View looking along a coastline

An Investment That Paid Off

by John S. Lloyd

I was riding my bicycle down the Lake Shore Drive path along the lake. There was a traffic jam and before I could get my clips out of the stirrups I fell into another biker who also fell. I was helped up but knew I had hurt my shoulder even though there was no visible scrape. I didn’t think much of it and apologized to the other rider who snapped, “Old man don’t you know how to ride a bike.” I apologized again and the fellow sped off leaving me standing in the middle of the path blocking traffic. I mounted my bike and rode toward the bike rental shop where I had rented the bike and bought the clip shoes.

I told the manager about my fall and apologized for the scratch on the back fender. She inquired as to how I was doing and I lied, “I’m OK, but will take a couple of Aleve when I get back to the hotel.” I was in Chicago for a wedding of the daughter of an old friend which was scheduled for the next day with a party following in the evening. I planned to fly back to my summer home in Vermont on Sunday. I didn’t pay much attention to my right shoulder and the pain was manageable with a couple of Aleve every four hours. I would see my general practitioner when I got back to Burlington.

The wedding was beautiful with my friend’s daughter looking like a princess in her long, flowing white dress and sequined veil. Her attendants were dressed in pale yellow satin street length dresses high in the front and cut low in the back. The three men accompanying the groom wore traditional summer white tuxedos. The Fourth Presbyterian Church was decorated with yellow roses about every third row. Probably two hundred guests hardly filled the front quarter of the magnificent, stately church. The wedding ceremony was brief. Afterwards the guests waited for the bride and groom to come out in the warm summer air in the church’s garden.

A handsome young man

Reg at the Wedding

I noticed a strikingly handsome young man with close cut black hair standing alone. Because he and the other groomsmen entered from the side I had not seen him close up. He stood aside as if he didn’t know many of the guests. I guessed he was a friend of the groom who lived in New York City. I knew how he felt because I was also from out of town, too. I didn’t know anyone except my friend, Jeremy, who I have known since we were fraternity brothers at Colgate. Jeremy and I had stayed in touch because we were with the same investment banking firm.

I approached the young fellow, “Hello, I’m John Cochran. I presume, you’re like me and don’t know many of the guests.”

“You are correct, Sir. I work with Jim in New York. When he asked me to stand with him I said I would. We’re close friends and play handball once or twice a week. We live in the same building and happened to meet the day both of us moved in. That was three years ago. What about you?”

Before I answered I couldn’t help but take in the sheer beauty before me. “Excuse me but you asked me my connection to the bride or groom?”

“Yes, you seemed to zone off.”

A handsome older man

John at the Wedding

“Excuse me for saying but you are a very handsome young man. To answer your question I have known the bride’s father since we were fraternity brothers at Colgate. He and I are investment bankers but he is here in Chicago and I live in Pittsburgh.”

“Thank you for the compliment. You’re handsome yourself.”

He paused trying to decide what to say next when the groom approached us and said, “Reg, come over here I have someone that would like to meet you.”

He turned away but said, “See you at the party, John.” I was stunned he remembered my name. The crowd was dispersing since the party at the Casino Club wasn’t scheduled to start until 6:30 for cocktails. I walked a couple of blocks to the Fairmont and decided to have brandy old fashion before taking a short nap. I heard, “John, what are you drinking?” I turned and it was Reg and one of the other groom’s men.

“Reg, it’s a brandy old fashion. An old fashioned type drink.”

“Sounds interesting I’ll have one. What about you Jeff?”

The bartender mixed two brandy old fashions for them and we moved to a cocktail table with three cushioned chairs. The small talk was insignificant except I learned that Reg was born Capri, Italy. He came to the USA with his mother and sister when he was a baby. He had no lingering accent. It turned out Jeff was from New York as well. After thirty minutes of small talk I excused myself for a nap. The fellows continued sitting in the bar and said they would see me later.

During the cocktail hour I had a chance to speak to Jim, the bride’s father, who thanked me for coming. I apologized for not having a partner because my most recent partner and I had split up a few months back. Jim had met him twice and he asked how I was doing.

“I said for a guy approaching early retirement I’m doing fine. I was hoping Randy and I could make a go of it. He was a great traveling companion but was too interested in his multiple evening cocktails. I was tired of making excuses for his drinking. I’m glad he is behind me.” The conversation turned to Jim and June’s plans for retirement which he told me was only a year away. He was two years older than me. I thanked him for the invitation and moved with the others to our assigned tables. Ours was a mixed table of friends and distant relatives.

During the dancing I longed to have Randy with me. He was a great dancer and made me look good. The DJ did a nice job of mixing older and newer songs to cross generations. I moved away from our table and stood watching the dancers. The bride and groom made a handsome couple. Like so many young couples they had lived together in New York for three years before deciding to get married. I was sure they were going to produce beautiful children.

As the evening was coming to an end Reg came up to me. “John, it was great to meet you. Do you mind if I ask for your contact information? Do you get to New York?”

“I’m frequently in New York sometimes on business but more often to see a show or attend a symphony performance.”

“Let me know when you are in town. I would like to have dinner with you and maybe see a show. Have you seen Hamilton?” I admitted I had and really didn’t like it as much as other shows. I guess I was showing my age.

He smiled, “I have seen it and I don’t like it. When my friends come to New York they want to see it. I have seen it twice but now send folks to see it and meet them after the show for dinner.” He took my hand to shake it but put his other hand around mine which to me suggested something more than acquaintance’s parting. I assured him I would definitely let him know when I was traveling to New York.

As it turned out I didn’t get to New York until shortly after New Year's for a business meeting. I thought about Reg infrequently but remembered his final handshake. The company was having an investor’s conference at the Grand Hyatt, a hotel I really don’t like, so I reserved a room at the recently renovated Westbury on 69th Street. When I checked in I was impressed with the differences but was sad the old stately dining room had been modernized. The old dining room epitomized the elegance of New York in the 1970’s and 80’s. My room was compact but very functional for a single guy. I was alone in New York for the first time in five years.

I had texted Reg not knowing if he had any interest in following through on his invitation. He texted me right back. He suggested meeting on at 8:30 Friday evening for dinner at Pearl’s Oyster Bar near Union Square. He told we would go to the Duplex which is near where he lives. I knew the Duplex was one of the oldest gay piano bars in New York. How did he know I was gay? I couldn’t believe he was gay and the least bit interested in me. I texted him back that I would meet him at the oyster bar at 8:30.

What I wore to dinner was not my usual blue jeans and polo shirt that I wore in less than trendy Pittsburgh. I liked being casually chic. I ordered an Uber which was at the curb as I walked out of the Westbury at 8:00. Traffic was heavy so I hoped we would get all the way downtown on time. I had Reg’s cell number programmed if it looked like we were going to be late. I was more nervous than I had been as a twenty-something coming out to friends and family. I couldn’t believe I was going on a real date with a gorgeous hunk of a guy. He was waiting outside as we pulled up about five minutes late. He was dressed in tight fitting jeans and a long-sleeved, loose, white knit shirt whose neck line did not disguise the fact that the dark hair on his head was duplicated on his chest. I couldn’t help but stare. He hugged me outside the small, local restaurant. The place was noisy but it was easy to talk.

The Duplex, by the time we got there, was filling up. The Duplex has traditionally been where the young Broadway performers come after the show goes dark. They sing and drink with the regulars. Reg and I enjoyed each other’s company for three hours before I ordered an Uber car. He didn’t invite me to his place even though he said he lived a couple of blocks away. As we parted he said, ”Interested in going with me to Vegas next month?”

I waited too long, “I don’t think so but let’s talk. Are you around tomorrow?”

“Tomorrow is busy with squash and a late afternoon quilting party. Maybe Sunday afternoon?”

“ What the hell is a quilting party? I’ll be flying back to Pittsburgh on Sunday. I’ll call you next week.”

A quick hug he said, “A quilting party is a hookup event sponsored by the Catholic church I go to.”

I wondered why Las Vegas, which is a place I really didn’t like. If I wanted to try to make something of our spring/fall relationship maybe I should go. On the flight back to Pittsburgh I couldn’t get his invitation out of my mind. When I went to work Monday I thought ‘why not’ I’ll go.

When I finally caught up with him on Wednesday the following week Las Vegas wasn’t even mentioned. He asked if I wanted to join him and some friends who were going to Puerto Vallarta in May.

I said, “Reg, what is an old guy like me have in common with your young, energetic friends.”

“We’re all bringing older boyfriends.”

“Are we boyfriends?” I said somewhat sarcastically.

He came back puzzled, “I thought we were. Aren’t we?” His comment suggested that things are differently in my generation than his.

I recovered quickly, “I guess we are. When are you going? I’m sure I can join you. How long are you staying?” He told me it was the Cinco de Mayo weekend with a day tagged on before and after the three day weekend. I told him I would check flights and let him know when I was arriving. I hung up and shook my head wondering what does an almost sixty year old have in common with someone under thirty. I concluded I was going to go for the ride.

When I arrived in Puerto Vallarta he was waiting for me outside security. We hugged and he grabbed my carry on which is all I brought. The taxi took us to the four bedroom house that the boys had rented in the Romantica area of town. The house had a pool and plenty of room. There were more couples than bedrooms so Reg and I were bunking with another couple whose age difference wasn’t as significant as ours. The sleeping arrangement would make intimacy beyond cuddling awkward.

All the couples arrived by Friday evening when we gathered around the pool for an informal cocktail party. With ten other people I was not only having trouble remembering names but also remembering who was paired up with whom. After a couple of drinks Reg and I paired up with our bunk mates and went to dinner. Reg and I didn’t get much time to ourselves except in bed. He invited me to sleep naked with him as the other couple was doing. He cuddled up to my backside and kissed my neck for the longest time. I loved it and turned to kiss him. I could feel his massive cock against my middle. I squeezed it and he kissed me harder.

I found the conversation easier with the older men since we had more in common. The millennials were discussing sports teams, concerts by artists I hadn’t heard of and openly discussed their other sexual conquests. The older guys who had been married discussed their kids and grandkids. Since I had neither I listened until one fellow mentioned that he and his partner had recently bought a condo in Stowe, Vermont. That was my opening since my summer place was only a hour south of Stowe. That opened the group discussion up to favorite places to live or visit. Reg and a couple of his friends joined us but didn’t say much.

The weekend was fun but I didn’t think much had changed in my relationship with Reg. We kissed and cuddled but that was it. I really didn’t know much more about him than I found out at the wedding. The plane he was on held eight of the guests all going to New York. Of the remaining four men only I was going to Pittsburgh.

Immediately after I returned home he texted me that he liked us being together and hoped we could do it again. He asked me to text him if I had plans to be in New York. I replied that I would. After not hearing from Reg for more than a month I assumed our time together was a fling. I began to look around Pittsburgh for another roommate since Jeff, my former partner, had finally moved out. I had several men visit me that I met on Silver Daddies. It seemed like they were bottoms as was I which made our mating unpleasant. All suffered some degree of erectile dysfunction. I kept a supply of generic Viagra handy.

I had a more serious physical problem which was my right shoulder that I injured the day before the wedding. While I had discussed the fall with my GP in Vermont he suggested seeing a shoulder specialist in Pittsburgh when I returned. I did that and the doctor prescribed physical therapy which I began twice a week. I noticed my mobility was becoming more restricted. I told Reg about my fall when we were in Puerto Vallarta. He noticed that I winced when we were in bed together. He told me he had a good friend who specialized in sports medicine injuries at NYU Medical School. He suggested I visit him. I thought going to New York for medical care was silly since we have world famous health care facilities in Pittsburgh. By Thanksgiving the pain had gotten too bad not to do something. I texted Reg and asked him for his doctor friend’s name. He texted me right back with the fellow’s contact information and added that if I had to have surgery I could stay with him so he could nurse me. I appreciated the offer.

Before I had the appointment Reg’s friend ordered an MRI to be done in Pittsburgh. He spoke to me before I saw him. He recommended that we do surgery because my right rotator cuff in his words ‘looks like the ends of a frayed rope.’ I texted Reg that I was coming to New York for surgery and would like to recuperate at his place since the surgery was an outpatient procedure. He texted me right back and said he would go with me and wait until I was ready to come to his place. I didn’t realize how much pain I was going to be in when the surgery was completed. The next three days I lay propped up on his sofa as he constantly changed my ice pack or brought me water to take my Aleve. I refused to take oxycontin. Reg was wonderful and even took off work on my first day of recovery to be available if I needed anything. He was gentle but didn’t hesitate touching intimate parts of my body as he cleaned me and showered me.

On the third day when I was feeling better Reg confided in me that the reason he had been out of regular communication was his mother. He said, “Mom, has been going downhill mentally for a while but in the last few months has really slipped. I tried to keep her in her apartment in Brooklyn where she lives with my aunt and my older sister. They couldn’t handle her since my sister was working. My aunt’s health is not good but she is mentally fine. I moved mother into dementia care facility in Bensonhurst where I grew up. It’s really expensive. She had saved up about $300,000 after working thirty years in the garment district. She was a master seamstress. But if she lives more than two years we will have to move her to a Medicaid facility and most of them are deplorable.”

“I’m sorry to hear that.”

Reg said, “What about your parents? Are they alive?”

“My mother passed away from breast cancer many years ago. My father remarried and never approved of my life style. He lives in South Florida. I have very little contact with him but my sister keeps in touch with him. As far as I know he is still alive.”

Reg didn’t say more about his mother. He ordered in a pizza for dinner. I was planning to leave on the train the next day to return to Pittsburgh rather than hassle with the security at the airport. He saw me off in an Uber before he headed downtown to work. I didn’t hear anything from him except a quick reply to my text that I had arrived home safely. I worried about him but really couldn’t do much from Pittsburgh. I sent him a text greeting for Christmas but heard nothing back then or at New Year's. I knew I had to move on with my life without Reg.

I had not found a suitable roommate by early April when Reg sent a text that he was coming to Pittsburgh and could he stay with me. With some trepidation and irritation I replied that he was welcome to stay. His text gave no reason for his being in Pittsburgh. He said he was driving out and would arrive the Thursday before Easter. I didn’t even know he had a car I had to think of where he would park since all the spaces in my building were owned or rented. I overheard my neighbor say she was going to be away so I asked her if a guest could use her space. She told me that she and her boyfriend were going to be gone only one week. I assured her if my guest was staying longer we would make other arrangements.

I was shocked at Reg’s appearance when I opened my front door and saw him. He had lost weight and muscle mass. His shiny, longer black hair seemed to have lost its luster. His first words were, “I know I look terrible. Don’t stare.”

“Come in, for Christ’s sake and tell me what has happened to you?”

He walked in, dropped his bag down and broke into tears. I held him close and we sat down on the sofa. He rested his head on my left shoulder and cried. I stoked his beautiful hair and rubbed his cropped beard gently. I was determined not to rush him into telling me what had happened. He finally said, “John, I’m alone.”

“You have me.”

“No I mean my world has collapsed. Aunt Ruth died of a stroke in January followed by my sister’s heart attack and death in March. I buried mother last week.”

“Oh my gawd why didn’t you tell me.”

“I didn’t want to burden you.”

“You silly boy, I could have done something.”

“Don’t worry about it. Most of the details have been handled but you could help me with some of the money issues that still haven’t been resolved. To top things off my company’s president announced that he was moving headquarters to Atlanta I wasn’t offered a transfer. I have good severance but no job.”

“Stay here with me and we’ll figure things out.”

“I’ll stay for a while but I have decided to go to Capri for the summer. I have an uncle who lives on the island who said I could drive his taxi. You have to be a native to own and drive a taxi on Capri.”

“Have you ever been to Capri?”

“Yes, a couple of times when I was younger. The place is small I can learn how to get around quickly. The roads are so narrow.”

Young naked man

Reg is Ready

After a leisurely dinner of pasta, salad and red wine we went into my bedroom. I undressed him. We weren’t in a hurry as we snuggled and kissed. When it came time for physical sex he wanted me to straddle him and get used to his substantial member. I couldn’t believe what he was asking but I couldn’t have been happier. Underneath the butt of this fifty-seven year old guy would be the most gorgeous young man with black hair, cute beard, a slightly less muscular physique and the biggest cock I had ever seen. He was my twenty-eight year old Italian god.

I was more than ready to give it a try. We showered after I prepared myself with a warm water enema. We hugged and kissed over and over in the dim light of the bathroom. I dried him and he did the same for me.

Older naked man

John is Ready

We didn’t have to do anything to get our cocks ready. I was ready to take him inside my anal cavity. I was out of my mind going up and down on Reg’s member. He carefully edged my dick to coordinate with his ejaculation. I spewed all over his chest as he filled me with his sperm. I didn’t want to get off and he didn’t rush me. His cock didn’t deflate. We did finally get out of bed to shower.

The next morning I called my office and told my assistant that I was taking unexpected vacation. She wished me a good time but asked no questions. Reg and I spent a sensual, romantic week together. We drove through small villages, ate a comfortable little cafes and visited vineyards selling regional wine. We spent plenty of time in bed doing what two gay men do. I was pleased that Reg’s color was beginning to return. He was eating ravenously. Late during the week went to Car Max to sell his 2013 VW Passat. He was paid $20,000 since he didn’t owe anything on the car.

The rest of his financial picture which he willingly shared with me was much more complicated. He had maxed out three credit cards paying for three funerals, one burial, two cremations and one big wake type affair at the Italian Center in Bensonhurst to celebrate the lives of his mother, sister and aunt. He said he hardly knew any of the people who showed up except for teachers that he and his sister had at St. Francis Xaiver School or he had a Bishop Kearney High School.

Reg explained that he was able to access his aunt’s minimal assets since he was a co-signer on her checking account. He was surprised to find a $50,000 paid up life insurance policy that she finished paying for twenty years before. The policy was worth almost $75,000. His sister who was a teacher’s aide had nothing except a few thousand dollars in her checking account which was not enough to pay for her burial expenses and credit card bill. He didn’t have to tap into his own saving because his mother’s savings more than paid for herself and his sister’s cremation. Reg figured that after he paid to have the furniture carried off from his mother’s apartment he would have about $200,000 from his mother. What surprised him the most was finding a $50,000 whole life insurance policy that was not completely paid off but it paid the face value. By our account he wasn’t going to have to pay inheritance tax on the approximately $325,000 he had. He didn’t need the money so we discussed investing the money. Since I am a conservative investor I recommended several bond funds and several large cap funds at Vanguard. He agreed with my recommendations.

By the end of the week whenever we left my condo we held hands. Our plan was for Reg to go to Capri and get oriented. I would come later. He knew his uncle had a place for him to stay but didn’t know if it was big enough for the two of us. I felt comfortable enough with our relationship that I decided to retire. I knew it was going to take me some time to transfer my business to other partners. Reg and I texted on Whatsup and called daily but the calls were brief. He was working ten to twelve hours a day.

While I missed him terribly, as he said he did me, I calculated that I could make a smooth transition into retirement by August 1. He wanted me to join him sooner but I convinced him what I was doing was best. He did tell me where he was staying was tiny but he thought I would like it.

Harbor on Capri

Harbor on Capri

On the morning of August 2 I was on the ferry to Capri. Our plan was for Reg to meet my ferry and take me to our summer home. Approaching the mountainous little island felt like sneaking away from the old world into a brand new place. Before we docked I saw Reg in cut off shorts and provocative, sleeveless blue shirt with a low cut neck line. He was waving as the lines were cast to the men on the shore. I couldn’t wait to get my arms around him since I hadn’t touched he luscious body in three months. Without thinking we gave each other a deep kisses. No one seemed to pay any attention. We walked to the taxi holding hands. I didn’t want to let go.

Author’s note

This is where I planned to end their story. If you read it and want to know more about the story of Reg and John’s life together write me at I hope you enjoy reading the story as much as I did writing it.

I want to thank Don W for proofreading the story. I took the photos from the internet where there were no photographer credits. If any photographer wants credit let me know.