tagErotic CouplingsChicago, My Kind of Town

Chicago, My Kind of Town


Cold, windy and snowy. That describes winter in Chicago, IL to a tee. I had just finished a conference "How to develop a Compensation Plan." Sitting at the bar in O'Hare International Airport (ORD), waiting to board my plane for a 4-hour flight home. The cab ride to the airport was late because of the Heavy snow falling. As we were stuck in traffic, I turned my cell on phone and called the Airport Hilton. The way the snow was coming down, I had a bad feeling that flight were going to be cancelled.

Sipping on my Absolut and Cranberry, I watched the winter wonderland continue to pound the airport. Planes were slowly inching their way to the runway, which was stacked up like a can of Sardines. I turned to look at the flight status screen just outside the door, and it still showed my flight on time. Winter is short and darkness was fast approaching.

The guy sitting next to me paid his tab and headed into the waiting area. They just paged final boarding for his flight. I ordered another when I heard this voice say, "Is this seat taken?." I turned and told her, "No ma'am, it's all yours!!" I turned back to watch the planes trying to maneuver around the snow, when my new bar mate said, "excuse me, is that a Cap Cod your drinking?" A Cap Cod I thought briefly, I haven't heard the name in years. I told her, "I believe it is. I just call it an Absolut and Cranberry, but I think your terminology is right." She told the bartender, I have one of those. "Single or Double Ma'am?" She said, "you better make it a double, I think it's going to be a long night."

"Flight late," I said. "Of course! Aren't they always late out of O'Hare," she sighed. I thought about that, and she was right. When was the last time a flight was on time? I took another swig, and continued watching the planes slowly depart. I gazed at the status screen again, and this time what my bar mate had said, was a reality for me as well. Originally, my flight to Portland, Or (PDX) was supposed to leave at 5:00pm, and now it said scheduled departure, 6:30pm.

"SHIT!!" My bar mate said, "Join the crowd. How late is your flight?" I muttered, "an hour and a half." She said, "your lucky, mine was scheduled to leave at 5:00pm and it's not going to leave until 8:00pm."

"With flight time, that should put me home by 1:00am." She took another drink, and I just shook my head. "Well, I guess the good thing is tomorrow is Christmas Eve, and no work." She shook her head in agreement. "By the way, my name is Brian." I extended my hand to her, and she looked at me, extended her hand and said, "I'm Heather, nice to meet you."

We started the normal bullshit conversation, where do you live, what do you do for a living, do you have children, etc. We were talking so much that I had forgotten about the time. I looked at my watch and it was nearly 6:00pm. I had heard no announcements on my flight. I glanced over at the status board, and noticed my flight was not listed. I thought to myself, what the hells going on. Heather noticed I was puzzled. "Flight delayed again," she said to me. "I don't know I said, it's not listed on the board any more." She looked at me, and I could tell it wasn't good. "Are you sure," she said. "Yes, I'm positive. I can't see it listed." She shook her head and said, "Brian, you flight has been cancelled. O'Hare started doing that a month ago. When flights are cancelled, they just take them off the board."

"NO SHIT!!" I said.

At that point, the bartender said, "can I pour you another sir."? I said, "YES, and you better make it a double." I excused myself to check out whether Heather was right. She was. I made it to the ticket counter and the agent told me because of the weather (dah!!) The flight I was supposed to be on originates on the east coast and it was cancelled. She booked me on the first flight out tomorrow. I headed back to the bar. Heather was still there. "Let me guess. The weather." I said, "the usual, the flight I was supposed to be on couldn't get hear because of the weather, and there are no other planes available."

"Fortunately, I had this bad feeling in the cab on the way to the airport this afternoon, and I made a reservation at the Hilton."

"So, I'm going to sit here and enjoy my drink, while everyone else scrambles to find a room."

Heather said, "Where was that fight coming from anyway, New York?"

"How did you know, I said." Heather looked puzzled this time, and said, "I didn't. I was just being a smart ass." I told her what the agent said, and she quickly turned to the status board. She turned back, shaking her head. "Bartender, give me another double, it looks like I'm screwed." I said, "no flight to New York tonight, eh" She excused herself, and headed in the waiting area. I took this time to call my wife and let her know the status. She was upset of course. When Heather returned, She pounded her drink and said she needed to hustle over to the Hilton. The agent had told her very few rooms remained. She shook my hand and off she went. I took a quick glance at her ass, as she was leaving, not bad for a 45-year-old woman who has three kids.

I finished my drink, took one more final look at the planes struggling to make it to the runway, and thought, it's good I'm not flying tonight. As I entered the Hilton lobby, the line of people was staggering. Fortunately, there was a window for those with reservations. I walked right up, checked in and headed to my room. It was about 7:00pm, so I decided to take a quick shower, and head down for some dinner. Getting off the elevator, I noticed my bar mate Heather sitting on a couch by the door. I went over to her and said, "no luck getting a room tonight?" She looked at me and I could tell the doubles had taken effect. She shook her head, and said, "no rooms. I'm waiting for a cab to take me back into the city."

"The downtown Hilton has rooms." I asked her if she had time to get some dinner before the cab arrives. Right then an announcement was made to all waiting for cabs that the heavy snow has made it difficult to get around and it could be up to two hours before any cabs make it out here.

Heather dropped her head into her hands and just started shaking it from side to side. It was Christmas, and I was feeling no pain from the Absolut and Cranberry's. "Heather, at the risk of sounding like a pervert, the room they gave me has two queen beds, could I offer one to you?" She kept shaking her head in her hands, saying, "No, No, No.. I couldn't do that"

"Come on, tomorrow is Christmas Eve, and It's a season of giving. Besides, by the time you get to your hotel downtown, it will be time to take a cab back to the airport to board your flight." She looked up at me. I took my key out of my pocket, and handed it to her. "Go up to the room, take a nice hot shower and meet me back down here for dinner."

"Since my company is paying for the room, yours can buy us dinner. DEAL??" She extended her hand to grab the key, all the while saying. "A hot shower sounds great," I told her I would meet her in the bar.

About thirty minutes had past, I was nursing another drink when I saw Heather at the entrance. WOW, she looked fantastic. She was wearing a pair of black stretch pants, and tight red sweater that accented her, shapely breasts. Those business suits are for the birds. They ruin a woman's body. I waved her over and commented as she reached the table, "you clean up pretty good!!" She ignored my comment, but I could tell she liked my eyes checking her out. Marriage and kids sometimes stale a physical relationship. She came over to me, kissed me on the cheek and said, "Thanks for being so kind. The hot shower felt great." Right then, the waitress asked if she could bring Heather a drink, she said, "I'll have one of those," pointing to mine. "You might as well bring me another," I piped in.

A couple hours of more drinks, dinner and conversation past and we both decided we had enough. She picked up the check and we headed to the room. On our way out of the bar, I noticed it was still snowing. It looked like a foot had fallen. I grabbed her hand, and proceeded outside. "We don't get a lot of snow in Portland, and I was thinking about making a snowman."

"Besides, the cool air will do us good." We raced out the door and immediately started making the snowman. I was rolling up the head, when I felt a snowball hit me in the ass. "Oh, you'll pay for that I said." I grabbed Heather and started to wrestle with her in the snow. Her sweater was hiked up a bit, so I decided to put some cold snow on her belly. As I did so, she slumped down and my hands went right up the front of her sweater and were now on her naked breasts. My first thought, boy those are firm. Then I came to my senses, pulled my hands away and said, "Heather, I'm sorry I didn't mean to do that." She said, "No big deal. Not bad for 45 year old broad, eh?"

"Not at all," I said. "They're so firm, I didn't even know you didn't have a bra on. My cock was rock hard now. Rolling around in the snow and touching those breasts did the trick. She was now laying on top or me, and said, "talk about firm." She could feel my hard cock pressing against her thigh. She reached down, put her cold hand into my sweatpants, grabbed my hard cock and said, "fair is fair.."

I couldn't help it; I just planted a big kiss on her. She responded with kissing me back. At that point the snow had stopped, and we were both wet. She broke the kiss and said, "lets go get out of these wet clothes." Not only being wet, we were both cold. We raced back to the room, stripped out of our clothes and head for the shower. We stood under the hot water, holding each other as our frigid bodies warmed up. Heather was the first to speak, "will you fuck me in the shower, my pussy has been wet ever since you made that comment of how good I clean up. I loved the way your eyes were undressing me." I broke our embrace, turned her around, and guide my hard cock into her. "Oh god that feels fantastic," Heather, moaned. She was right she was well lubricated. It was like a hot knife going through butter. I reached around and grabbed her tits. "Pinch my nipples," she demanded. "OH Yeah, that's it fuck me, squeeze my nipples, fuck me, fuck me." I couldn't hold out, "I'm going to SPURT," I screamed. I pumped load after load into her. "I can feel you cum in me. I'm so close. Fuck me faster.." My hands were on her hips, holding them as I was thrusting into her. She now started to pull at her nipples almost to the point where it looked like she was going to pull them off. I was still somewhat hard and began to feel her pussy contract. She didn't have to say it, but screamed, "OH YEAH, OH YEAH, FUCK ME, I'M CUMMMMMINNNGGG….."

She pushed her has into me so hard I fell back onto the seat that's apart of the shower. My cock popped out of her and you could hear it. Cum started running down the inside of her leg. Most of it was mine, but she held her own.. She collapsed to her knees, and the water was still cascading down on her. She was barley audible, but I did make out, "it's been a while since I've had an orgasm that powerful."

"Thank you!!" I told her I didn't think it was all me.

We dried off, put on the robes hanging in the bathroom, and collapsed on the bed. "Since we properly introduced ourselves, can I ask you a question, Heather"

"Sure," She said. "How often do you masturbate?" Heather said, "Not as much as I used to. Maybe once every couple weeks."

"Have you ever massaged you G-Spot." I could tell she was puzzled. "I've heard of the G-Spot, but I'm not sure if I've ever stimulated it or my husband has either." I went to my overnight duffle bag, and grabbed out a very thin vibrator, specifically for the G-Spot. I brought it over to Heather and showed it to her. "What, you carry one around, just in case you find a slut like me?" I responded, "NO!! This is for my wife. I bought it downtown."

"I just thought if you were up to it, you could give it a try." She sat, grabbed it out of my hand. She was diligently checking its girth. I could tell she was wondering how it was going to work. "Would you like some help," I offered. She gave that, "yeah, thanks" look.

I turned it on, and told her to lay back. I untied her robe and let it fall to both sides of her. Her naked body was exposed to me. Her tits were firm. I would say about 34C's and a jet-black bush, perfectly trimmed. Her pussy lips were full and her clit stuck out, just enough to see it beneath the black hair. Her lips were still wet from the shower scene. I turned on the vibrator. Her eyes were closed, but I could tell she heard it buzzing. I started circling her nipples. She immediately got figgity and began a low moan. Her nipples were definitely sensitive. She grabbed the vibrator and started doing the same thing I was doing. I took the opportunity and ran my tongue up her wet slit. The second my tongue hit her dripping pussy, she let out a loud moan, opened her eyes, looked down at me and said, "are you going to lick me?" I gave her clit a couple of soft kisses, looked up at her and said, "Would you like me to??"

"OH god yes!! My husband stop doing that many years ago, and I forgot how good that feels."

I didn't answer her, I just began my assault. I licked each labia, up and down slowly. When I got to her clit, I slowly started making circles around it without touching it. She was still buzzing her nipples. She was alternating buzzing one and squeezing one. She was becoming very aroused. Her moans were more audible. After circling and teasing her, I took the tip of my tongue and started to lightly flick the exposed head of her clit. This sent her into another world. Her hips began bucking. I could tell she was near another orgasm. I stopped flicking it to tease her some more, when she stopped her moaning just enough to stay, "Don't stop baby, I'm so close to exploding. PLEASE DON'T STOP.." I wanted to tease her more, but, hey, it's Christmas.. I touched her clit with my tongue again, and she started bucking again. I flicked it faster and faster. She was moaning louder and louder. I had to hold her hips downs she was bucking so hard. She raised her head up to look at me flicking her, and that did it. She was over the edge. She started yelling, "I'M GOING TO FUCKING CUM RIGHT NOOWWWWW!!!!"

She was holding my head to her clit. I could feel the vibrator on my head. I quickly grabbed it, while it was still buzzing and slammed it into her wet hole. There was no resistance. The G-Spot vibrator has the right size and length for its purpose. I could tell it founds its way to her G-Spot. She took her hands off my head and started grabbing for the bed. All she could say, "What the fuck are you doing to me??! What the fuck are you doing to me???" I was still licking her clit and I could feel the vibrator buzzing inside her on my tongue. What a rush!!!

"WATCHOUT!!!!" She screamed. "That vibrator is making me pee."

"I can't stop it, I'm going to pee all over your face." Of course, I knew it wasn't pee. If the G-Spot is massaged just right, most women can cum just like men. It's clear liquid and it tastes great… Her breathing became labored. "OH GOD!! He..re.. He.. re.. it comes. I'm going to pee." With that her whole body started shaking. I removed my tongue just in time to get a nice squirt of cum on my face. It wasn't a lot. Just enough to wet my beard. It took her five minutes to stop from convulsing.

She kept saying, "I'm so sorry, "I'm so sorry."

"I've never felt that before, but I just couldn't stop it." Listen to me, I said. "You didn't' pee. You came. It was actually cum!!" She looked puzzled. "Here taste," I said. I took a finger and rub some off my face and stuck into her mouth. "That's what came out of me??" I explained to her about the G-Spot. She finally mustered enough strength to sit up. She hugged me for what seemed like 20 minutes. All the time saying, "thank you! Thank you!" I responded, "my pleasure!"

"Lets just say it was my Christmas present to you."

With that we fell asleep in each other arms. Luckily, we set the alarm clock. It went off at 6:00am. Heather scurried out of bed to hit the shower. I dozed off again, thinking about last night. I was dreaming of her hot pussy. I could feel the warmth. I suddenly woke up. Heather had her mouth around my now hard cock. I wasn't dreaming. No wonder it felt so real. She was expertly sucking my cock and massaging my balls. I think my balls were still full from the G-Spot encounter, because I never got a chance to relieve them. It wasn't going to take long and we both new it. "Oh god Heather, that feels so damn good." I looked up and she winked at me. I was right there. I could hear myself saying, "Yeah, Yeah." I looked up at her one last time. "I'm at the point of no return, if you don't want me to come in your mo…."

"AURRGHHHH" I pumped two or three loads into her mouth. She gently continued sucking me until my orgasm subsided. She removed her mouth from my now flaccid cock. She squeezed it a couple of times and licked the remaining cum of the tip of my cock with her tongue.

All I could say was, "that was awesome!!"

"What a way to be wake up." She moved up, kissed me on the lips couple times, and said, "Merry Christmas." I thanked her, and noticed the G-Spot vibrator on the nightstand. I grabbed it, jumped out of bed and met Heather at the doors as she was leaving. "Here, take this with you. It has your "NAME" written all over it." She kissed me and headed out the door.

To this day, I always sit at the same spot in the same bar at O'Hare International (ORD), hoping I might see Heather again...

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