After I arrived in my workplace, nonetheless staring on the panties and stocking within the manila envelope, I acquired a textual content message. It mentioned, “Mike, we have to maintain issues on the down low within the workplace. Friday was wonderful however I wish to maintain it between us for now. So, I’m going to be an actual laborious ass to you all week. I do not need anybody catching on. What we’ve is particular and I do not need them to spoil it. In the event you go alongside and are available over on Friday, I promise it can all be price it.”
Final Friday Tammy took me to locations I had by no means been. When she put me in French panties, thigh-high stockings, tied me up, and rode my dick I used to be in heaven. I even preferred it when she referred to as me sissy. So, after that, I used to be keen to go together with what she mentioned. Though simply occupied with her tight, juicy pussy already had me laborious. It was 8:49 am on Monday and I wanted to settle down earlier than a gathering.
The remainder of the week was powerful. Tammy was brutal. She criticized all the things I did at work. Sure, she was the workplace supervisor, and I did not report back to her, however she went out of her solution to spotlight how messy my workplace was, how I did not label issues within the firm fridge, and at one assembly she challenged my work. I needed to surprise if she was a superb actor, or if she actually hated me.
On Friday, at 4:45 p.m., I acquired one other textual content message from Tammy saying, “Come to my home at 7:30 tonight. The door can be open. Simply enter. Do not flip the lights on. I am going to discover you. You’ve got been a superb Sissy boy all weekend and I’m going to make it as much as you. Please put on a go well with in addition to your panties and stockings. Friday could also be informal at work however the considered you in your pinstripe go well with sporting panties and stockings makes me moist.”
At 7:30 I opened the door and walked in. I treaded frivolously simply feeling my means round. I assumed I noticed candlelight on within the subsequent room, so I moved towards it. Then two palms lined my eyes. I jumped.
“Maintain nonetheless. I’ve you and I’m not letting go,” Tammy whispered into my ear as she pulled me nearer. Her left leg snaked round mine and her hips grinded into me. My coronary heart was pounding.
“Okay…” I mentioned nervously.
“You had been good sissy boy all week. I do know there have been instances I used to be laborious on you, and also you took it. Took it like a person,” she mentioned placing heavy emphasis on the phrase man and a tough grind into me. Then she bit my ear lobe.
“Did you do what I requested immediately? I can really feel your go well with coat and pants, so you might be midway there. Drop your pants and let me really feel the remaining Sissy boy.”
“Okay, Tammy,” I mentioned 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.
“Superb Sissy boy,” she whispered into my ear. “Mistress goes reward you all evening. However first, some issues are going to vary.”
“What Tammy?”
“That’s the first. Within the exterior world, I’m Tammy, and you might be Mike. However right here and in your house, I’m Mistress, and you might be my Sissy boy or Sis. Are we clear?”
“I do not like being referred to as Sissy Boy.”
“What?”
“It jogs my memory of all of the teasing I acquired as a child.”
“This is not about these assholes. It is about you and proudly owning who you might be and never caring. Once I referred to as you Sissy boy final week you got here tougher than any man I’ve ever been with. Do not you want feeling like that? Did not you want the texture of the panties and stockings?”
“Sure… but it surely’s laborious for me.” I stammered. “All my life I’ve been referred to as that as an insult. It brings up too many unhealthy reminiscences. I’m… am… a really repressed particular person with intercourse.”
“What? I did not know you felt that means however the truth that you might be right here tells me there’s a slutty Sissy in there that actually needs to come back out extra usually. He actually got here out final week.”
I blushed.
“Thanks.”
“What if we gave Sissy new reminiscences?”
“What?”
“What if each time you had been referred to as it now it was about freedom and pleasure? It was about you having a good looking Mistress fuck your scorching physique whereas these assholes sat there along with your beer bellies and bitchy wives. You, the Sissy boy could be the one getting the pleasure solely an actual man can take pleasure in,” she mentioned as she rubbed my physique.
“Sure,” I mentioned as I smiled.
“The one means to do this is to let that aspect of your self out. That may be a fuck you to all of the jock assholes who instructed you find out how to be a person when the true you was so a lot better.”
I by no means heard anybody say that earlier than. I may really feel her pleasure as she mentioned it. Nobody had ever made me be ok with being the way in which I’m.
“Okay, in right here I’m your Sissy boy. However solely with you.”
“Superb however you forgot one thing,” she mentioned changing into sterner.
“Oh. However solely with you Mistress.”
“Now, that is a lot better Sissy boy.”
She spun me round and took my jacket and shirt. Then she bent down, untied my footwear, and took them and my socks off. I used to be standing there with solely a blindfold, French-cut panties, and thigh-high stockings on.
Tammy grabbed my hand and led me into one other 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 ft all day. Sissy boy, please rub and worship my proper foot.”
“Worship?”
“Sure, present Mistress how you’re feeling about her foot and make her foot really feel good.”
I seemed up and smiled. I grabbed her foot and started to maneuver my proper thumb in a clockwise movement proper the place the arch met the large toe. I then kissed her foot proper above her toes. She dug her nails into my head and pushed me down. I then kissed and licked the highest of her toes. They had been just a little sweaty. I saved massaging with my proper thumb after which dug my left thumb into the bottom of her foot. I did this for a couple of minutes. She let loose an oohh that made me grin. I then sucked on her huge toe.
“Oh, Sissy.”
I saved rubbing however moved as much as kiss and lick her ankles. As I did, I made eye contact along with her. She pushed my head down.
“Keep on the foot Sissy.”
“Sure, Mistress,” I mentioned as I may see she had began fingering herself.
I continued for a couple of minutes. I moved all the way down to squeeze her heel with my left hand. All of the whereas rubbing the identical spot with my proper thumb.
“You’re such a superb Sissy boy. Come right here to your prize.”
I stood up and she or he backed away. She saved motioning for me to come back ahead as she backed me into the bed room that was additionally lit by candles. On the foot of the mattress, Tammy pulled me into her and kissed me. Her tongue went proper into my mouth and her fingers went proper by way of my hair. I acquired goosebumps. I wrapped my arms round her. Then she moved her proper hand all the way down to my ass. She caught her pointer finger in, and I jumped. I used to be shocked and thrilled. My dick nearly exploded.
“Now Sissy goes to get his prize. Is he prepared?”
“Sure, Mistress.”
Tammy walked away and went to her nightstand. She pulled out a gift-wrapped field.
“Here is your current.”
I unwrapped it and opened the field. It was a plastic set of beads. Every bead was greater than the following, with a circle on the finish.
“What is that this?”
“It should make my Sissy very glad,” she mentioned. Then she pulled out a container of lube. Then she squirted some on the beads and handed it to me.
“What do I do?”
“Unfold your cheeks and lube up. It will make insertion higher. Belief me. We’re going to go gradual. Tonight, we’ll do one or two beads and transfer them out and in.”
I used to be scared however I trusted her. After I rubbed my ass with lube, she slowly pushed it out and in.
“Now you do it.”
I did it and felt pure exhilaration. It was like being on a rollercoaster. She lit one other candle whereas I did it.
“Feels good Sissy?”
“Sure, Mistress…” I mentioned out of breath.
“Depart it in,” she mentioned and pulled me shut.
We kissed passionately and fell onto the mattress. I used to be on high, however she was dictating the tempo.
“Now begin shifting the beads out and in,” she mentioned. “Slowly at first. I’m in management.”
Then she put a condom on me after which moved my dick into her moist pussy.
I trusted her and did it. Our tempo ticked up. We moved ahead and again in rhythm. I saved shifting the beads. I used to be so laborious, and she or he was so tight. She dug her nails into my shoulder.
“You prefer it, do not you Sissy? You fuck!! You soiled little fuck!! Oh!!” she moaned.
“I’m about to,” I mentioned struggling to get the phrases out.
“Pull it out as you come!”
I did. My eyes rolled again in my head. I used to be in heaven. I collapsed in her sweaty arms. As I lay on high of her each of our hearts pounded.
“Good Sissy boy!!”
I held her and let myself fall into her. She was my Mistress.
“Did you?”
“Do not ever ask that once more Sissy. However sure, when you had been worshipping my proper foot, I fingered myself to an orgasm. Tomorrow, I’ll allow you to lick my clit.”
“Sure, Mistress.”
“Quickly, Mistress will give her Sissy his first pegging.”
“What’s that Mistress?”
“Don’t be concerned Sissy. Mistress will let you understand. And I do know Sissy will take pleasure in it. Belief me.”
With that, I drifted off to sleep as one very glad Sissy.