Cheryl

Just as I always do, I sat down at my desk after dinner and logged on to my personal e-mail account. I had been separated from my wife now for about 6 months, and the divorce was taking forever to get done. And, after living on my own for a couple of months, I had decided to start dating again. So, I was on three different on line dating sites, two that were "vanilla" and one that was very much adult oriented. My nightly routine was to see if I had any e-mail from someone on the sites, then go to them and see if there was anyone new or interesting that I would want to meet.

Tonight there was an e-mail from the adult site, something that I had found to be a rare occurrence indeed. It was an e-mail from a woman, and all it said was "I know who you are, and I will be in town next week for a conference. Let's get together."

Of course, I was intrigued. I had posted a couple of my pictures on the site. And, unlike many there, I showed my face, as well as a nude photograph. So it was very believable that someone really did know me. There was only one way to find out. I logged on to the sight and looked up the person who had contacted me.

The profile wasn't particularly helpful. There was a picture of a woman with her back turned to the camera. She had long brown hair, and was in a bikini which revealed nice legs and a firm butt. That was the only picture, no face. The profile indicated she was in her 40's. She lived in eastern Ohio and was looking for a long term relationship. Not exactly the type of profile I would be drawn to, since my goals, at least on that site, were far more focused on getting laid.

But she said she knew me. I had been born and raised near where she was now living, and had gone to college in Ohio. Maybe she really did know me. And besides, she did have nice legs and a cute butt. So I e-mailed her back. It was a short e-mail, along the lines of "Hi, thanks for writing, how do you know me?"

Within a half hour, I had a reply. She told me she knew my name (and she got it right), she had known me for a long time, and that she and I had had teenage sex. And she described the house where I grew up to a T. So, she did know me.

I went through the girls that I had had sex with in my hometown during high school. I was a relatively late bloomer, and had really only dated three or four girls throughout high school. And back then (the late 1960's) girls didn't just have sex with the guy they were dating. There was no pill, and we were all taught to save it for marriage. But that didn't stop us from fooling around. Heck, we started out (at least the guys did) jerking off in front of our pals, and as we got older, we would date and make out with our girl friends in the drive in. I still remember the first time I touched a girl's nipple with my fingers and the first time I put my hand under her mini skirt and touched her panty clad pussy. So this has to be easy. I mean, there were only so many girls I had had sex with as an 18 year old. In fact, I knew there were only two.

First there was Laverne. We had been each other's first dates, starting in 8th grade. And we went out off and on for the next 4 years. We had sex in the back of my family's station wagon the summer after graduation while at the drive in. Heck, I even remember the movie, Jesus Christ Superstar. But this couldn't be who had written to me. Laverne was blonde. And she wasn't as tall as this girl, at least according to her picture. But it was sure fun remembering that night, when we went all the way. I still remember how easy it had been to convince her that we go into the back and put the seat down. How we kissed, with our tongues intertwined, while I groped her breast through her cotton shirt. I remember how surprised I was that she wasn't wearing a bra, although thinking back, it was the era of "burning your bra". As I sat there, I could almost feel how her nipple hardened under my touch, and how she pushed me down on the car floor and straddled me while I struggled to unbutton her top and finally get to see those wonderful titties. Her nipples were very lightly colored, almost pink, and they were hard and erect. She began grinding down on my hard cock, straining through my jeans, and I ran my hands down her chest, across her flat tummy, and then began to undo the buttons on her shorts. I must have been too slow, because Laverne pushed them away, yanked off her blouse, and undid her shorts while sitting up on her knees so she could begin to slip them off. I unbuttoned my shirt as I stared at her wondrous boobs, then I crushed her to my face and began licking and sucking those nipples for all I was worth. She kept trying to undo my belt, and finally pushed me away so she could finish and unzip me. She yanked down those jeans, and my hardness was outlined in my white underwear (remember, this was in 1969). She moved her head down and kissed my throbbing cock through the cotton. And my hand was moving inside her pussy, moving fast and hard. Hell, I was 18. What did I know about taking it slow and making her feel good. And she didn't seem to mind. She pulled off my underwear, and immediately positioned herself so that I could enter her cowboy style. She slowly lowered herself onto me, and that was the first time I had ever been inside a warm, moist pussy. And, I am embarrassed to say, I came in less than 30 seconds. We hurriedly cleaned up and redressed. The drive in is still fairly public. And back then, neither of us knew how wonderful long slow lovemaking could be or really how to please each other fully.

But it wasn't Laverne. Ok, was it Marilyn? Marilyn had been going out with my best friend in high school. But they broke up after graduation and before we all went off to college. We had hooked up the summer between freshman and sophomore years in college, and it had been pretty torrid for those two months. I still remember me coming to her house one night after work at my summer job. Her parents weren't home, and she met me at the door wearing only her panties. Instead of using her single bed, we retired to her parent's room and used their queen size. Once again, it was rushed. I stripped, she lay down, I pulled off her panties, and was instantly inside her. We moved together fast and furious, hoping to finish before her parents came home. I was fascinated watching her tits juggle as I thrust into her. And once again, my orgasm took precedence. We couldn't have been in her parent's bed more than 15 minutes.

But Marilyn had black hair. So it wasn't her. Who the heck was this?

Then another e-mail came in. My mystery woman was sending me instructions! She was going to be at a convention in the town where I worked beginning on Saturday (it was only 4 days away). She was staying at the Hyatt downtown on the waterfront. They have a wonderful bar there on the 40th floor overlooking the harbor and the ocean. We were to meet there Saturday night at 8. She said she would know me, since after all she had a picture from the site, and not to worry she would find me there.

I was torn. This woman had contacted me from an adult "dating" web site where people post profiles to meet sex partners. She had proved that she knew me. She said we had had teenage sex. Her picture (if that was her) was cute. And maybe it was Laverne or Marilyn using a false picture, either of whom I would love to see and maybe end up in bed with. And the Hyatt bar was one of the best spots in town to pick up women, especially professional women near my age attending conventions or conferences. So, I agreed to meet her there, and to make sure she would know me described the blue blazer, chinos, and deck shoes I would wear.

Then I hear nothing from her at all for the rest of the week. As the week went by, I kept running through my head who this woman might be. I thought maybe someone from college, but I had never brought a girl home so she couldn't have described the house. And she said teenage sex...I really didn't get my sex life in gear until in my 20's at college. As I said, I was a slow beginner. But I knew I wanted to find out who she was and have the mystery solved.

Saturday came, and I got ready, dressing just as I said I would. I got there about 7:30, since I knew that the place filled up on weekend evenings. I took a table along one of the huge glass windows from which you could see the ocean and the two islands just south of the bay entrance. I could also see the bar entryway, and began looking for someone I might recognize. I have to admit, I love doing this, watching beautiful women dressed to impress at a high class bar. Too bad, I mused, this didn't exist when I was in my 30's or 40's. This is where I would have been. But I was married then. Now, I'm single, successful, but in my early 50's. Still, I have been known to meet some pretty good people here, and not just sex partners. My mind wondered off, running through some of the people I had met here, ending up focused on the couple from Texas that I had met last year. We had had a great time talking and drinking wine, then me dancing with his wife. We'd finally decided that there was great chemistry, and they invited me to their room. It was not exactly what I had expected, really much better. They were in their early 40's. Obviously they took pride in how they looked...not gym rats, but people who kept in good shape physically and mentally. She wore a cute black dress, low cut with spaghetti straps, and heels. He was in a casual pants and a golf shirt. We had talked about the great meal they had had and the good restaurants in town, going to wineries, golfing, and vacations. And we had been exchanging sexual innuendos since the second drink, when I complimented her on her dress.

Once we got to their room, I knew that the night was going to be a little different then I had first believed. We entered the room, and almost immediately both of my partners turned towards me. She moved closer and kissed me deeply, while he dropped to his knees and began to unzip me. As I kissed her I moved my hands over her wonderful breasts, pushing on them firmly and feeling them react to both my hands and our kiss. I was reacting as well, and my hard on was getting larger, when I felt him put his mouth over it and begin sucking me. Now, who am I to get all moral about this? I mean, I am here with his wife, kissing her and feeling her, so why should I care if he wants to put me in his mouth, especially when it felt so good.

His wife slowly moved towards the bed, leading me there with her mouth. My hands were fumbling for the zipper on the back of her dress, drawing it down finally and revealing that she wore no bra or panties. One of my hands dropped to the small of her back and I began to massage the top of her wonderful ass. The other hand continued playing with her now released breast, manipulating a nipple between my thumb and forefinger. We were standing next to the bed, and hubby was still on his knees, slurping on my cock, while he undid his pants with one hand and massaged my cock with the other.

I stepped out of my pants, and her dress fell to the floor. I pushed her back onto the bed, following her down. Hubby released me and finished taking off his pants and shirt. Soon all three of us were naked on the king sized bed. I had my mouth on her nipples, suckling them and flicking them with my tongue. She had grasped my cock and was stroking it firmly, up and down. Her husband was now between her legs, licking her moist pussy for all he was worth. I grabbed his cock in my hand and began matching her stroke for stroke.

We stayed this way for a bit, then it became obvious that she wanted more than a mouth on her pussy. Because she got up, pushed me onto my back, and then straddled my cock, lowering herself onto it slowly, with her face looking towards mine. Her husband got up and stood at the side of the bed, where she could take his cock into her mouth. And my hands went right back to her lovely breasts, massaging them, crushing them, and twirling the nipples as she rode me.

Pretty soon she began to moan, a deep long moan from the depths of her soul. Because, as she rode me, I was both twisting and rising towards her, so that as she thrust down, I thrust upwards with the twist causing my cockhead to rub against her g-spot. She was getting more and more excited and really clamped down on me. Her husband was also getting really hot, as he thrust into his wife's mouth. I knew I was getting close. All of a sudden, her husband started shaking and I knew he was cumming. She was doing her best to swallow it, but with her moving up and down on me, there was no way that some of his hot cum was going to miss her mouth, getting into her hair and on her face. The sight of her disheveled hair and the white glossy liquid dripping down her face caused me to start to cum as well. And, now that her mouth was free, she screamed as a deep orgasm filled her body. We both seemed to jerk and spasm for minutes before she collapsed and rolled off of me.

Her husband immediately put his face into her pussy and began to lick my cum out of her. I turned towards her and moved to kiss her lips, licking up his sperm from her face and allowing her to taste it from my mouth.

Yea, that had been a great night, and the fact that there was some bi action between her husband and I made it all the more special.

But, as I got lost in the memories of that night, I stopped watching the entry way. And so, I was very surprised when I heard someone call my name out. I looked around, and there was my cousin Cheryl standing there. Now, Cheryl is about 6 or 7 years younger than I, and had sort of hung around me as I was growing up. It had been around 25 years since I last saw her. I had moved away from my home town after college, doing a long stint in the military. She had moved away right after her high school graduation, and I had heard she had gone to night school and gotten both her bachelor's and master's degrees the hard way. And all of a sudden, it hit me. This was my mystery woman. Cheryl is in her mid forties now. But the last time I saw her, she was 18 and just out of high school, and I was home on leave. What had thrown me off was her mention of teenage sex. Here I thought it was me as the teenager, when it turned out that it was her, just turning 18 that summer I was home.

We had both been pretty bored when I was there. After all, this was a very small town, and I had been living in California for 4 years and had been overseas twice. And Cheryl was never going to be able to stay in the hometown. She had always been a rebel, even when she was 10 or 12. So, when I suggested to her at her graduation party that we should maybe hang out a bit while I was there, she had eagerly accepted. I will admit I found her attractive. She was 18, had truly filled out well, and her long brown hair framed her pretty face and dropped over her breasts. But, she was my cousin, so she was off limits as far as sex was concerned. Well, at least I thought so at the beginning.

We made arrangements to meet the next Saturday. It was the next to last day for me to be home, and I had told my parents that I wanted to go out with a couple of high school friends. But Cheryl and I were going to meet at the local tavern, have a few beers, and (she said) meet a couple of her girl friends. And, after a week at home, I was ready to get out of the house and have some fun. Maybe even get lucky.

I drove over to the tavern and walked in. it was dark, noisy, and filled with guys drinking the local brews, with about half as many girls with their dates or milling around the pool tables. I saw Cheryl over by the juke box and my mouth dropped. There she was in about the shortest skirt I had ever seen (this is 1975 now) and was wearing a sheer yellow cotton top, tied at the waist, very deeply cut, and clearly showing her nipples. I stared for quite a bit, then walked over, adjusting my growing hard on as I did. She looked up and smiled, handed me a beer, and we proceeded to talk about what a great place the hometown was to grow up, and then leave. After a few minutes, with me trying very hard not to stare at her nipples so clearly outlined under that cotton, I asked her where her friends were. She told me that she had never intended to ask them out because she wanted me to herself. I was floored, embarrassed (this is my cousin after all), and a bit confused. But she told me that she was tired of small town guys with small town ideas, and that I was the first breath of fresh air and sophistication she had seen. And she wanted to spend the night with me, talking about how it felt to get out of, what she termed nowhere.

We went to a table and talked for about an hour. I have to admit, I kept staring at her tits. And, even though I was distracted, I discovered that she was a lot more savvy, smart, and ambitious then the 12 year old that I had remembered her as. After a bit though, I wanted to leave. The place was loud, it was a local beer hall where the topics were how the high school football team would do next year and what the local professional baseball team was doing. So, I suggested we go. And she agreed.

We went out and got into my rental, then drove away. I was thinking of a more intimate bar, maybe. And then I got this idea. I headed south, towards the only big city nearby. As we drove, we talked more, and we started flirting. It started when she said she knew where my eyes had been all night. I asked her if she was embarrassed by my staring, and she said no, that she had actually liked it. From that moment on, I knew where I was taking her.

After about 30 minutes, we were downtown, driving along the river. She had asked me who my high school lovers were, and since she knew both of them, she commented on whether I was lucky that we split before college. She wanted to know about college, and what went on there, especially sex wise. She whined a bit because she couldn't afford to go to college right away, but she was going to get a job and save money to go. But she loved the stories about beer drinking frat parties, streaking, and how loose everyone seemed to be, or as she said, how sophisticated they were.

When I turned into the parking lot of the Hyatt downtown, she got quiet for a second. I told her I was going to go get a room (after all, I was 24 and a military officer) and that I would then take her to that room. We were going to make love, not fuck. And we'd also talk. We were going to stay there all night, and she could call her mom (my aunt) and tell her she was staying at her friend's. I then told her she had a choice. She could do this with me, or I would drive her home. She leaned over and kissed me. Our tongues swirled together, and I pulled her head closer to me. But there was no urgent grasping or frenzied adolescent groping. I had learned a bit in 6 years.

I went in and registered, then returned to the car and drove it into the garage. We went up the elevator to our floor, and directly to the room. It overlooked the river and downtown, with a king sized bed. Cheryl sat down and I sat next to her. I kissed her, and then told her to call her mom.

As she told her mom what she was supposedly doing, I caressed her hair and slowly let my hands drop down her side. I brushed the swell of her breasts and then continued down to her hips. She squirmed a bit as I brushed the inside of her thighs with the back of my hand. After she hung up, she moved into my arms, and we went back to kissing. My hands were now on her breasts, but I was slowly massaging them, twirling the nipples a bit, and using the backs of my hands to brush the firm skin. I untied her blouse, and then slowly moved it over her shoulders. She was naked now above the waist. I move my head down and licked the sides of her breasts, then underneath them. I pushed them together and moved my tongue across the inside of each one. I blew on the nipples, and then slowly engulfed one with my mouth. I sucked in, tweaking her nipple with my tongue. And she gasped and held my head right to her breasts.