Smoking Blues

"Hey Bren," called my assistant Sarah. The home office called while you were out smoking. You Better call Mr. C back. He didn't sound happy!"

"Okay, thanks dear. I will call him back straight away," I replied as I headed to my office. As I was opening my door Sarah continued. "You know, you really have been taking a lot of smoke breaks lately. We are all concerned about your health. You are the first boss we have had here that knows how to treat people properly. We sure don't want to lose you."

"Thanks Sarah, I will see if I can cut down a bit."

I went inside my nice corner office, kicked off my heels and called Mack at the main office. He just wanted to go over some reports and was pleased with the results. But, before hanging up he said it was the 3rd time in a month that I was out for a smoke when he called. He warned me that the company was considering a no-smoking rule for all employees soon so I might want to consider giving them up.

I thanked him for the heads up and we ended the call. I sat back in my comfy chair and thought about it a little. First Sarah mentions my smoking, then Mack. And my wife has been on me for years about it. There was also the money issue. 4-5 hundred a month. That was serious cash.

And if the company pushed the issue I would have to make quitting work this time. I kinda liked sucking down a nice smoke. Especially after eating. But lately I seemed to smoke not just after eating a meal, but anything. A candy bar, a nosh of cheese or chips and dip. Maybe it was getting to be too much.

I only had a few years to retirement, and this company has been great to me. I am paid very well. I have a sweet private office and great employees. And I have been able to feel free to dress as any other woman that works here would. Not a bad gig for a 60 year old tranny.

Yes, I started switching my clothing slowly from male to female over the years. Even slowly increasing my bust size from flat to a small c cup over time. My wife supports my dressing and is always buying me pretty clothes and jewelry. My nails are long, dark red acrylics, and my makeup is always just right for the office.

But, don't get me wrong. I was never one of those pretty faced guys that could easily pass as a woman. I am more of a homely old lady due to my masculine features. Over the years I have learned to act natural and draw attention away from my face.

Of course my wife lets me dress for work, as long as I am her sissy slut at home. What a great life. Maybe I will talk to her about the smoking at dinner tonight.

"Hi Miss Carol, I'm home hun."

Carol was having a glass of wine and watching the evening news when I got in. I gave her a quick kiss and went to the bedroom to change. A short pink satin skater skirt and top, my apron and 4" matching heels. I started preparing a light dinner and poured a glass of wine for myself. I put the salmon in the oven to bake, started the rice cooker and went to my "sissy cave" in the basement to have a ciggie and a bowl of sweet medical pot.

Feeling better, lol, I went up to finish composing the salad and called Carol to the table. After seating her and serving her, I was able to join her in a scrumptious dinner. I told her about the company possibly changing the corporate smoking policy, and how we should probably look into another way to stop my smoking.

"Well Bren, I could just cane you 5 times for every ciggie you suck down, but you would probably smoke even more you sissy pain slut." she laughed. "Seriously though Bren, I have been giving it some thought. Why don't we try hypnosis. I know you tried it before and said it did nothing, but that was a group class with some huckster."

"Yes, I remember that it took 6 months to get our money back from that shyster."

"This time I want you to try a one on one appointment. I can show you a couple websites after dinner, if you like?"

"That sounds a lot more practical. But, also more expensive if it doesn't work."

"If it works it will be cheap, especially compared to what you spend on those pieces of crap you like to suck on!"

"Yes Miss Carol. We should give it a try," I agreed.

After cleaning up after dinner I joined Carol at her computer as she pulled up a website. It was the office of a local practitioner and was full of info about their stop smoking services. The office was owned by a husband and wife. They both did hypnosis for stopping smoking, and each had their own specialties as well. Things like weight loss and personal development were listed. Miss Carol skipped by those and we concentrated on the issue at hand.

She played an audio clip from each of them and they both had very soothing, but not pretentious sounding voices. "I could live with that I think Miss Carol. I mean I am certainly willing to give it my best effort."

We watched some television show and headed to bed. I lovingly brought my wife to 2 huge orgasms with my tongue. After 30 yrs of marriage, I never tired of her wonderful taste. To worship her beautiful cunt was like heaven for me still. I guess I am just a vagitarian at heart. When she signaled she had enough, she sent me to the bathroom to take care of my sissy clit before I went to bed.

Not often being allowed to squirt, I did just what she said, and oh my, was it sweet. I joined her in bed, shortly and kissed her before I fell asleep.

In the morning she handed me one of my tightest girdles to wear. The ones with the cut out cheeks that made my butt look really big, and a pair of tight stretch capri pants. Combined with my semi sheer cream colored blouse I looked like your typical office worker. Black 2" pumps and some makeup, a quick blow out of my hair and I was ready to go to work. Carol was in her nurses scrubs and out the door right behind me. With a kiss in the driveway we were off in opposite directions.

The day at work was going smoothly and I was glad I was leaving at 3 today. I was going to the salon to get my nails filled before going home. Carol called when I returned from lunch. She had called the hypnosis office and they said they could see me that afternoon at 3:30.

"But I wanted to get my nails done after work," I protested.

"This is much more important Bren. You don't deed fancy nails if you die from cancer. You will keep this appointment, understand?

"Yes Mistress Carol," I meekly replied. "Do you know which of them I am booked with?"

"No, but it doesn't matter. Just be there with an open and relaxed mind. Maybe smoke a bowl before you get there. I am sure you have some with you."

"Yes Mistress I will be there. Just text me the address please."

She hung up and sent me the address. Not to far away from my offices so at least I wouldn't have to rush. Being trans I was always a bit nervous meeting people for the first time. As I said before, I don't pass as well as a lot of girls but I don't worry about that too much. I am always beautiful on the inside as I see it.

I had a few tokes to relax me while in the parking lot before going up to the hypnotists office. The office itself was airy and modern, much like a dentist or corporate reception area. I nice looking woman sat behind the desk.

"Hi I'm Bren Roberts," I said approaching the lady at the desk. "My wife made an appointment for me to see someone about my smoking problem."

"Oh, um, I see. I thought she said. I mean, well yes she did. I'm sorry, please fill out these forms and I will let them know you are here," she said in a bit of shock.

Looking at her nameplate I tried to ease her mind. "It's ok Ms Ames. I am sure my wife said it was for her husband so I understand the confusion. And, yes I guess technically I still am that but we are more kind of wife and wife."

She smiled and went went back to her work. I finished the paperwork and she informed the Dr's that their 3:30 was here,

I few minutes later the team from the website came in. Sylvia and Mike Wentz introduced themselves and welcomed me to the office. We went back to their office and I sat in a comfy leather chair with them across from me.

"Normally we see patients one on one, Bren. But as your wife explained how deeply hooked on those ciggies as you are I think we will work together with you. Why don't you tell us a bit about your habit."

I explained how I felt a need to smoke after eating anything, even a few m&m's. I told them I was smoking more than a pack a day and would often read porn and wank while chain smoking if my wife wasn't home. I also mentioned that my doctor wouldn't authorize hormone treatments if I remained a smoker. Why did I tell them all that.

After a while Sylvia tapped me on the shoulder and said that was all for today. I looked at the clock on the wall and noticed an hour and 15 minutes had passed. All I remembered is that I started telling them about my habit and then we were done. Wow. I must have been hypnotized and not known it.

Mike gave me a handful of lollipops with instructions to try and avoid smoking as much as possible. If I wanted a smoke I should try sucking a lollipop instead. He said he felt they made good progress and tried to get to the root of my smoking habit. They wanted me back at 4pm the next Tuesday, and I made an appointment with Ms Ames before I left.

I headed home and started preparing dinner when Carol arrived home. Of course she asked about my appointment and I gave her all the details that I remembered. I told her about the lollipops and how I was supposed to suck on one when I wanted a smoke. After dinner we were relaxing in the living room when I wanted my usual after dinner smoke. Seeing me reach for my pack, Carol reminded me of the lollipops.

I agreed and grabbed one and unwrapped it. Unlike a standard lolli, these were a cream color and kind of cone shaped with the stick in the small end. Carol turned on Jeopardy as I sucked quietly, only taking it out to try and beat her to a question.

"These taste different from any lollipops I have had before. Sort of sweet but its like they are sticky in my mouth ant throat. It does seem to be calming my smoking urge though. I wonder where they get them?"

"That shape makes it look kinda sexy as you put it in and out, Bren. Perfect motion for a little sissy. Ha ha."

"Carol, if it helps me quit it would be worth it."

"You mean after all this time I only needed to find you something to suck on to make you quit that shit?"

"No, I'm not saying that. You know I am a vagitarian. Its just after the hypnosis session they probably did something so the lollis take my mind away from cigs, that's all."

I did well and had a couple more of them that evening. Carol was pleased with my not having smoked in the house that night and directed me between her legs for an extended oral session. Her juices flooded my face in a way that they hadn't in ages. When she was satiated she pulled me up alongside her and started stroking my sissy clit. She soon had me on edge, begging her to make me squirt. She said that I could if I agreed to a demand from her.

"To earn your orgasm sissy, you have to promise to confess to me every cigarette you smoke from now until you convince me you have quit. Will you do that for me sissy?"

This didn't seem so odd so I instantly agreed. Moments later while stroking my hard 8 inch clitty with one hand she ran a fingernail along the frenum, under the head, and I exploded all over my belly.

It took a while to come down and I asked her why she wanted a record of my smoking.

She reached onto my tummy and scooped up some cum and wiped it all over my face. "As for the smoking, I know you really want it to work this time. So I have ordered a new toy for you. It should be here in a few days. Its a lovely steel chastity."

"I really don't think we need to go there Miss Carol. I am going to make it this time. I promise."

"Then you won't have a problem. But if you have a smoke, it will cost you a day in chastity. As will a second cigarette. The 3rd will cost you 5 days and the 4th as well. A fifth ciggie will cost you 10 days. 6-9 will be fifteen days each and 10 or more will be 20 each." And any new number starts at the end of the previous one."

"Miss Carol, isn't that a bit severe? I could be locked for a month or more with that program!"

"Well you said you could make it this time and I have faith in you Bren. You be a good girl and you will have no issues. And with the money we save after a couple months of you being a non smoker, I will take you to Key West and parade you on the beach in a bikini. Now turn off the light and lets go to bed!"

"Yes of course Mistress."

I reached out and turned off the light. As I turned back Mistress snuggled close and licked at the cum drying on my face. "Mmm, too bad you never want to try your cummies darling sissy. It tastes so yummy," she whispered in my ear.

The next morning we showered together and soon headed out for work. I'm glad she reminded me to take my lollipops with me. She also said I should probably call Dr Wentz's' office and request more, as I only had a few left.

After making my usual coffee stop on the way in to work, I found myself stuck in traffic and lit a smoke in frustration. It tasted great, but I felt guilty inside. Work went well, and usual, although Sarah did ask me about my lollipops. I was glad she did because it reminded me to call for more. I filled her in on the hypnosis and how I was to supplicate myself with them instead of smoking.

I stopped by the Dr's office on the way home and got a bigger supply of the suckers. Again I arrived before Carol and started dinner after changing into a sexy little mini skirt and belly shirt. Just a chicken salad for dinner with a light wine and cheesy garlic bread.

Carol came in while I was cooking. She called to me that she was going to freshen up and change. Unbeknownst to me, she had also popped downstairs to the laundry room to grab some towels. She would have smelled the cigarette I had smoked when I got home. I should have gone outside, dammit!

When she came to the dinning room she told me to take the sucker out of my mouth and stand before her.

"Did I smell smoke in the basement room sissy," she demanded?

"Yes Mistress, I admit I did slip up when I got home and had one."

"Is that all you had?"

"No Mistress, I had one on the way to work. But it's not my fault. There was a traffic snarl up and I was frustrated and needed to calm down. And the lollipops were in the back seat."

"So you think that excuses you? And why were the suckers in the back seat?"

"They were in my purse Mistress. I usually put it in back with and work papers. I will keep them up front in the future. And I picked up more after work today. They gave me a whole box full."

"Good thing that chastity will be here tomorrow sissy. Now serve dinner and we will finish this discussion after we eat."

After dinner I was directed to go to my sissy room and prepare myself. I knew that to mean I should strip to my panties and await her on my knees, with the lined leather cuffs on my wrists and ankles.

"Yes Mistress," I sheepishly replied and headed downstairs. "Preparing myself" was almost a code for prepare to be punished.

I soon heard her footsteps approaching. I lowered my head as she entered, seeing only her black stilettos. She buckled a leather collar around my neck and clipped a wrist to each side. I then licked her boots as she presented each toe to me. When she was pleased with my efforts she had me stand and backed me up to a column in the middle of the room. The back of the collar was attached to a ring in it. My hands helpless at the collars sides.

My legs were spread and my ankles were then attached to eye hooks conspicuously placed under the false floor.

Gripping the sides of my face with one hand she stared deeply into my eyes. "Now that I have your undivided attention Bren let me explain something to you. That clitty between you legs belongs to me, as does your entire body and mind. I enjoy that clitty toy of yours. It is quite a bit bigger than most of the sissys in your porn sites you like to visit. It makes it fun to play with."

"But, my naughty little sissy, now I have to lock one of my toys away for 2 days after the cage shows up. That means I don't have a toy to play with, and that pisses me off! So if I am to be punished in that way, I am going to make it worthwhile. I am going to ask you to beg me to start your lock up at 20 days just to apologize for taking my clitty toy away. How's that sound to you?"

"Oh no, please Mistress that's so long a time Mistress. You certainly wouldn't want to go that long without it would you?"

"No I don't, but I will. And I will still be having daily pleasure." With that she grabbed a pair of clover style clamps attached by a chain and clamped them to my nipples. They were placed behind my piercings so they would get tighter, not fall off, when pulled.

She added a 4 ounce fishing weight to it and then another. As I didn't beg her, she added another. I didn't know we had 3 of them and winced deeply for the pain on my chest.

"Something you want to say, sissy"

"No Mistress."

She walked out of view, gathering something else to torment me, I was sure.

"I know you just hate the thought of a cock in your mouth sissy but I think this will fit nicely." She shoved the stubby cock gag in my mouth firmly fixing it in place behind my head. Pulling her clitty toy from my panty, she snapped a leather strap around it and gently stroked me until I was hard. "A much bigger target this way darling." And she stroked it some more.

Then I heard a whoosh sound and felt the tip of her crop slash across the head of my clit. I shook in my bonds, only to make the weight on my nipples swing and cause even more pain. 3 more strikes in quick succession followed. The gag blocked out most of the sound but not the pain.

Mistress stroked me gently while looking into my eyes. "My my sissy, you must be enjoying it as you are still very hard. Lets take it up a bit shall we. You don't seem willing to acquiesce to my desire just yet. She took the black satin scarf from around her neck and used it to blindfold me. I heard footsteps and then a drawer opening and closing.

Mistress was back next to me again. Stroking my clitty slowly. "Guess what I found in your desk the other day sissy? I didn't think these things were even around anymore. Lets see if they still have the same effect on you."

As she moved a hand towards my face, I could smell the poppers she had found. I found them at an adult book store recently and bought a couple bottles. She held a moistened cloth by my nose and with my mouth gagged I could only inhale the aroma. When she sensed I was flying high she grabbed me again and twisted so the more tender frenum was exposed.

The crop came down firmly and sent me deep into subspace with barely a whimper. Again and again it struck. Getting full coverage. As soon as I started to squirm she held the cloth up to my nose. Longer this time.

All I wanted was to be right where I was feeling her enjoy herself with me. I wanted to feel her power. I needed to be her pleasure toy. I wanted her to orgasm from her power over me.

I heard her voice in my ear. "Go deeper Bren. Give yourself to me. You don't want this clitty toy anyway. Beg me to lock you away my darling sissy. You won't even need a girdle to look smooth in the cage. I know you will love it."

She moved the cloth and added 20 more whacks of the crop on my clitty. I had tears on my cheeks but she decided they were tears of joy.

"Is there something you want to ask me Bren?"

I nodded my head yes.

She undid the gag and I tried to talk. With my stiff jaw and being all poppered I could barely make words.

"Mitress, pease mirtres. I um I.

She quickly shoved the gag back in. "Well if you aren't ready to talk yet maybe I should continue where I left off sissy. She put some lube on my sissy clit and stroked up and down over the welted skin. It was so sore but felt so dam good. Good until she wrapped a piece of sandpaper around my lubricated tool and slowly stroked up and down my length.