My shemale boss part 2

Friday 12pm was here, I nervously knocked at my bosses door part excitement part apprehension ran through my body.

A clear come in could be heard from within by my boss Miss Jones so I went in. Ahh Rob right on time, take a seat and I'll be with you in a minute, she said.

I sat down opposite her desk whilst she continued to study her paperwork. Her black rimmed glasses were on the tip of her nose and with her finger, she curled her long black shoulder length hair. Through her glass desk I could see her tight black leather trousers she had on and black 5" heals. She had walked through my office earlier in the day and I had nearly cum in my pants on seeing walk past in those tight leather trousers which made her ass look so perfect I just wanted to bite it .

She looked up and caught me druling over her leather trousers. Do you like me wearing leather Rob ? She asked. Kind of embaresed I replied, I think you look really hot today Miss JOnes. Thank you Rob she replied.

You look quite hot today too Rob, she said, so much so I want you to get your little Willy out and make it hard for me. What right here I asked ?. Yes she replied, I want you to entertain me by stroking your Willy.

Still fearful for my job and eager to please her I undid my jeans and pulled my cock out. I looked up and saw her deep blue eyes looking at me from behind her glasses, a smile on her face. I closed my eyes and thought of the other day when I had sucked her cock dry as I rubbed my dick, feeling it grow in size.

Now wank yourself off she shouted. I started to go to work on myself and was getting quite in to it when suddenly I felt a hard slap across my dick. Miss JOnes had got up from behind her desk walked over without me noticing and slapped me straight across my dick and balls. I let out a yelp to which she told me to shut up.

She grabbed my dick in her hand and proceeded to pull me to my feet by it and lead me round to her desk. I wasn't sure what she would want this time around. Would I have to take her cock in my mouth again or was she going to return the favour ?

Once at the desk she kneeled down and started to full undo my trousers. I couldn't believe I was going to be sucked off by this amazing shemale and be able to cum all over her glasses as she wore them. She pull my trousers down to my ankles looked up at me and smiled, I closed my eyes inanticipation but instead of her placing her lips around my cock she stood up and pushed me face down over her desk. My stiff cock got crushed against the desk as she bent me over and I yelped to which she laught. You didn't seriously think I was going to suck your dick did you rob you stupid little shit. You work for me and don't forget it.

She kept one hand on my back with her long nails digging in to my skin forcing me to stay on the desk. I then heard her undoing the button on the sexy leather trousers and pulling down the zip. The draw on her desk was then opened and closed and I suddenly felt the cold sensation of lube around my arse hole, two guesses to what was about to happen.

I had only just managed to fit her massive dick in my mouth let alone my virgin arse and I tensed up at the thought. I could hear her loobing up her cock behind me and then suddenly the feeling of the tip of her dick push between my arse cheeks and touch my tiny arse hole.

I then felt her try to push her self in to me but her dick was just to thick. Miss JOnes leant forward and whispered to me to relaxe and then bit hard on my ear lobe. As she bit down she use her strength and ripped my arse hole as she pushed her rock hard cock in to my tight arse with such f***e the desk moved.

I could feel the whole length of her thick dick inside me and although the pain was intense it was also a big turn on. Don't worry I'll break you in gently rob she said laughing. Miss JOnes then went to work on my arse. She did initially start off slowly pulling her dick out and slowly pushing it all the way back in but she proceeded to go faster and faster and it wasn't long before she was banging away, I could feel her balls slapping against me and the pain was getting worse. I bit down on my lip trying not to show how much pain I was in.

Miss Jones then eased off in her Fucking taking up a slower motion. Are you enjoying me fuck you rob ? She asked. Yes very much so mam I replied.
Wouldn't matter if you didnt you little shit she said, your tight little arse along with your mouth are both mine to do as I please.

At this point she reached forward and f***ed something in to my mouth, your need that to keep you quiet she said as you haven't felt anything yet. I then realised she had pushed her knickers in to my mouth and could taste her in my mouth. Miss JOnes then really fucked me, the back of her arm on my neck kept me down and periodicaly she spank my arse.

I didnt know how much more I could take she was showing no mercy to it being my first time but all of a sudden Miss Jones gave one final deep push and I could feel her hot cum fill up my arse hole there seemed to be so much and she pushed herself in a couple more times before finally pulling out of me and as she did so I could feel some of her cum run down my leg.

Miss JOnes then gave me a light tap on my bum and said very good Rob, your arse was wonderful perhaps one of the best I've ever had, now lick my dick clean. At that she sat in her chair and made me kneel in front, licking the remaining jizz off her now slightly limp but still large cock.

On licking her clean to an acceptable level she told me to get up and leave. On pulling up my own pants and trousers I went to leave. As I walked she could see I was in pain but I could just hear her laughing , clearly very happy in how she had broken me in.

Don't forget Rob, your my little bitch and I'll be needing u again soon. I said nothing and just closed the door.

To be continued
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Categories: Shemales
Posted by big_rob49
1 year ago    Views: 3,232
Comments (8)
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5 months ago
I've never had a real job think I'd be good at that position though :)
11 months ago
she need another employee?
1 year ago
I want to be her employee
1 year ago
My tyoing skills arent that great but I'd love to take DICKtation! great story.
1 year ago
yes are you hiring
1 year ago
Are you hiring? It sounds like you have a great benefit package.
D_and_J_69
retired
1 year ago
Brilliant...Di
1 year ago
Yes the first time always hurts like hell the next time will be better
thanks
Jay