Weekend in Indy

I loved the early morning. I took my seat in the first class section of the 6am Northwest flight from JFK to Indy. Although the jet was full, I hoped that the window seat on my right would remain empty for the flight. However, that was not to be. Shortly before the doors closed, an older, attractive professional couple stepped into the plane. They greeted the flight attendant and glanced at their tickets. "See you in Indy," the woman said to her companion. He grumbled a reply and made his way to the coach section of the aircraft. She walked confidently to my row.

"I'm in with you," she said.

"Good morning," I answered, "let me help you with your bags."

I helped her store her luggage and briefcase in the overhead storage and watched as she made herself comfortable in the window seat. I guessed she was fifty-five, twenty years my senior. She had auburn shoulder length hair and was toned and athletic. Five foot four, 110 lbs. She wore a sexy white tee and a worn knee length jean skirt. I noticed a hint of a rather large nipple was topping 34 C cup breasts. She had a large diamond and wedding band on her left hand.

I liked her smile. It was genuine and showed off her mature all-American features.

As I settled back into my seat, I extended my hand and introduced myself, "I'm Christopher."

"Hi Christopher, I'm Jackie, nice to meet you." Her hand was soft and her grip firm. I liked Jackie.

"Your friend doesn't look happy to be in coach," I observed.

"That's Donald, my husband. He's grouchy because we couldn't both be upgraded to first class. We flipped a coin. Heads I get first class, tails Donald gets coach." Jackie and I both laughed at her joke.

They were heading for a weekend long trade-show in Indy and would be away from Thursday to Sunday. I told her I was just going for two days. "I have meetings both days, a dinner Thursday evening. I'm solo Friday night and fly home Saturday morning.

Jackie was easy to talk with. We explored all the normal areas, including spouses, children, jobs and the like. I thought her face was very pretty. Especially, for a woman old enough to be my Mom. Her blue eyes sparkled as she talked. Her lips were a bright red and I imagined my cock sliding between them.

I tried to get comfortable and crossed my left leg over my right. I didn't realize it, but Jackie had started to excite me. I was wearing a pair of lightweight dress pants. The outline of my thick eleven-inch cock was clearly visible as it extended along my left thigh. I was going to rearrange myself, when I noticed Jackie staring slack-jawed at my dick. Women are so predictable. All go through the same process when they first see my dick. Disbelief turns to wonder and eventually to animal lust.

We chatted for the entire flight. Jackie's eyes constantly darted to my semi-hard cock. She didn't care when I caught her staring. I could tell she was excited and wondered if she would act on her most basic instincts.

After landing, Jackie, Donald and I walked together through the airport to baggage claim and then to the Hertz pick-up area. Donald asked, "what are your plans for the evening?"

"I have an early evening reservation with a customer at St. Elmo's, a local steakhouse. After that, I'm on my own," was my response.

"We're going out with a group of associates. Would you like to meet us at Howl at the Moon? Its a downtown piano bar."

I pretended to think about it and said, "I'm not very comfortable with strangers. I think I'll just head back to my hotel." I could see disappointment in Jackie's eyes. We shook hands and went our separate ways.

My day was non-stop and filled with three grueling meetings. At dinner, I was able to relax and enjoyed the company of an old friend and customer. As was his custom, my guest ate quickly and left for home at nine. I finished my glass of port, paid the bill and started my short walk back to the Hyatt.

Half way to the hotel, I passed Howl at the Moon. I could hear the dueling pianos and loud singing and decide to stop for a drink.

I sat at the bar, ordered a Sam Adams and surveyed the crowd. I spotted Jackie and Donald almost immediately. They were sitting at a large round table in the middle of the bar. They were twelve people total, ten men and two women. Except for the second woman, they all seemed to be in there 50's and 60's.

Jackie was wearing a stunning black, knee length cocktail dress. The pearls around her neck highlighted a fair amount of cleavage. Her legs were crossed and her athletic legs looked great in nylons.

I positioned myself so I could watch the performers and watch Jackie's reflection through a mirror on the wall. I also watched the second woman at the table. She was in her late twenties, very attractive, tall and curvy. Her tits were huge and she seemed to enjoy showing them off.

Jackie and the second woman were having a ball. They talked, laughed and sang along with the crowd as the pianists played their sing-a-long. It took almost thirty minutes before Jackie spotted me. She tried to get my attention, but I ignored her wave. She leaned over whispered in her girlfriend's ear and nodded in my direction. They whispered back and forth. Jackie finally excused herself and approached my barstool. "I thought you didn't like crowds?" she said as she rested her hand on my shoulder.

"Hi Jackie. I was walking back to my hotel and heard the noise. I decided to stop for a beer."

We chatted for a few minutes and I tried to hold her stare. I smiled to myself as she occasionally peaked at my crotch. The outline of my monster was easy to see. "Please join our group, there's plenty of room."

I smiled and agreed. "I'd love to, thanks."

I walked behind her as we made our way across the bar. I think Jackie put a little extra wiggle into her perfect heart shaped butt. As we approached the table, she called out, "Donald, its Christopher from the plane this morning." For the first time, I noticed how drunk Donald and all the men were. Donald slurred a greeting and gave me a half wave. Jackie introduced me around the table, ending with Susan. I pulled up an empty chair for an adjoining table and sat between the two girls. It turned out that Susan was married to one of the old guys. Jackie teased that she was a trophy wife.

Over the next hour, the men ignored us and talked and drank. I had a ball talking with Jackie and Susan. As I was in the middle, I had to turn my head back and forth as they talked. I was amused, when I caught each woman staring at my cock every time I turned my head. There attention excited me further and before long, I was stretched to my full eleven inches. The women were practically drooling.

Shortly before eleven, the party started to break-up. As Susan and her husband, Jeff, said their goodbyes, she gave me an innocent hug and kiss on the cheek. I looked over her shoulder and could see no one was paying attention. I let my hand slip to the small of her back, pulled her crotch against mine and ground my cock into her cunt. As I stepped back, Susan groaned a disappointing, "oh God." I smiled, winked and wished her a good night. As Susan and Jeff left the bar, I again sat next to Jackie.

Jackie gave me a knowing smile, leaned in and whispered, "if you do that to me, I think I'd cum on the spot."

When it was our turn to leave, it was obvious that Donald was to drunk to get back to the hotel. As their Marriott was next to my Hyatt, I agreed to help Jackie get her husband to the room. The Marriott was less than half a mile away, but because of Donald's condition, we took a cab.

The bouncer helped me get him into the cab and the bellman assisted me in getting him out. It was a struggle, but we finally made it to their 27th floor suite. I walked him through the living room and into the bedroom. I let him fall into the bed. Poor Donald was asleep before he hit the mattress.

Jackie was standing at my side. She was shaking her head in disgust as she looked at her husband. She started to say something, but I reached out, put my arm around her waist and pulled her toward me. I pulled her face to mine. My tongue pushed past her lips and into her mouth. Jackie resisted for half a second and then gave up. Her tongue was soon in a mad fight with mine.

I reached down her back and over ass. I pulled up the back of her dress. Jackie was wearing thigh highs and a microscopic black thong. I roughly grabbed her ass cheeks and pulled her against my cock. Jackie buried her face in my neck and groaned a muffled "your dick feels so fucking good."

Jackie spread her legs as my fingers explored her asshole and cunt from behind. She was franticly rubbing her soaked gash into me. "Ready to suck some thirty year old dick, baby?" I teased.

"Yes...yes, anything. Take me to the living room."

I pulled my hands from Jackie's ass, put them on her shoulders and pushed her to her knees. "Sorry baby, right here, right now, in front of your passed-out husband." I grabbed a fist full of hair and pulled her face against my pant-covered cock. "Take it out baby. Suck me good and I'll take you to the other room and fuck you till you can't walk."

Jackie turned sideways and looked at her sleeping Donald and then back at me. She was a woman possessed. In a flash, my belt was undone, pants unbuttoned and falling to my ankles. Jackie hesitated for a second, than pulled my boxers down. My eleven-inch cock bobbed in front of her face.

Taking another hand full of hair, I ordered her to put her hands behind her back. She meekly complied. I stepped in closer and let my dick rub against her cheek and across her face. "Open your mouth, slut, I'm going to shove my young meat into your throat."

Jackie's mouth opened wide. My dick is obscenely thick. The head of my cock barely made it past her teeth. At three inches, her mouth was stuffed. "If you can't do better than that, I'm leaving, slut." Jackie looked up with pleading eyes. She reached behind me, grabbed my ass and pulled me deeper into her mouth. She barely got another inch in. She was gagging and choking and tears were running down her cheek. "What a pathetic blowjob, this is a waste." I pulled from her mouth.

"Please, I'll do anything. I want you to fuck me," Jackie begged.

I turned my back to the kneeling Jackie, and ordered, "Lick my asshole."

I heard her whimper, then felt her hands pull my cheeks apart. I became impatient, reached behind me and brought her face to my butt. "If you don't do this well, I'm leaving."

Jackie took a tentative first lick and than dove in. "That's it bitch, tongue fuck my asshole." I ground back into her face as her tongue inched past my sphincter. "That feels so fucking good." I let her lick and suck my hole for a few more minutes and then pulled away and turned to face her.

"Take off my shoes, socks and pants," I ordered the kneeling older woman. She crawled closer and undressed the lower half of my clothes. As she completed her work, I pulled off my shirt and stood naked in front of her. Then turned and walked from the bedroom and into the living room of the suite.

Just a few moments passed and Jackie followed me from the bedroom. She closed the door behind her and leaned against it.

"Strip," was all I said.

Jackie bit her bottom lip and reached for the hem of her dress. She pulled it over her head. Her bra quickly followed. Her C cups stood firm and were capped by cherry red, half-inch erect nipples. Her thong was already half off and it easily slid down her legs. "The nylons too?"

"Everything," was my answer.

I smiled at Jackie as she pulled them off. I laid on the carpet and offered, "you've done a good job baby, come on and get some cock."

Jackie approached me and squatted like a catcher over me. She grabbed hold, her finger barely surrounding my shaft. She rubbed my dick head over her sloppy cunt. "Your nice and wet, girl. That'll help. But go slow, you don't want to hurt yourself."

Jackie rubbed me around her clit, "feels so fucking good...oh god!" She shuttered through a small orgasm.

She lined me up with her hole and sank the first three inches into her pussy. "You stretch me so good," she said. This fifty-year-old woman was incredible. Over the next fifteen minutes, she worked all eleven inches of hard cock into her cunt. When she was finished, she was kneeling astride of me. "Let me get used to this." She laid her head against my chest.

I loved the feel of her breast as they pressed into me. My hands roamed over her back and played with her ass. I teased her asshole and slowly sunk my middle finger into her. "You make my ass feel so good." As she lay on top of me, I slowly fingered her tight hole. Jackie's breathing became deeper and more ragged, "yes...yes...Yes...OH...YYYEEESSSSSSS," she groaned as her whole body shook.

Once again, she laid against my chest, panting in post orgasmic bliss.

"Ready to get fucked?"

Jackie pushed herself off my chest and looked into my eyes. She simply nodded her head. I pulled her against my chest and rolled her over. I hooked my arms through her knees and doubled her over. I started slowly, fucking her with just a few inches. My cock fit her tight snatch to perfection. After a short while, I was pounding ten inches into her cunt. Jackie had one screaming cum after another. Ten minutes into our fuck, I felt my balls start to tighten. "Grab my balls, slut, make me cum."

Jackie reached under her ass and grabbed my swinging sack. As she massaged my balls, I bellowed and came deep in sloppy hole.

My cock softened a bit, but I kept fucking her. As I'm only thirty, I can easily stay hard through a second fuck. It took Jackie a moment to figure out what was going on, "don't you ever get soft?" she whimpered.

I continued to fuck her in the missionary position until I was fully hard. "On your hands and knees, bitch." I pulled out and watched as Jackie struggled into a doggie position. Her pussy gapped open and was a sloppy mess. I lined my dick up and easily slid into Jackie's used hole. I grabbed her hips and started pounding her from behind. "Play with your clit, baby." Jackie balanced herself on one hand and reached between her legs. She started cumming immediately as her fingers rubbed her nub.

After another long hard pounding, I felt my second cum approach. "Your going to drink my cum, slut. Turn around." An exhausted Jackie turned and kneeled in front of me. She wrapped two hands around my cock and slowly jerked me off. "Here it comes, drink it all."

Jackie lined the head of my cock up with her open mouth. One hand jerked me, while the second reach around to my ass. When her finger started to rub my asshole, I exploded. Jackie sucked my cock head and my entire load into her mouth.

I was done for the night, so I asked Jackie to get me my clothes from the bedroom. As she got to her feet, I reached out, pulled her against me and kissed her. I could taste my cum on her tongue. Jackie opened the bedroom door and picked my clothes from the floor. I laughed when I saw Donald hadn't moved. He was sprawled across the bed and was sleeping soundly.

I dressed quickly. It was time to go. Jackie, looked at me shyly and asked, "can we do this again, tomorrow night?"

"It depends," I answered.

"On what?"

"It depends if you can get Susan to join us." I scribbled my cell number on a piece of paper, kissed Jackie's cheek and left one hot MILF.