tagTranssexuals & CrossdressersStep Into My Office

Step Into My Office

byCal Y. Pygia©

All right, I admit it. I was an idiot.

I never should have worn the butt plug--if “worn” is the right word--in the first place, especially not to work, but I couldn’t help myself.

Okay, I guess I could have helped myself; nobody forced me to insert a plug up my ass. It’s just that, ever since Hermie left me for (of all things) a genetic girl, I’ve felt lonely--and horny. I guess my self-esteem was at an ebb, too--I mean, losing a guy to a genetic girl does nothing for a shemale’s ego. I thought a cock up my ass, even a fake one, might take my mind off my distress. After all, what girl doesn’t feel better when she’s “full.” It’s reassuring. It’s comforting. It’s like sucking one’s thumb, only much better.

I’d lubricated my anus and my rectum liberally with K-Y, crouched over the toilet, willed my sphincter to relax, and slowly, but resolutely, eased the butt plug into my ass until it was fully inserted. Immediately upon experiencing the familiar sensation of having my impaled bottom stuffed with cock, artificial though it was, I felt a good deal better about my situation and myself. The feeling of being filled, I guess you could say, was fulfilling. I’d also enjoy the knowledge that no one else but me knows that, beneath my skirt and panties, I had a thick, hard latex prick shoved up my ass. It made my cock swell as much as the butt plug’s pressure against my prostate, and it made my nipples stiffen beneath the fabric of my blouse.

For work, I’d decided to wear a simple white blouse, a mini-skirt, and a pair of patent leather pumps. I’d carry a small black clutch purse, with the tube of K-Y inside, in case I needed to visit the powder room.

My car was in the shop and, having just relocated to Las Vegas, I didn’t know anyone other than the people with whom I worked. I’d thought about asking a coworker for a ride, but I didn’t feel comfortable doing so. I mean, I hardly knew any of them yet. Instead, I ascertained which bus route would get me from my apartment to the office.

It was while I was standing at the bus stop that I realized that I may have made a mistake by including not only a faux pearl necklace, matching earrings, and a silver bracelet among my accessories but also the butt plug I’d inserted in my ass. I’d used a lot of lubricant--too much, it seemed. Despite its bulbous head, much of the butt plug had somehow managed to slide back through my sphincter. In a few moments, it would have slid completely free of my rectum and would fall into my panties. There, it might make an unsightly--and unnatural--bulge that would certainly startle my fellow travelers.

Fortunately, there was a way of out of my dilemma. I quickly clamped my buttocks together, to prevent the dildo from sliding all the way out of my ass, and sat down on the bench that the bus company had so thoughtfully provided for its waiting riders. The butt plug slid home again, the thick, bulbous end spreading my asshole wide as it was shoved upward through my lubricated anus. I breathed a sigh of relief, relaxing my ass cheeks. As soon as I got to work, I’d take go to the ladies’ room, enter a stall, and remove the butt plug until I’d wiped away the excess lubricant. Then, I’d reinsert the butt plug, with no one the wiser.

That was my plan, anyway.

“Alice! Mr. Andrews wants you to step into his office immediately,” Brenda, our receptionist, advised me the moment I walked through the door to Chambers and Chambers, Ltd.

On my way up, in the elevator, the butt plug had begun to slip again. Fortunately, I’d been alone in the car. I’d pressed my buttocks back, against the rear wall of the lift, sending the dildo home again. So far, it had remained fully lodged up my ass, but that situation could change at any moment. “I need to use the powder room first,” I told Brenda.

She frowned, shaking her head. “I wouldn’t if I were you.”

Mr. Andrews must be pissed, I thought. But why would he be mad at me? I hadn’t done anything. I supposed I could see what he wanted before excusing myself to visit the ladies’ room. “Okay, Brenda,” I replied. “Thanks.”

Mr. Andrews’ office was only fifty feet from the reception area, down a hallway to the left. I hurried as quickly as I could. Thank goodness, the butt plug didn’t slip. Please, God, I prayed, let it stay put until I can get to the ladies’ room. It felt wonderful to be stuffed with the artificial cock, and the secret that, beneath my skirt and panties, it occupied my rectum was thrilling, too, but I was beginning to wish I hadn’t come to work with a latex plug up my butt. My constant fear was that the damned thing would ease out of my rectum. What would Mr. Andrews think if he saw the outline of a dildo-shaped butt plug in the seat of my mini-skirt? What would my fellow employees think? How utterly humiliating such an experience would be!

I knocked at his door, and Mr. Andrews called, “Come in.”

I turned the doorknob and pushed against the massive, heavy door. It opened upon a burgundy carpet that led to the project manager’s massive oak desk. Between two Tiffany lamps, Mr. Andrews sat in his high-backed leather-upholstered executive’s chair, behind a laptop computer.

I felt the butt plug sliding down my rectum, slowly but surely. Horrified, I gulped, managing to keep a straight face as, again, I clenched my ass cheeks tightly together to halt the downward slide of the dildo.

Mr. Andrews glanced up at me. “Armstrong,” he said, calling me by my last name, as he referred to all his sales agents. “Step into my office. Have a seat.”

Thank God! I thought, hurrying forward. I nearly plopped into the chair opposite his own, offering him a faltering smile as I thought, I need to get to the ladies’ room right now! “Mr. Andrews, I came in right away, because--”

“I appreciate that, Armstrong.”

“But, if this can wait just a few minutes, I need--”

“Sorry. I have a busy schedule--one I need to stick to--and you’re the first item on my agenda.”

Great, I thought. At least, the butt plug had been driven home by my sitting in the chair. It was fully lodged once more in my ass, buried inside my rectum to the hilt. I needn’t worry about it sliding free as long as I was sitting on the damned thing. I nodded at Mr. Andrews. “I understand.”

“I’ll get right to the point, then,” he said. “You’ve been with the firm for only two months, but you’ve already surpassed my other associates’ sales, including those of people who’ve worked for me for twenty years.”

I smiled, flexing my anus around the butt plug. The dildo’s rigid, uncompromising presence within my ass really was comforting and reassuring. “Thank you.”

“I really don’t know how you do it, nor, of course, do my other sales agents, but I want them to know.” He paused, offering me a smile. Although Mr. Andrews was a handsome man, his smile reminded me of a shark about to feed. “I want to promote you to the company’s training manager. I want you to show the others how it’s done.”

I was blown away by his offer. I’d come into his office expecting a reprimand for I knew not what. Instead, I’d been offered a promotion. “Wow! I don’t know what to say.”

His smile broadened. “Say ‘yes,’” he suggested.

I blushed. “Yes--I mean, yes, sir.”

“Pete, from now on,” he corrected me.

“Yes, Pete,” I replied, “and thanks.”

“There’s no need for thanks,” he said. “You earned the promotion.”

I nodded.

“There’s just one other thing.”

I waited.

He hesitated. “Don’t take this the wrong way,” he cautioned, “but, as a manager, you’ll need to dress differently.”

I frowned. “Dress differently?”

“No more mini-skirts, for one thing,” he explained, “and no more cleavage.”

“If I’ve been dressing inappropriately--”

“You haven’t. Not for a sales associate. But you’re a manager now. You’ll be more in the public eye, attending seminars, representing the firm at conferences, interfacing with clients. What was appropriate dress for your cubicle won’t be suitable for an occupant of one of the corner offices.”

One of the corner offices? I thought. These coveted office spaces were reserved for executives who were expected to remain with the company until retirement. I’d made it to the top--in only two months.

I must have looked shocked, because Mr. Andrews--or, rather, Pete--chuckled. “That’s right, Alice,” he affirmed, “a corner office.”

Not only was I to receive a corner office, but I was also to be addressed as “Alice,” instead of as “Armstrong”? I shook my head.

“I trust you’re agreeable to accepting the promotion?”

“I’ll say!”

He chuckled again. “Good. Congratulations. Now, I’m sorry to be abrupt, Alice, but, as I said, my schedule today is just impossible, and--”

I rose. “I understand,” I said. The butt plug remained in place, but it was poised within the circle of my anus, ready, at any moment, to slip free. If that happened, in front of the supervisor who’d just promoted me--well, the result would be mortifying. I strode across the thick carpet, toward the door, glad for the opportunity to tend to the errant dildo. Within the last second, it had started to slide out of my impaled anus once more. As I reached the door, Mr. Andrews called, “Wait.”

I stopped, tightening my buttocks to prevent the butt plug from sliding farther down my anal passage. I turned, facing him. “Yes, sir?”

“Pete,” he reminded me.

I smiled, despite the dildo that threatened to slither out of my asshole. Clenching my ass cheeks more tightly, I nodded. “Pete, I mean.”

He held up a key on a silver chain. “The key to the executive’s restroom,” he said, tossing it to me.

In my mind, I saw myself lunging forward to catch the key and the butt plug plopping out of my ass. Fortunately, it had been a good toss, and I caught the key in midair. “Thanks,” I said.

“Enjoy your new office and the perks that come with it,” he advised.

“I will.”

“Remember, no more mini-skirts.”

“I’ll remember.”

“Okay, Alice. I’ll see you later.”

I managed not to hobble as I exited his office, closing the door behind me. I knew without having to look that Pete’s eyes would be focused on my buttocks and legs. Although he’d forbidden me from wearing mini-skirts any more, now that I was a manager, his prohibition wouldn’t prevent him from ogling my ass though the tight, brief skirt.

The butt plug continued to ease down my rectum, despite my clamped buttocks. Any moment, it would pop out and (if I were lucky) lie inside my panties (rather than dropping to the floor). The ladies’ room was on the other end of the floor. I’d never make it. If the damned thing did slide free of my anus, it wouldn’t go unnoticed. Mr. Andrews wasn’t the only man at Chambers and Chambers, Ltd., who routinely admired my ass. The butt plug eased another inch out of my sphincter. I stopped, glanced around me, and, assured that no one was in the immediate vicinity, pressed my ass against a desktop, driving the dildo back through my anus and deep into my bottom. This action would gain me a minute or so, before the butt plug began its next inexorable slide down my bowel, but I still wouldn’t have enough time to get to the ladies’ room.

But, I realized, I wouldn’t need to go to the ladies’ room. Pete had just given me a key to the executives’ restroom. The unisex lavatory was just a few yards ahead. I hurried to my destination, knocked sharply on the door, and waited for a response. When there was none, I unlocked the door, and hastened inside. A few minutes later, I exited, having allowed the butt plug to ease down my anal passage and into my waiting hand, having wiped my ass, having washed both the dildo and my hands, and having wrapped the butt plug in tissue and placed it inside my purse, where it wouldn’t have the opportunity to humiliate me by sliding out of my ass at an inopportune time, I exited the restroom and returned to Pete‘s office.

I knocked at his door.

“Come in,” he called from within.

As I opened his door, he looked up at me, and I announced, “I’m going shopping, if you don’t mind, to buy something more suitable to my new position.”

He smiled. “Good idea, Alice.”

“I’ll be back as soon as--”

“Take your time.”

I smiled. “Thanks, Pete.”

As I strode by Brenda’s work station, she gave me a sympathetic look, assuming, I supposed, that I’d been fired. I smiled at her, and she looked away. I almost laughed at her discomfort. Let her think what she wants, I told myself. She’d know the truth soon enough.

As I rode the elevator to the first floor, I took the tissue-wrapped dildo from my purse and deposited it in the nearest trash receptacle. Now that I’d been promoted to training manager, now that I’d been given a corner office and all the perks that came with it, now that I could leave the office to buy new clothes or to run other personal errands, I didn’t need the comfort and reassurance that having a butt plug shoved up my ass had provided in past days. From now on, self-confidence would provide all the comfort and reassurance I’d need.

I wouldn’t need the butt plug anymore, but, well, I was going to miss the sensation of having my ass crammed full of something long, hard, and thick. I smiled as I thought, Maybe I wouldn’t. Pete had ogled my ass since I’d first joined his team. It might be nice to have my boss on my ass, I thought--and in it. I’d see if Pete wanted to buy me a drink after work today. Once he’d seen me in the new dress I was going to buy, I didn’t think he’d demur. Over cocktails and dinner, we could discuss my sexuality--and his own. If he was okay with the fact that I was a chick with a dick. . . . Somehow, I didn’t think that would be an obstacle. As I said, Pete had ogled my ass since I’d first joined his team. Besides, the office scuttlebutt was that he’d romanced a transsexual once, a few years ago, which is why he still occupied a project manager’s chair rather than an executive vice-president’s.

Yes, I thought, grinning, I was going to enjoy all the perks of my new position, including Pete Andrews and his thick, hard cock.

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