Life Is Beautiful with Chaplin

Story Info
Seeking promotion the anal way.
2.1k words
4.23
15k
1
Story does not have any tags
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
alexcarr
alexcarr
332 Followers

Life Is Beautiful with Chaplin (Unabridged and edited version)

Jo Chaplin was the chief executive and I had one hell of a crush on him. I knew he was loaded but that wasn't the primary reason I wanted to get his notice, with me just being a mere accounts assistant I wanted promotion. I fancied my self as the boss's new male secretary he had been advertising for.

A colleague, who was also a good office pal, knew what I was up to and said that if I carried on perking my hind when I delivered statements and papers into his office I may get more than I bargained for.

"You have noticed have you Jason, is it that obvious?"

"It is for me, Pete. Very nice and tempting indeed, I may have made a move but my partner John keeps me fulfilled" he said with a wistful smile.

I carried on flashing my ass every time I went into the office. Occasionally, accidentally on purpose, dropping documents and bending to pick them up again, showing my best to the boss in the most provocative way, my tight fitted tailored trousers giving of its very best.

It worked, Chaplin asked if I could stop over.

"I want you to do a few chores for me Peter" he said with a glow on his cheeks that said he wanted me.

It all started with a stain Chaplain had noticed on his desk, He asked If I was any good at French polishing to hide the offending stain which annoyed him intently.

Seeing the opportunity, I immediately said I would try and with lots of intense rubbing and bending I gave it all I had got - given a small bottle of French polish and a good cloth.

"I adore the way you jerk that wrist" he smiled and their was an innuendo there.

Of course I made sure I emphasised my movements, especially as I bent over - giving Chaplin the closest of close ups and I guess I anticipated that sooner or later he would surely not be able to resist a touch, a stroke or something more. I felt that confident, it was not rocket science to see he was very interested.

"Your bum is as admirable as your French polishing Peter, a sheer worked of art and a sight for sore eyes. May I?"

He gesticulated with his hand what he would like to do, and still bent provocatively across the desk I gave him the nod and when he applied that first touch it was so nice I wanted more, and more, and more!. I gave it a slow wiggle and squeezed my buttocks tight together and he touched me more Already I felt the familiar tingle creep along my rectum.

"You know I noticed you from the start Peter, when I interviewed you for the post. I am so pleased you are coming up to expectations. Would you like me to do more, I would like that so much if you would?

I was in my element. Surely this would lead to promotion and I replied the pleasure was as much mine.

He indulged and for the next few minutes I was spoiled with lots of stroking, nudging and a few light slaps.

"You are beautifully crafted front and back" he commented as he started to run his ham through between my trousers and cup my balls

"Delightful Peter, you really are. Can you let me see you now, can you drop your trousers. I will mine too so you can see me as well."

It was all very exciting and thrilling remembering it was my very first time with another guy, doing all those rude things.

And my deep carnal thoughts could think of nothing else at that point

"That is beautiful Peter, What a shame to keep it trapped away all day and that fine hind of yours too"

He touched my cock and watched it rise which amazed me and thrilled him, I never would have thought I would have gotten an instant hard on with another guy.

"How does that feel Peter? he asked squeezing it between his thumb and forefinger, making it all feel very lovely and stimulating.

I whispered it felt good.

"And this?"

He stretched back the foreskin at which point I was concerned about the smell. It always smelt when I did that. In fact when masturbating it had often put me off until I gave it a good wash, remembering the rule of thumb when my mum used to say to ensure all the cheesy residue was cleaned out from behind the fold, else no girl would want to know me. It is funny how something like that remains.

"I had better nip off to the bathroom Jo and clean up huh?"

But he was already in his own little world I could tell. He did not seem to react unfavourably. In fact he seemed to savour the scent and I watched his nostrils draw in and his eyes close as he inhaled.

"I so l love the scent or ripe young cock" he exclaimed. "Now turn for a moment and let me smell your ass also."

Now my mind was saying to my mum that I was being a naughty boy, letting another guy suck me, and with all the cheese too!

But then, prompting me to lean full over the desk again I was treated to the most delightful sensation, he just lapped me up, slapping and licking it all over and my asshole too. I was in my element and thoroughly enjoyed his exploration of me. My cock was rock hard and wanted release and he thought of that too.

"Was that nice Peter?. It was for me, It was yum-yum and I adore your smell and taste, it is the real smell of sex and it makes me so very randy, so you hade better watch out, it's not just my finger I want up there, your ass is made for fucking and no mistake, and I am the one to fuck you fair and square.

He manually twisted me that way and this way so he could get the best out of me and soon he was sucking my hard pulsing cock to the extreme, prizing it upwards as he licked downwards, there was no sign at all that any cheese residue was putting him off, so at last I could get the image of my mum well and truly out of my mind and just enjoy what this wonderful guy was doing to me. He cupped my balls and licked them too - all over and around and around - it felt so wonderful, and then down again, until prompting me to open wide, he manoeuvred his face into my crevice and I then felt the delight of his busy tongue licking my balls and ass.

"Beautiful Peter. I can see you want to cum. But what about a bit of spoiling from you. Look I have a real hard one for your pleasure, can you maybe give him some of your French polishing movements, I loved to see the way you flicked your wrist and was thinking I could do with a bit of that."

"I touched him, apprehensively at first. It was the first time after all."

"Squeeze, like I squeezed you. Give it some zip. You like it don't you? And if you are really good I shall give you a beautiful feel of it up that beautiful asshole of yours."

I closed my eyes and went for it. It felt good. I liked the way it jerked upwards every time I squeezed and when he asked me to pull back the foreskin. I realised his smelt just the same. For the first time I enjoyed the scent of cock,. It made me more sensual and tempted me to go further. Like to stretch my tongue out and lick its p-hole."

Jo was making all sorts of rapturous s noises which gave me the confidence to carry on doing what I was doing. I indulged first in some gentle sucking. It tasted earthy and interesting and quite by chance I found myself cupping his full ripe balls too, starting to really enjoy this wonderful new experience my life.

All the time I was feeling too a more wonderful sensation in my back passage than before - which seemed to ache for the feel of something up inside ,and I guessed this was brought on by Joe's constant teasing there, ringing his fingers around and around and occasionally prodding with some lubricant he seemed to produce magically from his desk drawer, like he knew what to expect.

We played intensely with each other, simultaneously indulged in oral sex and it was something so special enjoying each other that way.

"Watch this Peter" he said taking his reception firmly in his hand and thoroughly wanking himself. He held it pointing rigidly upwards and when he stopped wanking, just for a moment nothing, and then a huge grunt and a showing of a ball of cream oozing from his p-hole.

He wanted me to lick it off, he said that would be so sensual and so tender. So this was another first time for me. It did not seem at all repugnant as I went down and expressed my tongue, closed my eyes and rolled his glans into my mouth, tasting instantly the sea saltiness of his sperm which seemed so perfect and right that I should be doing that. "Let me see it role in your tongue and then swallow?" he asked and I gave his a good display.

Rubbing his fingers more deeply into my ass he asked if I would let him fuck me, preferably across the desk because that makes for the best position to reveal my ass at it's very best.

By that time, having been thoroughly primed, my asshole was his and when I said I would like that, his face lightened up and he gave me another real deep throat suck.

Then stretching my as cheeks so wide apart I felt him start to rub his cock all over my ass until it reached the desired spot.

"Open a bit wider, I want to get full penetration" he said and I felt is start to surge into the opening.

In he went, steady at first and then gradually speeding up as I felt the surge of hot hard cock enter me deeper and deeper inside, hurting at first until I was fully stretched and then it was beautiful the way he slid it in and out of my ass so smooth, stretching and slapping my ass soundly between each thrust.

When he paused awhile I thought that was it and he had cum. But this guy knew just how to make it last, by stopping occasionally and taking in the pleasure of our mutual throbbing.

It felt almost like being handcuffed and tied down , it was so deep up inside that I could not have gone anywhere even if I had wanted. But the reward of that lovely seven inch driving throbbing cock up inside me was perfection and I loved it.

Then it happened. I felt the surge of his cream spurt inside, he took my cock in his hand and gave me such a stuff hard wanking I screamed with pleasure as I shot my load. It felt like it was drawing every spurt deep form my balls, and when Jo squeezed them, I cum again and again. He wanted every ounce of what I had to give.

Then well holed and fucked we took time to take in the wonderful aftermath of the extreme pleasure we had enjoyed of each other.

"I reckon you will make the perfect secretary" said Jo afterwards. It had gotten to he letting me call him by his Christian name.

"That way I can have you when I want you" he grinned.

I knew then I was going to be in for an awful lot of fucking and I really got to know his various deviations into prime sex in all sorts of modes. And usually after office hours when he could dress me up just how he liked and wanted me, He loved role play and I loved to do it for him.

It was fun being in a dinky short skirt and he pretending my ass was quinny, I imagined how it would feel to be a girl, he powered me up too and smothered me with perfume, It was lovely.

Now I am a fully fledged and well fucked secretary, treated to lots of nice presents and cool dinners afterwards, when I am sitting down and still feeling the numbness there of his fuck and deviations.

Life is beautiful with Chaplin.

alexcarr
alexcarr
332 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
4 Comments
alexcarralexcarrover 10 years agoAuthor
Life is beautiful with Chaplin (Unabridged and edited)

Chesterslave - I have edited and submitted an unabridged version for your perusal

chesthairslavechesthairslaveover 10 years ago
'And This?'

Once the reader gets past the errors in spelling and grammar the storyline welcomes the reader to a happy ending.

AnonymousAnonymousover 10 years ago
Longing for more

A wonderful idea! I immediately had a hard-on und woluld have loved to be in Petes place. It's a pity you did not tell more details, I would have loved to read more about how Chaplin looks and especially more about the role play after office hours.

AnonymousAnonymousover 10 years ago
Life Is Beautiful With Chaplin

I am a classy, mature male to female crossdresser, and enjoyed the story very much. I would love to be someone's secretary and have a similar job!

Sincerely,

Josie of Augusta, Georgia

facebook: Josie Augusta

email: josie.karaoke@yahoo.com

Share this Story

Similar Stories

Rainbow Stone and Tile Two Hispanic men save the day and find a big cock daddy.in Gay Male
Gym Daddy Hot muscle daddy surprises horny teen.in Gay Male
The Steam Room Story of my experience in a gay sauna.in Gay Male
South Bound And Down First time with a guy.in Gay Male
Swallowing a Whopper I suck a big cock all the way down.in Gay Male
More Stories