Chastity Lipstick Stories

30,354 results
Orientation
Length
Source
Infinite Scroll

Letter from Turkey Thicket

by justincbenedict on Sep 15, 2017
BDSM

Dear Shoeblossom... Inspired by Grant and Lyla's "Letter from Fritters, Alabama" I send you this! I bade Vince good night, kissing him on the cheek. Vince looked a bit dazed. "Troyce, you don't have to end it here. Your husband is clearly not what you want...you like me, right?" It was hard for him, my sudden distance, since my tongue had been plunging i...

Letter From Tacoma

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: When my husband, who is owner and ringmaster of the Epic Circus, comes into our hotel room (We, thankfully, don't have to live in the circus trailers) I'm ready for him. He lays the whip down, and then it's my turn... "Strip it all off Apollo, my love! Now you'll get a nice thrashing....it's MY turn to use the whip!" Sometimes after th...

Meghan's Revenge Pt. 02

by AnonymousHoppingBunny on Apr 28, 2020
BDSM

Mike had felt nothing but anger toward Meghan after being left handcuffed to the chair, denied, and in chastity. It had taken him hours of struggling to free himself from the chair and finally negotiate the key from the melting puddle of ice. Yet in addition to his murderous anger and desire to get back at Meghan, his sexual denial had left him with her body...

Prescription Cuckold

by cuckytoher on Jul 11, 2018
Fetish

My wife Stephanie and her boss Frank's affair was now out in the open. Frank is a doctor and my wife runs the office for him. I work for her father in his janitorial service. As I wrote in a previous story, I was out of town while Frank and Stephanie made their affair known to me. They let me know I was to be their cuckold upon returning. I was heartbroken b...

My Journey to Becoming a Mistress Ch. 02

by intofdom on Sep 17, 2017
BDSM

On the second anniversary of the day we met. He asked me for a large sum of money since I manage his dollars now. He told me it was a secret and I would definitely be surprised. I impatiently waited till that night. He arrived with a big bag. He sat next to me in bed and pulled out sluttiest dress that I had ever seen. He requested me to wear it. It was so...

Simon's Sluts

by Ellyce on Sep 16, 2017
Transsexuals & Crossdressers

Chapter One – Wake Up Call The alarm went off and I groped for the "snooze" switch out of habit. Then I remembered that I had day maid duty today and sleepily rolled out of bed. Wandering into the bathroom, I pulled the shortie nightgown over my head and observed myself in the full-length mirror starting at my red-painted toenails. My gaze wandered up my sh...

Simon’s Sluts

by Ellyce on Sep 16, 2017
Transsexuals & Crossdressers

Chapter One – Wake Up Call The alarm went off and I groped for the "snooze" switch out of habit. Then I remembered that I had day maid duty today and sleepily rolled out of bed. Wandering into the bathroom, I pulled the shortie nightgown over my head and observed myself in the full-length mirror starting at my red-painted toenails. My gaze wandered up my sh...

Watch the Receptionist

by justincbenedict on Oct 7, 2019
BDSM

When Aram got back from lunch, he saw Holt, his new assistant, sitting in his chair, her long legs crossed, and she did look smashing in her cream muslin dress. Really, it was a bit beyond the office code, as the dress was more of a mini-dress thing, and just ended past Holt's thighs. But Aram enjoyed looking at Holt as did other men (and some women)in the...

Duncan Gets Engaged

by justincbenedict on Sep 12, 2018
BDSM

Duncan Lipscomb looked at Wren Johnson sadly. He really wanted her to marry him one day, but he kept pissing her off. And she looked very annoyed now. Wren was reclining on the bed, gazing fixedly at her Ipad. "Wren, please." Duncan begged. Wren looked over at Duncan, cocking her head. God she looked so cute in that body stocking. It was worth every penny...

My Birthday

by hemlocks on Sep 14, 2017
BDSM

I knew David and Cindy would be home in half an hour. Cindy is my wife. David is her favorite lover. We live with him. Cindy and I have been married for 10 years. For the past 2 years, we have had a new arrangement. I began to have problems pleasing Cindy in bed, and it led to fights. We talked about it a lot, over several weeks. We talked about the source...