Cindy Lou Ch. 02

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The continuation of the story of a young man's 'first time'.
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Part 2 of the 2 part series

Updated 06/08/2023
Created 12/19/2016
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This is the continuation of a story that I recently posted based on something that happened fifty years ago. I recently went to my fiftieth High School Class Reunion, and this is my version of what happened that weekend:

*

In case you have forgotten, my name is Jonathan Stevens MacIntyre, and I still live on the outskirts of the largest city on the Illinois River. My parents and in-laws passed away a decade ago, and my Connie lost her long battle with heart disease three years ago, but my daughters and grandchildren make my life worth living. I keep busy doing chores for the several widows and divorcees in the neighborhood, so I do not lack companionship, and seldom have to cook for myself.

Last summer, shortly after I finished writing 'Cindy Lou', I received a letter in the mail inviting me to my high school graduating class' fiftieth reunion. Since my closest friends were still living nearby, I would often see them around town. And while I had maintained contact with most of my classmates I had, however, lost track of a number of people over the years. I wondered how many of my old friends would show up at the reunion, and I was particularly interested to see if the last fifty years had been kind to Cindy Lou.

My daughters had signed me up with Facebook when they came home for their mother's funeral, and I had connected with dozens of people I had not thought about in years. However, no matter how much I looked I could find no trace of Cindy anywhere. You see, she had left town after college, and no one had heard from her since.

The reunion was to be held on the weekend of homecoming in September. The letter listed several events for the weekend, and the list first thing on the list of activities was a casual get together at the local VFW after the school's Homecoming game on Friday night. I asked Katie, one of my divorced neighbor ladies to accompany me so I wouldn't be alone, and as soon as we walked in the door, we were surrounded by old friends. The first person I recognized was Marcia Baker, an old neighbor who ended up teaching Kindergarten at my old grade school. I picked her out immediately because, at 4' 10", she was only a few inches taller than my Connie.

I spent the next hour introducing Katie to my old friends. Strangely enough, she knew some of their spouses, and we had a great time. Suddenly, I looked up and there she was, looking like time had stood still. On the arm of a pretentiously dressed man who looked out of place in our small village, was Cindy Lou. She was wearing a powder blue sweater, white Capri pants, and white ballet flats. Around her neck was a single strand of opera length 8mm pearls, and on her left ring finger was a diamond that had to be well over a carat.

Her hair was a bit lighter than the strawberry blonde I remembered, and there were a few wrinkles, but she looked twenty years younger than the sixty-eight years old we both were. She recognized me immediately, despite the grey beard I had grown over the last two years, and greeted me with a huge hug, smashing her still firm boobs into my chest, telling me how glad she was to see me. I told her I felt the same way, but my erection that she ground her crotch into had already told her that. I introduced Katie as my 'friend', and the two ladies chatted while I went to the bar to get two more beers. When I got back they had walked away, and Katie said, "She looks great for an 'old broad'. Right now I'll bet you are thinking about her sucking your cock again, aren't you, sweetie?"

I almost choked on my beer, and nodded with a red face. Jack Horvath, who was standing next to me and overheard Katie, said, "Jon, she did you too, when did that happen?" "Band contest, April, senior year." I whispered. "Well, that brings the count to twenty-five. No wonder George dumped her ass as soon as he got home from Germany." Jack said, and seven of my friends gave me 'high five's' and we all started laughing. I asked Jack if he knew anything about her husband, and Fred Nelson chimed in, "He's and investment banker named Brent Fairfield, from somewhere in Chicagoland, five years younger than her, and loaded. I'm guessing he paid for all the work she had done."

Katie asked us, "I've only heard Jon's story, but was she some kind of oral slut in high school?" Everyone laughed, and Bob Schultz said, "Cindy always acted like an uptight bitch in public, but that was only a cover for her 'inner slut' that only came out in private. It was the worst kept secret in school. We didn't know Jon was a member of our club until tonight, congratulations, by the way." As Katie and I walked around the room, and I introduced her to more of my old friends, I could see the word was getting around, and when Cindy and her 'trophy husband' left the VFW, Lester Maddox grabbed me and dragged me to the bar where there were eighteen shots of Jack Daniels lined up in a row.

Lester told me to grab one of the shots, and I was joined by seventeen of my old classmates, each holding a shot. Then our class president, Mike Wallace, raised his shot glass and said, "Gentlemen, tonight we add another member to our little club, Jon MacIntyre. To Cindy the slut!" and we all downed our shots. After that, every member of our club told his version of 'The Oral Adventures of Cindy the Slut'. After each tale, there were cheers and pats on the back, and after everyone else was done, Mike looked at me and said, "OK, your turn Jon." I told an abbreviated version of my story, and it was as well received than all the others.

When I rejoined Katie a few minutes later she said, "That was really cool Jon. You guys are a lot of fun, and she really is a slut." Then she planted a passionate, toe curling kiss on me that left me dizzy, and whispered in my ear, "I'm glad she taught you how to eat pussy, because you really are a master. Take me home and fuck me, I'm horny!" We said our goodbyes, and drove back to my house, where Katie and I fucked each other to exhaustion.

The first thing I felt the next the morning was a wet mouth sucking on my manhood. When I opened my eyes, I saw Katie's wet, hairless vulva dripping on my face. I grabbed the cheeks of her beautiful ass, and dove, tongue first into her pussy, causing her to gasp and swallow my cock to the hilt. She backed off, catching her breath, and we brought each other to a mutual orgasm, several minutes later.

After sharing a shower, we ate breakfast at my kitchen snack bar, still nude, and discussed the day ahead of us. You see, Katie was one of Connie's friends originally. We only became good friends after she kicked her cheating husband out and filed for divorce about a month after my wife's funeral. It started with her making dinner for me, and we finally became 'fuck buddies' about a year later. We both dated other people casually, often having lunch the next day, and discussing our respective partner's 'performance'.

Katie told me that several of my old classmates had caught her eye, and asked if I minded if she went home with one and fucked his or her brains out. I told her to 'go for it', and she told me that I should 'go after' Cindy. She said that she would 'run interference' with Cindy's husband for me. I told her that wasn't necessary, and that I would leave whatever happened up to Karma. When we were done with breakfast, she grabbed my flaccid cock and said, "I need some more of this before I go home lover," and dragged me to the bedroom.

I was completely hard by the time we got there, and we started fucking like animals as soon as we hit the bed. I was on my back, and she was riding me like she was breaking a wild mustang. It was an intense, although somewhat short session, which ended with both of us coming together. Afterward I was exhausted, but she was unusually energized, jumping off and running into the bathroom. She came back shortly, kissing me on the lips and cock and said, "See you later lover." and left my house in a rush.

Later that day I was standing in front of the full length mirror in the bedroom, making sure my tie was straight, when the doorbell rang. When I opened the door, Katie was standing there wearing a dress that was stunning and sexy, while being tasteful. She breezed into the house and did a pirouette saying, "How do I look?" I had to pick my jaw up off of the floor before answering, "Wow!" After I calmed down I put on my suit coat, and led her to my Explorer and drove us the five miles to the country club where the reunion dinner dance was held.

When we walked into the ballroom at the club, we were greeted by Becky Cospito, the Vice President of our senior class. She gave us our name badges and I signed the registry. The first hour was spent mingling with classmates and former teachers. Where there were about fifty people at the VFW the night before dressed casually, tonight it appeared that there were nearly one hundred fifty in attendance. The ladies wore dresses, and the men wore suits, and the ambience was subdued festive.

Everyone chose their own seats, and the old cliques sat together, as always. Dinner was a buffet, and it was excellent. Afterwards, there were the obligatory speeches by the class officers and former teachers, and then the tables were cleared as a small band began to play 60's and 70's music. Katie and I danced with each other for the first two songs, and then she whispered in my ear that she saw Cindy's husband on his phone. I turned around to see him leaving alone and her sitting alone at their table.

Katie whispered to me, "Go for it Jon, I think I'm going to get lucky tonight." as she motioned to three of my classmates who were looking lustfully at me." I whispered back, "If I remember correctly, Mark and Kent used to be hung, but Gary used to have a tiny cock." We both laughed and she headed over to the bar where the three guys she was interested in were standing.

I walked over to where Cindy was sitting alone at the table with a sad look on her face. I sat next to her and we talked about our lives and children. When the band played a slow song, I asked her to dance, and she accepted. After three more songs, I walked her back to her table, and asked her if she wanted a drink, and she said that she would like a martini. I returned to the table with her drink and a scotch for me, and we talked more about trivial things.

After three more drinks and six more dances, Cindy was noticeably inebriated, so I asked her husband Brent. She slurred, "He said he had an emergency call from his office, and they were sending a car for him to 'put out a fire' in Bloomington. I know that was probably a lie. He's probably shacked up with his secretary at her parent's house. The part about Bloomington was true though. Her parents do live there, and they are on a Caribbean cruise." I asked her if she wanted to go home with me, and she agreed, as long as she drove. She had to return the rental to the airport in the morning, and I agreed.

I told her to wait a minute, and walked over to where four of my classmates were surrounding Katie. I handed her the keys to my Explorer, and told her that I would see her sometime tomorrow. She gave me a big hug and thumbs up, and we parted company. I went back to Cindy's table and held out my arm for her to grab, and we walked, arm in arm to her rental, a big black Lexus. She drove us to her hotel, and as soon as the door was closed, she wrapped her arms around me and gave me a passionate kiss.

Next we had a race to see how quickly we could get out of our clothes. It was a tie, and we kissed and groped our way to the bed where I kissed and caressed her firm boobs. I paid particular attention to her nipples and aerolas. It looked like time had been very kind to her body, and if there had been any work done, I did not see any scars. I kissed my way down her body, and nibbled my way around her smooth hairless, now dripping vulva.

When I spread her labia open, and drove my tongue into her vagina, she started to scream and shake as her first orgasm overtook her. I kept after her, adding two fingers in her vagina, and one in her ass, and held her in a constant state of orgasmic bliss, as I sucked and nibbled on her clitoris. Finally, I let her down, and watched her squirm semiconscious until her eyes started to open. I then drove my rock hard manhood into her in one slow powerful stroke. Her eyes rolled back in his head, and I started gently stroking in and out of her until she opened her eyes and said, "Fuck me like an animal Jon!" I complied, and we fucked like teenagers until I came, after giving her two orgasms of her own.

Later, lying in each other's arms, Cindy said, "Wow Jon, you used to be an amazing pussy eater, but now you really are a fucking machine. Brent is ten years younger than you, but he has never made me feel the way you just did. I really regret not letting you fuck me that day in the car." I smiled at her and said, "I was a virgin then, Cindy. I probably would not have lasted very long, so it was probably best that we didn't do it then." She grabbed my half hard cock and said, "Well I definitely want more of this, and my plane doesn't leave until Noon tomorrow so," climbing on top of me in the sixty-nine position, and swallowed my cock to the hilt.

Not one to be outdone, I assaulted her labia and clitoris with my tongue and fingers, and as soon as she had me fully hard, she turned around and impaled herself on my fully erect cock. She rode me like a madwoman, and I mauled her beautiful boobies. After she came two more times, I joined her third orgasm with my second. She then collapsed on top of me, and fell asleep. I reached over and turned off the lamp on the bedside table and joined her in slumber soon after.

When I awoke, my morning wood was still buried in Cindy's vagina, and soon after she started fucking my cock before she totally woke up. When she opened her eyes and saw my face, she smiled and started riding me wildly, saying, "Yea Brent, take that you stupid cheating bastard. I'm fuckin a real man now, instead of that tiny little dick of yours!" She had two orgasms before I came and my filling her cunt with my cum sent her over the edge and gave her a third. She came down kissing and trying to shove her tongue down my throat. Finally, she jumped off of me and ran for the bathroom, holding her crotch to keep our combined juices from leaking onto the carpet. I got up and casually walked into the bathroom where Cindy was sitting on the toilet peeing. I walked over and stood in front of her and said, "Scoot back, I need to piss too."

She complied and I pointed my half-hard cock into the space between her pussy and the front of the bowl, and let loose with a powerful stream. When I finished, Cindy grabbed my cock and sucked it clean. I looked her straight in the eyes and said, "So My cock is bigger than fancy boy Brent's."

She responded immediately, "Yes Jon dear, by a long shot. I married him because his parents had money, but he barely fills me. He has a real inferiority complex about it, so I guess that's why he cheats. He is constantly looking for a younger, tighter pussy to make him feel like a man."

I pulled back the shower curtain and turned on the water, adjusting the temperature. I stepped into the tub and helped her get in with me. I grabbed the small bottles of body wash and shampoo, switched on the shower and held Cindy in my arms started to wash her gently, touching every inch of her beautiful body. After I washed and rinsed her completely, she did the same to me, spending a lot of time on my cock, until it was completely hard. When she turned around and bent over, grabbing her knees, I knew what to do next. I slid my cock into her eager cunt and fucked her till she came again.

The water was getting cooler, so I rinsed us both off, and grabbed the towels to dry us off. As she dried her hair, I called room service and ordered breakfast. Being a typical woman, the food arrived before she finished in the bathroom, and we ate breakfast on the rumpled bed in the nude. When she finished she asked, "have you got one more fuck in you tiger?" When I nodded, she said, "Good, I want you to fuck my ass!" and got on all fours with her ass in the air. I don't know how, but my cock rose to the occasion, and I got behind her and slid into recently well fucked pussy. When she complained, I said, "Don't worry, I'm just getting it lubed up." As soon as I had him properly lubricated, I pulled it out and drove it slowly, but firmly into her rosebud until I was buried completely in her bowels.

She let out a long sigh saying, "Yesssssss, now fuck me till I can't walk lover!" I did exactly that, and she had another orgasm before I filled her colon, and causing her to have another orgasm, and collapse under me. When I started to pull out of her, she stopped me, saying "Wait." She reached under the pillow and produced a jeweled butt plug, and told me to push it in as soon as I pulled out. I did as she asked, and then she said, "I want to keep your seed in me all day. I plan on telling Brent everything we did, and I am going to make him eat your cum out of my ass when we get home. I want him to see what a satisfied, well fucked woman looks like!"

We both got dressed, I carried their bags downstairs and loaded them in their rented Lexus, while she checked out of the room. She drove us to the Airport, and we checked in the rental car and then the bags through to Ohare. Then we sat waiting for her husband and his bimbo.

Brent and Jeannie showed up about a half hour later, and Cindy embraced her husband and kissed him on the cheek. I was introduced to Jeannie, and shook Brent's hand, telling him, "I was happy to be able to take care of Cindy for you. We had a good time catching up last night." He had a strange look on his face, but smiled politely.

Brent and Cindy walked through security with their carryon bags, and Jeannie asked me if I needed a ride home. I told her I did, and we walked to a bright red Miata convertible. As we drove to my house, the skinny little twenty-something blonde remarked, "Brent really likes fucking me because my pussy is so much tighter than his wife's old worn out cunt."

Hearing that I remarked, "He must have a really small cock, because she has one of the tightest pussies I've ever fucked. Hell, she's at tight now as she was when we used to fuck in high school, fifty years ago." Her eyes got big and she slammed on the brakes pulling over to the side of the road. She looked at me and said, "Don't fuck with me, old man!" "OK," I said, and undid my pants, pulling them and my boxers down to my knees. She stared open mouthed at my half hard cock, still red from fucking Cindy last night and this morning. She reached over and grabbed ahold of it, her fingers not touching because of its girth, and said, Holly Fuck, can I have some of that?"

"Do you think you can handle it, little girl?" I said in my best 'pervy' voice. "I don't know mister, but I sure want to try." She said in a 'little girl' voice, and put her car in gear, spinning her wheels and spewing gravel all over the road, as I pulled up my pants. When we got to my house, I retrieved my extra house key from its hiding place under a rock by the door, and we went directly into the master bedroom.

We both undressed in record time, and standing in front of me was a beautiful young blonde about 5' tall, with firm grapefruit sized boobs topped with tiny erect nipples, a slender waist, above a nice round bubble butt and hips and shapely legs. Her vulva was a tiny 'innie' that was not shaved, but covered with soft looking blonde fuzz. My cock rose to 'attention', and she said "Holly Fuck, you're huge!" after she fell backwards onto my bed and spread her legs wide open like she was doing the splits.

I crawled between her legs and started 'eating lunch', and she responded by wrapping her legs around my head and moaning, "Ohhh... Gooood." I stuck two fingers in her vagina, and one in her ass as I sucked on her tiny 'pearl', and brought her to a screaming, squirting orgasm. When she relaxed her grip on my head, I lined my cock up with her dripping wet pussy, and drove slowly into the tightest snatch I had been in since my wedding night, until I had impaled her to the hilt. She responded by having another orgasm, screaming unintelligible gibberish.

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