L-O-L-A

We had been dating for; let's see, about two months when I found out the truth. Sure I was shocked at first, but it wasn't something I had to get used to. It was something that just WAS.

Let's go back to the beginning. I was 45 years old and recently divorced. Lost really, in a sea of confusion about where my life went from here. I never thought I would be my age and single, and I wasn't quite sure how to proceed, as far as dating went.

I was you're average looking guy, with an unexciting job, just trying to get past today, and hoping for a better tomorrow. What I found was that routine became my friend. Monday through Friday I would get up and go to work. After trudging through 9 hours of feigned interest in the numbers dancing on the computer screen in front of me, I would leave work, go to the gym for a quick work out, and then hit the market for dinner fixings. Then it was off to home where I would prepare an easy, but supposedly healthy meal, which I would then eat in front of the T.V... About eleven o'clock, I would hit the hay, fall asleep with visions of what could have been dancing in my head. The alarm would sound at 6 a.m. and I would get up, shave, shower, dress, and begin the commute to work where it would start all over again. My work week was an unending series of predictable moments.

But oh, the weekends. I would go to concerts, or comedy shows. Sometimes I would do some shopping, or some home improvement project. What an exciting time! Yeah, right.

I had endured about six months of this exciting routine when I met Lola. It was pure luck really. I was on one of my weekend shopping excursions. I believe I was looking for a way to repair some dry wall damage. Really sexy stuff huh? About lunch time I entered a small diner to get something to eat. After ordering my meal, I sat in a booth by the window, drinking my iced tea and gazing out onto a world that was seemingly passing me by. After a few moments I glanced around the diner.

Sitting at a table relatively close to me was a woman by herself. She was willowy and pale. She seemed distracted and maybe agitated as well. As she fiddled with her silverware, she muttered to herself. I found this absolutely fascinating. In a life that had become utterly predictable, here was something truly unusual. I found myself staring at her, and trying to imagine what could possibly have this seemingly elegant creature so worked up.

The more I looked at her, the more I became aware of just how lovely she was. She had auburn hair that hung straight to her shoulders. She had a long pale face, and a patrician nose, but with her wide set eyes, which were like dark pools of solid emotion, the combination was striking. She was sitting with the table obstructing my view of her lower body, but she was obviously thin, though what appeared to be fairly large breasts pressed her blouse from inside.

Her hands, which seemed large, were pale, with long fingers tipped with perfectly manicured nails. Her hands were very animated, fluttering about the table, lifting first her silverware, then a random condiment, seemingly punctuating the conversation she was apparently having with herself.

After about five minutes of observing this unusual and lovely creature, the moment happened. She glanced up, and looked directly into my eyes. My breathing actually stopped for a moment, and like a deer caught in the head lights, I just froze. I could not look away though I knew I should. What seemed like hours, but was actually only a few seconds passed.

Her full lips parted and revealed her perfect teeth. Then she spoke to me for the first time.

"What? Is there a problem?" she said.

Her voice was like something out of an old black and white movie, where the vixen spoke with a smoky, sultry, tone that pulled you in and laid your soul bare.

"N-n-no;" I stammered, "I was just watching you, you are truly beautiful. It's a shame that you seem so sad," I continued.

"Well, it's just been one of those days," she said. "When bad things happen, they all seem to happen at once, you know?" she concluded.

My life had become so monotonous, and this was the chance I needed to shake things up, so I replied, "I know exactly what you mean. Say, I don't mean to seem forward, but would you care to join me and talk a bit?"

She hesitated for a moment, looking around as if an answer to my question, or an excuse to refuse would materialize. She then seemed to come to a decision, and with not another word, she got up and moved to my table, bringing her coffee with her.

She had to return to her previous table to retrieve her jacket and purse. This gave me a moment to fully appreciate the total package. She was tall, maybe 5'9, with long legs and a delicate waist. The gray flannel slacks she wore hugged her curves, and as she bent over to pick up her purse, I was treated to an excellent view of her firm derriere encased in the tight material of her pants.

As she sat down, I was once again struck by how beautiful, and yet how sad her eyes were. As she arranged her things on the table, I took the opportunity to introduce myself.

"By the way, I'm Mark, and I am certainly happy to meet you," I said.

"Oh," she let slip, and all at once I saw hope, fear, and regret flash across her face.

"My name is..." the slightest of hesitations "is Lola," she said.

I smiled to show my pleasure, "It's nice to meet you Lola," I said, "tell me what's wrong."

She seemed to mull this over for a moment, and then she told me her story, and what a story it was.

She started out by telling me she was a pre-op transsexual. You could have knocked me over with a feather. I had NO idea what so ever. Lola seemed so feminine. After the initial shock, I realized what an honor it was she had begun our conversation with this most intimate of details. I suppose on some level I was ready to tune her out, but I was determined to be both bold in broadening my horizons, and understanding to a fellow human being.

We were soon served our meals, and we talked as we ate. I found out she was 36,( almost a decade younger than me), and had just broken up with her boyfriend of eight years. It seemed that Steve knew her back when she was basically just a cross dresser, but had been okay with that and loved her all the more because of her courage. When she had facial reconstruction to feminize her facial features, he was with her all the way. When she had begun living as a woman full time, Steve was right there. However, when she had the surgery to get her breasts, things had changed. Steve became more distant, gradually checking out of the relationship altogether. Finally he sat Lola down and told her the truth. Steve was a gay man, and as such wanted a relationship with a man. As Lola had become more feminine, Steve had become more aware of this fact. The final straw was the breast augmentation surgery. Even though Lola still had male genitals, and no plans to change that fact, Steve now saw her completely as a woman, and as a woman Steve found her less and less attractive until he finally decided he could no longer carry on the ruse of a relationship.

After telling me this sad tale, Lola looked to me for a reaction, but I am sure she didn't expect the one I gave her. I began laughing.

Lola looked shocked, and said angrily "I'm glad I could entertain you with my heart ache."

"No, no," I said, "Do you not see the irony here? Every day on Maury, or Jerry, or Dr. Phil, there are women who were stunned to find out their husbands are now attracted to men. You on the other hand, had a man who was ALWAYS attracted to men, but who left when he finally saw you as a real woman."

"It's both sad and tragic at the same time," I said, "but the irony is funny too."

I could see the corners of her mouth turn up and she began to fight a smile. Truthfully my reaction could have gone really badly with her, but luckily she had a similar sense of humor to mine, and she got it.

"Yeah," she said, "I guess it's kind of funny, and maybe it would be funnier if it ended there."

It seems that after her traumatic conversation with Steve she had gone to work the next day with every intention of losing herself in work, only to find that she had been downsized out of her accounting job. Lola only had until lunch time to say her goodbyes to her work friends, and clear out her desk.

In a haze she had wandered around during the lunch hour, finally ending up in this diner. I had to admit she had a lot on her plate. Figuratively I mean.

Literally, our meals came and we began to trade normal dinner conversation. We had many of the same interests, and even shopped at the same stores, though it must have been at different times because I certainly would have remembered her.

When the check came there was our first truly awkward moment. Did we split it? Did I pick it up? Finally, deciding that it was only fair since I had invited her to join me, I should at least offer to pay. We both reached for the bill at the same time.

"Let me pay for my half." Lola said.

"Nonsense, I invited you to join me, remember? Besides, you need to be frugal until another job opportunity presents itself." I replied.

She was gracious and allowed me to pay without anymore fuss. We finished our drinks and got up from the table.

"Well, I guess I'll pick up a paper and check out the Want Ads," she said.

On the spur of the moment, and without really thinking about it I spoke up. "Why don't you put that off till tomorrow? Let's see what is playing at the movies."

She looked at me in an inquiring manner, and then finally said "That sounds good, but I'm paying my own way this time, this isn't really a date you know."

"I realize that," I replied, "I just thought we could waste the afternoon together since we seem to be getting along so well. Besides, you need to take your mind off of things for a bit."

Without another word we headed off to the movies. We saw a comedy, which was actually very funny. Our conversation before the movie was easy and after the show, we decided to go for a drink.

The liquor flowed freely, and the conversation continued to come easily. The more we got to know each other, the more we realized how much we had in common.

At the end of the evening, I called her a cab. After exchanging phone numbers, she opened the door to the cab, and hesitated. I wanted to kiss her, but I didn't. I don't know if it was the trans-gender thing, or whether it was the fact that I just met her. Maybe I had just been out of the dating game so long I could no longer read the signals. Whatever it was, the moment passed. She got in the cab and was gone into the night.

Part deux

Three days passed, I had not heard from Lola, and had chickened out every time I almost called her. Finally I had screwed up my nerve enough to call her.

So it was a Tuesday night, I was home alone, kind of lonely, but it was more than that. I sincerely liked Lola. We had a lot in common, and I wanted to talk to her.

That was how I found myself dialing her number.

She picked up on the second ring. "Hello."

I coughed, and stammered a little, "Hello, Lola?"

"Yes, who is this?"She replied.

"Um, you remember the guy from a few days ago? The one you had lunch with?"

"Mark right? I didn't expect to hear from you."

"Yeah, I was really nervous about calling. I hope things are going better for you."

"I didn't think nerves had anything to do with it." She chuckled. "But yeah, things are looking up. I got a new job, a better one, and Steve came and got his stuff and there was no drama," Lola said.

I didn't catch the thing about nerves at the time, but later I realized that she thought I was put off by the fact she was trans-gendered.

"That's great. I mean it. But, uh, I was wondering something," I choked out.

"What is it Mark?" Lola asked with scarcely disguised anxiety in her voice.

"Could we, that is could I, uh, see you this week end?"

"What did you have in mind?" Lola asked.

There was an undercurrent of suspicion in her voice, and it suddenly hit me, she thought I was looking for an experimental hook up!

I became more frantic "No, I meant, do you want to go out on a date or something?"

There was a prolonged pause on her end, and then. "Okay, wow, wasn't expecting that!"

Things got easier after that. We both relaxed I guess, and the conversation came easier. We made plans for Friday night, talked a while longer, and then said good night.

I somehow got through the day on Friday, really excited about my date with Lola. After work, I hit the gym, took a quick shower after my work out, and headed home. Once there I took a while to get ready, then headed out to pick up Lola. I followed the directions she had emailed me, and in no time found myself in a nice neighborhood on the far side of town. I knocked on her door and she answered quickly.

Lola was a vision. Her auburn hair hung loose and free. She wore a black skirt and kind of turquoise blouse, with a simple silver necklace and matching bracelet. Her long legs peeked out of her short skirt and ended in a pair of black half-heels. We walked to my car, where I held the door for her. Lola gave me a smile, and slid into my car.

The evening was wonderful. We had a nice dinner, a comedy show, and drinks afterward. The conversation between us was easy and not forced. At the end of the evening, I took her home and walked her to the door.

"Um, Lola, I had a really great time with you tonight, but..." I trailed off.

"Mark, look, you are a great guy, a really great guy, but I know I'm not the kind of woman you normally date, to put it mildly. Don't feel like you owe me anything." Lola said earnestly.

"Well, I'd still like to see you again. Are you free for lunch tomorrow?"

And that's how it began. We saw each other almost every day after that. We shopped together, helped each other with home projects, watched TV together, talked on the phone all the time, as well as going out every free night we could. But in all that time, our relationship never became more physical than occasional hugs or hand holding.

Until last night I meant to say.

Part 3

Last night it all changed.

After dinner at an Italian restaurant we both really liked, we decided to rent a movie on pay-per-view at her house and split a bottle of wine. The movie was a romantic comedy that Lola picked out. In truth, movies were one area where she and I differed. I would probably have picked a horror or action movie. That being said, I became engrossed in the story line. It was about a man who was in love with a woman for years, and yet never realized that their friendship could have been so much more.

The similarities in the relationship of the on screen duo and the two of us were not lost on me. I kept stealing surreptitious glances at Lola, seeing her as more than just a friend for the first time. The punch line is that I caught her gazing back at me more than once. There was a longing, and a hope in her eyes that I had never seen before.

Each of us got up at different times during the movie, and both of us sat down closer to the other when we came back to the couch. By the last half of the movie we were sitting right next to each other, bodies touching from knee to hip, and hip to shoulder. At some point, I don't rightly know when, we began holding hands. This was not unusual for us, but somehow it felt different this time.

As the movie ended with the hero and heroine in a long overdue embrace, Lola turned to me, opened her mouth as though to say something, then seemed to re-think it. She licked her lips in a self conscious way. She looked so beautiful, so sexy, and so vulnerable, I actually thought to myself, "Okay, here goes."

It was at this point that we kissed for the first time. And it was as magical as any kiss dreamed up by a Hollywood writer. I leaned in, and our lips touched. At first it was soft, tender, and tentative. Our lips came together and the moment seemed to stretch out forever. After a moment, I slipped my hand around the back of her neck, and entangled my fingers in her hair, pulling her to me with more urgency. I felt the tip of her tongue dance gently on my lips, prompting me to further open my mouth. Our tongues danced on each other's and we began to kiss with more and more passion.

Our arms encircled each other and we pulled together tighter, as if trying to physically become one. Our passion became more and more frantic as we kissed, caressed, and moaned softly into each other's mouths. During one of those moments when we pulled our heads apart slightly to gaze at each other I said, "I never knew."

Lola replied, "I have known for awhile, and I hoped you would come to know too."

After more kissing, the kind that seemed to be leading somewhere, Lola said "Do you trust me?"

"Of course I do." I whispered.

"Then stay here until I call you." Lola said.

There were a million questions running through my brain, but I acquiesced to her request.

After about ten minutes in which my passion began to cool, she called me to come to her bedroom. During this period I began to question a lot of things. Did I want to take this chance and ruin a great friendship? Did I want to be intimate with someone who was transgendered? Did my attraction to Lola mean I was gay? Did I care?

Anyway, when she called to me, I gulped down the last of the wine that had been in my glass, stood, and walked to her bedroom door. "This is your last chance to put a stop to this." I thought to myself. "I don't want to put a stop to it, in fact I have wanted this for a long time." The part of my brain that is honest replied.

I put my hand on the door and opened it to find and empty room. I walked in and saw candles lit and positioned in different spots about the room. The bed was turned down and dressed in what appeared to be red satin sheets. As I stood there and took in the scene, the door to the master bathroom began to swing slowly open.

Lola stood in the now open doorway, and what a vision she was. Dressed in a slinky, sexy, silk teddy and high heels all black, and bright red lipstick, she stood there with her hip cocked to one side.

'Well?" she whispered in a sexy, sultry voice.

"Oh..." was all I could manage to say.

"I was hoping you would feel that way." Lola replied. With these words she moved towards me. We wrapped our arms about each other and began to kiss again.

I needn't have worried about the break between our make out session on the couch and this moment. All the heat and passion came rushing back like an all consuming tidal wave.

My hands slid down over the small of her back and onto the firm rounded globes of her well formed derriere. I pulled her tight to me as our tongues explored deep into each other mouths. When I pulled her tight to me, I felt more than heard her moan. A delicious vibration traveled to my body from hers, and I could feel the large, fleshy mounds of her breasts press against my chest. Her nipples were as hard as two beautifully placed diamonds pushing deeply into the flesh of my chest.

Lola's hands moved down my back to cup my buttocks, before moving in between our bodies. As her hands slid around to my crotch, my straining cock threatened to burst right through the thin material separating it from her hands. As soon as she had a hand on my rigid pole, Lola knelt down and began unfastening my belt and pants.

No sooner had my pants pooled around my ankles Lola engulfed my cock with her mouth. She took more than half of my length with her first move. She began to bob her head, taking more and more of me with each time until my entire length was embedded in her throat. The muscles in my legs tensed up, and I rose up onto my tip toes, grabbing onto a luckily placed dresser to balance myself. Lola began moaning deep in her throat sending delicious tremors through my body as she continued to deep throat me over and over again. As all this was happening, she began to softly fondle and stroke my balls with one hand, and gently caress the crack of my ass with a finger of her other hand. The competing sensations were almost too much for my system as my body and brain fought to interpret and enjoy all that was happening.