My New Life Ch. 06 - Secretarial Bliss

Story Info
Secretary sex and spanking.
2.1k words
4.3
5k
5
0

Part 7 of the 13 part series

Updated 06/11/2023
Created 11/03/2021
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
Sambi123
Sambi123
30 Followers

Chapter Six-Secretarial Bliss.

I quickly undressed from my maids uniform taking my time to remove my stockings without laddering them, it looked like I had some hand washing to do but that could wait till the next time I was a maid.

Once naked I carefully put the outfit away hanging items that needed hanging and folding the apron and placing it in a draw. I then turned my attention to the secretaries outfit I had bought. It consisted of; a noticeably short black RA-RA pleated skirt which just a few centimetres below buttocks, exposing the tops of my white thigh high stockings, silk full fit white panties and white silk lacy bra, both bra and panties had a little pink bow in the middle with side panels in lace. Followed by a crisp starched white almost see-through blouse, choker, and bangles, if only my wife would dress up like this so I could fuck her hard, perhaps I could ask? No harm in asking hey!

I sat in front of my computer and searched for secretary porn, it showed several videos of sexy secretaries having sex on desks, photocopy machines and in the toilets, some in bondage gear or plain just getting spanked!

I managed to find one of a secretary preparing for work by having a shower and dressing from naked to fully clothed, so I followed her example.

First panties making sure that they fit nice and snug and snapping the waist band just like she did, then the bra all white and lacy, pushing my tits up and out nicely. Next came the white stockings, I rolled them up and pulled them over my toes up past my knees and finally to my thigh tops. finally, blouse, and skirt. The skirt was truly short and a little floaty it came complete with a lacy silk hem that just poked out from behind the skirts hemline, the blouse was nicely taut across my breasts and picked out the lace of my bra and the straps. Then the white stiletto heeled shoes slipped on comfortably and I was done.

I once again filmed myself doing various poses for the camera and computer, but this time when I bent over I was flashing my full pantied behind. I went back to my computer and found a film of a secretary getting punished by a lecherous old manager with desire in his eyes.

Sally knocked on the janitors door, whilst the camera panned up from her heels to her black RA-RA pleated skirt. The camera sensuously followed the line of the seam resting momentarily on her shapely calf's, then upper thighs, her silken white panties, and finally the back of her blouse tight across her shoulders showing off her mid back long blonde hair.

Sally waited nervously after knocking for what seemed an eternity before she heard a booming voice say, "COME IN."

Sally entered the room and walked over to the janitor as he beckoned her to stand beside the chair he was sitting on, white blouse, slightly open and taught across her breasts, her breathing making her chest rise and fall. She stood legs slightly apart, hands behind her back, head bowed, as he ignored her and continued reading the paper. One of his hands soon found its way under her skirt, felt her inner thigh, stocking tops and started to finger her pussy, she gasped as his rough hands stroked her upper thighs and expertly played with her, gently rubbing over her pantied pussy with two fingers and she gasped at this intrusion of her sex as he slipped a finger under her panties.

After twenty minutes of being fondled, he ordered her to bend over his lap, hands and feet touching the floor, her skirt lifted and tucked in on itself. His large, calloused hand was rubbing from the back of her knees up to her large round firm bottom. Her camel toe showed in her white panties being defined by the semi-translucent wet patch on the gusset of her panties. Low moans of pleasure were escaping from her soft pink lips as he probed and gently rubbed her sex from top to bottom.

He eased her panties down exposing her shaved pussy, her pussy juices glistening from the lights, he stopped rolling her panties when he reached her knees. His hand and fingers doing all the work, he placed one hand in the middle of her back and raised his free hand till it was well above and behind his head.

"keep your head down Sally" she obeyed her long blonde hair falling hiding her face, hiding her fear and tears at what was to come, and In one swift movement his hand swept down and made contact flat with the target. The girl was taken by surprise and let out a long loud yeeeooooow!!!!!!!!!!! Her head snapped up and she tried to get up, but his pressing hand kept her over his lap. He raised his hand again........A sharp harsh and fast downward SLAP.....full palm.....full on the buttocks of the hapless girl.

Another wailing YEEEEOOOOOOWW!!!!!! Escaped from her contorted face, little tears began to gather in the corners of her eyes as the flesh of her buttocks slowly revealed the red palm print from the two slaps and the sting from the slaps began to make an impact on her behind.

"Please Sir.....No More.......please...........I can't take anymore sir.....................I am sorry I messed your tea up............PLEEEEEEEASSSSSE............." as another sob escaped from her pursed lips. "I'll be a good secretary from now on, I promise, Sir!"

"Why Sally that's only two, the normal punishment is six of the best, you knew my rules when you took this job, now you have four more to come girl, you need to be punished GIRL?"

"Yes Sir, I know the rules SIR......but please have mercy please."

Sally felt fear grow in her stomach, she was petrified about the four more slaps, she tensed her buttocks which made a firmer target for the janitors hand. Her pussy betrayed her though as it became wetter, and a warm pleasant tingling sensation radiated from her sex as she eased her bottom up to meet his pussy probing fingers.

"See Sally you must like it, your body betrays you, you are nice and moist what a pain-slut you are?"

"Yes Sir.......Thankyou.....please be gentle as a slight moan of pleasure escapes from her lips, ooooooo...oooooooooo" as his fingers probed deep into her wet pussy, deeper, deeper still as they massaged the inner most parts of her pussy.

Two hard slaps in quick succession made her scream aloud and the tears flowed down her cheeks. Her bottom took on a lovely hue as the handprints turned her pinkie-white flesh a bright red. Her exposed pussy burned with sexual fire as the pain and pleasure sensations mixed and danced in her body.

The last two slaps were spaced far enough apart to make her a little afraid of the last one. A sharp SLLLAAAPPPPPPPP followed by a YEEEEEEEOOOOOOOOOOOOOO........"NOOOoooooooo.. please..

...........................Pleeeeeease no more SIR." The Sir escaped her lips involuntarily A long wailing cry escaped from her mouth followed by several sobs and tears.

The janitors pushed two fingers into the young secretaries pussy and felt her wetness, Sally wriggled on his lap, and she blushed and responded to the feel of his fingers by pushing her pussy further back onto his knuckles.

" Please SIR NO MORE.....I can't take anymore please sir. I'll do anything to not have the last slap please SIR?" as she began fucking herself on his fingers. The master knew he had her now, soon she would be his, he said.

"One more to come Sally, just one more surely you can manage to take one more hey SALLY?"

"YES SIR.....SOB.......please......SOB.......not to........sob...HARD...............SOB......please SIR!"

The Manager raised his hand high and brought it down fast and hard on her already sore and redden bottom leaving yet another handprint to merge with the others already combining into one big red messy, sore, stinging blob.

"OOOOoowwwwwwwyyyyyyyyeeeeeeeeooooooooo..........." Sally screamed, as her orgasm broke over her, she was broken she knew it and her body went limp over his knees, tears streaming from her eyes and dropped onto the floor, Sally sobbed uncontrollably for several minutes whilst the manager gently caressed her sore bum and touched her soaking wet pussy. He felt the heat from his spanking as much as she did, it radiated from her anus, around and in her pussy and then to her lower thighs and up her back. His hand rested on her hot bottom and gently rubbed in an oval fashion often pushing his fingers into her hot wet pussy. He could smell her arousal and she felt his hard-on through his trousers, she knew that in a few minutes she would be riding that monster for all she was worth, bringing herself to another shattering orgasm.

She sat astride the janitors lap and impaled her hot swollen wet pussy onto his cock and as she sank down deeper on to it she let out a slight moan of pleasure, followed by more louder moans.

"That's it Sally do you secretarial duties and ride this old janitor's cock for all your worth."

The panting girl increased her pace up and down, faster, and faster, backwards, and forwards on the janitors cock, rubbing her pussy walls raw against the large bulbous head of his cock. Reaching an orgasmic bliss, she came three times in quick succession and on the last of her orgasms he shot his load deep into her willing cunt, has he spasmed her pussy walls contorted and gripped his cock milking it for all she was worth, Sally was spent and dropped her head to his shoulders, her arms hanging loose over his shoulders, her legs gave way at her knees as she sank down onto his cock one last time. He gently patted her head and back and whispered, "Good Girl......Sally......SHHHHH......it is all over now........... shhhhhh......shhhhhh Good Girl." As he stroked her long blonde hair she kissed him passionately and whispered, "thankyou Sir."

Side note.....Sally was being blackmailed into having sex with the janitor ever since he had caught her masturbating in the toilets.

By the end of the video, I was at bursting point myself so I went and laid down on my bed, my panties had a sizable wet stain in the gusset area, and I knew it would not take much to send me over the edge one more time, I all of a sudden felt tired and I now needed a short nap after all that edging.

After I woke up I stretched and reached for the dildo, I was still horny as fuck my precum oozing slowly out of my gaff messing my white panties. I filled both balls with the cum substitute and set the timer for five minutes, just a quickie to get used to the dildo, but hey if it made me shoot my load quicker I would not object.

I removed my sopping wet panties and spread my legs exposing my fake pussy to the camera on the computer. I took my new toy and switched the vibrator sequence to up and down with a strong vibration. I knew I did not need any lubrication, so I slowly inserted the dildo into my fake pussy canal, the vibrations churned my retracted balls and excited my clitty. I was soon panting, and I was about to explode so I backed the dildo out a touch and let my orgasm subside. Edging was so much fun! It kept me on high for a really great orgasm if I could edge myself a few times.

After a while I felt my orgasm subside a little it was then that I then rammed the dildo in fast and hard and left it in as deep as it could go, I closed my legs, and I felt the vibrations tickle my clitty and balls. After the inserted dildo had rubbed my own clitty for five minutes and I came hard on the toy and not long afterwards it emptied both balls deep inside my fake virgin cunt, it slowly slows down to a gentle pulsing vibe and worked itself out as it plopped on the bed it faked the male spasms and shot one final load all over my groin area. I had been cream-pied by a dildo, the fake jism oozing from the gaffs opening mixing with my own juices. I was spent and could only think of a long sleep before closing my eyes I turned my computer off.

I fell asleep on top of the unmade bed wallowing in a mix of fake cum and my own ejaculate, my skirt was a ruined mess as I dreamed a dream in my sleep.

To be continued.............

Sambi123
Sambi123
30 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
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Fishnets / French Maid He wears his ex-girlfriend's lingerie - accidentally fucked.in Transgender & Crossdressers
A Double Date with My Wife My Wife and I Get Fucked Together.in Transgender & Crossdressers
Not Careful Enough Ch. 01 A boy isn't careful enough and gets propositioned.in Transgender & Crossdressers
The Red Panties Test Pt. 01 One night in prison will change Emile forever.in Transgender & Crossdressers
A Sissy's Awakening Ch. 01 A "straight" boi succumbs to sissy hypno.in Transgender & Crossdressers
More Stories