What Might Have Been

Jess decides to spend the weekend by himself, wanting to avoid the crowds and pressure of meeting someone. He watches a movie and an unexpected meeting change everything. Will this turn out better than the rest of his options, Jess certainly hope so.

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The same choices again, will Jess have better luck with his last option? The final chapter will answer that question and a few more. I hope you have enjoyed this story and like how it ends.


I got home from work on Friday night and had no real plans for the weekend. Well actually, I sort of wanted to go to the Cameo Theater. The Cameo is a local theater that shows old movies that are at least 20 years old. They always make it a big event and serve food and beverages from the movie that is playing. It usually brings out the true fans of the movie, and they encourage patrons to dress in costumes or as their favorite character from the movie. I drove by the week they were showing the original “Star Wars”, and I never have seen so many Chewbaccas in one place in my life.

This Saturday, they were showing “Brokeback Mountain”. I have seen it before, but never in the theater. When it was released in 2005, I was 5 and had no idea what it was about. Once I realized I was gay, it was one of the first movies I wanted to watch. I thought it would be fun to go watch it at the theater and I assumed there might be a lot of other gay guys there dressed as cowboys. I would probably just wear jeans and a button-down shirt. I’m really not into the whole costume thing.

As I was thinking about my plans, I checked the dating app that I was currently on. I had yet to actually meet with anyone that I had talked to. Honestly, I had only exchanged messages with three guys. The first two were just a couple of ‘what are you looking for’ type of messages. The third guy, Trent, and I have been talking for about two weeks now and were getting close to a possible face-to-face.

So far, Trent and I seem to have a lot in common. We were both 26 and still working at the first job that we had got after we graduated from college. We both lived alone and were from simple middle-class families. We had exchanged pictures and I thought he was attractive, he also told me that he liked how I looked. I had a new message; it was from Trent. He wanted to meet at the new Italian restaurant that had just opened. I did like Italian food, so now I had to decide between Trent and Heath Ledger.

Before I could reply to Trent, I got a text from my buddy, Jake. Jake and I have been friends since college. We actually dated for a few months, but we found we were too different to be partners. We were better suited to be friends. Jake was very outgoing and always made sure that everyone he met knew he was gay. I’m a bit on the reserved side, while I don’t hide the fact that I am gay, I don’t advertise it.

I read his text, “Headwind is playing at Jones Street Station tomorrow night. You want to go have some fun?”

Headwind is a local band that we both like, they are very talented and know how to get a crowd out on the dance floor. Jones Street Station is a nice bar that caters to the gay crowd, although a lot of straight people go there for the live music.

I sighed as I now had three options for Saturday night. Then I remembered I also had an invitation from another friend, Colby. I met Colby and his husband Ben a couple of years ago at Jones Street Station. Colby had a new coworker that he wanted me to meet. He suggested that I come to their house for dinner to meet Austin. I have never had good luck with blind dates, but Colby assured me that Austin was a great guy and that he was very good-looking.

Suddenly, instead of having no real plans for the weekend, I now had too many options.

I sighed as I thought about what I really wanted to do this weekend. I had a tough week at work and a nice quiet weekend to recharge sounded perfect. Meeting Trent would mean going to some crowded restaurant. The night out with Jake would be even more noise at a busy bar. While a nice home cooked meal with Ben and Colby wouldn’t be bad, it felt like too much pressure to like the guy they were introducing me to.

At least if I went to the movie, I could sit by myself and come straight home afterward. There would be no pressure, and I already knew I would like the movie. I let Trent, Jake, Colby and Ben know that I appreciated the offers, but I had other plans.

I let out another sigh of relief as I made myself some dinner, took a shower and then went to bed. The next morning, I busied myself with chores around my apartment, laundry, dishes, vacuuming, that sort of thing.

The movie was starting at 8:00, so I dressed and drove to the theater. Even though the theater encouraged its patrons to dress in attire worn in the movie, I just put on a pair of jeans and chose a simple button-down shirt. I really didn’t own any western wear, let alone a pair of boots or a cowboy hat. I’m sure there would be others dressed the same way.

When I arrived, there was already a small crowd gathered at the ticket window. Of course, many were decked out like cowboys, but as I had hoped, there were several dressed as I was. I was a little relieved. I bought my ticket and stopped at the snack bar to get a beer and some popcorn.

I walked into the theater and chose a seat that wasn’t too close to the front or too far back either. I also skipped the seats behind those that had someone wearing a big hat. There was about 15 minutes before the start time and the room was filling up fairly fast. Of course, most of the people coming in were in pairs or groups, so far I had only seen one or two other singles taking their seats.

The seat next to me was still empty. To be honest, I was hoping it wouldn’t be a full house so I would have elbow room. About 5 minutes before the show was to begin, I saw another single man walk in. Like me, he was carrying popcorn and a beer. I saw him scanning the room looking for a seat as he headed in my direction.

He was also dressed in jeans and a shirt similar to mine. I noticed that he certainly wasn’t unattractive. I decided that if someone was going to sit next to me, I was okay with it being this guy. My heart began to beat faster as he walked straight to the row that I was sitting in. I had left the seat on the aisle open.

He paused and gave me a smile, “Is this seat taken?”

My suddenly dry throat croaked out, “Yes, that’s a seat.” I swear to God, his eyes sparkled like some special effect in a cheesy rom-com. Then I realized what I said, I tried to regain my composure, “No, that seat isn’t taken.”

He chuckled, “Thanks.” God, he had a beautiful smile.

He sat next to me and held out his hand, “I’m Mason, it’s nice to meet you.”

I swallowed hard and shook his hand, “I’m Jess. Nice to meet you too.”

He gave me another sweet smile as we both took a drink of our beer and the lights went down and the movie began to play. We gave each other a quick smile and settled back to watch the movie. We would exchange glances every time a romantic scene would come on the screen.

When Jack and Ennis had been apart for four years and met again and shared a kiss, Mason moved his hand next to mine on the arm rest between us. I made no attempt to move my hand away and neither did Mason.

When the postcard that Ennis sent to Jack came back marked ‘Deceased’, Mason grabbed my hand. I held on tight for the rest of the movie, we both used our free hand to wipe a tear away. Looking around the theater, I saw the scene was having the same effect on everyone else too.

As the lights came up after the movie ended, Mason smiled at me and said, “I’ve seen this movie before, but there a couple of scenes that still get to me.”

I nodded, “Yeah, me too.” Neither of us had let go of the other’s hand.

Mason said, “There is a coffee shop just down the street. They serve a good cheesecake if you want to go, it’s my treat.”

I grinned, “I love cheesecake.”

We sat in a booth and for the first time, I got a good look at Mason. He was even better looking than when I first saw him in the dim light of the theater. He had light brown hair and the most perfect brown eyes. I swear I saw that sparkle again as we ordered our coffee and cheesecake. His sweet smile caused his cute dimples to appear.

Over the next two hours, we talked about our jobs, families and what we liked to do in our spare time.

Mason said, “I assume that you are single.”

I chuckled, “Yes, and I assume you are gay.”

He laughed, “Yes, single and gay.”

God, he even had a great laugh. Mason paid the check and we walked out to our cars. He paused when we reached my car and he said, “Is there a chance you would want to see me again?”

I smiled, “Yes. I would love to see you again.”

Mason grinned, “How about I make you dinner at my place on Friday night?”

I said, “That sounds wonderful.”

We exchanged phone numbers and Mason gave me his address. I drove home with a big smile on my face, and I could hardly wait until Friday night. I honestly didn’t expect anything like this to happen tonight but was glad that I decided to go to the movie instead of my other choices.

Of course, Jenna noticed my good mood, and I told her about Mason and our upcoming date. Jake called and told me that he had a good time at Jones Street and that he met a guy. I was happy for him and told him that I had also met someone. We were going to get together after our dates to let each other know how things went.

Since I knew Mason liked cheesecake, I decided to make one to take to his place on Friday. I hurried home from work on Friday, stopping to also pick up a bottle of wine to go with dinner. I took my shower and spent way too much time trying to decide what to wear. I chose a V-neck t-shirt and jeans; I wanted to keep things casual. I loaded Mason’s address into my GPS and arrived at the agreed upon time.

Mason smiled as he opened the door. He said, “Perfect timing, dinner is almost ready.”

I said, “It smells great, I hope this wine goes with what you made, and I made a cheesecake for desert.”

Mason took the bottle of wine and said, “This will go great with dinner. And did you say you made the cheesecake?”

I nodded, “Yes, I just learned how to make it. I hope you like raspberry.”

He smiled, “I love raspberry, please have a seat at the table.”

The dinner was excellent; Mason is a good cook. I could already picture us cooking together. I sighed to myself, dang it Jess, there you go again getting ahead of yourself. Just relax and enjoy the evening, take things slowly and let them happen naturally .

After we had our desert, Mason poured the last of the wine into our glasses. He said, “Would you like to move to the living room to a more comfortable chair.”

I smiled, “I would like that.”

As we finished our wine we continued to get to know each other better. Mason asked, “Can I ask how your coming out to your family went?”

I shrugged, “Okay, I guess. My parents weren’t thrilled, but they told me that they still loved me and once the initial shock wore off, they have been very supportive. My sister and I have always been close, so I had told her long before I told my folks. What about you?”

Mason shook his head, “Not well at all. I told them right before I left for college and they have not spoken to me since. My older sister still talked to me until she met her husband. Right after they first started dating, he made it clear that he didn’t like me and I was not invited to their wedding. My little brother, Jared, is the only one that still talks to me.” A tear ran down Mason’s cheek.

I said, “I’m so sorry.”

He forced a smile, “It’s okay, me and Jared get together every few weeks and always have a good time. We just don’t talk about mom and dad, and my brother-in-law can kiss my ass.”

I chuckled, “I’m not sure if it helps, but you now have a new friend. I think you’re a good guy.”

Mason smiled, “Thank you, a new friend is always good. And I think you’re a good guy too.”

We looked into each other’s eyes for a few seconds, then as if we were in slow motion, we leaned in until our lips met. We broke our kiss and again looked into each other’s eyes. A second later Mason was pushing me onto my back, and we were in full make out mode. He was an excellent kisser.

I don’t know how long we kissed, but I wouldn’t mind if it went on forever. Mason leaned back and smiled, “You are very good at this.”

I blushed, “You’re not bad yourself.”

Mason took a deep breath, “I normally don’t do this, and I had no plans to do it tonight, but would you like to go to my bedroom?”

I smiled, “I don’t do this often either, but I would love to go to your bedroom.”

Mason took my hand and we walked down the hall to his room. We started to kiss again once we arrived at our destination. Mason began to pull my shirt off, I had no intention of stopping him, so I lifted my arms. He dropped my shirt on the floor and ran his hands through the hair on my chest.

He sighed, “God, I love a hairy chest.”

I’m sure I blushed again. Mason allowed me to remove his shirt to reveal a smooth muscular torso. Just like the ones I always lust after when I watch porn. I guess we always like what we don’t have. I pulled Mason in tight against me, the feeling of skin on skin is a sure-fire way to get my motor running. We kissed again as we both started to unbutton each other’s jeans. There was soon a pile of denim lying at our feet.

We paused our kisses long enough to kick off our shoes and socks and step out of our jeans. We looked each other up and down standing there in just our tented underwear. Again, my hairy legs were in complete contrast to Mason’s nearly hairless ones. I could see nothing that I didn’t like about him.

Mason grinned, “Just perfect, you are just perfect.”

I swear, he was going keep me blushing all night. I sighed, “Not as perfect as you are.”

Our lips met again as we both pushed our underwear down to join the rest of our clothes already on the floor. Our hard cocks brushing against each other as we fell onto the bed, smearing our precum all over each other. At the same time, we reached for the other’s cock and began to stroke each other. Mason’s cock fit perfectly in my hand.

I couldn’t stand it any longer, I had to taste him. We repositioned ourselves into a sixty-nine and Mason tasted just as good as he looked. His precum was the nectar of the gods, each taste only left me wanting more. Mason’s oral skills were also very impressive; I was getting the best blow job I have ever had in my life.

Mason suddenly pushed me off his cock and gasped, “God, that was so amazing, you had me close to cumming. I want you to fuck me before I cum.”

I sure as hell wasn’t going to argue, I had been wanting some time with that sweet ass ever since I followed him out of the theater last week. I rolled Mason onto his back and pushed his legs up in the air. His rosebud bloomed like a spring flower as I began to drool. I wasted no time in diving in as Mason gasped, “Oh shit.”

That was all the encouragement that I needed, I sent my tongue into overdrive. I covered his hole with my spit and slobber until Mason was begging for my cock. He handed me a bottle of lube, and I coated my cock with the slick liquid. I aimed my weapon at its target and kissed Mason as I slowly pushed in.

Mason groaned as my nuts hit his ass cheeks. I slowly began to pump in and out as we continued to kiss. Mason had his arms wrapped around my back and his legs locked on my hips. We broke our kiss as we looked into each other’s eyes. Damn, those eyes are hypnotizing.

Staring into those eyes and the way his velvety smooth hole encased my ridged manhood was causing my juices to boil. I panted, “I’m getting close.”

Mason gasped, “Let me see you cum.”

I freed my cock from its warm home and gave it one more stroke and spilled my seed all over Mason’s cock and stomach. It was the biggest load I have shot in a long time. I smiled at Mason as I used my cum as lube to stroke his rock-hard member. I scooped up more of my cum and used it as lube for my hole.

Mason grinned when he realized what I was doing. I let his legs fall and I positioned myself just above his stiff dick. I lowered myself until I was fully impaled. His cock felt so good inside of me as I began to bounce up and down. Mason’s eyes rolled back in his head and he gripped my hips.

It only took a few minutes for Mason to announce his impending orgasm. I climbed off Mason and stroked his cock until it erupted like Old Faithful, adding his cream to what was left of mine on his stomach. We kissed until we were both completely out of breath.

I fell to Mason’s side and wrapped my arms around him. We spent the next few minutes looking into each other’s eyes again. I did tell you that I loved his eyes, right?

Mason smiled, “That was very nice.”

I returned his smile, “Yes, it was.”

He gave me a kiss, “We can take a quick shower and then if you want, you can spend the night.”

I grinned, “I would like that very much.”

After our shower, we cuddled together and fell into a peaceful slumber. I hope I’m not getting ahead of myself again, but this just felt so right.

5 years later

I woke up in a cold sweat after a slightly disturbing dream. I crawled out of bed and made my way to the bathroom and turned on the cold water. I leaned down to splash the water on my face, each splash taking my breath away. I grabbed a towel to dry my face as I stood up. When I lowered the towel, those sweet caring eyes and that sexy smile were reflected in the mirror behind me.

Mason asked, “Are you okay, Jess?”

I took a deep breath, “Yeah, I think so.”

He wrapped his arms around me and gave me a deep kiss.

I asked, “Have you ever thought about what might have been?”

He gave me a quizzical look and asked, “What do you mean?”

I sighed, “Do you remember the night we met?”

Mason smiled, “Of course, it was the best night of my life. Brokeback Mountain at the Cameo.”

I nodded and gave him a little smile. I said, “Well, I just had a dream about that night. I don’t think I ever told you that I had three other options that night.”

He furrowed his brow, “Okay, do you want to tell me what those options were?”

I smiled, “I had been talking to a guy on a dating app, and we were supposed to meet for the first time. Jake wanted me to go to Jones Street Station to listen to Headwind. Ben and Colby invited me to dinner to meet Austin, a new coworker of Colby’s”

Mason paused and finally said, “So what does that have to do with your dream. I also had some other options that night too.”

I said, “In my dream I went out with the guy from the app, then the day repeated itself and I went to the bar with Jake, and again the day repeats and I went to Colby and Ben’s.”

He asked, “Are you saying that you wished you would have done those things instead of going to the movie and meeting me?”

I shook my head, “Oh God no. I definitely made the right choice. Meeting you was the best day of my life too. It was just a little disturbing at how all the others ended.”

Mason asked, “What do you mean?”

I answered, “The guy from the app took all my money. The guy I met at the bar only wanted to party and he ended up killing us in a car wreck trying to outrun the police.” I felt a tear run down my cheek.

Mason wiped it away and asked, “What about the guy that Ben and Colby wanted to introduce you to?”

I took a deep breath, “He turned out to be an abuser and he beat me.”

Mason wrapped his arms around me again and held me tight. I felt so safe in his arms.

Mason said, “Jess, none of those things happened. You went to that movie and we met; we have been together for five years now. Who knows what happened to the guy from the app, I guess he probably found another poor guy to rob. Jake went to Jones Street that night and met Luke, you were his Bestman when they got married last year. About a month after we started dating, Colby and Ben told us that they were glad you never met that Austin guy. Remember Colby told us he was fired because of his temper?”

I nodded, “Yeah, I remember.”

Mason thought for a moment, “Do you regret any of the last five years?”

I said, “Oh God no. Why would you ask that?”

He said, “I guess I was thinking that you are thinking about what might have been if you would have made a different choice that night.”

I thought about it for a minute. Mason continued, “I have no regrets either. They have been the best years of my life, and you need to know that I truly love you with all my heart.”

A tear formed in my eye, “I love you too and would not have changed the last five years for anything.”

Mason wrapped me in another embrace and a sudden peace settled over me. Mason was right, none of those bad things happened and I did make the right choice that night. My life had turned out pretty good.

Mason asked, “Do you feel any better?”

I nodded, “Yes, I do. Thank you and I do love you.”

He smiled, “I love you too. I’m glad you feel better because next week, your parents, sister, my brother Jared and his wife are all coming to town for our wedding. Ben and Colby, Jake and Luke are all coming too. That is if you still want to marry me.”

I held Mason tighter, “God yes, I still want to marry you.”

The End


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