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Back in the early 1960’s when I was a young teenager my father bought us a pool table. Soon I was spending every minute that I could playing pool. It was different in those days. We didn’t have computers, cell phones, or any electronic games to play. What we did have was a deck of cards, a Monopoly game, and three channels on our small black and white television. I listened to the radio a lot back in those days. Amazingly I could easily pick up WABC out of New York City, WBZ in Boston, and WOWO in Fort Wayne, Indiana. I listened mostly to Cousin Brucie back in those days but now I wished that I had listened to Wolfman Jack more. I also went to the Movie Theater often because I could get in for a quarter.
I loved Creature From The Black Lagoon, Black Scorpion, and just about anything science fiction. I loved the westerns on television too. Then in early January 1962 I saw ‘Twist Around the Clock’ with Chubby Checker performing his latest hit ‘The Peppermint Twist’ from his nightclub called The Peppermint Lounge in New York City. The girls in the audience were dancing in the aisles of the theater and I got up to join them. That’s when my life changed…for the better. I went from a nerd to cool dude in just a matter of seconds, even though it took me another twenty-two years to realize that I was a nerd…thanks to the movie ‘Revenge of the Nerds’ in 1984.
I found that listening to Rock and Roll music and shacking my hips to the beat actually improved my pool skills. I watched Minnesota Fats on television and would practice his tricks until I could do almost all of them.
By the time I turned fifteen years old I was the best pool player in my town. I didn’t hustle if that’s what you were thinking but I never had to pay for a game either. There would be quarters lined up on the edge of the pool table from guys just waiting to play me and loose. The pool halls were full of guys that thought that they were better than I was. I proved them wrong every time but a few of them actually gave me a run for my money.
My kid sister Josephine turned fourteen just two days after my fifteenth birthday. Over the previous year she had grown up rather nicely. She wore a bra most of the time because mom wouldn’t quit bitching at her until she did, but she never did wear a panty girdle. However, Josephine did wear a garter belt to hold up her stockings. We didn’t have pantyhose back then either and seem less nylons were more expensive. Josephine always asked me to make sure that the seam in the back was straight for her. That required my kneeling on the floor behind her and her lifting her dress up above her knees. On rear occasions I got a quick look at her panties. In those days they were all white and mostly cotton, just like my Jockey shorts.
I had been so interested in practicing pool over the last year that I hadn’t even noticed that my kid sister had grown up. She didn’t look like Claudette Ann Radison but she sure was getting pretty.
Josephine knew that I was in love with Claudette Ann Radison. She called her ‘CAR’ for short. Then one day Josephine asked me to teach her how to play pool. I shrugged her off but she wouldn’t take no for an answer. Finally out of desperation she said that she would just play in her panties if I would teach her. Just her panties! Oh my God! Of course I said yes to that. I had never seen a pair of boobs before in my life. Dad had a few issues of Playboy but he kept them hidden from me.
The best time to teach Josephine how to play pool in her panties was right after school for an hour or so. Dad was not home from work at that time and mom was preparing supper, so it was perfect. Josephine would go up to her bedroom and change into a loose fitting dress, removing her bra, and then she would come down into the basement with me.
I still remember that first time that Josephine slowly lifted her dress up over her head as she removed it revealing her bare breasts to me. I was simply amazed. They were nicely shaped and had sweet little pink caps on them with tiny hard nipples centered perfectly. When I asked her if I could touch them she said maybe, but first I had to teach her how to play pool. She was not too bad at it but I gave her some pointers to help her out. All she really needed was a few hundred hours of practice like I had put in. Meanwhile I had a constant erection from watching Josephine bend over and her big white panties stretched tightly across her firm ass. I watched her as she held the cue stick in both of her hands and slipped it between her bare hanging breasts to hit the cue ball. It was almost hypnotic. When a fast song came on the radio Josephine would twitch her hips like I did, but with her wearing just her white cotton panties I could see every one of her muscles twitch in beat to the drum. Then ‘Wipe Out’ came on. Josephine stood up, put her cue stick down, and faced me as we danced together. I stared at her nipples as they stood out hard and proud and jiggled around like they were going to fall off or something. Just as soon as ‘Wipe Out’ finished ‘The Peppermint Twist’ came on. Josephine and I had danced to that one before but when we were fully dressed. This time when we went down low I saw that the crotch of her panties were moist and not from sweat because our basement never got that warm. The moisture dampened the material enough so as to become partially transparent allowing me to see her dark patch of pubic hair. Everyone in our family had dark brown hair and brown eyes.
All too soon the song ended and she went back to practicing. Before dad got home mom hollered down for us to get cleaned up for supper. Josephine told me that I had done a good job instructing her and that I deserved a reward. She said that I could feel of her breasts for a whole minute and then she stood before me. I reached out and touched my first boob. I don’t know if a whole minute went by or not because I was suspended in time with my sister’s breasts in my hands. Finally the spell was broken when Josephine stepped back and slipped her dress down over her head. She asked me if we could do that again the next day. I laughingly told her that learning to play pool was very difficult and that it could take years. Josephine smiled and simply said, “Okay.”
After about a week of teaching my sister to play pool in just her panties Josephine asked me if I wanted to see Claudette’s tits. Oh hell yes! Claudette was a goddess in my eyes. Every boy in school dreamed about Claudette when they jerked off at night. On a scale of one to ten she was a twelve without question. Claudette was even prettier than Annette Funicello from the Mickey Mouse Club was. I had been in love with Claudette since the third grade, even before she got her tits. Her tiny waist and her big boobs gave her that hourglass figure like Elizabeth Taylor and Marilyn Monroe.
Josephine told me that she had been talking to CAT at school about learning to play pool. CAT is CAR’s younger sister. CAT is short for Cathleen Ann Turner. She is Claudette Ann Radison’s younger sister. Their mother has had a few husbands over the years. They have two more sisters that are called CAB and CAN otherwise known as Cassandra Ann Bennett and Cynthia Ann Norton. Currently their mother is looking for husband number five. It seems that husband number four stuck around a lot longer than any of the others had. None of her other marriages lasted more than a year.
Anyway Josephine said that she could get CAT to come over for pool lessons and then that CAT could get Claudette to come over too. Really? It seemed to far fetched to work but Josephine said that it would work out just fine. So I said, “Okay!”
That afternoon Josephine and I played pool until another Chubby Checker song came on the radio called ‘Limbo Rock.’ I held the pool stick while Josephine danced underneath it a few times. She was really good at it too. I had seen her and her girlfriends do it quite often but never just in her panties before. I knew that my sister could dance under a stick that was just twelve inches off the floor. I watched as she spread her legs and her moist panties stretched across her pussy. After her belly got under the stick she lifted her knees up and slipped her breasts underneath it. Then as her head came under the bar her pussy mound was up high in the air and I reached out and grabbed it with my hand. Josephine simply finished getting through the obstacle and then stood up. I thought that she would be mad at me but she wasn’t. What she wanted was to feel my cock since I had felt her pussy. Fair enough but then she insisted that I had to drop my pants to my ankles and let her feel my cock through my underwear like I had her pussy. Okay! So she felt my rock hard cock until I cum in my underwear. It didn’t really take much at all because I had been so excited. I was embarrassed about it but Josephine thought that it was cute and told me that she has an orgasm every time that we have a pool lesson. Really? Girls cum too? Oh yes and even more often that we boys do too. She told me that was why her panties were always damp around me. She said that she wanted me to teach her how to play pool in just my underwear after that. Okay!
Well a couple of days later Josephine brought Cathleen home for her first pool lesson. This time they just came straight downstairs to me. Normally Josephine had changed up in her bedroom and come down a little more prepared. However in the last two weeks nothing had happened and mom was not suspicious of anything. So the two girls came down in their school clothes. Josephine was not the least bit shy about getting undressed in front of me any more, however Cathleen was. So I undressed too and then together we stood there in our underwear waiting for Cathleen to undress. At fourteen she was almost as pretty as her fifteen-year-old sister was. Cathleen eventually undressed down to her panties too. Her breasts were a little smaller than Josephine’s breasts were but her nipples and areola were much darker in color as was her skin tone. Her father had some Mediterranean blood that gave Cathleen a darker complexion. Cool! All I knew was that Cathleen had the second set of breasts that I had ever looked at. We played pool but we stopped to dance every time that a nice fast song came on. At the end of our lesson time a nice slow song came on and Josephine told Cathleen to dance with me. I held her naked breasts to my bare chest as we swayed to the music. My hands drifted down to her fine ass. My cock started to grow pretty good at that point but Cathleen didn’t say anything. After the song ended and we parted Cathleen just looked at my crotch. My cock had formed a pretty good tent in my underwear. Josephine came over and held it for a while and then told Cathleen too hold it too. While she did, I held my hand to her crotch cupping her nice warm mound like I had my sister’s mound. We held that position for a while and then I felt of her breasts as my sister told Cathleen to stroke my cock until I cum. She was simply amazed and very excited to jerk me off. What really surprised me was when she reached into my underwear to hold onto it. Cathleen was the first girl to ever touch my cock like that. To be fair I slipped my hand down into Cathleen’s panties brushing her pubic hair with the palm of my hand. Josephine started giving me lessons on how to masturbate a girl. Soon I was poking my finger up into Cathleen’s wet vagina and rubbing her little clitoris briskly. Shortly we came together in the greatest orgasms of our life. It was absolutely fantastic.
Cathleen decided that she did not want to share me with her older sister just yet, so for a full week she got my undivided attention and even my sister stayed out of it during our lessons. However at bedtime Josephine made sure to get her hand on my cock and my hand in her panties. We really enjoyed jerking each other off before going to sleep. I know that I had almost stopped jerking off after that.
That week flew by but I sure got to feel Cathleen up a lot. In fact the last two days we all took off our underwear too and played around in the nude. I got very good at pressing my chest into Cathleen’s back while I cupped one of her breasts and fingered her clit at the same time. Meanwhile Cathleen would reach between her legs and stroke my cock until I shot gobs of cum onto the basement floor. Then she would lick her hand clean afterwards.
Finally Claudette joined us for lessons in playing pool. Her sister Cathleen had briefed her as to what to expect. Claudette tried not to act too shy as we all undressed in our basement to begin our pool lessons. As we had done the last couple of times we stripped completely naked. Only we never did play pool that first day. Claudette and I made out for the whole hour with our sisters encouraging us to go further and further. I sucked my first nipple and I licked my first pussy that day. Claudette felt her first cock in her hand and in her mouth. She even swallowed a load of cum before she even realized it and the best part was that she liked the taste of my cum. She brought me off three times in that hour, twice with her hand, and I gave her seven orgasms with my finger. She said that I had made her clit very tender. We kissed and we slow danced. It was wonderful. Claudette was my dream girl no more…she was my girlfriend.
The next day our sisters encouraged us to go to the final step. Claudette said that she wanted it too so I slipped my cock into her virgin pussy while our sisters cheered us on. I lifted her up onto the edge of the pool table and she opened up her legs for me. I scored on the first plunge. It was the best feeling ever for me but Claudette said that it had hurt her just a little bit. The longer I fucked her the more she liked it. Then I filled her pussy with my sperm. I fucked her twice that day and we both enjoyed it a lot. She came with me that second time. The second day was just about the same with Claudette and I kissing, feeling, and fucking all the time while our sisters practiced playing pool. On the third day though she wouldn’t take her panties off and she had a big pad in them. That day I learned about periods and Claudette even let me get down and look inside her panties at the bloodstain on the pad. The forth day though Claudette showed my sister and I a tampon for the very first time. I even saw the string hanging out of her pussy.
Claudette’s mother had asked her if she had had sex yet and she had answered yes. Her mother showed her how to insert the tampon and then gave her the birds and bees talk. Now it wasn’t at all what my mother was going to tell my sister in a few years…that’s for sure. She told Claudette that sex was fun and very enjoyable but that she should have me use a rubber for a little while. She even gave Claudette a box of rubbers for me to use. She was also going to get Claudette on something called a birth control pill. Apparently it had been on the market for almost two years my then. Claudette’s mother didn’t mind that she was having sex but she didn’t want to be a grandmother yet. I was also invited over to her house anytime that I wanted to have sex in Claudette’s bedroom. She shared her bedroom with Cathleen but that was alright too after she had the full story about our pool lessons.
That Saturday Josephine and I were invited over for the day. Claudette’s mother was very pretty. She sat us down with her four daughters and explained everything that we ever wanted to know about sex and then some. She told us stuff that we already knew but that was more for the younger girl’s benefit. We learned about masturbation, oral sex, anal sex, and various sexual positions.
I was shocked when Claudette and I were asked to demonstrate some of the techniques for her younger sisters. But first Claudette’s mother made sure that the doors were locked and that the drapes were closed. Then she had all of us undress, including herself. We were all encouraged to fell up the other six people. I was in heaven. Mrs. Norton as she was still called was a real fully-grown woman. Her breasts were full and heavy, her nipples were big and suckable, and her pussy was puffy and very wet. Her daughter Cassandra was thirteen years old and her youngest daughter Cynthia was twelve years old. They both had nice little breasts and small pussies with sparse hair on them. Of course I came not too long after getting jerked off by Mrs. Norton. She caught my cum in her hand and then offered a taste to her daughters. Claudette and Cathleen had already tasted it first hand so Cassandra and Cynthia got most of it with Mrs. Norton cleaning up the rest.
After Claudette and I had demonstrated sex with her on her back and me on top of her Mrs. Norton suggested that I demonstrate the doggy position on my own sister. Josephine and I had not had sex at that point but she was very willing to let me. I looked at Claudette and she nodded for me to continue. After all she was my girlfriend now. So I slipped my cock into my sister’s virgin pussy from behind while she was on her hands and knees. It was just as good as the first time that I had fucked Claudette only it was my own sister and it felt even better knowing that. After slamming my cock into her pussy for a while I came deep in her. Next I was told to get on my back and then she had Cassandra get on top of me and mount me. All the while that I was fucking her thirteen-year-old daughter Mrs. Norton was telling the girls how great that position was for self enjoyment, beginners, and to satisfy a boy with a really big cock. That way she was in control and he couldn’t hurt her too much. After that Cynthia sucked my cock for a little while and then she too got on top of me for her first fuck. That day my sister and all three of Claudette’s sisters lost their virginity to me.
As a final demonstration I got to butt fuck Mrs. Norton in front of her four daughters and my sister. She put some lubricant in her butt hole, on my cock, and then she got on her hands and knees. I just watched as her big tits hung low and swayed ever so nicely. I knelt behind her as five pair of eyes watched my cock enter her puckered asshole. Her butt was almost as tight as Cassandra and Cynthia’s virgin pussies had been but it was so well lubricated that there was very little feeling. I had cum twice already in my sister and in Cynthia but I really wanted to cum again in Mrs. Norton. After a very long period of time Mrs. Norton had an orgasm. That’s when she clinched her butt cheeks tight and I got much more feeling. I picked up my pace and soon filled her rectum with my hot sperm.
Then Mrs. Norton demonstrated a lesbian sixty-nine to us using Claudette. After the demonstration she had the other four girls pair up and try it too. Then every girl had to try it with all of the other girls and with me. Sixty-nine soon became my favorite number.
Since then Claudette and I made love often and stayed together all through high school and college, then we got married…in 1969. I told you that sixty-nine was my favorite number.
I have been submitting stories for a full year now. I hope everyone has found a few that they liked.
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