Women in My Life Ch. 02

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.

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INTRODUCTION

During the months that Charlie and I had sex together I was having sex with other girls as well. She was also having sex with other guys it was just the way things were at that time. In addition to the women who I will write about in more detail in subsequent chapters, there was also Sandy, Karen, Toni, April, Donna, Sharon, Lee, Gina, Betty, Sherry, Angela, Paula, Terry, Andrea and Cathy. In this chapter I will tell you about Sandy, Karen, Susan and Pamela.

SANDY

Sandy was a cute girl in her mid-twenties with long light brown hair. She was about 5'4" tall, weighed about 110 and she had a nice set of tits. The rest of her body was shapely and curvy but when she was naked her tits looked a little big for her smaller body. She was a good lover but she was not into oral or anal sex at all. Sandy's problem was that she was a compulsive liar, which cost her marriage and her job. She was divorced when we first went out and I often caught her in lies while we were seeing each other.

Sandy's favorite position was to ride my cock in bed. She went along with the missionary position but fucking from behind either spoon or doggy style was out. On one of my business trips to Chicago I stayed for the weekend and I had Sandy fly up on a Friday night. After a dinner in the city we made love in the hotel room with me cumming in her pussy twice that night. Sandy liked to keep the lights off when we fucked as she seemed a little insecure. On Saturday we did some sight seeing and had a nice dinner out before returning to the hotel room. Once again we fucked with the lights out. It was the missionary position first and then Sandy rode my cock until she had multiple orgasms and I came again.

On Sunday Sandy asked that we stay in and order room service. After breakfast that morning she decided that she was going to see how many times she could make me cum that day. This time we left the lights on but Sandy kept her nightgown on. Sandy straddled my cock as I sat in the bed and bounced up and down on me until I shot my first load. She had cum a couple of times before I did.

Sandy then stroked my cock to get it hard again and she even used the body lotion provided by the hotel. She poured an ample amount in her hands and rubbed it all over my cock. When the lotion dried on my cock she added her saliva to her hand and stroked me again. When she had my dick hard and slippery she straddled me again and lowered her pussy on my cock.

I reached under her nightgown and fondled her big tits as she rode my cock. Then I lifted the nightgown off her body. Sandy weakly protested as she did not want to be naked with the lights on. I still think she was subconscious of her big tits. I persisted and the nightgown came off and I played with her tits the rest of the day as we fucked. Each time after I came or went soft in her pussy, Sandy stroked my cock again with her hands. I tried to get her to suck it but she would have nothing to do with oral sex. I came three times that day which for me was the max at that time in my life.

After the Chicago trip my time with Sandy tapered off. Sandy would make up lame excuses all the time and I was convinced that she was a perpetual liar. One time she left me at the airport when she was supposed to pick me up. I learned from her friend Cathy that she was with another guy. Another time I went to pick her up at her place and she was in bed with another guy. Later Sandy explained that she didn't feel well and I told her that I hoped having that guy's dick in her made her feel better. Sandy was habitually late for work and she was eventually fired. I never saw her after that.

KAREN

Karen was a cute little 27 year old natural redhead. She weighed just over 100 pounds, stood at about 5'5" and had very small breasts. In fact Karen had a very straight lined figure and a small ass to go with her small tits. Karen's best asset was her mouth and she loved to suck cock. She liked to fuck too but she was just as happy with fingers in her pussy as she was with a cock in her. She didn't like to have me cum in her pussy so if I was fucking her I had to pull out and either cum on her or in her mouth.

Karen was another corporate groupie who liked to hang around the Oasis. She had been married once but now she had no interest in a long term relationship which was fine with me. Karen and I got together about five times before she started seeing one of my buddies on a regular basis. The routine with Karen was usually the same as we would be drinking after work at the Oasis and Karen would invite me back to her place for coffee. Of the five times we got together we had coffee once.

I still remember the first time with Karen as I moved on her as I would any girl. Once we had our clothes off and we were in her bed I began my oral trip from her lips over her tits to her pussy. But Karen stopped me before I got to her pussy as she did not want me to eat her. Then she made her move and took my cock in her mouth. Karen was an incredible cocksucker and she had me cumming in no time. I filled her mouth and she swallowed as fast as cum shot down her throat. Karen held my balls and tickled my perineum with her fingernail as she gulped down my seed.

Karen loved to keep sucking my cock after I came until I was hard again. Karen then had me fuck her and she had multiple orgasms before I was ready to cum again. Karen told me to cum in her mouth again when I was ready. As soon as I felt my balls tighten up I pulled out of her pussy and knelt by her face. Karen took my cock back in her mouth and I fired another good size load down her throat.

One other time we were together Karen had me shoot cum on her body. We had started out fucking but when I felt my ejaculation building I pulled out of her and aimed my cock toward her face. I held my cock tightly as my seed traveled up from my scrotum. When I couldn't stand the pressure any longer I released the grip on my cock and stroked it as cum flew out of it. The first ribbons of cum hit Karen's red hair and freckled face and the subsequent streams sprayed her tits and abs. The remaining semen trickled over my fingers and dribbled down on her pubes. Karen then licked cum off my fingers and then took my cock in her mouth to suck me dry.

The best thing about Karen was that our get togethers were always spontaneous and unplanned. I enjoyed every minute I was in Karen's bed even though I never got to fuck her ass or eat her pussy. Karen started dating a guy named Bruce and they hit it off. Karen then stopped hanging out with us as she and Bruce were inseparable

SUSAN

As I mentioned in Chapter 1, I met Susan at a party and after I fucked Charlie in the ass, Susan and I left the party and went to her apartment. At 23 years old Susan weighed just under a 100 pounds and she had the typical model figure. Even though she was thin she had the curves and bumps in the right place. Susan had small firm cute tits, shapely slender legs and a very cute round bubble butt. She wore her blonde hair short just over her ears. Susan was a natural blonde and she the cutest little tuft of blonde fuzz on her pubes.

Susan was not at all into giving head but she loved to have her pussy eaten as I learned that night. We wasted no time in getting our clothes off and into Susan's bed. Since I had already cum once that night I was in no hurry to get my rocks off. In fact I focused all my attention on Susan's pleasure. We kissed with our naked bodies rubbing together and I fondled her tits and curvy ass. Then I began my pursuit down her body. I spent quite a bit of time sucking on her tits and nibbling on her nipples.

I left her tits and trailed kisses over her abs down to her pubes. I skipped Susan's pussy and kissed her inner thighs. Susan had her head thrown back and her mouth was wide open as if she was going to scream but no sound ever came out. I moved my mouth to her pussy and flicked my tongue over her vulva. I probed her outer cunt lips with my tongue and then drove it in separating her inner lips. Susan's body tensed as I worked on her pussy as if she was going to cum. I swabbed my tongue around inside her pussy and flicked it over her hooded clit.

I pushed a finger into Susan's pussy and wormed it around as I tickled her clit with the tip of my tongue. Susan's body went into convulsions as her first orgasm overtook her. She grabbed my head and held it to her pussy as she humped my face for all she was worth. I held her tightly as she sprayed my face with her female nectar. Susan had a very tasty pussy and I enjoyed eating her to multiple orgasms. Susan's mouth was still wide open as her body lifted off the bed. I grabbed onto her cute ass firm cheeks and held her tightly against my mouth. Susan then shook violently and collapsed on her bed.

I kept right on eating her and I soon had her aroused again. This time I pushed a pussy lubricated finger into her tight asshole causing Susan to freeze. I was to learn later that it was her first anal penetration. Susan went along with it as it felt strangely good to her. Susan then asked me to fuck her so I moved between her legs and slipped my rock hard cock into her very wet but snug pussy. Susan gasped when my cock hit home and I was to learn later that I was the biggest she had had in her up to that time. Susan was so thin that I could feel the sharpness of her pelvic bone as I fucked her. Susan worked to keep her clit in contact with my cock and in no time she was cumming again. Susan thrashed and writhed under me as she had a mind blowing orgasm.

Susan then asked me not to cum in her pussy. I learned later that she was nervous about where she was in her cycle, better safe than sorry. I pulled out of her and laid my cock on her abs between our bodies. I kept moving as if I was fucking her and then I shot my load between our bodies. My semen shot out of my dick but it was immediately trapped between our bodies. Susan thanked me for pulling out of her pussy and she told me it was cool to cum on her rather than in her. Susan and I lay together for awhile longer and then I cleaned up, dressed and left for home.

The next time Susan and I got together I was on my way home after having a couple of drinks at the Oasis. Susan was coming in just as I was leaving. I told her no one was at the bar but I offered to buy her a drink if she wanted one.

Susan smiled at me with her sultry look and said, "No, why don't we go to my place and fuck."

"Sounds good to me," I replied and then I followed Susan as we drove over to her apartment.

Just as we did the first time we wasted no time getting our clothes off and getting into her bed naked. Susan was really horny that night and she came quickly and often as I ate her pussy and fucked her. I still had not cum when she asked me to stop and let her rest for awhile. Thinking that her pussy needed a break I asked her about anal sex. Susan told me that she had thought about it but never tried it and that my finger was the only thing that had ever been in her ass. I talked her into taking a bath with me thinking that I could get her ass clean and then turn her on with my tongue.

Susan ran a bubble bath for us and when we sat in the tub she leaned back into me. I reached around and played with her titties and her pussy for awhile. Then I moved my finger to her ass and I used the soapy water as lubricant as I finger fucked her ass. Susan got used to the penetration and allowed me to finger fuck her bottom. Then we got out of the tub before we turned into prunes and dried off.

I had Susan lay face down on her bed and I pushed her cute round ass cheeks apart and exposed her delicate nether hole. The pink aperture looked squeaky clean and I lowered my tongue to her asshole. Susan gasped when she felt my tongue rim her anus. At first she stiffened and then she relaxed and enjoyed the oral stimulation. Susan was clearly getting turned on and she let me know it.

"Walt you really know how to get a girl turned on," she sighed.

I lifted Susan up by her hips and then I began to lube up her tight ass with her body lotion. I wet my finger and it slid in easily when the saliva mingled with the lotion. I finger fucked her asshole and then added a finger to her pussy so that I was finger fucking both her holes at the same time. Susan put her head down on the bed and turned it to one side with a look of ecstasy. I decided it was time to go for it. I removed my fingers from her ass and pussy and lined up my rock hard cock with Susan's asshole. I pushed slowly but she was too tight and her sphincter did not open easily. The head of my cock was just starting to open up her rosebud when Susan screamed in pain and panicked. She moved away from me and threw herself face down onto the bed.

"No don't, it hurts too much. I don't want to do this," she pleaded.

I leaned over and whispered in her ear, "I don't want to hurt you. Don't worry I won't fuck your ass."

Susan rolled over and held her arms out to me and I moved between her legs and slid my raging hard-on into her tight pussy. We fucked liked demons until I blasted a huge load into Susan's pussy. Susan came multiple times again and then she went limp under my body. I was still hard after cumming so I continued to fuck her.

"No please, give my clit a break. I can't take any more tonight," Susan begged.

I pulled out of her and rocked back on my legs. Then I rolled Susan over into a doggy-style position and slipped my cock back in her pussy. Susan was in a totally relaxed state and she let me have my way with her in this position. I played with the cheeks of her cute bottom as I fucked her from behind but I did not penetrate her ass again that night. I eventually came for a second time and once again flooded her pussy with semen. Susan dropped face down on the bed as she was done for the night. I washed up in her bathroom, dressed and then kissed her on the cheek when I left.

The next day Susan stopped by my office. She came in and closed the door. I could tell that she was nervous or almost scared.

"Walt, there was some bad stuff that came out of my ass this morning. You can't ever put anything in my ass again. I don't want you near my ass again," she rambled in a panic.

"Susan I understand. Look I know it was the combination of the lotion and a stool that made it look so bad. You're okay you're not injured. I stopped as soon as you told me too," I replied trying to put her at ease.

"I don't know what it was but it looked nasty and it scared the hell out of me," she countered still shaken.

"I'm sure it scared you but I promise you I know that you will be fine. I never did penetrate you," I said trying to calm her.

"I know that you didn't penetrate me. Thank you for not forcing yourself on me. I know that you care and that you are a good lover. I just freaked out," she said almost sobbing now.

I stood up and held her until she calmed down and relaxed in my arms. Susan eventually left my office composed but she was resolved that anal sex was not going to happen with her.

Susan and I got together a few more times and we always had great sex. She started dating a pilot for one of the charter companies so my time with her came to an end. But one night after one of our softball games Susan showed up at the Oasis. She asked me back to her place and I guessed the fling with the pilot was over. We made passionate love that night and afterward as we lay naked together Susan told me that she hadn't heard from the pilot in weeks. She had been too proud or too stubborn to call him and she was upset. It was obvious that she really liked the guy and she was devastated that he had just dropped out of sight.

I told her that she should call him and clear the air one way or the other. Susan agreed and just then the phone rang. Susan grabbed the phone before the second ring and I watched her face break into a joyous expression.

"Hi, how are you? I was just going to call you. I've been worried about you," Susan rambled on.

It was odd because we were both naked in her bed as she got caught up with her pilot boyfriend. I slipped out of bed and quietly got dressed. Then I leaned over and kissed Susan on the forehead and gave her a thumbs-up as I left. She smiled at me and blew me a kiss as I left her apartment. That was the last time Susan and I made love.

PAMELA

Pam worked in a different division in our company and I met her one night at the bowling ally. Pam was definitely the most adventurous lover that I had had to that point in Ohio. She liked to take risks and seemed to thrive on the possibility of getting caught. Pam was engaged to be married and the idea of her fucking around on her fiancé seemed to turn her on.

Our company had a bowling league that met every other Tuesday, which I also participated in. After bowling many of us adjourned to the lounge for drinking and dancing. It was in the lounge that I met Pam. I walked in and sat down at the tables that we had pushed together and Pam sat right next to me. I had seen her in the league but I had never actually met her before that night. I introduced myself to Pam and she was definitely hot to trot. I couldn't help but notice her engagement ring but that didn't keep her from coming on to me. Some of the people at out tables started dancing and I asked Pam if she would like to dance. She enthusiastically accepted and within seconds we were slow dancing on the dance floor. Pam held me tight and pushed one of her legs between mine. You couldn't have passed a ray of light between our bodies, that's how close we were to each other. My cock stiffened in my pants and it rubbed along Pam's thigh. She clearly felt it and moved her hips even more seductively and rubbed against my cock.