My first older woman taught me just about everything that I knew about sex and allowed me to please every woman in my life after her…especially my wife.
Fbailey story number 380
My First Older Woman
I was sixteen years old at the time and I lived right next door to two wonderful women. The first one was an adorable thirteen-year-old that worshiped the ground that I walked on. She would do anything that I asked of her and she did. She even gave me her virginity when I asked for it.
Gretchen was looking very good the day that I asked her. She was in an orange bikini top and a pair of white short shorts that looked like they were painted on. She had on open toed shoes and her fingernails and toenails were painted bright red. She had on a light shade of pink lipstick too. I loved the way her shorts were tucked up into the crack of her ass and the way they formed a snug “V” around her pussy. That was when I told her that I would like to make love to her. I wanted sex of course but Gretchen was the girl that I loved, not just a fuck buddy, so making love was what I wanted to do to her.
I was a virgin too so it would be something that we would both remember for the rest of our lives. She took me up to her bedroom and undressed for me. I liked what I saw and when I got undressed she seemed to like what she saw too. I had fondled her breasts and her pussy on several occasions, I had reached into her panties, and I had sucked on her nipples too, but that was the first time that I had ever seen her naked.
We kissed and fell onto her bed and then we kissed some more. I played with her pussy like I had before when I gave her an orgasm with my finger, she had enjoyed it before, and she enjoyed it then. I felt that I couldn’t wait any longed and so Gretchen opened her legs for me, I got between them, and I thrust down into her. She gasped and I started to cum right away as I thrust into her. The whole thing lasted less than a minute but it was the most exciting minute of my life. I kissed her and got dressed to go home to dinner.
I was in seventh heaven all evening, I jerked off to thoughts of Gretchen that night, and I just smiled at school the next day. I never told anyone what I had done with Gretchen. I was truly in love with the girl next door.
The next day after school, I rushed over to her house hoping to do it again. Gretchen was willing but that time she wanted to be in charge. Okay!
I got undressed and lay on the bed while Gretchen stayed dressed and sucked on my cock. In a minute I was cumming in her mouth. She had a strange look on her face. She swallowed my cum and then ran into her bathroom to throw up. She brushed her teeth and came back out naked. She then straddled my hips and slipped my cock into her pussy as she squatted down on it. She moved about for a couple of minutes while I played with her tits and she played with her clit. Then I cum again. She told me to keep playing with her breasts and especially her nipples until she had an orgasm. That took a couple of minutes more but she really enjoyed it. Once again I got dressed and left.
I could not believe how great sex was and that I had pleased my woman like that. In my mind I was the best lover in the whole world…but apparently not in Gretchen’s mind.
The following day when I went over to Gretchen’s house for sex she was not there but her mother was. She then sat me down and told me the truth…I was a terrible lover and that I only took care of my own needs. She told me that she could teach me how to please her daughter or I could go back to jerking off. I didn’t want to jerk off anymore. I liked putting my cock in Gretchen and I wanted to keep doing it, so I gave in.
For the next several hours Gretchen’s mother taught me everything that I need to know to please her daughter. It was simple things at first like how to kiss better, how to use my tongue, and even how to unhook a bra gracefully. She taught me how to fondle her breasts, roll her nipples between my fingers, and how to suck on her nipples so as to give her the most pleasure. She taught me how to give her a massage from the back of her neck and down over her butt to her feet. Then she taught me how to do the same to her front. Part of my training was oral sex so I had to learn to like the taste of her pussy, to lavish up the moisture, and to swirl it around in my mouth before swallowing it. I even gave Gretchen’s mother three orgasm orally without using my fingers or my cock. Of course finger manipulation was a part of my training too on her nipples and her pussy but also on her asshole. I finger fucked her asshole until she begged my to put my cock in it. I came instantly and she made me do it again, and then again until I could last a couple of minutes. My final test was to fuck her pussy with her legs up and splayed way out to the side opening up her pussy wide. I had very little friction that way and besides it was my forth time to cum so it took a lot longer. Almost ten minutes later I cum in her and she congratulated me.
She taught me how to undress a girl, how to do it in a sexy manor, and how to pull her panties down with my teeth. I also learned that I was to please Gretchen before I got pleased.
It turned out that my mother was in on it too. She had taken Gretchen to a movie and then out to eat before bringing her home. My father and Gretchen’s father had gone away for the weekend. That way I could spend the night in Gretchen’s bed with her.
Of course we went to bed early and I showed her what her mother had taught me about undressing her, giving her an all over body massage, and then oral stimulation that ended with me giving her four orgasms with my mouth and tongue. When I did slip my cock into her I had secretly cum twice while giving her oral sex so I was fully ready to rock her world, and rock her world I did. I fucked into her missionary style, then doggy style, and finally with her ankles up around her ears as I filled her with my cum. I had looked at the clock and was very proud that twelve minutes had gone by and basically in slow motion. It was my best attempt yet and it was with the woman that I loved.
It was only about eleven o’clock at night but we were hungry again. I put on my pants and Gretchen put on a light robe. On the way past her mother’s bedroom we heard some strange noises so of course being curious Gretchen opened the door to peek in. What we saw shocked both of us. There were our mothers on top of the bed locked in a sixty-nine, each engulfed in their own orgasms and continuing to give their partner more pleasure too. We watched for a while then quietly closed the door before we were observed.
In the kitchen we fixed two peanut butter and jelly sandwiches, got glasses of milk, and were sitting at the kitchen table when our mothers walked in. Surprisingly they were both fully naked.
Gretchen’s mother looked at me and then removed her hand from my mother’s pussy before putting her fingers into my mouth. I had the honor of tasting my third pussy and possibly the best tasting one too.
Gretchen removed her clothes and the three women sat at the table and discussed sex while I was told to crawl under the table and start licking their pussies. I started with my mother first because she tasted so good. I decided that Gretchen’s mother was next on the list and finally Gretchen herself. As I licked I listened to the women talk about washing their pussies, giving themselves douches, and even inserting cherry flavored LifeSavers into their pussies to add flavor. Apparently that was what Mom had done before letting Gretchen’s mother eat her. Gretchen’s mother had douched with a vinegar solution. Gretchen on the other hand had my cum mixed in there and she had a well-fucked taste. I realized that Mom and Gretchen’s mother had only their own secretions in their pussies for me to taste. As I listened I found out that our mothers had been lovers since before Gretchen and I were even born. I also found out that Gretchen often joined them in the last few months. It was also their idea for Gretchen to have sex with me. At that moment I was giving Gretchen an orgasm and she told them all about it too.
That night I slept with Gretchen and Mom slept with her mother. On Saturday I got to fuck Mom with Gretchen’s permission. She had wanted to see what I had learned and also to see if there was anything that she could add. Mom gave me a very nice blowjob and told me that I tasted better than my Dad did or Gretchen’s Dad did. That was when I found out that our parents wife-swap from time to time just to spice up their sex lives. I thought it was cool that they did it openly and that it didn’t hurt their marriage. Then since I had fucked both of them she asked me if it would be all right if the men fucked Gretchen. I felt a pang of jealousy but then I remembered that I had fucked two other women so it was only fair to let her fuck our fathers.
Gretchen thanked me for giving her permission and then reminded me that she did not belong to me yet and that she could fuck anyone that she wanted too. She then said that she would sleep with each of our fathers once just to see what it was all about. Then she gave me permission to screw our two mothers all that they would allow, but no other women if I wished to screw her. I quickly agreed. Gretchen was all the woman that I needed but I couldn’t pass up the opportunity to screw our mothers again.
With everyone’s permission Gretchen and I slept together every night after that. We took turns sleeping in her bed and sleeping in my bed. On occasion Gretchen would sleep with her father and with my father as well as with her mother and my mother. Gretchen was very popular among the five of us.
Gretchen stayed in the Grade School for two more years before coming over into the High School with me. It was no big deal when she did though because she knew practically everybody that I knew. We had gone to all of the High School dances, basketball and football games, as well as to the plays and concerts that were being put on. Gretchen outgrew her Grade School the day that she lost her virginity and became a woman…my woman.
We both finished High School and went on to college. I graduated from a four-year school and Gretchen graduated from a two-year school before we were married.
Life just kept getting better and better. Then one day we had a daughter and became parents ourselves. All to soon Gretchen will be teaching our daughter and her boyfriend about sex.