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RubyLippy

Deviant for 5 months•379 Watchers•469 Watching•110 Deviations
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Collections

Goths Making Out

Sissy Dates

44 deviations
Wives make their sissy husbands kiss

Fully Femme at Last

24 deviations
The Role of a Lifetime Part 3 (2/2)

Sissy Sagas

78 deviations
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Femmeulators

27 deviations
Wives make their sissy husbands kiss

Hubbettes

56 deviations
The Silk Exchange (1/2)

Feeling Sooo Femme Sissy

56 deviations
Practice Makes Perfect

Sissy Training

32 deviations
Sissy trying on dresses for his big date!

Sissy Shopping

7 deviations
Humiliation-revenge-boy-sissified

Stepford Sisy Sons

11 deviations
The Silk Exchange (1/2)

Closet Siss Awakens

35 deviations
Seeing a different person

Mistress Lips Sissy Salon

15 deviations
The Silk Exchange (1/2)

Sissy Skirting

6 deviations
Vintage Goth

Crossing Over to Femme

52 deviations
Burlesque grandma lingerie model woman old babe (

Lingerie for Sissy

28 deviations
Even more Flickr ladies (IYKYK)

Sissy Date Night Prep

8 deviations
He's gone... we have at least two hours

Assisted Transfemminization

38 deviations
The Silk Exchange (1/2)

Cross dresser Dreams

21 deviations
Before and after makeup and wig on man

Nu Trans Sissy Faces

36 deviations
Housewife Adventures - Lost the Key Edition (9)

Stepford Hubbettes

42 deviations
Delusional Dudes Dazzling Dolls Desirable Dates

Trans Sissy Lovers

5 deviations
The Role of a Lifetime (2/2)

Trans Formation

41 deviations
Trying My Wife's Old Prom Dress - Sissy Story

Femme Makeover

21 deviations
Feminized son in a pink dress chosen by mom (p1)

Femme Bois

139 deviations
Beautiful wife for a bossy woman (part 2)

Mothers Sissy Sons

136 deviations
Feminized son in a tiny and puffy dress

Aunties Sissy Nephettes

110 deviations