Bored (MF)

A deal takes an unexpected turn to the delight of all.

Steve was working late with a client and I was bored. Don't take that wrong, Steve has always worked long hours to provide for us and as a result our family was always well taken care of. It's just that Julie our youngest daughter had moved out last year and the whole empty nest thing was hitting me pretty hard. I was still young enough to work, but I had never really gotten started, having spent so many years being Mom to our beautiful daughters. Jennifer was born when I was 20 and Julie was born two years later, so at 43 I was now without purpose really for the first time in my adult life.

Finally, around 8pm I called Steve's cellphone. "How's your evening going, honey?" I asked. There was the normal level of background noise, but I could tell he was getting tired. "Great, great. Gary, the CEO for J&C is quite a guy. I think I can get this deal done tonight. We're going over to his hotel to wrap things up over a nightcap in around 10 or so."

That was great to hear. "Good. I guess you'll be home by eleven or so, then, huh?" I asked a little selfishly.

"Uh, yeah, maybe. If I can get him to commit by then. He just seems to want to talk. I think he's lonely. It's just taking longer than I expected." Steve complained.

Steve had told me a little about Gary Jones, the CEO of J&C and so it did not surprise me. Gary had been running his design company for almost 40 years, pouring his whole life into it. That level of focus was great for a business but was a killer of any kind of balanced personal life. Only now as he was beginning to look at his dwindling future was Gary beginning to feel the loss of all the years running the business. That was a large part of the reason he was meeting with Steve. As the acquisitions manager for Palmer, Lee, and Kelly, Steve Kelly was looking to buy J&C from Gary. If Steve could close this deal, he would no longer be a junior partner, but a full partner in the firm. This was important.

Suddenly I had a very wicked idea. "Honey, where are you going for the drinks again?" I asked.

"He is staying at the Plaza, so I am guessing we will just hit the Oaken Ram in the lobby." He replied.

My mind was beginning to race as I asked "Steve sweetie, I have an idea that might close your deal faster and fits one of your fantasies, but you are going to have to go along without interfering. Can you do that?"

There was a brief pause on the line, before he agreed, and I told him I would see him soon before hanging up the phone.

The plan that had developed in my head while talking with Steve was that I was going dress up and give Gary a little attention. With any luck he would be willing to finish with Steve to have drinks with me. Undressing I took a quick shower. In the bathroom mirror as I toweled myself dry and took inventory. I still attended my classes at the fitness club and so was still in good shape, and at 5'10" tall cut a nice sharp figure. Dressed nicely in one of Jennifer's old dresses, I'd look younger than 40. There wasn't any fat reflected in the mirror. Throwing on a robe I headed upstairs to Jennifer's old room.

The room was unoccupied, as Jennifer had taken her first job in Boston last year, but she had not really moved out there yet. Walking into the closet I began looking at the variety of dresses hanging there. Moving along to the back I found the ones I was looking for. These had been used during the college "formals" and parties that Jennifer had loved before graduation. I found a nice conservative one in a light brown that looked perfect and was about to leave when another one caught my eye. It was black and silky with almost no designs or embellishments. The neckline was low and the cut was sleek, the whole thing screamed sexy. It would be a tight fit. "Oh why not just look" I murmured.

Downstairs the brown dress fit and looked just fine. No panty lines or unsightly bulges, and the overall look as smooth and appealing. The black dress was a bit more trouble but had some major advantages. The fit was excellent with the neckline giving me an amazing cleavage, but the silky material and close simple cut made every line show. Replacing my current bra with a black no-show eliminated the bra lines, but even my thinnest panties showed through the dress. The only way I could wear the black dress was like I was now, without panties at all.

I parked my car in the hotel's garage and walked into the Plaza. It was a little before 11 when I walked into the Oaken Ram. Two guys were coming up the stairs as I was going down and stepped aside as I passed. Both stopped and watched me walk past. A quick look around indicated that Steve was settled at a table, with an older man - that must be Gary. They were settled into their table with drinks and deep in conversation. I could tell that Steve was tired and that he had not noticed me yet. I walked over beside the ladies' room and called Steve's cell phone, suggesting he come meet me in the lobby.

I watched as Steve hung up and excused himself from the table, quickly heading out of the lounge and to the lobby. Once he was gone, I walked into the main area and towards the now alone Gary. "May I join you?" I asked the startled executive.

"um sure, please" Gary muttered in surprise.

Siting down I pulled my chair over a little nearer to him and asked "So are you here alone?"

Gary was older probably in his 60's, with a bald head and a body weighed down with the results of long hours over many years behind a desk. He was not an attractive man and in most situations, I would have never approached him.

"Well yes, I mean no. I'm actually finishing up some business." Gary finally stammered out.

"Finishing? Oh that sounds promising. Would you like a little company this evening?" I asked. Then leaned in close and whispered, "Or maybe you could hire me for a little celebration when you're done?"

Gary's face grew red and for a moment I was afraid I had misjudged the man and his needs. "Oh um, yes, I mean please." Gary said in a rush.

"Wonderful!" I squeaked "Should I join you now or later?" I asked.

After a moment's thought Gary leaned in saying "Can I call you back here in about 20 minutes?".

With a nod and a smile, I stood and walked behind Gary to a table in the back of the lounge. I saw Steve walk back into the lounge looking aggravated. When he sat back down, he was facing in my direction with Gary's back to me. I watched Gary talk quickly and gesture in my direction. The look of surprise on Steve's face when he looked up and saw me was truly priceless, especially as I winked back at him and smiled.

Watching the two men deal now was fun, as I could tell Gary was anxious to be finished and Steve was a little distracted. While I was watching a drink appeared in front of my face held by a man's hand.

"Hello there beautiful." A deep voice said. "Are you busy tonight?"

Taking the drink, I smiled at the man, he was tall and quite handsome, mid to late 30's, well-built and dressed impeccably. "Unfortunately I am" I murmured with a note of disappointment.

With a sad, but resigned smile, he dipped his head slightly saying "That is a shame, I am Javier and maybe I can get a raincheck for later?"

My smile widened as I replied "Absolutely." As he wandered off I couldn't help but smile as I watched him go.

It was only a matter of a few more minutes and a couple of drinks before both of my men were shaking hands and slapping backs. As I watched Gary turned around and waved at me to join them. "Steve this is..." Gary started, then paused... "Joan" I added quietly. "Yes, yes, this is Joan and she is here to celebrate our deal." Gary finished.

Steve's look was shock as I took his hand "Very nice to meet you sir"

"Now that my business here is through, I hope I'll have some time to relax." Gary stated as he wrapped his arm around my waist.

Smiling I asked "Oh, what business are you in?"

There is no better way to make a man feel important that to let him talk about himself and his business. Gary launched into a long discussion of his firm and what they do and how he built it.

"That sounds fascinating. " I said as he went along. Several drinks later and it was clear that Gary was feeling a little more relaxed.

When he excused himself to use the restroom Steve leaned over and quickly whispered "I don't know what you are doing, but it worked. Deal is done and on great terms." Steve's joy was clear, but also his confusion. "Now can we get out of here?"

I smiled at him "Sorry I can't dear. " I whispered. "You know how you wanted to me to loosen up, well tonight I have a customer. Oh, and by the way... I'm not wearing panties and I'm doing whatever he wants tonight." The warring looks on Steve's face were priceless but fleeting, as he saw Gary leave the restroom and head back to the table. By the time he returned Steve was once more in control.

"Steve and I are celebrating a deal." Gary said as he sat down and moved his chair a little closer to mine. Drinks and conversation flowed. Gary was getting pretty tipsy and the more he drank the more 'familiar' he became towards me. His hands rubbed my back, touched my hair and roamed over my bare legs. The room was dark and at one point I unobtrusively hiked up the edge of my dress. Gary almost choked when his hand touched my bare thigh and wandered to where my panties weren't.

Steve was bothered, but not in a jealous or negative way, so I leaned over and snuggled myself into Gary's arm. Steve masked his discomfort by rising and announcing "Lemme get another drink here for us." Then heading towards the bar.

Leaning over I whispered into Gary's ear "Com'on, Gary. Let's go upstairs." Gary turned to me. "Okay." Together we rose, me pulling my skirt back down as discreetly as possible and walked out of the lounge.

The two of us got to the elevator and when the doors closed, Gary turned to me. "You're one beautiful woman, Joan. I'm glad you're coming up with me."

He held my hand, and I pulled him closer, into an embrace. "I'm $500 beautiful for you tonight, payable in advance." I whispered back to him. With a smile he stepped back and handed me 5 crisp $100 bills. As he handed them to me, I pulled him close. He was shorter than me, so as his head moved toward me, I tilted mine down, and our lips met. His tongue pressed against my lips, and I allowed it between them, and just like that I was kissing a man the way I had only kissed my husband. In a moment I was in his arms, passionately kissing this stranger. Gary's hands cupped and pulled my buttocks, pulling me hard against himself. The material was so thin it felt like his hands were touching me directly as he groped. In a matter of minutes, we were at Gary's suite.

"Joan, you're really beautiful." Gary muttered as he opened the door to the suite. He settled on the couch, and pulled me toward him, turning me, so I was laying back in his lap. He lifted me, until our lips met. Again, lips touched, opened, and tongues touched. "You're an exciting woman, Joan" he said, holding me with one hand, while the other caressed my check, then my neck, and throat. It reached the top of my breast, and I lifted up, my arms around his neck, kissing back, as that hand went lower, until it found my nipple poking out through the material. He was touching my breast! Was I really doing this, this whore role, the plan had been to simply distract him to finish the deal, but every step towards this had been more enticing, more erotic, but would I actually go all the way with this old man? I could feel my excitement growing. " You feel so fine..." he mumbled and there was another kiss. The kiss continued as I felt his hands slide down the front of the dress. I could feel his finger slide over my stomach and over my barely covered groin. His fingers pulled and soon I felt his bare finger touch my shaved mound. Then it reached further and with a jolt another man touched my clit. I knew I was already wet, but I could also feel I was already aroused as well. Gary's fingers flitted and touched, wrapping themselves around my desire. As our kiss broke I could see the redness of Gary's face and the concentration there as well.

"Kneel on the floor, Joan." Gary said.

I pulled myself up and knelt on the carpet before the him as he stood.

"My belt, Joan, undo my belt." Right there in front of me was his crotch. He used his hands to grab at his belt, helping me get it released, and then the buttons holding his pants together. "You do the zipper, Joan."

I did do the zipper, while he unbuttoned the lower part of his shirt. Then with both hands on his waistband, he pushed down. His hard penis was in front of my face. He put a hand on the back of my head pulling me toward that swollen organ. "Take it, Joan.". I felt pressure against my lips, and I opened my mouth to accept Gary's cock. Both my hands went to the penis in my mouth, one holding the shaft, the other reaching under, cupping his scrotum. I did this to other men before I was married, but that was so long ago, this all seemed so new, so strange, so exciting, with this stranger, who didn't know who I was. My own eyes were closed, now, but I knew Gary was holding my head to him with one hand, and the other seemed to be fondling my breast.

"Let's go to the bedroom." Gary said and he pulled me to a sitting position, and then - it had to look ridiculous really, with Gary holding up his pants with one hand, and me with the other, tripping over clothes, going into the bedroom. Gary released me and pulled the cover and blanket off the bed. It looked ridiculous as I watched this fat old man drop his pants and get his shirt unbuttoned, and off. Then turn me and unzip my dress allowing it to fall soundlessly to the floor, followed quickly by the minimal bra.

He was not attractive; in many ways he was repulsive. Short, overweight, pasty, out of shape, and old enough to be my father, but I didn't care. I was standing naked in front of a man who was not my husband and I was willing to do whatever he wanted, if he only knew to tell me.

"Get in the bed, Joan." I did. "This is how I consummate a deal in my dreams," Gary said, reaching toward my knees, pushing them apart, and moving between them. I watched as he moved into position, between my legs, his cock throbbing. He leaned forward, supporting himself with his hands on the bed beside my chest. And paused. "I'd still like to see this cock in your mouth." Gary said, as I reached one hand for his shaft. I found his cock, posed above my pussy and spread my legs a little wider. Holding his cock I moved it, up and down, so that his cock head stoked my vulva, just as his fingers did moments ago. I lifted my head, looking down, along my body. Gary's cock was poised at my crotch.

He moved, and I felt increased pressure, then that sensation of entry, of spreading, of penetration. I looked down to see our pelvises merged, I could feel him in me, moving. What was Steve doing? What was he thinking? "That's what adultery feels like," my mind whispered. Gary's mouth was open, his face red - with excitement. I reached up with both hands, pulled at his face, bringing him closer. He was excited. I could feel his cock throbbing. I lay there, legs spread, as Gary pumped into me. He was ramming into me - he didn't care about me, I was something to fuck - only his pleasure mattered to him. I felt trashy. And excited, too.

"Oh fuck" Gary muttered, his own climax about to happen.

"Oh yes" I groaned, loving the feel of his cock in me. I had not tasted another penis for so long... or felt another man touch me, nor had ever been with a stranger like this! Heaven! My hips were pushing onto Gary, his penis, a stranger's penis, in me. I was doing it - - being a prostitute. Acting out what I wanted. Not acting - doing it! My body shuddered - orgasming, already! I actually came!. At the same time Gary erupted - it was sensory overload for me. I could feel each twitch of his penis as he shot his load into me, pressing hard against me, trying to bury his seed deep into me. Then it was over and Gary seemed to collapse across me, both of us panting and sweaty and just trying to breath.

I fell asleep and so did Gary apparently. It was dark and the room was cold when I awoke, but I stood and found my bra, shoes, and dress, before slipping into the bathroom. A few minutes of work and I looked at least presentable. Quietly I opened the room door and slipped into the hall. The elevator was quiet and the hotel was almost deserted.

As I walked past the front lobby a familiar face appeared. "Good evening beautiful. We meet again." Javier said.

I paused in the lobby and smiled at him. "Javier, what a surprise. I am unfortunately not at my best at the moment." And I laughed self-consciously.

"Don't be ridiculous. You are stunning... besides I have a raincheck to claim." The charming man said with open arms.

"Really? With me looking like this?" I said. "I'm not really in my best condition to work."

The smile on Javier's face never wavered. "Perhaps then a discount?" I could claim it was exhaustion or alcohol or whatever, but the truth was I wanted this stunning man and so I smiled and nodded my head.

Once again in the elevator I smiled and said "What do you have in mind Javier?"

"Just the 'unusal'... and you did mention a 'discount'?" The smile on his face was all play and fun, but it was also wonderfully arousing. The allure of this illicit encounter, this paid relationship meant it wasn't real.

"$300 for what evening remains?" I asked him "In advance." I added.

The smile never left his lips as he pulled out his wallet. As soon as I had taken the money, Javier took my shoulders and drew me into a kiss. It was hard and his tongue was strong and insistent. Once in his room he stopped with me in the center of the room and pushed me down to my knees as he unfastened his jeans. The cock that emerged was thick and long and throbbed before my eyes. With both his hands on my head he pulled my face towards his cock. My mouth opened wide as he pushed it in. He stood still as I pushed it into and out of my mouth, rolling my tongue around it with each stroke. Steve's cock was long, but it was thin, this cock was not only as long, but thicker. Pushing forward I was able to take it all, pushing it deep into my throat and burying my face in his thick brown public hair. He smelled like cologne and soap. As I started to pull back, his hands stopped me and I held my breath as I felt his cock begin to swell. "Urrgh" he groaned as his cock pumped shot after shot into my mouth and eventual belly, as I struggled to swallow his load. Finally, he seemed to stop and withdrew enough for me to take a coughing grasping breath. My eyes watered as I looked at the still throbbing cock in front of me.

Javier's hands reached under each arm and lifted me from the floor, laying me back onto the bed. I laid back and he pushed up my dress revealing my lack of panties. The flip was sudden and unexpected as I found myself face down on the bed, his hands pulling my hips back and up. I could feel his fingers poke into my vagina, feeling the wetness there, then I felt his hands on my back, moving between my buttocks. There was a jolt and his fingers moved over my anus. And his finger pushed in there! "You're not going to. . ."

I started to say, but he interrupted in that damn deep voice. "Oh, but I am. " And his finger was replaced with the pressure of something bigger, pushing, forcing, his actions forcing me down. The pushing blunt force changed to a stretching one, almost painful, and then that full feeling, as he moved into me, into my ass. I was glad he had come before - if he were as horny as he had been, as hard as he had been, as big, I'd be torn apart. Javier had his hands around my hips, as he pushed into me. His actions overwhelmed me, and I tried to collapse flat on the bed. Javier held me up and continued to pound me, then he stopped, and without warning pulled out of my ass and plunged into my vagina, driving me down onto the bed at last. Pinned there by his weight he began to pound with a renewed vigor and energy. Each stroke slammed into me, filling me, reaching the very bottom of me. Deep powerful and sustained thrusts filled my mind and body with a charging passion. I pushed back for each stroke trying to pull him in deeper, to trigger that climax that I was building towards. He shifted and pulled my hips up higher as he once again rose behind me. Each stroke was deep and now he could reach even deeper.