Jake's Journal: Close to Home

Copyright © 2010-2014 by VeryWellAged

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Author's Forward: (please read first)

There are four threads in the Jake Universe. You are about to read the only that does not deals with the Philippines.

Though the first three, (The "Jake's Journals,") start identically, events move each thread in radically different directions. This version is only identical to the other versions through half of the first chapter. I have placed a Split where they diverge completely


There is nothing innocent about me, or what happened to me. I make no apologies for my choices or the results.

I was divorced for the third time in my life in 2003. I am not proud of that. Sad is the best way to describe it. Three times divorced is not a record any man should strive to achieve.

My first marriage was a fool’s errand. I was 18 and she was 17 and pregnant. She - we - got pregnant in July. We were married in October, the nineteenth to be exact, and our son was born in May. By the time he was eight months old, she was gone and so was my son. What happened?

Hell, I’d be lying if I told you that my memories were accurate. I have told the story so many times that I no longer know what is true and what’s invention. All I can be sure of is that she ran away with a drummer from a rock band. After all these years, I still remember his name. I will keep his last name from these pages – but his first name was Kenny. Within the year of her leaving me, we were divorced. That was in Vermont. I was twenty when I got the final divorce judgment. All I can say is that over the years, my assessment that she was clinically nuts seems to have been borne out.

It would be eleven years before I married again.

I had some short-term girlfriends in those long years, but for the most part, I was alone. There were a few intense relationships, each lasting about a year. Between each, there were years of true celibacy. I never learned to play the field or date casually. I was either playing with all my chips on the table or I was sitting it out completely. During those celibate years, I would wonder if my fate was to be married to my right hand for the rest of my life.

The failed marriage had left me feeling that I was not desirable; that I was incapable of attracting a truly desirable woman. Most of my relationships were with damaged women who had little to give me, and no way to grow into a healthy relationship. Why were they damaged? The reasons varied, but the fact is that I sought them out. I figured that with them I had a chance of getting lucky for a day or two. I didn’t give myself a chance with women who weren’t damaged. I didn’t try. Or… you could say with some honesty, I didn’t know how. In all honesty, maybe I still don’t.

My second marriage lasted exactly thirteen years. The divorce was granted by the court on our wedding anniversary. (The odds are 364:1 and considering 365 random things probably happen each day, it’s not as unlikely as you might think.) There were a few days of good marriage, followed by twelve years of hell. For the last few years, we slept in separate rooms and lived separate lives. I finally swallowed my pride/shame and admitted defeat. I left the marriage because it was the only sane thing left to do. It was that or continuing to live with a woman who had a hard time distinguishing her funds from the funds of others. Her first embezzlement had cost me in the end about ninety thousand dollars. When I left the marriage, she was playing fast and loose with federal funds and I wanted no part of it. The judge didn’t believe me and pounded me in the divorce decree.

Five years later, I married again. I thought I had learned from my past disasters, but that was not to be the case. We were together a little over eight years before I left the marital residence and seven months later, she filed for divorce. She was a good woman. Not nuts, not a thief, but damaged in other ways. Truth be told, was I not damaged? I was and am damaged by the events of my life. It is fair to say that the marriage just did not ‘take.’ It was both our faults. On my side, it was probably far too much scar tissue from my past experiences.

So there I was, overweight, with high blood pressure, and false teeth. I snored so loud that I bet you would have heard me if we had rooms next to each other in a hotel.

In many ways I was a good man, but for whatever reason marriage and I did not work well. Was it my entire fault each time? As you can tell, I think not; however after three failures, you have to question my ability to make good choices!

Could I get married again? Sure, I guess, if I married someone who I had no interest in, but what’s the point in that? The sad truth was that at this point in my life I was only emotionally responsive to slim, pretty women at least fifteen years my junior and, in truth, usually even younger. Considering all that I was, no one of such a group, who had her head on straight, was going to put me on her ‘A’ list.

Truthfully, I really didn’t want to marry again.

For the entire time I was in my three marriages, I was not rich and sometimes I was pretty poor.

During the entire last marriage, I was in a lawsuit to recover income and ownership that was illegally taken from me over a year prior to the marriage. Even though we got along OK financially, there was this big payday always hanging out there. It was still hanging out there when we got divorced.

I was fifty-seven. I had a house to live in. (I had never sold my house when I moved into my third wife’s home. That should have set off alarms!) I was alone, just barely getting by financially, and sexually starved. As much as I would like to have gotten laid regularly and frequently, there were no options.

Hell, for the first seven months back in my house I slept on a couch. I went through so many variations on how to set up the couch as my bed that I gave them version numbers. By the time the mattress I purchased finally arrived, I was on Couch v4.2-5. It actually worked quite well.

Family? I had a son age 39 and a daughter aged 37. Both lived in a different state. Though I loved them both very much, they had and still have little to do with my life on a daily basis.

I lived in a truly rural part of the American West. The kids lived in NYC.

Once the reality of the third divorce sank into my skull, I knew that I did not want another wife. I did not want, would not be able to find, a mistress; but needed the ministrations of a prostitute on a regular basis. While my need for emotional intimacy would go unmet, my need for physical intimacy might be met. There were only two problems: I did not know any prostitutes; I did not have the money to pay for one, yet. But that might change.

I just hung out; not quite a hermit but without anything going on either.

When the legal settlement finally came about, that was the state I had been in for a while.

The settlement did not leave me filthy rich as some got to be in the “dot com” boom of the nineties, but I was now financially secure. In addition, I was still working and drawing a salary. I could easily afford a prostitute. I figured I would allocate two thousand dollars a month for whatever that would get me. The rest I would invest. As I was in a rural area, I had no idea how much those dollars would purchase in services, assuming there were any services to purchase.

Finding a prostitute was not easy in a small town. Split At least it wasn’t for me. But, after some discreet inquiries, I found one. If I give you her name, I’d have to make it up anyway. Here I will call her “Teach”.

As it worked out, $2K purchased six meetings. I met Teach through a discreet acquaintance. She was a very pretty 33-year-old woman who stood 5’4” and weighed 122 with all the weight in the right places. With a measurement of 34-24-36, those hips of hers were perfect. I love a woman in skirts and hips make all the different for how a skirt falls on a woman. Her height was in her legs and they were lovely. Her breasts were full B-cup and were still perky. The aureoles were small and dark. But when aroused, her nipples stood out like little flags. Her waist was trim but not skinny. Her auburn hair was shoulder length and was cut simply. Her auburn carpet was the same color as that on her head and was trimmed to a little very short patch. It didn’t get in the way when I sought nourishment from her life force.

She dressed conservatively as her daytime job was an elementary school teacher. She had been divorced for three years and had a pretty, nine-year-old daughter with whom she lived in a modest home in an older (but nice) part of town. The teacher’s salary of $42K/yr was a good start and the child support of $400/mo helped her, but my contribution of $24K a year made her life far more manageable. I was aware that she would also be seeing others and, in the beginning, I gather she was doing so.

All the clothing I purchased for her was in drawers in my Master Bedroom. That certainly was no hardship on me. When I purchased the ‘mission style’ furniture suite for my bedroom, I did not have enough clothing to fill up 50% of the drawers. The walk in closet was also more than half-empty. Finally, what I bought for her wasn’t for public consumption.

I never met her at her home for ‘services’. As I lived alone, she came to my home. There was no need for hotels or motels. Once a month, on the first of the month, I deposited a check for two thousand dollars in her checking account. It was payment in advance. There were no dollars exchanged at our meetings.

She would arrive; retire alone to the Master Bedroom and Master Bathroom. I would have already taken a shower (as per our agreement). She would hang up her street clothes, shower, do whatever she needed and then dress for ‘us.’

Once she was ready for me she would wrap herself in a silk kimono and “find me” in my home office – which was a real office. I had turned one of the three bedrooms into it. The room is right off the entrance foyer. It is where I wrote the first draft of this, before time and my life took me into a larger home. It was where I conducted most of my business, day or night, for many years. The office was usually dimly illuminated and her presence in there has always been a sight to behold; a Degas, in shade. The small smile which would cross her face betrayed amusement that I could actually get distracted with work while she was in my house changing for our intimate mating sessions. I was hopeless.

She was not sure what to make of me, other than she knew I was nuts for her. I knew it was a ‘for pay’ service and I was not confused, but I was never the less enthralled by her beauty and grace. Still, I did not moon over her. For that, she was thankful. There was no confusion about roles.

Sessions sometimes were soft, sweet, gentle and quiet. Sometimes they were far more energetic. We had, on occasions tied each other up. I have had her call me Master throughout some sessions and she has had me call her Mistress for some. I have taken her in every hole she has, willingly. There was a patience, and openness, that thrilled me about her in bed. It was always new. When she touched me then, and even now years later, she was and is paying attention.

She knew when a muscle was tight today but wasn’t last time. She sensed my urgency when it arose and my desire for a lower tempo when I had it. It might have been a job, but she was a master craftsperson and the results mattered to her.

There was never a problem with her ability to cum. She could cum multiple times whenever we made love. She liked sex. She seemed to like sex with me. I was only good for up to two a session and sometimes only one, but I did not cum quickly or easily. Thankfully, those little blue pills came along. I actually do need them; and so I remained hard for her.

Entering her was special. Her pussy muscles could get you off without you moving at all. She was simply amazing. You could not embarrass her, you could not surprise her, and shame on you if you ever considered humiliating her. She was class from the first step she took into your world to the kiss goodbye at the door when she left.

Some of the toys we used, we purchased, and some were improvised. I purchased the padded restraint cuffs for wrists and ankles with D rings but the thigh-high hose I attached to the restraints on one end and the bed’s head and footboards on the other ends were simply old hose she was no longer wearing.

The plastic sheeting I laid out over the bed before I tied her up face down one evening came from a local hardware store, but I specially purchased the fragrant oil with which I doused her.

I filled in a big part of what I needed in my life with this wonderful woman. You might be dismissive of her as a prostitute, but I cannot be. She had class, taste, discretion, intelligence, beauty, compassion and a respect for life’s odd outcomes.

Now that Teach was in my life, I was happy with my arrangement.

Things changed when one night, I slipped a cylindrical pillow under her hips. Her ass was raised up off the bed. I put a penguin, vibrating dildo in her pussy with the penguin head resting against her clit and set its dial on medium. Then I mounted her from behind. The oil was super slick and I had applied it well over her ass. As my cock slid into her backdoor, I met very little resistance. I nibbled on her right ear as I reached under her to grab her left nipple, which I pinched hard with my hand. My other hand found the penguin, with which I played, moving it around inside her, as I repeatedly rammed my cock deep into her ass. Her gasps, yips, yelps and demands for my cum were intense. At the end, after a long time, she did finally receive the hot cum. I stayed in her for a while, slowly moving both my semi-soft cock, and the penguin back and forth and producing small orgasms, like aftershocks.

Afterward I withdrew from her, removed the penguin, and the sheeting from the bed. We both showered.

When we came back to the bed and she pushed me down and sat on my chest, kneeling on my arms. She grabbed my head by the hair and gave me a warning I will long remember. If you are going to take my heart, soul and body like you did tonight, you had damned well better get ready for the consequences. You can’t do that to a woman without consequences. She will either run from you as far and as fast as she can, or she will never let you go. You had damned well better understand that.

She was a very smart woman and a very good woman. That night’s activity probably is what started a problem and my need to think hard about it. The warning was too late; the horse was already out of the barn.

♠ ♠ ♠ ♠ ♠

Chapter 2