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.