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Commander Meets The Socialite

"Helping those who help others"

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1.8k Views 1.8k
1.0k words 1.0k words

Author's Notes

"It’s a first time story, so I figured recalling the truth would be easier than dabbling with fiction."

Kara was a community do-gooder. A forty-five-year-old divorced single mom of two teenage girls. She ran her own business and volunteered for a non-profit that supported social service programs in the community. She was short, busty, pretty, and spicy in her personality.

I was a local precinct commander for the police department. At forty-seven, I still had my college baseball playing build from my daily workout regimen.

Over a two-year period, Kara and I attended several community meetings as stakeholders for our perspective entities. Eventually, we were selected to be on a committee together. During that time, we got to know one another in a more personal nature.

Kara expressed a desire to learn to play chess. Her daughter was a member of the school chess club. Kara did not know how to play, but wanted to learn so she could spend quality time with her daughter. I told her I would be happy to teach her and we scheduled a date to meet at a local park. I brought an old plastic chess set which had a cardboard chessboard. It was the set I used to teach my boys to play.

We sat across from one another at a picnic table. The chess lessons were long and tedious. Kara had no clue how to play, nor did she know the difference between any of the pieces. After about an hour, a storm came in and so we gathered up the pieces and ran to her car which was the closer of the two in the parking lot.

We sat in the car for about five to ten minutes, making idle chit-chat. The rain was pelting on the car and you could barely see out the window. Kara put her hand on top of mine and told me that with her busy life as a single mom, businesswoman, and volunteer socialite that she has had no time for any fun and thanked me for trying to help her learn chess.

I took my hand away from her hand and lightly grazed her cheek. I leaned over and kissed her. We broke our kiss and looked into each other's eyes and kissed again. This time I licked her lips until they parted and our tongues began to explore our mouths. After a few minutes of kissing, we decided the center console was an impedance and so we scampered to the back seat.

We continued to make out like horny teenagers. I felt her up through her top. Kara began moaning into my mouth and so I moved my hand inside her top and freed her tits from her bra. Her nipples her hard and long from arousal.

Kara was breathing heavily as I kissed her neck and sucked her nipples while my hand worked its way inside her pants. Kara was oozing with wetness. I fingered her deeply with one, two, and then three fingers. While she was cumming she nearly sucked my tongue out of my mouth.

I pulled my fingers from her pussy and painted a mustache with her juices above her lips. I licked the mustache off and offered my pussy-soaked fingers to her open mouth. Kara licked and sucked them clean.

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I whispered in her ear that she was the queen and she could have my bishop now if she wanted to play some more. With that, she undid my belt and I slipped my pants down, which freed the bishop for the queen to take. And take it, she did. It turned out that Kara loved sucking dick. She licked, she kissed, she sucked, and she throated my cock.

While Kara was sucking my cock, I noticed the rain had stopped and I could see two college-age guys standing outside the window looking in. I pulled Kara’s head up from my cock and kissed her and then whispered in her ear, “We are being watched. There are two guys looking in behind you. I have no idea how long they have been there. Do you want to go or give them a show?”

Kara’s response was immediate. She smiled and said, “The show must go on.”

With that, she slipped her pants down, exposing her ass and pussy to them. She slid back down and continued to suck my dick and lick my balls. I could feel myself ready to release. I guided my dick back into Kara’s warm, wet mouth. And release I did. My cum filled her mouth as she gulped it down. What she couldn’t swallow, she licked off her lips.

The boys tapped on the window, gave a thumbs up and walked away. Kara smiled and said checkmate. And I reminded her she only took the bishop; the king is still in play.

Kara told me that she couldn’t believe how much more aroused she had become knowing we were being watched. She kissed me deeply and took my hand back to her soaking wet pussy. I then took my hand and guided her fingers into her pussy with mine. Together we slowly fingered her pussy and rubbed her clit. After a few minutes, she was gasping for air and bucking her hips.

Once Kara’s orgasm subsided, I pulled our fingers from her pussy and started to inch my middle finger toward her anus. As I started to circle her anus, Kara let out a whimper and rammed her tongue deep into my throat. My response was immediate. I pushed one, then two fingers into her ass. As I fingered her ass, I pushed my thumb into her pussy. It wasn’t long and Kara was screaming that she was cumming.

Listening to all of Kara’s orgasms had rekindled the flame in my cock. Kara went back to work on my dick with her succulent MILF mouth. Before long, I blew another load into her mouth. Kara kept my dick in her mouth until I was flaccid.

We decided we both needed to do this more regularly, so we set a date for a follow-up match. The arrangements were made and the story to follow…

Published 
Written by Lefty63
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