Chapter 19

The next day at school I grabbed Karl the minute I saw him, "You and I are having a big talk at lunch about Connie!" I was really pissed about him trying to do Connie with out asking me and or behind my back. With just a few weeks to go till end of school we could sit outside during lunch.

"Are you mad about that Connie?"

"She ain't that Connie, she's my Connie! She sure as fuck isn't your Connie. I pay her, she works for me. I told you she was mine and you go try that shit."

"I didn't mean anything..." My dad had already told me when anybody ever starts with; "we were just having fun, I didn't mean anything, can't you take a joke, : and so on you could immediately tell that they knew they were wrong, the other one he used to laugh about was "It's not about the money" when it starts with that phrase, IT'S ALWAYS ABOUT THE MONEY! Dad was always pointing out both visual tells and verbal tells on people all the time. He always said, business was a lot like poker.

"Bullshit Karl, you were trying to fuck something that belongs to me and you were trying to sneak it! I thought you and I were going to swap moms, that still sounds like a lot of fun to me, but it ain't going to happen until you and I swap your mom for my Connie. Now Connie will do what I tell her to do, when you get your mom to that point, let me know and we'll get together. Until then stay the fuck away from Connie. You go for Connie again; I might just have my dad make your mom a job offer she just can't say no to!"

That put a little strain on our friendship to say the least, I tried to tell Karl that we were still friends, just not as good friends as we were last week, we left things up in the air. I wanted to fuck his mother but more as a training exercise for my mother. To become completely mine she was going to have to learn to eat pussy and fuck other guys, I thought it would be best for her to start with someone she knew and the woman a casual acquaintance. I wanted mom to think of eating pussy as something she did to please me rather than some lesbian thing. The same with fucking other guys, she should learn that her fucking somebody else was OK if I said so. With a little work, mom should be the kind of woman that sucks some guys cock and looks to me to be sure I'm enjoying her doing it. So, if not Karl's mom perhaps Connie had a friend or hell even Mrs. Olson! Somehow though the idea of two or three sons bossing and degrading their mothers as a group activity was a big turn on for me.

I was working one Saturday at the feed mill when I overheard a couple of farmers talking about some strangers driving around the countryside. The farmers figured they had to be USDA but I hadn't heard anything from dad about any investigations or problems. I mentioned it to dad and on Sunday he invited the sheriff and his wife over for Sunday dinner. Mom was a little pissed about no notice, but a chicken will feed five people and potatoes aren't that hard to cook. After dinner, dad took me and the sheriff into his study and told him about the strangers. It was decided it would be a good thing if the strangers were brought into the office for questioning. Dad told the sheriff, "If it's what I think it is, don't let your deputies talk to them, you find out who they're working for and get me some names and phone numbers. Now you keep real quiet about this, get your most trusted guy to pick them up. If this works out, you aren't ever going to have to run for office again"

Within 10 days we had the story pieced together, there was a big Japanese car plant going to be built somewhere down south. The strangers were advance men looking over various plant sites. Dad talked over the project with me. "If we go for this plant we'll be real rich, but we'll never control the county the way we used to. I don't think I'll have any trouble getting our people elected in the next cycle but after that there are going to be a lot of newcomers here and who knows? You know that camp up by our lake, I've been thinking about developing the whole lake as a private hunting and fishing preserve. This new factory would mean a lot of new roads, we can get a bond issue for that and build one of the highways near to our property, you know how it is now, the trip's almost 3 hours in 4-wheel drive. With the new road, we can build our own decent access and put in some high dollar rentals and condos. With that in place we can move out there and not worry about who runs the county in the future."

When I asked about why move out of town dad told me that even though he and grandpa had tried to be fair with people, you always made enemies when you had a lot more money than everybody else. Of course, we could just move to Chicago or New York and live off the investments, that's probably going to be your decision as ... There really wasn't anything to say, we all knew dad's prognosis.

We set up a little honeytrap for the real estate scouts, Connie and Sally picked them up in the bar at the hotel and it was no problem to have the spy cameras running by the time they brought the girls upstairs. Watching the tapes later was a little shock to me, if those two were faking for the real estate guys they were faking for me too! It never hurts to be reminded that you're just another guy, when you're humbled, you try harder.

Anyway, by this time Mr. D had done a background check and both guys were married with children. Two nights before they were scheduled to check out, dad, Mr. D and I made a house call on them. I was impressed as dad laid out their options, we wanted a most favorable report on our plant site, dad showed them on a plat map where the plant should go. Otherwise he would have to sent the two tapes off ; and then he really put the heat on them, naming both home addresses, names of both wives, names of churches they belonged to, and as a kicker, he named their children, think how little their kids would have after a messy divorce?

As dad was talking, Mr. D had opened a briefcase and laid out several Fed Ex mailers the size of DVDs. Then dad put one DVD in the room's combo TV/player and as it was playing, turned the sound down. "Now all we want is a fair and full evaluation, of what a great site we have here, I can guarantee the full cooperation of both the town and the state. In addition to you receiving all copies of these tapes there would be a cash bonus of 25,000 each the day the plant site is announced. My associate Mr. D here would deliver it in small unmarked random numbered bills. If we don't get the plant then Mr. D would be honor bound to deliver these tapes to your family and friends; by the way, if you watch to the very end there is a section where the mother complains about her daughter being under age and accuses you two of doping the two of them. Think it over; you know this is a good deal for your company you get some extra spending money, and when ever you're in town I'm sure we'll be able to find some proper entertainment for you. The Fed Ex pickup is at 10 AM tomorrow let us know by then."

Of course they called and said they would do all they could to help. Dad was really not feeling well, but we flew to both Chicago and Cincinnati and I got to meet a lot of bankers. Dad had explained that I was to just listen and if anybody asked me anything, my best answer was that I was there to learn, not have opinions. The conversation was all about options, leases, mineral rights surveys and plat lines. At night, in the hotel dad would explain how he was going to have over 10,000 acres available for this new plant and the various sub manufacturers that would spring up around it. He went on to say that the land for the auto plant would almost be a give away but the money would be in all the surrounding areas. For every dollar we give to the japs, we'll take in $20.00 on the other properties. Some properties would be outright sales but he and the banks were planning three separate industrial parks with leased facilities. Our construction company would build the buildings and sell them to our industrial parks and the parks would lease them out to various manufacturers. That way we can make money a couple of times on the same piece of property! When we got back from the trip, dad went to bed for two days, both mom and I were scared but as she said this is what he wants to do and if he dies doing it, at least he'll go happy.

I got back to school with just a week to prep for finals. With Marty's help I did pretty good, a couple of B's and passed everything else. The week after graduation I was at the girl's house as we had the big unveiling about who won our bed bet. Janie stunned us all by winning everything not only top grades in the house, but top grades in her class! Even more important to me was that Kathy had done very well at her school, she was typing at almost 60WPM and had got an A+ in her bookkeeping course, and I brought up the bottom so of course Janie zeroed in on me. Like I said, it was a bet I couldn't lose. She had her mother and older sister lick on her boobs while I had to go down on her, then I had to finish inside her while the other two kept up on her tits. As I came up for air to put my dick into her, I was sp turned on by the sight of her mother really into making love to her daughter's boobs. You couldn't fake that look that said mom loved sucking her daughter's tits. Then Janie almost had me cum before I was in her. "Mom, you spread my pussy, Marty, you put Mike's dick in me, then you two can go back to kissing my boobs."

As I moved into position, I loved how both her mother and older sister scrambled to obey. Kathy had a big grin on her face as she slid down to put a hand on each side of daughter's pussy and gently pull them apart. Janie was ready; I could see all the way down to her cervix when mom had her spread, not only that mom had her daughter's clit between her thumbs and was rolling it around. As Marty was grabbing my dick, she laughed and said, "This won't hurt a bit." Then she waved my dick up and down rubbing her younger sister's puss with the head of my dick.

"Put it in! Now!" I was pushing, Marty was holding me back.

"Say please!" Marty laughed

"MOM, make her..." and with that Marty let go and I slid into that soaked young pussy, mom moved her hands out of the way but not before she gave me a quick squeeze. As erotic as this all was, a mother holding her daughter's pussy open for me, her sister guiding my dick; the hottest thing to me was the look on Kathy's face. She loved what we were doing! All around her mouth was wet from her sucking her daughter's tit but her eyes were alive with love, love for me, love for her two daughters and love of this wide open sex life we were having. I would have married her right there, just for that look! This was sex without sin, on a good day I almost had that with my mother, Connie was close to that ideal; but Kathy and her daughters were without guile, they enjoyed sex, they enjoyed sex with me more than with somebody else, but they really enjoyed SEX. And they showed their enjoyment in thought and action, their attitude towards sex was something like a child with an ice cream cone on a hot summer's day; it was good, it was fun, and can we have another please!

I can't say I gave Janie my best performance, the presence of her mother and sister was too arousing but I did the best I could, it seemed to work as Janie was not intimidated by the presence of her family and come and come again, she did. After supper we had another round robin with Jamie as the center piece, if you'll pardon the pun. Nothing would do that Jamie got to sleep alone with me that night. As I lay there listening to a well satisfied Janie sleep it occurred to me that she was really too young for my tastes. I know that I would be marrying someone about Sally or Marty's age but my heart was happiest with their mothers or my mom. The only edge that I could see that teenagers had over women in their thirties was a trim and tight ass. But I wasn't in love and could afford to pick and choose among the women I met. Just before I fell asleep I was wondering, am I the only one who doesn't dig young girls, but hey, I don't like the porno gals described as 48dd knockered love machines. Nope, give me a woman 30 to 50, trim, well dressed, educated, refined, preferably wearing her grandmother's pearls; and let me fuck her in the ass and cum in her mouth til she calls me daddy! That's what I want out of a relationship. And with that happy thought, I drifted off to sleep.

I was woken from those beautiful dreams by the harsh reality of a teenager pulling on my dick and biting my earlobe while she snorted in to my ear. Once she saw I was awake she stopped chewing on my ear to whisper that she wanted me to ass fuck her. I told her we should wait a year she was too small, but she was adamant. I finally got her to compromise that we would stop if it hurt too much. She grabbed a tube of lube, I guess they were all over this house, and with a giggle she flipped over and stuck her ass way up in the air. "OK calm down and lower your butt a little." As she came down to almost a normal ass height I started working on lubing her asshole. The first thing I did was lube the nozzle on the tube and after a couple of circular rubs I slid the nozzle into her ass and gave a pretty good squeeze. Jamie jumped, and now I had my finger well lubed, I was gently rubbing her asshole and occasionally pushing against it for a couple of minutes, then with a fresh application of jelly I slide my index finger in a little past the first joint. I didn't have to hear Janie's choked off cry, has asshole was tiring to cut off my finger. I swear you could crack walnuts with that pressure, hell maybe even Macadamias! "You, OK?"

She choked out a very small OK and asked if we could not move for a minute. This may sound funny but a minute is a long time to not move a finger inside someone's ass. I mean, it's not like you can do something else while you wait! I finally started just flexing that one joint that was inside of her. I looked at her face and could see she wasn't very comfortable. I pulled my finger out and started to massage her cute little butt.

"No, put it back, I'll get used to it, I can take it." More jelly and less pressure this time, I did get in deeper, all the way up to the second joint. By now some of the pressure had dropped and I was able to slide my finger, in and out of her, very slowly and very gently. As I was doing that I actually saw some of the tension leave her, her back started to resume its natural curve and her breath became a little deeper. But when I tried the second finger we reached a road block, although Janie wanted me to go ahead, she was in such discomfort that I couldn't watch. I told her I didn't care what kind of welsher she called me; I wasn't going to fuck her ass today, I'm not going to cause you that much pain. I'll tell you what, I'll send away for some anal stretchers! You can go at your own pace. When you get to the point you can take me without it hurting, I'll take you to a hotel, with room service to celebrate. You would have thought that I had promised a 6 year old a puppy for Christmas. In no time I was being sucked up to Mach 3 and then Janie had to be fucked dog fashion. For all I know she may have been hoping I would slip and shove it up her ass. As it was she got a great fuck because the whole time right up until I came I was watching for her to try to slip my dick in her ass. Breakfast was the usual erotic mess it always was at their house, After cooking, Kathy took off her apron and I was trying to eat with 3 pair of boobs bouncing all over the room. As I was going out to the car I told Kathy about her youngest needing to be stretched because she wanted me to butt fuck her. Kathy laughed, "She and I had that talk, I told her she had to get a little broader across the butt before she could handle a cock in her ass. OK you get us a set of very small to medium butt plugs and we'll start her on a training program. I'd rather start her myself, for fear she'll hurt herself otherwise. In a lot of ways she is still a little girl who wants to grow up now! She sees me and Marty getting off on a good butt fuck and she thinks why not her. I'll talk to her, you go ahead and order those, just make sure they're the smallest they've got, all right?"

Over the next couple of weeks, dad was out of town a lot, he was 100% committed to this plant idea, some of the trips I was invited, others I stayed home. Whenever we were alone dad would keep telling more and more not only about the existing businesses but business in general. I was getting a cram version of the Harvard Business School! The home stays were nice because I had mom. Well sort of had mom, some nights we were lovers, others she got me off and sent me to my bed. A couple of mornings were just great; we'd be sitting at the breakfast table like a married couple. Mom would have a robe on and she made me wear shorts; but the atmosphere was one of what I guessed old married people had; a relaxed love filled the room, and twice we got up from the breakfast table and went back to the bedroom! Those were great moments for me. But then that standoffish crap would start again and I'd be in bed pulling my dick.

Dad was not looking good, the strain of the traveling and the planning was telling on him. I overheard mom and him arguing, she was saying, you don't have to kill yourself for a few extra dollars and he was talking about the empire he was building here in this state. The very next day he took me down to the walk in safe in the basement and after locking us in: showed me another safe hidden behind a file cabinet. When he opened it he showed me a whole stack of envelopes, each labeled with the name of one of our companies, there were a few in the back that just had names on them. He then explained this was all basically blackmail info, hell some of the people may be dead by now, anyway each envelope has dirt on somebody in that company. The envelopes with just names are politicians, lawyers, wiseguys and misc. assholes. Don't look at that stuff unless somebody is squeezing you hard!

Well with the travel and the stay at homes I had to make a special trip to see the girls to confirm to them that there was nothing wrong, it was just real busy. I still had a once a month with Connie and Sally and that usually netted me at least a blowjob.

School was out by now and I got a call from Karl, "Hey, we still friends? I never see or hear from you, is everything OK?"

I decided to see if I could motivate Karl a little, "Oh yeah, everything is fine, my dad's been working me real hard, Between my mom and Connie I just don't seem to have any spare time."

"Well that's sort of what I called about, you got a minute?" He went on to tell me how he had been talking to his mom and she was willing to try sort of a date with me. But she wouldn't promise how far she'd go. Would I be pissed if she chickened out at the last minute?

"Karl, let's try to stay friends here, I took you over and introduced you to a woman who did both of us, you know the type of women I like and you know that I expect them to have sex with me. You tell your mother that, yes we can go on a date, and yes she can say no. What she can not do is say no at the last moment! She can say no at dinner, she can say no, while we're in the car; where she can't say no is after we go in the door at the hotel! That's unacceptable! And you better understand; if your mother says no, Connie and I will be leaving and one last thing, I can get the suite at the hotel but you and your mom will be responsible for any room charges and that includes the mini bar and the phone. Now you go tell her that..."

Karl broke in," Man, how can I say that to my mother, she'll..."

"Karl, you just tell her, you tell her that she is your woman, and this is what you expect from her! If it works out with Connie, I'll fix you up with my mom; she does what I tell her to do! Hey, if it doesn't work, no problem, you've still got your mom and I've still got my mom and Connie. Look, got to run, let me know!" As I hung up, I thought, why break Karl's heart by telling him about the girls.

It took two weeks for Karl to call me, he swore up and down that his mother fully understood what the rules were and she promised she would abide by them. I checked with dad and he said I could use the suite. I called Karl and told him Connie and I would pick them up at 6 PM next Saturday. Tell your mom, I expect to see a good looking woman showing some cleavage and I promised Karl I would supervise Connie's outfit.

When I picked up Connie I was pleased to see she was wearing one of the man eating outfits. This one was in a soft heather green/grey and almost looked like an office dress, and then you noticed how much cleavage you were looking at, and not just down the center but it was a wide cut Vee, that exposed quite a bit of slightly pushed up boob. The skirt had a front slit to it that was unseen until it was walked in. then it was as if the skirt alternately exposed each leg to mid thigh. All in all, one hell of an effect! Sally was a little upset about not being invited but I just shut her up by saying that this is business; yeah, the business of making me happy. On the way over to pick up Karl and his mom, I made sure that Connie knew that tonight was all about turning Karl's mom out. By the end of the night, I want her sucking my dick and eating your pussy in front of her son. This goes right, there's an extra 200 in it for you.

"Mike, maybe I shouldn't say this, but you don't have to pay me for tonight, I'll be glad to do a favor for you, because of you, we're almost out of debt, maybe soon you can give me an idea of what to invest in. I'm not planning on retiring tomorrow but it would be nice to start building a nest egg."

"OK, I won't pay you but could I give you a couple of hundred to go see if they've got anything else at the dress shop you got that outfit from?"

"Deal" By that time we were at Karl's or should I say Karl's and Trudi's? We didn't get a chance to get out of the car when the two of them came down the walk. Connie got out of the car and blocked Trudi from getting in the back seat, Karl got a kiss on the lips from Connie and I got a hello and a proffered handshake as Trudi slid into the front seat. As I took her hand I managed to get a peck on her cheek, "So nice to see you outside the house, Trudi, I'm sure we're going to have a good time tonight." Trudi was looking confused and searching for conversation. I knew she was having trouble thinking of me as date meat; I was the kid that hung out with her son. Well, honey tonight you'll learn that if you fuck your son, you fuck his friends. Today you suck my cock; tomorrow you can offer me milk and cookies!

Connie started earning her new clothes, "Trudi, you've never been out with Mike, let me tell you he's a very nice guy. In fact he and your son are about tied for nice guy of the year awards. Trudi half turned to look at Connie and I got a good look at her clothes, simple white blouse, medium low cut, short skirt that showed a nice looking knee and thigh. Not what I wanted but I could change her style later.

We stopped at a nice quiet dark Italian place where I knew they would serve Kurt and I wine with a meal. A salad and a shared pizza with a liter of red and we were done eating in under an hour. Trudi started to say something when I poured wine for everybody including Karl. "No, No, not tonight; tonight, you're my date you're on a date and you do what your date wants, isn't that right Connie?"

"It is, if you want to get asked out again," laughed Connie. That little laugh, as small as it was, was the icebreaker for the night. I could almost feel Trudi relax next to me. I slid over the inch separating us in the booth and laid my left hand on her thigh. That widened her eyes momentarily but since my hand was resting on her skirt and I wasn't moving it she settled back down. "So Trudi, when was the last time you were out on a date?" I put some emphasis on the 'out' portion. She looked over at Karl, but he was busy listening to Connie or staring at that wide cut neckline.

"Oh golly, it's been three years, at least since my husband died."

"Well look, we're going over to a hotel suite that the company keeps, we have a private elevator so you can completely relax tonight. No one's going to see us coming and going. I'm looking forward to getting to know you better and I think you're going to like the rest of the evening. If you don't want to go, say so now, I'll take you and Karl home and Connie and I will go on our way."

"Oh we're going; Karl would kill me if we didn't! And now that I met Connie, I'm curious about you." And with that I got a kiss, not a big one, but a kiss on the lips! Every step in the right direction is a good step! And with that I looked over at Karl, he and Connie were going at it obviously tongues entwined. The poor forty year old waiter was looking at Karl and I wondering where he had gone wrong. Both Connie and Trudi were above average in looks, Connie had a better body but I like slender women so Trudi was fine with me. The waiter knew that Karl and I were under twenty one but this place was struggling to stay open and were well know for serving anyone; it wasn't the wine, he had to be wondering how we got these two to go out with us. I made a note that if I came here again, I'd give whoever I was with the money and let them pay! That would really fuck his head around. I left the poor guy a good tip; it didn't look like they were going to make the rent tonight.

We walked out to the car like two regular couples holding hands. Trudi was impressed with the concept that I didn't have to go to the desk to check in and I had my own key card. I had been up earlier and stocked the mini bar with stuff that Karl had bought. A bottle of Champagne, some canned cocktails for Connie and soft drinks for the rest of us, anything to not pay $3.00 for a fifty cent coke! We all grabbed a drink of something. Everyone knew what was coming but no one knew how to get there. We were all there to get laid, but no one was going to talk about sex while they had their clothes on and with sex on your mind, there just isn't much room for small talk.

"I'm going to show Trudi the rest of the suite, Connie, why don't you and Karl check out the other bedroom?" I was gently pulling Trudi into the larger of the two bedrooms. I wanted this one because it had the mirrored walls and ceiling. When Trudi saw those there was a real gasp from her. I turned her towards me and pried the bottle of water out of her hand. I pulled her close and slid an arm around her. "Take it easy we're here for the fun of it" I kissed her once, there was no resistance but there also wasn't any cooperation. The next kiss had a little power behind it accompanied with my hand sliding down to caress and pull her ass into me. That at least got her to open her lips a little. I pulled my head back a little, "Now that's better, let's try that again and see if you like it." She never opened her eyes but she also didn't try to pull back. This time I started the full exploration of her mouth and my hand was now firmly rubbing her ass, aha, her tongue answered. Just before I broke the kiss I gave her not a slap on the ass but something more than a pat. That got her eyes open. "You can look at me while we kiss and make love; I like a girl who takes an active part in the relationship."

With that I pushed her back until we were ready to fall into the bed. "Here, let's take these off, no sense getting them all wrinkled lying down." Trudi started to protest and I just decided to win or lose right now. "Come on now Trudi, we all know why we're here! You and I are together because your son wants to do my friend Connie. That's OK with Connie and it's OK with me, but part of the fun is you and I getting together. Now either enjoy the rest of the evening or let's go home right now." By now I had Trudi at arms length, holding her by the shoulders, "What's it going to be?"

She stood for a second and realized this was not the place or time for false modesty, she let out a little giggle and reached up and started unbuttoning her blouse. I let go of her shoulders and reached behind her for the zipper on the skirt. In no time Trudi stood before me in bra and panties, I was quickly striping myself. On the first date I always felt it was a little embarrassing to have one partner naked while the other is still dressed. After the relationship evolves I think it's important for the woman to be at least in her undies even if I'm in a suit and tie. The nudity, partial or total reminds them of who's in charge of the relationship. And as my dad once told me, if you can convince a woman you only are interested in her body she will do everything she can with that body to keep your interest!

As I stepped out of my shorts I pulled Trudi to me. "Well, let's see what we have to work with." Now we were really kissing, tongues and saliva flowing from mouth to mouth. For once I was able to rapidly undo a bra snap. I quickly slid my hands down her back to start on an everyday set of panties. If we were going to do this again, Trudi was going to have to do some shopping. After the panties were below her butt I released the lip that I was gently sucking on, and as I stepped back took her loosened bra with me; no matter how many times I see it, that move that woman have of curving their shoulders forward as they take off a bra is a turn on for me! I'm sure it's just the easiest way out of one, but it's a bell ringer for me. I only had a quick glimpse of her boobs as I sank to my knees in front of her to slide the panties the rest of the way off. As Trudi moved from one foot to the other I caught a whiff of perfume, she had dabbed her puss for tonight. Well, that deserved a kiss! As I held to her surprisingly firm ass and kissed her pubic hair she turned sideways and fell back on the bed. Ah, home at last. I stayed on my knees and threw her legs over my shoulders; there was that gateway to heaven! All pink and pleasantly wet, at least she was looking forward to this. My arms went under her legs and around to pull that pussy open, open to me and mine. A few kisses and licks along the lips as my fingers searched for the sometimes elusive clit. There we are! Not only could I feel it I got a nice little gasp of approval as my fingers started their massage. I gave Trudi five solid minutes of top flight pussy licking as taught to me by the girls and now it was my tongue trying to rub off her clit as I had two fingers working over the rest of her pussy. She slipped into cosmic joy mode as I played the Gene Krupa's solo from "Sing, Sing, Sing" on that bumpy little G patch.