The Roads Converge

After Tommy let Archie out onto the terrace, we stood by the French doors in the dining room and watched him playing in the snow. “He’s so cute!” I exclaimed. “Just don’t forget to let him back inside.”

Tommy kept me company while I busied myself in the kitchen. He was amused when I tied one of Helen’s old aprons around my dress to protect it before I put oven mitts on my hands and carefully removed the stroganoff from the oven. “You know, I’ve been watching you,” he said, “and your every little movement seems so feminine. I never noticed that about you before in all the years I’ve known you.”

“Well, you try acting like a guy when you’re wearing these heels, buddy.”

“I see what you mean. It’s amazing that you’re able to get around in them so well.”

“Around the house they’re okay. I don’t think I’d last five minutes in them out on the sidewalk. But I salvaged a pair of Helen’s tall boots that are really quite comfy, just in case you’re planning to take me anywhere,” I said hopefully.

“Sweetheart, all your restaurants are closed except for outdoor dining, and I really don’t think eating al fresco in the snow sounds very appealing.”

“I know that, silly! But you could take me for a stroll down Michigan Avenue to check out the lights and do some shopping.”

“It’s a date, if Gene can loan me one of his old parkas till I can find one that fits me.”

“Ah, now I know what to get you for Christmas!”

Our conversation continued along those playful lines while I tossed a salad and served up the stroganoff. Tommy poured the wine, and he pulled back my chair when it was time to sit down. “Such a gentleman! I could get used to keeping you around.”

“Baby, you’re never getting rid of me.”

* * *

Dinner was delicious, one of Helen’s special recipes that had me feeling very nostalgic. We toasted her, and then I said a little prayer for Helen. “If she’s up there somewhere, looking down on us, I hope she’ll understand.”

“I don’t think any wife will ever truly understand her husband wanting to become a woman,” Tommy observed. “From what I’ve read – and believe me, over the last week I’ve spent hours pouring over everything I could find on the web about crossdressing, gender dysphoria, you name it – a lot of women come to terms with it, and some even stay with their husbands, but think about how difficult that must be: her knight in shining armor wishing he was a girl.”

“I know. I guess I’m glad Helen never had to cope this this,” I said sadly.

“‘This is who you are now. Jeanne was never a part of Helen’s world. The end of her life was tragic, but right up until the end she always had her man to look after her. Now she’s gone to a better place, and you have to let her go,” Tommy said gently.

“Someday maybe I can explain it to her. Although I’m not sure I really understand it myself. All I know is, for some reason this is the person I want to be, I have to be, if I’m ever going to be happy. And I am happy, now that you’re back in my life, Tommy.”

He raised his glass. “Here’s to Helen, who made my best friend the happiest man in the world, and here’s to Jeanne, who let me take his place.”

* * *

After Tommy helped me clear the table and load the dishwasher, we took the last of the wine into the living room and snuggled on the carpet in front of the tree. The fireplace gave off a lovely glow, and the tree lights and ornaments glistened like a scene from a childhood dream. I kicked off my heels, and Tommy rubbed my aching toes through my nylons. “That feels soooo good,” I sighed.

“My mission is life is to make you feel good. Last weekend was only the beginning.” He placed our empty wine glasses on the coffee table, and then he reached under my dress and gently slipped off my hose. After a moment’s confusion, he was able to unsnap the bottom of my teddy, and then my dress – I had to help him by unfastening my belt, but I let him do the rest, it felt so wonderful to feel his strong hands carefully sliding it up and off me. He stood up and I watched as he tore off his shirt, dropped his trousers and sat back down beside me in his sox and underwear, which I quickly removed. Then he lay back on the carpet and asked me if I wanted to try something new.

“You mean like a new position?”

“Yes. Before last weekend, I hadn’t had sex in years, so I think we can dispense with the condoms…”. His penis was ripe with precum, and after I massaged it all over, he instructed me to sit down, facing him, and with a little guidance from Tommy I was soon impaling myself on his stiff manhood. After the usual shock of pain, I felt him sliding easily into me, and gravity took care of the rest until he was all the way in, up to the hilt, and instinctively I started to ride him, up and down, up and down, while his fingers grasped my penis and he began to stroke me towards climax to the rhythm of my movements. The sensation of his warm, naked penis against my tender insides was exquisite, and for the first time I was able to look into his eyes while we made love, which made it all the more intimate and exciting. Feeling every inch a woman in my slip and teddy, I kept bouncing up and down on his penis, and he kept tugging on mine, until suddenly we both came together in a rush of sheer ecstasy for both of us, long, lovely orgasms that rocked us to our very souls.

When at last it was over, I kept him inside me and kept staring into his eyes while we slowly came down to earth. “That’s called the cowgirl,” he sighed.

“Yippee ki-yay, motherfucker!” I said in my best Bruce Willis. He laughed so hard that I could feel his penis shaking inside me, and I almost had another orgasm.

* * *

Archie! We were so engrossed in our lovemaking that we forgot all about him, and the poor thing was shaking like a leaf when Tommy let him in from the terrace. We wrapped a blanket around him and the three of us huddled together by the fireplace until he finally warmed up. Then I picked up my dress, shoes and stockings, and Tommy and Archie followed me up the stairs to my bedroom. Tommy handed me my suitcase from Florida, and I quickly opened it up and removed my other wig. He looked at me quizzically, but I just told him, “You’ll see,” before I grabbed a nightgown and panties from one of the dresser drawers and excused myself, closing the bathroom door behind me.

When I emerged a few minutes later, my makeup had been removed – the first time Tommy had seen me that way – and Helen’s old wig was on my head. “I never want you to see me as Gene again, “I explained, ” but I don’t want to mess up my new wig by sleeping in it every night, so my solution is to save the new one to wear during the day, and sleep in the old one. I think I could also use it for sports and stuff, like if we ever play golf or tennis down in Florida, and I could even wear it with a swimsuit. I hope you don’t find me too frightening without my makeup?”

Tommy hugged me and laughed. “My dear Jeanne, I would be equally attracted to you as a guy. That’s one of the advantages of having a gay boyfriend. I’m just blown away by the lengths you go to preserve the illusion of femininity.”

“I know, it’s weird, and all of this is new to me so it’s all trial and error, but I’m loving everything about being a woman. Now put on your pajamas and let’s go to bed.”

“Who said anything about pajamas?” he laughed, but he’d brought some, and after he was finished in the bathroom, he joined me – and Archie – under the covers for a long winter’s nap. My first threesome!

* * *

Tommy got out of bed first the next morning, and after he shaved and showered he was ready to take Archie out for a walk. I found the largest winter coat on Gene’s side of the closet, and although it was a little snug on him, he said it would do and they headed down the stairs. While they were gone, I had a quick shave and shower myself, put on my new wig and makeup, and started to sift through the meager offerings that I’d squirreled away before my daughters cleaned out Helen’s half of the closet. I selected a cashmere turtleneck sweater – it was incredibly soft, my wife had excellent taste – and a long wool skirt, and underneath I put on lingerie and some opaque tights that I hoped would be warmer than nylons. After I zipped up my boots, which came to the middle of my calves, I finished myself off with a scarf and some jewelry, and I played with my scarf in the mirror while I admired the way my new breastforms filled out my sweater. Not bad for an old lady!

By the time Tommy and Archie were back from their walk, I’d just finished making the coffee and heating up some cinnamon rolls from Ann Sather. Tommy looked like he’d just been to the North Pole, and he sat shivering in the kitchen while he wolfed down his roll and mainlined black coffee. “I’d forgotten how fucking cold it gets up here, but it all came back to me this morning.”

“Well, bah humbug to you too, Mister!”

“Are you honestly telling me you prefer Chicago to Florida?”

“Chicago gets in your blood. On the other hand, you do live on the most beautiful beach I’ve ever seen. Maybe we could divide our time, and try living in both places?”

“Are you asking me to move in with you?”

“Yes,” I said without hesitation. “Have I scared you off?”

“No, I was planning to ask you the same question, but you beat me to it. You’re just a bit faster than the average woman. That’s one of the advantages of having a guy for a girlfriend.”

I punched him on the arm, hard. “Ouch!”

“I’m sorry,” I quickly said. “I shouldn’t have done that.”

“Jeanne, Jeanne, Jeanne,” he said, taking me in his arms. He kissed me on the forehead – without last night’s heels, I felt like a little girl in his arms. “Love means never having to say you’re sorry.”

“Hey, is that original?”


“Are you calling me a guy?” I swatted him with the dishtowel I was holding.

“God, I love you so much! I secretly fell in love with you as Gene over forty years ago, and now that you’re finally back in my life, I’m never letting go. Never.”

“Till death do us part then?” I teased him, looking down at my empty ring finger. I’d slipped my gold wedding band into Helen’s hand before she was buried.

“Well, let’s not get ahead of ourselves. For one thing, we have Laura and Carolyn to consider.”

Our conversation was turning serious, and we both sat down and sipped our coffees. “I’ve actually been thinking about them, a lot. Sometimes it seems like the best thing is for me to become some kind of shapeshifter, and morph back into their father whenever we get together. This crazy pandemic isn’t going to last forever, you know.”

“And the other times?”

“Well, I’m not quite ready to waltz back into their lives dressed in their mother’s clothing, with Uncle Tommy on my arm.”

“I get that.”

“But I can’t shake the feeling that somehow I’m selling them short. They’re intelligent, sensitive women, they both married intelligent, sensitive men, and their kids are really too young to understand what gender means. And our society is changing very fast. What was shocking a few years is now commonplace.”

“Sounds like something out of Cole Porter.” Without warning, Tommy burst into song in his rich, deep baritone:

“When grandpapa who’s over fifty

Thinks being a girl is nifty

In grandma’s clothes

Anything goes!”

When I finally stopped laughing, I could only say, “What is it about gay guys and Broadway musicals?”

“That’s a stereotype! I’m surprised at you, of all people.”

“Anything goes, all right. Seriously, if I were to tell the girls that I’m gay, and that I was living with you, I’m sure they’d be shocked, but I’ll bet they could handle it. But I’m a lot less confident about telling them that I’m living as a woman. It’s one thing for them to have a gay dad, but to have their father, as they’ve known him all their lives, disappear into a completely different person, so soon after losing their mother? I’m not sure how anybody handles that….”

He reached over and took my hand. “My advice is to leave things as they are for now. Let’s drive down to the Magnificent Mile, we’ll look at the pretty lights, find me a warm coat, and I’ll help you pick out some clothes to get you through the next couple of weeks. Then we’ll drive back down to Florida, and I’ll help you pick out a golf skirt, a tennis dress, a swimsuit….”

* * *

We decided to return to Florida as Tommy and Gene on Christmas Day, for three reasons: the long range forecast called for clearing skies before another round of snowstorms moved in; both of my daughters would be up before dawn with their preschool children, and with the one hour time difference, I could do my Zoom and FaceTime thing as Gene before we hit the road; and I had no intention of presenting myself as a woman in gas station restrooms in the Deep South!

It was a little sad packing Jeanne’s suitcase again. Our excursions on Michigan Avenue had yielded a fine collection of skirts, tops, dresses and pants (I quickly learned that even long skirts, tights and boots were no match for the Chicago winter) on Jeanne’s side of the closet, and now I was leaving them all behind. When I remarked to Tommy that I’d have some explaining to do if my daughters ever saw that closet again – say I was in an accident or got sick somewhere – he replied, “That’s an easy one. Tell them you have a new lady friend.”

“You’re the one with the new lady friend,” I told him as we both got dressed for our last night in Chicago. By now, we were almost like an old married couple, and I even let Tommy see me without my wig on when I went in and out of the bathtub or shower. “Tell me, don’t you find it a trifle boring to spend so much time with a female?”

“No, because I’m in on the secret in your panties. But when I was in high school, I actually envied girls sometimes – they were the ones who got to go out with all the cool guys.”

“We are a pair, aren’t we?” He watched me while I eased on a pair of thigh high stockings and endured the daily struggle with my conflicted manhood. “There, that oughta hold him for a while,” I sighed after my penis was safely tucked back between my legs.

He continued watching me as I stepped into my half slip and poured myself into my slinky little dress. “Zip me up, please?” I asked him sweetly.

“What would you ever do without me?” he said as I felt my dress tighten around me. “Hmmm, your ears look perfect.” After a little encouragement from Tommy, I’d gotten them pierced, and tonight I’d replaced my trainer studs with an elegant pair of diamond earrings that he’d surprised me with.

“Thanks, please don’t let me forget to take them off before we talk to the kids tomorrow!” After much deliberation, we’d concocted a story that we were going to spring on my daughters: Uncle Tommy had shown up out of the blue in Chicago to cheer me up, and since he was driving back to Florida on Christmas to beat the next blizzard, I’d accepted his invitation to spend some time down there. They loved Tommy, and I was pretty sure that they’d be happy that their father wasn’t going to have to spend Christmas alone.

I stepped into my heels, and Tommy held Helen’s mink coat for me to put on. It looked and felt so elegant! After he shrugged on his new Burberry coat, he escorted me out the door and into his Porsche. The leather seats felt cold through my stockings, until I was able to tuck my fur under my legs, and the heater kicked in almost instantly. For the next hour and a half, we enjoyed a lazy drive down Lakeshore Boulevard, over the river to see the tree in Millennium Park, and back down Michigan Avenue, taking in all the beautiful Christmas lights like two tourists on their first night in the big city.

When we got back home, after I gratefully stepped out of my heels and Tommy put away my mink, I puttered around the kitchen in my stocking feet, taking another of Helen’s signature dishes out of the oven (beef bourguignon this time) while Tommy opened the wine and set the dining room table. We clinked our glasses and toasted each other this time, still slightly amazed by all of the changes to our lives, and full of hope about the unknown adventures that lay ahead.

The girls had baked some of Helen’s famous Christmas cookies, and I was nibbling on one after dinner when Tommy surprised me with a gift, beautifully wrapped in a tiny box. My heart was pounding while my fingers carefully removed the bow, ribbon and wrapping paper, to reveal a jewelry box from Tiffany. Inside was the most gorgeous engagement ring I have ever seen. “Oh Tommy, I can’t believe you did this!” Tears were flowing down my cheeks.

He dabbed them off with his napkin. “Jeanne, I love you madly. I don’t know where this is going, but I do know that I want to spend the rest of my life with you.” He slipped the ring on my finger, and suddenly I felt complete. “I’m not asking you to marry me or anything like that….” he added uncertainly.

“When you do, when we both know that the time is right, you know my answer will be yes.”

* * *

When we entered the bedroom, one more surprise was waiting for me, only this one wasn’t wrapped: a sinful babydoll nightie was draped over my pillow. I felt Tommy unfastening the clasp behind my back and slowly lowering the zipper on my dress, and then he started to undress me. I left my stockings on after I slithered into my new nightie, and as soon as I’d gotten his clothes off of him, we were going at it once again. “Want to try something new?” he whispered as he nuzzled my ear.

“I didn’t know there were any positions left.”

He rolled me over on my tummy and raised the back of my nightie. Then he grabbed my butt and sort of lifted me up onto my knees, and before I knew it, he was inside me once again. I gasped as his long, hot penis drilled all the way into me and struck home on my prostate. At the same time, he reached around and grasped my own penis, which was quickly reaching the point of no return. The combined feelings of him thrusting back and forth inside me, and his hand sliding up and down my quivering manhood, were so intense that I came before he did, and when he felt my sphincter contracting to the beat of my orgasm, he too went over the edge, and he came inside me with a groan of delight.

We lay there panting in post orgasmic bliss. “What do you call that position?” I asked with a sigh.

“That was doggie style.” He sat up with a start. “Oh no! I left Archie out again!”

* * *

Christmas morning, Tommy made slow, sweet love to me under the covers before he slipped out of bed to take a shower and get dressed. By the time he was done, I’d carefully placed my wig, ring and earrings (and my new nightie) into Jeanne’s suitcase, and in no time I’d scrubbed off the last remnants of my makeup and transformed myself back into Gene. After a close inspection of my earlobes, I dabbed a touch of makeup on each to conceal the telltale holes.

I carried my suitcase downstairs to find Tommy monkeying with the computer in the family room. Now Tommy is a computer wizard, and he’d figured out how to hook both of my daughters and their families into one Zoom call. It was just after 8:00 in the morning in Chicago, so 9:00 for the girls, whose children had undoubtedly gotten them up hours ago. After Tommy patched everybody in, I wished them all a Merry Christmas, and listened to some excited babbling from my grandchildren before they ran off to play with their new toys, I told my daughters that I had a surprise for them. I got out of the chair in front of the computer monitor, and Tommy took center stage.

“Uncle Tommy! I thought you lived in Florida,” Laura cried.

“Merry Christmas, girls. I decided to see if the winter in Chicago was as bad as I remembered, and your Dad put me up for a few days.”

“That’s so nice,” Carolyn piped in. They went on for a few minutes, asking how everyone had been, and at some point one of them mentioned Helen, and there were a few sad words about how much everyone missed her before Tommy gave the chair back to me.

“Uncle Tommy is heading back to Florida today so he won’t get buried by the next blizzard. He’s invited me to drive down with him and spend a few days thawing out.”

“That’s very cool,” Laura said. “I’m glad you’ll have some company, Daddy-O.”

“Yeah, can we come along?” Carolyn joked. “It’s supposed to snow here too.”

“Sooner or later, you’ll all wind up in Florida,” Tommy said from off-camera. The girls and their husbands all laughed, and after a few more minutes we all said our goodbyes and Happy New Years.

“I’m so glad that went well,” I said after Tommy disconnected the call. “I was a little afraid they’d react badly about my going to Florida instead of visiting them.”

“You and Helen raised two fantastic young women,” Tommy assured me. “They’re both preoccupied with their own broods, and I’m sure they’re just relieved that their father isn’t sitting around the house feeling sorry for himself.”

We hit the road after a quick breakfast – it felt weird interacting with Tommy as a guy again, and although for him there seemed to be very little difference between Jeanne and Gene, for me the mad attraction I felt for him as Jeanne cooled down to friendship now that I was back to being Gene. Archie sat on my lap as Tommy maneuvered quickly through the quiet city streets, and soon we were racing south on the freeway. Tommy assured me that the cops wouldn’t be looking for speeders on Christmas, we took turns behind the wheel, and after a long day we pulled into Tommy’s driveway well past nightfall.

“Before I left, I put some takeout in the freezer. By the time you’re Jeanne again, a glass of wine will be waiting for you.”

* * *

It didn’t take me long to duck into the shower, run a razor over my face, and retrieve a wig and makeup from Jeanne’s suitcase. There were a few outfits that I hadn’t worn for Tommy before – one of them was a simple black sundress with yarn bows on the shoulders, and in no time I was dressed and ready for dinner with my fiancé — it seemed so wonderfully strange to say that word! I took an extra moment to put on my ring (I’d felt naked without it) and some simple earrings before I admired the finished product in the mirror. It felt so wonderful to be a woman again!

Tommy was waiting for me in the great room. “Wow, that was quick.” He kissed my lipgloss off my lips, and then he retrieved a bottle of Chardonnay and two glasses from the fridge.

We sat down and sipped our wine in silence. “Something I’ve been thinking about, all the way down here,” I finally said. “You told me that you like me equally well as a girl or a guy. I’m just wondering if you won’t get tired of all the crap I have to put up with to make myself look this way?”

Tommy put down his glass and reached for my hand. “Jeanne, I love you for who you are, and who you are is a woman now, a beautiful woman I’m proud to be seen with. I find all the little feminine things that you do fascinating, and I love how they make you so happy. Every day a new side of you is revealed, like tonight you surprised me by how quickly you could transform yourself, I can’t even imagine how you do that. So if you’re asking me if I’ll ever get tired of you, of being with you, of loving you, I can tell you that’s never going to happen.”

“You always did have a gift for words.” I kissed him and he kissed me back, the kind of kiss a girl never forgets, tender and loving with a hint of urgency. “I’m sorry I brought that up, I guess I’m so in love with you that I’m a little afraid this is all some kind of fantasy. I don’t want to lose you, Tommy, and if that means I have to go back to being Gene, I guess I can give it a try….”

“We both know you’d never be happy that way. You only discovered your love for me after you discovered your inner woman. I don’t think she’s ever going to go away, and if I tried to make her, it would be like killing a beautiful thing. I want you to be happy, and that means I want you to be a woman. And to tell you the truth, watching you getting dressed the other night, the way you put on your stockings, was a real turn-on for me, like I could vicariously experience the joy you were feeling. I don’t ever want that to end.”

* * *

Tommy’s “takeout in the freezer” turned out to be an amazing gourmet meal from one of the best restaurants on 30A, a delicious concoction of pasta and gulf shrimp that was to die for. He’d set a formal table too, and we savored as fine a Christmas dinner as I’ve ever had. It was fun to sit back and watch him do all the work! We’d brought the girls’ Christmas cookies with us from Chicago, and after dinner we munched on them contentedly. “It occurs to me that when we go back to Chicago, we’ll return to a dried up tree, and we’ll have all the lights and ornaments to put away,” I said.

“Ugh. Who says we have to go back?”

“I know. Right now, all I want to do is put 2020 out of my mind, soak up some sun and be your girlfriend.”

“Worthy objectives! Tomorrow we’ll take an early morning walk on the beach, have breakfast at the Doughnut Hole, and drive to the Destin outlets to dress you for Florida.”

“Sounds dreamy.”

We were both exhausted from the long drive, and that night, for the first time since Tommy met Jeanne, we didn’t make love. After I changed into the new nightgown Tommy gave me in Chicago, we spooned under the covers until we fell into a dreamless sleep. It was a little like the last years of my marriage to Helen: even before her fatal illness, we rarely made love, but there was a contentment and a closeness that was in many ways just as intimate.

The next morning dawned gray and foggy, so I passed on the beach walk and let Tommy take Archie for a run while I took a delightful bubble bath, shaved my body once again, put on my wig and makeup and dressed myself in the last unworn outfit in Jeanne’s suitcase, a thin mock turtleneck and an Ann Taylor skirt that I always adored on Helen. By now, I was totally comfortable in my woman’s skin, and I marveled at the way my new breastforms feminized my whole physique. I wondered for the umpteenth time how I’d managed to survive so many years before my secret self surfaced.

Tommy gave me a wolf whistle when I joined him downstairs. “Wow, you’ll be the best dressed woman in Destin.” He picked up his cellphone and snapped a picture. “I want to remember you this way forever.”

* * *

One month later, our lives had fallen into a delightful rut. Up every morning (except for the rare times when it was raining, I slept in those days) for a five mile walk on the beach with Archie, followed by breakfast and coffee on the deck, then either golf (in an Izod skirt, with my new ladies’ clubs) or tennis (in a white tennis dress, with my Maria Sharapova racquet)

followed by a light lunch and, when it was warm enough, a dip in the community pool (in my two piece skirtini) and a siesta under the sun, before we changed into shorts and sandals and did a little shopping or sight-seeing, picked up some takeout from one of our favorite restaurants, and enjoyed a lovely dinner with a bottle of wine. We’d usually cuddle on the coach and stream Netflix or an old movie before we hit the sack, where we made love almost every night, and sometimes the next morning too.

By the end of January, I was deeply tanned, and my tan lines would have made it embarrassing for me to pass as a man if I took my top off. Other than the occasional summer skirt, I hadn’t dressed up or put on nylons in over a month. The rush of erotic excitement from crossdressing had been replaced by a serene contentment with my new life as a woman, and with each passing day, I was more and more certain that I wanted to spend the rest of my life as Tommy’s wife. The hard part would be coming out to my daughters, but the pandemic provided a convenient excuse for us to put that off, and our lives in semi-isolation protected us well from the dreaded Coronavirus.

One day in early February, I was swimming laps in the pool (I limited myself to the breaststroke so as not to wet my wig) when Tommy heard my cellphone ringing in my beach bag. He called me out of the water and told me I’d better take it.

It was my doctor, calling from Chicago. “Good news, Gene, you’re in the queue for the Pfizer vaccine. We can’t schedule you until next week, but I thought you’d want to nail something down, since they’re going fast. Can I put you down for next Tuesday at ten o’clock?”

What could I say? Of course I wanted the vaccine, as soon as possible, and without thinking about the ramifications, I told him yes, by all means. After I hung up, I began to think about all that this would mean. “We have to go back to Chicago,” I said to Tommy. “I’m scheduled for a vaccination against the Coronavirus next Tuesday.”

“That’s great! We can head up over the weekend.”

“Tommy, what about you? What if it’s time for your vaccination and you’re up in Chicago?”

“Then I’ll drive back and take it. That’s the reason I decided to retire to the panhandle, it’s a one day’s drive from Chicago.”

“I guess this means life will go back to normal soon. Except for us, normal isn’t exactly normal….”

“Are you thinking about your daughters?”

“Yes. As soon as this is behind us, they’re going to expect me to come visit them, or they might want to come to Chicago. Tommy, I don’t want to hurt them, but I don’t want to lie to them either. And if I turn myself back into Gene, even if it’s only for a few days, I’ll be living a lie. I’m a woman now, and I can never go back to being a guy.”

“Then don’t. We’ll face them together, with my ring on your finger. I’ve been thinking about this a lot. Your oldest grandchild is three years old, too young to really remember Helen. Let’s be Grandma and Grandpa, you and me.”

“That’s crazy!”

“Maybe, but no more crazy than their grandfather deciding he wants to become a woman. It’ll be a lot easier for them to accept us as their grandparents.”

“What about Laura and Carolyn? And their husbands?”

“It may be a tough sell, but we won’t know until we start working on them. I’m betting they’ll come around. It won’t be easy, but they love you and they want you to be happy. Give them a little time to get over the shock, let them get to know the new you, and they might go along with it.”

“And if they think we’re both loco?”

“Then your grandchildren will grow up being told that Grandpa is a weirdo, at least for a while…our society is changing at warp speed, and by the time they’re old enough to understand, a trans grandparent may be almost commonplace.”

“I don’t know…I’m just afraid that Laura and Carolyn are going to freak out.”

“If they do, we’ll always have each other, till death do us part. But let’s at least give them a chance. After all, what do we have to lose?”

“Only the love of my family, for the rest of my life! Maybe I should just switch back to Grandpa, it’s only for a little while….”

“Sweetheart, that’s a decision only you can make. You know I’ll love you either way. In the immortal words of Yogi Berra, ‘When you come to a fork in the road, take it!'”

* * *

I spent the next few days scouring the web for articles about “how to tell your children that you are trans.” Actually, most of the advice I found was about how adult children can explain to their parents that their grandson wants to be a girl (or vice versa) but as I drilled down into the websites I found some helpful tips:

“If your children have never met a gay or lesbian person, if your children have never seen a trans man or trans woman” (in other words, if your children have been living in a cave on a desert island without a computer, television or radio for the past thirty years) “then I strongly advise you against coming out to your children.”

“When it comes to delivering shocking or potentially destabilizing news to anyone…frame the news not as a statement, but as a question.” What a great idea: “Kids, how would like to see your father in dresses and high heels for the rest of his life?”

“Many families saw a parent’s transition as an asset—that this unique life trajectory contributed to a richer family story.” Just imagine how riveting the insert accompanying next year’s Christmas card will be!

“Give them the weekend to be confused. Don’t do things like tell them at Thanksgiving dinner.” Thank God the Holidays are over.

“If you’ve done too good of a job ‘hiding’ your identity, your child will be even more shocked with the news, and may wonder if there is anything else about their relationship with you that is going to change.” Yes, guess what: I’m going to marry Uncle Tommy!

“It’s a great idea to encourage the child to seek therapy.” If I follow all this advice, they’ll be in therapy for the rest of their lives.

When I shared this nonsense with Tommy, he told me, “You know Laura and Carolyn better than anyone in the world, and certainly better than some crackpot spouting off on the Internet. You’ll figure out the best way to tell them. Why don’t you try writing down your thoughts? If you’d like, I’ll be glad to take a look at it. Who knows, it might be best for you to break the news to them in a letter or an email?”

The more I wrestled with it, the more I began to think that Tommy might be right. The last thing we needed was a face-to-face reveal that might very well blow up when the girls saw their father dressed as a woman. During the long drive back to Chicago, I started to assemble my thoughts. I hated every minute of that drive, being stuck as a man once again, and as soon as we got back to my townhouse late that night, I put on my old wig and a nightgown before we collapsed into bed.

It felt wonderful dressing myself as a woman the next morning, in a skirt, sweater and tights, before we tackled the miserable job of boxing up all of the Christmas tchotchke and throwing the husk that remained of the tree out onto the curb. After we restocked the fridge and I sorted through six weeks of mail, I sat down in front of the computer and started to write a letter to my daughters:

Dear Laura and Carolyn,

First, some good news: I’m scheduled to have my first Coronavirus vaccination this week, and by the end of the month I should be fully immunized. I cant wait to see you and your families again!

Now for some difficult news, not bad news, but news which I’m sure is going to surprise you. After your mother passed away, when I started to clear her old clothes out of the closet, I felt a strange compulsion to try on one of her skirts. During all our thirty years of marriage, I never once had these feelings, and the only other time I ever tried anything like that was when I was 10 or 11 years old and your grandparents were out of town, I dressed up in some of your aunt’s clothes but I never did it again, and nobody ever knew.

I don’t know how to explain this to you because I can’t understand it myself, but before that day was over I’d shaved my legs, put on some of your mothers old lingerie and stockings, as well as her wig and some makeup, and when I finally dressed myself in that skirt and one of her tops, it was as if I’d been transformed into a completely different person. The closest thing to it that I can think about is the Hindu belief in the transmigration of souls, only I didn’t die and come back as a woman, I discovered that I have the ability to transform myself into a woman – a woman named Jeanne. I’m sure this comes as a complete shock to you, and I’m telling you this way because I want to give it some time to sink in before we see each other again. I’m attaching a photo to show you that this is really happening.

The next time we see each other, I’ll be Jeanne. I’ve been living full time as a woman for some time now, and I don’t think I can ever go back to being a man. I love you with all my heart, and I hope and pray that you and your families will find it in your hearts to let me stay a part of your lives.



I printed out a draft and showed it to Tommy. The photo I attached was the one he took of me the day after we returned to Florida, when he told me, “I want to remember you this way forever.” After he read it, he asked the obvious question: “Why didn’t you tell them about us?”

“Maybe I should. I just figured one shock would be enough for a start. When we see them again, I want you to be with me. I guess I’m not being very strong….” I started to cry.

Tommy took me into his arms and hugged me. “Jeanne, the very fact that you’re telling them shows more courage than I’ve ever seen. If you want to start with baby steps, you know them best. Besides, once they think about it, and realize that you’ve been staying with me in Florida, they’ll put two and two together pretty quickly.”

“Do you really think so.”

“I know so. Even if I’m wrong, once we get together and they see that rock on your finger, they’ll figure it out.”

“I love you, Tommy.”

“And I love you Jeanne, now and forever.”

“I’m going to send this to them right now, before I change my mind.” I attached the letter to an email addressed to Laura and Carolyn, and pressed send.