A Staycation Contest Entry

Max Williams smiled when he saw it was his mom calling. It was always great to talk to her. Since she remarried, she’d never been happier.

“Hey, mom. What’s up?”

“Hi, sweetie. How are you doing?”

“I’m great. When are you coming up to visit again?”

“Honey, Henry and I are passing thru in the night. We’re headed up to New York City for the Spring and then we’re flying over to Greece for a cruise. I was hoping you’d do me a favor.”

“Sure. Just say the word.”

“Would you come to watch the house, babysit the cats, and water my plants? Of course, you can use our credit cards, too. I figure since we’re getting a vacation you can have an all expenses paid ‘staycation’ at our new place.”

While it wasn’t the home he’d grown up in, it was in the same town where he’d gone to the local public high school. Back then, Max and his mom lived in an apartment complex. When she got married, she moved in with Henry.

“Sure. Sounds like fun. Do you have a room for me or will I crash on the couch?”

He heard his mom laugh. “No, silly. You have your own suite above Henry’s garage. I just finished decorating it for you. Just for you, sweetie.”

“Thanks, mom. I owe you so much already. Someday, I’m going to pay you back for all of this.”


“Yes, mom.”

“Please don’t be mad, but I went and bought you some outfits. You know, just leisure wear. I think they call it active wear and I bought you some bathing suits, too. I got a bunch of sizes. I had to guess.”


“No, Max You’re getting new ID coming in the mail, and you need to start living life as your real self instead of postponing it.”

“Mom, I want it so bad, but you know how frightened I am.”

"What does Dr. Mitchell say about it?"

"She says I need to grow some balls and act like a woman."

“She's right, but I understand, Max. I’m not pushing you. You can be a woman for a month down here in Naples. It will be like practice.”

“I hear you.”

“Well, it’s what I want for you. It’s not like we haven’t been dancing around this since you were five.”

Max had tears in his eyes. He was speechless. “I love you, mom.”

“I love you, too. Max. Now just say okay and let me have my way.”

“Thanks, mom.”

“I’ll miss you, honey. But promise me something.”

“Of course, mom.”

“Send me a pic of you in the orange bikini.”


“Bye, Maxie”

Of course, Max said yes. In his mind, the timing was perfect. He’d just wrapped up his freshman year at the University of Florida, Gainesville and had gotten a notice that his dorm suite needed to be vacated by the end of the month. He had planned to find a job so he could afford his own place, but saving a month’s rent while living his at mom and stepdad’s place would be great, too.

His mom had met Henry when Max was in high school. They’d dated for a while before they married. Max liked Henry.

Henry was wealthy. Just about the time Max was headed out to start college, his mom gave up their apartment and moved into Henry’s amazing house on a golf course in a gated community. The ten thousand square foot house sat on five acres.

Henry offered to adopt Max when he married Anne. Henry didn’t have any children and liked the idea of having a son. Max didn’t have the heart to tell him that he wouldn’t be a son for much longer.

Money wasn’t Max’s priority. His goal was to be happy. When he graduated high school, Max knew exactly what he wanted.

Before Max started college, he and his mom slipped away and went to Chicago. They had arranged for him to have facial reconstruction surgery which his mom paid for. She was by his side the whole time.

Max had shared his gender dysphoria when he was five years old. Anne had been his biggest supporter ever since.

He was majoring in the sciences at Gainesville. He wanted to go to medical school and eventually become a psychiatrist. That was his dream. He was familiar with the career since he’d been seeing one doctor after another since he was seven. Max saw lots of doctors and liked them all.

So Max packed his apartment up and loaded it in his old Honda. He talked with his mom daily. They were both sorry they were going to miss him and promised to catch up when they returned.

His mom was always full of enthusiasm. “You know, you could fly over to Europe this summer and meet us somewhere. Would you like that?”

“Sure, mom. Let’s talk about that when you finish up with the cruise.”

“Your step-father wants to see Spain. How’s that sound to you?”

“Sounds great!” Max laughed. “But, I won’t be able to apply for a passport until all the paperwork is in my hands. Max was looking forward to having the F for female on his identification.”

“Oh, I’d forgotten about that. Okay. Well, it might work out. If not, maybe we’ll do Europe together next summer.”

Max drove down to Naples and showed his pass at the gate. The guard checked his name off on the clipboard. “Good afternoon, Max. I have an envelope for you in the office. Would you mind pulling over up there under the shade trees?”

Max sat in the Honda waiting. The music playing softly on the stereo and the air conditioner was humming. He was a bit overheated wearing a shirt and tie. The guard was his last stop before his staycation began.

“Here you are, Max. Welcome to The Ridge. Your mom said she enclosed keys and all the info about the pets and plants. Have a good month.”

Max handed the man a ten dollar bill and thanked him. He put the car in gear and drove the familiar route to his mom's new home. He shook the garage door activator out of the envelope and used it to go straight up into the garage shutting the door behind him. He noted that Henry had continued to expand his collection and had added lifts to three of the bays enabling him to fit twice as many autos as before. Henry collected muscle cars from the 60’s and early 70’s.

Max grabbed his bags from the trunk and used the keys to open the door. As he walked through the house, he noted some things had changed.

He wasn’t really surprised that his mother had the room redone for him. She couldn’t resist. She did leave him with neutral color walls, but some of the touches were more feminine than he expected. But, mom had been in on everything he’d been going through since day one. Max assumed she wanted him to have a woman’s room to live in.

But, they’d both agreed to break it to his Henry gently. Max wondered whether he’d want to adopt a trans-daughter. Well, only time would tell.

Max stripped off his clothes and hung them up. He hoped he didn’t need the dress shirt, blazer, and khakis during his month here. Actually, he hoped he’d never need them again.

School had been great but living with three other guys as his suitemates made his comings and goings difficult to hide his changing body. He became a master at camouflage.

All that would change when he came back in August. Hopefully, he’d have his own place and could evolve into the woman he had wanted to be all his life at his own pace.

In the fall, he’d be breaking the news about his transition to everyone he knew. He was extremely anxious about that.

Max unpacked his clothes and then started looking over the stuff his mom had bought for him. When he picked up the orange bathing suit, his blood started pumping. It was perfect. It was fairly demure and modest. While it showed a lot of flesh, he really liked the cut and the material. He looked at himself in the mirror as he released his hair tie. He shook out his thick, shoulder-length wavy brown hair he walked in circles in front of the mirror. He vamped a little.

He felt a surge of happiness flow through his body. He’d made so much progress since turning eighteen. His doctor said taking a weekly hormone shot was much more effective than pills. Max had one year on HRT, and he couldn’t stop grinning at himself.

He slipped on a pair of new cork slides with two-inch heels and grabbed a towel and sunblock from his bathroom. As he went out, he grabbed two bottled waters and a piece of fruit. He threw his towel on the recliner and dove into the water.

He swam ten laps before he rested on the side. He checked his pulse and was pleased to see that the exercise hadn’t stressed his system. He did another ten laps and got out. He went over and applied sunblock to his legs and feet. Then he started on his arms. Rather than try to do his body around his bathing suit top, he undid the laces and removed it revealing his nicely shaped AA-cup breasts.

Max was looking forward to a month of leaving them unbound and unfettered. No Ace bandages, no coverups, no hiding himself anymore. This was a real staycation. He could be his real self for a month. Max saw it as the start of his new life. When he returned to school, he’d have a new ID, and all his record requests would have been processed saying he was now female.

This was going to be the best staycation ever.

He was laying back on the lounger applying lotion to his breasts. Max closed his eyes. It felt so good to be toying with his breasts outside with no one around. It was a delicious feeling as that warm surge beginning to build inside his body.

Suddenly the sound of the back gate slamming shut woke him out of his reverie. Somebody was in their pool area beside him. He felt panic until he heard a very familiar voice.

“Hey, Max. Your mom told me you were coming home this afternoon and I thought I’d surprise you.”

Robert was walking the length of the pool apron and really hadn’t seen Max up close yet. Thank goodness for an Olympic sized pool, he thought as he hurriedly slipped his top on and tried to figure out what to do.

He hadn’t thought to bring out a cover-up, but the towel might hide his two-piece. He grabbed it up and tucked it under his arms. The oversized bath towel draped his body and covered his bright orange bikini bottoms.

“Hey, Robby. What a surprise. How you doing?

Robert was still not looking at Max but dragging a lounge chair over. Then he turned, taking off his shirt and pants. He was wearing a baggy set of trunks. “Good, man, doing real good. I’m in town for a month and thought we could do some stuff together. I have to report back to training camp and preseason practice in August. The coach said I’m going to start varsity as a defensive back this season, cool huh?

Max was spellbound and entirely forgot everything. While he had talked to Robby at least once a week, he hadn't seen him in a year. His best friend from high school appeared to have doubled in mass, and it was all muscle. Robby was always buff in high school, but one year at college and he'd become a grown man. Robert was beautiful. He looked like a Greek statue.

At this point, Robby was close enough to see Max up close. He glanced up, looked carefully, then kept staring. “Uh, Max. You really look different. What’s up, dude?

Max sat up and dropped the towel. With his shoulder length hair and his orange bikini, there was no hiding what was happening. He sighed. “Robby, I’m transitioning. I’m finally going to a woman.”

Robby looked closely. “Oh, wow. Amazing. But, how come you never said anything to me? We talk all the time. I thought we were good friends.”

Max shook his head and had to push his hair out of his face. The touch of makeup he wore made him self-conscious as his hair stuck to his lip gloss. “Uh, I didn’t know where to start. It’s been in the works for years but, well, I didn’t know what to say. I guess I’m a coward.”

Robby sat down on the lounger right next to him. “Your face looks really nice. You’re very pretty. You really look amazing, beautiful.”

Max blushed. “Really? I had some work done last summer after graduation. They call it facial feminization surgery. You want the whole story?”

Robby nodded and shrugged his shoulders. Looking straight into Max’s eyes, he spoke softly. “I got nowhere to go, Max.”

Max began. “Last summer, my mom and I flew to Chicago, and I had facial surgery before I started my freshman year.

“I recovered in Chicago for a month before traveling back to Florida for school.

Robby nodded. “How long have you been planning all this? When did you know you were trans?”

Max was surprised that his friend was taking this so calmly, “I’d been under the care of a psychiatrist and an endocrinologist since I was twelve. Mom and I talked over and over about this since I was five years old and diagnosed with gender dysphoria. Mom’s solution was to find me the right doctors and put her trust in them. Even though we lived from paycheck to paycheck, she made my happiness her priority.”

“So I was started on anti-androgens before my body started producing testosterone.”

Robby nodded. “You were always a little different, but I mean, you never looked different or acted girly. How come?”

“I was scared of being thought of different as everyone else. I’ve been hiding my true self all my life. I didn’t want to make waves. I know I should have just bit the bullet and come out, but I’m a coward. I still haven’t even told my step-dad, Henry.

“I think mom is telling him the whole story while they’re away on their cruise. I was closeted at school this year. My stuff still says male all over it.”

Robby smiled. “So today's your coming out party, and I’m the first to know. This is cool.”

Max looked at Robby strangely. “Why are you so elated?”

Robby stood up and started pacing. “Max, you don’t know how this makes me feel. This is so great!”


Robby sat back down and moved over, so their hips touched on the lounger. “Max. I don’t know how to say this.” He took a deep breath and put his hand on Max’s leg. “I’ve had the biggest crush on you all through high school, and I was afraid to say anything. I was afraid you’d reject me, and I didn’t want to mess up our friendship. I didn’t want to push myself on you!”

Robby stood there smiling. “It all works out. It all makes sense now. I can tell you I love you and do this.”

Robby leaned over the chaise and kissed Max on the lips. He looked his best friend in the eyes.

“Congratulations, Max. Welcome home.”

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