club Member
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cjack Nice. You should sit on them until you have a sissygasm!
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Jerkieboi TY, Sir … i have … and, i get pegged frequently by them.
Awe sweetie, you simply will just never measure up. That’s okay, you enjoy taking big dicks, don ...
Awe sweetie, you simply will just never measure ...
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Sissy Donna
Cucky in women’s skinny jeans
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cjack You’d love taking my big dick and my loads. You’d love being my little sissy!
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Cucky Yes I would, Sir.
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cjack Such a good sissy!
How did I do this time, Mistress? Not well, cucky, not well at all. 🤣
How did I do this time, Mistress? Not well, cuc ...
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Sissy Donna
Pink V chastity
Micro penis versus 9 inch dildo. The winner is… not cucky!
Micro penis versus 9 inch dildo. The winner is… ...
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Sissy Donna
Dildo challenges and comparisons
Show your penis to women online
Comparing and dreaming of what I wish I had!
Comparing and dreaming of what I wish I had!
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Sissy Donna
Sissy in chastity vs dildo
The reason they dont make small dildos
The reason they dont make small dildos
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Foot Licker
Your Dick is Small
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Baby dick 😰😖
My life in one picture. Just add a chastity cage.
My life in one picture. Just add a chastity cage.
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Sissy Donna
Dildo challenges and comparisons
Maybe, ummm, I’ll have better luck tomorrow.
Maybe, ummm, I’ll have better luck tomorrow.
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Sissy Donna
Dildo challenges and comparisons
There’s really not much I can say except yes I’m this tiny!
There’s really not much I can say except yes I’ ...
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Sissy Donna
Dildo challenges and comparisons
Now cucky, which do you think women would rather? Be honest, sissy.
Now cucky, which do you think women would rathe ...
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Sissy Donna
Dildo challenges and comparisons
Even with chastity to keep his little dick hard, cucky still fails the challenge.
Even with chastity to keep his little dick hard ...
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Sissy Donna
Spiked chastity

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