Women in My Life Ch. 01
Author's note: Based on reader feedback and requests, I decided to write a series of stories that are based on women that I have had sex with in the course of my lifetime. This period would normally cover my high school senior year 1959 and the years in the Marine Corps (1959-1963) up to the current day. I will not cover every encounter since by my count I have had sex with almost 50 different women starting back in 1959. I will select my best encounters and I will write about them randomly rather than in chronological order. I will not include any of my bi-sexual experiences when I let men suck my cock or when I fucked them in the ass.
These encounters will include anal sex, oral sex, vaginal sex and infidelity. There is also some bi-sexuality between women and some group sex. If this is not to your liking then I recommend that you not read the stories. This is a period when people slept around and condoms were rarely used. People began to cool it around the mid-1980s when the threat of AIDS became serious. Guys that slept around were called studs and unfortunately if girls slept around they were called sluts. I never agreed with that because I felt a girl had every right to have an occasional roll in the hay as any guy did.
A few of my stories about certain women are already on the Literotica site and I will touch briefly on those encounters. I will begin with 1970 since many of my encounters, in high school, the Marine Corps and my life between 1963 and 1970, I used in writing other stories already posted on Literotica. Each chapter will be named for a girl or group of girls and it will be based, and I emphasize the word based, on real experiences but the names will be changed and the sexual encounters will be embellished for readership. Some of my previous stories that are on the Literotica site are based on some actual experiences, these include; Capri an Isle of Love; An Affair to Remember, Thanks for the Memories and MILF and Did. I know that many readers do not believe authors when they speak about writing of their experiences but I will leave that interpretation up to the individual reader. Others who read this may call me a womanizer or male chauvinist pig. What ever you think while reading the stories the fact is that is the way it was at that time at least in the circle of people that I hung out with. We had sex, we had fun and no one got hurt. I hope that you enjoy this work for literotica. As always all characters are 18 years old and older.
INTRODUCTION
I worked for a multinational company headquartered in Midwest. The company had just moved the headquarters office from the East Coast to Midwest. I worked for that company as one of the managers in the IT Division from 1970 through 1976 during which time I had sex with about 20 different women. Our temporary offices in Ohio were located in a suburban area while our new company building was being built in the city.
CHARLOTTE
The first name I selected is Charlotte. She preferred to be called Charlie and she was one of the corporate groupies at our company. The story takes place in the early to mid 1970's, a time when everyone was sexually promiscuous and condoms were rarely used.
There was a bar that all of us hung out at called the Oasis which also sponsored one of the softball teams I played on. I also played for another bar and our company team. All three teams had many of the same ballplayers and we actually did very well in our leagues and in tournaments. Softball tournaments were huge in the Midwest back then and we were in at least two a month. It was at a softball tournament that I first hooked up with Charlotte.
In 1970 I was 29 years old and I was a fit 6'1" 205 pounds. I had light brown hair, hazel eyes and I worked out all the time. I was an avid down hill skier, SCUBA diver, tennis player and golfer in addition to the softball teams. Charlie was a 28 year old brunette with brown eyes, about 5'5" and 120 pounds. She was not the prettiest of girls but she wasn't ugly either. Charlie had served in the Army before she worked at our company so she was no virgin and no stranger to brief encounters.
We had won our first two games in a 16 team double elimination tournament and we had the whole afternoon. We were not scheduled to play again until 8:00 PM that evening in the third round of the winner's bracket. My friend Al Palma had his girlfriend Ginger at the game. Ginger was good friends with Charlie and she had accompanied Ginger to the game. Al invited me to join him and Ginger at her house for lunch and a few pops between games. Ginger introduced me to Charlie and she confirmed Al's invitation.
When we arrived at Ginger's house her first words were that we all had to take showers before we used the beds. I was surprised but not shocked at her announcement. I knew Al was banging Ginger on a regular basis so it was not a surprise that the two of them would jump in the sack.
Charlie just smiled at me and said, "Come on I'll show you where the guest shower and bedroom are that is unless you'd rather watch TV."
"Lead the way," I replied not wanting to pass up an opportunity for some afternoon delights.
Charlie and I stripped down and entered the shower. She had a large birth mark on her shoulder that she was embarrassed about but I quickly put her at ease. I started to soap up her tits, ass and pussy but she stopped me.
"Let's save that for the bedroom. Ginger doesn't like it when the shower runs too long," she told me.
Charlie had obviously done this before at Ginger's place and I followed her advice. We washed ourselves quickly and then went into the bedroom. Charlie lay on the bed and opened her legs for me. She held up her arms and welcomed me into her body.
"I had been hoping that we would get a chance to make it together someday," she whispered.
Slowly, I moved into her. Charlie opened beneath me, enveloping my penis tightly. Her cunt was like a fist as she clenched her vaginal muscles. She squeezed me as I moved within her.
"Charlie," I groaned, "You are really tight."
She moaned in response, "Your big cock feels so good. Fill me up with it."
I thrust into her deeply and I felt the head of my cock pressing against her cervix.
"Oh Walt," she sighed with her eyes closed.
I felt her vagina contract around my cock. She climaxed again with a shudder and a long moan and she urged me on, "Fuck me baby. I can take it, I want it."
I grabbed her hips in my hands and began to thrust in and out as I pounded her pussy. My heavy bloated testicles slapped against her ass as my cock drove into her hot pussy.
"Yes, oh yes," she gasped as her body rose to meet me.
The bed was now rocking with the force of our fierce, animalistic fucking. Her legs clamped around my waist as she screamed her release. Her pussy grasped my cock, squeezing it and milking it as I fucked her. I moved my hips against hers and buried my cock to the hilt within her. Her quaking pussy erupted into orgasm again as I rocked my cock slowly, grinding the head against her cervix. I felt my orgasm building in my balls and I knew that any second I would be spewing my seed into her womb. I felt my semen travel from my scrotum through my cock as I came deep inside her flooding her waiting warmth with my load.
Neither one of us could speak as the pleasure was so intense. I collapsed on her and she wrapped her arms and legs even tighter around my body. Not wanting to crush her I rolled off her as my cock deflated and slipped from her cum filled cunt. We rested together as we talked for awhile. Charlie knew that I was fucking a few girls from the office and she had told Ginger that she would like to make it with me, which is why Ginger invited her to the tournament. I learned that Charlie had been married but was divorced in the Army. She also told me that she was not at all into oral sex either giving or receiving. Charlie reached down and stroked my cock as we talked and I fondled her tits and played with her pussy. Before long we were turned on again.
I pulled her legs apart and let her guide my cock into her pussy. I eased my thick cock into Charlie's tight cunt and worked it slowly until I was balls deep in her pussy. I knew that with her tightness that she could probably feel every ridge and vein of my cock touch her vaginal wall. Charlie gasped again when I hit bottom. As I fucked her slowly I made sure that my cock never lost contact with her clit. Charlie stiffened as she orgasmed and then grunted and groaned through multiple orgasms as her body was rocked with one climax after the other. As I pounded her pussy my cock moved easily in her now soaked pussy. Charlie stiffened one more time, screamed and then went limp with her final orgasm which was the most intense of the day.
Once again I rolled off Charlie and this time she rolled over on her stomach. I caressed her ass and teased her between her ass cheeks. I searched for her nether hole as I massaged her bottom. I finally reached the object of my desire and I rubbed juice from her pussy into her asshole. She lifted her hips slightly as I worked her firm ass cheeks. I pulled her buns apart slightly and stared at the cute little aperture. I traced my finger over the ridges of her now swollen sphincter and watched as it seemed to pulse and throb under its own accord.
I scooped more juice out of her pussy with my fingers and pushed it into her asshole. Charlie's hips bucked in response to my probing. I loved anal sex and I loved to watch my cock slide in and out of a hot ass. I was hoping that Charlie was into anal sex. As my finger entered her channel she gripped it with her anal muscles. I continued to finger fuck her ass adding more natural lube from her pussy as needed and eventually I added a second finger. Satisfied that she was well lubed I straddled her hips and guided my slick cock into her pussy to coat it with juices and then I eased it into her ass. My cock head slipped past the moistened sphincter and the spongy head disappeared into her ass. Her anal ring snapped closed behind the cock head and I marveled at the sight before me. I only had the head of my cock in her and she lifted her hips and pushed back obviously wanting more.
"Not too deep at first and then go deeper," she whispered.
My cock felt bigger than it ever had as I eased more of it into her anal passage. I watched as it stretched her open and slid easily in her slippery hole. I continued my slow penetration until the entire length of my shaft was balls deep in her ass. Charlie gasped and grabbed the bed sheets as I hit bottom and then moved her ass in time with my thrusts.
"Let's fuck on our sides," she rasped.
I rolled both of us to our left side and settled into the spoon position with my cock buried in her asshole. My left arm came around and fondled one of her tits and tweaked her nipples as my right hand sought out her pussy. I pushed two fingers into her pussy as I fucked her ass and played with her tits. Charlie was going wild as her orgasmic, constricting muscles gripped me firmly.
We fucked slowly as she arched her back and we fitted together perfectly. Her gasps were intermittent and interrupted with cries and sobs of pleasure. Her ass was so snug that I wondered how the semen ever got out of my cock. I fought to hold back my orgasm as long as possible but the undulating walls of her asshole were just too much. I felt the familiar boiling in my balls and I thrust into her as the first blast of cum exploded into her rectum. I barely heard her pleas for me to fill her ass with cum as her contractions milked every drop from my cock. I continued to fuck her slowly and I enjoyed the new feeling of warm semen mixed with the pussy juice surrounding my cock in her sheath.
"I love the feel of your warm cum in my ass," she sighed as my cock remained nestled in her hole.
Charlie told me that she loved anal sex and that sometimes he actually preferred it to vaginal sex. She said that she still wanted to cum and she preferred a cock shooting a load in her ass while her clit was being rubbed. We remained in the spoon position for quite awhile. I think we even dozed and we were awakened when my deflated cock slipped from her ass. Charlie rolled toward me and smiled as she whispered.
"That was some great sex today, you are a good lover," she said softly and then, "Come on it's time to get up and get dressed."
Charlie and I showered quickly and dressed. She told me that she first had anal sex in the Army and over time she had become addicted to it. Charlie told me that she liked anal sex as much as vaginal sex and sometimes even more with the right person. When we went into the kitchen Ginger had already put out some snacks for us. The four of us ate and then we returned to the tournament. We won our third game and the next day we would be playing in the winner's bracket championship.
On Sunday we lost the first game and we had to play the team coming out of the loser's bracket. We beat them and then we had to beat the same team twice to win the tournament. We won the first game but then they came back and beat us in the championship game. It was tough playing four games back to back but that's what can happen in double elimination tournaments. All and all it was a good tournament for us. I was pretty tired as was the rest of our team so we passed on drinks at the Oasis and headed home. Tomorrow was a work day.
The Party
I didn't see Charlie again until Friday that week. Terry a girl who worked in corporate and her current squeeze Russ had a party at Terry's house. Terry was divorced with a couple of kids and the kids were spending the night at her parent's house. I went solo to the party since I wasn't really dating anyone.
Another friend and ball player, Manny was supposed to meet Charlie at the party but he showed up with a last minute date named Cindy. Charlie was miffed but she kept her cool but by the time Manny had arrived just about everyone had paired off. I had my sights set on a cute thin blonde named Susan. I was drawn to her more by her outfit at first. She looked very stylish and she wore a cap that made her looked very British. I expected an English accent when I spoke to her but I learned that she too worked in corporate.
Charlie approached me and asked if she could speak with me just for a minute. I excused my self from Susan to speak with Charlie. "Can you meet me down stairs in a few seconds?" she asked.
I told her I would but I noticed that she had been drinking heavy. I went down the stairs a few moments after her and she ushered me into the bathroom on the lower level. Charlie closed and locked the door, turned her back to me and pulled down her shorts. She was not wearing any panties under her shorts. It was a new style outfit with a halter top and the matching tops and bottoms were held in place by elastic. Charlie had elected not to wear panties under her bottoms and as I found out shortly she passed on the bra too.
"I need you to fuck my ass before you head out with Susan," Charlie requested slurring her words a little.
I dropped my pants and underwear and I pushed my fingers in Charlie's pussy. I moved my fingers from her pussy to her asshole for several minutes gathering her pussy juice and lubing her asshole. Then I pushed my cock in her pussy and got it good and wet before I eased it into her ass. Charlie grunted as my cock hit home and slid into her ass. We both fucked rapidly as I pushed her top up over her tits and played with her tits and nipples. I reached with one hand for her pussy and plunged two then three fingers into her quim. Charlie went wild with the double penetration and the manipulation of her tits. She soaked my fingers with her female juice as she had a string of orgasms.
Then I felt my seed shoot through my cock into the depths of her ass causing Charlie to groan loudly. She milked my cock dry with her talented anal muscles and her hips thrashed uncontrollably ejecting my cock from her ass. I held her tightly and my wet cock brushed against her creamy ass cheeks.
"Oh thank you, thank you," she cooed as her body calmed.
I washed my cock off in the sink and then dressed and returned to the party. Charlie stayed in the bathroom longer before she left and by the time she left I did not see her. I was talking with Susan again when Charlie left and not long after that Susan invited me to her apartment. The time I spent with Susan that night and several other nights will be covered later.
Charlie Revisited
It was a few weeks before Charlie and I hooked up again and it was quite by accident. I had worked late one night and I stopped off at the Oasis for a night cap. It was a slow night and I was the only one in the bar until Charlie came in. She had been out bar hopping and hadn't found anything to her liking so she decided to swing by the Oasis on the way home. She had not eaten dinner so I suggested that we grab a snack and a drink together.
Charlie and I sat side by side at a bar table facing the bar. The bartender Dan was engrossed in the TV watching a ball game and getting caught up on all the scores. As we ate our burgers and sipped our beers, I ran my hands over Charlie's nylon covered thighs. She was wearing pantyhose under her red mini skirt but no panties. I slid my hand between Charlie's thighs and covered her hose protected pussy. I rubbed her cunt through the hose and her pussy got sopping wet. We finished our burgers and beers and then left the Oasis. When we got out to the parking lot I asked Charlie if she wanted to sit in my car for awhile.
"You better believe it, as worked up as you got me in there you better take care of me," she replied excitedly.
Charlie and I got in the back seat of my two-door Grand Am and I immediately peeled off her panty hose. I lowered my pants and underwear to my knees and the two of us played with each other for several minutes. The Grand Am had louvered rear windows so it was impossible for anyone outside the car to see in the back seat. There was something very erotic about being partially clothed but still having access to each other. Charlie had her legs spread wide as I fingered her pussy and pushed her cunt juice into her ass. Charlie stroked my cock with her hand as I prepared her for another ass fuck.
I never knew anyone like Charlie who could get so wet during foreplay. My hand was sopping wet and within minutes I had her asshole coated with her own pussy juice. I positioned Charlie so that she was kneeling down on the back seat and I knelt behind her. I put my cock in her pussy and let it soak in her juices before I lined it up with her ass.
Once again Charlie reminded me, "Not too deep at first and then deeper."
I eased my cock into her asshole as she maneuvered her body to accommodate the anal penetration. Charlie had her head down on the car seat turned to one side and I watched her face grimace slightly as my cock made its way into her ass. Charlie moaned and groaned as I slowly fucked her going a little deeper in her ass with each thrust. Once I was all the way in I picked up the pace and fucked her until I flooded her ass with my cum. Charlie had her fingers buried in her twat and she brought herself off as I plowed her ass. When my hips stopped moving Charlie milked my cock with her anal muscles and then her hips gyrated as her own orgasm overtook her. I had to hold her tightly to keep my cock in her ass as her hips jerked out of control.
My cock softened and I eased it out of Charlie's ass. I knelt there looking at her recently violated asshole and watched as my semen trickled out of her rectum. Charlie remained still for a few minutes with her red dress thrown up over her back and her ass on display. I had some napkins in the car and she used them to wipe the semen from her ass before she sat down on the car seat.
"You definitely have the largest cock that has ever been in my ass. Do you know how big it is?" Charlie asked.
"Well Karen measured it one time when she was blowing me and she said it was between 7 -- 8 inches long and just over 5 inches around," I replied.
"It certainly felt bigger than that tonight," Charlie sighed.
"At times I do feel thicker and longer but I have never thought about my size very much," I admitted and added, "I know that there are plenty of cocks bigger than mine."
"I think tonight was one of those nights that you peaked and your cock is plenty big for me," she said with a giggle.
Charlie did not bother putting on her pantyhose when I pulled up my pants. I opened the car door and we got out of the back seat. Charlie said that she was glad that she ran into me and that she would see me later, then she said goodnight and made her way over to her car. I watched as she got in her car and as she did her skirt flew up and flashed her bare pussy. After she left the parking lot, I drove home in a very sated state.
It was at least another week before Charlie and I met up again. It was a repeat performance with me stripping off her pantyhose in the back seat of my car, lubricating her ass with her own juices and fucking her tight ass. It was exciting for me to strip off her hose and fondle her legs, pussy and ass. Charlotte seemed to like being without her panties and hose in the back seat of the car. I took my time with her, fingering her pussy and ass driving her crazy, until she finally begged me to fuck her.
My Final Session with Charlie
It was another night at the Oasis and Charlie had had too much to drink. I put her in one of the booths toward the back to let her sleep it off and I told her girl friend Ginger that I would take her home later. Ginger and Al were anxious to get going that night and they didn't want to wait for Charlie to wake up. They thanked me and left and I joined Dan at the bar for a night cap. I didn't drink too much since I was driving and after a while I decided to take Charlie home. I picked her up and carried her out to my car all the while I hoped that she wouldn't get sick. I placed Charlie in the front seat and buckled her in. Charlie woke up and told me that she was staying at her sister's pad that night. She managed to stay awake and give me directions to her sister's place.
Once we arrived at her sister's, I helped Charlie into the house and the guest room. It was late and I assumed that her sister was asleep in the other room. Charlie flopped down on the bed and I then had the urge to fuck her before I left. I moved over to the bed and stripped Charlie naked. I removed her blouse and bra, her shorts and panties and her shoes. Then I stripped down naked and got in bed with her. It was the first time that we were totally naked together since the very first time we had sex.
I rolled Charlie to her side and she knew what was coming next. I scoop her female juice from her pussy and used it to lubricate her asshole. Charlie cooed as my fingers probed her pussy and lubed her ass. Then I placed my cock in her pussy just for few strokes to get it slick. I positioned my cock at her ass and gently pushed my cock into her.
"Not too deep at first and then deeper," Charlie whispered those familiar instructions.
I did what she asked and as I fucked her ass I went a little deeper each time. Soon I was balls deep in her ass and I picked up the pace. My cock felt longer and thicker than I could remember at that moment. I reached around Charlie with my left hand and played with her tits and rock hard nipples. Then I moved my right hand to her pussy and pushed three fingers into her cunt. Charlie was going wild and she was creaming all over my fingers as I plowed her ass. My cock was throbbing in her asshole and I felt my pending ejaculation building in my balls. One more deep thrust and I held my cock there as I exploded in her ass. My cock pulsated as streams of cum shot into her ass. Charlie instinctively clenched and unclenched my cock with her anal muscles. She milked every drop of cum from my cock.
For some reason I stayed hard that night and I kept right on fucking Charlie's ass. I knew it would be a while before I came again so I pulled out of her ass and rolled her on her back. Then I pushed my raging hard cock in her pussy and treated her to an exhilarating fuck. I kept my cock in constant contact with her clit and I had Charlie writhing and trembling as a continuous string of orgasms rocked her body. Then I pulled my cock out of her pussy and rolled her back to her side and re-entered her ass. I pummeled her ass as I sought out my second orgasm of the night. Charlie's ass was loose and slippery from our combined juices but she was still snug enough around my cock. Once again I stiffened and fired a barrage of cum into her rectum. I could feel my cock pulsate again as it released a torrent of cum deep into her anal recess.
We lay still for a few minutes recovering from the intense fuck session. I had forgotten about my cock in her ass until it had softened and slipped from her hole. I felt my wet cock drop on my thigh and I knew that cum was trickling out of Charlie's asshole.
"I wish you could stay with me tonight," Charlie whispered.
"Not tonight Charlie, I have to be up early in the morning. Plus I don't think you want your sister to find us in her guest bed in the morning either," I replied.
Charlie just nodded her agreement and then I got up to get dressed. I dressed and left the house quietly and then drove home. It was the last time that I had sex with Charlie. Our company was going through some downsizing and Charlie was one of the casualties. She ended up taking a job with another company and she stopped hanging around the Oasis and her former co-workers.
NEXT CHAPTER
In the next chapter I will write about my experiences with Sandy, Karen, Susan and Pamela.