I received a text from my BFF Jeff, “Let’s go to the Kentucky Derby party Saturday at River City. I’ll see you at 5pm.”
When Jeff and I met at our favorite dive bar, The Ponderosa, a slightly western themed establishment, he already had a plan. “Tim, I hear this is a pussy-fest. Women love dressing up, wearing stupid hats, and drinking mint juleps. I’m sure we’ll both get laid.”
“Where is the party?” I said.
“The ritzy River City Bar and Grill,” he said.
I laughed, but listened to him tell me more about the event. He emphasized that we needed to be dressed up in a jacket, tie, all the GQ type of clothing we normally only wear to weddings or funerals. He went on his phone and bought our tickets, which were a whopping $100 each.
As the day approached, I started thinking about what to wear. The weather forecast predicted a beautiful spring day in May with temperatures in the low eighties. I decided to go with khaki dress slacks, a pastel windowpane design on a white button-down shirt, no tie, navy blazer, and a pink and purple pocket square. I topped it off with brown leather shoes and dress belt, and a light mocha brown fedora, which I purchased just for the event.
River City Bar and Grill had a large banquet room where they had several projection screens for the Kentucky Derby and seating for about 160 guests it looked like. There were three bars around the room and a buffet area at the front of the room. The restaurant’s large bar was also open to ticket holders.
In talking with co-workers and friends, I learned that this was a fantastic party for the upper-middle-class crowd, and there would be a lot of single/divorced women over forty. Jeff and I definitely fit this demographic. We were both forty-five, divorced, and dating sporadically. The event began at noon with an open buffet, and the horse race was set to start at 4:00 pm Pacific Time in Oak Valley. While the race only takes two minutes, it would be a marathon of a day.
Jeff and I decided to be casually late and arrived at 1:00 pm. As we checked in, we received our wristband for the buffet and three free drink tickets. We took single photos together at the photo station, complete with a Churchill Downs backdrop, jockey silks, saddles, and various other props.
When we entered the room, we noted that it was already about fifty to sixty percent full. We guess-timated that half the people were couples, and the rest were single women. It looked like we two of about ten single males.
“It will be like shooting fish in a barrel,” said Jeff, insinuating that we should have no problem hooking up with women.
We went to one of the bars to get drinks and then looked for a spot to sit down. We discussed the pros and cons of sitting at a table with a few women versus sitting at an empty table by ourselves and seeing who would sit next to us. We put our drinks down on an empty table, tilted the chairs indicating we were sitting there, and headed toward the buffet.
Upon returning to our table I noticed there were two flutes of champagne directly across for us. The tables were round tables for eight, so there were empty seats on both sides of us. We slowly began to eat our lunch and soon approached two women.
“Hi, we hope you don’t mind if we join you at this table, do you?” said a redhead woman.
“Not at all,” said Jeff. “Why don’t you two move over in case a group of four would like to sit at the table.”
“Oh, good thinking,” said the blonde.
We all introduced ourselves and gave a quick “elevator bio” with our jobs and such. The redhead was Cindy and the blonde Breann, or Bree. Both lived in Oak Valley and worked at the local bank.
“Tim’s grandfather was a VP at the bank when we were kids,” Jeff quickly interjected.
I gave Jeff the evil eye. He knows I don’t like having strangers know exactly who I am. I didn’t want to be judged by my family name or our families wealth.
Backstory: Tim’s mother’s family were early pioneer settlers in the Oak Valley area in 1848. Four brothers spawned a ton of children, and over the generations, there were a lot of Tim’s mother’s family in town. There was a park, school, street, and shopping center named after the family. His grandfather was a large wine grape grower and was an Executive Vice President of the local bank. Tim’s grandfather was considered very rich, thanks mainly due to his stock in the bank. Over the years, Tim’s parents inherited and bought bank stock, as did Tim.
“Oh, who was your grandfather?” asked Bree.
“Woody Beck,” I said, thinking they wouldn’t know who he was. “He passed away a long time ago.”
“I see his photo every day,” Bree said. “I work in the Executive Offices. I’m Kent’s assistant.”
Backstory: Kent was Kent Stein, the CEO. He was an “outsider” who was hired about twenty years prior. At one stockholders meeting, when he found out who Tim’s mother was, he spent the next twenty minutes sitting and talking with her about her father. The stockholders love the way Kent grew the bank, increased profits, dividends, and that the stock had doubled in price.
Jeff and I learned more about the two ladies. Bree was forty, originally from neighboring Twin Rivers, while the redhead, Cindy, was forty-one, and was born and raised in Oak Valley. She knew Jeff’s younger sister from their high school days.
**
After several hours Bree and I had coupled up, while Jeff and Cindy were taking it a bit slower. The four of us mingled with others for the next few hours while watching some of the preliminary horse races and tv packages about the owners, jockeys, and horses. There were racing themed games, vendors selling horse themed arts and crafts, and even riding lessons.
By race time we all had a good buzz going but certainly were not drunk. We cheered on our picks during the main race, and Jeff’s pick, Hazel’s Love, won the derby by almost two seconds.
As we sat at our table we discussed plans for the night. None of us were hungry, but all wanted to move on to another location to have a few drinks, and maybe dance. The problem was it was now only 5:00 pm, and nowhere in town would offer dancing until 9:00 pm.
“We could go back to my house, sober up a bit, and then go dancing,” I said.
The women looked at each other and whispered to one another. They excused themselves to use the powder room, but Jeff and I knew they were trying to decide if they’d go back to my place.
“Dude, Bree seems really into you. I bet you can get her naked,” Jeff said. “I don’t think Cindy will want to go; she’s not giving me much.”
I laughed, “Bro, it’s always the quiet ones who are the biggest freaks. Plus, she’s a ginger.”
**
Twenty minutes later the four were walking into my home. I led them to the kitchen and asked about drinks.
“Forget the drinks,” said Bree, pointing out the windows, “I want to see your backyard and pool.”
“Oh, you ladies are in for a treat. This is one of the nicest backyards in Oak Valley,” Jeff told them.
I took them outside, and, yes, I had a wonderful backyard. The large patio was covered and featured a built-in flat-top grill, a BBQ grill, and refrigerator, several kitchen counter appliances, a dining table for eight, and two love seats and four chairs around a gas firepit. The pool was spacious, featuring a tanning ledge, multiple lounges equipped with umbrellas, and an independent spa.
As we returned to the kitchen I suggested we play cards or a board game. Cindy asked, “Do you have Cards Against Humanity?”
I laughed, “I do. That should be a fun game for us.”
Jeff chimed in, “Especially if we have a few more drinks!”
He quickly went to my wine cabinet and selected a wine, opened it, and poured us all a glass while I found my cards. We sat around the kitchen island as I dealt out the cards.
As we started to play, I turned up the flirting with Bree, and put my hand on her lower thigh, giving it a slight squeeze. She looked at me and gave me a quick wink. She then spread her legs open a few inches. My hand moved higher, then slid back down. When I slid it back up, she placed her hand on mine.
I didn’t look at her, but said, “Ohhh.”
While we continued with the card game, I was having an impossible time concentrating.
I then felt her hand on my manhood, giving it a slight squeeze. I read her move as the green light to proceed, so my fingers zeroed in on her folds. I could tell she wore a lace panty of some type, as I rubbed her labia.
Bree turned in her seat, squeezed her legs together, trapping my hand, and said, “Tim, can you show me where the bathroom is, please?”
As we stood, I saw Jeff and Cindy roll their eyes, and Jeff gave me a thumbs up.
“Yes, it’s down the hall here,” I told Bree as I grabbed her hand.
I led her right past the bathroom to my bedroom, closed the door, and locked it. I pushed her up against the wall and kissed her passionately. Our tongues swirled, darted, and waltzed together. As we continued to kiss, we stumbled our way to the bed and lay side by side. My hands were caressing her tits while she had one rubbing my cock over my slacks.
I whispered, “I want you. May I undress you?”
Bree didn’t say a word but nodded and started to unzip my pants. After fumbling with my belt, she said, “Why don’t we undress ourselves.”
Once naked I could see that she had a wonderful body; she obviously kept in shape at the gym. Bree was average height, a size eight-ten, full D cup boobs, and sparkling blue eyes to go with her blonde hair. She was a knockout.
After kissing a few more times, I kissed down her neck and softly suckled on her left breast while my left hand groped her right tit. After a bit I switched. I placed one hand over her vagina and could feel the warmth, and when I slid a finger in her folds, I could feel the moist heat. As I explored her pink tunnel it was obvious that Bree was super wet. I pulled my finger out and sucked it clean.
“Do I taste good?” she whispered.
“You taste great. But I want more,” I replied, as I moved and positioned myself between her legs.
Bree was freshly waxed but had a small postage stamp size of hair above her clit. Her lady bits looked wonderful, and I couldn’t wait to bury my face in her pussy. As I moved my head closer, the musky aroma was intoxicating. I inhaled a second time to savor the moment.
“Not only do you taste great, but your aroma is such a turn on,” I whispered.
My tongue started low and licked up her labia majora, splitting her folds on its way down. Bree wiggled her ass a little, giving me affirmation that she enjoyed the first lick. I licked twice more before slowly inserting one finger.
“Ohh, yesss,” she moaned.
With my finger stimulating her inner walls my tongue returned to the top in search of her pleasure nub. I guided my tongue tip around Bree’s clit and gently licked it, causing her to twitch. My mouth covered the area and while gently sucking, my tongue flicked her growing clit.
“Yesss. Suck my clit, Tim,” she moaned.
I doubled down on her request and applied as much suction as I could to her clit, sucking and slurping on her pinkish-white pearl. It seemed like ten minutes, but it was only two, but her legs were soon starting to quiver.
“I’m going to cum. Don’t stop!” she said loudly.
Her legs were now shaking and her body followed suit. Bree’s breathing was labored with short loud breaths. I kept sucking her tic-tac and added tongue flicking. This pushed her over the edge.
“Yes! Yes!” Bree screamed. “I’m cumming!”
Her nectar was flowing like the Mississippi River, and I was enjoying the sweetness of her natural juices. I stopped my oral assault and was about to pull my finger out, but, for some reason, I started banging her cunt in rapid fire motion.
Bree was moaning as her body rode the orgasmic wave of pleasure when, out of nowhere, she began squirting. Three strong blasts of liquid soaked my right hand as I continued to ravage her pussy.
“Stop! Please, stop!” Bree yelled.
I instantly stopped and removed my finger. “Holy shit!” I mumbled.
“Oh, I’m so sorry. I’ve only done that once before,” she said sheepishly. “And your duvet is now soaked.”
I looked down at the comforter duvet, and it was soaked from the combination of her pussy juices and from her orgasmic squirting, but I didn’t care. I had just made this beautiful woman climax so hard that she squirted. I thought it was a badge of honor and a job well done.
“Don’t be silly, that was so very hot!” I told Bree. “I can wash the duvet; it’s no big deal.”
I moved next to her and began to snuggle her warm body and kissed her blonde hair.
“I hope you’re still planning on fucking me,” Bree whispered to me.
“Guaranteed,” I replied.
The End
