The Road Less Traveled

The Road Less Traveled

© 2020 by Thrillerauthor

I snuggled up next to Tommy on the sofa while his hand continued to caress and squeeze my manhood through my panties. Instinctively, I started doing the little things that a woman does to please her man - I leaned over and breathed deeply into his ear while I nibbled on his ear lobe, and then I reached down and started to massage his manhood through his trousers. Not quite believing that I was doing it, I unbuckled his belt, unbuttoned him, and began sliding down the zipper...meanwhile his foreplay grew more intense, and I felt my panties being tugged down to my knees as he continued to squeeze and caress my penis and balls. I was getting hard fast, and so was he. His penis popped out of the fly in his boxers. "Goodness!" I exclaimed in a girlish, breathy voice.

"This isn't very ladylike," he observed as he stroked my penis into a rock hard pole.

"You're a big boy," I responded. Tommy was 6'2" tall and he was very well endowed. "You make me feel like a little girl."

"Then you'll have to be the bottom." I was confused for a moment before I figured out what he was telling me, and I lay back passively while he continued undressing me. After my skirt, top and panties were off, he stood up and removed his shirt, khakis and underwear. Then he took my hand and led me into his bedroom, which had a king sized bed. I watched with apprehension while he tore off the bedspread and pulled back the top sheet and blanket. "Don't worry, I'll be very gentle," he whispered while he lay me down and positioned my butt under one of the oversized pillows. I heard a nightstand drawer open, and it took me a moment to realize that he was slipping on a condom and lubing it up. Then he was on top of me, and I squirmed at first until he found my sphincter with the tip of his penis and slowly began to penetrate me.

"Ouch!" I cried with the first shock of pain when he stretched my opening in a way it had never been before. Then he was inside me, just a little bit at first, but after he pulled back a bit he entered me again and again, deeper and deeper each time as his steady, gentle thrusting progressed. I felt like I was being impaled as he continued to fuck me, until his long, hard penis approached my prostate and a sudden wave of ecstasy overcame me, accompanied by a feeling of complete, abject surrender as Tommy had his way with me. I have never felt so completely helpless...so utterly used...so fucking good!

Tommy must be getting close himself, I realized as his breathing grew faster and faster, and then suddenly I was surprised when my own climax started, slowly at first, unlike any other orgasm I'd ever had, much deeper and more intense. I must have cried out in ecstasy when I finally released, and then I could feel Tommy's own spasms commencing deep inside me, which triggered a second round of spasms from me, or maybe it was just a prolongation of the most devastating orgasm I'd ever experienced. The feelings of raw, carnal pleasure continued longer than I ever thought possible, and were matched by Tommy's steady thrusting until he finally eased off and collapsed on top of me.

"Help, I can't breathe!"

Tommy rolled off me and his hand found my softening penis. "I thought I felt you joining the party," he said. "Was it good for you too?"

"That was unbelievable, like nothing I've ever imagined," I sighed.

"I haven't felt that good in a long, long time, maybe ever. I can't believe that after all these years, we found each other at last."

"Me neither. And you know what? I think it's even better this way. I know that I would have been all torn up about whether what we were doing was wrong somehow. Now I don't feel that way at all."

"You don't feel a little guilty about...you know...after all those years with Helen?"

Helen was my dead wife's name. "I don't know Tommy, a day doesn't go by that I don't think about her, but life goes on. If I'd never met her, or if you and I had grown up in today's world, things might have been very different, between us I mean. But here we are now, as if the last thirty years never happened. Maybe I should feel guilty about that, but I refuse to go through the rest of my life living in the past. That's why I came down here, to see if maybe there was a chance for some kind of future with my best friend...."

"So you always suspected I might be gay?"

"No, although Helen was sure of it."

"Ha! She was a wonderful gal, always right about everything, it turns out."

"Yes. Tell me Tommy, were there women in your life too?"

"You mean am I bi? No, not really. Oh I tried it a few times in college, but it never really worked for me. Closest I ever came to falling in love with a woman was a ladyboy in Thailand."

"You're shitting me!"

"It's true. I was leading a team that was opening a new Hyatt in Bangkok. Opening a five star hotel is incredibly stressful, and we always sent a hand-picked team from Chicago to work out the bugs and deal with all the crises that seem to crop up. A few days before the opening, a couple of the guys persuaded me to take a night off, and we found ourselves in a bar where the most beautiful person I've ever seen came on to me. She was a he, although you'd never know it, and we fell in love. I hated it when I finally had to return to Chicago, and I even asked her to come back with me, which she did. But after a few months, she was miserable - I was traveling all the time, and a few months of Chicago winter were enough for her."

"That's so sad."

"Not really. We never had that much in common. Nothing like you and me, Jeanne."

"I know! It's so amazing, growing up we were inseparable, and even after I met Helen, you always seemed like part of the family."

"And now we're lovers at last." He leaned over and kissed me, a sensitive, soulful kiss that I never wanted to end. When it did, he whispered, "I've always loved you."

"And I love you, Tommy. My best friend, my lover, my soulmate."

Our pillow talk continued like that through most of the night. At some point I slipped into the nightgown I packed - a satiny creation that I used to adore on Helen - and when we finally fell asleep, he spooned me like we'd been sleeping together all of our lives.

* * *

When I woke up the next morning, the bed beside me was empty. I thought I heard Tommy downstairs, and when I walked out into the hall Tommy was just closing the front door. I looked out the window and saw him staring off on his morning run, a daily ritual that he'd been doing since college, one of the reasons why he was always so buff.

Perfect! He'd be gone for almost an hour, time enough for me to take a shower and dress myself up in something pretty for him. After last night, I wasn't going to take anything for granted! I was momentarily stunned when I saw my reflection in the bathroom mirror - my wig looked like I'd just stepped out of a hurricane, and my makeup was a mess - but my wig brushed out with a few strokes, and after I creamed off my makeup I took a long, hot shower. There was a bit of stubble on my legs so I shaved them standing up - not as hard as it sounds - then after I dried myself off and moisturized all over, it was time to reapply my makeup - was this going to become my daily routine for the rest of my life? - put my wig back on and, once again looking years younger, I selected a black tieback top and a longish, swirly black and white skirt. I put on a black wonder bra and panties, stepped into a lacy black half slip, and was about to put on my skirt and top when the doorbell rang.

Tommy must have forgotten his key! Without thinking, I skipped to the front door and opened it to receive the shock of my life: a total stranger was standing there, holding a bag of takeout! "Doordash," he said as he looked me up and down.

"Oh, I'm so sorry!" I said, holding one hand over my breasts while I reached for the bag with my free hand. I was so embarrassed!

"Don't apologize to me sweetie, you made my day," he smiled. Then he winked at me before I slammed the door in his face. Still mortified, I finished getting dressed before I took the bag into the kitchen and tried to take my mind off my half-naked encounter with a randy deliveryman by busying myself with womanly tasks. Tommy had ordered breakfast from some place called the Doughnut Hole, and I had to admit that it looked delicious, a large egg scramble that would be big enough to split and some cream filled pastries. I put the eggs in the oven on low to keep them warm, and I was just starting to set the table when Tommy walked in.

"I see my secret lover has turned herself into Suzie Homemaker," he said, leaning in to give me a kiss.

"Eww, you're all sweaty! Please go take a shower while I finish up in here."

"Yes, dear," he chuckled, and he did as he was told. By the time he returned, looking incredibly handsome in a tee shirt and shorts, I'd poured some orange juice and made the coffee, and he watched me as I took the eggs out of the oven and divided them on our plates. "Where have you been all my life?" he asked me as he moved in for another kiss, and this time I let him, wrapping my arms around his neck and kissing him back like there was no tomorrow.

Eventually, we broke off the clinch and sat down to breakfast. We sat there contentedly eating at first, it really was delicious. Finally I confessed, "I'm afraid I caused a bit of a scandal this morning."

"Oh?"

"When the doordash guy came to the door with breakfast, I greeted him in my bra and slip."

Tommy threw back his head and laughed hysterically. He was actually crying with laughter. "Oh my God, that's the funniest thing I've ever heard."

"Well, it wasn't very funny to me, buster. It was the most humiliating experience in my life!"

"You poor thing...what did he say to you?"

"He called me sweetie and told me I made his day, the creep."

"Are you kidding? That poor guy paid you the highest possible compliment -- you were half dressed and he told you he thought you were a woman!"

"He did?"

"Of course he did! I was wondering whether to ask you out to dinner tonight, and this clinches it."

"What are you talking about?"

"Look, the moment I saw you last night, dressed up like a chick, I thought sure that you were drop-dead passable, but let's face it, my eyes are a little bit blinded by my feelings for you. That guy just proved it beyond any doubt. You, my darling Jeanne, are one hundred percent passable as a woman, and I would be honored if you let me take you to my favorite restaurant tonight."

"Now hold on, Tommy, I don't think I'm ready for that. It's one thing to dress up as a woman around the house, but to go out in public? Sorry, but there's no way."

"What the hell are you afraid of? Nobody down here knows who you are, in the first place. And in the second place, I'm the one taking all the risk here -- I'm very well known on 30A, and I've been to this restaurant dozens of times. If I wasn't totally sure that you'd pass with flying colors, I'd never have asked you. And I am asking you, again: please be my date tonight!"

My resolve was weaking, but I was still pretty sure this was a bad idea. "How about the Coronavirus? Aren't all the restaurants closed?"

"This is Florida, sweetheart. Unlike Illinois, the powers-that-be have taken a less enlightened view. I wouldn't dream of taking you to a crowded joint in Destin, but the restaurant I have in mind is very exclusive, and anyway we'll get an outside table."

"Are you really sure you want to do this?"

"Are you kidding? Do you know how sick I am of going to a restaurant and asking for a table for one? Just when I'd given up all hope of ever finding someone to go out with, my best friend has turned himself into a pretty girl, someone I can talk to, someone I'd be proud to be seen with...please don't say no!"

"What would I have to wear?"

"Anything works down here. Did you pack a dress?"

"Yes," I admitted. "I even threw some heels into my suitcase. You're so tall, I think I can get away with them, if you really think this is a good idea...."

"Of course I do!" He took out his cellphone and made a dinner reservation for seven o'clock. "Now that that's settled, let's take Archie for a walk on the beach."

I have neglected to mention that Tommy has a dog, a feisty terrier mix named Archie. He'd greeted me happily like always the night before, and by the time I'd transformed myself into Jeanne he was asleep in his bed. That morning, he'd joined Tommy on his run, and now he was hanging around the kitchen mooching for breakfast leftovers. It suddenly occurred to me that the fact that I was now dressed as a woman meant nothing to the dog. When I mentioned this to Tommy, he shrugged it off. "Dogs don't get hung up on clothes, Jeanne. He knows you're the same person you've always been."

"Am I?" I asked out loud

"Definitely. Jeanne, as you call yourself now, was always a part of your personality, buried just below the surface. How you kept her down there all these years is a tribute to Helen and the powerful hold she had on you. Do you think she ever suspected that you wished you were a woman?"

"No, because I really didn't have those feelings as long as she was alive. It wasn't till she was gone that I discovered Jeanne." We were walking on the beach, me barefoot in my skirt, which swirled about my legs in the breeze. Tommy took my hand, and we strolled along the surfline like the two lovers that we were. "This sand is unbelievable, like talcum powder." And it was, as pure and white as any beach I'd ever seen.

"Everything about this day is unbelievable. At this time yesterday, I was a lonely old bachelor, and now I feel like a twenty-four-year-old on his honeymoon. I didn't think I could even get it up any more, until last night...."

"I know just what you mean." I squeezed his hand. "Before I tried on Helen's clothes, I'd given up on ever getting off again. I didn't even get her stockings on before that notion was disproved."

"Wow. So it's a rush for you to dress up as a woman?"

"Oh yeah, incredibly so. I can't imagine ever having an operation to turn myself all the way into a woman, what if it just neutered me?"

"Please don't go there! Like I told you last night, I love you just the way you are."

"Don't worry! It might be nice to have boobs, though...."

"Hmmm...I'm really a leg man, but I'd be fine with that."

"Well, let's not get ahead of ourselves. Helen's old wonder bras work wonders."

* * *

Tommy and I snuggled on the sofa like teenagers after we got back from our long walk on the beach, but neither one of us wanted to take it too far. We had a big date coming up, my first ever date as a woman. After encountering dozens of passers-by on the beach, my confidence in my passing ability was running high, and I was actually excited about the prospect of getting all dolled up for a romantic evening on the town with Tommy.

By then, I'd moved my things from the guestroom to Tommy's bedroom, and when I asked him if I could take a bath in his oversized tub, he asked me if he could join me! I told him I might ask him to join me when I called him, only not for the purpose he had in mind...he seemed mystified but assured me that he'd come when I called him.

It was heaven to lower myself into a steaming hot bubble bath once more, and I took my time shaving my chest, arms and legs again. When I finally summoned Tommy, it was to ask him if he wouldn't mind shaving my back? "No problemo, baby," he laughed. He sat on the edge of the tub, lathered me up and gently whisked off the few hairs that were back there. "Smooth as a baby's bottom, are you sure you don't want me to join you?"

"Cool your jets, Mister! I want you to be good and frisky for me tonight."

"Yes ma'am," he said before retreating from the bathroom. I lowered my head and giggled into the bubbles.

* * *

There is something indescribably exciting about shaving your legs...putting on your makeup...styling your hair just so...and putting on a pretty dress for a date with a handsome man. I selected my bra and panties, and a full-length slip to wear under my dress, a confection in black, white and yellow that I thought would be perfect for Florida. Tommy told me that it was going to be chilly at night, so I eased a pair of sinfully sheer pantyhose up my freshly shaved legs, which started a small war in my panties between my penis and my will-power. "Down boy!" I scolded myself, "we have a big date tonight and you're not going to spoil it now!" Eventually it obeyed, and after it did, I tucked it back between my legs.

Then it was time for my dress. After I dropped it over my head and zipped myself up in the back, which took some doing, I put on the jewelry that I'd selected for it (memo to self: sooner or later, you're going to have to get your ears pierced, better start thinking about how you're going to explain that to the children and grandchildren) gave myself a spritz of cologne and stepped into my heels, a pair of black stilettos that looked insanely sexy on my feet. My dress had a matching belt, and after I put it on, I remembered that women fasten their belts in the opposite direction from men, so I took it off and put it back on again. Then I took a few minutes organizing a purse for the first time in my life. Let's see: lipstick, wig brush, compact with a little mirror, cell phone, what else did women carry around with them? Maybe some tissues...don't need to worry about keys, Tommy will be driving me...." I snapped my purse shut, draped it over my shoulder, picked up my sweater coat, took a long last look in the full length mirror, and opened the bedroom door. My high heels clickety-clacked on the mission tile floor as I made my entrance into the living room.

Tommy was waiting for me in a sport coat and slacks with an open collared shirt. "Wow," he said. "You look stunning, I love your dress."

I walked up to him and gave him a peck on the cheek. "You do know how to make a girl feel great. I'm so lucky you didn't let one of them snap you up."

"Ha! Are you nervous?"

"Terrified!"

"Here, this will calm us both down." He handed me an oversized glass of white wine.

"Don't tell me you're nervous too?"

"Not nervous, just excited. Here's to us," he said, clinking his glass against mine. After we both took long sips, he pulled out his cellphone and said, "Here, let me take a picture of you to remember this by. He stood back while I tried to figure out how to pose as a woman. Just then Archie came trotting up, wagging his tail, and Tommy caught the two of us together before I had time to think about it. He laughed when he looked at the picture in his cellphone. "Archie looks like a demon dog with those eyes caught by the flash, and you, my dear, look lovely." I laughed when he showed it to me, then we sat down on the sofa and talked about nothing in particular until it was time to head for the restaurant.

Tommy opened the passenger door of his Porsche for me, and he made sure I was strapped in before he got behind the wheel and drove us to a fantastic seafood restaurant on a pier overlooking the Gulf. We each put on our masks, and we were immediately shown to a lovely outdoor table. I shrugged off my sweater and draped it over the back of my chair, just the way I'd seen my wife do it during our thirty years of marriage.

I heard a faint buzzing sound, and it took me a moment to realize that it was my cellphone, ringing in my purse. I was going to ignore it at first, but then I was afraid it might me one of my daughters, calling about some family emergency. "I'm sorry, Tommy, this might be important," I said as I reached into my purse and dug it out. By then my phone had stopped ringing, and the icon for a voicemail popped up. I tucked back my hair and pressed my cellphone to my ear. It was my older daughter, who lived in New Jersey.