A place to share your sexy stories
By MrPicky
#112296
It’s time to return again and pick up where Pt 8 left off. I am hoping everyone has successfully recovered from all the holiday madness’s and has returned to their realm of normalcy.
I had been relating to you about our first long day together and the various activities we were able to do that we had not had time for in our afternoon visits. We had just done another prolonged round of pissplay and I had been doing some more extensive azz and clit play than I had done before. We also had done some fresh veggie play. As I had related before, sister had been playing with cucumbers and carrots for years at this point and her cherry was long gone. I had picked on her about her not having had the cucumber preserved that did the deed. She had actually worn in out instead of popping it all at one time apparently because she said there was never any severe pain or bleeding of any kind so she was either lucky were gradually grew accustomed to the size of the cucumber. I think I had already described myself is not being exactly porn superstar material in the cock department. Over the years, I have had the opportunity to break in a lot of “brown-eyes” and “rosebuds” because I had the ideal size and shape organ to not split open a young and inexperienced rectum. At the time of this particular Saturday she had never been penetrated by anything but vegetables and fingers and a hairbrush or two in either the front or back orifices. In fact, if she was telling me the truth, her rectum had not been penetrated at all until that day. Well, I took care of all that by the end of the day.
While she was still a penis virgin, her pussy had been thoroughly reamed out by a couple of hefty cucumbers and a long and fat carrot. She had some pretty significant orgasms from this veggie play and had achieved an amazing level of wetness and lubrication. While I hate to use the word slimy referring to a first class pussy, she was probably slimy. For a non-squirting woman, she had made one hell of a mass in her bed. All of the azz-play had caused her to lubricate profusely in the front hole and it was running steadily down her thighs to the bedclothes. Back in this time, we didn’t know that you were not supposed to do ass-to-pussy without cleaning up first. In the process of fucking her ass I would feel it getting too much friction and I would pull out and rub my dick up and down her slit to relube it and the plunge right back in the rosebud. I came in her ass twice so that was also leaking and adding to the other mess. One thing that surprised me greatly was that she did azz to mouth immediately with no questions asked or hesitation shown. She continued doing this for 40 years and always said that her azz didn’t hurt the taste of my cum which she loved so much. She had remarked from the very first taste of my semen that she loved the taste and the way it felt in her mouth. One thing is for sure, she never wasted a drop if it was at all possible to save it.
Over all those years, we never went backward in the things we did. Everything knew we ever tried we kept going at it until we made it work. I’m not sure if this came from being naturally highly sexual or just naturally perverted when it came to sex. From this monumental Saturday onward if there was any way possible I would fuck her azz when we would meet. Sometimes it was just a few strokes but it was still enough to feel good for both of us. This was a woman who got off on penetration in either hole. I would be willing to say that there were many dozens of times that I fucked her ass with something stuck in her pussy to simulate double-penetration. In our next phone conversation after this day we discussed me making her a butt-plug. I was able to do this out of a piece of hard maple and it worked rather well for her for years. There’s no way to know how many days she went to school or later on to work with that thing up her azz and I am quite sure there were many days she had something in both. She did not care if her playing ended in an orgasm or not. It was the penetration sensation she craved all the time. Years later I would find out that she did a lot of fucking just to get that penetration sensation. It was like there was truly an itch that she couldn’t scratch any other way. She described a few of these situations in her journal as well as telling me about them. We always loved to share sex stuff with each other. She once spent several minutes on an Army phone line telling me about how she got off riding around Germany on a Ducati with her husband’s sergeant. More on that later on.
As you may have determined, I have not been true to an exact timeline in this blog. I have tried to relate our story by significance of events rather than chronological order. I will try to note these things as I tell you about them. Sister’s love of penetration took precedence over her virginity but at the same time she wanted to remain a penis-virgin, (How do you like that new word?) but she also had to give in to the need to feel something cylindrical in her pussy. She just naturally knew that insertion went with clit abuse and abuse she did. It is a wonder it was not worn out by the time she was old enough to drive. In our phone calls she had told me about times when she actually lost count of the orgasms she would have when she took a bath or had some other time alone. She had near constant contact when she was not visible to another family member. On trips as soon as the little sister would doze off she would be rubbing her crotch. While I think she was a naturally sneaky person like her mother, she developed some quite sophisticated abilities just in hiding her sex playing. I will touch more on this from time to time later on.
Now that you know pretty well all of her early deviant behaviors we can move up in time a bit to the next two significant things: 1) her dating life and 2) her horseback riding, both of which bothered me a bit because it dug onto our times to spend alone. For many various reasons, I did not have a fourth of the social life sister enjoyed. For one thing, I was not one of the top ten good looking guys in a high school of 700 students. Nor was I rich or athletic. My qualifications in sex were hidden by my trying to be somewhat respectful of traditions in the sixties and you just didn’t brag about such in those days in a smaller Southern town and school. I managed to stay in enough trouble for the sexual innuendo remarks that I DID make. It seems that sister was also guilty of making sexual remarks at inopportune times and was criticized by some adults for doing it but no one told her mother, thank goodness. One teacher was a bit testy about how long she took in the bathroom since she always played a little on every trip. We always figured that this teacher was also guilty of the same things so she recognized what was happening. She never demanded to smell her fingers, though.
At the beginning of all this fun we did very little or no discussion of it when we were away from each other. Both of us found out that when you asked someone else about something sexual that they would draw up into a ball, so to speak, and not only shut you out but would laugh at you or call you a “perv” or worse. We were functioning on a level unimagined by others in our age groups. If we did ask something of them 95% of the time they could not even grasp the question much less the actions or the answers. Most other kids were nowhere near us in experimentation and we were too scared to open up to those we knew in their college years or 20’s because we thought they would inform to parents on us. We discussed at length how we thought that certain others we knew would act or react if they were in on our experimentations. Basically, together, we made the assumption that everybody else was also experimenting in sexual matters and that was correct. The difference though was in the fact we were related, therefore we had connection there, sure, but we also went to levels of experiments most other people would never get to at all even into their 30’s and 40’s. We had access to just enough reading material plus our own imaginations that there always seemed to be some new thing in the wings to give a tryout. Without really seeing it at the time, we eventually figured out that we were blessed with being intelligent in general, having an “over-sexed” imagination, and extremely curious about what made us have all these feelings of heat inside and the outward manifestations such as hard nipples, hard cock, wet pussy, tender spots like clits and balls, hard cock, internal twitches and spasms, hard cock. You get the picture and I hope you also have some memories to go with that picture.
Sister was allowed to date a little young at the time I thought. I didn’t know all the tantrums she had been throwing to be let out on Friday nights after ball games and Saturday nights for social dating and parties. She had her eyes on a guy who lived maybe a quarter mile down the street who was two years older, my age, and the star of the football team and who some of the cheerleaders had whispered about him having a big dick. I was too naïve to realize that much of the large veggie play had been doing two things- giving great sexual satisfaction to sister and preparing her for somebody’s big tool. She had not confided anything to me about turning into somewhat of a size queen where not only her pussy was concerned but her ego as well. She was determined to make use of her looks and now her experiences to hook this “dreamboat” into her web. She was not going to give up and let some other hotty from the high school or a college somewhere nail him down. She was willing to do whatever it took to be sure none of her competition got the old boy ahead of her. I’ll get back to this later so as not to throw the timeline completely out of focus.
This looks like another good place to break so I will. Be back in the middle of the week.

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