The Boss

by Shy Stuart

7 Jul 2019 2793 readers Score 8.6 (52 votes) PDF Mobi ePub Txt


It's Friday morning and I can't wait until 5pm. As I explained before John, my boss meets with a number of reps once a month on a Friday afternoon and goes for lunch up at the local Italian restaurant. John is partial to a good bottle of red wine and is often in no state to drive home at the end of the day. Usually it's one of the girls who drive him home but now it's my job. His wife is away until Saturday afternoon so the plan is to spend the night together. John is the first man I've had sex with and I can't wait to lose my cherry with him.

The reps start arriving about 11am and John asks me to go down and greet them. John's office is too small so they all congregate in my office. Five men turn up they smell and look good in their suits. I can tell from the conversation that they are disappointed that Pauline is not here anymore but I love being surrounded by all these men.

Unsurprisingly with a group of men like this they talk about their exploits with women. They try to out do each other with regard to how many office girls they've bedded over the years. John looks over at me and rolls his eyes, I shake my head and smile.

There's a lot of noise and I find it difficult to concentrate on my work and my mind starts to wander. I imagine myself in the restaurant with John and all the men. I'm naked except for a studded leather dog collar. John leads me up to the men's table and introduces me as his bitch. John parades me around the table letting the other men touch me in any way they want. John tells them if he gets a good deal then his bitch (me), will crawl under the table and suck them off.

I'm deep in my fantasy world when I hear...

"Stuart, Stuart, STUART!"

I look up at John startled.

"Stuart, we're all going up to the restaurant now, can you hold the fort until we get back"

"Yes, sure John, sorry I was miles away".

John and the reps head off leaving me to my little fantasy world.

I doubt John is the sort of guy who would want to share me with other men but I like the idea a lot. I tell myself to slow down. I'm still a virgin and haven't even been fucked by anyone yet but here I am thinking about being gang fucked.

My mind wanders again and I imagine John has me bent over the desk. He pulls my trousers and pants down around my ankles and parts my bum cheeks. He invites each of the reps to fuck me in turn.

Wow, I'd love that. I get up from behind my desk undue my trousers and pull them and my pants down around my ankles. I reach around and fondle my ass, sliding my finger down my crack and circling my rosebud. I spit on my fingers and work them into my ass. I look around the office looking for something to shove up my arse. In the bin is a tin of women's deodorant. It must be Pauline's, I laugh because it's penis shaped. I spit on my fingers and get my ass all wet working the tin inside me.

I can hear the girls laughing downstairs and I imagine them catching me in this position. What would they say, would they call me a faggot. I can imagine them laughing at my pathetic little cock dangling down between my legs.

Suddenly the door opens at the foot of the stairs and I can here two girls giggling as they run up the stairs. The tin pops out of my ass onto the floor and I quickly pull up my pants and trousers and sit down behind my desk.

Sue and Penny come bounding into the office.

"What are you doing Stuart?", they ask.

"Working", I reply.

They look down at the floor and laugh.

"Are you using Pauline's deodorant?"

Sue bends down and picks up the deodorant.

"Yuk, it's all warm". she exclaims.

I snatch if off her and explain that it was by the radiator.

The girls laugh and walk out the office into the canteen where I hear them both burst into fits of laughter.

I decide I best behave for the rest of the afternoon and I get on with some work.

John and the reps come back about 3:30 and I make them all a drink.

They are all in a very jovial mood, joking that I don't look as good as Pauline. Even teasing John that I'm not likely to be taken away overnight on business anytime soon.

John looks flush, is it the red wine or is he blushing from the last comment. Either way he looks over at me and smiles.

One by one the reps head off home and I'm alone with John.

"You still ok for tonight?", he asks.

"I can't wait, I've been horny all day", I reply

John gives me a knowing smile and asks.

"Is that because you're looking forward to spending the night with me or because you've been surrounded by six men for most of the day"

I laugh at the suggestion but admit to having a little fantasy about all the men at one point.

John laughs.

"Naughty boy. I thought you were daydreaming. Go on tell me about your fantasy".

I hesitate wondering if I should tell him but he encourages me to spill the beans.

John listens intently to my fantasy.

"You're a dirty little fucker. Apparently I'm the first man you've been with and yet you're already fantasising about a gangbang".

I apologise to him but he tells me he loves it and would like to hear some more of my fantasies, perhaps when we are in bed later.

John tells me to log off the computers as he wants to leave early. He goes downstairs to make sure Frank the foreman knows the locking up procedure. Then we head down to the car saying goodbye to the girls in the office on the way.

I jump in the drivers seat and carefully pull out of the car park onto the main road. I slip my hand between John's legs and he squeezes my hand.

"My wife used to do that when we were first together", he smiles.

"I'd love to be your man wife", I reply.

"Well you're certainly a better cocksucker than my real wife", he replies.

"Hopefully I'll be a good fuck too", I reply.

The journey to John's house takes 30 minutes and soon I'm pulling up on his drive.

He opens the front door takes my hand and leads me inside.

To be continued...