A Bend in the Road Ch. 03

"It is sheer heaven for me, babydoll. Are you my little cocksucker?" I asked.

"Yours and yours alone," she replied.

Tabby set to work again with hand and mouth, working me up to a near climax before engulfing me with her loving mouth, sucking ardently and moaning with pleasure. For my part, I was not going to be able to hold out much longer. Tabby's expert ministrations caused my pleasure to build quickly. At last all I could do was gasp, "I'm going to cum very soon!"

"Mmm, give me that hot cum, baby," Tabby said urgently before taking me back into her mouth. Suddenly, the feeling of her mouth, the pressure and rhythm of her hand were too much. My pleasure peaked, became almost painful in its intensity. A sweet-sharp sensation flowed from my ready-to-burst penis into my lower body, and I felt a bead of semen travel down the length of my cock and shoot out the end, accompanied by an explosion of pleasure so intense that I nearly passed out. For long seconds, my cum pumped from me into Tabby's hungry waiting mouth, while I cried out unintelligibly, completely caught up in the throes of my orgasm. My heavens, Tabby (or Tad) could suck a cock!

When she had drained me and swallowed, she crawled up beside me on the bed and snuggled into the crook of my arm. "How was that?" Tabby cooed (with a self-satisfied little smile).

"Unbelievable, as always," I declared a little breathlessly. "Give me a moment to catch my breath and I'll return the favor."

"No need for that, sweetie. I'm going to shower and go out with some of my girl friends. I'll be gone most of the day."

"Oh," I said, a bit disappointed. I had hoped to spend the day with Tabby. Maybe take her out to lunch, get to know her. "Well, when can I see you again?"

"Call me this afternoon around five. We'll decide on something. Do you want the shower first?"

"No, you take it," I said. But I was too late; she was already headed to the bathroom. I looked at her shapely ass twitching and wondered what had happened to the young man I'd fallen for. Maybe it was better that we spend the day apart. Perhaps I needed some time to think about what was happening.

I considered going straight home from Tabby's apartment, but after we'd kissed goodbye I went to the gym instead. There, I indulged myself in a long workout, thinking about what had happened in the course of a day and night. After years of an unsatisfying relationship with my wife Margaret, I had found a very satisfying relationship with a man. But then, that man turned out to be a crossdresser. Or was he a transgender? I wasn't sure. From what Tabby said, it seemed that what I was dealing with was a crossdresser who was also gay. I had heard of straight crossdressers. Those were men who enjoyed dressing like females because it made them feel closer to women. But what about gay male crossdressers? How did they identify? I found both Tad and Tabby very attractive, for similar, but not identical reasons. I loved Tad's somewhat feminine mannerisms and his good looks. But I also loved his maleness. I found his firm, slightly angular, flat-chested body utterly bewitching. And, as I've said before, I adored the ultimate symbol of his maleness, his respectably-sized cock. On the other hand, I was hard-wired to appreciate and be attracted to women as well. And no one, especially me, could have denied that Tabby was an attractive woman. In her dress, her mannerisms, her attentiveness to me and, of course, her lovemaking, Tabby was irrefutably female.

By this time, I had finished my circuit training and I was engaged in a cardio workout on the stair climber. I hated the stair climber because it was hard and tiring. But it was so effective at burning calories and strengthening my thighs that I dared not skip it. Today, I passed a grueling twenty minutes climbing stairs thinking about my predicament. In the end, I was sweaty, tired, and aching. I had also made up my mind about what I wanted.

I wanted both Tad and Tabby, if they would have me.

***

That evening around five, as instructed, I called Tabby on the phone.

"Hi!" she said when I called. "What did you do today?"

"Nothing much," I replied. "Worked out, did some paperwork, watched some cable."

"Did you decide anything about us?" she asked, more seriously.

"I'll tell you over dinner," I said.

"Cliff, are you going to hurt me? If you are, you can just tell me over the phone."

"No. I'm not going to hurt you. I promise. I just need to see you. Tonight."

"Would you prefer to see Tad? Or Tabby?"

"Come as whoever you want. I mean it. I just want a nice evening with whomever you're most comfortable being tonight. I'll be glad to see either one."

"Okay, if you say so. How about picking me up about seven?"

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

Once again, and as always, I showered and dressed carefully. I had never let Tad see me at anything but my best. The relationship was that important to me. Tonight, I wore a pair of dark blue slacks, a pink shirt and the beige cashmere sweater Tad had given me as a present. I shaved carefully, for the second time that day, and wore just a little of a cologne that I knew Tad liked. My hair, fortunately, was at just the right length, halfway between cuttings, and (I thought) the touches of gray at my temples made me look distinguished. When I was done, I stood in front of the mirror inspecting myself for my Saturday night date. "All right," I said to my reflection, "let's do this."

I got to Tabby's apartment at seven sharp and knocked on the door. From within, I heard "Just a second." A few seconds passed, and the door opened to reveal Tabby dressed in a cowl neck sweater of emerald green over a saffron yellow skirt. She had on white stockings and high heels that matched her skirt.

Tabby's brown hair was growing out a little, but it was still short and above her ears. It was parted on the left and her bangs covered her right eyebrow just a little. She was wearing pearls this night, a single strand around her neck and two in her ears. Tabby's makeup was perfect. On her wrist hung a small purse.

"Oh my heavens," I said. "Don't you look nice."

She smiled and took my breath away. "Thank you, sir," she said, blushing prettily. She cast her eyes down and curtsied. My heart skipped a beat.

Still staring at her, I managed to ask, "Are you ready?"

"Yes," she said. She opened her purse, rummaging a little and muttering, "Keys, cell phone, okay, I'm ready." She looked at the light jacket hanging on the couch. It took me a second, besotted buffoon that I was, to realize what she meant. I quickly grabbed it and draped it over her shoulders. "Thank you," she said.

I took her to the best restaurant in town. I gave the hostess an extra twenty dollars for a secluded table, and she put us in a corner, darkened but lit by a single warm light.

Our waitress, a young woman in her twenties, came and took our order. She gave Tabby a close look, then discreetly smiled and winked at me as she walked away.

"I saw that," Tabby said.

"Saw what?" I asked, feigning ignorance.

"I saw her wink at you and smile," Tabby replied, a slight edge to her voice.

"You know, Tabby, I think that what she was doing was congratulating me on have so beautiful a date."

"Hmph," Tabby snorted, but she smiled a little.

We had chilled sauvignon blanc while we waited for our food.

"So, what's on your mind, Cliff?" Tabby asked.

"Well, all I can say is that your transformation is nothing short of magical. I mean, you make a stunning young woman."

She took a sip of her wine and said slowly, carefully, "It's hard to describe how I feel when I'm dressed and made up like this, when I'm 'Tabby'. On the one hand, I feel exhilarated and free. On the other hand, there is still something of Tad in me that's saying, 'I'm still here.'"

"What will you do about work?" I asked, knowing that at work he was Nurse Tad and not Nurse Tabby.

"I don't know. I suppose that I'll continue dressing as a man for work, at least for the time being. It's funny, Cliff, sometimes I want to dress as a man. I could even say most times I want to dress and act, even feel, as a man. But there are other times when the desire to become Tabby is irresistible. There are times when Tabby feels so right that she can't be denied. Is that pathological?" she asked, draining her glass.

I poured us both another glass of wine. I wanted her to loosen up a little, relax. I want Tabby to know that she could trust me and open up to me, no matter what.

"I certainly don't think it's pathological," I replied earnestly. "I think, like most young people your age, you are deciding who you want to be. It may take some time and soul searching, but you'll figure it out." I took a gulp of wine, and said, "I fell for the person who is Tad and Tabby. You are beautiful as Tabby, and handsome as Tad. Physically, to me, you are perfect. But who I'm really in love with is you. The inner you. The person who's funny and caring and gentle and passionate. Whether you're wearing men's clothing or women's that will not change.

Tears glistened in her eyes. "I always seem to be crying around you nowadays," she said, dabbing with her napkin.

"Baby, you have nothing to cry about," I said gently.

She gave a little laugh, sniffed a little, and looked down. At that moment, our waitress came with the food. Tabby had a small boneless pork chop with home fries and steamed broccoli. I had grilled salmon, brown rice and steamed green beans dressed with a vinaigrette sauce. I ordered another bottle of wine.

The rest of the meal went well. She had gone shopping with her female friends that day, actually some nurses from work. They had known about her for a while, Tabby said, but it was not common knowledge around the hospital.

"Do you see a problem with working there?" I asked.

"I don't think so," she replied, "but the older nurses can be a bit traditional. The fact that I'm gay has never been an issue, at least not with most people. But this might present a problem to the wrong person. However, I do have a backup plan."

"Oh yeah, what is it?" I asked.

"There is a rich old gentleman in town whose health is failing. He's from old family money. Very prominent. He has been after me for quite some time to become his private nurse. The pay would be better, and there would be benefits. But I've been reluctant to take the opportunity."

"Why?"

"Because I love hospital nursing. I love the camaraderie of the other nurses and of the doctors. It's what I'm used to. It's how I was trained."

"Does this old gentleman know about Tabby?"

"Yes, as a matter of fact he does. One night when he was a patient and I was working nights, we had a conversation. You know, one of those three a.m. conversations where you tell your secrets. It was during that conversation that he asked me to come work for him. I told him that I wasn't sure I was right for the job. He said that was nonsense and asked why." Tabby took a bit of her food and a large swallow of wine. I could tell it was starting to affect her. "Cliff, in a weak moment, I not only told him I was gay, but that I liked to dress in women's clothing sometimes."

"How did he react?" I asked.

"He began crying," Tabby said. "He said that, in that big old house that he lived in, there was a closet that he kept locked, and only he had the key. In the locked closet he kept his 'fineries' as he called them. There were dresses, petticoats, blouses, undergarments, all the things he'd accumulated in a lifetime of crossdressing.

"Is he gay?" I asked.

"No. He's straight. But in all his life, he'd never been able to wear his feminine attire outside of his bedroom for fear of being discovered and publicly humiliated."

"Wow, that's quite a story," I said, pouring us both another glass of wine. We were both nearly finished with our meal, but my head was swimming a little. I want to keep Tabby talking, though.

Tabby continued, "Quite a few years back, he said, he'd hired a photographer to take some pictures of him in his female clothing. There were even some 'boudoir' shots as he called them."

"Don't tell me," I said, "the photographer tried to blackmail him."

"Happily, no," Tabby said. "They're quite professional, and he's very fetching in them. He told me they are his prized possessions among all his wealth."

"He sounds very special," I said quietly.

"He is a special old gent," Tabby said. "He told me that if I came to work for him, I could dress any way I wanted, any time I wanted. I would never have to worry about anything professionally."

By this time, we were finished with our meal. Our waitress came by and asked if we wanted dessert. I looked at Tabby. She shook her head no. "How about two coffees?" I asked. The waitress nodded and left.

"Well Tabby, all I can say is it sounds like a good opportunity," I said.

"I know. I just haven't decided. Sometimes I just can't make up my mind."

"Well, whatever you decide, I'm behind you all the way," I said.

"Does that mean that all this," she gestured to herself, "isn't too weird for you?"

I held her hand in mine and looked into her clear blue eyes. "I'll admit that it's going to take a little adjusting on my part. But I meant what I said. I'll be here for you as long as you want me."

Tabby looked at me, finished her coffee and said, "Take me home, Cliff." She had a naughty twinkle in her eye.

On the drive home Tabby got as close to me as she could (my car has bucket seats), and kept her hand in my lap, playing with my thigh. Needless to say, driving safely was a challenge.

We got back to her apartment, put on a movie (I honestly don't remember which one.) and began making out on the couch. We hadn't bothered to undress; we just caressed each other through our clothes. I was kissing her, savoring her breath, her taste, her lips, when I suddenly had to have her in my mouth. I slid down to the floor and knelt in front of her. I pushed her skirt up to reveal, oh my god, frilly light green panties and a matching garter belt. The sheer material of the panties could hardly contain her sizable, fully erect penis. It strained against the material, a quarter-sized wet spot showing where her panties met the tip. Tabby had thoughtfully put her panties on over her garter belt, so when I hooked my thumbs under the elastic waistband and pulled, all she had to do was raise her fanny up to divest herself of the garment.

I pushed her knees apart and laid my head on her smooth flat belly. Her cock was right at the level of my mouth and nose, twitching slightly with excitement. I could feel its heat, smell its light musky scent. I kissed the head, running my lips and tongue lovingly over it, moaning as I did so. I opened my mouth and the warm hardness slid home as if it belonged there. A great feeling of contentment washed over me. I was sucking a cock, something I had always wanted to do. And it wasn't just any cock, it was the cock of the person I loved. I opened wider, taking more inside.

With my mouth full of Tabby's delicious prick, I sucked hard, feeling a drop of salty pre-cum ooze out of the slit on the end.

"Oh baby, that is so, so good," Tabby purred. It was music to my ears.

"Mmmm," I moaned, unwilling to relinquish her cock, even for a second.

I kissed her from her sparse tangle of pubic hair all the way to the helmet head, loving every one of her seven inches, savoring every moment, every nuzzle, every kiss. What I lacked in cocksucking experience, I made up in ardor, as Tabby's sighs and moans testified.

"Do you love me, Cliff?" she asked breathlessly.

"Yes baby, I love you."

"Do you love sucking my cock?"

"Yes baby. I love love love it."

"Oh baby!" she gasped as I swallowed her completely, laving her shaft with my tongue, feeling the head nuzzling the back of my throat.

I released her for a second. "Tabby honey, please give me your sweet cum. I want to do this for you. I want you to know how much I care."

I swallowed her again, my whole being centered on this wonderful hot thick penis in my mouth. It felt like a part of me. A wave of sensuality swept over me as I realized how intimate mine and Tabby's connection was at that moment.

I began moving my head up and down on her cock, and pumping gently with my fist, hoping to coax some sweet semen out. Tabby spread her stocking-clad legs wide, allowing me full access to her groin. Her soft, scented pubic hair tickled my nose. I felt her fingers in my hair, urging me on.

There was nothing in the world for me right then except the feel, taste, and smell of my lover's cock in my mouth. Her pre-cum leaked steadily now, giving me a taste of what was to come. I sucked and pumped. Tabby grunted in ecstasy, fingers twisting in my hair, thrusting her steel-hard phallus in and out of my mouth. Every fiber of my being became concentrated into one point, that point being the place where her body and my body connected: my mouth. There was nothing in the world I'd ever wanted more than for Tabby's cum to flood me. I wanted to taste her, savor her essence, swallow her hot juicy load and feel it slide down to my belly. I was in love with this cock and the person attached to it.

My efforts soon paid off. Tabby began gasping, sobbing, "Oh Cliff baby, I'm going to cum!! I'm going to cum in your sweet mouth! Oh! Oh! Oh!"

And I felt the hot salty spurts of sperm shoot out of her cock into my hungry waiting mouth. She bucked and jerked, grunting and sending the semen into my mouth with great force. I kept her inside, sucking gently, swallowing as best I could, riding out the storm in her loins, loving every precious drop of man-seed.

When the flow stopped, I slowly disengaged myself, sucking as I backed off, swallowing the last drop as I let go the tip. I crawled back up on the couch and took Tabby into my arms. She threw her arms around my neck and kissed me deeply. I got up and pulled her up with me and led her into the bedroom. We made love all night long.

The next morning, I awoke to the sunlight from the window in my eyes. I reached over to find Tabby, but I was alone in the bed. Then I heard the toilet flush and the bathroom door opened and out stepped a handsome young man in a clean white tee shirt and jockey shorts.

"Good morning," I said, yawning.

"Good morning," he said.

"Is this Tabby or Tad I'm speaking to?" I asked carefully.

"This is Tad, silly," he said, coming over to sit on the side of the bed. He leaned down and kissed me with toothpaste-fresh mouth. "And how are we today?"

"I'm fine," I said, throwing back the cover to reveal my morning hard-on. "Not bad for an old man, huh?" I asked, smiling.

"I'm surprised you can even get it up, as much as you used that thing last night." He patted his bottom. "I'm a little sore this morning."

"What can I say? I missed you. A lot."

"And I appreciate it, lover."

I sat up in bed, which gave me a few seconds to choose my words carefully. "So, no Tabby this morning?"

"No. Tad is back, at least for awhile. I love being Tabby. I am Tabby, at least part of me is, all the time. But Tabby can go back into the closet with her clothes for now." Then he stopped, took a deep breath, looked at me and asked, "Is that too weird? I mean, can you handle that, Cliff? Because if you can't, I need to know now. I'll admit it: I've fallen hard for you. But if you can't deal with me, with us, I mean Tad and Tabby, I need to know before we go further."

I looked up at his face, his blue eyes, his adorable nose, his shapely lips, his clear skin. I looked at his slender neck, his smoothly muscled arms, his fine beautiful hands. I considered his wit and humor, his warmth, his passion and his caring attitude. I thought about all those qualities that had attracted me to Tad in the first place and inserted them into the feminine frame that was Tabby. And in the end, it made no difference whether this person before me wore a dress or a pair of khakis. I wanted to be with the person. And if that person needed to be male one day and female the next, who was I to judge?