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Funny You Should Ask


When I walked into the bar on Friday, I spotted Jack almost immediately and went over to hug him in that awkward way that men do.

"Damn, Jack," I exclaimed, "It's been ten years and I still recognized you immediately -- you haven't changed a bit."

"Neither have you," he replied. "I heard you got married. It looks like married life agrees with you."

We found a booth in a quiet corner and ordered a couple of beers.

We'd been roommates and good friends in college, but after graduation we'd both gone our separate ways. Jack had taken a job in another city; I'd stayed in Chicago. We'd pretty much lost touch with each other until I learned by chance that he had moved back here a couple of years ago to take a job in commodities.

"So what about you," I asked, "why haven't you gotten married?" I recalled that Jack had played the field pretty actively back in college. He never had trouble finding girlfriends but he never seemed to keep them for long.

"I guess I'm not lucky like you," he said, with a smile, but I thought I detected a hint of pain in his eyes when he spoke.

I tried to lighten the mood. "That's the trouble with you playboys," I kidded. "Once you start playing the field you can't stop."

It was clear from his expression that my teasing touched a nerve. He shook his head glumly. "Oh, I've tried to find a wife alright, but when it comes to that I've had the worst luck in the world."

"Any close calls?"

"Funny you should ask," he said.

I could tell something was really eating at him so I settled back in the booth and said, "Why don't you tell me about it."

He signaled the waitress to bring us another round, and after she had done so he began his story.

- - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -

It all started about a month ago. The day started off crazy, which is normal in the commodities market. But around mid-morning my boss walked in with a woman in tow. "This is Carla," he said. "She's going to be working in your area. I'd like you to show her the ropes, help her get started."

I have to tell you, something happened to me when I looked at her. I've dated a lot of attractive women, but not one of them ever had the impact on me that she did. It was odd: she wasn't model-quality beautiful and her clothing wasn't particularly revealing, but something about her just bowled me over.

I've never believed in love at first sight or the idea that there's only one woman for a man. But Carla made me feel like a teenage boy smitten for the first time. It was amazing and disconcerting, and I felt completely helpless.

I sat down with her to go over some of the things she needed to know about working here. It didn't take long for me to see that she was very bright as well as outrageously attractive. That's a combination that's always been appealing to me. As I talked to her, I tried not to stare but I don't think I always succeeded. It didn't seem to bother her: she just listened intently to everything I had to say, making notes on her pad.

After I'd spent a little time with her, I suggested she work on her own a while. "Then we can grab some lunch together and I can answer any questions you may have," I told her.

Normally I don't date in the office -- that's just inviting trouble. But I already knew I was going to break my rule in Carla's case.

I hoped to learn more about her over lunch. I'd already checked: she wasn't wearing a wedding ring. Iit looked like she might have done so in the past, however, so I figured she was divorced. But I didn't learn any more about her while we ate because all she wanted to talk about was me and what I did at work. When an attractive woman keeps asking questions about you, it's hard not to feel flattered, and before I knew it lunch was over. Even though I hadn't gotten to know Carla any better, I'd enjoyed being with her immensely.

Things started going sour that afternoon when Hank Malone walked in. Hank is my biggest rival at work. We were hired at the same time and our careers have moved in parallel. But Hank doesn't see it that way. He's always bragging about his accomplishments and he always has some big deal working that's going to earn him a fat bonus. His egotism isn't limited to work, either. He likes to boast about his sexual conquests, and he has no qualms about dating people at work. From what I can tell, he's cut a swath through the women in the office and left a few broken hearts in the process.

So I wasn't happy when Hank suddenly showed up and introduced himself to Carla. "Anything you need to know, just come to me," he boomed in his big voice. "I'm in tight with senior management, so if you need anything, I can arrange it."

I ground my teeth at his obvious ploy, but I couldn't think of anything I could say that wouldn't make me sound like a jealous schoolboy -- which is about how I felt. What's worse, Carla seemed to eat it up. She thanked him profusely and promised to call him.

Trading commodities can get pretty intense, and it's common practice for many of us to stop in at a nearby pub after work to unwind before heading home. I mentioned it to Carla, and she agreed to come along. So after we'd reconciled our trades for the day, I led Carla to our favorite watering hole and introduced her to the rest of the gang.

Everything was going fine until Frank showed up. He forced his way through the group, sat down next to Carla and proceeded to monopolize her attention. Even with all the noisy chatter in the pub, it was easy to hear Frank boasting about himself and his rosy prospects. To add insult to injury, Carla seemed to be hanging on his every word.

But before she left, Carla did lean over and thank me for making her feel so welcome on her first day at work. That made me feel a little better.

The rest of the week went on much the same way. Carla and I didn't eat lunch together every day, but we'd often take a coffee break together. Likewise, some days Carla didn't come to the pub with us, but when she did she was an avid listener, interrupting only to ask an insightful question.

Of course Hank continued to hover around her like a bee around blossom. It had to be evident to Carla what he was after, yet she made no attempt to discourage him. I was the one who was becoming discouraged.

He and I happened to use the restroom at the same time one day, and he didn't miss the opportunity to assert his claim on Carla to me. "I've got her eating out of my hand," he crowed. "It won't be long before I'll be giving her a tour of my bedroom, if you know what I mean," he said with a leer.

In an odd way, I found Hank's boasting reassuring. The way he talked made it clear that Carla hadn't yielded to his persuasive abilities, and that made me think I still had a chance with her.

In fact, I felt like my relationship with Carla was progressing, though it did so in an odd fashion. For example, at first she showed an intense interest in me, my work and my lifestyle, always encouraging me to talk about myself. She probably knew more about me than some old girlfriends I'd dated for months. Yet despite her interest she seemed restrained and cautious around me, as though she couldn't let down her guard. I drove myself crazy trying to figure out what I had said or done to cause that response.

But after a little while, much to my relief and delight, her attitude seemed to change significantly. She began to relax and appeared to feel much more at ease with me. I started to pick up some of those little signals a woman uses that say, "I'm interested; I like you."

All that would have been very encouraging, except for the fact that she continued to devote way too much attention to Hank. I couldn't understand it: we'd be having a great little conversation and then Hank would show up and she'd drop everything to listen to him. Of course Hank never missed an opportunity to rub my nose in how much time Carla was spending with him. "Face it, buddy boy, you may be her work pal, but she digs me! I'm going to have my nose up her skirt in no time, just wait and see," he boasted. I didn't believe him, but I couldn't deny that Carla seemed to divide her time between the two of us.

I'm not inept when it comes to women. I know how to make them laugh, to flatter them without being obvious, to flirt without being crude, and in general how to interact with them in such a way as to keep their interest. I don't mind admitting that I used all my techniques on Carla in an effort to build her interest in me. In the past when I've done that, it has been sort of a game to me. But with Carla it was deadly serious. Before I hadn't cared that much whether I won or lost; now it felt like a matter of life and death, and I desperately wanted to keep this relationship alive.

What made things even more confusing was that all the usual signs I picked up from her told me that my efforts were working, that she was responding positively to my romantic offensive. But she still wouldn't give up on Hank.

One day I learned from my sources in the office that Hank had asked Carla out and had been turned down. I decided that it was time for me to take my own shot. If nothing else, I hoped I could get a read on whether Carla really had any interest in me or not. So late one afternoon I wandered over to her workstation. "Hey, Carla," I said casually, "why don't you and I go grab a bite after work?"

"Like with the gang at the pub?" she asked.

"No, just you and me," I said. "I've got some things I want to talk over with you, and the pub's too noisy."

"I don't know if that's a good idea," she replied hesitantly.

"It's just the same as though we were going out with the rest of the gang," I reassured her, "it'll just be a little easier to talk."

"Well, okay," she said, and I had to struggle to keep myself from jumping up and down with excitement at the prospect of getting her all alone to myself.

I took her to a great place nearby: very quiet and low key, candles on the table, nice but not too fancy. Over dinner we talked about the office and our responsibilities for a while. Then I gradually shifted into a discussion of how well she fit in with our group, what a great contribution she was making to our work output, and how well everyone liked her. I could tell that that pleased her.

Then I went on to talk about how much I enjoyed working with her, how she made work go easier, and what a nice smile and laugh she had. "The thing is, Carla, that I'm having trouble thinking of you as just a colleague," I told her sincerely. "I really want to get to know you better because I'm starting to have feelings for you."

She gave a little "Oh!" and reached out instinctively to grab my hand and squeeze it. But then she got a conflicted look on her face and released me. "I like you a lot too, Jack, but I don't know if this is a good idea. There's a lot about me you don't know, things that might make you feel very differently about me."

Now I was the one who reached across the table and took her hands in mine. "I don't care about whatever's in your past," I said earnestly. "I see you every day at work and I know the kind of person you are. I also know how I feel when I'm around you."

Her eyes burned brightly, and I thought for a moment she was going to come across the table and seal the deal with a kiss. But at the last moment she seemed to regain control of herself, and she drew back. "I can't deny that I've been thinking a lot about you too," she said, "but this is all happening too fast for me to process. Please don't press me, give me a little time."

I looked into her eyes. "I'll wait as long as you want," I promised. "You're worth waiting for."

Once again I thought she was about to say something, but once again she restrained herself. Not long after that she left for home. "Did I just make a giant step forward or blow it completely?" I wondered as I got a cab back to my condo.

The next day, of course, she went out to lunch with Hank, and I ground my teeth in frustration as I ate a sandwich at my workstation.

On Friday night we were all back at the pub and the drinks had been flowing a little more freely than normal in celebration of a very successful trade we'd managed to pull off. As the evening wore on, more and more people began to drift away until Carla and I were the only ones left.

I guess I'd had more to drink than I'd realized because I found myself doing what I'd promised not to do: putting pressure on Carla.

"You don't know me," she said with a bit of a slur in her voice. "I'm not the woman you think I am."

"I know exactly what kind of woman you are: you're the most amazing, attractive woman I've ever met, and I can't help wanting more of you," I said firmly. Then, in a mix of emotion and intoxication, I grabbed her by the back of the neck, pulled her to me and kissed her firmly on the mouth. For a second she resisted, then her whole body seemed to surrender. She leaned into me and returned the kiss with equal fervor. Our tongues explored each other and we reveled in the sensuality of the moment until some wise guy at another table made a crack about getting a room.

Carla pulled back and looked at me agitatedly. "Jack, I've got to go." Hurriedly, she dashed off, leaving me sitting there to wonder what had just happened. Whatever it was, I decided, I was more determined than ever. That kiss told me more about her real feelings than anything else she might say or do.

The next week I gave her space, hardly speaking to her at all. Several times I caught her glancing at me, but I acted as if I hadn't noticed. Let her feel what it's like to be uncertain about what's going on, I thought.

I decided I would make my move on Thursday, and she made it easy for me. She came to see me after lunch, and it was clear that she was not the confident, capable woman I was accustomed to seeing. "Um, Jack, about what happened last Friday, I'm sorry if I . . ."

"Not here," I interrupted her. "If you want to talk, let's do it over dinner."

I'd caught her off balance, and she hesitated a moment. Then she seemed to make a decision and her eyes signaled acceptance. "Alright," she said, "over dinner."

I didn't reply, but inside I was jubilant.

When the work day finally ended, I walked over to her workstation. "Are you ready?" I asked curtly, and she meekly nodded. I took her by the arm and led her out of the building to the curb, where I hailed a cab. She got in without hesitation and we rode in silence most of the way. Finally she looked around and asked, "Where are we going?"

"To my place," I told her. "I'm going to cook dinner for you."

She nodded as though this was what she'd expected all along.

When we got to my building, I took her arm and she let me lead her without protest. We rode up the elevator in silence. When I let her into my apartment and closed the door behind her, she looked at me with a combination of acceptance and expectation, and I had no choice. I took her in my arms and kissed her passionately. If anything, she returned the kiss with even greater passion.

Then we were tearing at each other's clothes, desperate to make as close contact with each other as humanly possible. With each piece of apparel she shed, the body she revealed confirmed the sensual promise I'd known was in her from the first time we'd met. She was, to put it simply, the most desirable woman I had ever seen. Oddly, it wasn't her breasts, her hips or her legs that excited me most; rather it was the combination of them all that created such a supremely enticing woman.

We left clothes strewn all over the floor as I led her to my bedroom. Once there I laid her on her back on my bed and proceeded to trace kisses over every square inch of her body. At first she lay there quietly, yielding to my desires. But soon her breathing accelerated, and then she began to pant as desire and sensation mingled within her. The musky smell of her arousal filled the air. When my lips suckled her breasts, she started to gasp, throwing her hands above her head in an act of surrender.

As I slid down her body to the juncture of her thighs, her body arched involuntarily, and when I licked her lower lips she groaned out loud. I gave her no relief, gently probing and licking all around her moistening pussy. Her sighs turned to moaning as I pressed on. When her moans became continuous, I began to circle her clitoris with my tongue, causing her hips to arch up to my face. When I thought the time was right, I flicked the tip of my tongue back and forth rapidly on her clitoris while inserting two fingers deep in her pussy and stroking her g-spot. "Oh my God, what are you doing to me?" she cried out. When I wouldn't stop, her hands grabbed the bedspread and held on for dear life while her body rose up as if in supplication. For long seconds no sound issued from her throat; then she gave a loud shriek and collapsed back on the bed. I continued to lick her gently, and my fingers felt repeated contractions as aftershocks ran through her.

When she finally calmed down, I got up on my knees in front of her, bending her legs back to facilitate my access. I took my cock and rubbed its dripping head between the lips of her pussy and up over her clitoris. "Oooh, keep doing that," she moaned as the sensations roused her from her post-orgasmic lethargy. I continued and her hips started to rock again as her pussy hinted that another orgasm might be possible after all.

When her hips began lifting in time with my sliding motion and her moans matched my rhythm, I pushed down just a little and the head of my cock embedded itself in her entrance. "Oh, yes!" she gasped, and her hips began to buck even more, enough to cause me to slide in to the hilt. When she felt me deep within her, she reached up and grabbed my head, pulling me down to kiss me. "I've wanted this for so long," she gasped as I began a smooth, rocking motion.

After a few minutes I raised up and began to thrust more powerfully into her soft clinging depths. "Oh, oh, oh!" she moaned as I kept changing the motion, never letting her predict exactly what I would do next.

To tease her I pulled out and began rubbing my cockhead over the outside of her pussy again. "Oh, please," she begged, "put it back in me," and she began tugging at my hips to try to get me to embed myself again.

When I was ready I grabbed her legs and lifted them up so they were resting on my shoulders. Then I leaned forward, pushing her legs back towards her shoulders so that her pussy was totally exposed and vulnerable. When I had her where I wanted her I thrust back inside and began to piston in and out with greater pace. "Right there," she yelled, "Yes, just like that, keep doing that!"

I knew that my cock head was rubbing her g-spot, and I bent her further backward to increase the friction. Now her voice took on a new urgency: "Oh, God, you're going to make me cum again!"

I felt the pressure build up inside me and knew that I couldn't hold my own orgasm much longer, so I began to pound into her. Her grunts and gasps sounded like the kind of noises an animal might make. Just as I felt myself hitting my peak, she gasped out, "I'm cumming, I'm cumming!" and screamed at the top of her lungs. Then all the tension seemed to drain out of her body at once and she fell back limply on the bed. I collapsed on top of her, clutching her to me to try to maintain that incredible sensation as long as possible. Finally I rolled off beside her in exhaustion.

We lay there side by side for a minute or two, and then I turned toward her and began kissing her gently. She returned my kisses greedily, and we cuddled together for quite a while.

Then I rolled away and got off the bed. "Wait here," I told her and went to my desk in the living room. When I returned I was carrying a small box. "This is for you," I told her.

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byFrancisMacomber© 153 comments/ 108379 views/ 64 favorites

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