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Chapter 2 of A Businessman’s Sissy
David and Samantha’s relationship evolves to show they have found their perfect companion. Samantha is shown how she is expected to serve her new master.
***
Samantha looked lovingly up at David from under the desk as he smiled at her and stroked her cheek. She felt incredibly close to him having only met just a few hours ago. Knowing next to nothing about the man that she had just given her mouth to and yet it felt natural to be his.
David got to his feet. “Wait right there Sissy.” He walked off in the direction of what I assumed was his apartment just next to his large office. David emerged with a collar and leash in his hands and attached both to my neck pulling gently upwards until I was stood behind his desk. “You’ll spend many hours bent over this desk as well as under it Samantha, I’m very excited to show you how you’ll integrate with my life but it’s very important to me that you’re 100% behind this every step of the way. What I desire is more a sissy wife than a sissy slave. As such you must have a safety word to put the brakes on if you need to, what would you like it to be?”
Samantha paused for a second. Her pert panty clad ass perched on David’s large desk. “Impossible sir.”
“I’m not sure I follow Sissy… do you not want a safety word? It’s important for both me and you.” David questioned.
“You misunderstand sir…I would like my safety word to be ‘impossible’ because I don’t believe a man who has treated me so kindly, dominantly and passionately as you could ask anything of me that I would not consent to. It seems ….. impossible.” I sighed.
David smiled the broadest smile. Clasped his hands around my shoulders and kissed me deeply, his tongue explored my mouth. I was so deep in sub space my only thought was “I hope this kiss feels good for him”. He released me from the loving embrace, took hold of the leash and instructed me to crawl alongside him.
“I’ll walk slowly sissy, it’s important you get used to crawling as it’s all you’re permitted to do whenever in my office or apartment for now, it’s a good thing I have plush carpets fitted! Unless I state otherwise when I am present in the room you are to be on your hands and knees. When I am in another room, the shop or out you may stand.” He exclaimed as I crawled along with him taking in my new surroundings as we made our way through the wooden door into his lounge area.
“I live here in the week sissy as will you, we’ll be spending what’s rest of the weekend here on this occasion to get used to the place before I show you my house out of town. It goes without saying it will be your responsibility to keep this place clean and tidy as well as the shop floor and office. You needn’t worry about cooking as I take great enjoyment in that myself and all laundry will be sent out. You’re sole duties are to clean and….well ……to fulfill my extensive sexual needs.” He smiled grasping my ass and momentarily playing with the plug still tucked away. I squealed as David continued the tour. He went on to show me the luxurious bedroom, kitchen and dining area along with his bathroom complete with an enormous bath and double rainfall shower. My mind was running wild with all the ways I could be used in each and every room. I also started to consider how to clean the place, I was desperate to please David so he’d feel proud of his….Sissy girlfriend….There was a long road ahead before I could honestly consider myself a wife.
“It’s time we get to know each other a little better before we enter our new work week routine tomorrow Samantha.” David asserted leading me to kneel on a thick rug in the middle of the lounge before he took a seat on a leather sofa in front of me. I shuffled forwards to position myself between his feet bringing a grin to his face. He passed me my phone which he must’ve taken when I passed out earlier. I looked at him like a confused puppy. “I’ve installed an app on your phone darling. A comparability app of sorts which we both enter our interests on selecting whether we ‘love/like/dislike/hate/are curious about’. I’m sure it will be of no surprise that the interests are of a ….. sexual nature.” I don’t exactly have a poker face but I’m sure the look David witnessed spread across my face was one of uninhibited arousal. “Thought that would get my little bunny going.” David smiled. Bunny….I love that, I thought to myself.
We spent the next 10 minutes in silence with only passing smirking glances at each other. Not knowing what David was selecting drove me insane but to show how fully committed was in service to my new owner I threw caution to the wind and elected to open myself to almost everything…..
Anal (receiving) – love
Ass worship (giving) – love
Ass to mouth……this took some thought….. curious, I’m definitely curious.
Body modifications …. I’d looked into hormones before, surely this was what Alanya travesti it meant – curious
Butt plugs – love
Just the process of making my choices had my sissy clit straining at its cage.
Chastity – love
Cocksucking – love
Deep throating – love
Dildo play (receiving) – love
Double penetration (receiving) – love
My heart was beating faster and faster.
Face sitting – love
Gangbangs….surely David wouldn’t want this…….unless he had a small group of like minded good friends…..he had talked about ‘the community’……I’d read stories about this – curious
Gloryholes – love
I remembered my safe word, this gave me confidence to go on. Through the lengthy list. I was just over halfway through and must’ve made a hundred choices.
Oral (giving) – love (I may have given this away already *giggles*
Oral (receiving) – this felt wrong but not knowing how David wanted to mould me I wanted to leave it open, I chose dislike
Orgasm control – love
This 10 minutes seemed like a day, it was mind altering!
Rimming (giving) – love
Scat play…..
This was my longest pause. David must’ve noticed.
“Sissy.” I looked up to see David staring at me. “You must be honest but open to new ideas, I will never do anything I don’t believe you will love.” He stated.
Scat play ………….. this seemed repulsive …. but the glances I’d had at my mans ass had me entranced…. I took a deep breathe…..curious
Spanking – love
Water sports – love
I saved my choices and placed my phone on David’s knee. He grinned. “I hope you found that as exhilarating as I did beautiful. Come sit on my knee and we’ll see how we did.” I stood up with David still holding my leash and softly sat in David’s lap feeling his already erect cock poking my pert behind.
David screen shared his phone with the huge tv in the lounge above the unlit fireplace. It turned me on how he was in complete control but acted with such love and care. A fanfare came from the speaks as the words ‘Perfect Match’ danced onto the screen. David and I stared dumbfounded for what felt like an hour. Both not knowing the odds of this but they must be high. We turned to face each other and our lips met, I was in heaven and hoped my owner, my daddy, my god, my …man was as well.
There was a short list of interests we both rejected on screen when our passionate embrace ended. They included some of the more painful practice that may leave permanent scarring or public humiliation. We both looked at each other and smiled shaking our heads as David turned off the screen.
” I noticed there’s a few on there which may seem a little extreme that we both selected ‘curious’ for Samantha, I don’t have a firm opinion on everything myself. There’s some interests we may never try, some only on special occasions….like my birthday.” He winked cheekily. “I’m glad I found someone as open minded as me, my philosophy is I’ll try anything once…..well ….. most things.” I felt completely at ease with my choices straight away and David printed off a copy of the results and put them on a nearby bookcase. “I’ll fix us some food whilst you tidy up my mess in here sissy.” He winked. “Then I’ll detail what your routine will be from tomorrow through the working week.” He stood and walked towards the kitchen giving my ass a firm spank as he went. “As I remember you ‘love’ a good spank as I recall he smirked.”
Could I really be in my dream life. Am I going to be rudely awoken at some point before I’m awoken by a call from my awful b…..boss. Oh my word it’s Monday tomorrow and I was expected in work. I had no family to speak of or friends to miss me but I had a flat and bills to pay. I paced over to David who had already started on the meal.
“Sir what am I to do about my job, it’s Monday tomorrow and I……..”
“And you’ll not waste another moment on thinking of your old life Samantha.” David stopped me. “I’ve emailed your old boss from your phone with your immediate resignation, he was not too polite in his reply but needless to say you’re not expected anywhere other than at my feet tomorrow morning. As for your flat I emailed your landlord and gave notice paying the outstanding rent and bill amount. You could say you have a debt to repay to me.” He smiled to himself. “What you should be thinking about is did I give you permission to walk.” ……He had not. My face turned white.
“I’m so sorry sir I….” I started.
“Bend over the kitchen island with your hands behind your back Samantha.” David said without looking up.
I compiled immediately not wanting to displease him any further. How could I have been so silly.
“You’ll come to realise I’m a very fair man sissy.” David said as he put down the utensils and walked around behind me. I quivered nervously. “I expect obedience but I also expect you Alanya travestileri to fall short of my expectations sometimes. You’re only human little one. But you also need to know that lessons felt in pain aren’t forgotten quickly……WHACK.” His palm came down on my left ass cheek. I screamed out. “No noise sissy, this apartment is soundproofed along with the privacy film on the windows but you need to learn self control. For now I’ll help you.” He pulled my pink panties down my legs as I stepped out of them. He held them to his noise and inhaled deeply letting out a soft groan. He then eased my mouth open and tucked them inside.
“Hmmmm, not quite.” He seemed unsatisfied with the makeshift gag.
I felt a firm tug on my butt-plug as it slid out of my sissy pussy. He once again inhaled the scent of me before offering to my mouth which seemed to open automatically and seal around the jewelled base after he placed it inside. I’d never tasted myself before, my curiosity with ‘ass to mouth’ continued. My mind was more focussed on the remainder of my punishment to come. Another 9 slaps to my pinkening behind followed. David walked away but not back to his food preparation. He was heading to the shop.
I dared not move from my exposed position. A tear left my eye at the displeasure I caused my master, not to mention the stinging I felt from his hand. I heard steps behind me and the house of a packet being opened. “I was saving this for after we ate but seeing as you’re in a suitable position….” I felt a firm pressure on my sissy pussy. “The plug you came through my door with was cute but far too small for the plans I have for your pussy sissy, I have no intention on stretching you to the incredible levels you may have seen in some scenes you have perused online but we need you just the right size for us both to enjoy me making love to that pussy whenever I see fit.” If an orgasm was possible with a cage on, I felt it there and then. My eager hole swallowed the larger jewelled plug (David knew I loved my sparkle) with just a few pushes and twists.
I then felt my cage being removed, he must’ve removed the key from my wallet earlier. I didn’t understand. Before my mind could wander further…. CLICK. I was once again locked away. “The cage you had was ‘amateur’ level, you’ve now graduated to ‘pro’.” He chuckled. This is more comfortable for long term use but, more importantly’ is much harder to remove. That is unless you have the key.” David held up the key he was linking to the thin silver necklace now hanging down his muscular chest.
“I’ve another half an hour before food is ready sweetie, that lounge needs to be tidy by then so if I were you I’d ‘crawl my way back there’ and get on with it.” David said firmly whilst chopping the vegetables in front of him.
I had no desire to be told twice. I dropped to my knees and headed over to the lounge door noticing how much the larger plug made my ass sway, I could feel David’s eyes on me and swear I could hear a soft grunt as I made it to the door. I kept the special gag in as I hadn’t been instructed to remove it.
I closed the door behind me and hurried to tidy the clutter in front of me. I’d need to learn where everything was kept and work out just how David liked it but for now would just try my best.
The door opened and I instinctively dropped to all fours. “Very good sissy and what an excellent job you’ve done.” The words melted my heart. Time for tea though now darling. Crawl ahead of me so I can gaze at that jewel nestled between those cheeks and imagine the fun we’ll be having later. The words ‘luckiest gurl alive’ repeated in my head in time with my ass sways until I reached the table and stopped. “You may sit at the table and remove what’s in your mouth princess.” David said.
We both ate the delicious meal David had prepared (he really was a great cook), as David explained what I would be doing tomorrow and every work day from here on in as he detailed my schedule.
1. Our alarm goes off at 06:30. Awaken me with a blowjob or by worshipping in my ass depending on which way I am laying.
2. 07:00 Both get dressed, I will lay out the exact outfit you will wear, usually French Maid but not always the case, along with any other accessories I deem fit.
3. 07:30 As I prepare breakfast for us you will tidy the bedroom, lounge and bathroom (no cleaning, just tidying).
4. 07:45 Eat breakfast together.
5. 08:00 I will then begin work whilst you clean and tidy the kitchen then proceed to spend the morning cleaning the rest of the apartment.
6. 12:30 eat lunch together.
7. 13:00 I return to work whilst you continue to clean.
8. 17:00 shop closes and staff leave
9. 17:30 sissy vacuums, mops and wipes down surfaces in the shop whilst I prepare tea.
10. 18:30 tea together.
11. 19:00 ‘evening playtime’.
After David finished reading out Travesti Alanya the schedule he’d be pinning to the wall in the apartment he clarified something. “Now sissy, even a pretty little bimbo like you must’ve noticed there is a lot of time to clean the apartment there.” He was wrong, I was mainly focussed on adjusting to the new plug pushing deep inside me and trying to hear David’s words. He was right though, it wouldn’t take more than an hour or two to clean the apartment.
“You’d be right in thinking that Samantha, I spend most of my day in the office managing my online store whilst a couple of trusted friends run the shop downstairs but never come in the office. Whenever I buzz this intercom ….” He demonstrated by clicking on his phone and a buzzer sounded in the lounge. “You are to crawl on through to the office and then rise to stand in front of my desk to be given instruction. Do you understand sissy.”
It had been one day and I could barely remember my old name, let alone my old life.
“Yes Sir”. We finished the meal in almost silence, there was a lot for me to take in, a lot had changed for David as well, he may well have been thinking about his business but I’d like to think he spared a thought for the femmed sissy gurl eating with him. It was gone 9 by the time we were finished and it was clear we were both tired. David rose from the table first and walked behind me as I started to stand, he pulled the chair away and took my hand. Such a gentleman I thought as he walked me towards the bedroom. It was the inevitable conclusion of the most amazing day of my life but i was still nervous, would he want to fuck me, would he just want to cuddle, would I even be allowed to be in his bed with him? A pink see through teddy was laid out on the bed…when did he sneak away to lay that out for…..
“Samantha you are to change into this in the bathroom and then get yourself ready for bed, I have put a toothbrush and some feminine wash products out for you at what will be your sink from now on. I will give you privacy to do this but the plug stays in.” David walked out of the bedroom without another word. I walked through the adjoining door to the bathroom with my new teddy in hand. I spent the next 10 minutes calming my nerves, changing and washing. Still not quite able to take in all that had happened in the past 24 hours. Before I knew it I was stood in front of the mirror too nervous to move. I braced myself and walked towards the door, pausing before I touched the handle and smiling, I dropped to my hands and knees, turned the handle and crawling into my masters bedroom.
David stood at the foot of his bed scrolling on his phone, completely naked, when he caught my eye the phone went down and his mouth dropped open. “Simply perfect, on the bed on all fours now girl, this is the moment we cement our relationship.” I was in love.
I climbed onto the bed on top of the covers, aware of the fact my see through teddy hid nothing, especially not my cage or the pink jewelled plug which was reserving my ass pussy for David. There were mirrors adorning most walls, I had a full panoramic view of what was about to happen. I felt a hand around my plug and gentle pressure. Oh it was so big. Gradually with a little persuasion from David it came out, the cool air making me feel empty, needing filling. David walked around the bed to me. “Open wide princess.” I knew what was expected of me as the plug made it’s way past my greedy lips and my mouth closed around the flared base. I must admit, the sensation and taste were growing on me. I started to gently suck like a baby would. It was then I felt it, David’s huge cock was now slick with lube and the tip was now resting between my cheeks.
“Some nights we will just cuddle sweetheart, sometimes I will be away on business, sometimes you will lick my cock or ass to soothe me to sleep. However tonight I am taking your innocence completely”. With that he slowly started easing into me, soft music had started playing as I saw David toss a remote to his side. I glanced around all the mirrors taking in every view of this perfect man slowly but surely easing his perfect cock into my sissy pussy. It felt like heaven. I continued to suckle on the plug in my mouth which appeared to drive David’s desire wild whenever we caught each other gaze. His rhythm picked up and seemed to match the tempo of the music from my trance like state.
He gripped my hips and continued to pound away for minutes/hours/days….I had lost all track of time.
I sensed him tensing up and rhythm peaked he suddenly pulled me onto him holding his cock at its full depth as he growled deeply. “And now you’re mine….”.
Yes daddy I am. We collapsed with his cock still inside me. Feeling it soften I eased off him and delicately reinserted the plug as David seemingly amazed by my instincts whispered “I love you Samantha.”
“I love you to David” were my last words before I took his cock into my mouth completing my nights duties. I hopped out of bed to use some mouthwash quickly and then returned to my man under the covers with his arms outstretched. We fell asleep in each other’s arms. We had completed the first day of the rest of our lives.
Ben Esra telefonda seni bosaltmami ister misin?
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