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A Day at the Beach Turns Girly

Worst Day to Best Day Part 1

By Derick SinclarPublished about a year ago 8 min read

A Day at the Beach Crosses Turns Girly

Derick Sinclair

An amazing beach day in San Diego. Simon fills up his scooter and heads out to enjoy the clear sky, no wind, and 85 wonderful degrees. Destination, Black’s Beach. Known to locals for its liberal clothing policy. The drive along Rosecrans is hectic. The bumper-to-bumper traffic is back toward the base.

Not to worry, the lane-splitting laws in California are a bit vague for two-wheeled vehicles. There were several in front of Simon who rolled past him between the lanes. Simon has a low threshold for waiting so he jumps into traffic evasive mode and heads carefully down the center of traffic. With any luck, he should be able to cut across toward La Jolla shortly and the traffic will be a memory.

The salt air, warmed by the sun, is nearly perfect. Driving a scooter to the beach is so freeing that Simon is singing along with his playlist. Through the side streets and up to La Jolla Blvd he is cruising. The traffic is jammed up so lane splitting it is. Zoom goes his internal soundtrack. Zoom, whoosh, whoosh, whoosh as he zips by the cars. He is nearly there. The sign for the college is right ahead and he has one turn before he is on the road to the beach.

The hike down to the beach is filled with sandy, slippery, and steep spots that can take your breath away when you start to slide. Forever under change, each time the trail is used, it shifts a little from the day before. Fortunately, yesterday it rained, and the sandstone and dust mix are firm today.

At the bottom of the trail, there is a draw up toward the cliffs that is a popular get-together spot for those looking for a hookup or something pharmaceutical. Toward the beach, there is a sign alerting that there might be less than clothed people and that it is illegal. It’s always illegal, but the enforcement starts at the sign and heads north.

Simon sees a perfect spot near the bottom of the cliffs below the Torrey Pines Golf Course and makes his way toward the spot he sees. Once he is there, he is alone, which was his goal for today. Lay in the sun get rid of the tan lines and enjoy the beach. Nothing else.

That plan was perfect for about an hour. He stretched out his beach mat to stake out his base camp. His towel was near his head as a pillow. Once undressed he applied some sunscreen and settled into the ohm of the beach. Looking around to see if anyone was likely to disturb him, he felt secure and relaxed. His playlist switched from driving mode to chill at the beach mode, and he fell asleep.

Suddenly, hearing sounds that weren’t on his playlist, he awoke to see two people standing near him. Given that the beach was nearly deserted in this area it was a bit odd.

“Oh hey, sorry to barge in but we usually set up camp in this area and wanted to stop and say hello. I’m Chris and this is my wife, Danelle. Do you mind if we share this area with you,” she said.

“No, I don’t mind. Is it OK that I am undressed?”

“Of course, wouldn’t have it any other way,” said Danelle.

Danelle is a soccer mom looking blonde, mid 30’s, fit and well-tanned. Chris looks like an office-based worker as his tan is not as dark. His clothes look to be designer and are more preppy than a beach bum. Danelle looks to be at home on the beach and is the first to disrobe. She shares her well-tanned body from the back without reservation. Enjoying the show, Simon feels the need to say something and asks if they get to the beach often.

“Yes, I like this spot so much, I am here a couple of times a week. It is outside of the flow of people, and I haven’t had anything stolen from me. I bought this cooler, and we put a dog leash screw in the middle and a lock. Haven’t had anything lost since,” said Danelle.

“I get to come on some weekends and days like this that happened to work out,” said Chris.

“This is my first time here. Honestly, I am a bit worried that I will offend someone or do something that will end up getting me in trouble,” said Simon.

“Don’t worry about that. Enjoy the beautiful weather and have fun. For the record, I don’t mind you looking at me,” said Danelle.

His lucky day thought Simon. Beautiful day, beautiful people. Life is grand. And it would have been a story to tell had two things not happened while he was enjoying a Frisbee game. When they came back, Simon’s clothes were gone. This included his cell phone and his keys to the scooter. Now is the time to freak out, he thought. What am I going to do? How will I get home? All these thoughts were running through his head.

“Simon don’t worry you can come with us we will sort it out at our home. We live on the other side of the highway and can get you there and sort things out,” said Danelle.

“Thank you so much. But what do I wear from here to there? I don’t have anything, and my towel is even gone,” he said in a clear panic.

“You can wear my skirt and blouse. Here let me see what else I have. A hat, and flip-flops,”

“A skirt, I don’t know. That seems…,”

“It’s either a skirt and blouse or my bikini. Chris’s clothes wouldn’t fit you at all,”

Ok, I think I have a spare key at home. Oh no. I don’t have a spare key outside of my apartment. This is getting better by the minute,”

“Calm down, go back to chill, everything will work out. Let’s enjoy another half hour of sun then we can go,” said Chris.

“It is what it is. Thank you for the offer to help me. I guess having you here today was preplanned by the universe. Thank you,”

“Maybe, let’s see what happens next,” said Danelle.

They chilled for half an hour. Emotions had settled down and now what was seen as a disaster is now an adventure. They talked about the reality of wearing women’s clothes and how it isn’t as weird as it is said to be. Going naked to the car would not be an option. Police would surely be notified and waiting for him in the parking lot.

“OK before we head back let me look at you. Your hair is long enough to hang out below the hat. I think that we can pull this off without any fanfare. Here are some sunglasses to complete the outfit,” she said.

Simon is now ready to go. He has a floppy hat, a blouse that is perfect for his frame, and a skirt that is mid-calf in length, flip-flops complete the look. For anyone who sees him, he would look like any of the people climbing back up the hill to their cars. Once at the top, they check the scooter to see if anything is unlocked that would hold a key or other essentials. Nothing. The cable lock is wrapped around a solid railing and should be good until they get back.

“Thank you both for helping me. Even in a skirt, I am more thankful than you can imagine. I like the feel of the skirt and the blouse feels so good against my skin,”

“Do you want to keep the outfit? I am sure we can spare it. By the way, you look so good I would be very interested in you if I saw you across the parking lot,” said Chris.

“I would never have guessed that I looked anything but weird,”

“No, this outfit is so you. It makes you look like a stylish woman going about her day at the beach,” said Danelle.

They took off toward their house to be able to grab some food and then resolve the issue at hand. When they got to the house all the calls that needed to be made were at the voicemail level and needed to have a return call. The key to the apartment was a priority to be able to get the spare scooter key and clothes. The landlord may be closed for the day and would rely on the usually stoned on-call guy.

“I need to go to the store. Simon, would you like to come with me as you are?” said Danelle.

“Um, well, OK where are we going?”

“I need to go to Walmart. They are up the way a little bit and we can find you something to wear there if you want,”

“Danelle, can I be honest with you about the clothes? I don’t want to change into something else. I love the look and the feel is spectacular,”

“Am the lucky one to have dinner with two gorgeous women tonight,” said Chris.

“If Simon stays in the clothes he has on,”

The two head off to the store and return with several bags of food and some clothes.

“So, you decided not to stay dressed up, Simon,” said Chris with a tone of disappointment.

“Honey, even better than that. We have several outfits, panties, a bra, and he looks great in all of it,”

“What, you have gone to my side of the hill,”

“I didn’t tell him yet. But since the cat is out of the bag,”

“Simon, I have been wearing women’s clothes for years. I prefer to look at them this way, once I buy them, they are my clothes. My clothes are mostly feminine in presentation. I don’t call it crossdressing I prefer to call it me dressing the way I want,” said Chris.

“I am a deer in the headlights on this. I know that I have never felt this happy with clothes before and even from Walmart. By the way, don’t worry, I will pay you back as soon as I can get into my apartment,”

“Hey, let’s see what you have and maybe a fashion show,” said Chris.

Simon put his bag down and spread out the clothes. Since they had been without clothes for most of the day, he felt no need for false modesty and tried on the bra first. A T-Shirt Bra size 38 A in pink. A perfect fit. Next were the panties. He opened a package of basic nylon bikinis in a floral pattern and selected the pair with the boldest pink color and flowers. Next, he put on an A shape, tan, slightly above the knee-length skirt. The blouse is light tan cotton in a gauzy weave. The whole outfit looked like it was made for him.

“Simon, or should I call you Simone? You look like you should be walking around Paris looking for designer clothes. I have never seen anyone take to dressing as you do,”

“Simone, you know, I think that will work,” said Simon, now Simone for the first time.

Simon tried on the rest of the haul. I found his favorite and wore it to dinner at a little restaurant near their house.

“Simon, it looks like you are going to be staying with us for the night. We have the room and would love you to stay,”

“I am sorry to put you out. But yes, I would love to stay,”

Tomorrow is the real test – daylight. Will Simone show up or will Simon? Stay tuned to find out what adventure Chris and Simone get into.


About the Creator

Derick Sinclar

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  • DigiUpdatehub11 months ago

    Torrey Pines Golf Course

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