The Road Ahead

* * *

We talked until midnight, about everything. When they finally turned in, I collapsed on my bed and glanced at my cellphone to find a text from Tommy. "Made it home. Call when u can."

The text was fairly recent, so I risked waking him up. He answered on the first ring. "How did it go?"

"It was hard at first, very rough."

"Did you stick to the script?"

"I did at first. Greeted them as Daddy, and you were right, it was like an intervention. I waited until they hit me with both barrels, and then I excused myself and when I came back downstairs ten minutes later - I timed myself, not bad - I was Jeanne"

"How did they react?"

"How do you think? They both went into shock. So I poured us each a huge glass of zin, and they listened while I tried to explain."

"And how did that go?"

"Like I said, very rough. We finally sat down to dinner, we had another bottle of zin, and as the evening progressed we started to understand each other. They're no longer recommending that I see a shrink, and I've given up on the idea of presenting myself to their friends and family as Grandpa in drag, as Carolyn put it."

"So, progress. Did you tell them about us?"

"Eventually."

"And?"

"It was girl talk, Tommy. I wasn't exactly explicit, but I think they got the idea."

"I'm glad I wasn't there."

"At least we made a start. They know that I'll be living the rest of my life as a woman, and they have a pretty good idea that I'm in love with you."

"Wow. You did go off script."

"Blame it on the second bottle of wine."

"So what happens next?"

"We'll have breakfast downstairs tomorrow, we girls will, and I'll probably have to re-plow some of the same ground again, but as somebody once said, once the toothpaste is out of the tube, you can't put it back."

"Sufficient unto today is the evil thereof."

"Yep. There's a long road ahead, but there's no turning back now."

"I'm proud of you Jeanne, and I love you to death. When can I see you again?"

"As soon as they clear out tomorrow, I'll be right behind them, on my way back to sunny Florida. Only this time I'll make the drive as a woman."

* * *

I was up early on Sunday morning, wanting to be packed and ready to drive to Florida as soon as my daughters were on their way home. It was cold and gray outside, a typical winter day in Chicago, and I decided to go with pants instead of a skirt, since I'd be stopping at restrooms along the way, and I didn't want to have to cope with lifting up my skirt over a public toilet. A tunic top with a belted waist, knee high stockings and flats completed my travel ensemble.

I beat the girls to the kitchen, and by the time they came downstairs, coffee was perking, toast was in the toaster and scrambled eggs were ready to ladle onto the plates. "Wow," Carolyn said, "I can't ever remember you in the kitchen when we were growing up. Now you're like Suzy Homemaker."

"That's what Tommy calls me too," I smiled.

"Wait, what? Are you cooking breakfast for him these days?" Laura asked. "Just what goes on between you two?"

I ignored the question as I buttered the toast. "Breakfast is served," I said cheerfully. "Who wants coffee?"

"You know Daddy, it's impossible for me to think of you as a woman, but I must admit that you're playing the role pretty well," Carolyn said after we sat down to breakfast.

Laura wasn't letting go of Tommy. "Daddy, what's that on your finger?" I'd put my engagement ring back on, but turned it around so that the diamond was facing inward. Laura saw right through my deception.

I spun the ring back into position. "Oh, it's just a little present from your Uncle Tommy."

"Little present?" Carolyn gasped. "It looks like the Hope Diamond!"

"Don't be silly. I'm sure it's just cubic zirconium," I lied. "He got it for me as a joke so guys wouldn't hit on me, as if that's ever going to happen...."

"So where do you and Tommy go when you're down in Florida?" Laura asked.

"Oh, he's taken me out to dinner a couple of times - the restaurants are still open in Florida, but we're very careful and we always bring a mask - and we've done some shopping at the outlets, stuff like that, and sometimes we play golf, or tennis...."

"Golf? I suppose you play in a skirt off the ladies' tees."

"Well yes, now that you mention it." I scrolled through the photos on my cellphone and showed them a picture that Tommy had taken of me, trying unsuccessfully to keep my knees together while I lined up a putt.

"This is all so far out," Laura said. "What I can't understand is how you suddenly got into this whole woman thing after Mommy died. Don't most trans people struggle their whole lives with their desire to change sexes? How did Mommy put up with it? And how were you able to keep it from us?"

"I guess I'm the exception to the rule. During all the years I was married to your mother, I never once had any feelings of what they now call gender dysphoria. Even before I met her, I never went there, except for that one time I tried on your aunt's clothes when I was just a kid."

"How about Aunt Gerry? Is she in the know?" Carolyn asked.

"No, I wanted to talk to you two first. Do you think I should tell her?"

"Daddy-O, if you're going to start living the rest of your life as Jeanne, you'd better start telling people. So far only Uncle Tommy, Laura and I know about this, right?" I nodded yes. "When we get home, we're going to break it to our husbands. Gotta start somewhere."

* * *

The girls left shortly after breakfast. There were hugs, and a few tears, and then I was alone again. The thought of how lonely my life might have been if I hadn't discovered Jeanne, and if Jeanne hadn't fallen in love with Tommy, made me grateful for my strange new life in spite of the heartache it was certain to bring me.

During the long drive south, my thoughts turned to my sister Gerry. She was over sixty now, living on Marco Island with her "friend" Tag. Gerry had never married, and Helen and I always assumed that she was a lesbian. Tag, who was a few years younger than Gerry, was a mannish woman we'd always gotten along with, but our visits were few and far between, and I hadn't seen either one of them in several years. Gerry knew Tommy from our childhood days, and she'd reconnected with him briefly during my daughters' weddings, but although they both lived in Florida, her home was in the southwest corner of the state, a good day's drive away.

My drive that Sunday was uneventful. Laura had reminded me to pack some hand sanitizer in my purse, which I was always careful to use every time I pumped gas or visited a ladies' restroom, and I always tried to squat over the toilet instead of sitting down, just like a woman.

I was careful to stay within the speed limit on the freeways, not wanting to test the tolerance of the Alabama State Troopers.

Tommy had drinks and dinner waiting for me when I pulled into his driveway, and although I was exhausted, we talked for hours about my cross-examination by Laura and Carolyn, and their resigned acceptance of the new woman in the family. "They asked me when I'm coming out to Gerry," I told him after we made love (the "reverse cowgirl" again, I was addicted) while we built up steam for another round.

"Why not," Tommy said. "Considering her lifestyle, it can't be any harder than telling the girls."

"Tell me, Tommy, did you two ever, I don't know, connect in some way, considering...."

"Are you asking me if there's a secret handshake between gays and lesbians?" he laughed.

"No, I didn't mean it that way, I was just wondering...

"No, Jeanne, it never came up. I was always pretty deeply closeted around you and your family, although obviously Helen had pretty good gaydar."

"So do you think I should tell her?"

"Of course. Only this time maybe do it in person, the email technique didn't exactly fly with Laura and Carolyn."

"I'll call her tomorrow. Do you mind if we invite her to come visit us here?"

"Why not. Tell her to bring Stag."

"It's Tag!" I punched him on the arm.

"Whatever." I'd been fondling his penis, and he wasn't quite hard again, and neither was I, but we were both getting pretty hot. "Wanna sixty-nine?" he asked.

"I've never done that with you."

"It's different for guys. Much better, in my opinion." He slid down my body and took me into his mouth, leaving his own penis within striking distance, and soon I was sucking on him too. My inhibitions faded away as we got into rhythm, each reveling in the delight we were sharing, until we both came at the same exact moment, pulsing, swallowing, and shuddering in ecstasy. The perfect end to a trying weekend.

* * *

The next morning, I rehearsed my call to Gerry while I walked along the beach with Tommy and Archie. Several approaches were considered and rejected before we settled on an oblique invitation, which was made after we returned from our walk.

"Hi Gene," Gerry answered after her iPhone identified me as the caller.

"Hey Gerry, it's been too long."

"I know bro, I've been thinking about ya. Were you able to get together with the girls over the Holidays?"

"No, but I saw them before and after. We all miss Helen, but life goes on."

"Are you calling from Chicago?"

"No, I'm actually calling from the panhandle. Our old friend Tommy has a place on Santa Rosa Beach."

"Nice! How is old Tommy?"

"Same as always. I'm the one who's a little different."

"Pardon?"

"Why don't you come up here for the weekend and you can see for yourself? You can bring Tag."

"You sound so mysterious...sure, I'll have to check with...her, let me call you back. And Gene, there have been some changes here too, you'll see what I mean when we get there."

She sent me a text later that day. "Tag and I would love to come up on Saturday. Text me Tommy's address. Should be quite a weekend!"

* * *

What does a girl wear when she used to be a guy and she's coming out to her big sister? After much debate, I decided on a colorful sundress which showed off my deep Florida tan, and jeweled sandals which proudly displayed my hot pink toenails. The diamond pendant which Tommy gave me graced my neck, and I was feeling very girlish as I waited for Gerry and Tag to arrive. Archie barked when they rang the doorbell, and I stood a few steps behind Tommy as he opened the door.

It's difficult to say who had the bigger shock: Gerry and Tag, when they saw me dolled up as a woman, or Tommy and me, when we beheld Tag decked out as a man, with a short haircut, a full beard, and hairy arms with bulging muscles under his short-sleeved shirt. The four of us stood there in the foyer, trying to think of something to say, before Tommy finally observed, "This should be an interesting few days...."

That weekend was beyond surreal, beginning with awkward cocktails on the deck, where Tommy, our gay host, tried gamely to spark a conversation between a lesbian woman, her trans sister, and her trans boyfriend. We were all very self-conscious at first, but after the second round of drinks, everyone began to loosen up, and when Tommy declared that we were getting too drunk to drive to a restaurant so he'd better order some takeout, the evening took off. By the time we sat down to dinner - delicious, from the same restaurant Tommy got our Christmas dinner from - laughter filled the air, as we all got reacquainted with our new selves.

There was Tommy, finally out as an openly gay man. There was Tag, formerly a butch lesbian, now living as a man after a double mastectomy and massive testosterone injections. There was Gerry, a lesbian now living with a trans man. And there was me, her little brother, now living as a woman, and Tommy's fiancée to boot. Nothing was held back, as we took turns sharing the most intimate details of our respective journeys.

At some point Gerry asked me how my strange transition came to be. I reminded her of how she used to tease me that she should have been a guy and I should have been a girl. Then I told her about that magical weekend when she was off at college and I found my inner girl in her closet, only to lose her again for forty years until the tragic death of my beloved wife, when she came out again with a vengeance. The three of them looked at me with rapt attention as I described how I yielded to the overwhelming compulsion to shave my legs, put on lingerie and stockings - I spared nothing, including the sudden orgasms triggered by the sensation of silk and lace - and dressed myself in my dead wife's old clothing. Gerry and Tag were completely transfixed when I told them how I'd revealed my secret self to Tommy, and how he'd confessed his sexual orientation and declared his love for me.

Tommy told us of his experiences growing up in a white bread suburb in a loving family, suppressing his hidden, unrequited crush on me, which at the time would have been condemned as perverted, if not criminal. I thought I had pretty much stolen Tommy's thunder, until he regaled us about his far flung affairs while traveling the world for Hyatt, including his torrid affair with a ladyboy from Thailand.

Gerry's story was relatively pedestrian by contrast, but much more complex. She was a tomboy until she hit puberty, when she happily embraced the fun of being a pretty, desirable girl. That all changed her sophomore year in college, when an older boy ambushed her with what would now be punishable as date rape. This had a profound effect on her, permanently darkening her outlook towards men. She had a long career as a schoolteacher, never marrying, a spinster to outward appearances, hiding a discreet succession of female lovers until she wound up with Tag.

It was Tag's history that was the most compelling. Tommy and I sat in fascination as he took us through his girlhood, growing up in a Pittsburgh suburb, the youngest of five children and the only daughter. He was a big girl, and although his mother showered him with dolls and dresses, he much preferred to roughhouse with his older brothers and wear their hand-me-downs. The nickname they gave their sister stuck - his real name was Mary, but everyone called him Tag for the way he tagged along with his brothers wherever they went.

Tag vividly related his first communion, when he was forced to put on a white dress and tights after a furious fight with his mother. He defied her until his father and brothers muscled him into it, but he almost never wore a skirt or dress after that, and by the time he got to high school, he was something of an outcast. The emergence of girls' sports thanks to Title IX was his salvation, and by the time he was ready for college, he was nationally rated as one of the top female field hockey players in the nation. He didn't even mind the skirt he had to wear to play the sport.

Heavily recruited, Tag got a full scholarship to attend Penn State. It was there that he discovered that he was a lesbian, and he enjoyed a number of flings with like-minded girls all through college. A career as a female physical education teacher followed, and eventually he met Gerry, a sister schoolteacher who became the love of his life.

"So when did you decide to become a guy?" I asked him.

"Unlike you, for me it was much more gradual. It actually started when I was in college and took a couple of hits of testosterone - lots of girls on the team did it - not a clinical dose and not enough to do much more than give me a shot of energy and help me add some muscle tone - but I was hooked on the way it made me feel. Anyway by the time I settled down with Gerry, I'd read a lot of literature about female to male transitions, and the more we talked about it, the more I knew that was the direction I wanted to take, had to take. So I talked to a doctor, and she put me on testosterone. It's amazing what it did to me: muscle development, body and facial hair...by then I was retired, so I didn't have to deal with any bullshit, and when my doctor gave me the green light, I had a double mastectomy."

"Wow," I said. "Did you have anything done...downstairs?"

"Not yet. Maybe I will, maybe I won't. The surgery for girl-to-guy isn't as good as it is for guy-to-girl. How about you?"

"Me? I haven't had anything done."

"No hormones even?"

"No. Maybe because my testosterone has waned over the years, it's easier for me to pass?"

"Girlfriend, you really need to get with the program. If genetics have any say in the matter, once you get on estrogen, you'll have tits like your sister in no time."

The very thought sent a thrill up my spine. "I don't know...I guess I could talk to a doctor, but I'm not sure I'm ready for that."

"Let me make an appointment for you with my doctor in Naples. She's very discreet."

"Maybe I will...one thing bothers me: right now it's easy for me to switch back and forth, between sexes I mean. Once I develop boobs...."

"How has this gone down with your family?" Tommy broke in, reading my mind.

"My dad died of a heart attack years ago, and my mom is in Never-Never Land, in an Alzheimer's facility. As for my brothers, we haven't talked in years."

My parents were both gone too, but there was the younger generation to think of. Still, once Laura and Carolyn told their husbands about me, what was to prevent me from taking this all the way, at least from the waist up?

Tommy sensed that things were getting a bit too heavy. "Dinner is served," he said.

* * *

Dinner was delicious, the wine flowed freely, and we talked late into the night, about sports, politics, everything but our unconventional lives. The next morning, two seemingly normal couples enjoyed each other's company over a long breakfast at The Doughnut Hole, before Tag and Gerry drove back to Marco Island. I wore a cute flowered sundress with a little sweater, and blended right in with the after-church crowd.

"Such a sweet dress!" Gerry teased me. She was in a pair of designer jeans, and Tommy and Tag were both in shorts. Ever the metrosexual, Tommy was fully shaved down, making Tag look like a gorilla by comparison, definitely the manlier of the two.

After we were seated and removed our masks, Gerry noticed the ring on my finger for the first time. "Don't tell me you swiped that from Helen?"

"Of course not! Tommy gave it to me," I said proudly.

"At least one of the guys at this table is romantic," Gerry sighed.

"What do you kids do for fun?" Tag asked to change the subject. "During the day, that is...."

"Long walks on the beach, swimming, golf, tennis...."

"Have you tried pickleball? It's the best! When you come down to Marco Island, we'll play mixed doubles."

"What a world," Tommy observed. "Not so long ago, the four of us would have been candidates for a freak show. Now, we're a picture only Norman Rockwell could draw."

* * *

After breakfast, we took a long walk on the beach with Archie before it was time for them to leave. "Come see us soon," Gerry said as we saw them to their car.

"I promise, big sister," I said. Then to Tag: "I've thought about it some more, and I'd definitely like to see your doctor about those hormones...."

"I'll talk to her first thing tomorrow morning."

Tommy and I waved goodbye as they backed out of the driveway towards 30A. "Do you think I'm making the right decision?" I asked him.

"About the hormones? This is who you are, Jeanne, and you might as well run with it. Just don't do anything that involves a scalpel."

"You know, I've been so hung up on Laura and Carolyn that I never even thought about Gerry, but she and Tag are family too now, and after all these years, I've never felt closer to her."

"They do make a lovely couple."

"I wonder what Helen would think of all this?"

"Saint Helen? I know exactly what she's saying: 'Hallelujah, Tommy finally found a girl, and Gerry got her man.'"