The Association of Sissies Ch. 02

It had been a busy morning. I started at the doctor's office for a checkup on my hormone therapy. I then completed the foreclosure on a farm outside of Santee. I had a bloodied nose and black eye after being assaulted by the former owner. Luckily the Sheriff was onsite for the eviction notice and witnessed everything. I didn't press charges mainly because I would have had to show my ID to the Sheriff. My name has been legal changed and my picture is current, but the ID still says "Male."

"I've known Bill for forty years. You are the first person that he has ever even said a mean word to. And to hit a woman, I can't believe it. I don't know what you city folks got into with him and his finances, but it still ain't right what he done did there, ma'am." The Sheriff said to me.

"Thank you Sheriff. We actually purchased and consolidated all of his debt. We gave him an easy payment structure. He would have ended up paying less in interest with us than his other loans. We gave him several opportunities to catch up on missed payments, but we eventually we had to foreclose."

"Well, sounds like you tried to do the right thing. You sure you don't want to press charges?"

"Yes sir. I'm sure."

"Ay'ight then young lady. Have a safe trip back to Charleston. Get some frozen peas from the Food Lion over yonder on Bass Drive and keep the bag pressed to your eye."

I didn't lie to the Sheriff. He would have saved money with us had he paid on time. We would have made a little easy money, but not really enough money to have that much cash locked into the deal. He was in debt and had no access to any other loans. He was losing everything. We got to him before he went into bankruptcy and purchased his debt. We did this by giving him a very low interest rate and adding a ten thousand dollar cash loan to the debt. His property would be collateral. We waited for him to go overdue. Gave him a few extra chances, and then held an auction for the property. We followed the law and held the auction on the grounds of the courthouse, but the law doesn't specify where the auction has to be held on the courthouse grounds. We usually use the Men's or Women's bathroom, depending on the gender of the lawyer performing the auction. No bids, which is what we wanted. We essentially purchased a couple million dollar farm for a little over three-hundred-thousand.

The farmer got ten thousand dollars in cash that he never would have gotten had he foreclosed with the bank or gone through bankruptcy. Are we predators? Yes. Was the prey going to die anyways? Yes.

It felt nice to be back at the office. I set my bag and files on my desk. Jim had me setup in the reception area which worked out fine since it was just the two of us. I knew he would want to hear how everything went so I straightened myself and knocked on his door.

"Come in, Janice."

I walked to his desk and stood by his side patiently. He worked on his computer. He had been working on his "Manifesto" ever since I met him. It was pretty incredible. He had read me parts of it. I'm not sure if the scientific community would be ready for such a huge shift in the understanding of the human psyche, but it could potentially change the world.

Jim looked at me after maybe ten minutes and said, "Turn around and bend over."

I faced away from him and bent over. He flipped my skirt up. I could feel his calloused hands on my cheeks. I trembled slightly.

"I see that all the marks are gone from your last lesson. You get regular maintenance spankings, I don't know why you insist on having to learn these painful lessons on top of those."

"The only thing I want to do is make your life better, Daddy. I'm sorry that I keep you from more important things." I said, very sincerely.

"It's a labor of love, misplaced on my part, maybe, but still love. It's fine as long as you keep improving. I know you want to do better."

Daddy moved the string of my panties over and spread my cheeks. He always checked to make sure that I was wearing my plug, like a good girl.

"Turn back around, Janice."

Daddy rolled his desk chair out from under his desk and angled it so he looked straight at me. He then leaned back and looked up at me.

"Holy shit! What in the hell happened to your face?"

"Bill attacked me while the eviction notice was posted. The Sheriff was right there and stopped it. He did it in front of his wife and kids too."

"Are you okay?" He asked with genuine concern.

"Just a little sore, not a big deal."

"Well... how did the rest of the day go?" He asked with a laugh.

"The lawyer held the auction in the Men's Room. He had one witness and no bids. I notarized the transaction."

"That's great, and the eviction notice was obviously posted."

"Yes. Yes it was." I said with a smile.

"How did your Doctor appointment go, sweetie?"

"It went really good. Really well, I mean, Daddy. My blood work came back great. He said that my body has adapted and transitioned over the last year better than he could have hoped for. He said all my tests were negative. I put copies in my file for you to look at."

I was forbidden from playing with others. It didn't matter because I wasn't interested. I would never betray his trust again. He still has to be cautious. I get screened for STDs regularly. His work is too important for the future of our society. He can't take risks.

"Did the Doctor have any concerns?"

"He wants me to put on weight. Even just five pounds. He says it would more than likely just go to my breasts, at the rate they are growing."

"Let me think about that. Your breasts are plenty big as they are. I quite enjoy them as they are. What if it goes to your waist? It would take forever for you to lose that weight. What would I do in the meantime while you looked disgusting? We already brought you up to one-o'five. Is one-ten that necessary? I just am not sure that I want to risk it."

"Okay. I was pretty sure you wouldn't be interested, but I promised the Doctor that I would bring it up."

"Well hey, I have a lot of work to catch up on. I want you to take the rest of today and tomorrow off. A nice four day weekend. Keep ice on your eye. I will be home soon."

"Yes sir. Thank you so much!"

I was halfway to the door when he stopped me.

"Oh hey! Come here real quick."

I quickly came back.

He motioned to his crotch and said "Before you leave, may as well get this one out of the way."

"Yes sir, good idea." I said as I got on my knees.

I helped him remove his shoes, pants, and underwear. His cock laid on his thigh. He spread his legs and I crawled between them. I immediately planted kisses all over his penis. I lifted his penis up and kissed down the shaft to the base. I kissed bis balls and started to lick them. He lifted his legs and held them back so his balls and ass were arched towards my face. I licked on his balls and sucked on them, one at a time. I then licked down his taint to his ass and gently probed it with my tongue. He moaned as lapped at his asshole. I grabbed his mostly hard cock and gently stroked it while I plunged my tongue in his exit.

He moaned and lowered his legs. I slowly moved up the shaft with my tongue. Soon Daddy was were he belonged, inside my mouth. I worked on what I could fit in my mouth. I licked and sucked. I stroked and licked some more. He reached over and grabbed a camera off his desk.

He was an award winning photographer. I was incredibly lucky to be his muse. He aimed and shot pictures. He had a diffuser around the flash, which I liked because it didn't blind me. I looked straight at the lens as I sucked and licked in very slow movements. Stopping to pose in sensual and suggestive poses with his beautiful penis.

He put the camera back down and grabbed my head. He pushed down hard so every inch was inside my throat. Daddy held my head tightly and stood up. He started to pump his cock in and out of my throat. I couldn't do anything but take what Daddy gave me.

Daddy pumped as I choked and gasped. He would wait and then pull out just enough for me to breath. I could taste the sweetness of his precum. I could feel the excitement in his movements. I knew I had pleased him well. I could tell from his breathing that he was close. I got ready to swallow. He moaned loud and pulled out so only his head was in my mouth. I stroked his shaft while his cock spasmed and flooded my mouth. I sealed my lips tightly against his cock so no cum was wasted. I swallowed every drop.

"That was good. Thank you. Would you like to cum?" He asked me.

Embarrassed but thankful, I nodded yes. He reached into his drawer and pulled out a condom and a bullet vibrator. I rolled the condom on my rock hard clit and pressed the vibe up to it. I placed Daddy's cock back in my mouth and turned on the vibe. I wasn't allowed to masturbate or cum without him being inside of me. Daddy would sometimes let me masturbate after he came, as long as his cock was still hard and inside of me. I was already pretty hot and heavy. It didn't take long for my little balls to empty out into the condom.

I tied a knot on the end of the condom and threw it away. I then helped Daddy get dressed again.

"Thank you Daddy." I said.

"You're welcome, now go home and rest. You're going to be busy again tonight, I'm going to try to get you pregnant again!"

I laughed.

We laid in his bed together. It was a lazy Saturday evening. We watched Seinfeld. I had eaten my normal meal of broccoli and grilled chicken. Daddy let me cheat with a slice of the pizza that he had ordered. It had green olives, feta, and spicy salami.

Daddy rubbed my shoulders and kissed the back of my neck. I was in pure sissy heaven. He gave me a massage earlier. Afterwards he filled me to the brim with his cum and then quickly sealed me with my plug.

The condom on my clit was loose. It was filled with all the cum that he had pushed out of me. Daddy was tired of having to wait for me to change the sheets after he fucked me. I always left a huge puddle and made a mess. It wasn't fair to him because he was never able to relax after he fucked me.

"I've been putting together a curriculum based off of my Manuscrit du Manifesto. My lawyer is preparing the paperwork for my new business, the T.U.M.S. Institute of Technologies."

"That sounds amazing. I'm so proud of you." I said.

"You actually inspired me last Wednesday. Seeing you hurt, I knew I couldn't continue to risk your safety. Real Estate transactions can be dangerous. Seriously, in remote areas alone with strange men. It isn't safe."

"You don't have to do it because of me."

"I'm not, you just inspired me to get the work done. Now I need you to work on something other than Real Estate. You inspired me, and it worked out."

"You will be an amazing teacher." I said.

"No. You're going to be the face of the training. I'm going to be in the Breakout Sessions. You will be presenting the core principles of the curriculum."

"Do you think I can?"

"I know you can. You've been learning my philosophy over the past year. It will be easy for you to teach once we organize it in lessons. You will see."

"Do you think the audience will listen to someone like me, though?"

"You have never once been outed in public, and you even got into a fist fight once. Nobody will suspect anything. You are prettier and more feminine than most biologically female women anyways."

We were in a holding pattern on most of our deals. Jim focused on the curriculum. His goal was to create multiple course sections and different levels of each section. Return business would be crucial for the business.

I took crash courses in video editing at the community college. Our sole focus was developing these seminars. We slept only a few hours a night. We didn't even have time for our normal routines, which inadvertently made Jim more aggravated. We advertised heavily. We rehearsed constantly. He even began to trust my work.

Our first seminar was only a few days away. We were ready, surprisingly. I kneeled on the shower floor and washed Daddy's penis. I worked down to his feet and back up to his waist. I rinsed him off and quickly washed myself off while he relaxed.

I got the towel and dried Daddy off. I then quickly dried myself off and put on a fresh pair of panties. I helped him put on pajamas and kneeled by his bed like a good girl.

"We can't keep up with this. My job is busy. Your job is busy. You can't even take care of your main obligations, which are my needs. We need some help." Daddy said to me.

"I can try harder. I've been getting better which lets me get more work done. I can make sure to take care of your needs first."

"No. No. No. We need to keep our eyes open for candidates that we may want to hire at these seminars. We will be training them to think like us anyways."

"That's a great idea! What would you have them doing?"

"Helping out with your load. I would bring her through the same work training and of course the same obedience training that you went through."

"Obedience training..."

"She would be like your sister, your best friend, and your coworker.

"You would have sex with her?"

"Of course I would. Sometimes with you, sometimes with her, sometimes with both of you, sometimes with other people."

I knew that it shouldn't matter to me if he has sex with other people, but I couldn't help that it still broke my heart. My nose started to itch and my left eye trembled. I knew I wouldn't be able to hold back the tears for long.

"Would she be a girl like me, or one with a vagina?" I asked.

"Doesn't matter. Both have an ass and a mouth, which is all I use. I can see that you would be jealous of a sister that was biologically female, but a sister that is like you will always be jealous since you were born a perfect sissy."

"Do they have to be intimate with you? Can't they just be an employee?"

"How can I trust them without the obedience and the intimacy? You have to think of the big picture. We need to get this material into the world and I cannot second guess the people that I am trusting to help me do that. Obedience and intimacy are vital."

"I'm sorry, Daddy. You are right."

"We can't even go a week, sometimes. Go get the strap. We need to work on this right now before any bad behaviors set." He said as he shook his head.

I carried the strap to him. It had my name etched on the wood handle. The strap was actually two small straps. Each was about an inch and half wide by fourteen inches long. It hurt like hell, but it was less likely to permanently scar me. It was also quiet enough to use in hotel rooms when traveling.

Daddy walked me to the front of the bed. He yanked my panties down and took the strap from me.

"Get in position. This is going to be quick. No counting. We will be finished once I feel you learned the lesson."

I bent over and grabbed ankles. Daddy used to have to bind my ankles and wrists together and use a spreader bar on my legs. I could now stay in position on my own during punishment.

*CRACK* *CRACK*

*CRACK* *CRACK*

*CRACK* *CRACK*

*CRACK* *CRACK*

*CRACK* *CRACK*

*CRACK* *CRACK*

He would first strike with a forehand and then bring it back as a backhand strike in very quick procession.

*CRACK* *CRACK*

*CRACK* *CRACK*

*CRACK* *CRACK*

*CRACK* *CRACK*

*CRACK* *CRACK*

*CRACK* *CRACK*

Daddy gave a pause and asked, "Am I under your control?"

"No sir." I said between sobs. I was unable to hold back the tears anymore.

*CRACK!!*

He hit me hard, very hard, and asked, "Then why do you think you can control who I have intimacy with?"

"I'M SORRY SIR! I DIDN'T THINK ABOUT IT! I WAS JEALOUS!" I screamed while crying.

"JEALOUS?" Daddy asked in a yell.

*CRACK!!* *CRACK!!*

*CRACK!!* *CRACK!!*

*CRACK!!* *CRACK!!*

*CRACK!!* *CRACK!!*

*CRACK!!* *CRACK!!*

*CRACK!!* *CRACK!!*

*CRACK!!* *CRACK!!*

*CRACK!!* *CRACK!!*

I cried uncontrollably.

"You should never feel jealous towards me. You should love me. You should idolize me. You should appreciate me. You should feel deep shame when you misbehave and hurt me. You should never feel jealousy, anger, or hurt towards me."

"I'm sorry sir. I'm so sorry." I sobbed.

"I expect a full page, every week, on the proper emotions that you should feel towards me. I want you to address how this jealousy has undone all of your recent progress and also the troubles that has created for me. This is on top of the other two letters you write me a week."

"Yes sir." I said as I dry sobbed.

"Stay in position."

I felt daddy pull out my plug. He grabbed my face and stuck the plug in my mouth. He walked behind me. I heard him spit several times. I then felt his large cock push past my cheeks and press on my entry. His hands gripped my waist. He pierced my open hole and entered quickly with one hard push from the hips. I held on to my ankles tight, but slid forward as he entered.

"Position!" Daddy ordered.

He pounded my sore bottom. His groin slapped loudly on my cheeks. I could tell he was very excited. He fucked me much harder than normal and his cock somehow even seemed to be harder than normal.

"Fuck yeah." Daddy grunted.

My clit flapped around as he pounded me. I could feel him rub the spot that usually makes me drip. I realized that I had not put on a condom and panicked.

"Yeah. Take that fucking dick up your fucking ass." He said.

I wasn't nearly as slippery as I usually was, but my plug had retained enough lubricant there that it didn't hurt. His balls swung like a wrecking ball into my taint. He usually had sex with me. Tonight he used me.

I thought he might get tired of me after all this. I thought about how much trust he had just lost in me as I stayed as still as possible. Overcome, I sobbed again. Daddy started to pound me even harder.

"How do you like that, bitch?" Daddy grunted as I sobbed more.

I tried to think of other things but soon I felt him go much faster with shorter strokes. He breathed heavy. He gripped me tight. His cock spasmed inside of me which sent me over the edge. His strokes pumped stream after stream from soft clit on to the floor of his bedroom while he emptied himself into my sore and broken ass.

He sighed and slowly pulled himself out of me. He removed the plug from my mouth and pushed it into my ass. He then looked down at the floor.

"See what happens when you misbehave? Get on your hands and knees and clean the floor with your tongue."

I dropped to the floor and licked all of my cum off of the floor. Daddy grabbed my panties and grabbed me by my hair. He led me on my hands and knees to my bedroom. He sat down on the bed and pulled me across his lap.

Daddy pulled the plug out and put some more lube on it. He carefully placed it back in. He then calmly rubbed my bottom. He warmed up some lotion in his hands and rubbed it in.

"I don't know how much longer I can let you put me through this, Janice. I love you so much, but struggle with the ways that you challenge me. I want you to write your letter tomorrow. Make the first one two pages long. I need you to be empathetic to my needs and my position. I need you to understand that these decisions are bigger than just you and me. We, you and I, we... We need help to survive. We need help, but not from strangers. Not from people we like. Not even from people like us. We need help from people that are a part of us. A part of we. Those are the only people we can trust with something so important."

"I understand, sir." I said quietly.

"Janice, how can more love be a bad thing?"

I was humiliated. I had hurt, no. I had wounded him so deeply with my stupid pride and greed.

My alarm went off the next morning at a quarter til seven. I quietly slipped into Daddy's room and patiently waited until seven. I got on my side with my ass pointed towards Daddy. Morning wood had his pajamas and sheets straining hard. I slipped my head and shoulders under the sheets and gently pulled his cock out of his pajamas. I laid the side of my head on his belly and I started gently sucking while he quietly snored.