My Charity Headshave (And Its Aftermath)

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I work for a small but well-known tech company in the Bay Area. My boss, its founder, is an absolute genius. Deserves the many words in his TED Talk bio. That’s why I went to go work for him. As a programmer, I could work anywhere that I wanted, but I chose to work for him because I wanted to learn from him. And, yes, I have learned from him over the years…. and his beautiful wife.

During my first year there, his wife came to visit him at the office, and that’s when I met her for the first time. She didn’t do that often due to her own successful business, a chain of salons. They were upscale places for rich people. I Googled them after I met her. I personally would never go there, I thought, wondering if she still cut hair in one of them and which one.

After they had lunch, they went over to my work station. Immersed in my coding, and wearing headphones, I didn’t notice the 6ft tall blonde woman playing with my mousy brown shoulder length hair until she gave it a sharp tug. I slid off my headphones, enchanted by the glamorous woman standing before me. After she introduced herself, she told me about their annual cancer fundraiser.

“It’s no pressure,” she said, “We just ask people to either donate money or shave their heads. Mostly donate money. Though I would love if you volunteered to shave off that mousy hair. I think that being bald would suit you better.”

“I would shave my head for you,” I blurted out.

(I wasn’t immediately submitting to her. I actually had always wanted to shave my head. It was a longtime fantasy. I did love that she handed me the opportunity to do so.)

She smiled. Then she gave me the details. It was in a week. After she left, my boss put his hand on my back and thanked me for saying yes so eagerly to helping their favorite cause. His tone was professional, but his hand was lingering longer than it should have and sliding down into the small of my back, a danger zone, which made me blush.

My boyfriend was furious about my decision. My long hair was the only traditionally feminine thing about me. He refused to go to the fundraiser with me. In hindsight, it was probably a blessing that he didn’t go. My boss’s wife immediately took me aside the moment that I walked through the door, wearing just my regular jeans and a t-shirt. She brought me to a little room where I changed into a little blue sundress that she brought for me. Her eyes never left me as I changed. Especially my freshly waxed pussy. She also insisted on doing my makeup.

Surveying her finished product, she said, “Just one thing left to make you perfect.”

Then she brought me on stage. My legs felt like jelly as she sat me down and caped me. Kissing me on the cheek, she said that she was happy that she would be the one to shave me. When she turned on her clippers and plunged them into my scalp, I went a little deaf. I could only see the strands of brown hair raining down around me. And feel how wet it was starting to become between my legs… I had to bite my lip to keep myself from moaning. During my shearing, she started handling me rougher and rougher. Even pinching my nipple through the cape at one point. She knew that I was turned on. Standing nearby and watching closely, he did too.

When it was over, she pulled off my cape. Then she pointed to a nearby broom. With much difficulty, due to the knotted up arousal of my body, I took the broom and swept up my fallen hair. To be frank, I was disappointed to just get a buzzcut. I spent the rest of the party feeling my stubby hair and wondering what it would be like to be shaved completely smooth. I didn’t dare ask though.

My boyfriend HATED my buzzcut instantly. He, however, liked the new dress that I came home in. To please who I thought was him, I started adapting a more feminine style. The next time that I saw my boss’s wife, about two months later, I was wearing a red wrap dress and light makeup. My hair have grown out to a soft two inch pelt. I blushed as she started to lavish praise on me.

“She looks great,” she cooed to her husband, “but her hair could use a touch up.”

“Yes, my thoughts exactly, maybe shave her down to the skin this time. Come to our house tonight at 6pm for dinner and a little touch-up,” he said.

I couldn’t say no to them. So, I arrived at their house promptly at 6pm. They lived in an expensive mansion by the sea, which, I noted nervously, didn’t have many escape routes. I still went in AND lied to my boyfriend about my whereabouts.

My boss and his wife greeted me warmly. Then they asked for my clothing. Feeling like I was in a dream, I handed it over, no questions asked. Once I was nude, he slipped a leash around my neck. She gently pushed me to my knees. I crawled into their dining room where a lavish meal waited. They had dinner, talking about their days and feeding me tibits from their plates like a beloved pet. I didn’t dare speak.

When they finished with dinner, they brought me to their dungeon. There was a barber’s chair right in the center of it with a tremendous dildo in its seat. They eased me into the chair, sliding the dildo in my asshole. Then they strapped me in. As he watched, she shaved me to the skin, giving me the hot lather experience that I was so curious about.

Raking her nails down my bald head, she told me, “You’re breaking up with that boyfriend tonight. We are putting you to work first.”

Tears in my eyes from the intensity of my arousal, I nodded.

I’ve been with them for years. They take very good care of me. It’s an open secret that I’m their personal bald submissive. Most people, however, shrug it off. It is the Bay Area.

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