A Businessman's Sissy Pt. 01

Sam was in a rut. A 9-5 office job with colleagues he'd rather spend less time around was grinding him down and he had nothing outside of work to distract him, socially awkward and insecure since a young age he had yearned for friends but never had the confidence to put himself out there. This also allowed Sam to more easily indulge in some of his own personal fantasies which up til tonight had been limited to cross dressing alone and acting out submissive scenarios kneeling on his bedroom floor with a small collection of dildos and butt plugs to play with whilst closing his eyes and imaging serving a superior. With his long blonde hair which was usually in a bun he was quite passable. Man or woman, Sam didn't care, he just fantasised about losing control of his body and mind in service.

Sam's phone vibrated, his manager had arranged drinks tonight and Sam had only agreed out of desperation to avoid another weekend sat alone in his flat. He'd need something to take his mind away for the night, he picked out a small pink jewelled plug, pink chastity cage and pink panties (he did love to match). The subtle movements of the plug would provide a distraction from the dull conversation.

The others had Pre drinks and were running late so Sam grabbed a drink and sat outside the bar on a little terrace. Scrolling on his phone hours seemed to pass, Sam checked the time....hours had passed! If this was a date it would be the equivalent of being stood up! Putting the embarrassment and sadness Sam resigned to finish his drink and head home to kneel and submit to a fictional superior and dream.

"Looks like someone's been stood up!" A deep voice came from behind accompanied by a hand on my shoulder, the tall and well built owner of the voice passed by me and sat at my table.

"No not quite...I.....I'm waiting for some friends...they're just..." I squeaked.

"You've been waiting an awful long time there sweetie, must be some friends, a real friend wouldn't be late, can I share a drink with you."

For some reason I glossed over him calling me sweetie.... "Sure I guess" I said trying and failing to deepen my voice.

My new friend introduced himself as David and called a bottle of wine over to our table. We chatted innocently enough about what we did, where we had been to school and where we were from. David seemed to be steering the conversation to my relationships, current living arrangements and how happy I was in my life. I was more eager than I'd normally be answering these personal questions by how comfortable David was with taking control of the exchange. I was as vague as I could be when David asked about having a boyfriend or girlfriend but David cut me off by saying "I believe I know the answer to my own question there Sam, ever since I saw your cute pink thong riding up your back...."

I was stunned, I couldn't believe how careless I'd been, my head started to spin but before I could stutter out an excuse David once again stepped in...." You needn't worry Sam, I understand people such as yourself, it pains me to you have to keep your true self hidden, you could say my true affections are for people such as you. I'm enjoying our evening together and would like it to continue, how does a walk along the canal sound, it's a lovely evening and we could stop by another bar for a drink along the way."

My mind had gone from utter fear at my depravity being exposed to joy that this beautiful sensitive dominant man of my dreams had sat by at my table and could lead to a life of my dreams, but I was getting carried away. "I'd like that" he nodded and we started walking, my hand gradually drifting to his.

"Have you spent much time in this part of the city?" David asked.

"A little" I replied knowing we were walking through the more ' LGBTQ+ friendly' area. I'd spent idle weekends quietly sitting on benches watching people who were clearly doms and subs go by imagining have a life where I could be free to be myself serving and being happy.

"I actually work in the area, saying that it doesn't feel too much like work owning a business in the industry that is also your passion" David said. Wow, he owns his own business, I wonder what it i....... David had stopped, still grasping my hand, on a quiet street in front of a medium sized commercial unit with a discreet entrance, I recognised the name from some of my horny Googling kneeling in my flat, could this man really own... "Dominant designs is my own little empire Sam, you may have heard of it, I'll show you inside, I'm sure there are many things of interest to a sweet little thing like you, I have an apartment just above where I spend a lot of my time, married to the job you could say."

I was in a trance like state, this couldn't be real, it was as if I was reading my favourite 'naughty' story but I was the main character. Before I knew it I was through the side door heading up a flight of stairs to a good sized office with windows out onto the shop floor below. My mind couldn't process what it was seeing, there were walls of dildos/plugs/whips/kinky clothing and areas with some of the most amazing furniture I'd seen; flogging benches, queening stools, stocks, sex swings....I'd seen many of these things on the website but being here in person with the owner who seemed to have taken a shine to me.... I came over all faint.

My eyes opened.... Had it all been a glorious dream?.... I was in the same office.....as I came to my senses I gradually sat up feeling a different texture on my skin and something in my mouth... "There she is, I thought you'd never awaken!?" David was perched on a large oak desk.

"I hope you like your first gift, I can't imagine it looking better on anyone." I was wearing a remarkably skimpy french maids outfit which rode up my ass and had little padlocks on, on my feet were black heels (also padlocked) similar to the ones I had been practicing prancing round my flat in, cuffs on my ankles and wrists, a dainty collar around my neck with a leash hanging from it and a small ball gag in my mouth. Logic compelled me to scream or run however my twitching caged cock and ass clenching my plug implored me to stay silent and listen to the man who had put me in this position.

"I'm glad you're calm Sam...Sammy....Samantha (he appeared to settle on Samantha as he smiled to himself), I've been waiting for someone just like you for years. Trawling online forums, meeting potential candidates, disappointed every time. But tonight I knew I'd found the one. As I said earlier I'm entranced by sissies. I'm also a very committed businessman in the process of making Dominant Designs an extremely profitable business with heavy involvement with the local 'kinky community'. I'd resigned myself to working hard for the foreseeable and focussing on the store and then you fall right into my lap. I want a partner who fulfils my yearnings for a sissy but also who caters to my domestic needs and helps me focus on work so I can grow my empire. A sissy who takes care of my....'needs'.... and I'll take care of them." David explained.

"You can back out of this anytime, I put you in your day to day uniform whilst you were out to show you my intentions as I'm sure you want this. All I need you to do to accept trying this lifestyle out is slide to your knees and out your hands behind your back." David went on.

I had assumed the position before the words left his mouth. I had an opportunity to live my dream life and nothing to go back to in what I now believed to be my old life.

David smiled, waking behind his newest, greatest and possible final conquest he locked Samantha's cuffs together and helped her to her feet. "I think we're going to be very happy you and I Darling, let me show you around your new home. You may have questions but save them for later, I'm going to keep that ball gag in for now to get you ready for a treat a little later."

We descended the stairs down to the shop floor with David grasping my arm to help my balance, it was well past closing time so it was just the two of us. "Welcome to my store, you won't be down here during business hours you'll be glad to hear but once my staff leave and the doors are locked you'll be down here for a few hours cleaning every surface and having a tidy up, maybe restocking a few shelves time dependant, you'll need to earn your keep! I you'll be dressed as you are now with a couple of little changes here or there depending on my mood. I'll be in the office keeping an eye whilst I'm empire building."

He proceeded to show me every aisle of sex toys, costumes and bondage furniture explaining what sold well and who bought what, my boy clit twitched in its cage at almost everything he showed me and I gripped the plug still in my behind almost constantly. once we'd toured the store and David showed me where the supplies were we headed back to the office area which was linked to his apartment, the whole area was locked off from the shop below with privacy windows so I had no fear of being seen David reassured me.

"This is my office where I run the store downstairs from as well as the online side of things. I won't bore you with the details, all you will be doing is keeping it clean and tidy daily with the supplies from the cleaners store. You must have so much going through your head right now beautiful I think it's time we both had a break for a simpler task."

David guided me towards his desk which was open at the back so I could see his large leather chair, standing in front of the desk my mind exploded, was he going to bend me over the desk? He released my cuffed hands, removed my ball gag and pushed me to my knees. "Stay kneeling" he commanded. He walked round the desk and relaxed into his chair. "Crawl forwards to me Samantha" he said calmly. I dropped forward and crawled under the desk, my eyes glanced up and I.....I caught sight of his cock, it was thick, long and only looked half erect.

"Take it in your mouth Samantha, the gag should have done its work. I want you to worship it, I don't want you to think about me cumming, just enjoy it, I have some work to attend to so you'll be there a while. You'll be spending a great deal of time under this desk."

I slowly took his cock into my mouth, it felt so natural, like it been serving David for years. I kissed the entire length of his beautiful cock, ran my tongue all round the head paying attention to every inch including his alpha male balls inhaling deeply to get his scent. I lost track of all time as I caressed and explored him tasting his precum as he carried on with his business disregarding me aside from the occasional head stroke. Sucking cock with no immediate drive to get him to cum seemed strange but oddly emphasised my subservience to David.

After what felt like hours David sat back. "You're doing so well sissy" he said gazing into my eyes and stroking my head with his cock still in my mouth. "You may now get your reward". I focussed my efforts building a rhythm up as I felt him straining more and more until he groaned grasping my head shooting ropes of cum to the back of my throat. I instinctively held my mouth open showing David's impressive load back to him, he nodded and watched me swallow it down.

"Yes Samantha, you're exactly what I need."