Sydney

By Anon

The story you are about to read is 100% true. The names have been changed to protect the guilty.

I’ve long loved women with short hair, dating all the way back to my high school days. As the years went by, my own hair started to thin on top, so I had my head shaved by my barberette one day and kept it ever since. One day a few years ago, I spotted a gorgeous middle-aged bald woman at a local fast food restaurant and have thought about her ever since. But how could I meet such a woman? Believe it or not, I decided to try Craigslist. I didn’t expect anything, but amongst all the spam replies one email stood out; a lady in her mid-thirties claimed she had shaved her head and kept it for a while, but now wore it short. We traded a few emails and I asked if she would ever consider shaving again for the right person. She replied with an enthusiastic “yes!” and I knew then I had to meet this woman.

We arranged to meet in a public place with lots of people around. She was pretty and friendly with big hazel eyes and a nice smile. Some might have said she carried a few extra pounds, but I’ve never been hung up on that. “I’m Sydney,” she said. “Happy to meet you. I’m David.” We sat and talked for a good hour, swapped phone numbers, and left.

Over the course of the next several weeks, we texted, met for lunch frequently, and went on dates. Then one Friday night, she came to my house. We walked around my quaint bayside town, listened to some live music, talked and laughed. We made our way back to my place, were we sat on the couch, exchanged a kiss, and we sat there with her head on my shoulder.
“What time is it?” she asked. “About 9:30” I replied. She sighed and said “You know what I wish?”
“What’s that?”
“I wish there was a barbershop open right now.”
Well, that got my attention in a hurry. I slyly asked “Am I that shaggy?” know full well I had shaved my head before going out this night.
“For me, silly,” she said.
“What do you want to have done?” I asked.
Running her hands through her brown crop, she said “I want all of my hair cut off.”
As my heart beat faster, I said “Well I can do that here, if you really want it.”
She raised her head. “Really?! Would you?”
“Only if it’s totally your choice”
“It is!”
Wasting no time, I moved a chair into my master bath. I opened the closet door to retrieve my clippers and cape. Sydney eagerly sat down and I fastened the cloth cape around her neck, all while getting harder by the second.
“Want me to leave a little the first time or get you ready for the razor?”
“I want to be shaved bald just like you!”
After firing up my hot lather machine, I turned on the clippers with no guard attached and surprisingly, took my time. I took the back off first, then went up the sides, then front to back on the top. My heart was racing. I wiped off her stubble and reached down and kissed her.
“Ready to be shaved?”
She moaned “YES, YES!”
I wet a warm towel and wrapped it gently around her hear, leaving it for a moment to soften up what hair she had left. I took some sunflower oil and rubbed it into her head, the applied the hot lather. Sydney let out another moan.
I put a fresh blade in my Mach3 and got to work, going gently again the grain. I oiled and lathered her up again and went with the grain this time, checking for spots I missed. Soon I was done, I removed the cape and almost came in my pants. She stood up and we kissed.
“I’m so horny!” she exclaimed. Let’s go!”
We stripped quickly and climbed into bed. We kissed again on the lips and I began kissing her uncontrollably on her beautiful bald head. She reached down and felt how hard I was.
“Fuck me! Fuck me hard!”
We began making love and we both squealed in delight. I was almost worn out when she grabbed me and screamed “I’m coming!” We climaxed at just about the same time and laughed and moaned.
We laid in the bed for about 45 minutes without showering, only getting water from the refrigerator. We cuddled and I kissed her head frequently.
After a rest, she looked up at me.
“Again?” she said slyly.
“I pretty sure I can.”
“You have a condom, and some lube?”
“Sure. Why?”
“I want to get butt-fucked. Hard!”
I leaned over and kissed her bald head for the umpteenth time. “Anything for you,” I whispered.
I walked into the bathroom to get a hand towel, then opened my nightstand drawer to retrieve a condom and the lube she requested. Sydney got on all fours while I got prepared. I caressed her body slowly then liberally applied the lube on her and me.
I said gently “Let me know of if it hurts and I’ll stop. She nodded without saying a word and I gently inserted my penis into her butt. She let out a groan and I slide right in.
She let out a passionate moan. “Just like that! Fuck me hard!” It didn’t last as long as I wanted, and in about 2 minutes we both climaxed, her with more moans and squeals.
I cleaned up and we showed together, shampooing each other’s shaved heads. As we stood in the shower with water pouring over us, we kissed and hugged and exchanged “I love you’s.”
Epilogue: About a week after this magical evening, Sydney moved in with me, where we remain today. We stay busy with work, but nearly every weekend we shave each other’s heads and enjoy amazing lovemaking. She seldom wears wigs or hats and we frequently walk around town holding hands with our baldness on full display. We get a surprising number of smiles and compliments. I can’t help but feel that if others knew our secret, nearly everyone in town would be shaved like us.

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