Tammy Takes Control

After I arrived in my office, still staring at the panties and stocking in the manila envelope, I got a text message. It said, "Mike, we need to keep things on the down low in the office. Friday was amazing but I want to keep it between us for now. So, I am going to be a real hard ass to you all week. I don't want anyone catching on. What we have is special and I don't want them to ruin it. If you go along and come over on Friday, I promise it will all be worth it."

Last Friday Tammy took me to places I had never been. When she put me in French panties, thigh-high stockings, tied me up, and rode my dick I was in heaven. I even liked it when she called me sissy. So, after that, I was willing to go along with what she said. Although just thinking about her tight, juicy pussy already had me hard. It was 8:49 am on Monday and I needed to calm down before a meeting.

The rest of the week was tough. Tammy was brutal. She criticized everything I did at work. Yes, she was the office manager, and I didn't report to her, but she went out of her way to highlight how messy my office was, how I didn't label things in the company fridge, and at one meeting she challenged my work. I had to wonder if she was a good actor, or if she really hated me.

On Friday, at 4:45 p.m., I got another text message from Tammy saying, "Come to my house at 7:30 tonight. The door will be open. Just enter. Don't turn the lights on. I'll find you. You've been a good Sissy boy all weekend and I am going to make it up to you. Please wear a suit as well as your panties and stockings. Friday may be casual at work but the thought of you in your pinstripe suit wearing panties and stockings makes me wet."

At 7:30 I opened the door and walked in. I treaded lightly just feeling my way around. I thought I saw candlelight on in the next room, so I moved toward it. Then two hands covered my eyes. I jumped.

"Hold still. I have you and I am not letting go," Tammy whispered into my ear as she pulled me closer. Her left leg snaked around mine and her hips grinded into me. My heart was pounding.

"Ok..." I said nervously.

"You were good sissy boy all week. I know there were times I was hard on you, and you took it. Took it like a man," she said putting heavy emphasis on the word man and a hard grind into me. Then she bit my ear lobe.

"Did you do what I asked today? I can feel your suit coat and pants, so you are halfway there. Drop your pants and let me feel the rest Sissy boy."

"Ok, Tammy," I said as unbuckled my belt, unbuttoned and my pants.

She moved one hand down and felt my French-cut panties and thigh-high stockings. Then she put a blindfold over my eyes.

"Very good Sissy boy," she whispered into my ear. "Mistress is going reward you all night. But first, some things are going to change."

"What Tammy?"

"That is the first. In the outside world, I am Tammy, and you are Mike. But here and in your apartment, I am Mistress, and you are my Sissy boy or Sis. Are we clear?"

"I don't like being called Sissy Boy."

"What?"

"It reminds me of all the teasing I got as a kid."

"This isn't about those assholes. It's about you and owning who you are and not caring. When I called you Sissy boy last week you came harder than any man I have ever been with. Don't you like feeling like that? Didn't you like the feel of the panties and stockings?"

"Yes... but it's hard for me." I stammered. "All my life I have been called that as an insult. It brings up too many bad memories. I am... am... a very repressed person with sex."

"What? I didn't know you felt that way but the fact that you are here tells me there is a slutty Sissy in there that really wants to come out more often. He certainly came out last week."

I blushed.

"Thanks."

"What if we gave Sissy new memories?"

"What?"

"What if every time you were called it now it was about freedom and pleasure? It was about you having a beautiful Mistress fuck your hot body while those assholes sat there with your beer bellies and bitchy wives. You, the Sissy boy would be the one getting the pleasure only a real man can enjoy," she said as she rubbed my body.

"Yes," I said as I smiled.

"The only way to do that is to let that side of yourself out. That is a fuck you to all the jock assholes who told you how to be a man when the real you was so much better."

I never heard anyone say that before. I could feel her joy as she said it. No one had ever made me feel good about being the way I am.

"Ok, in here I am your Sissy boy. But only with you."

"Very good but you forgot something," she said becoming sterner.

"Oh. But only with you Mistress."

"Now, that's much better Sissy boy."

She spun me around and took my jacket and shirt. Then she bent down, untied my shoes, and took them and my socks off. I was standing there with only a blindfold, French-cut panties, and thigh-high stockings on.

Tammy grabbed my hand and led me into another room. She sat me down. Then she took off my blindfold. The room was lit by candles. She stood over me and put her foot on my left knee.

"Mistress has been on her feet all day. Sissy boy, please rub and worship my right foot."

"Worship?"

"Yes, show Mistress how you feel about her foot and make her foot feel good."

I looked up and smiled. I grabbed her foot and began to move my right thumb in a clockwise motion right where the arch met the big toe. I then kissed her foot right above her toes. She dug her nails into my head and pushed me down. I then kissed and licked the top of her toes. They were a little sweaty. I kept massaging with my right thumb and then dug my left thumb into the base of her foot. I did this for a few minutes. She let out an oohh that made me grin. I then sucked on her big toe.

"Oh, Sissy."

I kept rubbing but moved up to kiss and lick her ankles. As I did, I made eye contact with her. She pushed my head down.

"Stay on the foot Sissy."

"Yes, Mistress," I said as I could see she had started fingering herself.

I continued for a few minutes. I moved down to squeeze her heel with my left hand. All the while rubbing the same spot with my right thumb.

"You are such a good Sissy boy. Come here for your prize."

I stood up and she backed away. She kept motioning for me to come forward as she backed me into the bedroom that was also lit by candles. At the foot of the bed, Tammy pulled me into her and kissed me. Her tongue went right into my mouth and her fingers went right through my hair. I got goosebumps. I wrapped my arms around her. Then she moved her right hand down to my ass. She stuck her pointer finger in, and I jumped. I was shocked and thrilled. My dick almost exploded.

"Now Sissy is going to get his prize. Is he ready?"

"Yes, Mistress."

Tammy walked away and went to her nightstand. She pulled out a gift-wrapped box.

"Here's your present."

I unwrapped it and opened the box. It was a plastic set of beads. Each bead was bigger than the next, with a circle at the end.

"What is this?"

"It's going to make my Sissy very happy," she said. Then she pulled out a container of lube. Then she squirted some on the beads and handed it to me.

"What do I do?"

"Spread your cheeks and lube up. It'll make insertion better. Trust me. We are going to go slow. Tonight, we will do one or two beads and move them in and out."

I was scared but I trusted her. After I rubbed my ass with lube, she slowly pushed it in and out.

"Now you do it."

I did it and felt pure exhilaration. It was like being on a rollercoaster. She lit another candle while I did it.

"Feels good Sissy?"

"Yes, Mistress..." I said out of breath.

"Leave it in," she said and pulled me close.

We kissed passionately and fell onto the bed. I was on top, but she was dictating the pace.

"Now start moving the beads in and out," she said. "Slowly at first. I am in control."

Then she put a condom on me and then moved my dick into her wet pussy.

I trusted her and did it. Our pace ticked up. We moved forward and back in rhythm. I kept moving the beads. I was so hard, and she was so tight. She dug her nails into my shoulder.

"You like it, don't you Sissy? You fuck!! You dirty little fuck!! Oh!!" she moaned.

"I am about to," I said struggling to get the words out.

"Pull it out as you come!"

I did. My eyes rolled back in my head. I was in heaven. I collapsed in her sweaty arms. As I lay on top of her both of our hearts pounded.

"Good Sissy boy!!"

I held her and let myself fall into her. She was my Mistress.

"Did you?"

"Don't ever ask that again Sissy. But yes, while you were worshipping my right foot, I fingered myself to an orgasm. Tomorrow, I will let you lick my clit."

"Yes, Mistress."

"Soon, Mistress will give her Sissy his first pegging."

"What's that Mistress?"

"Don't worry Sissy. Mistress will let you know. And I know Sissy will enjoy it. Trust me."

With that, I drifted off to sleep as one very happy Sissy.