The Road Less Traveled

As I listened to her message, I could feel the blood draining from my face: "Hi Daddy, it's me. We're worried about you! I've decided to drive to Chicago to spend a few days with you and help you clear out Mom's old things. I'm leaving first thing Tuesday morning. Call me when you get this, love you!"

Tommy could tell from the stricken look on my face that something was terribly wrong. "What is it, sweetheart?" he asked.

"That was Laura, calling to inform me that she's worried about me. She's driving to Chicago on Tuesday to make sure I'm okay, and she wants to help me clear out Helen's old clothes."

"So call her back and tell her you're in Florida with me. Of course, you might want to leave out a few details...."

"Very funny. After I blew off her invitation to come for Thanksgiving, I can't very well tell her I decided to go to Florida instead!"

"Point taken. Okay, why not tell her that you're under the weather, and you'll let her know when you're feeling better?"

"Because she'll immediately assume that I have Covid-19, and then she'll really be worried. I can't do that to her."

"Another good point. So just tell her that there was a major blizzard, the roads might still be a mess, and you don't want her driving all the way to Illinois alone?"

"That might buy us some time...."

"Only don't call her, send her a text instead. I don't think you're a very good liar."

"I'll take that as a compliment." I tapped out the following text on my cellphone: "Just got your voicemail. I would love 2 see u but I am worried about u driving all that way alone. We just had a big snowstorm and the roads may be a mess."

A waitress materialized and bantered back and forth with Tommy. "Who's the lucky lady, and where have you been hiding her?"

"Bonnie, meet Jeanne. Jeanne and I were high school sweethearts, and we're rekindling our old romance."

This sparked a little flame in my panties. "Hi Bonnie." It occurred to me that this was my first conversation as Jeanne with another woman, and I hoped that she wouldn't see right through me. "Am I taking Tommy away from you?"

She laughed. "My husband and three kids might stand in his way. What can I get you two lovebirds to drink?"

"How about a Cosmo?" The ultimate girlie drink, and I'd never had one. No time like the present!

"And a vodka tonic for me," Tommy said.

Just then my cellphone buzzed again, only this time it was a return text from Laura. My heart sank when I read it: "Just talked to Carolyn. Will pick her up and drive together. See u Tuesday😊"

Tommy waited until Bonnie left to get our drinks. "What now?" he asked.

"We're fucked. Now both of my daughters are coming to Chicago. Laura is going to pick up Carolyn in Philly and they'll make the drive together. Got any more bright ideas?"

"What about their kids? Don't tell me they're bringing them along too?"

"Both of their husbands are working from home these days, so I'm sure they'll be stuck watching them." Bonnie returned with our cocktails, and I took an unladylike pull on my Cosmo after she left us with our menus. "What a buzzkill!"

Tommy sat there in silence for a long time. When he finally spoke, his advice was crisp and clear. "So let them come. You can drive back tomorrow and you'll be Gene when they get there. Let them have a field day in your closet. It's time you started getting your own clothes anyway."

"Do you really think so?"

"Of course I do. As soon as they're gone, let me know, and I'll drive up to spend the holidays with you. I haven't had a white Christmas in years. Only leave Jeanne's suitcase with everything you brought down here. I'll bring it back with me so you won't have to start from scratch."

* * *

That night, knowing that I'd be turning back into a man the next morning, we made love with an intensity that surprised both of us. After Tommy had an orgasm deep inside me - there was a lot less pain and even more pleasure this time - he went down on me and treated me to my first blowjob in over thirty years (Helen confessed on our honeymoon that she hated them) which was sheer, unadulterated bliss for me, and Tommy seemed to enjoy it as well, so after we cuddled for a while and built up a little steam, I tried going down on him, which wasn't half bad for me, and absolutely drove him wild. It took him a long time to climax, and when he did, I felt an indescribable power over him, and by then I was getting hard again too, and he tenderly fondled my penis while he kissed me all over, until I finally came with an incredible rush in his hand.

We were able to grab a few hours sleep, and I was up before dawn. I slipped out of bed, careful so as not to wake him, and quietly packed Jeanne's suitcase, adding my wig and makeup before I snapped it shut. I took a quick shower in the guest bathroom, and I'd transformed myself back into Gene before Tommy woke up to see me off. We finished off the pastries from the Doughnut Hole with coffee while we sat there looking contentedly into each other's eyes. "Do you still find me attractive this way?" I had to ask him.

"Totally. How about you?"

"I'll be honest, now that I'm a guy again, I think of you as more like a friend. I hope you don't take that the wrong way...."

He shook my hand. "Just make sure you're a girl again the next time I see you."

* * *

Four days later, I bid my daughters a tearful farewell before they started their drive back east. It had been a wonderful visit, as we laughed and cried over happy memories of my wife and their mother. The girls attacked her closet and dresser like brides in Filene's Basement, although what they didn't know was that before they got there late Tuesday afternoon, I'd stashed away some boxes in the attic, containing a few select items including winter skirts and dresses, boots, and most important, a full length mink that I'd surprised my wife with on our last Christmas together, shortly before she was diagnosed with brain cancer. We never told the girls about it, since both of them thought wearing fur was borderline criminal, and I was certain that neither one of them would have wanted it. They kept Helen's old wedding dress, and split up her expensive watches and jewelry, before they helped me haul everything else to the thrift store operated by our church.

Each of them asked me if I wanted to visit them for Christmas, but I assured them that with the pandemic still raging, I had no intention of getting on an airplane, and the Chicago winter made driving a dicey proposition. It helped that another blizzard was bearing down on us, expected to arrive over the weekend, so they were up early on Friday for the long drive back to their respective homes.

As soon as they were safely gone, I retrieved from the attic the items which I'd stashed there. Two packages from Amazon, for the wig and makeup that I'd ordered one night after they both turned in, were due to arrive that afternoon, so I spent the morning hauling the Christmas decorations down from the attic and picking up a wreath and a live tree from a nearby lot. By the time I'd finished with all the tasks that Gene used to do - setting up the tree in the stand, wrapping it with strands of white and colored lights, putting the star on top and the wreath on the door - my Amazon packages had arrived, and it was time to turn myself back into a woman before Tommy arrived that evening.

One other package had also arrived, a mystery! When I opened the outer box, I saw that it was from Tommy, and a note on the box inside said "Open Before Christmas" so I did, to find a pair of silicone breastforms, teardrop shaped with very realistic nipples! There was another note inside the box, in Tommy's handwriting: "You said you wanted boobs, here they are!" What a guy!

Of course I began once again with a long, lovely bubble bath, where I shaved my body before I heated up the water some more and luxuriated in the suds while I dreamed about the delights that I'd planned for the days and nights to come. After I dried myself off, moisturized all over and put on one of Helen's old bathrobes (I'd spent hours during the long drive back to Chicago making a mental checklist of all of her things that I'd need to start living full time as a woman) I applied my new makeup and put on my new wig, which was identical to the one I'd left behind in Florida. I knew that Tommy would be bringing it with him, but his last words to me had been, "Just make sure you're a girl again the next time I see you," and I wasn't about to disappoint him!

The dress I'd salvaged to wear that evening was a knit creation in winter white, with black and pink stripes across the bodice and a cute little belt to accentuate my girlish waist. I'd also saved a white slip and teddy to wear underneath, along with a pair of sheer nude pantyhose. Once again, I had to struggle against my rising libido while I eased the silky hose up my freshly shaved legs, although the teddy helped to hold my bewildered penis between my legs after I smoothed everything into place. After I inserted my new breastforms into the teddy's cups, which filled them out beautifully, I slid my dress carefully over my head to make sure I didn't get makeup on the collar, strapped on my little belt, and carefully stepped into the highest pair of heels I'd found in the closet - it was hard at first to walk in them, and they pinched my toes! But I loved the way they looked with my dress, and the way they shaped my legs, and I practiced walking around in them until I started to get the hang of it. My new bosom didn't take any getting used to, I loved having a rack and they felt amazingly realistic when I squeezed them through my dress.

After I put on some jewelry, I glanced at my woman's watch and figured I had about two hours before Tommy arrived. Mincing carefully in my heels, I first went into the kitchen and put a casserole into the oven - over the past three days, my daughters had recreated many of Helen's favorite recipes for me to survive on over the Holidays. Tonight it would be beef stroganoff, with a bottle of Pinot Noir that I opened to breathe before I quickly set the dining room table with Christmas napkins, china and silverware.

Then it was back to the living room, where I threw myself into Helen's old holiday tasks: I put battery-operated candles in all the front windows, placed Christmas candles around the living room, tacked some garland over the mantle for our gas fireplace, hung the Christmas stockings, and carefully unwrapped and placed a lifetime of Christmas ornaments on the tree. Each one of them reminded me of Helen, and I shed a few tears as I remembered our wonderful family Christmases when the girls were growing up...but life goes on, I reminded myself, and now I had the opportunity to make Christmas special for a special man, a man who'd been waiting for me all of his life. I dried my tears, and after I put the last ornament on the tree, I got a hammer out of the kitchen junk drawer and nailed something in the archway above the foyer.

Done! I collapsed into an upholstered club chair and looked around the living room with pride and satisfaction. You could be a pretty good homemaker, I said to myself...the stroganoff in the oven smelled delicious, and I sat back contentedly to wait for the doorbell to ring.

Tommy and Archie were right on time! When I opened the door, Archie bounded into the living room while Tommy gave me a double-take. "My God, how did you manage that?" he asked. He was holding Jeanne's suitcase in one hand and his in the other.

"Manage what?" I asked innocently, closing the front door.

"Manage turning yourself back into Jeanne, I thought...I mean...."

"A woman has to have her secrets," I said as I led him under the object that I'd hung in the archway. "Oh look, you're under the mistletoe. I think that means you have to kiss me." Thanks to my high heels, our lips met perfectly, and we fell into a long, lovely kiss that melted both of our hearts.

"I see you put on your presents," he said, tenderly caressing my breasts.

"I love them! Merry Christmas, Tommy."

"Merry Christmas, Jeanne." Our eyes were level too, and he looked into them and smiled. "What are you doing New Year's Eve?"