The Secret

I was in a bar one night with some friends. You know, the usual beer and bullshit session. Conversation turned to how many women we used to pick up when we were younger and how, as you get older, it's not as easy as it used to be. And of course after a few beers, there's always the one who wants to make a wager. Everyone puts in 20 dollars and the first one to pick up a woman in the bar gets the kitty. Juvenile behavior, yes. But I went along with it just for kicks. There was 120 bucks at stake. What the hell.

Everyone was striking out and then I spotted a long-legged beauty sitting alone at the end of the bar. Long blonde hair in a black mini. I casually strolled over and ordered another beer, taking the stool next to her. She had her back to me, but if the front looked anything like the back, she was definitely worth taking a shot at.

"Kind of crowded in here tonight." I said as an opener.

"Yeah, I guess." She said as she turned to face me. "Oh shit."

I didn't know what she meant by that at first, and then I recognized her. Or I guess, I should say 'him'. It was Paul from the office. He worked in accounting. I was used to seeing him wearing a tie and his hair in a ponytail. We weren't really friends but we had spoke in passing. He always seemed kind of shy.

"Please don't say anything. Please?" He begged.

"What's going on?" I asked with a smile on my face.

"Look. I'm a crossdresser, ok?" He whispered. "Please don't rat me out in here."

"I'm not going to say anything." I said. "Your secret's safe with me...what do I call you?"

"Pauline." He said. "Thank you so much, Ted."

"No problem." I said as I started to get up. And then a thought came to me. "Hey. Maybe you can help me out too."

"Anything. Just please don't tell anyone." He was desperate.

"Don't make it obvious, but do you see those 5 idiots sitting in the corner booth, staring at us?" I asked.

He casually glanced around the bar. "Yes."

"Well, this is gonna sound silly but we have a bet going. The first one to pick up a woman in here wins 120 dollars. You let them think I picked you up and I'll split it with you. That way, you have something on me too. It's a win win situation. What do you say, Pauline?"

"And you promise you won't say anything at the office?" He said.

"You have to promise the same." I said. "Deal?"

"Deal. What do I have to do?" He asked.

"Nothing really. Just sit here and talk for a few minutes and then get up and leave with me. I'll pick up the cash on the way out and split it with you once we're outside." I said.

"I can do that." He said.

"Cool. Well, I can at least buy you a drink. It'll look good." I said. I flagged over the bartender and ordered each of us another.

We sat and talked for a few minutes. Paul was actually a nice guy or in this case a nice girl. And he was shy. He told me he had been crossdressing for about a year and had only been going out in public for a couple of months. I got the impression that he lacked

self-confidence. We finished our drinks and then prepared to make our exit. As we stood, he placed his arm in mine. That was a nice touch.

I could see the look of losers on their faces. As we passed the table, I reached down and took the cash. Did I feel guilty for cheating on the bet? Hell fucking no. They were assholes. Hell, I was an asshole. Once we were outside and far enough away that it felt safe, I tried to give Paul his share.

"Keep it." He said. "That was the most fun I've had in a long time. Just the look on their faces was worth it." He laughed. It was a soft, feminine laugh. He really was a cool guy.

"Can you blame them? They all struck out and I walked out with the best looking chick in the bar." I didn't mean to say that but it just came out.

His smile faded as he looked at me. "Do you mean that?"

"Um..you really do make a very convincing woman." I said.

"Thank you Ted." He said. "I guess I better head home."

"Hey, you want to split a cab?" I said. "If you're not going to take your share, may as well use it to pay your way home."

He was silent for a moment. "Ok." He said.

The cab ride was quiet. I kept stealing glances over at him. He had great legs. He really did make a nice looking woman. The cab stopped in front of his building. We said our goodnights and then before closing the door, he turned back.

"Would you like to come in for a drink?" He asked, quickly shifting his gaze to the ground at his feet.

"I would love to come in for a drink." I said. I paid the cab driver and got out.

Paul had a really nice apartment. He had a lot of artwork hanging. And not just for show. He knew the artists and their work. He actually understood art, without all the pretense.

"Can I ask you a personal question?" I said.

"Sure." He said.

"What made you start dressing as a woman?" I asked.

He thought about this for a minute before answering. "I don't know. I just never really felt right, but when I get all dressed up and made up, it feels like I fit in. I know that sounds crazy."

"No it doesn't. Not at all." I said. "And may I say, you found a really good fit. You look very nice."

"Thank you, Ted." He was blushing.

"You're very welcome...Pauline." I said.

He flashed a warm smile that would light up any room. At that moment, SHE was truly beautiful.

"Freshen your drink?" He asked.

"Yeah, I'd like that." As he took the glass, our hands brushed.

I was beginning to think of him as her. I couldn't help it. He looked like a woman. He carried himself as a woman. And he had the warmth and smile of a woman. In my mind, she was all woman.

She came back with the drink and as she was handing it to me, I took her free hand in mine, pulling her close and kissed her soft, sweet lips. She didn't pull back. I looked into her eyes. There was a hint of sadness. Perhaps loneliness.

"That was nice." She whispered.

I kissed her again, parting her lips with my tongue. She didn't resist. I kissed her deep and long. I could feel the beginning of an erection in my pants. And also, under her mini. We parted and she tried to hide a grin by biting her bottom lip. So sexy. I set my untouched drink down on the coffee table and followed her to the bedroom.

A single bulb lamp on the night table was the only light, giving off a soft glow. Even now, she was still shy. So beautiful and yet so shy. I fell in love with her there in the soft glow of her bedroom, before I ever made love to her. We slowly undressed each other, taking

our time. There was no rush. No awkward fumbling. Every movement had meaning. I kissed her shoulder as I slipped down the straps.

She kissed my chest as she unbuttoned my shirt. She unfastened my pants and took my erection in her soft hand, slowly stroking me. I unzipped her mini and let it fall to the floor. Her body was exquisite. I reached down and softly stroked her erection, kissing her slender neck.

We lay down on the bed, exploring each others body with careful, sensuous touches. She moved down and ran her tongue over the head of my cock, teasingly sucking on the head and then taking half of it's length into her mouth, moving up and down the shaft, coating me with her saliva as she continued with her strokes. When she was done, I moved down on her and kissed the pink head of her cock and her balls. Running my tongue up and down the length of her shaft. She reached for the bottle of lube on the night stand and skillfully applied it to her opening and to my cock. I pushed her legs up and pressed the head of my cock at her opening. I slowly entered her, careful not to cause her pain. She moaned.

"Yes." She whispered. "Oh, yes."

I pushed again, this time all the way in. She pushed back. She felt so hot and tight. It was like nothing I had ever experienced before.

Her breathing came in sharp bursts against my chest. I began moving in and out. Slowly at first, then picking up the rhythm. I played my tongue across the small nipples on her flat chest. She was perfect. My thrusts became faster and deeper. She met each one with equal enthusiasm. I pushed myself up so I could look at her body as I made love to her. I took hold of her cock and began jerking her off as I shoved my cock inside her, again and again.

"Yes, Ted. Oh, yes. Come inside me. Give it to me. Give it to me, baby." She said.

"I'm gonna cum, baby. I'm gonna cum." I jerked her faster. I wanted us to reach orgasm at the same time.

Just as she shot the first of her load, I exploded inside her. It was amazing. Stream after stream of my juices filled her as she shot her load onto her stomach and up on her chest. She wiped her fingers through it and licked them, then held them up for me. I tasted her love. We kissed, tasting the sweet saltiness of her.

When I pulled out and rolled off her, she went down on me and cleaned me. Her mouth was as hot as her ass. She kept sucking until I became hard again. It was my turn for the heavy breathing. I came again. This time in her mouth. She swallowed all of it and didn't stop until I was completely drained. She came back up next to me and kissed me softly. We lay in each others arms, without speaking for a while.

Finally, she looked at me. "Can you stay the night?" She asked.

"Yes. I can stay as long as you want me to." I said, pulling her closer.

We slept.

When we returned to work on Monday morning, it was business as usual. We make small talk, with each other and in groups. There are never any sly glances or even any hint that we are anything other than co-workers. Paul has his department and I have mine. We seldom have lunch together unless it's a company luncheon. But when we aren't at work, Pauline and I are together. Whether in our apartments or the occasional trip to an art gallery. She loves art and I am learning so much from her. Yes, away from work, Pauline and I are inseparable.

Our love making has become more intense. We explore each others bodies in every way imaginable. She's the perfect lover. She's quickly getting over her shyness. In our minds, there is nothing gay about our relationship. When we are alone together, she is Pauline. I treat her like the beautiful sweet lady she is. I'm the man, she's the woman. Simple as that.

I never dreamed that I would be in a relationship with someone like Pauline, but now, I wouldn't trade it for anything. She's the best thing that ever happened to me. I love her and she loves me. What more could you ask for in this crazy, screwed up world?