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Author: malechastitylife

Site owner of www.malechastitylife.com and avid chastity believer and follower.

Now Available! From Stepbrother to Stepsissy Part 4

Now Available! From Stepbrother to Stepsissy Part 4

Announcing the release of our short story, From Stepbrother To Stepsissy Part 4.

by: malechastitylifePosted on: June 30, 2022June 29, 2022
Now Available! From Stepbrother to Stepsissy Part 3

Now Available! From Stepbrother to Stepsissy Part 3

Announcing the release of our short story, From Stepbrother To Stepsissy Part 3.

by: malechastitylifePosted on: June 23, 2022June 29, 2022
Now Available! My Roommate the Sissy

Now Available! My Roommate the Sissy

Announcing the release of our short story, My Roommate the Sissy: Feminized & Pleasured.

by: malechastitylifePosted on: June 18, 2022June 29, 2022
How to be a Chastity Keyholder

How to be a Chastity Keyholder

Our guide on the key considerations you should make as a chastity keyholder.

by: malechastitylifePosted on: June 17, 2022May 3, 2022
Chastity Cage Cleaning Tips

Chastity Cage Cleaning Tips

Learn the best ways to stay safe in chastity with proper chastity cage hygiene.

by: malechastitylifePosted on: June 10, 2022April 21, 2022
Now Available! From Stepbrother to Stepsissy Part 2

Now Available! From Stepbrother to Stepsissy Part 2

Announcing the release of our short story, From Stepbrother To Stepsissy Part 2.

by: malechastitylifePosted on: June 9, 2022June 29, 2022
How to Make Your Man Cum in His Chastity Cage

How to Make Your Man Cum in His Chastity Cage

Learn four fun and sexy methods to make your man cum while wearing his chastity cage.

by: malechastitylifePosted on: June 3, 2022April 21, 2022
The Sissy Bet: Part 8

The Sissy Bet: Part 8

The final part of our sissy story, The Sissy Bet. My life allows me to orgasm under one condition, I agree to be her sissy maid.

by: malechastitylifePosted on: May 27, 2022May 27, 2022
Now Available! From Stepbrother to Stepsissy Part 1

Now Available! From Stepbrother to Stepsissy Part 1

Announcing the release of our short story, From Stepbrother To Stepsissy Part 1.

by: malechastitylifePosted on: May 26, 2022June 29, 2022
The Sissy Bet: Part 7

The Sissy Bet: Part 7

Part 7 of our sissy story, The Sissy Bet. My wife rewards my cleaning by pegging me.

by: malechastitylifePosted on: May 20, 2022April 6, 2022
The Sissy Bet: Part 6

The Sissy Bet: Part 6

Part 6 of our sissy story, The Sissy Bet. My wife makes me clean the house dressed as a sissy maid and then judged my cleaning.

by: malechastitylifePosted on: May 13, 2022April 6, 2022
The Sissy Bet: Part 5

The Sissy Bet: Part 5

Part 5 of our sissy story, The Sissy Bet. My wife demands that I clean the house dressed as a maid.

by: malechastitylifePosted on: May 6, 2022April 6, 2022
Now Available! Becoming a Sissy Maid: Unlocking Hidden Desires

Now Available! Becoming a Sissy Maid: Unlocking Hidden Desires

We’re proud to announce the release of our first book, Becoming a Sissy Maid: Unlocking Hidden Desires.

by: malechastitylifePosted on: May 2, 2022June 29, 2022
The Sissy Bet: Part 4

The Sissy Bet: Part 4

Part 4 of our sissy story, The Sissy Bet. My wife and I go home to try on our new bras and panties together.

by: malechastitylifePosted on: April 29, 2022March 25, 2022
The Sissy Bet: Part 3

The Sissy Bet: Part 3

Part 3 of our sissy story, The Sissy Bet, when my wife takes me to the store to buy panties.

by: malechastitylifePosted on: April 22, 2022March 25, 2022
The Sissy Bet: Part 2

The Sissy Bet: Part 2

The continuation of our sissy story, The Sissy Bet. About how a bet on a football game turned me into a sissy slave.

by: malechastitylifePosted on: April 15, 2022March 25, 2022
The Sissy Bet: Part 1

The Sissy Bet: Part 1

The story of how losing a simple chastity bet on a football game changed my life.

by: malechastitylifePosted on: April 8, 2022March 19, 2022
Sissy Husband Rules to Live By

Sissy Husband Rules to Live By

Are you an inspiring sissy husband or are you a wife looking to turn your husband into your sissy? Learn the rules that every sissy husbands should abide to.

by: malechastitylifePosted on: March 25, 2022June 4, 2022
Best Ways to Tease and Deny in Chastity

Best Ways to Tease and Deny in Chastity

Teasing and denying is the act of arousing your man and then not allowing him to orgasm. Learn our favorite ways to tease and deny.

by: malechastitylifePosted on: March 18, 2022January 22, 2022
How Cuckolds Should Prepare For Their Wife’s Dates

How Cuckolds Should Prepare For Their Wife’s Dates

When a hot wife and her new bull have a date, there is a lot that the wife’s husband, her cuckold, should be involved in. Learn how cuckolds should help.

by: malechastitylifePosted on: March 11, 2022June 4, 2022
Cucked Abroad: Part 5

Cucked Abroad: Part 5

The conclusion to the story of how my wife turned me into her cuckold while on a trip to Mexico.

by: malechastitylifePosted on: March 4, 2022January 22, 2022
7 Steps to Make Your Husband Your Sissy

7 Steps to Make Your Husband Your Sissy

There’s nothing more satisfying then seeing your husband progress into your sissy. Get started today!

by: malechastitylifePosted on: February 25, 2022January 22, 2022
Cucked Abroad: Part 4

Cucked Abroad: Part 4

The continued story of my wife cuckolding me on her trip to Mexico. Now she’s meeting up with guys in their hotel room.

by: malechastitylifePosted on: February 18, 2022January 22, 2022
Why I Keep Him Caged and Plugged

Why I Keep Him Caged and Plugged

What should you do if you want to take your chastity relationship to the next level? Learn why you should keep him caged and plugged.

by: malechastitylifePosted on: February 11, 2022June 29, 2022
Cucked Abroad: Part 3

Cucked Abroad: Part 3

Part 3 in the continued story of my wife’s trip to Mexico and her journey to turn me into her cuckold. She’s now in Mexico and on the hunt.

by: malechastitylifePosted on: February 4, 2022February 4, 2022

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Articles

  • Now Available! From Stepbrother to Stepsissy Part 4
  • Now Available! From Stepbrother to Stepsissy Part 3
  • Now Available! My Roommate the Sissy
  • How to be a Chastity Keyholder
  • Chastity Cage Cleaning Tips
  • Now Available! From Stepbrother to Stepsissy Part 2
  • How to Make Your Man Cum in His Chastity Cage
  • The Sissy Bet: Part 8
  • Now Available! From Stepbrother to Stepsissy Part 1
  • The Sissy Bet: Part 7
  • The Sissy Bet: Part 6
  • The Sissy Bet: Part 5
  • Now Available! Becoming a Sissy Maid: Unlocking Hidden Desires
  • The Sissy Bet: Part 4
  • The Sissy Bet: Part 3
  • The Sissy Bet: Part 2
  • The Sissy Bet: Part 1
  • Sissy Husband Rules to Live By
  • Best Ways to Tease and Deny in Chastity
  • How Cuckolds Should Prepare For Their Wife’s Dates
  • Cucked Abroad: Part 5
  • 7 Steps to Make Your Husband Your Sissy
  • Cucked Abroad: Part 4
  • Why I Keep Him Caged and Plugged
  • Cucked Abroad: Part 3
  • Chastity Marriage Vows
  • Punish Him with Post Orgasm Torture
  • Signs You’re Ready for a Female Led Relationship
  • Cucked Abroad: Part 2
  • How to Reward Your Chastity Husband
  • Cucked Abroad: Part 1
  • Common Male Chastity Misconceptions
  • How to Turn Your Husband into Your Cuckold
  • Chastity Text Messages to Tease Your Man
  • Forced to be a Sissy Slave: Part 7
  • Why You Need to Be in Long Term Chastity
  • Advanced Sissy Training: Part 6
  • Start Dominating Your Husband in Chastity
  • Desperate to Be A Sissy Maid: Part 5
  • First Steps Towards Becoming a Sissy
  • How Male Chastity Improved My Relationship
  • How My Wife Feminized Me: Part 4
  • Retaking Control with Femdom Chastity
  • Punished as a Sissy Maid: Part 3
  • Chastity Relationship Rules
  • Chastity Punishments List
  • Benefits of Solo Chastity
  • Being a Sissy Maid: Part 2
  • Solo Chastity Games
  • Guide to Chastity Humiliation

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Recent Articles
  • Now Available! From Stepbrother to Stepsissy Part 4
  • Now Available! From Stepbrother to Stepsissy Part 3
  • Now Available! My Roommate the Sissy
  • How to be a Chastity Keyholder
  • Chastity Cage Cleaning Tips
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