A Bend in the Road Ch. 03

This story has been on my mind for a long time. It involves two characters from previous stories of mine: "A Bend in the Road," Chapters 1 and 2. This story is going to take a bit of a different direction from the other two. All of these stories are pure fantasy and maybe a little wishful thinking on my part. I hope you enjoy this one.

*

I had been out of town for several days on a work assignment for my title research business. It had involved multiple properties at the site of a proposed strip mall in a city too far away to make it convenient to drive home every day. The work had taken all of three days, and on this Friday morning I was finished and ready to drive home.

For those of you who don't know me, my name is Cliff Richardson. I am forty-three years old. I am divorced from my wife of twenty-five years. I have two grown children. I have brown eyes, salt and pepper hair (stylishly short), and a not-bad body for a man my age.

I also have a male lover, Tad Sorensen, whom I've been seeing for about four months. Tad and I met when I was a patient in the hospital he works at as a registered nurse. I was powerfully attracted to him from the start. When I was discharged, I worked up my courage and asked him out. Our relationship clicked, and we have become a couple. Needless to say, this "bend in the road" has caused no shortage of consternation among my family and friends. And I admit to having, in a moment of weakness, nearly strayed. But Tad and I are past all that now and we've settled into an exclusive, and very sexy, relationship.

On this particular day, as I set out on the drive home, I called Tad on his cell. It went straight to voicemail (of course), so I left a message that I was on my way home and would see him that evening, at least I hoped I would.

Tad and I do not live together. We both prefer it that way, at least for now. I have a nice house and he has a nice apartment and we split the time between them. I haven't brought the subject up, for fear of being rejected, and Tad hasn't either. Why mess with a good thing?

'Tad and I are compatible in many ways. We share a love of home life, movies, books, and even (some) television. Tad likes to cook, and I like to eat, but we both are very careful. Tad gets me to the gym regularly.

Tad is, by far, the best lover I've ever had. My ex-wife, Margaret, doesn't hold a candle to him. Tad is eager, inventive, and passionate, and he takes pleasure in pleasing me. For my part, I consider Tad's body a wonderland. He is beautiful to me, with his light brown hair, blue eyes and perfect teeth. He's lean and long and the hair on his body is so light as to be almost absent. And Tad has a respectably-sized, circumcised cock which I have gown to adore. This is Cliff talking, a middle-aged man who's been with women his entire life, talking about another man's cock. Talk about a bend in the road!

My phone rang. I looked and saw it was Tad. "Hello," I said, trying not to sound too eager.

"Hi Cliff," said Tad on the other end. His voice had that little lilt in it that meant he was in a good mood.

"Hey buddy," I said. "Just wanted to let you know I'm on my way home. Are we getting together tonight?"

"You know it, hon. How about it we go see the new Jennifer Lawrence movie? It's called 'Serena' and looks interesting."

"Sounds good," I said. "Am I taking you to dinner?"

"If you like," he said.

"I like. Okay, what time?"

"Well, I'm at work now, which is way I didn't pick up when you called. Come by at about eight-fifteen or eight-thirty. That will give me time to get ready," he said.

"Okay, I'll see you then," I said.

I went to the courthouse and spent the rest of the day catching up with work I'd neglected while I was out of town. I was finished by five, so I went home, took a short nap, got up and began getting ready to see Tad.

To say that my relationship with Tad had caused a stir was an understatement. No one had had a clue, including myself, that I would take a man as a lover this late in life. The women in my life, my wife and daughter, had been shocked, but in the end more understanding than my son. He was twenty-two and a senior in college, and the news had rocked him. We were still working it out, he and I. My wife said she understood, but I could tell from her questions that she wondered what she had done wrong. Why had I turned my back on heterosexual relationships to pursue a homosexual one? My reply had been that I still loved women, but I also loved Tad. In retrospect, I think I've been a bisexual all along. I had just suppressed the urges for years.

And then along came Tad at a time when I was lonely and vulnerable, and he was just the right man for me. And so I went for it. I asked him out and he accepted. Like I said, we haven't gotten to the living together part yet, but we are planning a vacation together in a few months.

I didn't know how long Tad and I would last. I said before we were exclusive. Let me amend that by saying that I was exclusive, and so was Tad, as far as I knew. I basically took it week by week. I courted Tad in the old-fashioned way because it's the only way I knew. It was funny though. I couldn't exactly treat him like a woman, but he wasn't my "buddy" either in the typical male shared-experiences sense. He was my lover and my companion, but Tad was perfectly capable of pulling out his own chair.

I live in the country, so I had to allow myself about thirty minutes to drive in if I was to be on time. So at seven I took a shower, shaved, and dressed. I hadn't gone to the gym this week because I'd been out of town. Looking at myself in the mirror, I resolved to go at least three times next week. Was that a hint of extra weight around my middle? I wore my nicest jeans, a button-down white with blue stripes dress shirt, and comfortable hiking boots. My soft brown leather jacket completed my getup. I smiled and checked my teeth. They were fine. I'd had them professionally whitened a while back. Though sound, years of coffee drinking had turned them a slight shade of yellow. Now they were nice and white.

I straightened my house and left, carefully locking the door behind me. I wasn't sure where we'd end up this evening, but I was taking no chances with a messy house. I looked at my watch: seven forty-five. That would put me a Tad's place at about eight-fifteen or so. Good timing.

I pulled up beside Tad's Prius right on time. I could feel the anticipation in my stomach, and especially in my groin. I had purposefully not masturbated while I was away, heightening my anticipation of our reunion. As a result, my semi-erect cock tingled a little.

Tad and I had not exchanged keys yet. We still had separate places. I had confessed my love to Tad, but he had not reciprocated—yet. I considered us a dating couple, and hoped for more. I wasn't sure exactly how Tad felt about me. He could be marvelously affectionate and passionate, yet sometimes he retreated into a private world. To me, he was a bit of a mystery.

I knocked on his door, waited, then knocked again. From within the apartment, I heard "Just a minute." A few seconds later, I heard the lock turning and the chain being pulled back. I started to turn the knob, but I head Tad say, "One second!" I stopped, puzzled. A few seconds later, I heard, "Okay, come in."

I opened the door to Tad's tastefully furnished apartment. He was not in sight. "Tad?" I asked, puzzled.

"Okay," Tad said from the back of the apartment, "I'm coming out now."

I almost said, "I thought you were already out," but decided that it would be lame and in poor taste. So I said, "Okay," instead.

From the hall leading back to the bedroom walked an attractive young woman. She was wearing a dark gray turtleneck sweater with thin red threads woven through it. A small gold heart on a thin gold chain hung around her neck. From her ears hung matching gold earrings. Her hair, the exact shade as Tad's, was short on the sides and a bit thicker on top, and parted on the left. She was wearing well-fitted jeans, and sandals. Her toes were painted coral pink, matching her lips and nails. She was made up sparingly but skillfully: lips, eyes, and cheeks in perfect balance. I noted her eyes, big and bright, and, it seemed, a bit apprehensive.

"Oh," I said, stepping forward and extending my hand. "You must be Tad's sister, I'm...

"Cliff, it's me, Tad," the young woman in front of me said, stepping forward and giving me a light kiss on the lips. Her fragrance, sweet and lemony, washed over me and I reeled a little.

"Tad?" I said stupidly.

"Yes, it's me," the young woman said.

"I didn't know. I had no idea," I said, still shocked.

"I know, Cliff. It's something that I let very few people see. I kept if from you because I didn't know how you'd react." She placed a soft manicured hand on my cheek, looked into my eyes, and asked, "Are you disappointed?"

I closed my stupid open mouth, swallowed and said, "No. No, I'm not disappointed. I'm just surprised. My god, Tad, you're gorgeous."

"Tabby. Call me Tabby," she said, smiling even as her eyes glistened with tears.

(Author's note: From now on, in respect to the character's choice, I will refer to "Tabby" in the feminine, using feminine pronouns.)

I pulled Tabby close and hugged her. She threw her arms around my neck and buried her face in my shoulder. I heard and felt a soft sniffle and sob. She pushed away and said, "I was so afraid!"

"Afraid of what?" I asked, incredulous.

"Afraid you wouldn't want me now. Oh damn," she said, and with a striking feminine gesture turned away from me, plucked a tissue from a box on the coffee table, and began dabbing at her eyes. "I'm going to ruin my makeup! And I spent so much time getting it just right for you. I'll be back in a minute," she said, dashing back to the bathroom.

I stood there dumbfounded. The handsome, if effeminate young man I'd been seeing for several months had transformed into a lovely young woman. I had had no idea Tad was a well, what was he? Was he a transgender? A crossdresser? I didn't know. And yet despite the change, I still found myself aroused and excited. Whether this person was Tad, or Tabby, they still struck a very powerful sexual chord in me. My cock was more than semi-erect now.

I stood in the room waiting, trying to sort out my feelings. I had entered this relationship with a young, attractive man who was now presenting himself as a woman. Was this something I even wanted? If I was truly a gay man, wouldn't I find Tabby unattractive? On the other hand, a straight man would be foolish not to find Tabby attractive. In the end, I decided to just go with it and see how the evening went. I had fallen for Tad. But wasn't Tabby simply a more feminine Tad?

Tabby came out from the back, smiling. "Okay, I think I'm ready." She went over to the kitchen table and picked up her shoulder bag. It was fabric with some sort of Native American design. The she turned to me and smiled a little, looking into my eyes. It was as if she was presenting herself for inspection and approval. Without words, she was asking, "How do I look?"

I felt a slow, involuntary smile spreading over my face. "My goodness, Tabby, you look so different, but so lovely."

"Thank you," she said demurely. Then, with an exquisitely feminine and ladylike grace, she curtsied.

I held the door open for her, and with a very female jingle of keys, bracelets, and wristwatch, we left her apartment. I held the car door open for her (something I wouldn't have done for Tad), made sure she was buckled in, and drove to the restaurant.

***

I kept looking at her hands. Tad's hands had been pale and slender and soft, yet somehow still at least a little masculine. But in the week or so since I'd last been with Tad, his hands had become distinctly more feminine. It wasn't just the nail polish either. It was in the way Tabby held and moved her hands. They also looked softer and a bit glossy with lotion. They were the hands of a young woman.

"I never knew this about you," I said, looking at Tabby over my beer. She had ordered a glass of white wine.

"I didn't let you know on purpose. Very few people know about Tabby, Cliff."

She took a sip of her wine.

"Is this a permanent change then?" I asked.

Tabby swallowed and fiddled with her napkin. "No, it's not permanent. It's...It's an occasional, even a frequent thing. Sometimes I feel more comfortable, more at home with myself, dressing and living as a woman. But at the same time, I'm still not ready to give up Tad altogether. I've been Tad all my life. It's like Tabby is this wonderful vacation that I get to take sometimes."

"You sound a little confused." I said, as gently as I could.

"I'm not. I swear it. Believe it or not, I know who I am and who I want to be most of the time. But I want to know how you feel about Tabby."

Tabby put her hand over mine and looked at me. I could tell how difficult this was for her, how vulnerable she was right then. A few words from me would either reassure her of my feelings, or cut her to the quick. But I am not that kind of person. I never have been.

"Well, I'll admit that it's going to take a little getting used to," I said, "but if it's what you want, then I support you." I gazed at her. "I can't get over how pretty and feminine you are. How could I have not known?"

"Cliff, I was very good at hiding it. I rarely showed this side of me to anybody. Oh, I have a few friends who know. A couple of the female nurses at work know. I've even gone out with them a few times as Tabby."

"But you never told or showed me."

"I know. And for that I apologize. But you have become a very, very important part of my life. I wasn't sure how you'd react. And I didn't want to take the chance of losing you."

As the said this, her voice broke and she squeezed my hand hard. Tears sparkled in her eyes. "I seem to cry at the slightest thing now," she said, brushing her cheek.

The waitress came with our food. Tabby had ordered the restaurant's specialty salad, something with greens and raspberries and grilled chicken and vinaigrette dressing. She also had another glass of white wine. I indulged myself with a mushroom and swiss burger and french fries and another glass of beer.

I poured ketchup on my fries and said, "First of all, you're not going to lose me. I can't remember a time when I've been happier or more fulfilled. I want to be with you whether you're Tad or Tabby. Work it out however you need. We're a couple, or maybe a threesome." I looked at her and smiled. She laughed demurely. Good, I thought, the tension was broken. The rest of the meal went more comfortably.

Once she relaxed, her smile came back and lightened my heart considerably. The light kept catching her earrings and her eyes. Her makeup was flawless, her lipstick perfectly applied. Tabby ate very carefully. She picked through the salad and took tiny sips of her wine. I couldn't believe how ladylike, how feminine she was. Tad must have been this way, practiced it, for a long time. Or maybe it just came naturally. I didn't know. All I knew was that I was beguiled by this person in front of me.

On the way out of the restaurant, it was breezy and slightly chilly. Tabby huddled close to my side, linking her arm through mine and lacing her fingers in mine. She looked up at me and smiled. I kissed her gently and felt her hand on the back of my neck. She played briefly in my hair as our lips and tongues caressed. This is a woman kissing me, I thought.

"Would you mind if we just went home?" she asked.

"Your place or mine?"

"Mine, please."

On the way home, I kept glancing at her. It was still hard for me to believe that this was, or had been, my male lover Tad. "How long have you been...I mean, how long have you felt...?" I began clumsily.

"Pretty much my whole life. I've know I was gay since I was about twelve or thirteen. But I've wanted to dress in girls' clothes since I was much younger. I've always felt more comfortable, more myself around women, dressed as a woman. And I've always been attracted to guys."

"I guess that makes us quite a pair, then. I'd always been with women until I met you. I suppose I wasn't acknowledging the part of me that found men attractive. Then I found you, and it was like a whole new life opened up for me. I'm still a bit confused about my own identity. It's like there are two warring factions inside me. I though, I mean I think you're a helluva good-looking man. Very appealing to me. But you are also just the kind of woman I find appealing. Slender, slightly tomboyish, with fine features. That's you. I don't know who I'm attracted to more. I don't know if I'm no longer supposed to be attracted to Tad, or just to Tabby."

Tabby looked up at me and laid her hand on my arm. "I'm not sure either, honey. In some ways, I feel freer than I've ever felt. But I also feel the tug of my other life, pulling me back."

"Does your mother know?"

"Know what? That I'm gay? Yes. I came out to her years ago. Does she know that I dress as a woman? I think so. A couple of years ago, she came for a visit and found my pretty things and makeup. I made up some story about a female roommate, now gone, who'd left her things. But I don't think she was convinced."

"She didn't say anything?"

"No."

We drove the rest of the way to her apartment in silence, each of us processing our own thoughts.

When we got inside, I plopped down on the couch. "You want to watch a movie or something? Or maybe just listen to music?"

Tabby stood in the middle of the living room looking down at me. She was biting her lower lip and apparently mulling something over.

"Let's just sit on the couch and listen to music. There's wine in the fridge. I'll be back in a minute." She went back into the bedroom and closed the door softly.

I put some music on the CD player and opened the bottle of white wine from the fridge. I poured two glasses, sat back down on the couch, took off my shoes, sipped the wine and waited. I heard the bedroom door open.

Tabby stepped into the living room then. I sat up, put the glass down on the table, and stared. "Oh lord, Tabby. Just look at you."

She was wearing a sheer light blue baby doll nightie and panties. Her modest boyish curves could be seen through the material, as could the slightly darker patch of pubic hair and the outline of her semi-erect penis. The skin on her neck and arms was smooth and white. She had kept her earrings on and they caught the light. She looked like she'd removed her makeup, but her face still looked clean and fresh. Tabby's thighs and calves were smooth and just muscular enough to accentuate their curves. She was barefoot.

She looked at me and asked, somewhat anxiously, "Do I look all right?"

"I don't know what to say," I replied. I patted the couch beside me and Tabby skipped over to me eagerly. She cuddled up beside me. I pulled a blanket over us and pulled her close. We kissed and kissed again. My hands roamed all over her firm body, encountering smooth skin and flimsy material and, yes, her now-hard cock. She sighed when I grasped it, squeezing firmly, then she unzipped me and got mine out. Her warm soft hand explored the length and girth of my penis, passing her thumb over my slit. I was leaking a little, and she smeared my pre-cum over the engorged head.

I was horny and ready to get right down to it, but Tabby wanted to play a little more. "Let's get you undressed," she said, and began unbuttoning my shirt with quick, practiced fingers. It was off in a minute flat, then she said, "Stand up." I stood up beside the couch and she quickly unbuckled my belt and undid the waistband of my pants. My shoes were already off. I stepped out of my pants and stood there in my briefs, the material tenting out in front from my excitement.