Chapter 1

When I took a job just out of high school with the State of New York as a beginning office worker I was just 17 and not turning 18 until New Year’s Eve. I skipped 4th grade because of my reading and writing skills (my Mom and Grandma were both elementary school teachers and they prepared me well). The plan was to work the summer and fall, then do a semester at a local community college to enhance my math marks, and go to State University at New Paltz (Mid-Hudson area of NY) in September on a scholarship I earned through a local engineering firm.

I didn’t make great money that summer and fall, but the benefits were fantastic. I met more young women, HORNY young women, than all my friends who started college, even those in noted “party” schools. My job was easy, and I used basic math and writing skills to impress my bosses. It seems most of the “beginning office worker” positions were drones encouraged by their parents to “get a State job, you won’t have to work hard, and you’ll get a great retirement”. I wasn’t wired that way. Whatever I did, I worked as hard as I could at and tried to better myself. With 6 months in The State I was eligible to take exams to better my work grade and just before I was to leave and start my college career, I took every exam I was able to, and even one I was not fully qualified for, that my bedroom skills got me into.

Two days before the start of classes I took a position that got me a 20% raise and I convinced my parents I would reapply to the community college for a full year the next September with a nice savings account to enhance my college life. Begrudgingly, they let me have my way, but I never looked back. When the September semester started, and I was still working I was told to move out or go to school. I moved out and in with a work friend, and eventually my work friend’s sister that he had introduced me to. That lasted 5 months when she decided to go back to school and then I was on my own, making decent enough money to get a nice apartment.

Fast forward to New Year’s Eve 2015, my retirement date. With over 37 years in with The State I had earned a nice pension. I had researched a lot of places to retire and decided on Florida, out of the hurricane alley in a Florida city named Trinity, near the Gulf Coast, close to some of the best golfing in the country. I could be at the ocean in 25 minutes, at the famous Clearwater Beach in 40 minutes, and best of all I was in a resident owned community, with just a 50K buy-in where units sold for less than 30K. You couldn’t call them mobile homes, since they could never be moved, the owners called them “coaches”. The one I bought was bigger and more appointed than the townhouse I sold that more than paid for the lot, the coach and the move. After some research, Wyndtree at Thousand Oaks was ideal. The average age at this 55 and older community was but 62, compared to others that were 70 and above. There were lots of golfers, and even a fair share of single (divorced and widowed) women.

Now, let me explain that older (my age and above) women were not my normal quest. Over the years, I had been in 4 long term relationships and 100’s of short sprees and one-nighters. I came close to marriage 2 times, but the thought of one woman forever just did not sound good to me. I wasn’t one to cheat, but I did at times, and when I did I confessed because deception of the heart was not my thing. My longest relationship was with a tall, sexy, brunette named Gail who told me as she moved out that I was a despicable son of a bitch, (for cheating) and she would not trade her time with me for anything. Even the night before she left she offered to forgive all if I promised to never cheat again. (she offered me a bible with a picture of my deceased Mother on top of it to swear on) I told her it was a promise I could not keep. She fucked me and drove away with a van load of her things.

My usual quest was 25-35 women who appeared experienced and well settled (job, permanent living quarters, independent) and NOT shopping for a husband. One such lass, Amelia, summed it up quite well. She said to me from the outset when I asked her to go on a weekend golf outing to Lake Placid, “I make no promises. Let’s have a good time, get laid, have a laugh, fulfill a fantasy or two, and if we end, end as friends with memories we can jerk off to for years to come”.

Now, being 55 you might think I’m some sort of lecher chasing women half my age, but perhaps because I’ve never married, never smoked, and drink sparingly, I don’t look anywhere near even 50. Those reading this are among the very few who know I do use a gray out treatment on my full head of hair. It’s my lone vanity as I started graying (as all males in my family) in my early 30’s. You may think that moving to this community has made me alter my taste in women, but understand, most of the afore-described women I meet, I encounter at golf courses. They know that guys with expendable time and cash are course and country club regulars, AND they aren’t “fast lane” guys. No druggies, gamblers or bookmakers. You usually find them at city and full public courses. When a round of golf costs $150-200, you don’t get that type.

After spending 5 days moving in I was up early on my 1st Friday to hit a local course, Lansbrook, I had seen in many national tournaments. While it seemed natural I would play Thousand Oaks first, I knew I would have many years to play and master my “home” course. I slipped the starter $50 to get paired up with a “good” player or fill a foursome. The tags on my bag gave away the fact I was an established player. I’m not a duffer, but I’ve never broke 70 and rarely top 80, and have 2 aces. He looked down his sheet and nodded toward a three-some of 1 guy with 2 women.

“They’re regulars and look for a 6-8 handicapper, he’s shoots just over par a lot HERE, the girls are pretty good, they DO NOT gamble on their game. They like a fourth who can keep up with them.”

I looked and saw 3 sharply dressed people in their 30’s, a guy with 2 nice looking women, all looking confident. I nodded to the starter and he gave me a chit marker to bring them, basically telling them he would recommend me to make up their four. I smiled as I walked up and gave the chit to the guy who introduced himself as Karl.

“This is my wife Lara, and her sister Sonya. We take our game serious, don’t bet, and play the rules strictly. If that’s OK with you, please join us.” Karl said as I nodded and shook hands with all three.

It was a tough course that gave me fits, but for a course this tough, and my first time, I shot an 83, Karl a 74, and both ladies solid 80 and 81’s. As we played and talked Karl admitted that he had ONLY played this course for the past year and knew it well, the reason for his success. Both women had aspirations to turn pro and just needed help driving, their short games were as well as mine, and maybe Karls.

We had great conversation, a lot of laughs, a few drinks and a sandwich in the clubhouse afterwards. We hit the showers and agreed to exchange numbers to get together again. Long story short, later I agreed to drive Sonya home, and I did, the next morning . . . . . after fucking her brains out all night.

Karl and I were outside the locker rooms as he waited for his wife. He said he had an appointment with a realtor at 4:00 and if the girls didn’t hurry, he was going to have to bring Sonya along, not having time to drop her off before the meeting in Champion (Florida) where a new townhouse community was going up, adding “unless you could drop her, if it’s not out of your way”.

Sonya’s little golf outfit didn’t hide her long legs and every time she bent to get a ball I admired her round bottom in the matching shorts under her gold frock. She and her sister giggled at a lot of the comments I had made throughout the day and she eyed me a lot during our 19th hole late lunch and drinks. I thought my giving her the ride might give me a shot at asking her out, so I quickly agreed. She wasn’t in my car for 5 minutes when she asked with that giggle that drove me nuts all afternoon, “Care to play one more hole? I don’t need to go right home.”

Sonya was a quite playful and resourceful sex partner and the kind of one-night stand that remains just that, a one night stand. She obviously wasn’t making me the first guy she ever picked up at a country club and was quite a wide-open player in the bedroom as well as the links. But, someone that loose is not really my cup of tea, not that I’m carrying any mark of purity, but I don’t think I was “picked” because of any great attraction, I was just available with little vetting. It may seem unfair for me to judge like that seeing as how I didn’t vet her as well, but I knew I hadn’t played around since before I left New York, she, on the other hand may have done this a few times a week or as often as she golfed, and left after calling for an Uber, never even asking for my number. I wasn’t a crush she wanted to explore for a relationship, I was simply a sex partner. When she left, I felt a little used, not that I didn’t have a good time, it was just a sad feeling in the end. I sound hypocritical, but you had to be there. Later I would know her better.

That same morning, I showered and got ready for a shareholders meeting in the complex and I decided to walk to the meeting site and give myself a chance to check out the neighborhood. As I walked up the main center street I was catching up to another walker, perhaps heading to the same meeting. As I got closer I saw it was a woman, and as a constant “cheek-checker” I saw she had a lovely bottom in yoga pants with a top that just came to her hips. As I got closer I assumed she was not an owner there, but a visitor, obviously not “over 55”. As I moved to the street to pass her I nodded and smiled saying “Good Morning” to her. I was stunned when I saw her face, that she was obviously over 55, despite the tight, young looking, body.

She replied, “Yours was” (referring to my morning), “your guest was under 55.”

Quick witted, I snapped back, “Yes, she was. She was under 55, and over 55 all night long” and I kept walking to the conference room near the sites clubhouse.

I took a seat at one of the long tables where agendas were set out and a man with a push cart with cups and a coffee urn came by. I took a cup and thanked him as the tables began to fill with other owners. I studied the agenda trying to scope how long we were going to be there when the chair beside me was pulled out and someone sat. I looked up to see the woman I had encountered walking.

“Hello 55, I’m Mary-Eve, but most call me M.E. or Emmy.” She said with a smirk.

“Uh, hello, I’m Jake, sorry for the wise-ass comment before. I guess you just caught me off-guard.”

“I’m your neighbor across the way and down one. I saw you bring her home and saw her leave when the cab, or Uber got her this morning. I’m really not nosy, I just happened to be on my porch both times. Your guests don’t have to be 55, I was just giving you a hard time, a friendly jab. If we’re neighbors, we should be friends.”

“No offense taken, and sorry if my behavior upset or insulted you.” I said with a nod and a little handshake.

“You’re fine, it’s just we don’t see much of that here, you know, that walk of shame. She was obviously not a girlfriend.” She said as she put her agenda on top of the folder she carried in as she looked away from me as if to show her disapproval.

“It wasn’t what you think, you know, a business transaction.” I said to make her clear, but she just nodded, not making eye contact saying, “none of my business.”

Before the meeting started I tried to make conversation with her about her car, a ‘85 or ‘86 Cadillac Cimarron that looked showroom fresh, but she seemed disinterested in my interest. I tried one more time to engage her asking why she hadn’t used her golf cart to go to the meeting and she gave me a terse “some people get their exercise in healthier, safer, decent, ways”

I was off to a cold start with my neighbor that I hoped I could be at least “wave hello” acquaintances with. We were neighbors and the unit directly across from me, and the one right next to me were unoccupied at the time, the owners being late snow birds, or Canadiens who have to limit their time in the country to keep health insurance active.

The meeting started and at one point I was singled out, with 2 other couples, as new comers and we were welcomed. Afterwards many came up to wish me well and all seemed nice and friendly. I started my walk back and once again I came upon “Emmy”, but this time I asked, “Mind if I walk with you?”

She smiled this time and said she would like that. We made small conversation about backgrounds, just idle chit-chat, although I did find, and she made a point of telling me, she was 58 and had been widowed since the week she (they) moved in Wyndtree at Thousand Oaks 4 years before. They had moved here for the golf (located at the edge of Thousand Oaks Country Club), the community catered to golfers with its own driving range and access to the adjacent course practice greens. Unfortunately, her husband had a stroke and died on the course his 1st time out while she stayed home getting the new home in order.

I told her how sorry I was to hear that as she wiped away a tear. I realized it was probably something that haunted her each day.

“I’m surprised you stayed.” I said noting her sadness.

“No, it was my idea to come here, the course being so close, so beautiful. I never got a chance to play it. I haven’t golfed since. Oh, I go to the range here at the community, and I can walk to the practice putting green at Thousand Oaks. But I haven’t played a round since. . . .uh, I haven’t “played around” since either. Burying one husband was hard enough, can’t go through that again.”

“Well,” I said, “I hope we can be friends. Next time you go to the range let me know, I’d love to join you.” To which she softly said a non-committal “uh huh”.

I spent the next few days fine tuning my new home to my liking and just relaxing. If I were still back in New York, and especially if I remained working, I probably would have had some female companionship that week already. I had more than one “friends with benefits” who sought me out, or vice-versa, on a regular basis. There was also a divorced neighbor who wanted to make more of our relationship than sex, but she had cooled a bit lately once she knew I was moving.

Besides the golf courses I knew of in the area, I really didn’t know any places to go to meet ladies and to tell you the truth, my little tryst with Sonya made ME begin to feel like the whore I thought she was. The little projects around my place kept me occupied, but one thing was constant in this little development, there we constantly folks out walking, and they always stopped to introduce themselves. 90% of the available women were long past any sexual appeal, and those that I thought may have a bit of fire in them, were married, and I wasn’t playing that game.

The one exception was “Emmy (M.E.)” I wasn’t really sexually attracted to her, still having the eye for the younger ladies, but she was a constant in my neighborhood. Each time I looked to her unit, she would be on the enclosed front porch either reading or typing at her computer. With lights on at 5 in the morning, or 11 at night, she was there. Always in the front corner window were the silhouettes of the tops of 2 golf bags. I already knew one was her husbands and she kept them there as a reminder or tribute to him, the other was hers, of course.

On the Friday of that first full week I had to make a trip to Home Depot for a few tools and on my return, I did a quick glance to Emmys place and noticed her golf bag was gone. As I worked installing vertical blinds I saw her come home in her golf cart with her bag on the back, obviously returning from our community’s driving range. I slid open the window and said, “You should tell me when you go to the range, you might give me a few tips.”

She looked up and half smiled saying, “You weren’t home when I left.”

I couldn’t help but think she waited for me to leave as to avoid me. I hoped she didn’t think I was making any advances on her besides friendly, I wasn’t trying to woo a 58 year old woman. Without saying another word, she parked her cart and went inside without as much as glancing back at me.

I thought to myself that she must want to remain a very private person. I had tried to open a door for a mutual interest friendship, but she seemed to reject that.

Over the following 2 weeks I got out to golf 3 times, at Thousand Oaks once again, and then at Innisbrook and Lansbrook. I knew the pros at each of the 2 other courses, they had worked at New York courses I frequented. I did meet a young lady at Innisbrook who flirted with me at the bar, but she only gave me her number, with the promise of a date. It seems the girl, Marlene, was the daughter of the course pro. Though she was 24, she still didn’t want to flaunt the fact she might meet and leave with a man, especially a new non-member. We just exchanged numbers. I called her cell on that Friday and she answered quickly without even a hello.

“Jake! Where have you been? I was beginning to think you were a tease!”

“Hey, you had my number, why didn’t you call me?” I said in my defense.

“I’d like to think I was never so desperate as to make a booty call.” She said with a giggle, but also a tone that was all too serious.

I really hadn’t thought she was someone I might bed down on the first date, but she was acting, or at least presenting herself, that way. So, I answered her comment with a feigned indignant response, “What kind of boy do you think I am?”

There was a long pause, and then in the somewhat husky, smoky, voice that drew me to her after I first encountered her she said, “I wasn’t waiting for a call from a boy, I was hoping for a MAN, and I think you’re all man. You don’t need to tease me.”

“Can I meet you at Snappers (local watering hole, a post 19th hole favorite spot, so I was told)”

“That works, I’ll get an Uber there, I don’t have a car, I’m saving to get a place of my own, I’m back at my Dad’s house.”

After meeting at Snappers, she explained her plight. She had an accident, not her fault, she was waiting at a light. Her car was totaled, and she had serious leg injuries. The guy who hit her had no insurance, he skipped town, and she didn’t have collision insurance on her 8-year-old car. She was out a car, no one to sue for damages, and had medical bills not covered on her simple health policy. Since then, she had got a job with a hospital group (she was a physical therapist) with good benefits and was getting back on her feet.

I wasn’t convinced if all of her sob story were true, but she didn’t seem the “loser” type. It also seemed her insurance could have done more for her if she had pursued it, but with her in tight jeans and a top that showed nice cleavage I was a little forgiving of my own standards (staying away from losers, losing is catchy)

We had a couple drinks and ate (2 mixers or beers and I always eat before I drive) and I suggested going to her place (seeing if her story might change) and she reiterated she was living with her Dad. I was beginning to buy her whole story, but not ready to commit to a little affair, I had enough drama in the past and that was going to remain a thing of the past.

“Well, I can just bring you home, save you cab money.” I said acting indifferent to seek her agenda.

“Look,” She said offering her hands to me, “I thought we had a little spark that day at the golf course. I don’t make a habit of picking guys up there, it’s just I can have a few drinks on my Dads tab and meet a few friends there. You’ve heard of golf widows, we’re golf orphans. Our Moms or Dads are Pro’s, or Pro-want-to-be’s, you know, golf addicts. Of the bunch, I’m the oldest and only one other is of drinking age. Today, like the day we met, is my day off from work and my Dad won’t leave me home alone, that’s a long story.”

My drama alarm went off, but her sultry voice was getting me hard. I wasn’t buying her whole story, but as I held her hands I looked closely for any signs of a wedding ring, there was none. Earlier when she dropped a fork and bent to get it, her jeans and top parted enough to see a distinctive tan line, so I didn’t think she was a beach bunny. (Beach bunnies tan all over or almost, from skimpy string bottoms)

Holding her hands, I smiled and asked, “Do you want to leave with me, maybe go dance or something?”

“You said you just moved here, show me your place.” She said rather seductively. (She could recite a phone book and sound seductive)

“I’m at Wyndtree at Thousand Oaks, do you want to go see it?” I asked knowing I gave away my “over 55” status.

She turned her head and smiled suspiciously, “You’re in a 55 and over?” (very prevalent in that whole Tampa Bay area.)

I just nodded and waited for her reaction. She sat back in her seat and thought for a moment.