My New Wingman

If you are looking for a quick BDSM fix this is probably not the story for you. This is a romance with some S&M elements that are central to the plot. Many readers in romance were unhappy with the rough sex at the end and thought the story belonged here. I'm still learning the ropes, so I moved it.

*****

The woman looked up to catch me staring. Rather than smile, I feigned interest in the monitor behind her head. With her raven black hair and crystal blue eyes she was the most attractive women in the building, and she was reading the book I had absentmindedly left at home.

We were both waiting at the gate for a flight to Chicago. The flight was a modern-day cattle-car. She had planned ahead and boarded early. My plans were more spontaneous, so I boarded with a limited selection of middle seats. I made the best of the situation by finding the middle seat next to her. I might have been mistaken, but I thought she moved her bag off the seat before I asked if it was free.

"Are you going home or away?" I asked.

She told me that was traveling to the east coast for work. She was spending two nights and returning to LA on Wednesday. "What about you?"

"I'm going away for work as well, but it's like going home. I've known the people I'm visiting for a long time, so I look forward to these trips." I explained that I'd probably still be living in the Hartford area if I hadn't had to move west to be with my wife's family.

"My mother-in-law was a big help when my wife was sick, and, well, I won't bore you with the details..." I really didn't want to talk about my dead wife, but, for some reason, conversations often detoured to her.

The woman was dressed as a professional with classy, understated jewelry. She had a confident air about her that I found very attractive. Rather than dwell on my wife, she picked up the thread regarding my work "...and you still work with these people in Hartford?"

"Yes. I had to move west, but I didn't want to quit my job. They figured out a way for me to work remotely."

"You must be very good."

"I'm good enough, but mostly they trust me. When the guy I work for was sent to overseas I made sure that his girlfriend was still there when he returned."

She smiled, "What did you do, lock her up?"

"No, no, no. I kept her busy. I couldn't keep her from being lonely, but I could keep her mind off of it."

She started to play with me, "You never tried to steal his girl?" She smiled like she knew better.

"I would never do that. I was his wingman. I had his six." I must have sounded like a teenager - full of moral certainty and conviction, but she didn't seem to care.

"And when your wife got sick, it was his turn to have your back?"

"That's it," I touched my nose with my index finger.

We listened to the drone of the engines for a few minutes. I gazed out the window and wished that I'd worn something more than jeans and a white t-shirt, and I wondered if I was ready to move on with a new relationship. I then dropped into thoughts of more pressing matters. The company that I worked for, that my best friend once owned, had been bought by a larger company. I had been summoned to the grand meeting where we would all meet our new master.

"Did your wife make it?" She quietly asked.

"No."

"I'm sorry to hear that."

"Yea, thanks. She always had my six. I miss her." I looked away. She picked up her book and started reading.

Eventually, the stewardess brought our drinks.

I restarted the conversation, "So, are you married?"

"No, but, worse than that, I don't feel like anyone has my six." She stopped, "Was that my outside voice? I can't believe I just said that."

I laughed, "Don't worry. That is one of the cool things about casual intimate conversations, you can tell me anything and not worry about it. Once this flight is over you'll never see me again."

She gave a little laugh and said, "Well, I am going to see you on the next leg. I'm going to Hartford too."

I rolled my eyes, "Okay, Ms. Pedantic, after that then."

With that the conversation returned to more typical airliner fare. We discussed the book she was reading and movies that we had enjoyed. I found out that she lived about twenty minutes from my home. It seemed like we were pretty compatible, but she was so charming that she would probably be compatible with anyone.

She used her bag to save a seat for me on the flight from Chicago to Hartford.

"What will you be doing in Hartford?" I asked.

"I work for a company that buys other companies and then makes them more profitable. It's usually a win-win situation, but sometimes the transition can be tough."

My heart sank. The odds of there being two companies in transition in Hartford with a meeting on Tuesday was too small to contemplate. "What aspect do you do?"

"I'm just the messenger. I know what my boss wants, and I make sure it happens. To be honest, I hate my job. I feel for every person I fire, and I hate doing it. But my boss says that's what makes me good. My empathy helps me treat the people with respect."

I tried not to react. I didn't want her to know that our paths would be crossing again the next day.

She must have sensed something, because she asked, "You hate me now don't you?"

"Not at all. Actually, I was trying to figure out how to ask you out." While this wasn't what I was thinking at that instant, it was what I was thinking only moments earlier, and it changed the subject, so I went with it.

"I'm not looking for a relationship right now."

There was the implication that something had gone horribly wrong in the past, but I didn't pursue it. "No, don't say anything until you hear my plan. There is a little diner a half mile from the airport. You're going to have to eat anyway. Eating alone is a drag, and you like to spend time with me. So, we'll rent our cars, converge on the diner and enjoy a meal together." I indicated cars converging on the diner with my hands on the tray table.

"That sounds good," she conceded.

I stepped back let her down the aisle before me as we disembarked. As she passed me I scanned the seats to make sure I hadn't forgotten anything and saw her book in the seatback. I grabbed it and followed her off the plane.

"Here, you forgot this," I handed her the book.

"Thanks," she smiled.

"I've got you covered," I returned her smile, but I didn't see her reaction.

The diner was every bit as good as I remembered. "A greasy fry for dinner is seriously underrated," I said while mopping up egg yolk with my toast.

"I can't believe I just ate that," she said, "but I did enjoy it."

The conversation through dinner had been carefree. With the potentially disastrous meeting tomorrow I figured that we had tonight, so I made my move. I walked her through the dark parking lot to her car. She unlocked her car. When she turned to thank me I used my curled index finger to lift her chin so that I could kiss her on the lips. She kissed back for a few moments, then said, "There's no rush." She gave me her card and said, "Call me when you get back home."

"What if we only have tonight? What would you do then?"

"That is a good line," she laughed. "But I'm willing to bet that I will see you again soon." She gave me another quick kiss and drove away.

From her card I finally learned her name, Susan.

The next day I got to work early. I knew that some of the engineers arrived before dawn, so I wanted to stop in to visit. However, before I could get down to engineering I ran into Steve, my good friend and the former owner of the company. We shook hands then fell into the man-hug that had long ago become a ritual. I asked about his family, and he asked how I was doing. Then he directed me into his office and closed the door.

"They're going to terminate your contract today," he said.

"I figured as much."

"Don't panic. We will make you whole."

I knew that he would do everything in his power to cover my back. I also knew that sometimes everything was not enough, but that's not the way you talk to your wingman.

"We're solid," I said brimming with confidence.

A few moments later the office manager knocked on the door to tell me that I was wanted in one of the small conference rooms. I opened the door to find Susan sitting at a circular table reading through a file. On the table were a box of tissues and two bottles of water. I could see the surprise on her face when she looked up, and then I could see her reassembling our last conversation in her mind.

"Please sit," she said.

For the next five minutes we sat silently looking into each other's eyes.

"I suppose you know why I'm here and why we are in this room together?" She finally asked.

"You're terminating my contract."

She nodded in agreement; however, she couldn't stay in character. She said, "God, I hate this job." She was close to tears.

I handed her a tissue and gave her the best hug I could while working around the chair's arms. "You are going to be all right," I reassured her. "This is just a bump in the road. You'll get over it and be happy as a clam in no time."

"You should be firing me," she said with a pathetic laugh.

I smiled, "The thought had crossed my mind."

She had to speak in front of the whole company in just a few moments, so she pulled herself together, shook my hand, wished me the best of luck and then asked me to leave the premises. At some level I was glad to see her back in character, but mostly I was disappointed.

On the way out Steve caught me, "We are going out to dinner tonight, right?"

"Why don't we have dinner in at your house so that I can spend some time with your kids? I'll pick up a pizza."

Steve said, "I'll get dinner. Be at the house at 6:00."

That night I gave Steve's kids some gifts I had picked up that afternoon. They were flashy toys that would be broken and forgotten in a month, but tonight they were special. Kari, Steve's wife, gave me a big hug and a kiss and asked how I was doing.

"Well you know, things could be easier." I then gave them the whole story of my brief relationship with Susan. I told of the flight out, dinner and the tears in the conference room.

"Do you think you'll call her?" Kari asked. At the same time Steve said, "I wondered what had happened. She was all business when she arrived, but she could hardly put a sentence together at the group meeting."

"I don't know," was my reply.

We had a couple of beers while he filled me in on the office politics that I had trouble following when working remotely. He told me about the acquisition and how the new parent company, Hadley & Smythe, discouraged the use of contractors, which is how I came to lose my job.

"It's not over," Steve said. "The next business cycle is starting. You add the most value at the beginning of the cycle, and we're going to need you. That's your leverage; we need to figure out how to apply it."

The obvious problem was the timing. If I wanted to continue working with Steve I needed to rapidly resolve this contractual mess so that I would have enough time to get my job done before we got too far into the cycle. We discussed a bit of national politics and made economic predictions and shot the shit the way middle-aged men do. I left not long after the kids when down.

I caught the first flight in the morning. Once again I was in the last boarding group. I found Susan sitting in a window seat. She looked like she had rolled out of bed directly into her seat on the airplane.

"Do you mind if I take that seat?" referring to the seat next to her.

"Please. Please sit." she said as she moved her bag off the seat. She then straightened her hair and her posture.

I put my bags away and sat next to her.

"You knew that night at the diner didn't you?" she asked.

I just nodded.

"I'm sorry. I hope you can forgive me."

"It's not your fault." I reached out and took her hand. She responded with a squeeze.

We sat holding hands in silence for several minutes before I asked the question that had been bothering me since we had first met, "Why do you feel that you don't have a wingman? Surely you have close friends that you can count on."

She thought for several moments then turned and put her face very close to mine. She spoke softly so that no one else could hear, "When I was a little girl. Well, no, the whole time I was growing up, my mother was a belligerent, nasty drunk. She had good days, but there were a lot of bad days. My father was there for her every single day. And much later, when my mother was gone, I asked him why he stuck it out. He told me that he had hoped that eventually she would see how much he loved her and that she would appreciate him. I don't need to tell you that never happened."

It all made sense. She couldn't trust her mother, so how was she going to trust anyone else. "Ouch, that's brutal," I said.

"Now you know more about me than my best friend, Mr. Airliner Stranger that I've known for two days." She let go of my hand and turned to the window.

I could see her emotional door closing, so I said, "Look at me." I put my face close to hers and said, "That night in the diner parking lot you made a mistake by shutting me out. You are about to make the same mistake again. Think. Is that really what you want to do?"

This woman that had appeared totally together on Monday morning was a complete wreck two days later. She was about to burst into tears, so I held her close and let her bury her face into my neck. We embraced until we got to Chicago where we changed planes. Once on the ground she grabbed her bags and rushed off to the ladies room. By the time we boarded the flight to LA she was recomposed into the woman I had first met. Once again I took the seat next to her.

"You look nice." I said.

"Thank you. For someone that I just fired you are very kind."

"Don't worry about me. I'll be just fine."

"There is nothing more sexy than confidence." She gave me a big smile.

She was back in character, but I now knew what turmoil lay underneath. I wasn't capable of solving her problems, but I could show her that there were good people in the world. People that she could trust. The actual trust was up to her.

"You know, there is a silver lining in all of this. Hadley & Smythe has strict workplace romance and fraternization policies. I would not be permitted to get involved with you if we worked together."

"Wow, you guys are harsh. No external contractors and no romance. Where is the fun in that?" It took me a minute to realize that I she was actually giving me a cue to ask her out. Once I clued in I changed the subject, "Are you busy this weekend?"

"I was thinking more along the lines of dinner tonight. There is a great little place near my apartment. You have to eat, and I know you enjoy my company."

I was pleased that Susan made this parallel to our earlier conversation. "That is a much better idea." I agreed.

It was a tapas restaurant. I think the food was good, but, with the wine and Susan there to distract me, I'm not certain. We left the restaurant hand in hand. As we walked to her car she asked if I wanted to see her apartment. We kissed briefly at her car. I stopped by a drug store to pick up some supplies and met her there.

"What took you?" She asked after opening the door.

I held up the drug-store bag and said, "This way you know that you can trust me."

"In many ways we are still strangers, aren't we." Those were the last words she said before our lips engaged. She guided us to the couch, where we awkwardly collapsed while in embrace. My mind drifted to my wife and how specialized my skills had become during our years of marriage. How any skills that I might have had were withered by years of neglect. I decided to go with what I knew - slow and gentle.

I broke off the kiss and pulled back so that I could see her face. Silently and slowly I traced my finger along the line of her eyebrow, back to the top of her ear, down the back of her ear and to her mouth. She sucked on my finger for a moment, then I ran it up the ridge of her nose and stopped where I had started. I kissed her lips, then followed the same path with the tip of my tongue while she passively obliged and tipped her head as I needed.

I sat up and unbuttoned her blouse; I untucked it from her skirt and removed it. I thought about dropping it on the floor and then thought better of it and carefully put in on the back of a chair. I did the same thing with her bra. I started with my finger tips again. This time I began at her nose and moved straight down her neck, across her shoulder and down her side. She was a little ticklish so moved to her stomach, then ran my palms up the middle of her chest to her neck.

Once again I retraced the path of my fingers, this time with tiny kisses down her neck and across her torso. She was laying on the couch with me kneeling on the floor beside her. I unzipped her skirt and slid it down, followed by her panties.

"You have a beautiful body," I said as I traced my finger nail in large slow curves across her curves. She obviously worked at maintaining her appearance.

She simply exhaled as she smiled.

I lightly kissed her left nipple, licked it and took it in my mouth. She placed her left hand on the back of my head and held me there on her breast while I continued to run my left hand across her beautiful form.

She turned on the couch, straddling my body with her legs. "Will you go down on me?" she asked.

"I wasn't planning on it."

"I'm safe, I promise."

I hesitated. I'd only known her a couple of days, and my plan was for 100% safe sex.

"Please trust me."

There it was. All relationships summarized in three simple words. How could I expect her to trust me if I didn't trust her. I had no choice.

I spread the lips around her vagina and probed her with my index finger. There was a spot inside my wife that was a shortcut to orgasm. I spent a few moments trying to find it in Susan without success. I then leaned in and kissed her lightly on the clitoris. I licked, kissed, probed with my tongue and sucked with my lips. She held onto my head with both hands and pulled me into her crotch. I heard her cry softly and then she released her grip.

"Thank you," she said pulling me up by my t-shirt. She pulled off my pants and gave my cock a few quick strokes. Without hesitation she took me into her mouth. For a few moments she gave me the conventional blow job that I expected. She licked the tip and twisted her lips around the crown of my penis while fondling my balls in her hand. I held onto two clumps of her hair and encouraged her to go further. She slid her hand past my anus up towards my lower back and without warning she pushed my pelvis forward and deep-throated my entire shaft.

"Oh fuck!" I howled as I unloaded in her mouth. My body quivered as pleasure coursed through it.

At breakfast Susan asked me, "Will I see you again?"

I found the question disturbing. "Why wouldn't you see me again?"

"I don't know. I guess I have baggage."

"Oh, don't be like that. I'm going to go home, but I will be back here tonight for dinner."

She smiled, so I thought everything was fine.

On the drive home I thought about how we had destroyed the shield of anonymity that would have made our casual intimate conversations meaningless. We were left much more emotionally connected than would have possible on a conventional first date. I felt like I owed her my loyalty simply because she had exposed her broken soul. At the same time, I knew she was damaged goods and that she would test and retest any trust that we were able to build. I hoped that I was up to the challenge.

I spent the day trying to bolster my negotiating position with Hadley & Smythe. Steve suggested that I work on the proposals he needed for the business cycle. He planned to press Hadley to restore our contract and thought that I could use the proposals as leverage in the negotiations. I'd already done a lot of preparatory work, so Steve's approach made sense.