This is just a short story on the day my boss realises I'm turning myself into a sissy. This probably story 4 of 6, 5 is nearly done and I came up with this scenario while writing that, again apologies if my writing isn't great, I'm not very good at writing down whats turning me on so much in my head
The workplace slut
Even though over the months I was feminising myself more and more, shaving, moisturising, growing my hair and meds, I was still hiding it in public, especially my workplace. Even though under my suit and tie I'd sly a nice feeling bra, panties and stockings and suspenders every day. I worked in a haulage company office, it was only small, only a few staff in the office every day and two receptionists. We dealt with all the admin and paperwork of the drivers that came in and out of the yard. Working late on a Friday my boss called me into his office. I really hated him, he always seemed to be an arsehole to me. He was the son of the haulage firms owner. Shaved head with a beard. I always said he was angry because he was a short man, five foot but he loved to work out, even with his suit on you could see how muscular he was.
I came in and sat down in front of his desk.
I sat nervously waiting for him to speak as he was checking some paperwork.
"Right Michael, I know you've been here for years and like this evening you've always agreed overtime and working late. But it seems your work has been slacking of late, just look at this pile of paperwork with countless errors" he said.
I sat there trying to hide my anxiety, honestly he was right, since I started this whole transformation, I wasn't concentrating on work much, more like day dreaming and fantasising about sissy's and cocks.
"Well what have you got to say slut" he shouted.
I jumped and shock came over me.
"What...what...do you mean?" I stammered
"You know what I mean, I've noticed you, growing your hair, more feminine" he said with a grin on his face.
"Erm well sir I can explain everything" I said
"I bet you can, now come here like a good girl" he said
I thought for a second and stood up, walked up behind his desk next to him.
"There's a good girl, now I can make this go away" he said as he grabbed my hand and placed it on his hard crotch.
I blushed as he forced my hand to grope his hard cock.
"You like that don't you?"
I slowly nodded.
"On your knees now or you're fired" he said.
I didn't know what to do, I needed my job and did I have a choice?
So I got on my knees.
"Under the desk you go" he said
I crawled under in-between his spread legs.
He unzipped his pants and his big cock sprang out of his trousers.
"Suck" he demanded
Honestly now I didn't know if this was punishment or a treat so I grabbed his cock with one hand and put his head in my mouth.
I started sucking and swirling my tongue around the head of his cock.
His cock was solid as I continued to suck on it, caressing his balls with my other hand. For such a little man his cock was huge, I was struggling to suck on it, it must've been at least 8-9inches but I tried my best. Alternating between sucking him off, sliding my tongue up and down his veiny shaft and sucking on his sweaty balls.
Then there was a knock at his door.
He grabbed my hair and kept my head down on his cock.
"Come in" he said
One of the receptionists came in
"Boss I've got some paperwork that needs signing" she said
"Ok love let me see"
I kept sucking as he signed the paperwork until she left.
"Oh that's a good girl, doing what you're told" he said
He slid his chair back and demanded I got up and undressed.
I took my jacket off, shirt and tie, shoes and pants and I stood there, in my bra, stockings and suspenders and my bulging wet panties because secretly I was turned on.
"Oh you do look quite sexy in woman's clothing" as my boss stood up, grabbing my small breasts with one hand and my wet panties in another. He kissed me on my neck and groped me for a few minutes. Honestly I wanted to bust my nut so hard as he groped around with his big hands.
Suddenly he stopped, spun me around and bent me over his desk.
He knelt down, pulled my panties to one side, spread my cheeks and spat on my boi pussy, then started to swirl his tongue around my hole, his hot warm tongue lapping up my shit hole, his beard was prickling my skin as he kept licking and swirling his tongue around which felt weirdly sexy. I was craving his cock now, all nerves had gone and I was turning into a horny slut for cock now as I moaned when he slid a finger in me, teasing my hole open as he continued to lick and prod at the same time.
Then he stood up, I lay there waiting as he stroked his cock and then teased it along my ass.
I involuntarily let out "oh fuck yes please sir"
As he continued to tease me.
Then he forced the head of his cock in my ass. Inching further and further in me, filling me up with his meat.
I could feel my ass stretching out. I grabbed the end of his desk as he slowly slid it back and forth in me then suddenly he thrust deep in me.
"Aaaargh fuck" I screamed
Then again, slowly sliding back then thrusted back in me
"Oh fuck" I screamed again as he continued, getting faster and faster with each thrust.
Every thrust got the same response as his cock rearrange my insides
"Oh fuck"
"Oh fuck"
"Oh fuck"
As he continued, thrust after thrust after thrust. I could feel my eyes rolling around my head everytime I felt his cock deep inside me.
Then his office door opened.
My eyes wide as he didn't stop. He didn't care someone had just walked in on us.
It was one of the truck drivers, back late after a delayed run.
He closed the door behind him and without hesitation he walked up to me, unzipped his pants and got his cock out.
He grabbed my hair tightly.
"Open wide" he said as he forced his sweaty salty cock in my mouth.
I couldn't stop him as I tasted his dirty cock in my mouth.
"There's a good girl, I knew you were a good slut" as he grabbed my head with both of his big hands and started to face fuck me.
He was only six inches but he filled my mouth nicely. Balls slapping off my chin, his big belly pushing against my face.
My boss still thrusting hard, pushing me into this driver with every thrust.
I felt delirious with his cock in my ass, I wasn't really taking notice of this drivers cock in my mouth because I was so on the edge of an orgasm. This must've went on for about 10 minutes, I was slavering down my chin, my body shaking and I felt out of my mind.
Then the driver thrust his cock as far down my mouth as he could, I couldn't see anything with his belly squashed in my face but I felt his cock throb and his sticky salty seed choke me as it hit the back of my throat. He held it there until his cock started to shrink.
He let go, slid it out as I coughed and caught my breath, cum dribbling out of my mouth as I started to scream again now I was free of his filthy cock. He zipped up and walked out without saying a word to the boss the whole time.
My boss stopped his rearranging of my innards and withdrew his cock. My ass felt as wide as a train tunnel as he grabbed me, lifted and spun me around and put me on my back, spread my legs, slid my panties to the side again and back in he went. Pulling my bra down now to reveal my little titties bouncing up and down with every thrust, he bent down and started to suck on one of my nipples, making it hard, I lent my head back and closed my eyes
"Yes Daddy yes" I moaned
He plowed on, I wanted to cum so badly, I'd been holding it back so much, at least 20 minutes of gagging to touch my cock and cum but the more I held it back the hotter I felt.
He stopped sucking my nipples and was really going to town on me now, my eyes were starting to roll around my head again.
He grabbed my hand and placed it on my wet panties.
"Cum for Daddy" he demanded
I didn't need to be told twice, his big hand holding my little hand groping and furiously pulling on my 3 inch cock through my panties.
I didn't last 20 seconds before I let loose
"Oh fuck I'm cumming I'm cumming"
My body shook and convulsed as I filled my panties with cum, still tightly holding my hand on my cock, cum soaking through my panties and making our hands gooey.
He didn't last long after that, my ass tightening up after my orgasm, I felt his big cock swell even more than before and he let out a loud feral groan as I felt his cock pulsate and fill my pathetic hole as he still held my hand tightly on my cock.
"There's a good girl" he said as he let go of my gooey hand, caressed my face and put two fingers down my throat as I sucked his fingers and tasted my sticky cum.
His cock finally started to shrink down, sliding it out and putting my panties back to catch his cum dribbling out.
He zipped up and told me to get dressed again.
I sat up, put my bra back up, shirt and trousers back on, tie and jacket and he told me sit back down.
Sitting there, soaking in his and my own cum, I was still shaky sitting there, I'm sure I had drying cum on my face too, I was stinking of cum and my boss facing me like nothing had just happened.
"Ok it seems we've come to an agreement on a new rolling contract" he said
"From now on you'll have to work lates on a Friday permanently but if this work ethic continues I don't see us having a problem with you in the future"
"You may go now" he said as he started to sign more paperwork, without looking up at me. I got up, cum dribbling down my pants and walked out.
From then on, every Friday I worked late. A new rota was drawn up and two members of staff were allowed to use and abuse me in the office, even the two young receptionists got in on the act, with their strap ons abusing my ass. All this so I wouldn't lose my job.