Free Chastity & Sissy Stories

Steve and Becky have a problem. Steve is just too small to satisfy her sexually. They try pills, pumps, and chastity cages to improve their relationship and nothing works.

It soon becomes clear to Becky that her relationship is never going to satisfy her the way she needs. She needs more and she knows exactly how she will get it.

With Steve still locked in his chastity cage, she informs him that when she’s overseas for her friend’s bachelorette party weekend, she will be on the hunt for the one, big thing that has been missing from her love life.

Who knew a simple bet with my wife could change my life so drastically?

Sean is a passionate football fan. However, his wife, Christina, is anything but and believes watching football is a waste of time and interfering with their relationship. In order to allow Sean to keep watching the game he loves, she makes him agree to wear a chastity cage and devote all of his free time to her.

The cage isn’t enough for Christina and she soon starts implementing chastity bets on each game to make things more interesting for her. If Sean wins the bet, he gets a reward, but if he loses, he gets punished. The bets are simple enough... until the championship game comes around Christina wants to place a championship level bet - if Sean wins then he will get a night of passionate sex, but if he loses he has to become her sissy slave.

When he loses the bet, Christina wastes no time in starting her plan to transform her husband to a submissive sissy slave. Through feminization, crossdressing, and domination, Christina unveils her plan to not only turn Sean into her sissy slave, but eventually, her sissy maid.

When Lila’s mysterious antique chest arrives, Thomas expects dusty old clothes; not a night that will change him forever.

One lost bet. One shimmering vintage dress. One slow, teasing fitting that turns playful into something far more intimate.

As the magical fabric molds to his body, Thomas feels his muscles soften, his chest swell, and his hips curve into undeniably feminine lines. With every brush of powder from the antique makeup kit, his face becomes softer, his lips fuller, his lashes longer… until the man he was disappears completely. But the real shock comes when Lila’s hand slips between his thighs and finds something new — warm, wet, and aching for her touch.

What starts as reluctant surrender quickly melts into breathless pleasure as Lila claims her beautiful new girl. By morning, Thomas is gone. In his place is Tara; soft, curvy, and completely hers. And Lila has no intention of ever letting her go.

A steamy, magical feminization romance where one antique chest unlocks forbidden desires, irreversible changes, and a passionate new future between two lovers.