My Best Day Ever Starting with Lovely Arlene.

During my first summer out of High School, I was sleeping in on a day off from my summer job. The phone rang too early, I sleepily answered to a dull hum. There was no voice but household noises in the background on the phone. In 1960 there was no way to know who was calling, so I hung up.  A few minutes later it happened again. No voice again. I listened for a while until I heard a familiar faint noise in the background. I let  Arlene know I would be glad to see her this morning. 

Arlene was a young blonde, sixteen who hung out with my group of friends. She was too young for me but very flirty. I already had a very nice and sexy girlfriend. Life was good.  A decent summer job, my first car, and my parents working several hundred miles away for the summer, and an empty house for the summer.  Arlene let me know that she was alone and wanted to talk to someone. She made it to my house forty minutes later. I quickly straightened up the house and took a hot shower. When she arrived I almost had breakfast ready. We had a nice breakfast and went to the family room and sat together on the couch. Arlene was red-eyed as if recently crying.

When I inquired into what was wrong, I learned she was lonely and bored.  No boyfriend and her friends were busy or gone for the summer. She started to cry again and I held her close until she settled down. After a while, she began to hug me tighter and reached up to kiss me. She understood that I had a girlfriend but she needed some attention. At this time I was not very sexually experienced and only had a few girlfriends so far as working to pay my car payment and saving money for college did not leave much time for dating. We began to make out and it was delightful. It went on for quite a while and she did not stop me when I put my hands under her blouse and began to fondle her cute titties.

Things heated up and I slowly slid my hand into her panties. I was surprised at how moist her pussy was. We ultimately ended up completely undressed and still making out heavily. I slid my finger slowly up and down her pussy lips for a while. I carefully inserted a finger inside her pussy, causing her to jump. I stopped and she said it is alright but to be tender and slow. We continued to make out and caress each other. After a while, I asked her to accompany me to my recently made-up bed and we climbed on. We made out for a while and I climbed on top of her with no resistance and started to rub the head of my penis up and down her very wet pussy.  

This went on for a while and I gradually tried to put my penis in her. She was very tight and asked me to proceed very slowly and gently. She asked me if she would become pregnant.  I put on a condom and explained that it would protect her. I applied a lot of lotion and very slowly started to enter her. After about fifteen minutes I was all the way in and stroking very slowly. She seemed to enjoy it and relaxed. After about another fifteen minutes she told me her pussy was very sore and she would like to stop.

I was on the verge of climaxing for the whole time and let it go. The long slow buildup made it one if not the best orgasm I ever experienced. We made out for another half hour or so and she said she had a babysitting job would have to leave. She started to tear up again and she let me know that she hoped I would not think badly of her and that she would like to have more sex with me. I assured her I was not at all mad and would certainly love to have more sexy times with her.  Our paths did cross three more times that summer and we had sex each time until she got a steady boyfriend she later married.

Sexy Adventure number two. Later the same day. Meet Charlene a very Beautiful Lady.

After a wonderful morning with Arlene, I was going to take a nap when the phone rang again.  I was delighted to hear the voice of my older brother's ex-wife.  Charlene was always my dream girl but not wanting to create a rift in the family, I never tried to date her after the divorce.  Charlene was very stressed. She was stranded due to a vehicle that would not start and needed a ride.  To further complicate matters, she had been shopping and her car was loaded with groceries and clean laundry. 

Fortunately, her father had recommended a good mechanic and had sent a tow truck.  He could not leave work and no one else was available to assist her. I drove to the mechanic's shop and loaded what seemed like a ton of stuff into my car and drove her to her home. We unloaded the proceeds from her shopping trip into her house.  Secretly, I was really glad Charlene called me as I found her to be a very sexy lady.  Tall, slender, with red hair, creamy white skin with lots of freckles. As I started to leave Charlene invited me to have a cup of coffee, saying it was the least she could do for all I had done for her. 

We sat on the divan and drank our coffee and chatted about everything but her recent divorce.  I was surprised when she started talking about lonely she was since the divorce from a marriage that lasted less than one year.  I almost fell off the divan when she mentioned that she had often thought about calling me after the divorce but that she knew I had a steady girlfriend and did not think it would be appropriate.  I assured her I was always glad to hear from her and for her not to hesitate to call me anytime.  She again surprised me by sliding over next to me and wrapping both arms around me and proceeded to give me a very passionate kiss.

It had been only two hours since a very satisfying sexual encounter with Arlene.  I managed to respond to her passionate kisses and soon started to feel myself becoming very aroused.  This was a dream come true. The sexiest woman I ever knew is passionately kissing me in the most erotic way.  After a half-hour of making out, we started removing clothing and were soon both naked and passionately kissing again.  It did not take long for us to end up in her bed.  I was on fire.  I looked down at the long legs and her beautiful red pubic hair and her lovely firm breasts. 

At eighteen years of age, I did not have a lot of sexual experience and had never placed my lips on a woman's vagina. I had always dreamed of it, ever since I accidentally saw my uncle eating his wife's pussy when I was a year younger.  I was visiting my Uncle Pete and Aunt Sue for a week.  Uncle Pete and Sue had a poker party with another couple and played until about 2 am.  When the other couple left they continued drinking and got frisky on the couch thinking my cousin and I were asleep. 

I could hear a lot of moaning and groaning and decided to sneak a peek.   I tip-toed silently down the hall leading to the family room where my aunt and uncle were really enjoying themselves.  Sue had removed her sexy tight white shorts and had her legs over Uncle Pete's shoulders.  Pete was really eating her loudly. Sue was moaning and had both legs raised to give Pete easy access.   

I watched for about fifteen minutes and returned to the guest bedroom.  That episode changed my whole life forever.  I wanted to eat a real live pussy in the worst sort of way. The three girlfriends that had sex with me did not want to give me a blowjob and did not want oral sex from me.  However, when I saw that beautiful pink moist pussy with red hair I had to eat it. I dived in without asking. Her pussy was very damp and musky. The smell and taste were strong but divinely enjoyable.  After she had an orgasm she pulled me up and started to kiss me passionately again. I started to enter her vagina with my penis and she said I must use a condom. I sadly did not bring any.   

She would allow me to proceed if I promised to pull out before cumming.  She emphasized that she could not get pregnant as it would prevent her from completing college as well as complicate an already complicated life. I would have promised her anything to get to that beautiful pussy. I promised several more times not to ejaculate inside her.  Due to the fact that I had sex less than three hours ago, I was able to delay my orgasm for about forty-five minutes. As promised I managed to pull out and dispose of the cum by shooting it into my T-shirt which was on the bed.  We were both very hot and perspiring heavily and in need of some water and a break.

We went to the kitchen to have some water and sat and talked.  She said she always liked me but at the present did not want to start a new romance until she finished college.  I figured that was it for me until she stood up and led me back to the bedroom.  I soon was enjoying the passionate sex immensely.  After nearly another hour we were both very satisfied.  As we were getting dressed Charlene's phone rang.   Her car was ready. Over the next three years, we managed to stay in contact as friends with benefits before that term became popular.  When she got married, I realized how much I really liked her and how much I would miss her.

The Third Sexy Adventure of the Day.  Meet Janelle.

After I dropped Charlene off at the mechanic's shop to pick up her car,  It was almost 5 pm and I had spent the day having sex with two very lovely ladies.  My penis was sore and I was very tired and I still had a date with my girlfriend Janelle.  We had only been dating for six months and it had been a very good six months so far.  We both were planning on going to Junior College in the fall and both had full-time summer jobs so we could only get together once or twice a week as she lived about thirty miles away in the next town over. 

I hurried home and called Janelle and asked her if she would be up to trying out the new Steak House Restaurant she had been talking about. I had already made reservations for 8 pm, the only time available this late in the day.  She said she would love to go to dinner with me. I told her I agreed to pick her up at 7 pm.   I then took my third shower of the day, got dressed, and drove to pick her up.  As we had only been dating six months, sex was not automatic on each date and I figured that the dinner would take up so much time that she would decline tonight as we both had to be at work the next morning. 

We arrived at the new Steak House on time and were seated promptly.  In this State, no drinking before twenty-one years of age so we ordered sodas and took our time reading the menu.  Their special of the evening was a huge prime rib for two with all the trimmings including dessert.  We both thought that was a  great idea and ordered.  Dinner was elegant and served slowly.  by the time we got through the relish tray, the soup, the salad, and finally the wonderful prime rib and the bananas foster, it was 10 pm.  As I took care of the check, Janelle was smiling and indicated that she had a surprise for me. 

Her sister and brother-in-law had gone away for the weekend and she had the keys to their home.  I gave it my best smile and acted so thrilled even though my penis was still very sore from the friction and lack of lubrication on the previous two sexual adventures earlier in the day.  Janelle had me park my car in the garage and we entered. She immediately grabbed me and gave me a very nice and passionate kiss then thanked me for the lovely dinner which had taken most of my paycheck for the previous week. She offered a tour of the home and spent a lot of time showing me the beds in all three bedrooms. She allowed me to choose which one I wanted to spend the next few hours in. 

I chose the master bedroom which had a very nice king-sized bed.   She then performs a very sexy strip tease which was another new exotic thrill for eighteen-year-old me.  I had never seen such sexy and beautiful undergarments.   The fabric appeared almost transparent and very silky and form-fitting.  She told me she had been planning this night since our first week together. She had purchased the sexy undergarments and looked for a nice home that would be available and tonight was the night.  Janelle wanted to know if I had been happy with our limited sex life so far. I assured her I had no complaints. She asked if I would like to try something new or something I had never done before. 

I thought I could buy some time by suggesting that we explore oral sex before getting down to the main course.  She indicated she was very inexperienced but willing to try.  I asked if I could take off her sexy panties and bra and let me look at her beautiful body with the lights on.  She agreed and I took a long time to slide her panties and Bra off.  I was blown away. I had never seen such a beautiful body. I gently touched her long sexy legs with my hands and stroked her beautiful breasts.  I began at her breasts kissing slowly down her stomach to her blond pubic hair.  I spent a lot of time kissing all parts of her vagina. 

At this time I had never heard of a clitoris and kept putting my tongue inside her delicious vagina.  She appeared to enjoy the attention but kept shifting position to get my tongue up a little higher.  She brought me back to the same place several times and I started to lick the skin around a little bump and she became a wild woman.  I did not know what happened but kept it up for at least fifteen minutes.  By the time she finally pushed me away, she was breathing very hard and we both were covered with perspiration.  My face, neck, and chest were drenched with pussy juice, another new experience for me. 

We cuddled closely for a while and I began to think I might be able to rise to the challenge for the third time today.  Janelle got up and went to the kitchen and brought us some iced tea and we rested for a while.  She wondered if that all there is to it. Later she hinted that I should repeat what I had just done to her.  She then proceeded to do the same thing for me.  Then she really surprised me. I was lying on my back and she turned around and started crawling over my head down to my penis which was now becoming erect and ready for a blow job.  As the lights were still on I could clearly see her beautiful pussy as it passed before my eyes.  I could clearly see the pink lips and the blond hair on her pussy, a beautiful sight. 

I marveled at the beauty of her creamy white ass cheeks.  She brought her pussy to my face and started riding my tongue making sure I covered all the correct spots.  I felt her place her lips on my penis and gently lick up and down the shaft.  Due to the tenderness from the other two adventures, I was fortunate that she went slowly and gently until she got used to it.  It did not take much longer for her to figure out the basics and keeping me wet with saliva managed to give me a very pleasurable experience.  There was no danger of me cumming in her mouth at this time so I just enjoyed the various things she did, sucking my penis and balls and giving both a good tender licking. 

With her on top and still rubbing her pussy on my face, she started to flinch and stiffen her body.  I wrapped my arms around her body to slow her down as we had all night.  I realized that I would not be able to go to work the next day.  My boss gave me a list of things to complete each week and was very flexible as to when they had to be done. After a while, she started tensing up again and said she needed to finish.  I felt her start to tighten up putting more pressure on my face.  I licked long and hard, bringing about a very loud and violent event that I would later learn was a female orgasm. 

I still had not climaxed as I was saving it for the traditional sex act that was to follow.  After her climax, she rolled over and came up and kissed me needing a little rest before resuming.  We both dozed off and slept for about two hours.  I was awakened by a hand on my now fully aroused and erect penis.  She was smiling in my face and ready to give me the best sex of my life.  I could have told her she already had and been telling the truth.  She went into the bathroom and came back with a sexual lubricant and spread it on my penis and inside her vagina. 

We made out for a while and when sufficiently aroused I decided to try something new.  I rolled on my back and lifted her over my erect penis and allowed her to slide her vagina over my penis.  The feeling was divine.   I soon realized that I had much more control of my ejaculation in this position and she was able to keep her favorite spot firmly against my penis.  I believe this was pre-birth control days and I had some very nice ribbed and lubricated condoms so no fear of becoming a father anytime soon. 

The two hours of sleep completely rejuvenated me and we were able to have very nice sex several times.  About 6 am I learned that she had taken the day off anticipating that we might not get much sleep.  The house was ours for the next twelve hours. No need to tell you, but we did not waste any of the next twelve hours on anything but sex and an occasional meal. 

Janelle never knew that I had sex with two other ladies prior to her that day.  We dated for the next year and got along famously.  For reasons I do not remember, she dropped out of college and got a better-paying job.  I stayed with my job and finished two years at Junior College which qualified me to transfer to State University.  We saw less of each other the last year and upon completion of two years of college,

I joined the army and had a great adventure I never regretted.  On returning home, Janelle was a different person, probably because I was a terrible letter writer and did not stay in touch.  Letting the fire go out was truly one of many big mistakes I have made in my life. We dated for about a year and slowly drifted apart. I thought of her for many years and attempted to get her back.  We both knew it would never be the same.

This ends the saga of my one and only triple header, having sex with three ladies on the same day. Of course, the names are not real the ladies are very real. I hope I changed enough things about time names and places that no one will recognize who they are.

If I manage to get this writing accepted and printed, I have many more adventures to share.  I was a bachelor until I was forty years old. It was not my choice, I took a long time to find the proper life partner who would love me and stay with me all my life. I allowed too many to slip away before I made up my mind.  I will say it was worth it in the end as I married a true angel and we have been married for a very long and happy time...