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?"

"Wiseguy!"

"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.