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  1. MISSED OPPORTUNITIES AND REGRETS 1 [NEW STORY]
  2. MISSED OPPORTUNITIES AND REGRETS 2 [NEW STORY]

MISSED OPPORTUNITIES AND REGRETS 1 [NEW STORY]

Categories Fantasy, Erotica, Interracial, Teen

Authror: James Dylan Dean

Published: 10 July 2018

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In this story, no one under the age of fourteen has any sex.

And it should be noted, that this is just a story and not a diary of my experiences. Author’s Note.

Some time ago I wrote a series of stories entitled: WHAT IF 1 thru 4. These stories are an updating of them, with additional accounts. None of them really happened. They are only second guesses as to what might have happened at nexus points in various romantic adventures in my life.

MISSED OPPORTUNITIES AND REGRETS:

I guess that almost everyone in their later years looks back on opportunities that they passed over to their regret now. Can’t be helped. A lot of opportunities missed were in a bunch of opportunities, where only one or a few could be chosen, thus looking past some others that just couldn’t be wedged into the spaces that they might have thrived in.

In my current exploration of this issue, I will look back on some romantic opportunities that I just flat whiffed on. And I will, because of the sensibilities of this board, they start out at my age of fourteen the earliest.

And I have to acknowledge the presence of an Obi Wan kind of influence on my right shoulder and a Darth Sidious one on my left. In my real life, I like most listened to the R/H side most often and suffered some serious slugs in the ribs, when I lowered myself to the L/H side. But, for the purpose of this dissertation, I will assume that I would have gotten off relatively unscathed, if I had leaned significantly to my L/H side with some of my romantic decisions.

At age of fourteen, I was in the ninth grade in a Junior High School as they called them in those days. I was the youngest in my graduating class and so was always a grade forward of where my age would have naturally put me. It was not due to any educational genius or anything like that, though I did after a first two grade struggle regularly get fine grades. But, it was because I was moved from one school district to another when I was about to be put into kindergarten and ended up in first grade instead. No one ever thought to correct that error.

But, in the ninth grade, I was just beginning Algebra and other courses much more testing than what I had dealt with up to then. So, they took up a lot of my attentions. Besides, I was to start ninth grade, still sort of short for my age, very slim and a member of a very unpopular religion. This severely restricted any romantic interests in coming into my life. Even though, I was expected to only pursue girls in my faith, they were determinately not interested in me at the time. This was not due to any bad impressions that I made, most of them were rather polite to me. I was just not equipped by temperament, possessions (like a car,) nor the look to get their advanced attentions.

The girls in my neighborhood had much of the same attitude towards me. Only one, a rough and ready gal, showed me any malevolence. But, she was of a stocky build, but not at all unattractive, but was resistive to any boy’s attentions. Interestingly, her mother was one of my dearest confidants at this stage of my life and would respectfully discuss ANY concerns that I might have in my youthful development. I actually learned a lot more from her in my advancing at the stage of my life than anyone else, male or female, that had any influence on me. But, she didn’t bar me from her harridan daughter, instead she protected me from her.

There was another girl next door, who was very cute and nicely mannered, but she was sweet on a guy just across the street from her and they eventually married and seemed very happy together.

The only girls then that gave me any attentions at all were two girls of the only two black families in town. They were not poor people and were also from a very strict religion, just not the one that I belonged to. They first came to my attentions in gym class when we had to learn to dance. No, not the rock-n-roll or other popular dances of the day, but ballroom dancing, like the Waltz, the two step and the Schottische. I didn’t object to the dances, but until the two ebony girls started to dance with me, I had a very hard time finding partners. If other girls were assigned to me, they didn’t get out knives and stab me in the back, but they let it be known to me that they were not pleased by it.

At that time, Mill City was not a hotbed of racial strife. The worst thing around then was the prejudice against ‘indians,’ which was a horror of its own. But, the two girls who were very pretty and pleasantly friendly, to even me, also had trouble getting dance partners in class, with the same results with the guys that were assigned to them. After all, the population of the city had come from all parts of the country, even the South, and their prejudices tend to be rather ‘catchy’ to those of little minds. So, there was a rather low grade backlash against the girls, though not at all virulent.

But, I was raised in a religion that deemed all people as ‘of God’s children’ with no racial prejudices at all. As far as I can tell, I never have had any such feelings in my life. I just have been raised to treat people as they are and act, not based on any preconceived notions about them.

So,…………. I was very comfortable in dancing with them, and because of this, they seemed to like dancing with me, too. Now, I never pursued anything with either of them. Just never thought of it at the time. But, what if I had done so? What might have happened?

Mary and Eloise are dear friends and just approaching the age of fifteen. There were no black boys of a viable age in town yet, so their social opportunities were limited to fun with their families and each other. Both were chaffing at the bit, so to speak at the time and desirous of advancing in adult like behavior right away.

One afternoon, with them at Mary’s house and the windows heavily closed to view from the outside (a habit they brought from the South for good reasons) the subject of boys came to their attentions. Especially the lack of viable dating material.

“What are you going to do this weekend, Eloise? I am tired of doing everything with my family. As dear as they are. I would like to meet a boy and have some social fun with him.”

“Oh Mary, you have been on this topic for the last several months. You know that there are no likely boys of our age here for the present. We likely will have to wait until we are in college to meet any.”

“Oh, Drats!!! You mean that you are willing to give up three more years of dating and fun, to wait until college to find out what romance is like?” [Mary]

“What choice do we have? What boys locally would want to date us? It is not that any of them are cruel to us, they just don’t seem to be interested, since none of them are black like us.” [Eloise]

“Yeah, I know. The boys at school treat us rather politely. Even the ‘southern’ boys, since the teachers here would not put up with anything else. But, I think that they enjoy not having to act out their parent’s prejudices anyway. But, that will probably change as they get older and more assimilated into their social structures.” [Mary]

“What about Denny, the J.W. boy that the gym teacher keeps assigning us to dance with? He seems very nice, and he doesn’t seem a bit uncomfortable in dancing with us, does he?” [Eloise]

“No, he doesn’t! When we do the waltz, he holds me very close and seems to enjoy doing so. Do you think that we could talk our parents into letting us date him though he is a J.W. and a white boy?” [Mary]

“I don’t know. They might not like it that he is white, because of the usual attitude of white boys towards black girls, that they are to be used. But, heck! Many of the black boys feel the same way and would never treat a white girl like they thought that they could get away with in treating a black one. And besides, since he comes from a religion even more strict than out Baptist one, that might work in our favor.” [Eloise]

“You know, you might be right about that. Let’s try and run that by our parents to see what happens.” [Mary]

What happened was a lot of resentment and resistance from both sets of parents over this thought. In addition to the age issues and the issue of me being white, there was the worry over a backlash of a white boy and a black girl dating. But, with the obvious concern of the girls missing out in their youth in what a lot of other girls were already experiencing, and with no suitable black boys in the area for them to practice their wiles on, they relented and agreed to meet this Denny boy on their own home turf, one of their homes.

So, they set up things with me, with saying that they each needed a bit of help in doing the poem memorizations for English class. We each had to memorize a certain number of lines of poetry to pass this class. We had the whole year to do it, but time was running out on our efforts and the girls were only half way there. I hadn’t yet recited one word of one, but everyone was expectant of my doing so, since I was a vocal busybody in class. Why they didn’t just do this between them, was glossed over and ignored by them and me.

So, on a Saturday afternoon, after I had been out in the door to door with my religious friends, I was cleared by my mother to attend to this meeting. She couldn’t wait to hear what the result of it would be, and that was probably the main reason that she okayed it. She was also concerned that I wasn’t getting along with any of the other females in my age group at this time.

So, I walked the fifteen or so blocks to the house and recognized it as one that I had visited in my ministry in the past. The people in it had not been interested, but had also been very polite to me in their refusal of the magazines or the invitation to attend our meetings. I had felt very good when leaving their door, though that was the usual reception that I got. Very few people were rude to me.

I moved up to the door and the mother came and recognized me. I smiled to her and said, I am sorry ma’am, but I don’t have any magazines today. I am here at the invitation of Mary and Eloise to help them on an English class assignment. She broadly smiled at my introduction and guided me into their home, their sanctuary from all of the world’s stresses and concerns.

At the sound of the doorbell, the girls had rushed down the stairs to greet me and then took me under their arms to move up to Mary’s bedroom for us to work on the school assignment. That was of course forgotten as soon as the bedroom door closed. The mother later came by and cracked it open, but when the girls saw that they soon closed it again and I guessed that mother thought that the two girls would well be able to take care of themselves after all.

The girls got out a monopoly game and we began to play as we discussed school concerns and the process of growing up and trying to get our parents to recognize our adult status. This was a bit premature at the time as you would guess.

And as the game progressed, with them playing ‘nice’ with me, Mary brought up that her aunt across the country was writing letters to her about a lot of adult things to help her be protected from doing anything that could ruin her future with boys.

My eyes looked up and my ears perked up at that, since I was feverishly curious about the same things. The books in those days, except for the pornography which was totally unavailable to young ones like us, were seriously short on deions and pictures of the things we really wanted to know. She was about to get the letter out and share it with me, when her mother came into the room and caught us playing a board game. “Aha!’ Came out her retort. But, seeing nothing to be concerned about, she asked if we would like some snacks, and we said, “Yes!” So, she left to get them for us.

In only a few minutes, she brought up some really good cookies and three glasses of milk. I thanked her and she smiled at that. A white boy, with manners! She was impressed.

When the door closed we were alone for several hours as the mother had to go downtown and do some kind of chore there. When the front door closed and we heard the car move out, the letter came out and the girls eagerly began to share its contents with me.

With bright and enthusiastic eyes, the girls began to share with me. Mary would read a section of the letter and then Eloise would explain it to me in words that I would understand. It involved a lot of sexual practices that I was totally unaware of. It mentioned boys kissing and licking on girl’s privates and girls doing the reverse for boys. It mentioned that oral sexual practices and the boy going up the girls, anal cavity was fun and avoided the production of babies. It told about rubbers that allowed a boy to go up into the baby making chamber of the girl, without a baby resulting. STDs were not of a concern among us at our ages and in those times.

After we had read the whole letter and digested the information there, the girls got a bit forward and asked if I would like to see the locations on their bodies that were referred to. I got really excited about that, because that was something that I really wanted to see and know about. So, first Mary, backed up on the bed and raised her skirt up high for me to see her panties. Without even knowing what was underneath, I got very excited at that. She let me rub my hand on the fabric in her panty area, and I could feel the warmth and some of the wetness there. I was a bit concerned that she had wet her panties, but since she was not shy about it, I deduced that something else was happening.

Then Eloise, opened her blouse and let me see and feel her small breasts. She usually wore a trainer bra, but had somehow missed putting one on that day. And when they had me move my mouth up to them after having fondled them with my hands, I was beside myself with enthusiasm. And when my mouth moved up to take in the nipple, I was transcended back to my nursing days with my mother and didn’t want to leave the small black and beauteous titty.

Mary, then mentioned that she would like attentions to her other area and so moved to the side of the bed and removed her panty to my delight in finally getting to see directly the very private place of girlhood. It was so gorgeous in its simple beauty. The little amount of curly hair, the obvious slit moving from her belly to her backside. The little ‘dick’ pointing out of the top of her crevice and soon the rosy colored and lip surrounded hole up into her lovely belly. I just couldn’t get enough of this.

At this point, they wanted to see my equipment in its entirety and so I bashfully, with a lot of their help undid my trousers and let them lower my shorts to bring their area of interest in view. They were very complimentary of my then unrisen penis and when it began to rise up due to their handsie treatments, they were even more amazed at it.

Then, they asked that I experiment with her ‘pussy’ area, as it was called it the letter, and promised that Eloise would play with my penis as I did so. So, Mary settled down on the side of the bed with her legs splayed out, and as I knelt on the floor before her, Eloise moved so that her mouth was on my ‘dick,’ as it was called, and began to work on me at the same time.

At first, I only paid attention to Mary and her pretty pussy. I smelled really good and tasted even better. As I was progressing in licking and suckling it, I thought that I could hear the door open, and a bit of a ‘whoop; from Mary. But, if it did, nothing else happened and we continued on our way.

As I progressed with Mary, I could taste something very sweet coming out of her birth port. It was smearing all over my face, and I loved it. I didn’t think that I would ever want it to be washed off. And while this was going on, I felt myself to be slightly leaking into Eloise’s mouth too. But, neither of them were making any effort at all to change our positions.

Finally, Mary began to heft her short and pretty body around under my efforts and then she let loose again out of her body and her tummy became a riot of shaking and trembling with her mouth letting out some very loud shouts. With this, I felt something spurting out of my dick and thought that Eloise would pull away, but she didn’t. I could feel her gathering it up in her mouth and swallowing it. She then took my legs in her arms and pulled her mouth up so that my dick was fully entered into her throat. She sucked on me very hard to evidently get all of the rest out of me and then relaxed and rose to kiss me on the face as I moved back reluctantly from Mary’s pussy.

With all of this done, we gathered up on the bed and hugged each other for some minutes, until it was time for me to leave. As I rose up to do so, they in turn kissed me very affectionately and asked me to come again. I said that I would, if I could and thanked them for inviting me.

When I got down to the living room, the mother was unexpectantly sitting on the couch. I thought that she would be downtown much longer than this. She looked up to me and said that it was nice that I could visit. And in passing she mentioned that she had heard shouting from up there. I just passed it off as her celebrating winning at one of the games that we had played. Mom was evidently guessing what that game might have been. And then she advised me that she would talk to the girls about me coming again. With that I took my leave and walked back home in a daze at having learned a whole lot about the things that I was very curious about at the time.

When I got home, my mother asked me very curiously about how things had gone, but evidently with the odors on my face, guessed how thing had worked out and smiled at me.

When I saw Mary at lunch the next school day, she motioned for us to meet out in the playground in an isolated corner and when I got there, she told me that her mother had checked her out to see if she was still officially a virgin, and when that was determined to be true, despite the obvious ‘fun’ that we had had, she told her daughter, that she could continue to see me at their place as long as that remained true. Eloise’s mother didn’t seem as concerned about this, when she was told of what had probably happened at Mary’s home. And I was welcome to go there too, if the opportunity presented itself.

I had visited on several times at each of their houses over the next couple of months and things had stayed the same. We didn’t always play intimately, but when we did we traded the girls in the places and things went pretty much as it had on the first time.

Then on the Christmas holiday, Mary’s folks decided to travel back home to the grandmother’s place for the holidays and so Eloise and I were left to ourselves. Since, her mother wasn’t as concerned about things as Mary’s was, we found ourselves in her bedroom alone and with time on our hands. Two person monopoly isn’t that much fun and so after a few minutes of ‘hee hawing’ around, we got into some very serious intimate play. Eloise had a lock on her door, since she had brothers who were nosy about her business, so she locked it and we both got naked and entered under her blankets to do some more exploring.

After a few minutes, the boys came by the room and tried the door. When it didn’t open they threatened Eloise with telling on her to their mother, but she came by right about that time and told them in definite terms to strictly leave Eloise and her friend totally alone. Nothing was ever heard from them again when he visited her.

Meantime, I and Eloise were under the sheets and playing with each other’s bodies. She was delighted when I played with her pussy with my hands and fingers, especially when I accompanied that with suckling on her growing tits. And I was about out of my mind, when she did the same for my dick.

Finally, it got to be too much, and she whispered into my ear, “Do it now!” Without having to be instructed, I knew exactly what she was talking about and so when she backed up on to her back and opened her legs, I move my dick up to her widened out legs and took my first trip up into girl wonderland. And it must have been her first time, too. Since, I could feel something gently rip and then a slickness usually associated with bleeding occurred. When I looked down at my dick on one of the near withdrawals, I could see red on it, but she seemed to be unconcerned about it, so I continued on what came naturally and that was me gently probing in and out of her.

With this, her eyes got more than a bit wild looking and her mouth became twisted in a combination of a smile and grimace. When out of concern for her, I began to slow down and maybe to stop, she suddenly looked up to me and said, “No keep on, I am almost there!” I could guess where she was talking about, but no guessing was necessary when it came, and I emptied up into her at the same time. With that I relaxed down on to her tummy with my knees taking most of the weight and we just held on to each other tightly and marveled at the feelings that we had just experienced.

When we came out of our highs, we could think of nothing else to share right then, and so I excused myself to go home. When I got on the way to the front door, her mother took me into her arms and guided me to the door and smiled at me as I left.

When Mary got back with her family, evidently Eloise told her all about it, and then Mary was concerned that she get the same treatment, despite the promise that she had made to her mother. So, she arranged for her and I to meet up at the forested park, that with the majority of trees being evergreen, was still dense and with many hiding places even in the winter.

We met in a familiar hiding place to us, on a day when few others would be there, due to the wet and cold rain pelting down around it. But, in the place that we sought out, the trees over hung and so on the ground you only got a cold drop once in a while.

Mary didn’t want to waste time, so she spread out the blanket that she had brought and lifted her skirt up to reveal panty less privates for my adoration and usage. I got right down to business in giving them to oral treatments that she loved and then backed up for her to get me up strong and stiff. With that and her admonition to not waste time, I entered right up into her. There was no resistance, and so in some way she had already lost her hymen (Actually it happened at the dick of one of her cousins while on the trip.) and then I moved up deeply into her right away and she shuddered and moaned at my plunging into her and led me tightly around the waist as I began to move in and almost out of her.

She began to exhort me in my efforts and when we both came, she let out a sigh and grabbed me up to her and kissed me very fervently. Then we adjusted our clothes and dressed to go home.

I saw the girls for a few months later and then they invited me over and let me down gently. They told me how very much they loved me and had totally enjoyed our time of discovery together, but that with all of us approaching sixteen, that we would have to break it off, since there in those times, there was no future in it. There were other black families moving into town, and there were boys their ages among them. They also mentioned our religious differences, that would become much more important to them as they grew older and began to make families of their own. So, with a lot of tears, they dismissed me out of their lives and sincerely wished me well into my future.

I eventually married a very nice young lady years later and when I would see Mary and Eloise around town they would always smile at me. Some years after this we all met at a community picnic and I was introduced to their husbands. They took a look at me and wondered what this was all about, but the ladies covered over and just mentioned that I had been their dance partner during what was now called middle school when no others would do so. And both husbands, with a bit of suspicions that it had been more, accepted this provisionally and were very polite to me. My wife never found out about it.

When we all hit our fifties, they felt that enough was enough and so they would gather me up into their arms when they encountered me anywhere and whisper into my ears, that they very much remembered our fun and treasured the memories of them. I always left with a bit of heartache over what might have been, though my life as it turned out to be was very fine, too. And so was theirs, too!

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