The Vacation

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I had always dreamed about going to the Caribbean and this year, those dreams became a reality. Even holding my ticket at the airport with my best friend Susan, it was hard to believe this was actually happening. At 45 years old, I still was able to maintain my beach body with frequent trips to the gym for Zumba and spin classes. I kept my mid-back brown hair pulled into my standard “travel ponytail”. Susan was a few years older than I was, but looked about 10 years younger with her perky breasts and bottled blonde hair cut into a chin length bob.

“Imagine this Cheryl.” Susan said with a smile as we made our way through TSA. “In 4 short hours, we’ll be sipping drinks on the beach.”

“I’m just hoping I can snag a twenty something with a chiseled chest to be my island fling.” I responded back, flashing her a smile in return. “This gal needs a little action along with sipping drinks on the beach.”

Although I was half joking at the prospect of hooking up with an islander or fellow tourist, the truth of the matter was that I really did need some romance in my life. I wouldn’t have been so desperate if Robert and I hadn’t broken up 2 months ago, landing me in somewhat of a slump.

Susan had the opposite problem. It seemed that she floated from one relationship to another casually, only sticking around long enough for a few monumental orgasms before moving on to greener pastures.

The flight was uneventful, so I spent much of it sleeping to ignore the horrors of flying coach class.

We landed in St. Thomas and stretched our legs after emerging from the plane.

“Warm sands await!” Susan said as she ushered me through the airport. “Lets get to the hotel and soak all of this in. I want to do everything.”

After checking in at the front desk, Susan and I dropped off our bags and decided to walk around the hotel pool to investigate our surroundings. As we circled the pool, we noticed 3 little black girls braiding the hair of a guest sitting in a lounge chair. The guest looked like she was in absolute heaven as the 3 girls worked their way through her hair making tight braids. The most striking thing about the whole situation was that the three little girls were completely bald.

“I want us to get that done too!” Susan said pointing to the woman in the chair. “She’s embracing the culture and making the most of her trip.”

“I don’t know Susan.” I said with my eyes fixed on the little girls. “I don’t think I’d look good in braids.”

“It’s not about how it looks.” Susan said, playfully nudging me. “It’s about experiencing something new.”

“Maybe.” I responded as we continued our walk.

We made our way down to the beach and walked the shoreline until the sun began to set. We walked back to the pool area as we planned for dinner when the 3 little bald girls approached us.

“We saw you admiring our work earlier. Would you like us to do your hair too?” The older of them asked with a big smile. “Only $25 for each.”

“Yes.” Susan said before I could say no. “Just like the other woman. For both of us.”

“Just like the lady from earlier?” The little girl asked.

“Yes.” Susan said as she put her arm around me. “Me and my friend Cheryl really want to have the same treatment.”

Susan handed the girls $50 and they got right to work on our braids. The older one that took the money worked on Susan while the other two worked on me. Their little fingers worked fast and made tight braids. As they continued to work, my discomfort increased. I felt as if my whole face was being pulled back as a result of their braids. Before long, they finished their work and produced a small mirror to inspect.

“What do you think ma’am?” The little girl asked while holding the mirror. 

“We love it.” Susan said grimacing with what I assume the same pain I was experiencing. “You are very talented.”

“They are a little tight.” I said touching the braids. “But they are pretty.”

“We’re sorry.” The little girls giggled in unison. “New braids are only uncomfortable for a little while until you get used to them. We can make it less painful if you’d like.”

“Yes please.” I asked before Susan could make up some pleasantry.

The oldest girl produced a bottle of liquid and began spraying our scalps. As the liquid made contact, I immediately felt a cooling sensation, and the discomfort lessened. 

“Does that feel better?” She asked with a smile

“Yes it does!” I said touching my braids again. “What was that?”

“Secret recipe.” The girl giggled. “Fruit juices mainly.”

“Well thank you three so much.” Susan said handing them another $50. “This is a tip for being so sweet. By the way, you look beautiful bald.”

“Thank you ma’am.” The little girl replied. “We get many compliments on our sweet bald heads.”

The other two girls said something in another language and started giggling again. We stood there awkwardly, clearly not getting the joke before they made their exit, looking for more tourists to braid.

“Well that was exciting.” I said touching my braids again. “I’m not necessarily liking this.”

“Oh come on sour puss!” Susan said striking a pose. “If you still hate it tomorrow I’ll help you undo the braids.”

We both retired to the room and threw on some floral dresses before heading down to the restaurant. We were definitely turning heads as the hostess ushered us to our table. It was hard to not notices people around the restaurant stealing glances at us. All of my feelings of self doubt went out the window when our Waitress came to us. She was absolutely stunning with her mocha colored skin, but her most prominent feature was her completely hairless head.

“Welcome to the Cove. My name is Tanya and I will be serving you today.” She said with a smile. “I love your hair by the way!”

“I love yours!” Susan said, clearly embracing an awkward conversation about hair with someone who clearly doesn’t have any. “You look gorgeous.”

“Thank you.” Tanya said running her hand over her head. “It was a big change, but I love it.”

Tanya pulled our her phone and showed us what her hair had looked like just a week ago. She had braids that reached her mid back.

“Wow, that’s some change!” I commented as I continued to stare at her perfectly bald head. “What made you decide on shaving your head?”

“My hair dresser suggested it.” Tanya explained. “I had braids for so long, and I really wanted a change. She encouraged me to let it all go and embrace a smooth, shiny, bald head. I’ll never go back.”

With that Tanya took our order and disappeared into the kitchen.

“She’s beautiful.” Susan said sipping her glass of water. 

“Yeah.” I replied. “Bald definitely seems like a popular hairstyle down here.”

“I think I could pull it off.” Susan said with a smirk.

“Okay, sure.” I said sarcastically back at her. “I think that’s one local custom you probably won’t partake in before we leave.”

Much of the dinner was filled with reminiscing each other with stories from our past, but every time Tanya came to our table, we both caught each other admiring her looks. After we settled up the bill, I noticed a business card was slipped behind my receipt. 

“What is that?” Susan asked

“It’s a business card.” I replied as I scanned the card. “It says ‘Island hair transformations’ and has a note written on the back that says ‘for when you want to get rid of those braids like me ;)’.”

“She must have caught us staring.” Susan said with a chuckle. 

“Oh come on, we were basically gawking at her all night.” I laughed back. “We probably made her feel uncomfortable.”

“So are we going to pay that salon visit tomorrow?” Susan asked snatching the card from my hands. “You did say you weren’t happy with the braids.”

“I’m thinking more that I’ll have you undo them tomorrow.” I smiled at her. “I don’t think I’m ready to shave my head on a whim.”

“Could be fun though.” Susan smirked. “I still think I’d look good.”

We laughed about it all the way back to our room where we planned our the following day. 

“Are you going to bed?” Susan asked.

“Yeah, I’m wore out from today.” I replied as I made my way to the bathroom. “Why?”

“No reason.” Susan responded as she grabbed her phone. “I’m going to explore a little.”

“At this time of night?” I replied with concern. “Let’s wait until morning and I’ll go with you.”

“I’ll be fine girl.” Susan said looking at her phone. “You get some sleep.”

We said our goodbyes and Susan exited the room. I got myself ready for bed and drifted off to sleep a moment later. It was one of the best night sleeps I had ever had

“Cheryl.” I heard a voice call out to me. “Wake up honey.”

I slowly opened my eyes to see Susan hovering over me. She had a beautiful, floral, silk bandana covering her head and was dressed in a simple white sun dress, clearly ready for the day.

“What time is it?” I asked shaking the sleep from my head.

“8.” She replied back with a smile. “Time to get up and get ready for the day.”

“I like your bandanna.” I said as I dragged myself out of bed. “Where did you get it?”

“Tanya gave it to me.” She smiled back.

“The waitress?” I asked in disbelief.

“Yeah she took me out on the town last night after her shift.” She continued to beam. “We had fun.”

“You sly dog!” I replied. “I never knew you to swing that way.”

“Oh come on Cheryl.” Susan winked at me. “You only live once.”

“Well okay then.” I said as I shuffled to the kitchen searching for coffee. “I’m just surprised. That’s all. I’m glad you had fun though”

“Speaking of surprise.” Susan said as she followed behind me. “Promise to not freak out.”

Susan didn’t give me a chance to respond before she slid the silk bandanna off to reveal her perfectly smooth scalp. She stood there sheepishly waiting for me to respond.

“Holy shit Susan!” I finally gathered my thoughts. “You’re bald!”


“Like, bald, bald!” I continued. “I thought we were just joking last night!”

“I was curious and she encouraged me.” Susan replied looking a little defeated. “Does it look bad?”

“Of course not!” I replied. “But wow, I was not expecting that this morning. Jesus, let a woman get her coffee before you spring something like that on her.”

“I’m sorry.” Susan chuckled. “Do you want to feel it?”

As if in a trance I walked up to my friend and placed both of my hands on her scalp. It felt some unbelievably smooth. It felt perfect.

“You really like it?” Susan asked as I continued to caress her head.

“It feels good.” I replied. “How do you feel though?”

“I feel fantastic to be honest!” Susan said. “Definitely keeping it like this for a long while.”

“Seriously?” I asked, touching my braids.

“Yeah.” Susan smiled back. “And if you are interested you can have this too.”

“Like bald?”

“Yeah.” Susan said guiding my hand back to her head. “I think deep down you want have a nice, smooth, slick, bald head.”

“I don’t know.” I said biting my lip in indecision. “Thats a big change.”

“Come on girl.” Susan smiled back. “You only live once.”

After a quick cup of coffee and a muffin, I found myself being dragged into the cute salon from Tanya’s business card. Susan had covered her scalp with her silk bandanna again, but she was clearly remembered by the owner.

“Ah, has my vanilla beauty brought me another customer?” I heard a sultry voice call out.

I turned to see an older black woman, also with a bald head standing behind me.

“This is the friend I told you about.” Susan said. “She wanted to get rid of her braids too.”

“Is that true sweetie?” She asked me. “Do you want me to get rid of those ratty braids?”

I only nodded as I was ushered to an awaiting chair.

“I’m going to take good care of you.” She said as she draped me with a fresh cape. “But I’m going to assume you want the same treatment as your friend. Smooth, unless you object.”

I didn’t object as I heard the sound of clippers come to life from behind me. I watched in the mirror as this nameless bald woman placed the guard less clippers to my forehead and slowly drag them into my hairline. The whir of the clippers changed drastically as they met the tight braids, but they were not stopped. She moved slowly, severing each braid close to my scalp. As she worked, more and more pale skin emerged. Before long, the last of the braids hit the floor and the clippers were turned off. The owner placed her hands on my shorn, foreign scalp.

“I can make you smooth.” She said as she ran her hands over the raspy stubble that used to be my hair. “So smooth that you wouldn’t believe, but I need you to tell me that it’s what you want.”

“Perfectly smooth.” She continue. “No one would ever be able to tell that you ever had hair before. Smooth.”

“Will it grow back?” I asked.

“If I do it right, it won’t.” She replied as she busied herself with something on her counter

I continued to stare at myself in the mirror as she began to smear a purple cream over what remained of my hair. After a moment, I began to feel a strong tingling sensation all over my scalp. The intensity of the tingling increase each second that the purple concoction was on my head until suddenly it stopped. Clearly reading the expression on my face, she could tell that her cream had done its job. She took what looked like a plastic scraper that was contoured to work on heads and began scraping away the purple cream. To my surprise, all that was left in the wake of the scraper was perfectly hairless skin. Before long, the owner set the scraper and the bowel full of cream and hair down on the counter. She then toweled off my head and applied a sweet smelling oil to my scalp. I felt like I was in heaven.

“I pronounce your bald.” The owner said kissing my hairless scalp. “Welcome to St. Thomas.”

“Thank you.” I said as I admired the alien reflection of myself caressing my head. 

Susan handed me a similar bandanna to her own and helped me slip it over my virgin scalp to help protect it from the sun.

”Now are you ready to have some fun?” Susan asked in a whisper as she adjusted the bandanna on my head. “Because this is going to be a vacation you won’t soon forget.”

-To Be Continued

4 responses to “The Vacation

  1. The story is great, a thoroughly enjoyable read. Though, if I may offer a bit of a critique, the ending feels a bit rushed (which is totally understandable, given the fact you wrote it as a quick story written during a trip). However, the ending, final paragraph really, could be reworked and extended to improve pacing or even made into segue into possible part II.

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