Jail Breaking

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The sad tale of a man who learned too much.
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RichardGerald
RichardGerald
2,886 Followers

This is a story nothing serious and couldn't find an editor. Not much sex, no cuck and no BTB. Just another sad tale, but a warning the narrator is not necessarily telling the truth and his views do not necessarily reflect the author's.


The object in my hand is small and seems entirely harmless. It is less than five inches long, a little over two inches wide, and about a quarter inch deep. A mostly plastic object it has a glass face. Inside it has a set of microchips to perform its allotted functions. An apparently innocent object and yet the greatest threat to personal privacy the world has ever known. We call them cellular phones and we carry them everywhere voluntarily for anyone who chooses to spy on us. George Orwell seems a dull prophet when you view the current reality. Twenty years ago they were a novelty. Now we see these little toys as a necessity. The world changes even though we sleep.

I know what you are thinking, "there are rules and built in protections." But just consider the device in my hand right now. It belongs to my wife of more than nineteen years. She has never been anything, but loving and supporting. She is the dominant spouse, but no shrew. For my part, I believed in the sanctity of marriage. A commitment made and not to be broken. I was sure we would grow old together and that she would hold my hand on my death bed. I made a bargain so many years ago. I traded my youth and freedom for the pleasure of her body next to me in bed. I swapped my life in trade for her love and devotion. That commitment with me is stronger than any steel bars. I am not some romantic idiot, far from that sort am I. Marriage is something I take seriously. It wasn't about love on my side more an act of rational judgment. Doris, my wife, is the romantic, perhaps that is the problem an ancient incompatibility finally coming to light.

Here I am with my wife's iPhone at 2 a.m. in the little downstairs study we normally share. I borrowed the phone from the table by her side of our marriage bed. It is the only time it was available. She never leaves it out of her possession. She like most modern day women goes nowhere without her phone. She spends more time on it than any other single activity. It is within her reach twenty-four hours a day. It is in her purse or carryall when not in her hand. It is there by the bed when she sleeps. I had to wait until I was sure she was asleep to snatch it.

"Why take her phone?" you ask. I wonder myself, am I losing my mind? How can I suspect my loving wife? What is the matter with me? I blame it all on my occupation. It has stunted me made me suspicious. I see only the dark side, the evil men do, not the good. Put directly, I am an attorney. There but for the grace of God go you. So I suspect her without good cause or substantial reason.

It was a little thing. I walked into the kitchen while my wife Doris— actually Deloris but no one uses her full Christian name— was talking on the phone. On all prior occasions, she would have continued ignoring my presence, but this time she hung right up and seemed nervous. Later that evening I asked to borrow her phone to call for the pizza that I had persuaded her to have for dinner. We no longer have a house phone a little economy when the girls went off to University part of a lets save money any way we can strategy. She is against takeout food normally being extremely conscious of her weight, but tonight she gave in easily and easily handed over her phone. Why not, she had cleared the phone log and the text messages. She no doubt being a lay person thought this a good idea, but it was not, in fact, it screams deceit.

I am suspicious because clearing the log is an attempt to hide, so what is she hiding? That is what I need to find out. I am reasonably well informed, and I know it is easier to bug a cell phone than a more traditional phone. Don't believe me go on the Web and type in "BUG CELL PHONE" and see what comes up. I even got a nice little book at Amazon for $0.99 that explained all the basics. The big problem on the IPhone is the JAILBREAK. What's that? Well, it is the need to alter the basic Apple operating code, so it permits you to install non-Apple software. My loving daughters broke the software lock of their mother's phone when she first got it. The girls were rather proud of their ability to do this.

With my wife's phone in one hand and the little cable that connects to my iPad in the other I hesitate. Is this who I am now, do I want to do this? Dare I do this? The reality is this could end nineteen years of marriage, a very good marriage. Why am I looking for the exit? We are a happy couple. There is nothing I can ask of her she will not do for me. On the other hand, she rarely asks anything in return. I was reluctant to enter our marriage, but I have never regretted it. I guess I should explain that.

I'm David P. Landon, Jr. I was at a frat party. Now forget everything you know about fraternities. The brothers of Sigma Chi are the fraternity that doesn't fit the mold. They were the largest fraternity on the University campus because all you needed to join was a good heart. That's right, the brothers respected neither money nor position. It was all about brotherhood and doing the right thing. Jocks mixed with nerds, the academic stars with the guys permanently on probation. It was not uncommon to see a group drinking beer in the basement while an extended tutoring session took place upstairs for the brothers who needed help. All races and all religions mixed together we were brothers. All you had to be to be one of us was to be a good man. Sounds easy, but it's not when you failed to meet the standard you let everyone down. The guilt is the hard part, knowing you have let your brothers down. Being a Sigma meant all the responsibilities that went with being a good brother.

The annual freshman mixer was one of those responsibilities. The older brothers were the chaperones. We invited every frosh male and female. The females to get the males there so we could get an early look at the potential brothers. More women showed up than men because as everyone knew you were safe at the Sigma house we were all gentleman. I was a 'second year' law student and normally well insulated from campus parties, but it was my turn along with nine other brothers there to supervise the frosh. It was a responsibility if you are a Sigma you don't duck responsibility.

Doris came to the party with her girlfriends. I do not know what they were on, but they were pretty happy when they arrived. I recognized her of course she was the oldest daughter of my mother's best friend. When I went off to university, I was not yet eighteen. Doris was a skinny flat chested kid. I had seen Doris on a number of occasions since, but my memory of her was tainted by the earlier recollection. In my mind, she had remained a child. That was no longer the case, she was a curvaceous young woman although still exceedingly young—but definitely more woman than girl.

I had little choice but to go over and say hello. Doris was six years younger than I, as were the friends she was with. My intent was to say hello and leave it at that. She was high on something I hoped it was only marijuana or alcohol, and I didn't want to embarrass her. Doris greeted me with enthusiasm and planted a big kiss on my lips. She was always welcoming and a pleasure to be around, but it was clear that she enjoyed showing me off as the older student she happened to know. The fact that I was a fraternity member and one of the official hosts was a bonus for her.

I ended up watching over them all evening and driving them home after the party. Doris took the opportunity to wrangle a date with me for the following week. We hit it off and dated until the end of the term nothing serious. She was a freshman, and I was a graduate student, so it wasn't a serious relationship at least not on my part. She broke it off. She wanted to see other people. At the time, I was ok with it, but quickly became depressed. I seemed to miss her. I wasn't sure why, she wasn't beautiful in the classical sense. She had that young girl fresh and innocent look. She was petitely cute, at five foot four and maybe a hundred and ten pounds. There was nothing spectacular about her appearance, but one glance into her soft brown eyes and I was hooked. It wasn't love on my side more a deep attraction. Doris had a great buoyant personality when she was gone she left a big hole.

I am smart—no make that shrewd—but introverted and a bit shy. I tend to turn in on myself. Doris is outgoing and will if given the chance make friends with everyone in the room. She is the first person everyone invites to the party and the last they want to see leave. But she broke up with me to see other guys. I accepted that. I was hurt, left with a battered ego, but that is what breaking up does to you.

Fast forward and it is July following my second year of law school. I needed a summer clerkship. Summer employment second year is a virtual necessity if you are to graduate with the prospect of a job. I looked in New York, Chicago, Washington and every major place for anything but so did everyone else. I finally found employment in our sleepy little university town with an ancient law firm that specialized in Eminent Domain— I will explain what that is in a bit.

The apartment, I shared with two others, was rented only through June. I needed to arrange summer housing, fortunately, the University opened a dorm for the summer school students, and they needed a resident assistant, a responsible older student to act as a surrogate parent. The rent was free in return for being available as needed. It worked for me, and it meant the meager law clerk salary could be put to some better use.

Doris was going to summer school, and she was in the dorm I was supervising. I did everything I could to avoid her until one day I was going up the stairs, and she was a flight ahead of me. As I reach, my floor Doris was coming down the other way. Rather odd I thought except she came to block my way up.

"I want to talk," she said.

"About what," I said trying to move past her.

"Us and what a really stupid thing I did."

As it turns out, she regretted the breakup and was completely contrite. She asked for a do-over. I wasn't sure, but I saw no reason not to start casually dating and holding my emotions in reserve.

Doris was not playing around this time she pushed me. Her birthday is August 15, that summer she turned eighteen and when I asked her what she wanted for her birthday she said:

"I want you to make love to me. I am a virgin, and I want you to be my first."

I was astonished we had been doing everything short of oral and intercourse, but I was not prepared to go further, and I told her so. She was not taking no for an answer and as became the rule over the many years we have been together what Doris wants Doris gets. The day after she turned eighteen was a Saturday. Doris was a volunteer at the women's shelter run by the local NOW chapter.

Early Saturday morning Doris went off to help at the shelter. I had no idea what she did there, and the location was a secret. She didn't have a car, so I was to pick her up at the student union on campus about four p.m. It was a good walk from the dorm we were sharing for a few more days. The new fall term was due to start in ten days, but we still had a few days left in our current dorm rooms.

The Union was a big oversized coffeehouse/cafeteria in the center of campus. At four p.m. on a Saturday it was not very crowded, but it was never empty. When Doris appear she was in jeans and a NOW t-shirt, but she was carrying an overnight bag. Unmistakably we were spending the night together, but why walk around with a bag since we lived in the same building at least temporally? As Doris and I came together in the Union, she gave me a big deep passionate kiss. She was proclaiming to the world or at least to the Students on Campus that we were going to have sex. She was making a statement. But what was the statement and why were we telling the world what we were doing?

We entered my dorm room. As RA, I had no roommate it was just us. I lit candles and had a bottle of Champaign good stuff, White Star. She was nervous as hell, and I was very little better. I am no Don Juan. I had been with exactly two other girls and neither for more than two nights. Doris was putting a lot of pressure on me.

We drank a bit then I slowly undressed her. I started exploring her body with my hands and then my lips. When I had her good and hot, I stripped for her. When I pulled my shorts off and threw them at her, she giggled, I was rock hard. But before I could go further she stopped me.

"I need you to help me with my spermicide," she said.

"I thought that you went on the pill," I replied.

"I did, but it is not 100% particularly in the beginning, I love you David, but I don't want your baby right now," she said.

In the middle of my seduction, I was filling a plastic cup with foam and inserting it into her vagina. Then she depressed a plunger to shoot spermicide into her womb. In all respects, it was a very unsexy experience. From this point, Doris took over she had spoken to other women about this, and she knew how things were to progress. I needed to go down on her. I was reluctant as we had just put foam in her vagina.

"I don't want you there but up here at my clit," she indicated.

I was more game than I thought. I went down on her. In two minutes she was almost there, you could tell by her moans and breathing. I stopped and spread her legs. I pushed into the tightest and hottest cunt I had ever known. She was a furnace, and I had barely got in when she screamed and came violently on my cock. She drenched my bed with her come. As I pulled back, she grabbed me and held me. Thus began the strangest sex of my life till then. She gripped me with a passion the two who came before her had not. The sex became a kind of battle where I could not tell whether I was fucking her, or she was doing me. It took me twenty minutes to get off, and I think she came five times to my one. But we had just begun, Doris had the night planned.

Thirty minutes after the first bout Doris sensuously cleaned us with a damp cloth and then proceeded to take my reviving cock into her mouth. She had me hard quickly and then mounted me, thus began a slow fuck that seemed to go on forever.

"This is not what I would expect from a virgin," I said.

Laughing she said: "I studied up and asked questions, I wanted to make this perfect."

"I'm so excited," she said, "it all so new and wonderful."

The bottom line was that Doris was beyond good. Sex with her was a life changing experience. She loved it and couldn't get enough of it, and she was not afraid to show her enthusiasm. With Doris, I learned to relax and enjoy sex, this was a thoroughly new experience for me. What I had before was not even a pale imitation, but bedding Doris wasn't heavy or intense. Doris made the sex fun. The sex was frequent, but she made sure I kept it in prospective. The serious part the relationship between us was our being together as a couple. I should have taken note, but now I was hopelessly in lust with this young woman. Doris knew it and was soon using sex with me to get what she wanted which was a boyfriend she could wear like a new winter coat. We went everywhere together, and Doris left no one in doubt that we were a couple. I had never been part of a true couple before and found that I liked it. I guess I was what they referred to as a one woman man.

Doris decided it was time we disclosed our relationship to her family, which consisted of Margaret and Lawrence Boswell, her parents, a younger sister, Maryann, and little brother, Larry, Jr. They were a well to do family. Larry, Sr. was the Senior Vice President at the Shamont National Bank and Margaret taught at the Shamont Community College. They were an attractive and impressive family. They treated me like royalty. They were impressed with my status as a soon to be third-year law student. Moreover, her mother Margaret came from money she was a Shamont. She had gone to high school with my mother at the Sacred Heart Academy for girls. She went into teaching while my mother went into nursing.

Margaret Boswell was an exceeding attractive woman. She is taller than my Doris and not as voluptuously built, but she has a patrician grace about her. She had that stately beauty which ages well. Her husband was a tall silver-haired businessman who looked great in a suit, but had developed a little middle age spread. He looked older than his forty -five years in contrast to his wife who at forty did not look thirty- five. The younger daughter Maryann at sixteen had just begun to fill out, but appeared to be taking after her mother in stature and appearance. Little Larry was only eleven, but tall and showed the promise of the hefty build he would eventually have. He and I were to become great friends to the point he is now my best friend.

My folks loved Doris long before we started dating, so she quickly became a de facto member of my family. Even my kid sister Paula was a Doris supporter. My brother was too young to have an opinion. My family was not quite as well off as Doris' family. Dad, David Sr., runs the family equipment rental business with my uncle John. My uncle is the older brother by ten years and a bit of a tight wad. The business does well under his strict management, but it is my Dad's outgoing personality and his ability to make friends and work with anyone including people he hates that has truly built the business. My mom needed to work because the business is a modest money maker, and my Uncle is very conservative with profits.

I am very close to my mother Agnes a tall good looking woman who at Forty- one was eight years my father's junior. She like I tower over my five foot four father. Mom's most spectacular attribute is her blond hair, these days it gets more than a bit of help from her hairdresser. She is a registered nurse who regularly worked nights. She was on a four-day a week work schedule when I was a kid. It was not the same days each week it rotated. That's how it was while I was growing up, but through the years she earned a master of nursing degree and is now the head nurse in the hospital where she works. She always needed to work, and she brought in as much or more than my father in income.

My relationship with my dad is more complicated than with my mother. My Dad has always tried to get me and my shy introverted personality to open up. He is a friendly outgoing guy who seems to know everyone and who believes in getting along with everyone. Dad believes in turning the other cheek and would never start a fight if that could be avoided. He and I don't see things the same most of the time, but he certainly approved of Doris big time.

"That's the girl for you, son—she is smart and good looking like her mother."

As a kid, my favorite thing would be to wait up for mom if she were working four to midnight. Dad would let me stay up on Friday and Saturday nights, and then I would babysit my siblings while he went out to pick mom up from work. They brought home burgers and shakes, and I would indulge in these with my parents. Some weekends Mom came home alone very late, and she would kiss me goodnight as I lay in bed before she went to shower and go to her bed. When she would lean over, I would on those nights catch the scent of her perfume, Chanel Number 5 which she wore when she got dressed up. I would wake sometimes to hear the shower going and then the whispering between my parents followed by my mother's distinctive laugh before their bed would begin to creak. It was a loving home even when business was slow, and money got thigh and Mom took on more hours.

RichardGerald
RichardGerald
2,886 Followers