Call 888-411-1230

How to Train A Secretary

by Marlissa

 

 

 

---

Dear Mistress Blog

---

Are you one of Alexa's long term clients?

Mistress Alexa believes that you should have an incredible welcome each time you call. Indeed, that you who have called over and over again, should receive treats and rewards, over and above a new caller. Which is why there is now a sliding scale price schedule, with newest clients paying most and oldest clients paying least. Check out the details on our PRICES page.

Free Audio Downloads for Men who want to be Feminized.
Some of our very favorite audio sessions began with a specific request by a client, or a fantasy session. Curious about how it works? Want to hear a little bit of what Alexa can do? Listen.

Follow me on Twitter

I follow everyone who follows me. .

Subscribe

Don’t miss a tip, trick, or theme. Subscribe to houseboys.net erotic blog RSS.

Vacations & Weekends

Planning a long weekend or business trip alone, and want to make sure you get dressed up like a sissy should? Set up weekend long Text or Audio session with Mistress Alexa tracking, texting, calling and watching your progress!

E-mail & Alexa

E-mail Alexa with your pics, comments, and stories

Quickstart

New to Feminization? New to wearing panties? Having trouble balancing on your heels? Feeling a bit naughty and need a spanking?

Practice Positioning yourself in a Female Role

Read some fiction. Find a scene in which you would like to play a part. Start here with our Erotic Stories. Or check out storysite.org. Then call Alexa with your favorite stories, lie back, and relax.

Do you like dress-up feminization sessions? Ask the Mistress to take you shopping!

Do you want to experience yourself as a woman? Ask the mistress to decorate you, from the outside in.

Pamela thought Kirk might just be at the breaking point.

And she loved it!

If he took it, great; if he quit, she'd find somebody else.

"Please make him stop, Ms. Hennessey! It hurts so much!" There were tears - real tears - in the boy's eyes, but she had no intention of stopping the fun now.

"Continue," she coldly ordered. Without delay, the large man continued to paddle Kirk's backside. Though Kirk struggled, his punisher was a good foot taller and had a solid muscular frame. He also had the incentive of earning more money in one afternoon than he did in a whole week of outcalls. Even if the action was kinky, he'd gladly play his part for the amount of money the woman had offered him.

Besides, he was enjoying it.

And so, Kirk, dressed in a woman's blouse, skirt and high heels, wriggled helplessly on the man's lap, his bare ass, now bright red with pain, fully exposed by the simple adjustment of flipping up the short skirt. Pamela for her part was revelling in a fantasy she had, until relatively recently, been unaware that she's ever wanted to indulge. Stretched out behind her desk, in her large, soundproofed office, she watched the two males in fascination, all the time fondling herself. She was almost naked, but may as well be wearing a suit of armor. Neither of her two slaves - one owned, the other merely rented for the day - were in any position to threaten her. Far from it; it was she who was directing the action.

Ironically enough, she had gotten the idea from a lesbian porno magazine - one Kristen Sternberg had inadvertently let peek out of a plain brown wrapper in the executive lounge. Everyone knew that Sternberg and Amy Wheeden were lovers, so it was only mildly a surprise. And though she wasn't in the least inclined towards other women, the notion of turning the tables amused her. Watching two women make love - no. No fun in that.

But two men?

Ah... there was a thought worth pursuing!

Particularly in conjunction with her efforts at forcing her hapless secretary into cross dressing.

Kirk had obligingly crossed her, giving her the reason to undertake the experiment. It had been another outburst over his secretarial status, ironically in reference to the Cain sexual harassment case in the paper. She HAD goaded him about, it was true.

Over the last few weeks, she had slowly begun insisting that his wardrobe more faithfully display his secretarial status. Panties were first, then other lingerie she demanded he model for her in the store.

"He's my secretary," she would blithely explain to the shocked female shop clerks as Kirk, red faced, donned some frilly peignoir she asked him to try on. Pretty stockings were next. They were always covered by her male clothing at work, but both she and Kirk were very aware of what lay just underneath. Kirky was taking to his new clothing sullenly, but without any real resistance.

She fantasized about taking it further.

Kirk had finally blown up, threatening to take action.

Pamela had laughed. "You want to sue me over sexual harassment, Kirk? That would be a laugh! Man repeatedly raped by female boss! It would be a joke."

But Kirk hadn't slunk away as she'd expected. "Well, it's true, isn't it, Ms. Hennessey? We both know it," he added, pouting like a hurt little boy.

Her stony silence to him for the rest of the day had frightened him more than one of her dressing downs. Inwardly, she was pleased to have the pretext to teach her office boy a lesson - one he'd never forget.

That evening she let him go home - he'd need his rest for the ordeal on the following day, one he couldn't suspect was coming his way. Then, following another day of curt commands, she had made the necessary call.

Summoning him into her office, she explained to him what was going to happen. "Kirk, as you know I've been very displeased with you since your impertinent comment yesterday afternoon. I've given it a lot of thought and it is clear you require an attitude adjustment of major proportions."

Kirk's blue eyes were clouding with fear as she continued.

"Because I'm not sure how you'll handle your next lesson, I've requested some assistance. His name is Arnold. Please come in, Arnold."

A tall, well-muscled man Kirk's age entered the room carrying a bag, which he placed on the table. "Ready when you say, Ma'am."

Kirk's glance darted about from the large man, to the door and than back to Hennessey.

"Good." Pamela smiled. "Now Kirk, you indicated that you needed a lesson in sexual harassment. I - with Arnold's assistance - am prepared to give you that lesson. You see, for decades, men have abused women in the workplace - made them dress provocatively, act submissively, put up with exploring hands and have even been blackmailed into performing degrading sexual acts to retain their jobs. This doesn't happen any more because women have put a stop to it.

But you can't begin to appreciate any of this because you're a male. Hence, your ill-considered comments of yesterday. Therefore you must be taught first-hand. Kirk, we're going to try a little role-playing this afternoon. Call it 'sensitivity training'. Take the bag on the table and empty it out."

She and Arnold watched impassively as he did so. He looked up in confusion. "This is all women's clothing, Ms. Hennessey."

She shook her head. "Oh, no Kirk. It is sexy secretary's clothing. And this afternoon, you are going to be hunky - and quite gay - Arnold's cute little secretary." She smirked. "You'd better get dressed-your boss is waiting."

Desperately, Kirk turned to the muscled gay hustler, mouth open to plead mercy, but the man just glared. "Do as she says - or else," he warned, pulling out a tazer from behind his back.

A brief attempt at flight was rewarded with a agonizing shock from the tazer across the back. Kirk fell to the floor, gasping for breath.

"Now get dressed," Pamela ordered. "Arnold has some tasks for you to perform."

Choking back tears, Kirk slipped off his clothes and began to dress as a woman.

---