Lessons at Leather Bar

Today was going to be my first time to walk into a Leather Bar. Although in my 40s, these bars were always intimidating to me. But now, as I was discovering a leather daddy side to my sexuality, I was determined today would be different. Thinking back, I was not sure why I was so scared. I think in part it was because I was intimidated by the manliness of the clientele and feared I would be so obviously out of place, but also there was an awareness of how arousing the thought of these spaces was in my mind and did want to appear so desperate. But today I was putting that all behind me as I crossed over the dark threshold of the Tannery, our local gay leather daddy bar. 

In hindsight, it is not surprising that I am drawn to the strong, alpha types and that I had developed a fetish for smoking leather daddies. Having grown up as a mechanic's son, I was always surrounded by young testeroned fueled men that would come to my dad’s garage to work on their cars. He had all the tools they needed to repair and maintain cars. As a result his work buddies and their sons were always coming round whenever their cars needed some attention, and sometimes even when they didn't. So, I was raised watching these hyper-masculine men, covered in grease stains and smoking their cigarettes, bending over their favorite machine, talking shop. It was more than this closeted gay kid could possibly ignore.

For a long time, this fetish remained a thing of fantasies and porn. I married a nice man and have a great life, and although some might describe it all as vanilla, it suited me well. However things took a slight pivot when I was given my first cigar. A vendor I worked with on a large project gifted me a bottle of port and two cigars. Although I appreciated the port, I found the cigars a slightly odd choice. In this day and age, smoking was not something often promoted or encouraged. Yet I was also somewhat flattered that he saw me as someone who would smoke cigars. The idea that he thought I could pull this off pleased me. I put the port in our bar and cigars were stashed in the back of a drawer, almost forgotten. However one day when my husband was away for work, and I was alone with my porn, I decided I would also enjoy one of these cigars. After some quick online tutorials, I prepared and lit my first cigar. Although I had smoked cigarettes a few times, this was different, I felt an almost instant enjoyment to the heady and mouthful smoke of the cigar. It felt natural and also strongly arousing. It made me feel more confident, even slightly cocky. I liked this sensation, and it would become a guilty pleasure I seeked over, and over again. 

My husband was not a great fan of this new cigar fetish so it became a thing I would do when he was away or had quiet time to myself. As I explored cigars and this new cockier side to my sexuality, I also began to add other aspects, including leather gear and more facial hair. It was clear to me that I was starting to see myself more and more as the leather daddy that I previously fantasized about. I felt I pulled off the look well. It helped that I have kept trim and, with more frequent gym visits, was well toned. With my thick dark facial hair, which was slightly graying, a cigar in mouth and leather gear, I think I looked good for a middle aged man. However this remained something for my eyes only. So I soon realized that I needed to get out and start to explore this new world and connect with other like minded individuals

I knew that on Fridays, happy hour at the Tannery was for cigar smokers and I thought this would be a good time for me to go. With hubby out of town, tonight seemed like the right time to try it out. Not yet fully confident to leave the house in full leather, I put on jeans, boots and a leather shirt, a small nod to my leather fetish. For me tonight was about sharing cigars with other like minded men, and not about sex. I was determined that I would go there early, have a drink, smoke a cigar and chat with some other men who shared this pleasure. I told myself that I would leave early before things could get too wild. As I walked in, there were only a handful of men scattered throughout the bar. Most were smoking cigars but some were just chatting with those who did. I was a little surprised to see the men were not all dressed in leather, and some were in suits, and some even just in jeans and t-shirts. I realized that tonight was clearly more about the cigars than leather. I took a seat at the bar, and ordered a beer. I took out my cigar and the bartender was quick to ask if I needed a cutter or light. Although I did have these things, I took him up on it and allowed him to help me out. He was really cute, wearing a leather harness that show off his well chiseled and hair covered chest. I said thanks and he gave a devilish smile back. Clearly he liked what he saw and it made me feel good. I leaned back and sucked on my cigar and slowly exhaled as I watched him go back to work. 

The cigar quickly helped cut the nerves. I soon relaxed and enjoyed the moment and looked around the room. There were quick glances exchanged as I scanned the room. Most of the men were my age or older, which did not surprise me. As I surveyed the scene, the door of the bar opened, letting in a bright shot of light. In the doorway stood a tall man with broad shoulders. Although I could only make out his silhouette, it was clear he was a well built man. As he shut the door and my eyes adjusted to the light I could make out his dark hair and beard sculpting his chiseled features. He was dressed as I had always fantasized a leather man would be; a scruffy biker jacket, tight t-shirt hugging his pecs, jeans and black motorcycle boots. He looked like he just walked off the set of Tom of Finland. Although as he was carrying a helmet, I had to assume this attire was as much about his mode of transport as it was about his persona. As he walked in, all heads turned, many people waved, making it transparent that he was a regular here. He sat down at the bar, a few seats away from me. The Barman immediately poured him a drink without him saying a word. The guy took out his cigar, cut and lit it without missing a beat. He was smoking a large 7x70 asylum, immediately establishing dominance in the space. 

Watching this god like beast smoke his cigar was a sight to behold. The way he inhaled and held the cigar between his lips made me instantly hard. I tried not to stare but he was a beautiful sight that was hard to ignore. Noticing my attention, he locked eyes with me and signaled for me to scoot over. Without a thought, I got up and moved over to join him. We introduced ourselves and then started some small talk. To break the ice I asked him what Bike he was riding. He has a triumph scrambler. I knew this was a classic bike with bad arse reputation, not to mention a favorite of James Bond. He was impressed with my knowledge, for which I thank my years of growing up surrounded by gear heads. 

He told me his name was Mike. He mentioned he was in finance, which only spoke to the James Bond link. He told me he had been coming here for over a decade, but cigar night was his favorite… I told him I was new both to the bar and the scene. He just smiled and said I was natural and pulled it off well. As we chatted the talk became more and more flirtatious. Clearly he was quite the player and I think he saw me as a unconquered novelty. I tried to hint I was married, and really was only looking to meet some friends. Not sure he took the hint, as in my slightly tipsy state he clearly was not thinking this would be an issue. To be honest, given how hot he was, I wonder if he was right.

As I tried to change the subject, I quizzed him about the scene in town. He talked a bit about what it meant to be a dom leather master, and said he could teach me a few things. He told me, I needed to know who I was, and act appropriately. He said as a Dom he did not take no for an answer and he took what he wanted, when he wanted it. Then he pointed out that right now I seemed more like a pig than master. Shocked by his comment, I stared as he took a large inhale of his cigar and blew it in my face. I could not deny that watching him I felt less manly than I'd like and would honestly do anything he asked of me. So clearly he was right in this case. 

Luckily his attention was shifted as the door opened again. In walked a lean cute twink that turned everyone's head.. He whispered to me this was one of his boys. He said to watch closely as now he could show him what it meant to be leather daddy. The twink was lean with scruffy blond hair and thick beautiful lips. He had a boyish lean body and was wearing a slim harness and skinny leather jeans. He looked around the bar and then locked eyes with my friend and he immediately strutted over to us. 

He did not even look at me, just addressed his leather daddy and said, "hello sir, glad to see you". The leather daddy just grabbed him around waist, pulled him in close and kissed him. The boy just smiled. He introduced me and said "this is my boy thomas". Thomas just looked at me and nodded. Mike looked at me, ignoring the twink, and told me Thomas was regular here and always checked in on Friday to make sure his Daddy was properly relaxed after the work week. Thomas just smiled… and then looked at Mike with anticipation. I was not sure what was going on, but then Mike gave him a nod and said to him, "what was waiting for… don't mind my friend here." Thomas just smiled and then crouched down til he was between Mike's legs staring up in anticipation. Without missing a beat he unzipped Mike's pants and pulled out his semi-flaccid cock. He immediately brought it to his succulent lips and began sucking on the head, working the shaft with his hand as it slowly got more and more erect. I was a little taken aback but also engrossed by the scene before me. Mike had a beautiful 8 inch thick cock, that Thomas clearly knew his way around. I looked up at Mike as he gave a wry smile and took back his cigar and inhaled.

Mike then proceeded to continue our conversation, ignoring Thomas except to occasionally ram his head down and hold him as he inhaled his cigar. Although it was hard I tried my best to focus on Mike but was not easy. I noticed by the lack of attention he was getting from other patrons that this was a regular occurrence that they had seen before. He then continued to explain how true leather daddies do not ask for favors because their boys were all well trained. Thomas was his Friday boy who knew that he had to always stop by to take care of his Master before hitting the club. He also knew he could only hit clubs if his Master was satisfied and only if did not need him tonight. He smiled at me and asked me, "Do you think I need him tonight?". Before I could think, I mumbled, I hope not. He just smiled while pushing Thomas head down to the base of his cock. 

Thomas continued to work his cock as we talked. The scene before me was so intoxicating… I tried to hide how aroused I was but it was hard (literally). This bull of a man remained casual and seemed more focus on his cigar and our conversation than the hot twink on his cock. The confidence and cockiness of Mike, along with rugged looks was incredibly hot. After awhile I could see Mike's attention was shifting. He told Thomas if he kept it up he'll get his reward. Thomas looked up and smiled longingly with his big blue eyes as Mike pushed him down again. Mike began twitching as I assumed he was releasing his seed down the boy's throat. Thomas just sucked it up, not allowing a single drop get away from him. As Mike stopped, Thomas slowly took his mouth off his cock and gave it one more lick with his tongue to clean it up. Without missing a beat, Thomas stood up as Mike put his cock back in his pants. He kissed Thomas and told him, "have fun tonight". with that he smiled and walked out of the bar like nothing happened. 

I was mesmerized by what just happened. The casualness of whole scene made it seemed somehow unreal. Dream like. He the. smiled at me and said, see what I mean. I told him I had a lot to learn. He just smiled and told me he'd be happy to teach me. With that he took sip of his whisky and drag of cigar before returning to our conversation. I looked over at Barman who just gave me a knowing smile and wink. I knew that tonight was only beginning of my journey.