Other's Wives/Girlfriends Ch. 01: Karen

This series of stories are mostly true, based on the journals I've kept through the years and my memory. Most of the names have been changed to protect the innocent, or not so innocent. No one (except maybe my wife) would ever describe me as good looking, much less handsome. I'm short, about 5'6", medium build, with a somewhat large nose and projecting ears. As a teenager, I was downright skinny. What I do have working for me is a sense of humor and a gift of gab. Somehow, I've had a good deal of success bedding some very beautiful women, most of whom were married, engaged, or otherwise committed. I'm a professional that has enjoyed a modicum of success in my professional and personal life. I've also been very fortunate to find, not only one, but 2 loves of my life. A few years after my first wife of over 30 years died of complications from surgery, I met my current wife a few years later and have enjoyed married life again.

During my senior year in high school, I developed the habit of ending each day by writing in my journal which I do to this day. After my heart attack at age 50, I transferred my journals to computer files so I could better maintain the confidentiality in them. The sexual encounters portrayed in my stories are based on my notes and recollections. I hope you enjoy them!

This first story is about my first time. Started with doing a favor for a cute, "almost" engaged coworker resulting in me seducing her and engaging in a 5-month fuck fest. I'll forever be grateful for our time together where I sharpened my sexual skills under her tutelage.

It was the late 60's, the height of free love and sexual adventure. Well, at least for some, not for me! I was an 18-year-old virgin, finishing my first year of college, without ever having a "real" date. Yes, I attended proms, dances, and even a movie or two with a girl, but it was always a girl that was a friend of a friend or a school chum of one of my sisters. If it wasn't for them, I wouldn't have has any dates. My social development was hindered by 2 events in my life. My parents moved about the same time I finished grade school (8^th grade), leaving my childhood friends (meaning girls) behind, and I attended a private boy's high school. We now lived in a very rural area without any close by girls my age. My school commute was cumbersome, at least two buses, and I was heavily engaged in school activities so didn't socialize much at our new home. My first year of college wasn't much better. My choice of major (engineering) meant that I had virtually zero chance of meeting any girls in classes. I attended a local major university, so I lived at home. I worked part time at a hardware store after school and during the summer between high school and college, so I really didn't have much of a chance to meet girls.

As soon as college classes ended in late April, I quit the hardware store and got a job working at a restaurant as a short order cook. I bought my first car for $75. An old ford that was well cared for without a whole lot of miles. I needed more hours than the 12-20 or so a week I was getting at the hardware store. The restaurant was a local chain with a medium size dining room and car hops. A few of the waitresses and car hops were girls about my age but either had steady boyfriends or were not at all interested in my feeble attempts to charm them into a date.

A couple of weeks after I started working, Karen was hired. Karen was cute, about 5'2" with short strawberry blonde hair, maybe 130#. Although she was a bit chunky, she was shapely and very cute. She did have a little extra, but it was all in the right places with a perfect heart shaped ass and full, 34C, breasts. Unfortunately, Karen had a steady boyfriend. In fact, she described the relationship as "engaged" without a ring - yet. Her boyfriend was a high school dropout that was working construction off and on. He was tall, maybe 6'5", and skinny - leading to his nickname, "Stretch." According to Karen, they planned to marry in a year or so as soon as he secured a steady job.

Karen and I hit it off almost immediately. Maybe the fact that I knew she was totally off-limits made it easier for me to talk to her. During slow times Karen would hang around my grill station. We'd talk about everything; school, parents, the newest records, well - you get the idea. I guess this was the first time since I was in grade school that I had a friend, even casual, that was a girl. Karen was a high school senior, graduating in a few weeks. She had no plans beyond high school other than to work some, get married and have kids. She was an only child, living at home with her parents. She turned 18 in March.

One day in early May, Karen walked with me into the back of the restaurant in a very somber mood. It was obvious that she had been crying. I didn't pry - thought she'd tell me what was wrong if she really wanted me to know. One of the "older" car hops, Debbie, asked her what was wrong.

Karen said, "Stretch's brother-in-law got him a great job on a framing crew for a builder on a major housing development. The only problem is it's in a neighboring state, about 250 miles away. His long work weeks (6 days minimum) and long hours meant that we won't see much of each other over the summer."

I noticed that all the time Karen was talking to Debbie, her mom had sat out in the car outside the door with the engine running. It seemed Karen had a more serious problem and needed to talk to the manager.

She said, "Don, you heard what I said about Stretch. I have a problem getting to and from work. My dad works swing shift, Monday through Friday, from 3:00 - 11:30 and mom works from had a 4:00 pm to midnight. I don't drive yet, so I'm at the mercy of my parents' availability to drop me off and pick me up. With my boyfriend gone I don't have a ride between about 3:30 p.m. and midnight on weekdays. In fact, I'm supposed to work the afternoon shift today, from 11:00 - 7:00 and don't have a ride home. If you can't change my shift, I'll have to quit."

The manager wasn't happy. Although it was a Monday, the weather was nice for the first time in several days and he expected improved business. He was already short of car hops, losing one more would really hurt.

Don asked me, "what time do you get off. I think you live in the same area as Karen, right?"

Although I didn't know it at the time, I drove right past the road Karen lived on during my commute. I responded, "I think so, I'm just starting my shift, working the lunch/dinner shift, 11:00 - 7:30."

"Can you give Karen a ride after work?" He asked.

I looked at Karen and said, "is that OK with you?"

Karen smiling responded, "great, I'll pay you for gas if you can give me a ride when we work the same shift."

After my shift ended, I went to the locker room, took a hot shower, and changed into my "street" clothes. I went out to my car and hung out waiting for Karen. She came out about 10 minutes later, carrying a brown paper bag. She too had changed from her uniform into a short, shirt-style dress.

After we left the parking lot, Karen asked, "are you in a hurry to get home?"

"No," I answered. "I don't have anywhere tonight. What do you have in mind?"

She said, "I really don't want to go straight home to an empty house and wondered if you'd like to go to the lake and feed the ducks." She had bread and bun scraps in the bag she carried.

I said "sure. As I said, I don't have any plans, and with school out, no studying to do."

With Karen providing directions, we headed out on a short drive into the country. When we reached the lake, Karen showed me a dirt road that went through the woods around to the back-side picnic area of the lake. We got out, wandering around talking while throwing bread scraps to the ducks.

As we walked, Karen said, "I don't know how to thank you. If it wasn't for giving me rides, I would have had to quit and I'd never get my license, since I have to pay my share of the insurance." She turned towards me and gave me a quick kiss on the cheek.

I told her, "No problem - it really wasn't out of my way to drop her off and I'd be glad to do so anytime we worked together." We walked back and just sat in the car for a while talking.

After a while, Karen said, "I need to get going, Stretch is supposed to call around 10:00."

I gave Karen a ride twice more that week, on Tuesday and Thursday. Both days we worked the late shift and went straight home. We talked and joked during the drives. Karen remarked that her neighbor asked if she had a new boyfriend and we laughed at that. Secretly I thought, "I wish." Friday night I worked until 7:00; Karen was off. I quickly showered after my shift and walked across the lot to my car. Imagine my surprise when I saw Karen standing by my car.

She said, "we were at the mall, and I decided to come by and see if you were doing anything tonight. My friend is waiting across the lot if I need a ride."

I said, "Dave (Co-worker) and I had talked about going to see the latest Bond double feature at the drive-in, but his dad called and asked him to come right home."

Karen said, "I haven't been to the movies in a long time and really wanted to see the new Bond movie."

With my heart in my mouth, I asked "are you sure that going to the Drive-In with me is going to be ok with Stretch?"

She said, "Stretch knows you're giving me rides from work and he's ok if we hang out together."

I didn't question that statement, after all, this was my first "date" that I managed to get on my own.

I went back in and called my folks, telling them I was going to the Drive-In with a friend to see the Bond movies and wouldn't be home before midnight.

On the ride over, she said, "Don't get the wrong idea, I like being with you, but I have a boyfriend, and this is just two friends going to the Drive-in, not a date."

Well, there went my dream that I finally landed a date on my own. Looking at the bright side, I was at the drive-in with a cute girl, even if she was someone else's girl.

We sat in the front seat watching the first movie. Karen was all the way over on her side of the car. At the intermission, we went to the concession stand, Karen headed to the lady's room, and I bought popcorn and sodas. When we returned to the car, Karen said, "do you have a girlfriend?"

"No," I answered.

"Have you ever had a steady girlfriend?"

I was embarrassed and responded, "not really."

Karen slid over the front seat to sit right beside me. It was an awkward moment for me; I wasn't sure what to do next. I turned to Karen and said, "I really enjoy being with you. You're cute, fun, and bright." She then reached over and kissed me, this time a kiss on the lips. I may have been slow, but I wasn't stupid. I put my arms around her and kissed her back. After a few minutes of kissing, She scooted over and sat on my lap. As we kissed, my hands wandered over her back and sides, then to her hips. She stiffened somewhat as I slipped my hands around her ass and gently messaged her ass cheeks. After a while, I moved my right hand off her ass and moved it to her legs. I slowly slid up to her thighs, moving my hand under her short dress, between her legs. At that point, Karen sat up straight, moving my hand from under her dress.

She said, "Remember, I have a boyfriend. I think we just need to watch the movie."

Karen stayed on my lap as we watched the second film. We frequently kissed and my hands wandered over her body, paying particular attention to her hips and thighs. Any attempt to move my hand under her dress was met with her gently pushing my hand away. The movie ended and Karen shifted back over off my lap.

She said, "I really enjoyed being with you, but I need to get home, my folks will be home. I didn't have a chance to tell them we were going to the Drive-In."

The next time we worked together was Monday. I worked until 7:30, Karen worked until 8:00. I showered and changed and waited for Karen. Again, she carried a bag of bread scraps - to feed the ducks - and off we went to the lake. The parking lot was empty. We got out of the car and walked for a few minutes; pausing every couple of feet to kiss. Karen quickly fed the ducks and headed back to the car. Karen mentioned we'd be more comfortable in the back seat - no steering wheel in the way. I slid in first, Karen climbed onto my lap. Karen seemed to be the aggressor, thrusting her tongue into my mouth while we kissed. My hands went back to their wandering, moving up Karen's legs to her thighs. This time she didn't stop me, and I moved my hand all the way to her panty covered pussy. Karen kept her legs tight together, so the best I could do was stroke her outer lips of her cunt with the tips of my fingers. With my left hand, I carefully undid one button at a time on her shirt dress, eventually pulling it open. I then moved my left hand to her breast, slowly messaging it through her bra. After a few minutes, I attempted to reach behind her to unfasten her bra, but she moved my hand away and we continued to kiss. I then managed to get my left hand below the cup of her bra and slowly slid it up uncovering that beautiful tit. Both hands were now busy as I continued to stroke her thighs with my right while kneading her breast with my left. My tongue wandered from her soft mouth down to her uncovered tit. As I tongued the nipple, Karen gave out a low moan and held my head to her.

Suddenly, Karen sat straight up; I thought that was the end my fun. Instead, she surprised me, slipping her dress and bra all the way off, playfully saying "You tricked pushing my bra up. I'm uncovered anyway and don't want to get my dress wrinkled. You behave, hear?"

As she settled back onto my lap, she was nearly nude with only a pair of cotton panties on. We returned to kissing; however, Karen kept her thighs locked together, preventing me from sliding her panties off or getting a finger into her cunt.

After we settled back into our routine, Karen's kisses took on a new urgency. I decided to try a different tact, and I slowly pushed her backwards onto a prone position while still under her. After she was lying down, I slipped out from under her. Before she could object, I pulled her panties down her thighs and off her. There she was in front of me, nude, legs splayed out exposing her cunt to my hands and eyes. I immediately began to play with her cunt with my right hand. Although I had zero experience prior to this, I guess Mother Nature gave me an assist. I slowly played with her clit, rubbing it with my fingers. After a few minutes of this, I inserted one, then two fingers into her cunt while using my thumb to continue to play with her clit. I figured I must have been doing something right, as Karen's moans increased in intensity as I played with her. Karen suddenly stiffened and I felt the warm moisture flow from her cunt. I thought she might have cum, but with my lack of experience, I wasn't sure. My heart was beating a mile a minute. I was finally going to get laid!

This was the moment of truth. I moved away and quickly removed my pants, shirt, and underwear. I reached over the front seat and secured a pack of rubbers from the glove compartment. As I fumbled with the foil wrap and attempted to slide the rubber on, Karen started to sit up.

"We need to slow down. You tricked me once again pushing me back on the seat and got me hot and bothered by playing with my pussy. I'm sorry I let things get this far and I can't do this. The only previous time I've gone this far was with Stretch. I was baby-sitting for his sister; he came over and we ended up having sex. We agreed that they would not let it happen again until we get married. I can't cheat on Stretch."

I figured that if I wasn't careful, I'd screw up any chance of getting Karen then, or maybe ever. My first thought was to try to make her feel bad. Call her a tease, mention blue balls, all those adolescent tricks boys try on a girl when she says no.

Putting my arm around her, I said, "I understand, we won't do anything you don't want to do."

We sat there, side by side, just holding each other. When she didn't make any moves to break away or try to put any of her clothes back on, I figured I was still in the game. While we talked, I slowly stroked her bare arms and legs. I gently kissed her cheek then nuzzled her neck. After a few minutes, I moved in front of her and began to kiss her. It was a tight fit there in the back seat trying to maneuver into a comfortable position. Fortunately, the older cars have a roomy back seat and - as I mentioned - I'm short and skinny.

At first, she kissed back but kept her lips tight together. I also continued to stroke her arms and legs slowly. She seemed to relax and allowed my tongue to invade her mouth. I moved my hand first down to her breast then to her legs, eventually back to her pussy. While sitting in front of me, she spread her legs, letting me get two fingers back into her.

"Oh, that feels so good, and it's been a long time," she said. After a few minutes she closed her eyes and slid down onto her back on the seat. I figured this was my chance, so I rolled the rubber down on my cock. I moved over her, rubbing her body slowly. She then spread her legs apart and reached up for me. My heart was in my mouth as I moved into position over her. I made a couple of stabs trying to get into her, missing. Karen reached between us and inserted my dick in her.

The moment was intense! She felt so hot and tight, I thought I'd blow my load immediately. I slowly fucked her, trying so hard not to cum quickly. It was no use. The extensive foreplay and the fact that it was my first time doomed any chance I had to hold out long. I thought my head would come off as I blew my load into the rubber. I must have had a dozen spurts. I totally filled the rubber. Then I remembered Karen.

"I'm sorry for cumming so fast," I said.

Laughingly, she said, "I understand. The first time Stretch and I made love, he came immediately after entering me. It was a whole lot better the second time."

So here I was, in the backseat of my car, just made love a girl who was engaged to be engaged. I felt kind of smug, but knew I wanted more. I peeled off the rubber, used tissue to clean up and tossed it all in the bag that Karen had brought for the bread. I then settled back next to Karen, gently holding her while kissing her. She snuggled back against me; saying I was very loving and sweet. I again lowered her on her back on the seat and moved my head between her thighs. I slowly reached out with my tongue and flicked her clit. This was a first for me, and, as I found out later, a first for Karen. I wanted to give her as much pleasure as she had given me a few minutes ago. My tongue explored her cunt, delving into the folds and back to her clit. I moved my right hand down to her cunt, using it along with my tongue to play with her clit. I don't think I would have done this if I hadn't worn a rubber when we fucked. I kept this up until she came again. I think I enjoyed eating her at least as much as she did. After she came, she pulled me up along her body until she could kiss me.

My dick was hard again, but I didn't have a second rubber. "Sorry, I don't have another rubber," I said.

"That's' OK, it's not my fertile time and I'd like to do more," she said.

I entered her a lot easier this time. The sensation was even better than the first time - nothing between my dick and the soft lining of her cunt. I stroked slowly in and out. She raised her legs up pulling me in even deeper. While fucking her, I reached out and gently palmed her right breast. She seemed to like that, increasing her moaning. I felt her stiffening - and paused so she could relax after her climax. I then increased the speed and depth of my thrusts and flicked my tongue over one nipple than the other. Now things were really heating up. My thrusts were hard and rapid. Karen seemed to be going crazy, rolling her head side to side, and matching my thrusts with her own pelvic thrusts. I think Karen came again.