The Road Ahead

The Road Ahead

© 2020 by Nom de Plume

One day...two days...three days went by without a reply from my daughters. At first I checked my email every few minutes to see if there was any response from them, but as the hours turned into days, I began to despair that I would ever hear from them again. Tommy tried his best to keep my spirits up, but by the third day I was inconsolable, and I spent hours alone in the bedroom, sifting through old family photographs from the days when the girls were growing up, childish artwork that they brought home from school, albums and souvenirs featuring their college graduations and weddings, and touching mementos of the birth of our grandchildren. Each time I saw Helen's radiant smile in an old photo, I felt more and more ashamed of the person I had become, and I cursed my stupidity for taking my daughters' love for granted, and throwing away their memories of me as a father and grandfather.

The only break from my misery came when I put on some of Gene's old clothes to go to the doctor for my vaccination. I put the trainer studs back in my ears, and nobody seemed to notice, or if they did, they didn't say anything. Chicago was still gripped by the pandemic, and the streets were eerily empty, like being in a ghost town, which only added to my depression.

When an email from Laura finally came, I was almost afraid to look at it. Tommy happened to be standing next to me, and he looked over my shoulder as we read it together:

"Daddy,

Carolyn and I would like to see you in Chicago on Saturday. We can stay at a hotel. To say that your email came as a surprise would be an understatement. We have a lot of questions! We both love you and we want to help you if we possibly can,

Laura"

"Looks like they want to stage an intervention," Tommy observed.

"At least she said they still love me," I sniffed.

"Of course they love you! It sounds like they don't want to lose their father...."

"It sure does. Tommy, what should I do?"

"Let's not reply to them right away. They obviously spent the last three days talking it over, trying to figure out how to handle you...let's just think about this, and sleep on it overnight, okay?"

* * *

I tossed and turned all night, as Tommy and I spent hours going over every possible scenario. Did I want to tell them the whole thing was a giant mistake, and I'd come to my senses? That would be the easy way out, but did I really want to go back to being a man, and try to love Tommy that way? Could I ever live without him? What if my daughters decided to cut me out of their lives completely? What was more important, my family or my desire to live as a woman? After a restless night, I came up with a plan....

The next morning, after coffee and a croissant in my robe, nightgown and slippers, I tapped out this reply to Laura before I got dressed:

"I'd love to see you and Carolyn on Saturday. No need to get a hotel room, you can stay in the guest room. Try to get here in time for dinner, we have lots to talk about."

"Well played," Tommy said. After our all-night bull session, we'd decided that it would be best for him to head back to Florida before the girls arrived. He was reluctant to leave at first, but I explained that this was first and foremost about me and my daughters, and if he were there, they'd immediately assume that he was the one who'd put the idea of living as a woman into my head. I told him I'd drive back down to Florida, one way or another, as soon as the girls left Chicago.

I wasn't about to send him off without giving him a night to remember. I'd been slouching around the house for the past three days in sweaters and leggings, and I needed to feel like a woman again. First I luxuriated in the tub, shaving my body from head to toe. After I smoothed French moisturizer all over, I took my time getting my makeup just right, brushed and fluffed my wig just so, and slipped into a bra, panties, garterbelt and stockings, the old-fashioned kind, along with a lacy full slip and my beloved breastforms. Then I slithered into a new dress, a little black creation that fell just to my knees. I stepped into those super high heels again, put on my diamond earrings and a matching pendant that Tommy had surprised me with, and after I finished myself off with a few sprays of Obsession, I waltzed down the stairs to find Tommy waiting for me with a cocktail shaker and two highball glasses. He poured us each a whisky sour, we sat down on the sofa, and our conversation turned once again to my expected confrontation with my daughters.

"Are you still planning to meet them as Daddy?" he asked.

"Yes, although I certainly don't feel like a Daddy right now."

"You don't look like one either." We kissed, and his hand slid up my leg, caressing my silky knee before it came to rest at the top of one of my stockings. "How did you ever manage to put these on? They must be a pain...."

"I guess I'm making up for lost time. I think a lot of women my age have spent so many years getting gussied up in dresses, heels and stockings that they're sick of them, and just want to be comfortable. For me, it's all still new and exciting, although I have to say that I was happy spending every day in Florida in shorts and sandals. For some reason, when I'm in the big city I feel like dressing up. The past few days, as I was going through my mini-identity crisis about whether I really wanted to go back to being a man to appease my daughters, I felt like a fish out of water."

"You almost make it sound like turning yourself back into Gene tomorrow will be like crossdressing for you."

"Exactly, it will be! But it's all part of the plan, remember?"

"Let's talk about something else. The way you look right now, it's impossible for me to think of you as a man." He kissed me again, and we went into the kitchen to work on dinner.

* * *

Tommy and I hadn't made love since I reached out to my daughters, but that night we went at it like there was no tomorrow. You might think that my love for him would have cooled after the sobering reply from Laura, but if anything our relationship grew stronger with the realization that we might be the only two people in the world who truly loved and understood each other. "Got any new positions for us to try?" I asked him after I stepped out my dress and slip and changed into a coquettish black nightgown. My stockings were still on my legs, and Tommy slid his hands up and down them as he pondered my question.

"Hmmm...turn around, that's right, now sit down on me."

I did as I was told, and as he slowly impaled me, I almost turned around - looking at his feet wasn't my idea of intimacy - until his penis made a beeline for my prostate. "Oh!" I cried out as the most intensely pleasurable feeling I have ever experienced swept through me, an indescribable delight, sweet waves of impure lust, and as Tommy groaned with the approach of his orgasm, I looked down with astonishment at my own penis, which was pulsing out semen without any assistance from my hands. The feeling of Tommy's climax deep inside me triggered a second wave of ecstasy, almost like the multiple orgasms that women can experience, and I rocked back and forth on my haunches, savoring every last drop of Tommy's jism, until he finally started to soften and we collapsed into each other's arms. "What do you call that one?"

"That's the reverse cowgirl. For some reason, our bodies fit together just right."

"Yippee ki-yay, father fucker!" I sighed, and Tommy laughed until he cried.

* * *

By the time Tommy and Archie left on Saturday, I was well and truly sated, and I took my time cleaning up the house in a skirt, sweater and tights before a glance at my watch confirmed that it was time to turn myself into Daddy. Laura had acknowledged my reply with a quick email informing me that she and Carolyn would arrive in time for dinner, so after I took the last of the meals they'd prepared out of the freezer, I sadly hung up my skirt and sweater, peeled off my tights and lingerie, removed my wig, makeup and jewelry and took a long, hot shower. After I dressed myself in khakis and a crew neck sweater - with a few surprises underneath that will be explained later - I took special care to strategically organize the items I'd need to return to my female identity before I went downstairs, set the table for three, put the dinner in the oven and dived back into the Internet for tips about coming out as trans to one's adult children. But there was nothing really new or helpful, and when I heard the doorbell ring, I knew that I was totally on my own, with my family's future and my own chances of happiness riding on the outcome of the next few hours.

I opened the front door. Laura and Carolyn seemed stunned to see their father looking just as they remembered him. After a moment's hesitation, they ran into my waiting arms and I hugged them both, as if the pandemic didn't exist. Eventually, they picked up their suitcases and I let them carry them up to the guest room. The door to my master bedroom was tightly shut. I waited for them to come back downstairs, trying unsuccessfully to make out their hushed whispers as they obviously tried to figure out why I wasn't dressed as a woman. When we finally all sat down in the living room, there was an awkward silence before Carolyn finally broke the ice. "We were expecting you to look a little different," she said.

"I'll bet. My email must have come as quite a shock."

"And then some," Laura broke in. "Daddy, please tell us what's going on?"

"First, I want you both to know that you mean the world to me, and I hated the idea of upsetting you. I was hopeful that we could discuss this calmly, as difficult as it must be for you to understand, but when I didn't hear back from you for days, I realized I'd made a mistake."

Momentarily thrown on the defensive, Laura quickly recovered. "You mean you made a mistake about...wanting to dress up as a woman?"

"No, everything I told you is true." They both sagged. "But I didn't want my appearance to make you uncomfortable before we have a chance to talk this through."

"Why are you doing this?" Carolyn asked.

"I wish I knew, Carrie" (that's what I always called her) "my whole life, there must have been a woman living deep inside me, and when your mother died, she decided to come out...."

"You're talking about this Jeanne person," Laura said. "Daddy, have you seen a psychiatrist?"

"No, Laura, I haven't. Maybe I should. But I'm not planning to take any drastic action that would require a medical opinion - I'm not on hormones, and I don't intend to have any operations."

"So you just like to dress up in Mom's old clothes around the house? I thought we got rid of all them, anyway."

Now we were entering onto shaky ground. "It was that way in the beginning. Before you got here in December, I'd already discovered this about myself, but I was careful to keep it from you, and I hid some of your mother's things in the attic before you got here."

"Daddy, why didn't you tell us?" Carolyn demanded.

"Isn't it obvious? I was afraid of how you'd react. When I sent you that email, I was hoping it would start a dialogue between us that could lead to some understanding. Then, when I never heard back from you...."

Laura cut me off. "Where's Uncle Tommy? Did he have anything to do with this?"

"Good Lord no. Uncle Tommy is in Florida."

"You told us you've been living as a woman for a long time. Weren't you down in Florida with him?" she asked accusingly.

I'd been expecting this, and I answered her honestly - up to a point. "Yes. When I told him about Jeanne, he was astonished."

"So what happened."

"I asked him if he'd like to meet Jeanne, and he said okay."

"So you dressed up as a girl for him?"

"No, I dressed up for myself. He was surprised at first, but he tried to understand."

There was a telling silence. Finally, Laura shifted to the next point on their rehearsed agenda. "Daddy, this isn't just about us not understanding you. We each have families, young children who think they have a grandfather. We haven't even discussed this with our husbands, because we don't know how they'd react, or their families, or our friends...."

"Don't you think you're being a little selfish?" Carolyn piled on. "I mean, if you want to do something kinky like dressing up in women's clothes, why drag us into it? We're not going to try to stop you, but you can't expect to just waltz into our lives and spend time with our families in drag...."

"Not to mention the risks you're taking," Laura added. "Aren't you afraid about what might happen if somebody takes you the wrong way when you're out and about? You don't know anything about being a woman, but there are a lot of sickos out there."

"We're so worried about you!" Carolyn blurted out. "What would Mommy think?"

"We think you should get some professional help," Laura pronounced with finality.

I stood up. "Girls, I think it's time for a break, don't you? Dinner's in the oven. I'll be down in a few minutes." With that, I turned my back on them and headed up the stairs.

* * *

As soon as I closed the bedroom door behind me, I went straight into the routine that I'd choreographed in my mind the night before. First, I tore off my sweater, khakis and sox to reveal the bra, panties and pantyhose that I'd been wearing underneath. After I stuffed my breastforms into my bra, I sprinted into the bathroom and went to work on my makeup: foundation, brow pencil, eyeliner, shadow, a touch of mascara, a bit of blush and a swipe of lipstick later, I was in my wig and on my way back into the bedroom to slip into the skirt and top that were waiting for me on the bed. After I stepped into a pair of flats, I took a moment to put on earrings and a necklace, gave myself a spritz of cologne, and after a quick look in the mirror, I was on my way back downstairs to face the girls as Jeanne.

Carolyn saw me first, and I could tell from the confused look on her face that she didn't recognize me at first. "Daddy?" she asked uncertainty.

Laura spun around and greeted me with the same shocked expression. "Oh my God, is that really you," she said.

"Yes, it's really me," I said as I took a bottle of Zinfandel out of the wine rack and unscrewed the cork. "Let's sit down for a few minutes, I have some explaining to do." I filled three glasses, and they followed me back into the living room as if in a trance.

"Girls," I began, "I wanted to greet you as your father, because I knew you had a lot on your minds and I didn't want my appearance to get in the way. I've listened carefully to everything you said, and all of your questions and concerns are totally understandable. Now it's my turn to talk, and I hope you'll listen while I try to explain the unexplainable.

"I honestly don't know why I want to be a woman. I think I told you in my email that a long, long time ago when I was very young, I dressed myself up in my sister's clothing, and I loved every minute of it. But I never did that again, and once I met your mother, and fell in love with her, crossdressing was the farthest thing from my mind. It wasn't until after she died that a strange compulsion came over me, one thing led to another, and after some trial and error I figured out how to make myself look this way. It's all come very naturally to me, and I know I'm lucky that I'm not bulked up like most men, or this would be much harder, although even then I don't think I could ever stop. I know I'm passable as a woman, because over the past two and a half months I've been doing just that, and I love everything about it. I've gone from being a lonely old man to an attractive mature woman, and I don't ever want to go back."

I took a long pull from my wine glass, and I could see that my daughters' glasses were almost empty, so I walked into the kitchen and returned with the bottle. After I refilled their glasses, I returned to my chair and sat back down, smoothing my skirt and crossing my legs. The girls' eyes were glued on me the whole time.

"Now let me tell you about your Uncle Tommy. He's gay. Believe it or not, I never knew this about him, although your mother suspected it all along. Anyway, after she died, he invited me to come stay with him in Florida, and as I told you, I surprised him by dressing up like this. Uncle Tommy and I have been friends since third grade. He's been all over the world, and seen just about everything, and I needed someone I could confide in. He couldn't believe it when I told him at first, but since I started dressing like this full time, he's been very supportive." That was as far as I intended to go, for now....

The girls were staring at me in stunned silence. "I can't expect you to understand any of this, but I hope that, in time, you'll try to let me back into your lives. I know it will be terribly difficult to explain to your husbands, as well as their families and your friends, and if I thought it would help, I'd be happy to tell them myself, although I get the impression that you'd rather I stay away for the time being.

"Fortunately, your children are too young to understand any of this, but sooner or later, they'll have to be told. I hope you'll let me see them again. I'm not the only trans person in the world, and our society is becoming much more accepting, but I'd be kidding myself if I told you this is going to be easy. I'm truly sorry for all the hurt this has caused you.

"What I'm trying to say is that despite all the pain, the person you see is the person I want to be. I'm not insane, and I'm not going to stay in the closet to avoid embarrassing you. I hope and pray that someday you'll understand.

"Let's talk some more over dinner." I got up, and my daughters followed me into the kitchen. I was hoping that we might engage in small talk as we tossed a salad and served up the casserole, one of Helen's signature recipes, but the girls remained silent as we sat down to eat. I opened another bottle of zin, filled their glasses again, and tried to think of something to say. "This is delicious. It reminds me of your mother."

"Daddy, do you think that you're subconsciously trying to become Mommy in some way?" Carolyn asked.

"I don't think so, Carrie. If anything, I'm ashamed about what she must be thinking if she's looking down on me from Heaven."

"I just don't get it, Daddy," Laura chimed in. "What's so great about being a woman, that you'd want to throw your life away?"

"Well, I'll admit that some of it's a real pain, it's very high maintenance, you don't need me to tell you that. But I love the way I look and feel."

"I just don't get it the whole crossdressing thing."

"I could say that you're crossdressing right now. Both of you, in jeans and sweatshirts. Who says a man can't put on a skirt?"

"Now you're being silly," Carrie said, and for the first time I sensed that her resistance might be weakening.

"Do you remember Archie, Uncle Tommy's dog?"

"Sure, he's a cutie."

"When I dressed this way the first time down in Florida, I was surprised that Archie didn't even notice. Clothes don't matter to dogs, they love unconditionally."

My daughters took this in. "What are we supposed to call you?" Laura asked with resignation.

"Daddy's fine. I know what you're thinking: you lost your mother, and now you're losing your father. I'm still here, under these clothes, and if you insist that I disguise myself as a man when I come to see my grandchildren, of course I'll do as you ask. Only you'll have to come up with a reason why Grandpa got his ears pierced." I flicked back my wig to show off my diamond earrings.

"Those look expensive," Carolyn observed. "Did you hold out on us when you showed us Mommy's jewelry box?"

"Uh, no, these were a gift from Uncle Tommy."

The girls exchanged knowing glances. "What haven't you told us?" Laura asked.