Sissy For My Flatmate, Chapter 2 – The Contr
If you've only just tuned in, here's what's going on in my life. Until recently I was a closet crossdresser trying to keep my hobby from my flatmate. When he caught me in the act, I found out that not only had he known about me for a long time but it was a turn on for him. I agreed to become his sissy slave and started the most incredible journey of my life.
Arriving home after from work, I threw my jacket down on the sofa and breathed a sigh of relief. It was Friday and I now had the weekend to look forward to. I slowly unbuttoned my short to reveal a short corset. It's been a few weeks since I accepted Bens offer to become my master. Since then we hadn't worked out anything formal, while we were both getting used to this, but Master told me I should be kept corsetted. The corset I'm wearing is a mens corset, we agreed it would make me look a little less ridiculous at work and it had a smoother outline under my shirt. The first few times I wore it to the office – I was so scared of it being noticed! Once I'd gotten used to it and knew that nobody knew – it was my fun little secret. I often wondered how many of my colleagues had something similar on under their vanilla work attire.
After I untied the bow and slacked off the laces, I took in a big lungful of air. While it's comfortable and I absolutely love wearing it, a full lungful of air is something easily taken for granted. After hanging the corset over the chair in my room, I stripped naked. In a break from the norm, I hadn't been instructed on what to wear so I surveyed my wardrobe for something that would please Master. As I had basically gotten used to wearing a corset all the time, I took this as a starting point. I picked out a pair of stockings, panties, underbust corset (this time all in white) and grabbed a pair of 6 inch white stilettos. I studied my collection of wigs, thinking about my look for tonight. This time I will be a long haired redhead. After getting changed, I stepped in to the bathroom to apply my make up.
I'd seen pictures of crossdressers caked in makeup, an overapplication of eye shadow that made them look more like pandas! I can look trashy when I want to – this wasn't one of those times. Master wasn't going to presented with a slut, I was going to appear elegant for him. I applied foundation, a little eye shadow, a light coloured lipstick (nothing outrageous), a little eye shadow and some mascara. A pair of clip on earings completed my outfit.
Noticing the time (he should be home shortly), I made my way in to the living room and took up my position on my knees to wait for him. The thought of seeing Master again was making me horny as Hell. The fact that I'd been wearing the chastity belt for 2 weeks only added to my excitement.
I waited patiently for ten minutes, my heart raced when I heard the door unlock. Sure enough, Master stopped at the entrance to the living room and studied my appearance.
“Welcome home, Master!” I said in my best falsetto voice.
“I've had a terrible day, Cindy”
“Would a blow job make you feel better, Master?” I figured a quick BJ might cheer him up. If not, it would at least take his mind off things.
“That sounds like a great idea” He replied, sitting down on the sofa and unbuttoning his trousers.
Instead of standing, I crawled over on all fours to where he was sitting. By now he had his cock out and it was already erect.
As always, I had to ask permission. I looked in to his eyes “Master, may I please suck your cock?”
I waited for his nod and used my hands to hod his cock as I kissed the tip of it, all the while looking in to his eyes. I took the length of his hard cock in to my mouth and caressed it with my tongue. I let out little groans as I explored every detail of the cock in my mouth and worshiped it. By now, I'd started getting better at deep throating. I took his cock further in to my mouth, letting out a little gag as it hit the back of my throat. I continued until my lips were at the base of his cock. Ben wasn't used to being deep throated, I knew this would bring him right to the point of cumming. Sure enough, I felt it throbbing – he was close. I pulled back and as he let out the sounds that could only be produced by a mind blowing orgasm, I felt his now throbbing cock fill my mouth with cum.
I drew it all on to my tongue, poked it out of my mouth and stared in to his eyes, waiting for permission to swallow.
I pulled my tongue back in, swallowed his load and stuck my tongue out again to show that I have indeed swallowed. Master patted me on the head “Good job Cindy, I feel better already”
He buttoned himself up again and took out a piece of paper. It's been nearly a month, it's time we set the boundaries in this relationship”
I studied the paper and it was a chastity contract. It scared me and at the same time excited me, I skimmed it and saw words like “Duty”.
It outlined how I was to be kept dressed as a woman, the times I would be in uniform (a maids uniform), that I would be kept corsetted. Most of it involved no change from what we were doing now, I just needed to agree to what I was already doing and loved doing. It also included a pledge that my Masters comfort and pleasure were going to be my only concerns. This I didn't have a problem with, I love serving Ben. Over this month I've found myself growing more and more submissive. When I know I've made him happy I feel a sense of joy more powerful than anything I've ever felvand want to wrap myself up in it. Little gestures like a pat on the head, receiving praise – all things remind me that Master is the center of my universe.
Where our signatures were to go, I saw additional conditions. Each one had space for signatures at the side. These were clauses that we would agree to later, a change to the conditions that required consent.
1) Extent of Chastity – The submissive relinquishes all control of orgasms to the Master. Release and orgasm will be at the sole discretion of the Master
2) Revocation of Safeword – The submissive relinquishes the right to a safe word. All play or punishment will continue until the Master concludes it.
3) Consent to Punishment – The submissive consents to any and all punishments the Master chooses to impose.
He saw the fear in my eyes when I read these last 3 sections. “Don't worry, you don't have to agree to those. If the time comes when you're ready, you can choose to accept them.”
He passed me a pen. “I'll understand if you don't want to do this. But I just want you to know that I've been proud to be your master and this has been the happiest time of my life.”
“Master, I am proud to serve you and I yearn to be the best possible submissive.”
I took the pen and signed the document (not the additional clauses, I knew I wasn't ready). As I signed my name I felt a wave of euphoria flow over me, I felt as though I might cum in my chastity belt there and then. Master took the document and signed it.
He placed it down on the table and placed his hand on my cheek. In that moment I knew this felt right, it felt wonderful. I closed my eyes and let my face rest against his outstretched palm, I felt at peace.
I whispered “I love you Master”
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