sissyslutcaps: The weekend after you and your serious girlfriend had broken up, one of your female friends had a good idea to make you feel better. Since you were broke, that’s why your girlfriend left you, she thought you should dress yourself up

sissyslutcaps: The weekend after you and your serious girlfriend had broken up, one of your female friends had a good idea to make you feel better. Since you were broke, that’s why your girlfriend left you, she thought you should dress yourself up

sissyslutcaps: The weekend after you and your serious girlfriend had broken up,

Sissyslutcaps: After Ages Of Searching, Your Agent Said He Finally Found Some Work For You. It Was However A Female Role, So You Would Need To Look The Part. You Don’t Drive And Were Wary Of Taking The Bus All Dressed Up, So You Asked Your Agent For

Sissyslutcaps: Your Parents Were Worried About You Being More Masculine, So They Hired You A Personal Trainer. He Trained You That Rich White Bois Are To Always Follow Black Mens Orders. It Was Hard At First, But After He Slapped You Around Several Times

Sissyslutcaps: Late At Night When You Thought Everyone Had Gone Home For The Night, You Snuck Into Another Office On Your Floor And Found Some Spare Clothes Of A Secretary You Admired. You Dolled Yourself Up With Her Spare Makeup And Put On Her Work

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Sissyslutcaps: When You Started Getting More Attention From Boys Your Parents Lied About Your Gender To Get You Into An All Girls School. Little Did They Know That Your Walk To School Was A Gambit Of Horny Young Boys And Pervy Old Men. The Men At The

Sissyslutcaps: Some Of Your Older Brother’s Friends Started To Notice How Much You Where Developing. One Of Them Took An Exacto Knife To Your Jeans, But Just Enough To Compromise The Stitching. Then He Hid The Remote And Kept Pestering You To Go Change

Sissyslutcaps: Sorry For The Small Text :(

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Sissyslutcaps: A Couple Of Related Caps

Sissyslutcaps: A Bit Of A Longer Sissy Caption That Wouldn’t Realistically Fit, Hope This Format Is Still Enjoyable :) In High School You Had Mostly Girl Friends, Tonight You Went To A Sleepover And Everyone Gave Each Other Makeovers, They Insisted

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