Teddy's World
Chapter 2

Copyright© 2014 by BUICK GS

Coming of Age Sex Story: Chapter 2 - Meet young Teddy, who is just trying to end his virginity and ends up opening a whole new can of worms, complete with a hidden family mystery, cheating, lots of sex.

Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa   mt/ft   mt/Fa   Fa/Fa   Fa/ft   Mult   Consensual   Romantic   Reluctant   Blackmail   BiSexual   Heterosexual   Fiction   Historical   Cheating   Revenge   Incest   Mother   Son   Brother   Sister   Daughter   Cousins   Grand Parent   DomSub   MaleDom   FemaleDom   Spanking   Group Sex   Harem   Polygamy/Polyamory   Interracial   White Couple   Black Couple   Black Female   Black Male   White Male   White Female   Oriental Female   Hispanic Female   Indian Female   First   Oral Sex   Squirting   Lactation   Pregnancy   Cream Pie   Size   Hairy   Violence  

The story begins in the mid 1840s; Daniel Mason and his brothers Mike, Tony, and Wilson began a family trust at first working for other’s after stumbling up on some gold hidden in a wagon that didn’t burn after in Indian attack. The brother stopped the handful of braves left unharmed before they could complete their mission. This wagon was huge; many a man thought Daniel, and his brothers were just some dumb city boys. They had an oversized wagon using 12 Missouri mules to pull a coal wagon. First between the weight of the gold and the coal, they needed all those mules. Daniel was glad that was all they saw too at first. After they sold the coal for $500.00 they were on their way trying at first to run a freight outfit, hauling just about anything that they could get paid to haul from point A to point B.

They began quietly to buy land in their hometown and the surrounding area. Mississippi was open if you had ready funds and the brothers had this, after found the gold by accident. So they set up to build a very large outfit, also becoming landlords to businesses as well as single family homes. Pride is a good thing when doing things in secret, many had ideas that the local dumb freight haulers were in so many deals. Many thought the brothers would not return with the money per the contract. The first thing the brothers did was after buying out some small farmer was to get them to agree to sharecrop for an additional three years or either the farmer or Dan got someone to fill in the farmers place if the farmer couldn’t or wouldn’t stay for the three-year term. If the farmers agreed to stay, then the brothers would pay them the balance owed plus a bonus for agreeing to sell and then staying as per the contract.

So the farmers had a larger nest egg in the end. Other than a few who wanted out for whatever the reason the brothers got their deals done. All four of them hated slavery as they all admitted how they felt bad about the way the slaves were treated. If the tables were turned those on top would not have wanted the same treatment. They came to an agreement between them after thinking of what to do as they knew in three years the workforce to make this happen would be a huge undertaking. The answer came to Daniel as a result it was understood that the only overseers would be Masons, and once everything was in place if it worked like the four of them hoped, then they would have the model workforce and power to do as they wanted, and the hell with any who didn’t like the way the Mason Group ran their show. Daniel set up a meeting with most of his young cousins with whom he grew up, mainly those not in line to inherit as they had older siblings set to get all of those perks.

After having the meeting to tell them of his plans since like him, they had an older sibling, thus very little was available for them to inherit. Daniel made sure to explain to them that it would be four to five years before they could be running around in the wealthy circles. Dan asked those who said they wanted to join in the family trust, they were also told upfront that they had to have something to bring to the table be it, a skill or money or both. It was understood what was expected of them. Needless to say they were welcome to leave at any time and take their percentage at anytime with proper notice of course.

Daniel made it clear abusing the slaves was a fast ticket to be gone, or worse. Then you would only be taking your original investment, provided you invested money, and or a serious ass whipping! (Depending on the reason you were asked to leave it may just end up looking like you just had vanished.) Mike was put in charge of build three bunkhouses in addition to the one already there. Tony and Wilson were the ramrods of the outfit. After four months of work, Daniel first bought many of the older workers who were no longer in their prime provided he could purchase the wives as well and first choice on any kids, in other words, he wanted the whole family. After grumbling and haggling, he got his way, sometimes he got the better end of the deal other times not. To do this foul job, he had to learn the going rate in all parts of making these purchases. It was thought they should concentrate on the young groups of 14-20 for males and 12-17 for the females. Trying to get the most for their money, while also trying for the so called best. This is what they did until just before the start of the Civil War.

Nobody ever noticed he was buying slaves, but was never noticed over time that Daniel always had room for new slaves, as he should have run out of room for all of them long ago. The power of greed just becomes blind as long as a hand is out to take the money.

I tell all of you this because my Mom has not shown that she wasn’t prejudice until very recently when she found a girlfriend who is black. Imagine the shock in the family? They broke up two weeks ago, and my Mom hasn’t been fit to live with since. My brother in-law said she had to go. And that was after only one week. She left her job within the family trust before it affected business. But the other widows asked her to move out until she got herself right once again. The four widows control the trust completely. They are the only ones living there for some unknown reason. As they won’t say and we have asked more than once. Each is a Great-Great-Granddaughter of the original four brothers.

I had to tell you this to help you understand what is coming your way. My younger sister Susan just got her JD to become a Lawyer and is studying to pass the Bar. Sue intends to only face this hell one time. Her apartment is a one-bedroom affair, and with her studying, there are books all over the place. Well, there is no room at the inn there, my brothers both moved out of state and work for the Trust elsewhere, but both said they didn’t want to deal with the mess Mom has become.

My Mom is very straight forward and doesn’t suffer fools well. You are hearing this because my Mom will be here Monday Night, and will not be willing to accept what has been or what will continue to go on. When I turn up pregnant, she will want to know who the father of the child is. I can’t and won’t attempt to knowingly lie to my Mom as she can tell about lies soon after it is told to her. In fact all the widows have this ability so please don’t try to lie. Little lies like you washed your hands, when you know you didn’t, lies like that will just make her laugh at you. Unless it turns into a pattern. So you can see she will be on to us within days. She will attempt to take both Sharon and me away from you. Are you willing to fight for what you have attained?”

“Yes,” I said.

“Well now, my Mom is used to intimidating people because of her looks (She looks like Sarah Palin), the way she talks to folks when she wants her way, and because of her size. My Mom’s name is Pamela Benett; she stands five foot-eleven inches in her bare feet. She weighs in at 225lbs. and is a serious gym rat. Before you start with pictures in your mind, she like most of the women in the family resembles Amazon women. Mom is much more muscular than you are. In the last four years, she and one of the other widows got serious, and it became a game to them to bulk up (No Roids!). Most of her clothes are either tailor made or come from Roger’s Big & Tall Store. Bet you have been seen in there yourself more than a few times. She is used to getting her way. Other than her breasts which are very sensitive, she has no real weaknesses that come to mind. She has not had sex with a man in nearly four years. The tomboy in her hates to lose to males in any way. So now you have been warned. And we will be of no real help to you against her.

We put the young girls to bed and we three went into Sandy’s room, closed, and locked the door. “As Mom will be here Monday if you plan to get together anytime soon Master, tonight is the night.” We all undressed, Sharon laid down on the bed and Sandy began eating her out after she licked her through her first orgasm, I laid down next to her stroking my dick, Sharon got on top of me and began to slide that wet tight virgin pussy over my dick. She gasped as her hymen went away forever. About a minute later, we were completely as one she looked over to Sandy and said damn that hurt! Mom I feel so full, Sandy calmly told her I had the largest penis ever to get between her thighs too. We slowly fucked until I blasted off inside her, because she was on top, she managed three to my one. With Sandy sore from last night, and Sharon from tonight so the fun and games were over for tonight and for the foreseeable future.

The next morning we showered and began breakfast talking about the what if’s over her Mom coming, and what we could do. After last night, I had a reason to visit often plus the study help Sharon was giving me. “Have you started plotting how you intend to get my Mom to let you keep the two of us?”

I had a vague notion of a weak effort but wasn’t willing to share it with them just then. Sandy looked at me really hard like she was putting two and two together, and felt the need to tell me nothing past spanking her about the ass would be tolerated. No offense but from the original Daniel until this day, domestic violence simply wasn’t tolerated. Once few examples were made before these type of things went away, for the most part. It was also understood a woman was nearly as responsible in a domestic dispute as the man or vice-versa should the woman turn out to be the abuser.

My Mom called as we were getting the girls up and said she would be here in about two hours. Shelly the little ringleader wanted to play some more outside before my Mom got there. Listening to how the weekend went for us the girls doing whatever they did, and me playing ball as she was getting her lies ready for my Dad.

We hadn’t been home 30 minutes when the phone rang “Where the hell have you been all weekend bitch?” To say my Dad was warm was meant you were seriously brain challenged! Theodore Daniel Mason Sr. was very pissed off!

My Mom slick as you please said, “We were over to Sandy’s where she, and the girls did girly-girly stuff. I say again whatever that shit is. And we all slept over at Sandy’s as Sandy seemed to finally be coming to grips with widowhood,” my Mom told him. I went out to cut the grass as I didn’t want to puke listening to a master of the lie at work. However, living with her would help me with Pam as my Mom is no shrinking violet herself.

I was on the scene Monday evening when a Black 1978 Ford Bronco that Pamela Benett was driving rolled into the driveway. We all walked outside to greet her; I have to say the pictures and descriptions all failed to convey the real beauty in front of me, and right about then she commenced to speaking to me. Any fog I was in ended abruptly as she had just told me rather sharply about her luggage needing to get in the house, and that was something I could see to while she talked to her daughter. Sandy and Sharon both Froze as Pamela started towards the door. I said, “Hold up, we are all out here now, my Dad always said don’t go in empty handed.” Sandy and Sharon both helped me to begin to take the luggage so Pamela helped as well saying I needed better manners.

When my Mom arrived on her way home to meet Pamela, who told her just to call her Pam. She then told my Mom, Marilyn, “Your son has some bad manners.”

My very first thought was OH SHIT! My Mom wanted to know what happened from that point, so Mom was told by Pam EXACTLY what I’d said. My Mom clouded up; I wasn’t sure which way she was going to go; I’m nervous now. Mom stepped to her, both in heels, so my Mom was still nearly six inches shorter. “I will have you know my child has home training! However, I am sure as hell not raising him to be your flunky either. I’m sure you had a hand putting your shit in your damn truck so it stands to reason you would be helping to get it out. Please know messing with him is messing with me, and I don’t give a shit how big your ass is I have no fear of you! So kicking your ass is not something I am too scared to try to attempt. With that we will take our leave before you, and I are scrapping right now!”

I was the first out the door as my Mom is very mercurial once stirred up, and I didn’t plan to be the one getting the ass whipping, and not knowing if she and Dad were ok again after this weekend’s mess. I bet you can guess what the dinner chat was in our house. My Dad said I should have just done it as a man, but on the other hand, you showed real brains turning it around like you did, and he gave me a thumbs up. “Ted you have to see this woman to believe what I am about to say to you. I know you played college football and all, but she is nearly bigger than you; she is nearly as tall as you in heels also.” My Dad nearly choked on his food when my Mom told him it was all muscle too.

This set the tone for the week with Pam quietly messing with me as to what I was doing with her granddaughter as Sandy should be keeping a closer eye on the situation to her way of thinking. She had a feeling she had not uncovered everything going on around here. It was a strong feeling too. The more I told Mom about Pam’s actions the funnier she thought it was, as she was beginning to think, I was sweet on the woman. She knew I was sweet on Sharon, so she and Sandy wore that joke out to no end.

Talk about the family vacation had picked up as we were spending a week in with Dad’s people in Jackson, Mississippi and a week with Mom’s folks in Columbia, and Nashville Tennessee. Dad had not been back to Jackson but once since he left in the 1960’s so his brothers got Mom to light a fire under his ass about going, and you see how that ended up. Plus my Dad had never been to Columbia, and my Mom wanted to him to see where she visited each year.

I needed to clear up the Pam situation and wanted to do it over the two-week family vacation. When I approached Mom about this, she was against it, and Dad said if he had to go, then everybody has to go. Mom said if the girl likes you; she will still like you in two weeks when you get back. Now after living with her, I know that sometimes you have to think fast, and know how to open locked doors too. All you needed was the key, and in this case, it was $500.00 to paint her trim and several rooms and a few other odd jobs.

After confirming this, Mom still was not interested in letting me stay behind. Until I mentioned I would be using most of it on school clothes. Man her position turned so fast, whiplash happened to Dad, as she said. “The boy is staying here.” Here comes a few pitiful but ... b b b ... from Dad, but which quickly died off after he looked down on her icy stare.

As they dropped me off that Friday night after we went and ate at Wendy’s as they were leaving early in the morning and were not going leave to me in the house alone for the two weeks that they would be gone. When he met Pam, Dad asked did she live at the gym, or just visiting the place too often? As she was larger than he could believe even seeing her, she could see he knew his way around those kinds of rooms himself. “No Ted I just used to go three to four times a week heavy lifting; I have a younger cousin, she is slightly larger but a little shorter than me.

I was back to that living room floor again, but all plans have rough spots, and this is just one of them. Pam watched me both Saturday and Sunday and a few times Sandy, and I seemed to be more than what we were supposed to be. As we taped off the woodwork in all the rooms. She expected this with Sharon as she had been informed that we were dating. Though Sharon was one year older, and we all know in high school that is much, much older. Come Monday Shelly left for daycare, Sharon to summer school to stay ahead in her classes, and then to her best friend’s house, and Sandy left for work. (Rat’s off a sinking ship if my opinion counts for anything.). As I was painting my first room, Pam came in ‘to keep me company’ I had no idea that I was lonely at anytime though. I had a boom box going while working, I was playing a cassette tape of Teddy Pendergrass’s new album ‘Life Is A Song Worth Singing’ when she came in, and the song that was playing was “CLOSE THE DOOR” which is about a seduction of a woman by her man. Pam was distracted by Teddy Pendergrass, while trying to question Teddy Mason. Now when she started picking on my work from; being too slow to missing spots, I thought about what Sandy had told me about her Great-Great-Great-Grandfather did in his time I moved to Pam to do what Daniel would have done to a woman acting out in his household, I was met with resistance.

We ended up on the floor wrestling to control the other. As I had her arms above her head leaning my weight on them, and the fact that I have been in a weight room more than a few times myself, I could hold her much stronger arms where they were. I could see her nipples as she was braless her nipples were huge. I mistakenly thought she was aroused, I leaned down and began sucking hard on her left nipple through her shirt, and she started cussing and trying to get her nipple away from my mouth as her nipple seemed to be getting longer. I switched to the other one as the moans started; her nipples were in the one-inch range when she was aroused, well now, she really was becoming aroused. When she could no longer keep still as her hips were starting to thrash about, I kissed her for the first time. I continued to kiss her when we began French kissing; I released her arms, she which then wrapped them around my neck.

I then pulled her to her feet, and we went to Sandy’s room. Pam objected, but as I kissed her and played with those nipples, she changed her tune, I pulled her T-shirt up, and she took it off, I took my own shirt off. When I put my hands on her thick muscular ass, I just kept kneading and kissing, I dropped to my knees and pulled her elastic shorts and her panties at the same time. Her clit was bigger than Sandy’s or Sharon’s, I couldn’t resist licking her clit, then I stood up, I want to lick this pussy in comfort, so we got on the bed. I did the best I could with the limited experience I had. She put up with me fumbling for about 15 minutes before she pushed me away saying that she was too sensitive. I was getting my face kissed by Pam, she said I both smell and taste good I started touching her clit again, as I was in position after rubbing my dick in her slit Pam sighed as I started pushing to get in, to be a Grandmother, she was very tight. I started long stroking her after I was all the way inside her tight pussy when we reached a rhythm we both liked were sweating both making plenty of noise. I came in Pam and because of how hard she was milking me during her climax, I stayed hard and fifteen minutes later I came a second time while Pam was babbling incoherent words at some point she was cumming continuously. As sleepy as I was I tried to cuddle with her. When I woke up, she was still asleep, so I covered her up and showered.

I finished the first room and cleaned my brushes and rollers. I then went to make lunch for us. Pam went to take a bath, I found out as I went to check on her. She blushed and said, “I have never done that before you are only the second man that I have ever slept with.”

“It is ok,” I told Pam, “I know what we did is a little unnerving to you, I won’t be saying anything about it to anyone. Ok just relax.” She redressed and had lunch with me. “I feel compelled to tell you about my family.” Pam said.

I listened to most of what I already knew, but she added more facts also. I knew that Daniel treated all the slaves as equal men, and they were taught to read and write. After they had learned a skill, they were paid half their salary to pay back what was paid to acquire them. For those with more skills or willing to learn and do more skills well their pay went up also. In this, they were treated equally. Once they had paid back the Trust in full for themselves Daniel freed them to become a free man or woman. They could join the Trust at a lower rate because they were not in on the beginning, and their family wasn’t born into the Trust.

However, they didn’t pay rent or for food either. They were free to leave either through the Underground Railroad, or with Daniel giving them $150.00, a new rifle and pistol and a horse. If you were caught you would be claimed as a runaway slave. I will do what I can to help you if I can. But you would most likely be on your own as the greedy men who catch you won’t let the truth to come to light, as this is how they get paid. Many stayed while others took the railroad option where they got everything but the horse.

Those that stayed became part of the family with most of the privileges, including carrying guns, being able to speak freely within reason. After Daniel showed he was willing to kill about anyone living in his group no matter the color.

And only a few exceptions to this were permitted. And just saying his black, Asian, or Indian man was in the wrong was not good enough. If any harm came to the man past a few scratches, offenders were given the same treatment, including death. And none, and I mean none of the women was disturbed no matter the color of the woman. After the word got out about the bracelets that all the women wore.

Because when Daniel came, his group knew no difference in color in these matters. And all colors were armed and willing to kill including women carrying guns. Before the Trust left Mississippi, Daniel had men working on other people’s land as his people prided themselves as being the best around, and believe you me, the men in these crews were of all colors, including white on these crews even though the leader might be black.

Daniel made it clear after a better way to do it came from the black crews more than once. And a Black crew asked for a certain person to do this or that. Daniel could see some safety issues were ironed out in some of these first diversified groups. Not to say everybody wanted it that way, as some on both sides for most of the times, different reasons wanted to work with their own kind.

With some exceptions where segregation still worked better most groups were diversified. Because every man agreed with the most important fact in the conversation, they all wanted to return home the same way they left to go to work.

Now while no black men were ever knowingly kept company with white women, we are sure more than few did including many widows, and mature women as well. More than a few black women married white men. Though some of the black men did marry into the Asian, and Indian families as did some of the white men. A person’s share in the trust was passed to a spouse even if his spouse wasn’t in the trust themselves. Otherwise, it passed to the offspring listed.

Just before talk of war became serious Daniel sold his businesses and his bank as he was sure this didn’t bode well and the women in the family promised he would regret not leaving before the war broke out. He had learned to listen to the women about things over the years. The women had yet to be wrong, and they had never challenged his leadership, or tried to take credit for their knowledge. Daniel always openly praised their gift, and made it clear this was just another valuable skill the family possessed.

He was just about the wealthiest man if not the richest anywhere near himself. Mike, Tony, and Wilson were very wealthy. Just not as rich as Daniel because it was Daniel’s drive, and vision that made it all work. Daniel left his vast fortune to a relative he said neither he nor his own kids would ever meet. He left a small part of his fortune aside for caring for his very large family as Daniel was like the Mormons he had more than one wife. In fact, he had wives of all colors and dared anyone to bother anyone in the Trust bar none. Daniel said many times that the person who came forward to receive the trust would not know they were in line to inherit the trust.

Those women in the Trust either in charge, or in the management of the Trust would know when they had the right person, at that time in the future. And it would be their job to prepare him, for his new role leading the vast fortune the Trust had become. And anyone who raised hell was to be released from the trust with no option to return. When asked about this Daniel said he had no clue, but this is what he was driven to do. After being told so by the women of the Trust who have always been the real and true leaders.

Teddy was intrigued to say the least. After lunch and hearing this story he cleaned up knowing he was done for the day. Pam was sitting in the living room feeling better than she had in years. When Teddy sat on the couch near her, but her snuggling to him surprised both, him and her. When he started kissing her, she knew he would soon be without her panties again in the next few minutes. Teddy fucked her twice more before Sharon came home.

Teddy was almost done making chili for dinner. Sharon just watched him and a few minutes later he when done. He walked over to her stool and kissed her with passion, and then she asked, “Where is my Grandmother?”

“She is in your Mom’s room sleeping.”

Not understanding Sharon asked, “Her room is downstairs. Why is she in Mom’s room?”

“We came to an understanding thus all the tension around here should be gone.” Teddy smirked.

With Sandy due any minute Sharon went to see about her Grandmother, “Come on Granny time to get up, Mom will be home soon and Teddy fixed chili for dinner.”

Pam had no idea what to say to her Grandchild as she was also feeling so strange concerning young Teddy. Sharon brought Pam’s robe and slippers while Pam was in the shower. She was changing the sheets and making the bed when Pam came out of the bathroom and hugged her grandchild and said, “I am so sorry.” When Sharon asked what for? Pam simply said, “I had sex more than once today with your boyfriend Teddy.”

“Don’t worry about it; I knew that when I came into the room the scent was still strong.” The red from her blush that couldn’t get any darker. “Granny he’s my man, when he is old enough I intend to marry him, but you can borrow him all you want if you are a good girl.” Pam was just wide eyed shocked and chose to say nothing further to embarrass herself. Pam had never been this unsure of herself in her life. In fact, she had always been a leader, so feeling unsure of herself is something she hasn’t been in years.

Dinner was on the table when Sandy walked through the door minutes later, Sandy teased Pam telling her she could get used dinner on the table after a long hard day. Pam who was a little nervous about her day’s activities, said that, “Teddy cooked this chili, not me.” Pam was very quiet during dinner. All was quiet until Shelly went to bed, after which Pam confessed all she had done that day, after which both Sandy and Sharon tried to comfort her. After she stopped crying somewhat Sandy told her Mom how she agreed to be Teddy’s submissive woman the Friday before she moved in. Sandy went on to tell Pam that she may be already be pregnant, though she has only been with Teddy two times since Pam had moved in for fear of getting caught both times her Master made her fuck him.

Teddy was right all the tension was gone as everything was out in the open. Pam came to the realization that she would continue willingly to spread her legs for Teddy, and no longer felt any guilt about the matter. She didn’t feel as though she was a submissive, unlike Sandy, who was very clingy to Teddy. For Pam, she could not understand this overwhelming desire to have sex with Teddy as not only was he a minor, he is black, and he was also introduced to her as her granddaughter’s boyfriend when she first arrived. This was very unnerving though surprisingly not stressful to Pam.

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