Cindy Lou

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A story about a young man's first experience with sex
2.9k words
4.24
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Part 1 of the 2 part series

Updated 06/08/2023
Created 12/19/2016
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jsmangis
jsmangis
432 Followers

The following is a story based on people and places that I am very familiar with. All of the names and places have been changed to protect those who were involved in what happened so many years ago except for the title character:

Cindy Lou

As I reach the autumn of my life and am mourning the loss of the love of my life and bride of nearly half a century, I have been thinking back to my "first time". My name is Jonathan Stevens MacIntyre, but I prefer Jon, even though the little old ladies in town still call me "Little Jonnie" (it still drives me nuts). I grew up in a little village in the outskirts of the largest city on the Illinois River. My father was a businessman, my mother was a homemaker, and I was their pride and joy (the only child). It was in the late spring during the second half of my senior year in high school that the following happened. Since my birthday was in the fall, I was only eighteen and one of the youngest kids in my graduating class. I was a band nerd and painfully shy so I hadn't been bold enough to even ask a girl out, let alone date. By this time I was tall and slender (6' 1", 140lbs) and not a great physical specimen, although I was fairly well endowed (I only say this because compared to the other guys in gym class I fell somewhere above average).

Our school's varsity band didn't make the state finals, but our brass wind ensemble did, so we had to provide our own transportation to the state college in a neighboring town where the competition was to be held, but since the contest was on a Friday, we were given the day off from school. Our group was made up of myself on the French horn, Alvin on trombone, my best friend Jack on tuba and Cindy Lou and Bill on trumpets. Bill and Alvin rode together, Jack and I rode together, and Cindy Lou drove the brand new car that her dad had given her for a combination 18th birthday and early graduation gift.

We all arrived early and prepared for our performance, tuning up and running through several of the phrases and making sure we were ready. We were all very sure of ourselves because we had blown away all of the local talent in the regionals, so we were not nervous at all. That was until we heard who our competition was, a group from a small school in Wilmett and another from a big magnet school from Champaign-Urbana. We listened nervously to the suburban Chicago school that went first, and were relieved because the long trip really had an effect on their performance. They were awful! Next came the kids from the U of I sponsored school, and they were good, but we knew we were better. When it came for our turn we were perfect, and there was no doubt that we had won. All that remained was for the judges to post their results.

As I was waiting for the answer, my buddy Jack came up to me and said "Hey Jon, can you get a ride home, I just ran into an old girlfriend and I think I'm going to get lucky." I told him that it was no problem, and just then they posted that in fact we had won. I went looking for Alvin and Bill and they were nowhere to be found. Just then I found Cindy Lou. I asked her if she would give me a ride home, and she said "Sure I'd love to".

We picked up our horns and walked out to the parking lot and put them into the trunk of her "Baby", a brand new 1964 white Ford Fairlaine 500 with red vinyl bucket seats. We both got in and headed for home. The car was beautiful but didn't have air conditioning so, as it was a warm spring day we had the windows down.

Perhaps I should take this opportunity to describe Cindy Lou and how she was dressed. Because we were not performing with the whole band, we were not allowed to wear our uniforms. We were wearing white dress shirts and black slacks with black shoes and socks (a white blouse and black skirt with black flats in Cindy Lou's case). Cindy was beautiful and she knew it. As the only girl in the family (she had four older brothers), her rich daddy spoiled her rotten. At 5' 4" and about 120lbs, she oozed sex appeal. She had shoulder length strawberry blonde hair and azure blue eyes. Her skin was fair with just a sprinkling of freckles across the bridge of her nose. She had long shapely legs, a tight round little butt, a tiny waist, and a well developed chest that was straining to break free from the blouse she was wearing. She had unbuttoned four buttons so that her lacy bra was quite visible and showed quite a bit of cleavage as the wind whipped through the open windows of her "Baby" as we drove at 70mph down US 150 on the way home.

I was really enjoying the view when she looked over and caught me ogling her. All of a sudden she got an angry look on her face and shouted "What are you looking at?" I said "What, nothing!" She then said "I caught you, You were trying to look at my TITS!" As I tried to calm myself and answer her, she slammed on the brakes and turned off onto a dirt road and stopped behind a row of trees beside a corn field and said "Well, I'll really give you something to look at!" With that she unbuttoned the rest of the buttons and took off her blouse and threw it into the back seat.

I just sat there with my eyes and mouth wide open as she unhooked her bra and let her beauties spring free. They were more beautiful than any I had seen in any magazine and were 36Cs according to the label on the bra that went flying right past my nose as it headed for the back seat. They were round and firm with pink bubble gum colored areolas the size of half dollars and nipples the size or pencil erasers that were sticking out about a half inch. I couldn't move. All I could do was stare, until she reached over and grabbed my wrists and planted my hands on her magnificent globes. My animal instincts kicked in and I started squeezing and massaging them as she started moaning low and grinning from ear to ear.

Cindy then grabbed me by the back of the neck and pulled me to her saying "Kiss them!" I started to nibble and suck like a hungry baby moving from one to the other like a madman. She started moaning louder and slid down onto the seat facing me with her legs on either side of me with her head resting on the sill of the open car window. I continued feasting on her amazing boobies until I noticed an unusual aroma. It was unlike anything I had ever smelled before. It was exotic and very erotic and it was making me even hornier than I already was.

With my mouth on her left nipple and my left hand on her right boob, I reached under her skirt and discovered that her panties were soaking wet. I touched her between her legs and she started moaning louder. I slid my hand inside her panties and slid my middle finger between her wet folds. What happened next was something that literally blew my mind. Cindy Lou started bucking like an animal against my hand and screaming "Oh Fuck Yes Yes Yes!"

Now I had absolutely no experience with sex up till this time, but I remembered something my more experienced friends had told me and thought to myself, 'This girl is ready to fuck!' I stopped what I was doing and pulled down my slacks and underpants. When I looked back up, Cindy was sitting up straight with her arms crossed under her boobs and a concerned look on her face. She looked straight at me and said calmly "I can't do that. I'm engaged, I'm still a virgin and I have to stay that way until I'm married next year." Now I knew she was supposed to marry George, who graduated last year and was in the army in Germany. What I did next even surprised me. I pointed to my hard cock and said "What about me? You got me this way!"

Without hesitation she said "I'll take care of that". She bent down and took me into her mouth and started sucking. The feeling she gave me was like nothing I had ever felt before. Suddenly, it felt like a lightning bolt that struck me on the end of my cock and travelled all the way back to my spine and the up to my brain, and I passed out.

When I regained consciousness some time later (I still have no idea how long I was out), I was looking down at my wrinkled little weiner. The next thing I remember was looking up and seeing Cindy Lou's soaking panties hanging from the rear view mirror, and that brought me back to the world. I turned my head and saw Cindy sitting facing me with her skirt pulled up and her legs spread wide open. This was the first time I had ever seen that part of a woman, and I was completely entranced. Remember, this was the mid '60s and although nude photos were plentiful, spread leg shots were not common at all. I know now that she was an "innie", her inner lips not protruding past her outer ones. The lips looked full and swollen and were covered with fine, soft looking hair the same color as the hair on her head. The insides were bright pink and oozing a thick clear juice. I remembered the drawings in my advanced biology textbooks, but this was nothing like them at all.

She startled me from my trance by saying "OK, now it's your turn to take care of me!" I pointed to my shrunken prick and told her that there was no way I could her any good now. She said "Not with that silly, with your mouth!" I must have looked baffled because she then asked "You have a dog at home don't you?" I answered with an affirmative. She asked "have you ever watched your dog drink water?" I nodded. She said "I want you to do that to me right here." and she pointed to her soaking wet pussy. She said "Don't worry, I'll teach you." I figured that after what she had done for me, this was the least I could do for her.

So I crawled over to her and caught a whiff of that incredible aroma that was driving me crazy not too long ago and realized what it was. When I got down between her legs I stuck out my tongue and touched her beautiful vulva, it was the most amazingly delicious thing I had ever tasted. I stuck my tongue into the slit and it opened up to what looked like a miniature cavern. I licked and sucked and it opened up more.

Her juices filled my mouth and it tasted exquisite. My hormones kicked in and I went crazy. She told me to slow down and directed me as to where and how hard or soft, and how fast or slow to go. After a while, she stopped talking and started moaning incoherently. I kept up with her and soon she put her hands on the back of my head and started pushing me into her more. I picked up speed and she started squeezing my head between her thighs and I was having trouble breathing but I could no longer hear her moans. I did not stop my ministrations and increased my speed and intensity even more.

All of a sudden, Cindy Lou started shaking like she was having a seizure. Also, my mouth was filled with a torrent of copious amounts of the same juices I had been lapping and I struggled to swallow the nectar I was being fed. I hung on to her thighs and continued what I was doing, and after a while her shaking subsided and she relaxed her death grip on my head. I slowed my licking as her juices slowed, and after a while, she reached down and gently pushed my head away saying "Wow!" I sat back transfixed and watched her come down from what I was to later find out was a giant orgasm.

She eventually came out of what appeared to be a trance and grabbed her panties from the rear view mirror. She put them on and reached into the back seat to grab her blouse and bra. She got redressed without making a sound and grabbed her purse to comb her hair and fix her makeup. I watched the whole process like I was watching a scene in a naughty foreign film. I had never experienced anything like it in my life, and was never to see anything quite like it ever again. When she was finished, she started the car and put it in gear. She then said to me "you better pull your pants up." It was then that I noticed that my pants and tightie whities were still around my ankles. I also realized that my face was soaked with Cindy's juices and wiped my face with my shirt.

I pulled up my pants and we drove the rest of the way home to my parent's house without saying a word. When she pulled up into my driveway, she parked and got out to open the trunk. After I retrieved my horn Cindy Lou closed the trunk, got back in her car and drove off without saying a word. It was dinner time when I walked in the door and my mom and dad were waiting with the table food of food. My mom asked how things went and I said "We got a 1st!" My parents were very happy, and I was somewhat distracted. I told my mom I was really tired after only eating half of my dinner and said I thought I would go to bed early. My mom gave me a hug and said "I'll save you a plate in case you get hungry later." It was then that I realized that I must reek of sex, and went to my room to sleep. I was too tired to take a shower and just crawled into bed in my underwear.

I fell sound asleep and started dreaming about the day I had just lived through. When I got to the part when Cindy Lou was having her orgasm, I woke up and sat straight up in bed. I looked at my alarm clock and it was 2AM. I looked down and noticed that I had a huge wet dream and my underwear and sheets were soaked. I smelled the fingers on my right hand and they smelled like Cindy Lou's pussy! I sat there in a daze for a while and then realized that I couldn't just leave this mess for my mom to wash. I got up and went to the bathroom and cleaned myself up and got redressed. I stripped my bed and put the messy sheets and underwear in the washing machine and started a load. I went back and remade my bed, climbed in and tried to go back to sleep.

By Monday morning when I went to school, I knew I had to talk to Cindy Lou about what happened, but she went out of her way to avoid me. I took me until Friday just before 7th period Varsity Band class when I cornered her in the hall way outside of the band room. I said "We need to talk about what happened between us." She said "Nothing happened, and there is no US." I said "as far as I'm concerned, something pretty amazing happened!" She said "Jonnie, I just felt sorry for you and thought I'd give you a little thrill." And that, as they say, was that.

I grew up in a hurry after that. I was no longer the shy scared kid anymore. I started dating in earnest, but did not have sex again until I got married three and a half years later. We had two beautiful daughters and now have six grandchildren. My Connie was a year behind me in high school and we fell in love in junior college in the fall of 1967. We were married a year and a half later and celebrated our 45th anniversary just before she passed away.

As for Cindy Lou, when George got back from Germany, he found out from some of his friends about his fiancee giving them 'little thrills' while he was away serving his country, and promptly dumped her flat. He snatched the ring right off her finger, or so I was told. I guess karma really is a bitch! I do, however, have to thank her for teaching me the oral skills that have served me well over the years. I've been told many times that I am a master.

jsmangis
jsmangis
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yesterdaysyesterdaysalmost 4 years ago

What wonderful memories (fictionalized, of course) about these experiences from so long ago! 5 stars. Thanks for sharing.

AnonymousAnonymousabout 6 years ago
Nice one

Beautiful surprise fuck

AnonymousAnonymousover 7 years ago
Good job.

Married 34 years here. Never cheated, and never will.

AnonymousAnonymousover 7 years ago
Total Cape

No more needed saying

AnonymousAnonymousover 7 years ago
I hear you....

I'm a little younger than you. I lost my wife of 20+ years in 2013. My wife WAS my first time, and we had great fun making love in bed and elsewhere! I've had one serious lady friend since, and she and I gave each other plenty of outstanding oral pleasures last year. I miss them both now. I know how you feel. Thanks for writing.

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