Fifty and Out

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Fifty and Out

By Dee Sylvan

June 2023

I’m sitting in my car wondering what in the heck has gotten into me. The Grande Ballroom is hosting my 50-year class reunion and I’m in the parking lot, ready to walk in, but…

18 months ago, somewhere in the Thumb region…

Rachel, one of my best friends from High School and the former homecoming queen, is showing up on my caller id. “Hi Alex, would you be interested in helping plan our 50th high school reunion for the Fort Austin Pirates?”

“Hi Rachel, I’d be glad to, but why me? We’ve had class reunions every five years and you’ve never enlisted my help for any in the past.”

“Well Alex, the people that have been on the committee in the past are either burned out or aren’t available, so Marcia and I are reaching out to some others. Since you’ve had your family business for the past 40 years and are now divorced and retired, we thought you might have time to help.”

“What about our illustrious class leaders Jan and Greg? Are they helping?” Jan and Greg were the President and Vice-President of our class, the Prom King and Queen, and the ‘it’ couple during high school. Unfortunately for Greg, Jan broke up with him right after prom when she learned he was dealing drugs and cheating on her.

“No, after 50 years, there is still too much drama going on with those two. At the last reunion, a cat fight nearly broke out between Greg’s wife Cindy, and Jan.”

“Betrayals are hard to get over,” I chuckled, then immediately regretted my little self-indulgence. “Count me in. I’ll see you at the organizing meeting.”

“We want to use our class song as the theme of our reunion,” Marcia said after bringing the meeting to order. We were meeting at the mansion of Sheldon, our class nerd whose video game ‘Clash of the Titans’ had made him a multi-millionaire.

“We will use our class song, ‘Reelin in the Years’ to highlight the events of the year of our graduation.”

“How did that song ever win over ‘Let’s Get it On’,?” smirked Joey, who thought of himself as our class lothario, even if he was alone in that thought.

“I thought you were campaigning for ‘You’re So Vain’, Joey?” I snarked. “Are we going to ask our celebrity classmate, Chandler, to be the MC for the event? He told me he is considering coming back for the event.”

“Well, you would know better than anyone Alex,” Marcia remarked. You and Chandler have been BFF’s since you were what, four or five years old? How is it that he never got married despite being a star in the NFL?”

“I guess Chandler never found his soul mate. God only knows how many starlets have thrown themselves at him over the years. His Foundation has done a ton of good things across the country in the LGBT community, despite him getting constantly attacked in the media for it. He’s going to be hosting a charitable pro-am event with many of the stars from the LPGA a few weeks after our reunion in nearby Saginaw. The guy has a heart of gold.”

“Are you going to his New Years Eve bash again this year Alex? Try to twist his arm to make sure he is at the reunion. Our attendance will go through the roof if he commits to coming.”

“Yes, it’s a real fun time and he always insists on me flying out there right after Christmas so we can hang out for a week. He told me this year he wanted to drive up to Napa Valley to do the winery tour. Hopefully, we’ll have time to play Pebble Beach and Spyglass, too. He loves hanging with the celebs there.”

Spring 1973
50 Years Ago

“Alex, who are you going to take to the Prom?” asked Chandler, his best friend and next-door neighbor.

“You know me Chandler, I’m solidly in the ‘friend zone’ with most of the eligible girls.”

“Alex, you’re the valedictorian and have more varsity letters than anyone else in our class. You could ask anyone, and they’d go in a heartbeat. Besides, everyone knows that sooner or later you’ll be running your dad’s manufacturing business.”

“Be serious, no one comes to the golf matches, or the tennis or swim meets, Chandler. I’m helping Phoebe make her Prom dress because she wants to look special on the arm of the star quarterback who is going to State University on a scholarship- that’s you.”

“I saw you getting cozy with Monica in the library yesterday, Chandler. That girl was making goo-goo eyes at you. You must admit you have a certain attraction with the ladies.”

“Come on Chandler, you know she was pissed at you for not asking her to Prom. She was getting all flirty with me because she wants me to design and make a one-of-a-kind dress for her so she can show up Phoebe. I was just hoping for one of the gals that came in second place in the Chandler sweepstakes. She broke my heart when she said she knew I was only kidding about taking her to the prom. Haha, what a joker.”

“What about Rachel? She’s been following you around for the last couple of days like a puppy dog. You could take our Homecoming Queen and Head Cheerleader to Prom.”

“Chandler, you know Rachel has her heart set on going with Ross. She has been begging me to get him to ask her. Besides, she has told all her girlfriends I’ve agreed to help her with her nails and make-up. Who do you think wants to go to Prom with a guy with those skills”?

“It’s your own fault for taking all those home economics and fashion classes Alex. What were you thinking?”

“I was thinking that knowing how to cook, sew and type are skills I’ll need in college Chandler. I’ve already taken all the AP classes. I’m trying to talk Miss Rowland into letting me design and make Monica’s dress for my final exam so I can kill two birds with one stone.” Besides, I’m in classes with the hottest girls in school while you’re learning to change your oil in shop classes. And yet, you still ask me to fine tune the supercharger on your Firebird! Why don’t you set me up with Penny, Chandler? You know she would do just about anything for you.”

“C’mon Alex, man up and ask her yourself! You’re friends with every girl in our class. And Penny is still mad that we broke up after basketball season. She was talking marriage for gods’ sake! I’m keeping my distance from her.”

2008
15 Years Ago

“Alex, we need to talk” said Patricia, his wife of 25 years.

“What do we need to talk about Patty?

Elise, the youngest of our five kids, graduates in two months from Brown, and our house has been paid off. I will be moving our son, Chase into the plant manager role due to his mechanical engineering degree and our daughter Melody will be moving from plant manager to VP of Ops this fall when Richard retires. Peter just got promoted to Captain and looks like he will make his career in the Air Force. Lisa just got her Masters degree and is starting on her Phd program this fall. And we have two grandchildren we love to spoil.

Our plan to retire at in 10 years is on track, and I can’t wait to travel extensively in and especially to see Great Britain, Italy, and Greece. What is it that we need to discuss?”

“I want a divorce, Alex. I’ve met someone and have fallen in love. I don’t want to hurt you, so I want to handle this in a civilized way.”

“I thought we were in love, Patty. Is this about your pal Benedict? I’ve heard about the two of you at the club. You haven’t been very discreet. Is this about Benedict’s real estate venture that is floundering because he can’t get the zoning board’s approval that investors are shying away from?”

“I want to expand my horizons, Alex. Ben said that once his zoning request is approved, he’ll be able to build his upscale housing development near the new High School. You’ve never been ambitious, Alex. Ben is the kind of man I admire and want to spend my retirement with.

I just want what is coming to me. We can split everything 50-50. You can keep the house and pay me half of the equity. Your father’s business, McDonald Douglas Manufacturing has grown and prospered, yet we’ve never seen any significant raises or dividends. Ben said with over 150 employees, it must be extremely profitable. Yet we’re driving two-year-old cars and still live in the farmhouse that you grew up in.”

“So, Benedict is now an expert in Manufacturing as well as someone who would encourage a married woman to cheat on her vows. Is this the type of man that you admire?”

“We didn’t plan on falling in love, Alex, it just happened.”

“This is a small town, Patty. Your tryst with Benedict is not a very well-kept secret. I would think about this long and hard, dearest. Just because Benedict’s plans are foundering and he thinks you have access to a large sum of money, doesn’t mean this is going to end well for you.”

“Alex, I have put up with your cross dressing ‘hobby’ for a long time. But if you give us any trouble on this, our ‘small town’ is going to find out about it, and you will be humiliated. Benedict says no real man would ever put on women’s clothes. He has opened my eyes, Alex. Do you want your children, your family, your employees, and your friends to know about your ‘secret’”?

“Oh Patty, how far down the rabbit hole have you fallen? Do you really think you’re going to blackmail me, and this will turn out good for you? This has gone far enough. This is your last chance, Patty. Tell Benedict this is over, and we’ll get a marriage counselor to help us. If not, trust me, you’re not going to be happy.

Take the weekend to think this over. If you are determined to continue this affair with Benedict, I will see a divorce attorney on Monday. But I can guarantee that you will not like the outcome.”

December 27, 2022
San Jose International Airport

“Alex McDonald”
The middle-aged blonde was holding the sign as Alex moved into the luggage area. A grin spread across his face as he approached the woman.

“Where is Chandler? Alex asked as the physically impressive lady helped him gather his luggage and then escorted him outside.

Standing next to the stretch Hummer limo, Chandler was standing with an equally beautiful brunette.

“Hi buddy” Chandler greeted Alex with a warm ‘best friends’ hug. “Let me introduce you to the O’Donoghue twins, Carol and Cathy. They are going to be our tour guides for our trip to Napa and then the Monterey Peninsula. As I recall, you prefer blondes. You’re with Carol. Let’s go!”

Alex and Chandler caught up on their lives during the two-hour ride that ended at the Castello di Amorosa. Carol helped Alex out and grabbed his arm as they toured in the impressive castle winery site.

“We are only going to take in three wineries today and then we are spending the night at the Pebble Beach Resort. Tomorrow, the girls are going to accompany us for the full spa treatment in the morning, then we play Pebble at 1pm. Tomorrow night, we’ll eat and then do some dancing. Friday, we play Spyglass in the morning, then we’ll head back to my ranch. The girls have a lot to do to coordinate all the caterers for the New Year’s Eve party.”

“Who are we golfing with Chandler? Clint Eastwood and Bill Murray?”

“Are you kidding? Those guys are hacks. But we may see them Monday night at the party.

Carol and Cathy were All-Americans golfers as well as MBAs at Stanford. Now they work with me at the Foundation. Don’t worry, Carol is the better golfer, so you may have a chance to win some of your money back from last year.”

It was like old times for the two best friends. Alex was the better golfer although Chandler’s drives were 20-30 yards farther, but seldom in the fairway. Pebble Beach and Spyglass are two of the finest courses in the country and the groundcrews were busy getting them set up for PGA event in a few months. The views of the Pacific were breathtaking, and the views of the O’Donoghue twins were a close second.

On Saturday, Alex and Chandler went for a horseback ride on Chandler’s ranch north of Lake Merced and stopped to enjoy lunch overlooking the Pacific.

“Have you been seeing anyone back home Alex?”

“Nope, not after Patty’s affair and our well-publicized divorce. Once bitten, twice shy.”

“I know it’s a sore spot, but whatever happened? I thought you two were soulmates. I know that your kids all turned out great.”

“Ben Arnold happened. He had Patty convinced she could get millions from a divorce and fund his real estate project that was in trouble from the start because of a lack of investors. Patty thought she was going to live the life of the rich and famous.

But we were never soulmates, Chandler. After you got drafted and headed to the NFL, I got busy with dad’s business and had a good run. Our hometown prospered along with our company, and I met Patty when she came to work for us. Patty was a good wife and mother, but it seemed that everything was always about Patty.

Ben convinced her that she could get whatever she wanted from me with the threat of ‘outing’ my ‘dressing up’. She didn’t realize my feminine side was no secret to our high school gang.

But Patty and Ben’s dream of forcing me to sell the house and business in the divorce went up in smoke when they found out during discovery that the house and business were untouchable because of the way my dad had set up the family trust.”

“The fact that your family’s business employed half the town and the charities that it funded did so much for the area must not have endeared Patty and Benedict to the Fort Austin community.”

“That is the understatement of the century, Chandler. I tried to warn Patty she was not going to like the outcome, but all she saw were dollar signs. After the divorce, she and Ben ended up moving to Toledo to get away from the angry mob coming after them with torches and pitchforks. Of course, their marriage was doomed from the start and only lasted so long as Patty was getting alimony. That was about five years, now she’s back in the area so she can at least see her grandkids.

“Everyone in Fort Austin wants you to come back for our 50-year class reunion Chandler. I know you have that pro-am event in July for the LPGA in Midland. Do you think the twins can spare you for a night?”

“I’ll have to check the schedule. They are also playing in the pro-am. In fact, they need a fourth golfer for their group. Would you like to play with Carol and Cathy and the LPGA pro?”

“I thought you were trying to restrict the pro-am to only women golfers?”

“I didn’t think that would be a problem for you. You’ll even get to hit from the forward tees. You might even be able to outdrive Carol this time. Haha

Have you made any New Year’s resolutions this year Alex?”

“I have, but it’s the same one I’ve made for a countless number of years. And I always break it.”

“What about you Chandler? Is there anything on your bucket list that you haven’t done yet? Climb Mt. Kilimanjaro? Scuba dive the Great Barrier Reef? Spend a weekend with Stevie Nicks?”

“Those things are overrated Alex. Even you could climb Kilimanjaro. Haha

There is one resolution on my list this year. One that I think is going to happen. I’ll let you know when I see you this summer. Let’s head back.”

Back to the Reunion…

My resolution. The one that I have made and broken since high school hangs in the balance.

I just saw Chandler arrive so I know at least one person here will have my back.

As I push open the entrance, the first person I see is… Rachel.

“Hi Rachel.”

“OH MY GOD!!! You look awesome Alex! Should we call you Alex? I love that dress. Who did your make-up? Is that a wig? It’s not, is it??? Look at you, walking in stilettos. It’s about time, Alex! Chandler is never going to believe this. He just came in and was looking for you. C’mon!”

“Call me Lexi and quit pulling me.”

“CHANDLER! CHANDLER! Look who finally arrived, your BFF, LEXI!

“I can’t believe you came out Lexi!”

As I stand there like a deer staring into headlights, Chandler leans me back and before I know what’s happening, gives me a full-on kiss. That was better than I imagined!

“It’s about time Lexi! I’ve been waiting for 50 years to do that.” I guess both of our New Year’s Resolutions came true this year! I’ve finally found my soulmate!”

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Comments

I finally found my soulmate!

giggles. well, better late than never, right?

I love the names - you watched too much Friends, didn't you?

have a Dottie huggle for making me giggle.

DogSig.png

My First Huggle!

Dee Sylvan's picture

Thanks Dot! A little Friends v Brady Bunch & Big Bang. :DD TAF

DeeDee

Soulmates

joannebarbarella's picture

Always there but never consummated until a bold move made it possible. No wonder neither of them responded to all the other opportunities along life's way.

Regrets, I've had a few...

Dee Sylvan's picture

Just one bold move away from a life of happiness and joy. Thanks Jo! :DD TAF

DeeDee

Thrilled

Emma Anne Tate's picture

Thrilled to see your by-line on a story again, Dee!

Emma

Recency bias...lol

Dee Sylvan's picture

Thanks to you, Jill, and Jo for getting '24 off with a bang, Miss Emma! It was fun to get back in the saddle again. My other story isn't long enough to qualify, but it will be coming soon. I'm a woman of my word. :DD TAF

DeeDee

I Love Your Humor

However -- where's the love for Roberta Flack's Killing Me Softly?

Jill

Angela Rasch (Jill M I)

PC

Dee Sylvan's picture

Our class song, even though we graduated in '73, was a song called 'Stairway to Heaven' that was released in '71 by some obscure English Band. I couldn't resist taking a swipe at Joey with Carly Simon's classic.

Back in 73, things were a bit different-lol. I doubt even the greatest quarterback of that era like a Dan Marino or Terry Bradshaw (both won Super Bowls) would even have been drafted if they were gay. No one would have even known what trans was, let alone dating or marrying a transwoman. I'm working on a story about the cost of transitioning, it is a fascinating topic.

In this story, the elephant in the room, perhaps in the entire community was Alex's dressing. It was his probably his close friendship with Chandler that kept Alex from being an outcast in high school. But Alex's wife and her paramour seriously underestimated the long-term friendships as well as the economic loyalty that Alex and his family built up in their small town when Patty attempted her blackmail.

At age 68, with their successful careers behind them, and being financially well off, what was the risk to Alex and Chandler of professing being soulmates? The risk was pretty insignificant compared to what it would have been at age 18.

Unfortunately, as we all know, there is always a cost.

Thanks for the comment Jill! And thank you for sponsoring the contest! :DD TAF

DeeDee

True love at last

But why did it take them 50 years?
That sent details that were meant to confuse, at every stage of the tale.
Right up until the end. Beautifully told.

Polly J

50 Years is a long time

Dee Sylvan's picture

See my comment above to Jill about the cost of transitioning. Carrying his trans secret and affection to Chandler for 50 years was a heavy burden, but one that many of us have also carried.

Thanks for commenting Polly. :DD TAF

DeeDee

Living as a woman

Wendy Jean's picture

And having a soul mate! Could life get any better?

I must confess

Dee Sylvan's picture

If I could write myself into this story, I wouldn't change a thing.

Thanks for the nice note, Wendy. :DD TAF

DeeDee

Glad to see you wielding your writing skills again

SammyC's picture

A touching story, Dee. I think the 5,000 word limit kept it from really soaring. So much of your own backstory went into this and the emotional resonance is heartfelt. Please expand this when you get the time and motivation. I know your "new" life is so busy these days. Thank you for the story.

Hugs,

Sammy

Steely Dan

Dee Sylvan's picture

'Reelin in the Years' was picked for the class song in your honor, Sammy. This was the cliff notes version of a lot longer story, but I wanted to make sure I was in compliance with our judges. I am getting a lot of new ideas from some of the things going on in my 'new' life. Tutoring at-risk grade school school kids has been a real eye-opener and surprises every day.

I must admit, I did enjoy writing this story. It was challenging to really develop the characters in the word limit, but at least it got me enthused about writing again. I am going to be a model in a LGBT 50+ charity fashion show in a couple of weeks and you wouldn't believe the drama that has happened leading up to it.

My name officially was changed this past Valentines Day, so I'll be busy changing all my documents, social media, etc. in the coming weeks. Yes, lots of stuff going on. Hope you're doing well, Sammy. :DD TAF

DeeDee

A brief flash.

Sunflowerchan's picture

This story ended all too quickly for me, I noticed you had uploaded a new story while I was on break, and vowed to post a public comment as soon as I could. Dee you are a truly gifted writer, and this story was a brief, flash, a taste of what you can do. I hope one day to see a full tour-de-force of your creative talent and to see this story fleshed out. You showed us with stark reality what fifty years of carring around a burden can do to you. Of what was given up and put into a tiny box in the name of achiving what many of us consider life goals. I'm left breathless as I try to progress all the scenes unfolding before me, please, please, please Miss. DeeDee when you get a chance make this a full story, it would a treasure, a classic, and I'm sure will enjoyed by future generations of readers. Thank you again for sharing this wonderful story with us here on the site, and for being a postive role-model in young peoples life. You are a treasure and a gem online and offline.

I'm no longer an observer

Dee Sylvan's picture

Thank you for the kind words. It's been difficult to write while I was going through some tough times. Your stories and other authors have given me inspiration to start writing again. My class reunion was last year so this story has been rattling around in my head for some time. Emma and Jill and Joanne did me a big favor by introducing this contest and challenging me to contribute. I have enjoyed writing, but this story was more of an outline and I wasn't able to do it justice in a small window. But I agree with you there is much more to Alex and Chandler and their story.

Thank you for your support both offline and online. At 68, all of a sudden, my life is richer and fuller than I can ever remember. I have been fostering a delightful puppy, I named Emma for many months, and today I gave her to beautiful family with three small children. It just seems like after the gloomiest holiday season I have ever had, that the sun is shining again.

I hope to post another story quite soon. Thanks for being a friend. :DD TAF

DeeDee

This year will be my 45th High School reunion……

D. Eden's picture

As I graduated in 1978. I have not attended a single reunion - I left home a few short weeks after graduating and never went back; well, that’s not completely true. I did actually go back to attend two funerals - the first five years after I graduated, and the second eight years after I graduated. Both trips were for less than three days, and other than the people I saw at the funerals I have had zero interaction with anyone I graduated with, or even anyone I went to school with. And since then, I have not spoken with or seen a single person.

I began my transition some ten years ago, and have been living full time as a woman for the past eight years - a fact that as far as I am aware, no one I went to school with is cognizant of.

I have been seriously thinking about attending my reunion this year, although I doubt my spouse will want to go with me. This story really reminded me of the fact that I have been thinking of attending - but there will be several differences.

1) No one I went to school with had any reason to think I might be transgender - I was so far in denial that even I didn’t know.
2) There will be no one there to kiss me - rather, the question is whether or not anyone would even speak to me.
3) Although my spouse is very supportive of me, she would probably be too embarrassed to go with me. She has gotten much better with the attention, but I doubt she would be able to handle having everyone at the reunion staring at us.

This was a wonderful story, but I will never know this fairy tale ending.

D. Eden

Dum Vivimus, Vivamus

Coincidence? Maybe not...

Dee Sylvan's picture

I was a closeted cross dresser in junior high and high school like many on this site, although how secret that was is up for debate. But high school for me were some of the best of times. I had a large group of friends that tended to go out as a group and we remain friends to this day. I debated about coming to the reunion 'dressed up', but ultimately decided it would distract from my catching up with friends I hadn't seen in 50 years. In retrospect, I should have gone with my instincts. When I came out to my friends a few months later, it was a classic case of 'what took you so long?', lol. But without a Chandler sweeping me off my feet.

If any of my high school friends ever read this, they will have a chuckle at some of the people in the story that have an eerie similarity to people from my high school, including me. I always thought I would be married forever to my ex. Despite the pain she inflicted on our whole family, she actually did me a big favor by abandoning our marriage of 28 years. I never would have transitioned and would still be firmly in the closet, watching the world pass by. Even then, it still took a bout with cancer for me to make the decision.

I just feel like there are so many things I want to accomplish in my life, even at 68 years old. Number 1 on my list is to do my best to address the unbelievably high suicide rate in the trans community. I feel fortunate to live in a state (MI) with perhaps the most supportive LGBT governor in the nation. One of my new girlfriends recently suffered through this tragedy with her own children and the devastation it has wrought is immense on those left behind, let alone the senseless waste of a young life cut short.

I always appreciate reading your thoughtful comments Dallas. Thank you for sharing and commenting on my story. :DD TAF

DeeDee