I was 18 and my then girlfriend and I had talked about it for a while. We decided it was cool to go for it. She had surprised me at work one day, by going down to the pharmacy and getting me a 3 pack. I was nervous but excited, and of course we did not want our parents to know. At least I did not want my parents to know, I think hers were cool with it. Now the only question was where we would go to try it out. In my car in the parking lot after work seemed as good a place as any to us, so that’s where we went. Just like all first times, this was new and I was not too sure what I was doing, but I did not care because I was having a good time. It wasn’t until a few months later that I had realized how much I was missing out on because of my eagerness to jump right in without fully knowing what I was doing.
I had decided to try smoking a cigar, but I had no clue what I was doing, so she had gotten me a pack of Dutch Masters from CVS. I figured “what the hell” I will try them. Of course I thought I was a big shot now. When she gave them to me, my initial thought was, well I have to go outside to smoke these because you have to spit while you smoke and I don’t want to spit inside. I was also ready to bite the end off because somewhere I thought I saw someone doing that. Luckily, most machine made cigars come with a convenient hole in them already so no cutting or biting is required. How far I have come since then.
The Shaggin’ Wagon
I did not know any better, so I continued to smoke Dutch Masters. Occasionally, I would spurge and buy one in a plastic tube too, but only on the nice nights when I was feeling special and wanted to celebrate. What I call my first real experience did not come until one of my closest friends, and eventually my roommate when I went to college, was on his way back to college. We went out that night with a bunch of guys, and some ladies too, to a drive in movie. Some details are so vivid and some are a blur. I remember what we went to see, but I don’t remember much about watching the movie. My one buddy drove a huge van, we called it the shaggin’ wagon, and we all piled in. Back then the movies were pay by the car not the person, so we jammed all of us into the van to save a few bucks.
Before I met up with them, I decided to grab a cigar at a local tobacco shop. It was time to step up to the big leagues, so I decided to look in their cabinet humidor for one. I remember it sticking out like a sore thumb in the shiny aluminum tube. It had the word Punch on it. I thought “I like flavored cigars and this one must taste like fruit punch, let’s give it a try”. Clearly I had no clue what I was doing. Luckily I decided to buy a $.50 cutter to go with it because I had checked to see if it had a hole in it like all the other cigars I had smoked and there was none.
What I actually wound up with was a Punch Grand Cru Monarch, and I am so glad I did. The experience was fantastic. It took me almost the whole movie to smoke that wonderful cigar. As I said, I don’t remember if I liked the movie or even watched most of it, but I do remember (still now) most of the details of that cigar. It was flavorful and cedary, light enough to be a good experience, but enough body to keep a seasoned smoker interested. Ultimately it was one of the most memorable cigars I have ever had. Now, I am sure if I went down to the humidor today to grab one, it would not be that magical to me, but I will always have the memory of my first real cigar.
Photos by Hugo90 and Faint Sanity
Great read, Jason. I think I lost my virginity to Swisher Sweet Wood-Tipped. There’s no thinking to it; I WAS cool =)
Of course it was, and you and I were bad ass back then. I think it is a rule to try something a little rough for your first so you can look back fondly and see how far you’ve come.
Cool stuff, Jay. Your writting skills are excellent, although I may be a bit baised being your dad. Keep up the good work. BTW, my favorite cigar is an Acid Blondie.
Hey dad! Thanks for checking this out. I like the Blondie too, but I remembered while i was writing this about one of the first cigars you and I had together. I bought you an Ashton Crystal for a birthday, I won’t tell which one, and we smoked them at the bar. That was a great time. Keep checking this out for some other articles, they are always informative. Spread the word.
It was early summer in 1957 and I was 14. My buddy had sneaked four Pacemaker perfectos with the new “hole in the head” from his father’s stash, and the four of us bicycled into the woods to play big shot gangsters. We lit off with those old paper matches, and while the others were hotboxing their cigars into two inch glowing heads, I had been talking and neglected mine for several minutes. When finally I remembered the cigar and took a puff the flavor was so incredible my mouth was watering for more. It was after several well spaced puffs when for the first time I felt my mind slipping into a new and very pleasant dimension that I realized what cigar smoking is all about. More than half a century has passed since that fateful day, and though I’ve smoked many thousands, I can taste like it was yesterday the ‘pungent creamy sauteed mushrooms in butter’ of that wonderful Pacemaker. Little did I know that would became the one cigar “by which all others would be judged – and found wanting.” -Amen.
Wow, Bob! Thanks so much for your comment… the only thing I have to say is that after reading your post, I’m not sure if I want a cigar, or a cigarette! LOL
I’m sure I’m not the only one that appreciates your passion for cigars… stop by any time and share your cigar memories with us!
~Ginger
Thank you Ginger. Over the years I’ve bought many pounds of pipe tobacco from Habana and often thought one of these days I ought to roll out Albany way and see where all this stuff is coming from. I live in Franklin MA and I’m thinking this would be a good year. Though I ride year round, it would be better to wait till the campgrounds open so I can sleep over and make it a two day trip. I know you ride, and I tip my helmet in respect to any lady who has what it takes to set out on her own. My current ‘beloved’ is a head turning maroon and silver Vulcan Nomad with a good deal of leather fringe. My riding son tells me from behind my bike looks like a street sweeper. I tell him there are times I wish I’d kept having daughters. Hope to get out Habana way sometime in early June. Ride safe Ginger, and watch out for them soccer mom’s with their cell phones.
Bob, thanks for the giggle @ “there are times I wish I’d kept having daughters.” hahaha! If you make it out this way, make sure to let us know, and you keep the rubber side down, Bob!
I tell you Ginger my three girls were the apple of my eye. I’m a bit artistic and having worked a great deal with colors, I delighted choosing my children’s clothes to coordinate with their hair and eyes. I got a lot of compliments over the years on the way they were dressed, especially when they were young. My little sweethearts. The oldest is now 43 and I am amazed how the years have flown. Due to the Surgeon General’s warning I left off smoking for 30 years. It was my son who started me back with cigars. The same son who started me motorcycling. Now that I think of it that boy’s been nothing but trouble. ( : {) Only kidding of course, my son is the best friend I have in all the world. Without him I wouldn’t be half the man I am today. When I get set up out there I’ll give the store a call and let you know I’m on my way. If you ride to work we might drop out to the parking lot for a fragrant bowl and kick a few tires.
I’d be happy to give you a tour! Not sure if I’ll be riding to work right away, but am always in for taking a smoke break
Bob, I will say you have a way with words. I felt like I was there with you. It is apparent even back then you understood how to respect a cigar to get the most out of it. So many people are way too rough with them and they wonder why it falls apart or tastes burnt. Ironically it was me that introduced cigar smoking to my dad, so there was no stealing from his stash. If you do make it out this way, I would love to meet you, and perhaps join you on a ride if i get my bike on the road this summer.
Now I knew straightaway you’re a good son Jason. If you check my response to Ginger above, you’ll see it was my son Peter who got me into cigars. Back when I was a lot younger, probably around age 12, there was a man who took the tickets at the entrance to the local beach. There was a neatness about this man that really stood out. His trousers always had a crease (back before permanent press), his shoes were always well polished, and he was thoughtful and chose his words well. I used to think when I grew up I wanted to be like him. Well, the image was pretty well shattered the day I came through the gate and found him sitting by the little white shack smoking a big smelly cigar. When I asked how he could put such a soggy thing in his mouth, he turned the head my way with a smile and said a man who appreciates cigars never, ever, allows the head get soggy. Sure enough Jason, though it was down a good two inches the head on that double claro looked as dry as when it came from the box. I was so impressed that I have never once chewed a cigar, and the head of every one has remained dry until the tarry nub was laid to rest. That man by the way, who was probably a college student though he seemed to me as old as my father, never knew the impression he made on that small boy, or ever dreamed that for a good 50 years every time he lit a cigar he would think of him and smile, and make damned sure he kept that head dry. Thank you for the response and your kind words. If I get to the store it will be a pleasure to shake your hand.
Ginger – now that I know the blends you like I’m marking my calendar to pack my last tin of Dobie’s 4 Square Green (English blend long out of production), and Mick McQuaid’s square cut (not available in the US). Be sure to have something to drink in hand, that last one has had grown men on their knees reciting the rosary.
It’s a very rare occasion to see me without a cup of coffee in hand, so we’ve got that covered!
I’m always up for trying a new and/or different tobacco, so that sounds great too… Russ has made it a mission of his to blend a pipe tobacco that would kick my butt on the nicotine level, but we haven’t found it yet so I’m looking forward to trying the one that puts grown men on their knees! 
[...] written by me for a different blog a while ago but I liked it so much I decided to bring it [...]
Too funny….
I started out with Swisher Sweets in High School nad when I became an 18-yr old father, I switched to “real cigars” and handed them out when my first was born – King Edward Churchills. It is amazing I ever picked up another cigar!