Win Lose Or What

I pointed out that really, we had only been together four months out of four years. We had these big dreams we were working on. They were stuck at home in limbo. I'm okay now, I said. I really can understand why it happened. Everyone agreed. We had been immature and foolish when we got married in the first place.

I held up my beer as in a toast. "To us guys! We lost the girls, but we're a success! We all have a degree. We have no bills and I'm kicking ass at 23! Here, here!"

We all clicked bottles. Jack came over, squeezed my shoulder and said, "I'm so proud of you son!"

I responded with, "thanks, dad!"

Wilber, (Mr. Green) raised an eyebrow. Jack was nosed to toes smiling.

"Jack?" Wilber asked.

Jack shrugged his shoulders and said, "It's up to Ewell."

"What?" I said wondering if I had just missed something.

"Later," Wilber said looking at me and the guys.

Jack asked us how long we were going to stay. I told him we still had about three weeks' leave and would like to stay most of it there if it was okay. Hell, yes, it's okay he said. You guys can stay in the boathouse from now on!

******

Okay, let me tell you about the boathouse as Jack refers to it. We all call it the boathouse because he does. The boathouse is a 3800 square foot McMansion. The double car garage opens from the front and the back. On the backside is a long concrete boat ramp into the river. That's why he calls it the boathouse.

There are four bedrooms that all have their master bathrooms. Three upstairs and the extra-large master downstairs. There is a mother-in-law apartment just off the kitchen that Janis and April live in. They are Jack's lifelong friends and have a life contract to stay and care for the boathouse. Free room and board. Great pay, nothing out of pocket. Oh, and as far as we knew they were a couple.

Janis and April are at least fifteen years younger than Jack's age I think, around thirty-five to thirty. I don't know the back story and don't care. All I know is that they have helped care after me and the guy's whenever we stayed over at Jacks. I guess since we were in our preteen years.

At first, there was Janis who was working her way through college, a few years later April came into the picture. We always and still do think they are beautiful. Stunning really! I know I've enjoyed many a wank over them.

One of my favorite childhood memories happened when I was sixteen. I had come home to find my parents arguing in complete anger. It seems my dad had heard a rumor that mom was involved in a new relationship with another man

I had run to Uncle Jacks because I didn't want to be home. Uncle Jack was on one of his business trips, but April and Janis had allowed me to sleep in the boathouse. In the middle of the night, I had woken up and gone to their apartment.

It was quite a sight to see. Two very desirable women naked making out while trying to give each other the sexual release they each needed. Each exploring each other's flesh as if they knew it better than their own. I learned that each of them likes things done to them in different ways. From the soft caresses on the breasts to the sucking of their nipples I watched as they led each other on in their lovers' dance.

It was amazing to watch as Janis climbed off the bed and strapped the double dildo on her slender frame after asking. "Which one does my wife want. The black thick one or the long white one?"

April replied, "The white one because then I can pretend that Jack's nephew is trying to create in me the baby, I have always wanted."

It was at that moment I backed off as quietly as possible because I knew that if I didn't, I would have been discovered. It had been Janis that had caught me whacking off for the third time that night about an hour later.

After catching me Janis said, "Yours's would be an enjoyable ride it's a bit bigger than the average guy."

******

We took our bags down to the boathouse. Janis and April showed us what room to put our things. Imagine my surprise when Janis led me to the master suite downstairs.

She gave me a smile that knocked my socks down and said, "This is yours now."

"What? I mean... What? Where's Jack." I said out loud.

I'm wondering while I put my things on the bed and Janis started to unpack my bag and put things away why Janis had said what she did. I, of course, helped her, but I was also wondering why I felt that this seemed permanent. Janis walked over to me as we were finishing and ran her hands up my back in a friendly gesture. The problem to me I got the feeling that she was feeling me up. As a result, my body naturally began to respond.

"Jack has plans for you," Janis said. "I'm praying that you will willingly go along with them."

With that said I turned my face towards her, and she gave me a soft kiss on the cheek. What started as a simple gesture would have continued if I had not backed off. I asked myself while in the bathroom repositioning my woody to hide it where we would have gone if the timing had been different.

Until this time, we had always stayed in the main house. The boathouse is half the size of that. We ate most of our meals down in the boathouse but always slept at the main house. Janis and April are great cooks. Jack would eat with us sometimes. Although he spent a lot of time with us playing games, he had things that required his attention. So, Janis and April would watch over us. We always had full run of the place and man did we ever abuse it!

I think we were around eleven or twelve at the time. We thought it would be cool to take Uncle Jack's skiff out on the river and fish. Ernie caught us just before we cast off from the pier. Ernie is Jack's driver and boat pilot. I know he does a lot more than that, but that's how we saw it. Oh my, God, was he pissed. No life vests, no ores, anything that could help us if we got in trouble.

That was the first and last time Janis put us over her knee. Jack was mad because it could have turned into a disaster. He didn't punish us though. Janis had done that already. We had a time trying to sit after she was done.

Thinking about it now, she could have put me across her knee anytime she wanted. I'd bust after the first few whacks. Sorry, but damn! April too for that matter, but she just doesn't have it in her to do that. April is like a Penelope Good love. She is sweetness personified. She probably cried when we got spanked at that time. Easy to see why Janis loves her so much.

I know me and the guys love them both, a lot! None of us had ever questioned their relationship because we loved and respected them that much.

Jeff, Ed, and Jack were sitting at the bar when I came out of the bedroom with Janis. She had helped put all my clothes away. Jack asked what I thought of my new digs. I just walked over, hugged him and said I love you crazy nut. I love you too son.

There it was again, "son! Uncle Jack?" I asked.

"Would you like to be my son? You know, make it legal," Jack said? "It's only a few pieces of paper. You have always been a son to me. You and the guys have pretty much grown up here."

"Fuckin A! I mean HELL YEA!" I said.

Jack slid a folder and a pen over to me. He opened it and said, "Sign here. You boy's sign as a witness."

Janis and April both had tears in their eyes and kissed me on both cheeks at the same time. Nice I thought they can do that again whenever they want.

"Wilber will file this at the courthouse tomorrow morning," Jack said. "Not only are you my son now, but you're also my legal heir."

Wow, I hadn't even thought about that.

"One more thing," Jack said. "Sign here. Boy's sign here as a witness. Wilber will have Martha notarize and file this at the courthouse as well in the morning."

It was a quick claim deed. Jack had just signed over the boathouse and a two-acre parcel of land with it to me. I think I may have peed a little. I had no words. My ex parents are going to shit! Good!

Tom the father who had raised met me at Scallywags the next day because he wanted to talk to me in private. That was when I was hit with the truth bomb.

"Your mother's mother arranged your mother and my marriage when she learned that her daughter was carrying you. She paid off my parent's debts to get it done." Tom said. "Neither of us knew for sure who your father was until the car accident we were in when you were fourteen. Both my brother Jack and you are o negative. We needed his blood to save your life."

"Ouch so are the rest of my sister and brothers yours," I asked? "Who else knows?"

"Yes, the rest of your brothers and sisters are mine," Dad said. "only the four of us know the truth. The reason was that my brother wasn't considered acceptable to your mother's family because they did not like him personally. Your Aunt Mary Jane caused that because she was jealous that her sister had captured the man that she wanted. That hurt him so deeply that he became a different man. We learned much later that he had asked for your mother's hand."

Now the family relationships made sense. So did my changing relationship with Uncle Jack.

******

It was about a week later I was getting some sun in by laying on a towel out beside the boathouse. Jack was away on one of his many business trips. April came out wearing a very skimpy bikini which left part of her pussy hairs exposed. She was leaving very little to the imagination.

April was and still is a beautiful redhead. At five foot seven because of her lifestyle, she had a body that oozed of her sexuality. I could always see myself spending hours exploring her body. She was made to have her body appreciated by someone who loved her. I estimated her to have a thirty-four doubled d breast. About a twenty-six inch waist, her hips appeared to be about a thirty-six, which meant that when she wrapped her legs around her lover they would be locked in tight.

She was not wearing her top as she walked towards me. Thankfully I was lying on my stomach wearing sunglasses so she could not tell that I was looking at her. Her breasts bounced invitingly. It had been months since a woman had caused me to have a hardon instantly.

I had learned that both Janis and April were Uncle Jack's only friends with benefits. He saw them both as his being his wives and did not mind their bisexuality. Thanks to my other dad I had learned why he refused to commit himself to any permanent relationship.

She was standing over me before I realized it. When I turned around to lay on my back, I found myself looking at her very desirable body. I couldn't help exposing my instant hardon as it was automatically responding in anticipation because it was pushing against the shorts hiding it.

"Jack had a vasectomy after he knocked your mother up," April said. "Because he didn't want to be a father and settle down. Your mother convinced your father it was his, so he married her."

"I kind of figured that out on my own," I said. "The day he signed the boathouse over to me."

"Jack's ready to settle down and move us into the main house so that we can be a real family," April said. "but it comes with one big condition."

"I'm happy for the three of you," I said. "Tell my dad I will help the three of you out any way I can."

As I said that April knelt, so she was resting on her legs right over me. I could feel my hardness pressing against the softness of the warm inviting flesh of her womb. In my state of mind, it wouldn't have taken long for me to rip her bottoms off and shove my raging hardness into her.

She said, "That's good to hear because Jack wants us to screw the hell out of you until you have knocked both of us up."

With that, she leaned down and kissed me deeply sensually by shoving her tongue deep into my mouth to show that she was being serious. I responded with the willingness I always had towards her. I could feel the full ripeness of her warm breasts pushing into my upper chest. I raised my arms around her and pulled her down tight against me.

As her tongue danced with mine inside of my mouth, I realized that April knew what she wanted and was doing her best to try to convince me to be agreeable to it. After exchanging spit for quite a few we paused.

"It has been a long time since I have been kissed by a man that shows his passion and desire that much," April said. "I find it a complete turn on. Race you to your bedroom."

"I've been dreaming of making love with you since I saw you watching us from our bedroom door. Is your cock as long as the white one was," April asked with a giggle? "Janis has moved to the big house so for the next week it will be just us"

"We will have to be careful," I said, "When Jeff and Ed are around."

"Jack has sent them on a two-week fully paid fishing trip," April explained. "Janis wants two and I want three, so we are going to be fooling around with you for quite a while."

We walked into my bedroom together. I noticed she had already pulled down the sheets. Looking at me she pulled her bottom down proving that she was a real redhead. She undid the snap to my shorts and slid it and my underwear down. My little soldier stood out standing tall and proud. For the first time, I felt her hand on my shaft. I knew instantly that I would never tire of her touch.

Thus, our new family relationship had begun. I didn't last long the first time, but I made up for it by remaining hard. We fucked each other four times that night before we fell asleep. Each time I ejaculated into her, she had me remain in her to ensure that the little swimmers couldn't get out.

The next morning, our relationship began to change as we began making love. Our animalist urges now worked out allowed us to spend a lot of time in foreplay learning about each other's willing bodies. I learned that it took April longer to be aroused than most women, I began to slow down until he was ready because I wanted us to cum together. There is nothing better when making love well being in love. That was something we learned together.

By the end of her first time with me, we had made love in every room in the house. April was finding it hard to leave. I felt the same way. On moving day as she called it Janis caught us going at it again and stayed to watch.

If I thought April had taken me to the stars and beyond Janis did everything, she could prove me wrong. I guess she'd been inspired and was a bit jealous of April's and my developing relationship.

Janis loved riding me cowgirl style with my face buried between her beautiful mass of soft breasts. I learned in two weeks more about pleasing a woman sexually than I had in my whole life. Janis loved to be awakened by me using my mouth on her well used lower lips before we fell asleep.

Between the two it was April who I was drawn naturally too. I learned that she was seven years older than I was. It took about six weeks for me to realize that she was made for me. The only time I felt complete was when I was buried deep inside of her. That's how fast her warm heart, hot body, and open-mindedness had consumed me.

The way she used her lower virginia muscles to taunt me drove me wild. There was nothing more beautiful to me than seeing her sparkling eyes light up as I woke her up with my morning wood buried in her. April had proved that she was created for me to make love too over and over again. Although we fought it, we soon discovered the more we made love to each other the more we wanted.

I stayed on base for the weekdays and came home for the weekends. Believe me, I needed the rest. Both my dad's wives kept the boathouse clean and me well satisfied. Janis was the first to learn she had successfully been knocked up. Dad (Jack) was thrilled to death about it. He had told me that it would be a family secret and I had agreed.

I came home one weekend to find April had moved all her clothing in. I wasn't surprised as dad had come down to the base to talk it out with me. He had proposed to Janis and she had said yes and as a result, they were going to become exclusive with each other.

I asked him about Janis wanting to have more children. He told me that when she was ready that would be the only exception to their agreement but only until the desired result was achieved.

April, he disclosed had by accident had fallen madly in love with me. Dad asked me how I felt about that. I told him I was thrilled because I felt the same way. Together we went out and picked out April's engagement ring. Jack paid for the ring set because he wanted me to know that he was giving us his blessing going forward. After making love to her twice on that Friday night I slid the ring on to her finger.

In celebration of our new relationship, we spent the weekend in bed. I learned she loves being fucked in the shower from behind with her breasts bouncing freely as she was bent over. I went back to work early Monday morning dragging my ass big time.

It was during that time that April and I decided to go on a high protein diet to help us keep our basic shape in our middle years. To celebrate that agreement April decided she would have to have a protein shake daily.

I watched in amazement as I stood behind the kitchen Island as April pulled my blue jeans and underwear down. She knelt drawing my softness into her moist mouth while her hand began teasing my balls. I watched her as she worked her magic until she had my knee's buckling from the pleasure, she had given me. To this day I never know when she will decide that it's time for her protein shake. It's become one of her favorite games. The worst was when she was in the labor room at the hospital just about to bring our first into the world.

******

Katie arranged to meet me at Scallywags just a couple of days before the divorce was to be completed. I had stopped in on the way home that Friday night. She wanted me to drop the suit against her lover and the dinner club. It seems her boyfriend's cash flow had been hit hard.

I guess the high society snobs didn't like the publicity my suit had caused. Anyone who had worked for the dinner club was having a major relationship problem. There had been a rush on dna tests according to the local news. It was getting so bad that the casino was talking about canceling the executive dining club's lease.

Miranda came over and said to Katie, "What in the hell are you doing here? I know we're not a high society joint where snobs and sluts like you are used to."

"Trying to save what's left of my life," Katie replied. "Tom and his friends have caused a lot of problems."

"So, you're saying it was Tom's fault that you went after black cock," Miranda said. 'Is the going rate for slut's like you still twelve hundred a night."

Katie's face went white. That simple fact explained so much about my parent's relationship growing up. My mother when money got tight had been selling her services. It also explained why she was not concerned with money and had agreed to give me half so fast.

"Katie, I think its best that you leave," I said. "If your boyfriend can afford the nightly fee, he will have no problem settling the court case out of court."

Miranda brought me another round on the house, that little flair up with Katie had made her day. I told her I had to slow down on my drinking because I had better things to do.

Miranda smiled and winked, "I hear April and you are trying to make two before you set the date. Is that true?"

I guess Miranda got the answer she wanted from my face because she broke out in a big assed grin.

"Congrats Tom she is a keeper and will be as loyal as they come," Miranda said. "I'm in love with her younger brother who is just a little older than you. It won't be long until I get my ring too."

Just before I left, I leaned over and whispered in Miranda's ear "Are you wearing out April's brother as much as she is me. If so, you might want to stock up on Viagra."