Posts Tagged ‘cigar’

Okay so last time he had just stuck the stogie in my mouth. I was tasting my first puffs of premium cigar smoke and it was good! I took lots of quick little puffs, as if concerned about it being all the way lit, the cigar moved up and down in my mouth. I saw it jutting way out in the middle of my peripheral vision, and thought, hey, wow, I’m smoking a cigar. And I LOVE IT! Joe smiled at me and chuckled a little, this action angling his cigar up and jiggling it, and after a long, contemplative draw pulled the cigar out of his mouth and said through a cloud of fragrant smoke, touching my shoulder “c’mon, let’s go.”

We drove around town and saw the sights of the beach and the rest of the town, which took about an hour (since it’s kind of a small town and we weren’t stopping anywhere ). I felt excitement at finally meeting and smoking with him simultaneous with feeling… just so comfortable with him. We enjoyed each other’s company, he gave me pointers on how to smoke my cigar, told stories of his experiences that I was all ears for, and encouraged me in my college studies and career goals that I talked about. In a strange way, it was almost… fatherly, as twisted as that may sound, or like a big brother. At the same time we were on the same level, buddies.

Sometimes Joe held his cigar in his hand along with the steering wheel, but more often, due to needing his hands free for driving, he had it clenched in his teeth. Though I found cigars attractive overall, I especially found it hot when a guy had it in his mouth with no hands. Though the car’s windows were down- it was a nice July afternoon with some clouds in the sky, so it wasn’t sweltering- it was getting pretty smoky in the car. But it was an environment I liked. Throw in us wearing suits and drinking beers (or maybe, I thought, later Joe will introduce me to a “man’s drink” like Scotch) and it would be perfect. 20 minutes into the ride I finally got a long enough ash and he counseled me to tap it off into his car’s ashtray. I was happy to follow my big bro’s instructions and absentmindedly wondered if he would have any instructions of a… different nature for me later.

Finally we got back to the hotel- as Joe had reassured me, it was smoking-friendly, apparently more and more a rarity in this day and age- “can’t a man kick back and puff on a good cigar in his hotel?” he complained, although somewhat jokingly.

I made a suggestion: from the car to the hotel room, the cigars never left our mouths, we puffed all down the hallway, leaving a trail of smoke. Smoking cigars kicks ASS!, I thought. A few people gave us dirty looks, but I didn’t give a fuck, we were badasses! I felt like my cigar was carrying me along in a cloud of confidence and manliness! Me and my buddy Joe were invincible with cigars in mouth!

In the hotel room (fortunately, a smoking room, of-fuckin-course) Joe indicated an ashtray I could put my cigar down in- my long-ass cigar had only been half-smoked! No sooner had I put it down and blown out an epic cloud of smoke from my most recent puff than suddenly Joe pulled me to him, cigar in hand, and kissed me passionately. I was surprised, but very pleasantly. Neither of us had specifically talked about romantic overtones of our friendship before, but it was clearly boiling under the surface- as evidenced by all the compliments back-and-forth online and in person on our ride.

He chomped his stogie back in his mouth and opened a suitcase (he had checked in before meeting me) and handed me a pair of swim. “Here Doug, why dontcha’ put these on?” he said around the stogie chomped in the center of his mouth, which jiggled with every word.

I swallowed. Today’s surprises just kept coming. It was one of those barely boxer-brief-sized swim trunks that were navy blue with a white edge and a few white stripes down each outer side along my thighs. I went to change in the bathroom, looked at myself in the mirror and felt sexy in it, except a little embarrassed about my slight gut.

I came back out into the main room and Joe had changed, and I feasted my eyes on his uncovered torso for the first time. He had a six-pack and well-developed pecs, but more importantly to me, a V-shaped torso, with big wide shoulders going down to a comparatively thin waist. Not to mention his thick neck that evoked stereotypes of football players or musclemen. And, to top off his body which was like a tower of manly beauty, his black high-and-tight with gray temples, dark brown eyes you could get lost in with just a few barely noticeable crow’s feet, and, jutting out of his mouth, right above his strong square chin, his smoldering stogie, still jutting about 6 inches upward and outward from his mouth, and its round shape seemed to fill it just right. He smiled as I walked back in, his cigar angling further up as he did. I shyly put my hands over my stomach.

He reassured me that he had his pick of guys back north, but he was here to see me, and I was good-looking just the way I was, but if I was interested he said he could help me work out and get the body I wanted.

I said maybe so, not thinking how he would do that if he didn’t live here.

He saw my boner- couldn’t help it- and said in a low, growling tone, “I wanna touch you, buddy”.

I nervously whispered, squeaked more like, “ok” and he put his meaty hand at the small of my back, and slid it into the top of my trunks, reaching down until he was holding onto my left ass cheek. He squeezed it a little. His face was about an inch from mine, the cigar clenched in his mouth held out to the side, nearby my ear. In my peripheral vision I could see the ash glow orange as he puffed it in the somewhat dark room. I could feel his fingers under my trunks slither toward my ass crack. I was so excited, I could barely move.

He said, “ok what, kid?”

I ventured to guess…”okay, sir?”. This was really exciting. Smoke from his cigar was curling in the small gap between our faces and I coughed a little. I tensed up briefly, then relaxed as I felt one of his fingers touch my asshole, then slowly enter.

“Yes sir. You say ‘yes, sir’, to me, kid.”

“Yes sir”. The first knuckle of his finger had passed into my asshole and then the second.

“You’ve got a nice ass, kid. Nice and round. A bubble-butt.”

“Thank you sir.” I opened my mouth a little and he puffed cigar smoke into it. I savored it a moment and puffed it back out.

He started to put the tip of his middle finger in me! I didn’t protest or anything, I loved it and wanted more! The cigar was way over in the corner of his mouth; with the rest of his mouth he carefully kissed me. With his free hand, he took the cigar out of his mouth and put it in the nearby ashtray. A third finger entered me. Then he slowly shoved all three fingers in deeper, until he was almost at the bases of the fingers.

“Nice, tight but flexible, hole” he mused, grinning. He took a beer from the table next to him, the same table with the ashtray. He must have got it out of the hotel room fridge and opened it while I was in the bathroom changing. He took a swig of it. I was still standing right up to him with his fingers in my ass. “Want some, boy?” He held the top of the bottle up to my face and sort of caressed my lips with it.

“Yes please, sir.” He poured some into my mouth and I eagerly swallowed. I had never cared much for beer but now that it was being offered by this man it was like nectar of the gods. He wiggled the fingers in my ass. He took another drink and as he swallowed, contemplated me. He laughed a little. He grabbed my cigar from the ashtray and put it in one corner of my mouth, then poured more beer in the other corner. “Let’s see if you can handle both at the same time, little buddy.” I could, but almost dropped the cigar out of my mouth. I clenched it tight and took a puff. He said, “if you don’t mind my saying so, you look good, so hot, better than your pictures even.”

I said, “thanks but you’re the hot one. Your body is in such good shape.”

“You like my body, kid?”

“Yes sir.”

“Well wanna see more of it?”

“It would be an honor, sir.”

“Are you sure you want to see the rest of me?”

“Hell yeah, sir!” He rewarded my eagerness by moving his fingers suddenly in my ass, which felt awesome. I gasped. Then he took them out, which was disappointing.

He said “on your knees, buddy.” I obeyed, even though I was a little nervous about what I expected next. I’d only sucked dick a few times and wasn’t really into it, thought it was gross, though I did like receiving it! However, at this moment, I felt I wanted to do whatever would please this hot, authoritative man! He pulled down his own trunks and put his hand on the back of my head. I contemplated his 9 inch cock, thick around as a beer can, it was a little hard already. He said, cigar back in his mouth, “suck it.”.

I sucked and sucked, loving how his dick felt in my mouth, how it tasted, the heights of ecstasy I was bringing Joe to as indicated by his gasps and moans of pleasure and the ever-increasing hardness of his dick. I bobbed my head up and down on it, careful to always cover my teeth with my lips. This was amazing! I was so absorbed with giving Joe the best damn blow job ever nothing else mattered.

In this moment the most important thing in the world was just to suck, and suck, and suck…. His meaty hand on the back of my head guiding me, his groans got louder and louder and closer together. After about 10 minutes he pulled it out and I felt warm liquid squirting all over my face. Joe sat down on the edge of the bed, grunting, “good job, buddy. Good fuckin’ job” No one had ever facialed me before! Usually they pulled out and jizzed on their stomach. However, if any man was going to do this to me, I wanted it to be him. I had always thought of facials as kind of degrading, but as he walked me over to the bathroom mirror and I saw myself, I felt a satisfaction deep inside like I had never known before.

All the jizz covering my face in spurts across my cheekbones and across my forehead, some dripping down my nose and out of the corners of my mouth, some even dripping down the back of my head or down my neck- it was like he had marked me as his territory, and I was proud to wear this man’s cum! It felt like the ultimate reward for the great job I had done and all the pleasure I had given him. As we looked at ourselves in the mirror, he put his left arm around my shoulder and pointed at my jizz-soaked reflection with his right hand while simultaneously holding his cigar. “Y’know, buddy, I always thought you were cute, but now- (put the cigar back in his mouth)- you’re beautiful.”

I came spontaneously all over the mirror and counter. I had never felt so good in my entire life.

I wake up after six long hours of restlessly rolling around and sleeping on the carpeted floor all the while you sleep so sweetly and soundly in a Queen sized bed that’s big enough to hold at least four people. I don’t dare wake you yet as I remember the list you have given me with chores to do before waking you.

Six hours earlier as I’m kneeling on the floor beside the bed and succulently kissing each of your feet you hand me a list and tell me they are things I must do once waking up before I am to wake you in the morning. As I finish kissing your feet you pet my head and say, “Good boy but now you must sleep on the floor little piggy with no squealing while I sleep in this nice big bed.” Now here it is six hours later and I’m beginning my chores list. First I crawl to get your newspaper then I crawl to the kitchen and make you breakfast of eggs, bacon, and toast along with a caffelatte.

After fixing breakfast I put the food on a tray along with your newspaper, cigarettes, and an ashtray (just in case you need it but think you might use something else instead) and carry it to your bedroom where you are so peacefully sleeping. I set the tray down on the little nightstand beside the bed and go to the bathroom beside your bedroom to draw your bath water. As the tub is filling with water I return to you and begin kissing your feet to wake you up. You roll around a few times and then wake up smiling down at me as you point your finger to the tray so I come around get the tray then place it next to you on the bed. I kneel beside the bed as you are eating and occasionally you will throw some scraps of egg or bacon on the floor and point at it for me to clean it up.

After you finish eating you toss me your lighter. As you put a cigarette into your mouth I bring the flame up to your cigarette and hold it steady to make sure it is properly lit. You smoke for a few minutes letting an ash build up on the cigarette before ordering me to open my mouth. I open my mouth and you drop the ash on to my tongue letting it burn and singe my tongue causing extreme pain for my tongue. You tell me to swallow the ash and I do. This continues for the next several minutes until you get to the end of the cigarette and then you stub out the butt on my tongue. You order me to chew up the cigarette butt and then swallow it. I chew it up and swallow it, it tastes a little yucky but I don’t dare say a word.

You now sit and relax reading your newspaper as I go finish the bath water. I come back and tell you the bath is ready. You go to the bathroom and get undressed. You then get into the bath as I kneel beside it. You hand me a sponge and point to your feet. I begin massaging your feet with the sponge and slowly work my way up your legs and then as instructed up your entire body making sure to get every part of it cleaned. After you have been sponged down you get up out of the tub and dry yourself off with a towel but point to your feet again and I bend over to kiss them and suck each one dry including the toes.

Finally we go back into your bedroom and as you get dressed you inform me we have such a busy day planned for today. You are dressed in a Female Military Officer’s Uniform from WWII complete with leather boots and leather gloves. I am dressed in a business suit with a dog collar around my neck which has a leash attached and you are holding the end of the leash in your leather gloved hands. You drag me along with you into the garage where you unhook the leash from my collar as you order me to open the door on the rear passenger side which I do quickly without hesitation. As you sit down in the relaxing black leather seat of your black Mercedes S65 you throw me the keys and order me to drive. I get into the driver seat and start up the car when you tell me we are headed to the office this morning. About 20 minutes later we pull up outside the office building and I begin to have flashbacks to the last time you wore the Officer’s Uniform when we were here at the office.

Two years prior, James Alexander is a successful businessman. He has been the owner and CEO of Alexander Insurance Agency for the past 30 years. His company makes him over $15million annually in profit. Now at the age of 55 he is beginning to think about retirement and finding himself a younger woman to marry and have a family with. He has no living relatives and he has never married or fathered any child which is now beginning to bother him as he wants to pass on his business to someone that is family. When it comes to relationships with woman he has always been somewhat submissive and feels the best potential partner would be a strong independent woman that enjoys domination of a sub.

He decides to post an ad anonymously in the classifieds section of the local newspaper. The ad reads: “Wealthy 55 year old submissive male seeks young Dominant Female for marriage and to create a family with children. I’m 6’2″ and weigh 190lbs; my hair is short and grey. I am the owner and CEO of my own business. The female I seek must be younger then 30 and older then 21. Preferably she will have a Business Degree and might have an interest in running the family business some day. Also as I’m a cigar smoker would be nice if you are a smoker too or you should at least be tolerant of smokers. If you meet these requirements please reply to box 123.”

After several weeks James finally receives an email from a young lady who is only 24 years old and she calls herself Goddess Helena. In the email is a photo of her wearing a Female Military Officer’s Uniform that appears to be an older style almost like WWII German Uniform. Her outfit is completed with thigh high leather stiletto boots and full length leather gloves. Also in the photo she is holding a burning cigar in her right hand. She has long flowing blonde hair and is very striking figure in the photo, James can’t believe his luck as she appears to be the Goddess he is looking for.

She asks for him to reply with photos of himself along with his personal details such as his full name, address, business address, home, mobile, and business phone numbers and also to send proof of his income as she won’t consider anyone that makes less then $10million a year income. She explains that she has a Business Degree from the University of Texas and has always dreamed of owning her own company some day. She goes on to explain that she is accustomed to living the high life and she expects her slave to provide for her very expensive tastes stopping at nothing to please her.

She talks about the fact that many people have called her a gold-digger because of how she seeks rich older men for relationships and then uses them and has them buy her lots of gifts and expensive things. She explains that her taste in older men is because they tend to have the ability along with the desire to do anything to please her which includes buying expensive gifts for her, taking her on exotic vacations, providing her with high dollars for weekly allowances, and they also are experts at giving her good orgasms by eating out her pussy, taking her strap-on up their asses and getting a thorough fucking, cleaning her boots, eating her cigarette or cigar ashes, and just being submissive to all her sexual needs.

After reading her email James knows that she is the one as they have so many shared and common interests. So he begins to compose an email to her providing her with all the details and information she has requested. He also goes on to explain in his email a dream scenario that he has always hoped to act out with a Goddess such as her.

His reply email reads:

“Hello Goddess,

Thank you for your email. It was nice to read about your interests and I also found your photos to be very intriguing as well, it appears we have some common interests. Don’t worry Goddess I’ve attached documents with all of the information you requested including that of my personal financial details which I’m sure will satisfy your minimum income requirements. As I was reading your email and looking at your photos I couldn’t help but imagine myself kneeling on the floor of my office before your divine power. You are sitting in my executive leather chair and are dressed in the Military Officer Uniform from the photo along with the black thigh high leather stiletto boots and black full length leather gloves. Your long blonde hair is smoothed up into a ponytail as you swivel back and forth in the chair.

As I’m kneeling there, you reach on to my desk to pick up the gift I have bought for you a CAO Gold Maduro Double Corona which happens to be yours and my favorite cigar. You examine the cigar to make sure it has been properly cut and prepared for smoking. You then place the cigar to your lips as you toss me a lighter. Immediately I reach up with the lighter and light your cigar as you twirl it around with your magnificently beautiful lips making sure to get an even smoke.

While relaxing in my old chair which is now your chair and enjoying smoking the cigar you begin to interrogate me for information on my company’s assets and all my bank account passwords. When I refuse to provide the information you torture me by using your riding crop against my back and whipping me mercilessly. When I still won’t give you information you burn my flesh with the hot cigar. Then you force me to open my mouth and eat your cigar ashes.

After enduring the whippings and cigar torture I’m ready to talk and give you vital information on my company’s assets along with my bank account passwords. After providing you with the information that you required, you access my bank accounts and transfer all money from them to your own offshore bank accounts. You pull out documents from your briefcase and force me to sign an agreement giving you power of attorney over my affairs as well as transferring all of my assets including my company to you. You also make me resign from my position as CEO and sign papers making you the new CEO of the company.

You tell me that I’m now your slave as I am no longer the CEO of a company and have given you CEO power of my old company along with full control of my assets and power of attorney over me. You explain that as your slave I must always address you as Goddess Helena. You also explain to me that my first order of business as your slave is to fire my old secretary as the old hag will no longer be needed since you are CEO and you will use me your slave as your secretary. I call my old secretary Mary into your office and explain to her that she is to clean out her desk immediately as her services are no longer needed in your company.

Now that I have gotten rid of the secretary you tell me my next order of business is to come and clean your leather boots. I say, “Yes, thank you Goddess” and begin my task of cleaning your boots. While I’m cleaning your boots I hear you opening your briefcase that sits on the desk and rummaging through it for something. I begin to look up to see what you are doing but stop as I hear you say, “No, no slave you must not look up and must continue to focus on my boots as you clean them.” After a while of my tongue lapping over and over them, your boots are now clean to a gleaming shine.

You grab my chin lifting it up so we can make eye contact and as our eyes meet I also see a big black strap-on in your hands and wonder if it was what you sought within your briefcase. You smile a knowing smile at me as you pet my head. You run your fingers through my grey hair and say, “Good piggy but now your Goddess has a special treat for you since you’ve been such a good piggy.”

Suddenly, i feel something strike the back of my head and hear an angelic voice saying, “Wake up you fool and watch where your driving.” “Yes, Goddess Helena” is my response. i begin to focus my eyes back on the road and driving Goddess Helena to her company so that she may do whatever it is she needs to do in the office. i can’t help but wonder what will happen next.

June 2018
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