Clocking Overtime (for Sara)

Working late has never felt so good...

Transcript: It was happening again. Even though it happened at the end of nearly every workday, it still managed to come as a surprise. Sara could feel John’s strong hands squeezing and caressing her exposed derriere. Calling her into his office, John had simply bent her over his desk like a plaything and ripped her skirt down forcefully. Sara squirmed futilely beneath John’s rough grip; there was no escape. Her resistance however did earn her a hard spank. John grinned and Sara yelped, his large hand leaving a bright red brand.

Just a few months ago, Sara had been a junior executive in the company named Jay, until his scheming devious bitch of a secretary Devon manufactured a very compromising situation to blackmail him with. Officially, Jay was on vacation and John was his temporary stand-in, but in actuality Devon was the one in charge. As commanding as John was, John was only merely Devon’s obedient puppet. And with Devon holding all the cards, Jay too was powerless to defy any of Devon’s whims. Whatever Devon wanted, Devon got.

At first, Devon had kept up a façade of normality, still sitting at her desk out front playing secretary. She merely instructed Jay to let his hair grow out and keep the rest of his body shaved. Daily inspections ensured compliance. Then came the “vitamin pills”—feminizing hormones. Jay had tried to dupe Devon in the beginning by taking fake sugar ones instead, but somehow she always knew and would punish him with an aggressive double dose for several days after. Around the same time, Devon had had him start making personal trips to buy lingerie from brand name stores. The next day Jay would be expected to wear his purchases underneath his suit. It started with just panties—soft cotton, then cool satin, and eventually sexy lace—but soon Devon had him dressed to the nines: silk stockings, matching garter belts and bras, corsets, and basques. After work, Jay was to completely become Sara, full makeup, hair extensions, dress and all. Laborious at first, it wasn’t long before surgical implants replaced breast prosthetics and the course of Mother Nature as influenced by powerful feminizing hormones eliminated the need for shape wear.

After several weeks, Devon ordered him to come into the office completely dressed as a woman. Sara was to be John’s secretary. It had been a humiliating affair, walking in through the front doors past everyone who once knew Jay. Sara had earned her first spanking that day, for not looking pretty and feminine enough. It was a lesson she hadn’t forgotten; she hadn’t been able to sit for days afterwards.

Private meetings with John in his office, a disguise for daily inspections among other things, became common. Sometimes Devon would be present and give Sara demeaning tasks, or punishments for failing to complete previously assigned duties personally. One time, Devon had had Sara stripped and blindfolded, then throat fucked by what seemed like an endless slew of cocks—long, wide, big, and bigger—in the office break room for hours. If Sara so much as let a drop of cum go to waste, Devon made her lick it off the floor and then beg for more.

Occasionally, if Sara had performed exceptionally well, Devon would allow Sara a small reward, usually permission to touch herself for a few minutes, but never to cum. Though Sara was getting fucked almost daily, Devon hadn’t allowed Sara to cum for months now. Playing with her girlie cock was strictly forbidden; it wasn’t lady-like Devon had said. Instead, Sara’s girlie cock remained neatly tucked at nearly all times, staining the front of her panties with sticky pre-cum. Sara had made the mistake of thinking she could get away with secretly relieving herself once, but Devon had found out and forced her to wear a remote-controlled vibrating panty, keeping her on the edge for days. The constant promise but denial of pleasure had been excruciating. Sara hadn’t been able to bear standing straight for days afterwards due to the agonizing pain from her blue balls.  

Today, John was in an unusually playful mood. He was prolonging the groping and spanking. Sara winced with each sharp hit, but inwardly relished John’s attention. By now, her appearance was near perfect and John had certainly begun to notice. Sara was careful not to let on, but secretly she took great pleasure in the fact that John was fully hard for her.

Sara pretended to whimper while wiggling her perky ass subtly. She wanted John to want her without letting him know that she did. It worked. John picked Sara up and flipped her over. He was so large, so strong, he could have her anyway he wanted. Sara writhed beneath his grip. It was powerful, unrelenting, and domineering. Part of Sara wanted to be slip away from his grasp, but a stronger part wanted to taken. Sara gasped as John spread her bottom cheeks and entered her, not gently or tenderly, but possessively. With no regard to her groans, John took her as he pleased. Her ass was his and he wanted her to know it. But this time it was different. Sara could tell. This—John’s desire—was genuine. It was true raw carnal lust. John wasn’t just following Devon’s orders. He wanted this, her. And she wanted him.

Sara tilted her hips to allow him in deeper, moaning as she invited and took him in all the way. John increased his thrusts in vigor, faster and faster, harder and harder, until his hot sticky seed erupted inside her, filling her ass with fresh cream. The unexpected sensation was erotically satisfying, sending Sara over the edge and causing her own girlie cock to spurt a huge explosive mess—months of pressure—all over the stomach and breasts. Sara was glad it was already after hours, so that no one would be around to hear her screams of pleasure.

Sara’s chest was still heaving as John gently slid out of her, completely spent. Oh my god, that earth shattering orgasm had felt so good. She had almost forgotten how heavenly a climax could be. Then came the fear as she realized what had just occurred. If John reported this to Devon…Sara watched John’s face attentively as she anxiously awaited a reaction.

John finally spoke as he turned to leave, “Good work today, Sara. I’ll see you tomorrow. I’ll need you to stay late again. I hope you don’t mind.”

As if she had a choice. It wasn’t really a request. But Sara didn’t mind. Sara definitely didn’t mind.