Cigar and Alpha Appreciation Society

Since our little triste behind the dumpster, Logan and I have only been able to communicate over text. Finding a time when my husband was out of town and that he would not be travelling seemed impossible. This only created a heightened anticipation of our meeting and served to intensify our text exchange. We had first met after a discussion over our mutual appreciation of cigars (and all things masculine) led to a blowjob in a dark alley (chpt 1). Given our shared love of cigars, whiskey and hot cars, and our intense sexual exchange, we jokingly said we'd start a Cigar Alpha-men Appreciation Society. Preliminarily our plan was to get together to smoke our favourite cigars and drink whiskey, and then see what happened from there. 

Given my husband's disdain for smoking,  the idea of having someone share a cigar was alluring. It certainly helped that Logan was a muscular older man, with rugged features, who drove a black mustang and was the epitome of every alpha male that appeared in most of my fantasies. Through our text exchanges, I began to think that there was more to the excitement of our meeting and my attraction to Logan. It dawned on me that his appeal to me could equally be a mix of wanting this hot stud, as much as it was envy of who he was. The combination of jealousy and attraction were an intoxicating combination that surprised me. The obsession was in part fueled by the fact he represented all things associated with alpha males, down to smoking cigars, which was an obvious draw for me, but the jealousy came from deeper within.  I realized when I too started to smoke cigars, I felt the kernel of my own desire to have his alpha confidence too… to be the guy that others would willingly serve.  I told Logan of my desire to be like him, and he said we'd work on that in our CAA Society. He was happy to bring me over to the alpha side. I couldn't wait. 

When the day came for our first meeting,  I was quivering with anticipation.  I was meeting him at his place at 5 pm. We planned to get some pizza, followed by cigars and whiskey, and see where the night would lead.  As I pulled up his driveway, I saw the garage door open. There was an empty parking spot next to his black mustang and a black Chief Dark Horse Indian motorcycle. This outward display of machismo was both off putting and ridiculously sexy.  I pulled into the garage with my Subaru Outback, which seemed out of place. Looking around the garage, it was neat but well stocked, which spoke to the compulsive gay mechanic he was. When the garage door started to close on its own, it made me look over the door frame near the back wall where I saw that him was standing. He was wearing tight jeans, black boots, a white shirt and a leather jacket. My cock immediately sprang to attention.  

He led me into the house. I watched his arse move down the corridor and listened to his boots click on his wood floors, which only made me more excited for the night ahead. Just before we headed to the kitchen. He stopped and opened a closet door in the hallway. Inside were a selection of leather jackets, harnesses, and jock straps, among other things. I tried to not hide my surprise at the boldness of introducing these items so early in the evening. He then told me “I was to choose which I was to wear for tonight." He cautioned me to choose carefully, "as that would tell me how the evening was to go ahead”. A leather jacket and boots told him that tonight was about alphas kicking back and enjoying some cigars and whiskey. He then smirked, and said, “after which we have some fun”, placing heavy emphasis on the “we”. This was clarified when he added, that “if I choose a harness, collar and jockstrap, then this alpha here”, pointing at himself, “was going to have some fun”. He finished off by saying, “the bathroom is behind you, I will let you decide”. Then walked into the kitchen.  

I immediately became hard. My dick was straining against my jeans as the reality of the evening ahead come into view. The decision seemed intense. Both options turned me on, and I could not decide which direction I wanted to go. I really wanted to explore more my alpha side, I was hoping this evening was going to be about us sharing some manly exploits, hangout as peers, but there was something about this man that made me think that was an unrealistic dream. It was ridiculous for me to see him as a peer, especially as I was so willing to submit to his every whim. As much as I see myself as a confident self-assured person, he had that manly presence that demanded respect. This was further amplified by the fact that he was someone people would be too scared to make angry, and maybe for that reason was the type that usually got what he wanted without ever raising his voice. The more I submitted to the power he had over me, the more I realized that tonight I would wear the harness and jockstrap. One concession I made was that I would not wear the collar. As much as I was willing to do all he desired, I wanted to make it clear I was not ownable but a willing participant. I was not sure he would notice the distinction I was making but it was important to me. 

I took the harness and jockstrap and went into the bathroom. I took all my clothes off and looked at myself in the mirror. I had done extra sessions in the gym this week and ate light today so my toned lean frame looked at its best. The harness fitted well and emphasized my shoulders and pecs, and the leather strap along the back had enough give for him to grip it. The Jockstrap felt cold at first against my manhood, which allowed it to soften a little as I put it on. I felt very cold and exposed being naked, with my arse out, but warmed up a little when I put my socks and boots on to warm up my feet. With nothing else to add, I took a deep breath and opened the door and walked out into the corridor and headed down to the kitchen. He was in there leaning against the counter with whisky in one hand and a lit cigar hanging from his mouth, oozing masculine energy like hot molasses. My dick knew I made the right decision as it strained against the jockstrap. He smirked, as if he knew that I would choose the harness, and then leaned forward over the island and asked if I wanted a beer or wine. As he was not offering me whisky or a cigar, I realized he was establishing his dominance in the space, establishing that some things were only for alpha men, which I was not. 

I took the beer, and he said, we should order some pizzas as we will be hungry soon. I asked him what he wanted but he said, he didn’t care and I could choose whatever I wanted. He handed me his phone, which was already logged onto his favourite local pizza joint. I started to scroll through the options and was not paying attention as he came up behind me. He stood so close I could feel his jeans against my exposed arse, and the heat of his cigar hanging from his mouth near my ear. It became hard to concentrate on ordering, as he looked over my shoulder, so I quickly made some choices. Once the order was in, he reached around and grabbed his phone and placed it on the kitchen island. As he did so, he leaned in closer and I could feel his cock bulging through his jeans rubbing against my arse. I froze as the intensity of the moment made me weak. He said we have 45 mins before it will arrive. With that, he pushed me forward so I was leaning against the island, and pushed my head down so it was resting against the cool granite. I wanted to express my shock but kept quiet. He then put his other hand, with the cigar between his fingers, on the counter near my face. This gesture seemed intentional, there for my appreciation, knowing my fetish and establishing his manliness in this situation. He then leaned down over my form and whispered in my ear, “sir is going to need to build up his appetite" and he made it clear, "I was going to help him”. This was a statement not a request. 

With that, he stood up again, lifting the cigar hand back up to his mouth, and took in an inhale. As he exhaled the smell filled the room, making me even harder, straining in the jockstrap. He then released his other hand, from my head, but I did not move. I then heard him grab his whiskey glass. He then swirled his fingers in the liquid and then brought his thick whiskey-soaked fingers to my arse. As his fingers explored my rim, the cold alcohol had a slight burning session which made me squirm. My movements only made him become more aggressive with his probing, adding more alcohol and starting to ram his fingers further in my hole stretching me. He then pulled his fingers out, after which I felt cold liquid run down my back, and onto my arse as he tipped the remaining contents of glass all over me. The ice cube on my back made me twitch. I then felt him lean in and spread my arse with his hands, as he started to clean up the whiskey with his tongue, paying special attention to my hole. He aggressively lapped up every drop of the whiskey driving me insane with anticipation. My pucker was begging for more. I then heard him unzip his jeans. I knew from our previous experience that he had a large eight-inch cock, and this was going to hurt. Within seconds, I felt him guide his cock head to my arse, which was still twitching with anticipation. Thanks to his previous efforts with his fingers, he could slowly guide the head into my anticipating hole. I winced as my arse stretched, but he was slow and gentle. When his head was in he stopped, and took a deep inhale from the cigar. Giving me time to get used to him in me. Then after he exhaled the smoke from the cigar, he slowly pushed a little further, inching into me, stretching me more and more. The pain was excruciating but I did my best not to show it and leaned into the pain, taking deep breaths. Once he was balls deep, he bent into me, cigar dangling from his lips, and he whispered into my ear, that I better get ready. He stood up, grabbed my harness and pulled me up and pushed him deeper into me. He then started to ram my arse like a piston. His pounding was intense, between his pelvis on my arse checks and the cold granite in front, I knew that I was going to be bruised. Not to mention the strain on my butthole, but this seemed irrelevant given the ecstasy of the moment. 

This aggressive fucking I was getting, was further intensified by the fact it has been over 10 years since I have been a bottom. With each thrust he drove his cock deeper and deeper into my arse, using the harness to hold me. He then changed gears, as he kicked my legs apart further spreading my arse, and then used one hand to grab me around my waist, and the other to hold my head down, and continue ramming into me. His cigar was firmly held between fingers on his hand on my head, its smoke was intoxicating, focusing my attention away from the raping my arse was receiving. As his rhythm shifted up a gear, and grunts become more aggressive, it was clear that he was close. I knew that I wanted to taste his seed, and with this, I asked him permission to cum in my mouth. He smiled, pulled out, and then grabbed me by the harness and dragged me to my knees. He took his cock and rammed down my throat, fucking my mouth with the same intensity he fucked my arse. It did not take long before I felt his cock twitching between my lips. He was close, I then heard a primal grunt as he shot his seed deep down my throat, pushing my head down on his member. I resisted a little and pulled back so that I could get his head on my tongue, allowing me to taste him as he continued to shoot streams of semen into my waiting mouth. With each load, he becomes more and more relaxed, as he released his seed. With my mouth full of his bounty, I sucked his head as I swallowed each load, paying full attention to his cock head. When he was done, he pulled out of another eager and satisfied hole, he then grabbed me by harness, pulled me up and kissed me. His tongue explored my mouth, tasting the remnants of his cum. Once done, he released me and told me to clean up and get dressed as pizza will be here soon. When I came back to the kitchen, he offered me a whiskey and told me to select an after-dinner cigar for us to enjoy. With that, I knew the night was not over.