A Letter to a Younger Me
Dear Jack,
Hey, it’s me Jack, you, from 40 years in the future. You have just turned 18 and have your whole adult life in front of you and I wanted to give you some advice.
The first thing I want to tell you is to just relax. Do you remember what grandpa told you last year? Yep, that’s right. “Don’t take life too seriously, you won’t make it out alive anyway.”
I also want to tell you that you turn out just fine. I won’t lie and say that it was smooth sailing. There is going to be some rough times, you are going to make mistakes. It’s okay, you will learn from those mistakes. They will make you stronger; they will make you better. Don’t worry, everyone else is making mistakes too. Those mistakes are what make you the man you will become.
I know you are worried about the plans you have made for your future. You keep asking yourself if you have chosen the right college, if you have made the right career choice. Just remember, plans can change, you may find something that interests you more in a few years, and that’s okay. Never stop exploring your options.
Keep the fond memories of your childhood close to your heart, and don’t forget to enjoy your final year of high school…
***
I guess I had a pretty good childhood. My dad is the manager of the local grain elevator in our little town of about 5000. Mom works part-time at the local doctor’s office as a receptionist. She answers the phone and schedules appointments three days a week. It gives her time to be there for us kids whenever she needs to be. Another lady works the other days, and they are always trading days to help each other out.
I am the youngest of three children, I have an older brother and sister. My brother is six years older than me and my sister is four. I can’t say that I was unwanted, I suppose a better word would be unplanned. Mom and dad assumed they were done having kids when they had their boy and girl. I came along and changed their plans. My parents were loving and always there for me, even when my brother would rather not play with a little kid. Let’s face it, what 10-year-old wants to play with a four-year-old? My sister would just want to put make up on my face and fix my hair. Mom would just say, take your little brother along or, he is not a girl, don’t make him wear that make up.
It was fine though, by the time I started school, I was finding friends my own age to play with. Danny was one of those friends, by the time we were 10, we were best friends. Robby moved to our school at about the same time, and we soon became the three musketeers. We were always at one of the other’s houses and our parents were all friends too.
When we were at my house, we spent most of our time in the treehouse that my brother helped me build. That was the one thing that we did together, he always liked to build things. Of course, I was in awe of my big brother’s skills and tried to learn as much as I could from him. Dad also helped, mostly by bringing home old pallets from the elevator. He also made sure that everything was braced so it would at least be safe for us to crawl around on. Once we had the treehouse built, my brother was off to spend his time with his friends. At least Danny, Robby and I got good use out of it.
Danny had a small creek running behind his house. It was about three feet wide and maybe 10 to 12 inches deep. Of course, we knew there were fish swimming in it, and you would never be able to convince us otherwise. We fished for hours with no luck. Truth be told, we spent more time wading in the creek and ruining more than one pair of sneakers, much to the dismay of our mothers.
All of our time at Robby’s house was spent playing basketball in his driveway or throwing the football around the backyard. Robby was happiest when he was playing whatever sport was in season. Danny and I were just satisfied spending time together. We liked playing sports just fine, but Robby was definitely more athletic than we were.
As we got to Jr. High we all joined the basketball team, again, Robby was the star, Danny and I were just on the team. We had several other friends too, again Danny and I were just on the team to have fun, and I was glad to be able to spend time with my friends.
As we moved on to high school, we continued to play basketball and hang out together. We have outgrown the treehouse and creek but are doing all the things that other teenagers do. Robby and Danny now prefer to be called Rob and Dan, I completely understand. We all want to be as grown up as we can, after all.
One of those teenage things that we all started to do was to notice the opposite sex. Well, I should say that my friends were noticing. I was paying more attention to the changes in my male friends. Hair was growing in new places, muscles were developing, voices were getting deeper. They told us in health class that all those changes were normal and that we were becoming men.
I wasn’t sure why I wasn’t interested in the girls in my class. I started to understand when we got to the section in our health class that explained the difference between heterosexual and homosexual.
I kept telling myself that I was a late bloomer, soon enough I would start to be attracted to girls, I knew I couldn’t be gay. Even as Rob and Dan, as well as my other friends, began to date, I kept reassuring myself, I would date as soon as I was ready. Mom even told me the same thing.
I just agreed with my friends when they said that Carla’s boobs were nice or Jenny’s ass was perfect. First of all, they were good-looking girls, so they were telling the truth. The fact that I wasn’t more interested in the topic was really starting to bother me. I didn’t have anyone that I felt comfortable talking to about this.
Even though mom and dad were great, I wasn’t ready to discuss this subject with them. My brother was busy dating his current girlfriend and I knew he wouldn’t be interested. Sis was more worried about what color of nail polish looked best to care about my problems. I also knew Dan and Rob wouldn’t be the best people to talk to. I guess I will just have to work this out on my own.
I decided to keep quiet and act like all my other friends. I just did my best in my classes and joined my classmates at school dances and parties. I must have been playing the part fine, no one ever asked any questions and from what I could tell, they hadn’t figured out my little secret.
We were soon in our senior year and were trying to figure the whole college thing out. I wasn’t sure what I wanted to do. Hell, how does any 18-year-old know what he wants to do for the rest of his life? Sure, there were a few kids that had always known what they wanted to do for a living. Susan was going to be teacher, just like both of her parents. Travis always wanted to be a Marine, Kyle was going to be a veterinarian. There were a few others, but I never had that one thing that called me.
One year I thought I wanted to join the Navy, I even thought about going into law enforcement. Of course, mom shuddered at the thought that my first two career choices involved weapons of some kind. By the end my junior year, I was leaning toward accounting or business. I did like working with numbers and I was pretty good at it. I was even considering being a business teacher. Hopefully it will become clear to me during my senior year.
A few weeks after school started it was time for Homecoming week. This always ended on Friday with the football game, followed by the big dance. Rob was on the football team, but Dan and I were just happy to go to the games and cheer the team on.
The school voted on Homecoming Royalty and Rob and his girlfriend, Heidi, were elected king and queen. They had become the ‘it’ couple as soon as they started to date. Dan started to date Stacy over the summer and I was still single. This meant I was going to the dance stag. Dan and Stacy were nice about it and let me go with them.
As soon as we walked into the dance, Dan and Stacy wanted to dance. I was used to being the wallflower, so this was nothing new or unexpected. As I walked over to get some punch, Julie was also approaching the table.
I smiled and handed her the cup I had just filled; she smiled as she accepted the punch. Julie was a nice girl and while we weren’t really friends, we always talked and said hi to each other when we were in the same classes.
She said, “Thank you.”
I filled my cup and nodded, “You’re welcome.”
She asked, “No date?”
I shook my head, “Nope. You?”
She chuckled, “No, flying solo tonight.”
I clinked her glass and said, “Here’s to us singles.”
She laughed, “Maybe we could dance, if you want to?”
I shrugged, “Sure.”
I did like to dance; Julie was good-looking and maybe this is just the thing I needed to get my mind off of the other thoughts I was having. It was a fast song, so what would be the harm. When that song ended, the DJ started a slow, love song. Julie looked at me and I held my hand out. What the hell, we are at a dance, we might as well dance.
We ended up dancing every dance and I walked Julie to her car afterward. I even worked up the courage to ask her out on a date, she gladly accepted. Maybe I was finally ready to date, and I was normal after all.
After that first date went well, Julie and I were soon going steady, just like my friends. Dan and Rob were happy for me and even said it’s about time. We all went out to eat and to movies together. I must admit, it was nice not being the third wheel. Of course, we all went on dates alone too and I was happy that I finally had a girlfriend.
Julie had decided that she wanted to be a nurse. She signed up for a program with the local hospital; she could work at the hospital as nurse’s aide while she took classes. Basically, she was guaranteed a job as soon as she finished her training. The hospital even covered a portion of the schooling costs. We talked about what would happen when I left for college, I was going to a college that was about an hour away. We decided to try the long-distance thing, I would come home about once a month, and Julie said she could come see me on the weekends I didn’t come home. To two young people who thought they were in love, it all seemed reasonable.
We all soon made it graduation and were getting ready to start our adult lives. We tried to have a lot of fun in our last summer together. About a month before we were all going to be leaving for college, we decided to have a party. It was actually a farewell party for Travis; he was leaving for boot camp the following week. Julie had to work but she told me to go without her and have fun.
Unfortunately, I had been sick the prior week and was on medication and was told not to drink alcohol. We found someone to buy us beer, and we all agreed to be careful and not let the party get out of hand. I still wanted to go to the party, so I chose to drink soda. I guess if any of my friends needed a ride home, I could be the designated driver. Most of my classmates were there and I was not the only one who did not drink, so everyone had a sober friend to drive them home.
The one classmate that I was surprised to see there was Tommy Caldwell. Tommy was rarely at any school functions other than regular classes and didn’t participate in any extracurricular activities. He was an only child and his dad passed away unexpectedly when we were in eighth grade. Ever since, his mom became very protective and never let him leave the house without her. Because of that, I didn’t know him well, but he seemed like a decent guy.
Tommy really surprised us when we noticed that he really liked beer. Before long, he was really starting to cut loose and was becoming the life of the party. He was also the first one to pass out. We found a recliner and set him down, we also put a trash can beside the chair, just in case.
A couple of hours later, the party started to break up. Our sober friends all helped the drinkers to their cars and drove them home. Dan and Stacy were going to get a ride from me.
I chuckled, “I suppose I should give Tommy a ride too.”
Dan laughed, “Yeah, but he looks so peaceful laying there.”
I said, “Come on, help me get him to my car.”
Tommy woke up as we were walking him out the door, he was suddenly the quiet shy Tommy, again. He apologized for being a bother.
I said, “It’s okay, your house is right on my way home.”
I dropped off Dan and Stacy first and then continued on to Tommy’s house.
On the way, Tommy said, “My mom is going to kill me.”
I chuckled, “Do you think she will still be awake, it’s after midnight.”
He shrugged, “I hope not.”
We pulled into his driveway and saw there were no lights on in the house, he breathed a sigh of relief. He stepped out of my car and immediately fell down.
I got out of my car and walked around to help him up. I asked, “Would you like me to help get inside.”
He nodded, “I think that would be a good idea.”
He told me to go in through the garage, his bedroom was in the basement, and he could get down the steps without going through the house and waking his mom. I quietly helped him down the steps and found a family room with a kitchenette off to one side. I found the door that led to his room and helped him sit on his bed.
He said, “I’m a little thirsty, would you mind getting me a glass of water?”
I chuckled, “Sure, you probably should hydrate.”
I went out to the kitchenette and found a glass and filled it with water and returned to his bedroom. He gulped the entire glass down and let out a deep breath.
I asked, “Do you feel a little better?”
He nodded, “Thanks for bringing me home.”
I smiled, “You’re welcome. Are you going to be okay?”
He said, “Yeah, I think so. Can I tell you a secret?”
I nodded, “Sure.”
He swallowed hard, “I think you are really cute.”
I said, “Um… Thanks.”
He continued, "And you are really a nice guy.”
I think I was blushing now, “Thanks…”
He asked, “Do you think I am cute?”
I said, “Sure… You’re a good-looking guy.”
He smiled as he stared into my eyes. Before I could think of anything to say, Tommy grabbed me and pulled me in for a kiss. Julie and I had made out many times, but that is all we had done. I was suddenly surprised at how much I liked Tommy kissing me, it was a little different.
Tommy started pulling at my shirt and I wasn’t stopping him. He succeeded in getting my shirt off and his hands were roaming all over my chest and stomach. I was now lost in the moment and pulled Tommy’s shirt off. I had never expected Tommy to have such a nice body, I guess I hadn’t really paid much attention to him.
Just as any horny teenagers would do, we were soon kicking off our shoes and socks. Our pants followed a short time later as well as our underwear. We were now gripping the other’s hard cocks as we continued to kiss.
Tommy broke our kiss and said, “I have wanted to do this since our freshman year.”
He kissed my neck and then moved down to give my erect nipples a few licks. Holy shit, this is incredible. He left my nipples and continued his trek down to my nether region. I let out a gasp when he ran his tongue across the head of my leaking pole. When I thought it couldn’t get any better, Tommy took me into his mouth and started to suck. No one had ever touched my penis, let alone sucked it. Now I know why everyone likes a blow job.
The new sensations weren’t done. Tommy stopped sucking my cock and moved to cum-filled balls. I can’t decide what I liked better. Tommy helped me with that when he latched back onto my manhood and fondled my nuts with hand, rubbing a finger along my taint just for good measure. I let out a deep moan.
He looked up at me and asked, “Does that feel good?”
I nodded and said, “Yes, can I show you?”
He grinned, “Of course.”
We moved into a sixty-nine position, and I was now sucking my first cock. It felt so natural and I wanted to do this forever. We were playing with each other’s nuts as we sucked. I felt like I wanted more and I moved my finger under Tommy’s balls and then down to the crack of his ass until I found his pucker.
Tommy groaned at my touch and spread his legs. He panted, “Yes Jack, push your finger in.”
I did. It was so warm and tight. Tommy was moaning even more as he spit my cock out of his mouth and rolled onto his back, pulling his legs in the air. I worked a second finger in.
Tommy reached into his nightstand and pulled out a bottle of hand lotion and stuttered, “P-put your dick inside me.”
I was too far gone to argue. I spread some lotion on his hole and on my cock. I moved in between his legs as we looked into each other’s eyes. We kissed again as I started to push through the first ring of muscle. I paused when Tommy tensed up and took a deep breath.
He opened his eyes again and gave me a slight nod, I took this as the okay to continue. Tommy confirmed this by grabbing my hips and pulling me in as far as he could. His eyes went wide when I bottomed out, he let out a gasp. I pulled back and pushed in again and soon began to pick up speed. My instincts kicked in as I started to fuck Tommy with all my might. He only encouraged me with his moans and groans.
He panted, “I’m going to cum.”
I leaned down and once again locked my lips on his. My orgasm was quickly approaching too. Tommy dug his fingernails into my ass cheeks, pulling me in deep. We both exploded at the same time. When my spasms finally stopped, I broke our kiss and looked deep into Tommy’s eyes.
I asked, “Are you okay?”
He smiled, “Never better.”
We both sat up, neither seemed to know what to say next.
Tommy asked, “Did you enjoy that?”
I sighed, “Yeah, I have never done anything like that before.”
He chuckled, “Me neither. I was so glad you were at that party tonight.”
I suddenly realized that Tommy didn’t seem to be drunk.
He asked, “Can I tell you another secret?”
I nodded, “Sure.”
He took a deep breath, “When I got to the party, I heard you saying that you weren’t going to drink and would give others a ride home if they needed it.”
I said, “Yeah, I’m on some medication and the doctor told me not to drink.”
He said, “Well, I have never drunk beer before and to be honest, I don’t like it. I only took a beer because everyone else did. After the first drink, I just pretended to keep drinking it.” He chuckled, “I hope that plant that I dumped the rest of the beer in doesn’t die. I just kept going to cooler to make everyone think I was getting another beer, I carried that first can around all night”
I laughed, “You were pretty convincing as a drunk.”
He smiled, “I admit, everyone laughing at me was kind of fun. All through school, no one has ever really paid attention to me. I thought passing out would be a good way to not have to act like I was still drinking. I heard you guys saying how you never knew I was this much fun, it was kind of a good feeling.”
I said, “Why didn't you show this side you more often?”
He shook his head, “I didn’t think it would matter, my mom would never let me hang out with anyone anyway.”
I smiled, “We would have let you hang with us; you are fun guy.”
He returned my smile, “I was really glad when you offered to bring me home and help me to my room.”
I sighed, “Well, I never imagined something like this would happen, but I did like it.”
Tommy smiled, “I did too. If mom finds out, she will never let me out of her sight again.”
I asked, “Why did she let you go to the party?”
He said, “She didn’t. I snuck out.”
I quietly left after our talk, even more confused than ever. I thought I had put this whole gay thing behind me when I started to date Julie. The guilt washed over me, I did nothing to stop Tommy, in fact I encouraged it.
Was it really cheating on Julie if it was a guy and not a girl? Oh, who am I kidding, of course it is.
The next week, I broke up with her, telling her that I thought the long-distance thing would never work out. I know it upset her, and I have always felt bad about hurting her. I just couldn’t tell her the real reason, not yet anyway.
Even though I tried to call him a few times, I never heard from Tommy after that night.
***
…First of all, I am proud that you were responsible enough to drive your friends home after they had been drinking.
There are also a few other things you should know about that last year of high school.
You had not yet accepted your homosexuality; you were simply trying to fit in when you asked Julie out. You weren’t the first and you won’t be the last to do so. You shouldn’t feel too bad about how things went with Julie. Yes, she was heartbroken for a while, what teenage girl doesn’t think her first love is going to last forever? Just know that the following year she met a wonderful guy. They have been married over thirty years and have two great kids. She is about to become a grandmother for the third time. She has had a good life and when she thinks of you, she only has fond memories. You will meet Julie’s husband at your twenty-year high school reunion.
As for Tommy, that night was also a big turning point for him. His mom found out he snuck out of the house to go to that party. Seeing all the fun his classmates were having gave him the courage to stand up to her. He refused to let her keep him home any longer. Instead of staying in town to attend the small community college like his mom wanted, he went to a college two hours away. He embraced his gay lifestyle and met a nice guy. They have been together ever since; he has a good job and is living a good life. You will also see him at your reunion and meet his partner, you will remain friends with him.
You are getting ready to head off to college, remember to relax and just enjoy the ride.
To be Continued…
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