Site Header

Shop
DreamUp AI ArtDreamUp
JoinLog In
Upgrade to Core

50% off for a limited time!

Get Core
Theme
Help Center
Terms of Service
Privacy Policy
DeviantArt - Homepage
DeviantArt FacebookDeviantArt XDeviantArt Instagram
AboutContactCore MembershipSell Your Art
DevelopersAdvertiseCareersHelp Center
Terms of ServiceCopyright PolicyPrivacy PolicyEtiquette
Watch Team and join our Community Group for the latest updates and activities.
Join Community
©2026 DeviantArt
All rights reserved
Young Sissy in mothers' gown, 1980s. lorrainesydney on DeviantArthttps://www.deviantart.com/lorrainesydney/art/Young-Sissy-in-mothers-gown-1980s-1070978044lorrainesydney

Deviation Actions

lorrainesydney's avatar

Young Sissy in mothers' gown, 1980s.

By
lorrainesydney
Published: Jul 4, 2024
3.3K Views
vintagedress80s1980scrossdressercrossdressingtransvestite

Description

Young Sissy in mothers' gown, 1980s.

Image size
603x826px 144.85 KB
© 2024 - 2026 lorrainesydney
Comments4
anonymous's avatar
Join the community to add your comment. Already a deviant? Log In
kaecelius's avatar
kaecelius
Oct 13, 2025

It's good to start young if you want to stick it out

More by lorrainesydney
Sensational Magazine Article, 1980slorrainesydney on DeviantArt
It's my first day at the Flamingo clublorrainesydney on DeviantArt
Deviant Artists at home! lorrainesydney on DeviantArt
Sissy Style. Becoming a sissylorrainesydney on DeviantArt
Almost time to look back on 2025....lorrainesydney on DeviantArt
Transvestite enjoys attention from admirer #1lorrainesydney on DeviantArt
Material girl!lorrainesydney on DeviantArt
Getting my look right for the festive season!lorrainesydney on DeviantArt
Sissy enjoys attention from Daddylorrainesydney on DeviantArt
Promoted Deviations
Aunty Knew Exactly What Darren Wanted For His BdayPrincess-Jen-x on DeviantArthttps://www.deviantart.com/princess-jen-x/art/Aunty-Knew-Exactly-What-Darren-Wanted-For-His-Bday-1289994242Princess-Jen-x
Vintage Wedding DressAI-Satin-Chic on DeviantArt
Stuck As a MaidIvyRoseTGlued on DeviantArthttps://www.deviantart.com/ivyrosetglued/art/Stuck-As-a-Maid-1289939110IvyRoseTGlued
Suggested Deviants
Badkittymedia
1950s Sissy Fashion Guide 1Badkittymedia on DeviantArt
1950s Sissy Fashion Guide 2Badkittymedia on DeviantArt
FemBoy Magazine Jan 2026 - Full SizedBadkittymedia on DeviantArt
kathleen43
Becoming Posh, or, My Fair 'Lady'kathleen43 on DeviantArt
1950s Hunky Strong Bodybuilder Buxom Transvestitekathleen43 on DeviantArt
70s Sissy Wedding Serieskathleen43 on DeviantArt
iDecideLand
Deep and Pretty boys!iDecideLand on DeviantArthttps://www.deviantart.com/idecideland/art/Deep-and-Pretty-boys-1246970363iDecideLand
Playtime For Ladies!iDecideLand on DeviantArthttps://www.deviantart.com/idecideland/art/Playtime-For-Ladies-1065814347iDecideLand
Thank You Both For Dressing Me SO Pretty!iDecideLand on DeviantArthttps://www.deviantart.com/idecideland/art/Thank-You-Both-For-Dressing-Me-SO-Pretty-1054449415iDecideLand
MistressOfLove
9de27520-4ab7-4879-8708-e30bf6a60a27
My precious
6 Subscribers
Boosted
Over 4000 femdom POV pictures Includes sock gags, duct tape, foot fetish, cleave gags and a lot more
$30/month
Subscribe
Suggested Collections
00AlphaMale
Miss Gay 1963 - Evening gown competition00AlphaMale on DeviantArt
1950ies Gay Sissywife with husband00AlphaMale on DeviantArt
Beautiful Sissy00AlphaMale on DeviantArt
Aunties Sissy Nephews
Mothers Special ProjectLambs01 on DeviantArt
Christeen 8aa38c4a9926011a820185fe54abc6c7CaroleJean on DeviantArthttps://www.deviantart.com/carolejean/art/Christeen-8aa38c4a9926011a820185fe54abc6c7-1076516211CaroleJean
Aunt and nephew posing in their new velvet skirts.Velvetpet on DeviantArt
Femulation 2
Grandpa and His MiniskirtsStana-Stana on DeviantArt
Beautiful Crossdresser At A Library 1980shikes49 on DeviantArt
Zip!Stana-Stana on DeviantArt
More Like This
1950s Sissy Fashion Guide 1Badkittymedia on DeviantArt
DAMSEL AT A PARTYdlang on DeviantArthttps://www.deviantart.com/dlang/art/DAMSEL-AT-A-PARTY-1136165410dlang
Deep and Pretty boys!iDecideLand on DeviantArthttps://www.deviantart.com/idecideland/art/Deep-and-Pretty-boys-1246970363iDecideLand
Mommy and her Daughter sharing their Sissyboi... Pueppchen6 on DeviantArthttps://www.deviantart.com/pueppchen6/art/Mommy-and-her-Daughter-sharing-their-Sissyboi-1027651413Pueppchen6
Sissy dreams she is Cinderella (3/3)MarinaGer on DeviantArt
I Made My Sister My MaidLadeeAlana on DeviantArthttps://www.deviantart.com/ladeealana/art/I-Made-My-Sister-My-Maid-1157187497LadeeAlana
Not At Mens WearhouseStana-Stana on DeviantArthttps://www.deviantart.com/stana-stana/art/Not-At-Mens-Wearhouse-996176754Stana-Stana
Miss Elaine Maid Vikki 10ricarda99 on DeviantArthttps://www.deviantart.com/ricarda99/art/Miss-Elaine-Maid-Vikki-10-1059994267ricarda99
Sissy Maids Fashion Magazine August 2024MaidTeri022 on DeviantArthttps://www.deviantart.com/maidteri022/art/Sissy-Maids-Fashion-Magazine-August-2024-1081418108MaidTeri022