I Never Saw It Coming...

Rachel and Derek returned that summer and we started socializing a bit more per their prodding. Other than some fun times on the lake and a few more happy hours every month, we still remained reclusive. One night after work when we were playing drinking games at Dave and Lynn's, Rachel's prompting dropped a bomb on our relationship. We hadn't talked about it much since Wendy and I first hooked up, and I don't think we ever talked about it with Betsy, but the time had come for her to realize her plans to go away to finish her degree. Even though I knew the plan all along, I had completely forgotten where we were in the timeline.

Rachel was talking about going back to school and she innocently asked if Wendy was still going. She floored both Betsy and I by saying she was accepted to Syracuse and would be leaving in just over a month. Betsy and I looked at each other in shock, squeezing each other's hands under the table as Wendy matter-of-factly told us our relationship was over, in not so many words. We drove home silently, went to bed pretending it didn't happen, and woke up the next morning hoping it was just drunk talk. Wendy was downstairs making breakfast already as Betsy and I talked about it in bed.

The second we hit the bottom stair; Betsy started going off on Wendy. We had never fought. Everything came easy, but that morning Betsy erupted hysterically calling her every name in the book with tears pouring from her eyes. Wendy sat back and took it all until Betsy seemingly wore herself out before freaking out herself. Screaming about how we knew this was coming, how she wanted to try to do the long-distance thing before Betsy attacked her, she ended up storming out of the house leaving the two of us to console each other.

Betsy and I were laying together on the couch when a calmed down Wendy returned. She apologized to us for not talking about her plans and keeping us in the dark. Betsy sobbed as I told Wendy how hurt we were and how shitty of her it was to keep things this big from us. We talked for a while and everything seemed amicable, but her betrayal drove a spike through the heart of the entire relationship. Wendy remained distant over the following days and things between Betsy and I were strained under the pressure.

The last month together as a group was brutal. Everyone pretended that we were all ok, but none of us were. When it came time for Wendy to leave, I had forgiven her, but it forever severed our love for each other. She confessed that while toiling over college applications and making her plans to depart, she forced herself to break up with us 'in her mind' in order to fulfill her plans. I lived up to my promise of paying for her school, but when she told me she wasn't coming back for the holidays, I never spoke to her again. I found some solace in the ongoing relationship with Betsy, but it wasn't the same. We slogged it out much longer than we should have, but ultimately, we were only together as a result of our mutual love for Wendy. She was the bond that held the three of us together and once she was gone, Betsy and I found ourselves mostly strangers living in the same house.

Betsy moved out in the middle of spring and I was once again, totally alone. I tried to rekindle the lost friendship with Dave and Lynn, but they were about to have a baby and I knew it could never be the same. We hung out a couple of times and I lost track of them a short time later. Stronger as the result of my time with Wendy, I controlled my urges to drink myself to death and came to terms with my ongoing depression. By mid-summer I was failing to keep myself busy enough and was totally bored out of my mind. I was struggling to make connections with people in town, still totally an outsider.

Out of the blue one evening as I was sitting on the dock, drinking my first beer in days, Betsy texted me to see how I was doing. I lied, telling her I was doing well, and she told me about how she was finding direction in her life. On one hand, I was happy for her, but it magnified my lack of anything worth talking about. She was back at the call center, looking to start school in the fall, and angling to advance as a supervisor. I told her I was proud of her and she promised to keep in touch. A couple of days later, she lived up to her promise and followed up with me. We texted back and forth for a couple of weeks before I gave in to my impulses and invited her over for the weekend.

It was nice having her there and reignited my desire to try to make more connections to get on with my life. We talked more that weekend than we had in our relationship and I found myself having feelings for her, more than before, after we had sex. She could sense my desperation and called me out just before she left. Acknowledging our relationship revolved around Wendy and while I, "was a great lay and a cool friend," there was nothing there with Wendy out of the picture. She was right. I cried a bit when she left and felt sorrier for myself than I had in years.

I reached out to Betsy the next day and told her how sad I was. She called me and we talked for about an hour before she had to go to work. Prodding me to "put myself out there more," she encouraged me to at least get on social media and maybe try some dating apps. I spent the rest of the day setting up social media accounts and by the end of the week, I was 'connected' with a few dozen people from my past, most of whom I hadn't thought about in years. The next few weeks, more and more 'friend requests' trickled in and I had a few brief interactions with old acquaintances from high school, former coworkers, and even some of Meagan's family. It all felt pretty hollow and strange, but it was a little bit of a lifeline and I admit, it did help.

The little conversations were nice, but looking through the profiles as the requests came in, left me feeling completely empty. I had all the money in the world, but once again, I felt as if I had nothing. People who I thought would surely end up in jail or dead had beautiful families and here I was knocking on 40, totally alone. Betsy reminded me that everything online was fake and people only posted their best moments, but looking through the pictures and even some of the drama-postings, I couldn't shake it. Even if they were only posting the good times, they had good times. They had lives. I had a big empty house, a friend who I texted with, and no 'times' of my own.

I dipped my toes into the waters of the dating apps, which were even more disastrous. Apparently, I'm ugly. No matter where I set my location or how many fives I swiped on, I got no matches. When I started swiping on everyone, it didn't get much better. If my matches were a reflection of my profile pictures and what I thought were witty answers to the basic questions, I was a cross between Dick Cheyney and that new skin under a blister you popped too early. Gross and revolting, apparently.

Once again, Betsy provided me with a suggestion, but it made me uncomfortable. Posting pictures that showed my house or me on the boat seemed gross, but out of desperation, I took the shot. I also fluffed up my profile with some not-so-subtle indications that I had a little money and while effective, it made me feel pretty disgusting. All of a sudden 9's and 10's were interested, along with everyone else. I felt sick to my stomach as the messages started streaming in consistently. At one point in my life, I was worthy of love. I was a good dad. I was a devoted husband. I wasn't just a middle-aged guy with a fat bank account. Even with Wendy, even though I totally took care of her, it wasn't about money.

Unfortunately, my despondency got the best of me. I had tossed my phone to the side as far as those hookup apps were concerned, but days later I relented by responding to every message and making plans, booking myself solid daily. I was disgusted with myself, but the little head ran the show and one after another, I had a constant parade of gold-digging whores in and out of my bedroom. I suppose some of them were nice and genuine, but the juxtaposition of my previous failures and newfound success driven by my admission that I had money cursed any chance of a real connection.

That's not to say it wasn't pretty fun. I had all kinds of wild and crazy sex. The biggest thing I found during my three months of fucking a new girl almost every day was that while there's a lot good sex to be had, there's even more bad. I guess I'd been lucky over the years, never really encountering a 'dead fish.' But then again, I wasn't just banging 9's and 10's. I don't even care to remember most of their names, but they were almost all the same. None too eager, but all more than willing. None cared to pleasure me, or sometimes themselves, they were just content with laying there as I mechanically got my rocks off. I discovered that the less hot ones were a bit more fun, but they still didn't fill the void. That said, there were definitely a few notable lays worth mentioning.

Jane or Joan or something. I don't remember. She kept asking me to call her different names. One of the weird things she was into. She was 22 and nearly turned me off completely talking about how she loved that I was so much older. She definitely had daddy issues and a fetish for older men. She arrived at my house on a Friday night and fucked like a champion, insatiably, through that Sunday. I actually had to cancel plans with a several other girls that weekend as this hot little bleached blond bimbo drained me of all of my fluids. She fucked like an absolute savage. Everything about her screamed sex, including her screaming. She had a tiny little tanned body, impossible curves for a girl who probably weighed 100lbs soaking wet, and wanted it in every way possible. We fucked three times that first ight and she woke me up a few hours after I passed out for another round.

The next morning, she begged to stay as she dropped to her knees in the living room and gave me a blowjob that would make a porn star blush. I fucked her against the wall. I put it in her ass as she pleaded for me to hurt her while she was bent over the couch. I twisted her little body in ways that would break my GI Joes growing up. When I say I fucked her a dozen times, it may sound like hyperbole, but honestly, it's might be an understatement. I fucked her so much that my dick was raw for days and my ejaculations ran completely dry. Finally on Sunday afternoon I told her I had to go out of town that night to convince her to leave. Truth is, I had to convince myself a little bit too. She was by far the most beautiful woman I'd ever been with and a complete and total nympho. I was celibate another two days as I recovered and ended up with another girl that Wednesday, after blocking that little freak because she was blowing me up at all hours.

Another fun one was Roxie. Roxie wasn't quite as hot as many of the others, but she was downright sexy. A big amazon looking chick with fiery red hair, huge tits, and a fat ass. Honestly at over 6ft tall she was quit intimidating, but undeniably attractive. She was in her late 20's and always took control. The moment she arrived she jumped all over me like an animal. No awkward small talk, barely any talk at all. When I opened the door, she grabbed me up like a ragdoll and rammed her tongue down my throat. She dragged me to the couch, tore my clothes off, and fucked me. It's one thing to say 'she fucked me' casually, but when I say it now, know that she REALLY fucked me. She held me down, hiked up her skirt, and shoved my cock inside of her. She smashed me through that couch and didn't stop until my cock was completely soft. From there she stripped off her clothes, pulled me up the stairs into my shower, and made me touch every luscious inch of her thick juicy body until I could muster up the energy (and courage) to get hard and fuck her again. Or, should I say, for her to fuck me again.

Roxie was one of the few that I met up with more than once. I had never experienced such a big, impressive woman, and she was a lot of fun. There was never anything, but sex with her and she never stayed the night or anything. I don't think she was a gold-digger as much as she just got off on dominating rich, powerful men. Not that I was powerful in any way, but I'm sure she assumed I was important given my apparent wealth. All these months later, I still have moments where I fantasize about her pretty, angry face, scolding me as she took me completely. Not to mention, the smattering of freckles across her soft, pale, endlessly voluptuous skin, and the fluorescent orange stripe of pubic hair decorating her bright pink pussy.

Dani was a total sweetheart. If it wasn't for that stupid app, I may have wanted to pursue something with her. Probably the oldest woman I was with during this time, but you couldn't tell by looking at her. We actually had some real conversations, but the lingering thought of her only being there because of my big dumb house on the lake forced me to push her away. She may have been perfect, and definitely was in the sack. Her body was relatively average with clothes on. She was pretty lean, but had some curves. However, her tits were genuinely Goldilocks status. Not too big, not too small, firm, but not hard, super perky with quarter-sized areolas, and pencil eraser nipples that god himself should be proud of. Her ass was pretty good too, maybe a little flat, but those tits were the star of the show. Fucking her was a fantastic balance of sensual, passionate, and intense. Just enough dirty talk to make it fun, but not so much to be performative. She loved kissing, loved teasing, and loved a mix of light and hard touch. I'm guessing I didn't live up to my end because after a couple of meetings, she ended up ghosting me.

I came to recognize that filling holes wasn't filling the holes in my life and after an STD requiring some antibiotics and several fake-pregnancy threats I deleted the apps. My addictive personality and propensity for self-sabotage had revealed itself through my dick instead of my drinking. Thankfully, being sober, I was able to catch it before it got totally out of control. However, I was once again quite lonely.

I stayed by myself for months and I sat alone on New Year's wondering where my life was going and hoping for something more. I had been there before, but for some reason it felt like my life was about to change for the better. The thought stuck in my head for weeks and I continued to struggle to figure out how to bring my potential to fruition. I hoped for some direction, some sign or inspiration to push me toward a new path and a crushing phone call put me on that heading.

I was just falling asleep on the couch watching some weird documentary about a cult on Netflix when my phone began to buzz. I was a little hazy, but I recognized the LA area code attached to an unfamiliar number and the second I heard the voice on the other end I knew who it was and my heart sank. It was Dom's son, Jeremiah.

Dom had been fighting with diabetes for years and despite her experience as a nurse, still struggled to manage it. She had let it get pretty bad and had a stroke earlier that morning. She was in a coma and the outlook was grim. It was too late to get on a flight, so I headed straight for the airport in the morning without getting a wink of sleep. The entire flight I cursed myself for not making more time for her, not reaching out enough, and failing to live up to my promises to visit her every time we talked.

Arriving at the hospital I felt sick to my stomach as I found her in a room not dissimilar to the room she cared for me in, surrounded by her kids and grandkids. With tears in our eyes, we greeted each other trying to ignore her dying next to us with all of the machines beeping and buzzing to keep her alive. We took turns staying by her side for almost a week until finally the doctors convinced the family that she wasn't coming back. It was over.

Dominque Estelle Jackson died on February the 2^nd. She was a loving mother, a devoted friend, and a hero to at least one.

As we sat around sobbing while the life left her body, a wave of fury coursed through my body. I wanted to burn the fucking world down. I wanted to destroy everything. I wanted to claw the eyes out of every smiling face and every single person who ever took the people they cared about for granted. I wanted to let myself completely go, ruin everything I ever came in contact with, but I knew, I couldn't. After all she did for me, I couldn't let the best friend I ever had down in that way. The molten rage burned quickly, lighting a fire under me unlike anything I'd ever experienced before.

I took care of Dom's family, just as she took care of me. 'No' was not an acceptable answer. They didn't have a choice. I did everything I could to handle planning her arrangements while being careful not to take anything away from them. I wanted to build a church in her honor just to entomb her for eternity, but I was constantly reminded that she would 'kick my ass if I even thought about doing something that stupid.' I could hear her chastising me as plain as day. Instead, I ran errands, I picked up kids, I bought groceries, and of course, I paid for everything. That was one thing that she couldn't tell me not to do from beyond the grave. Well, that and setting up trust funds for all the grandchildren. I know she'd be pissed, but I felt so helpless and I needed to do something to repay her for saving my life.

When it came time, I put myself to good use by selling her house for the family. I talked to a few realtors, but they all seemed a little slimy. This was personal. I handled it completely, myself... well, I did have a little help along the way. As a result, it probably took longer than it should have, but I got top dollar and snuck in a little padding from my own pockets when handling the distribution of the proceeds to the family. During that time, several offers fell through to all of our disappointment. One in particular was interesting -- not because it was the first, not for the offer itself, not for the buyer or any of that stuff, but rather, for the realtor.

Shelly Anderson.

Shelly was a mid-30's, somewhat successful realtor in the area. She had her face plastered on bus benches and a billboard or two around that side of town. She was smart, sweet, driven, and ended up helping me with the finer details of navigating the sale. Considering a guy who hadn't really worked most of his adult life and barely had a high school education was effectively the selling agent, she put in a lot of work. It was quite surprising to me how willing she was to help me after our deal fell through. I found myself texting and calling with questions and she met me for drinks to go over offers as they came in. We were fast friends.

When we sat down to go over the final contract to sell Dom's house, I asked her to dinner. Everything was pretty professional up to this point, but I suspected she wasn't just doing everything for me out of the goodness of her heart. I could tell she liked me. When I picked her up from her quaint little 2-bedroom house, I drowned in the butterflies as she answered the door looking absolutely stunning. Her piercing blue eyes glittered in the light of her porch and her deep red lipstick contrasting her big bright smile made me quiver. The straight blond hair brushing her bare shoulders just above her strapless black dress made me feel lucky to be alive.

We went to a high-end restaurant and sipped wine on the patio, talking endlessly until the waiter seemingly gave up on serving us food. I told her all about Dom and the pit of alcohol-fueled despair she pulled me from and she shared with me the failures of her marriage and the subsequent relief that came with her divorce. I fell in love with her on the spot. Dropping her off and sharing a nice, romantic kiss, I practically skipped back to the car. Driving back to the hotel that night, I thought of Meagan and our little Hailey; the twins. For the first time thinking of them alongside the thoughts of another woman didn't make me feel guilty, or gross. It felt... right.