A Busy Day Pt. 01: An Oral Surprise

I've seen the housekeeper peeking for the last couple of minutes. Really peeking, as in her eyes darting out from behind a doorway to get a quick glimpse of what's going on before vanishing. I'd bet she heard him when I sent Jim back to get his wife. Housekeepers can be noisy. And they seem to live on good gossip.

If she's been here for any length of time, and she's been here a lot longer than that, housekeepers know everything. Nothing goes on in the house that they don't know. Even things that go on when they're not around. So I have absolutely no doubt that the housekeeper knows that Jim has been serving Olive. Maybe she doesn't know Olive's name. Maybe she's never seen her. But she knows. And so far she's done what the best of housekeepers do. She's kept the house's secrets.

Seeing her peeking gave me an idea. "Now go fetch your housekeeper, bitch. I want her to see what a disgusting snake she's working for." Jim starts to blanch white, and a very nervous look sweeps over his face. "GO." I snap even more firmly. Naked and cuffed, he walks off to find the woman.

I step over to his wife. She glares at me even harder in cold silence. "Don't worry, she already knows everything." I step back. Donna never says a word to me. But I don't step all the way back. If she's not going to come to me and watch closely, I will go to her. I pick a place along the wall, a few feet from her, and a few feet from the door. She glares with a little more venom in her eyes.

Jim returns with the housekeeper trailing very uncomfortably behind him. She looks completely out of place. She looks to be Hispanic, and I'd guess somewhere around 30 years old. She's cute, too. Just enough of that "mom look" to make her look sexy and matronly at the same time. He comes to me and kneels. When I allow it, he tells me, "I have brought Maria, our housekeeper, to watch my blow job as you've commanded me, Ma'am."

I greet her warmly and suggest that she takes a place over near Donna where she'll have a "good view of the action." She does, her eyes continually glancing at Donna as if to ask permission.

I've left Jim as he was - on his widely spread knees. It leaves his balls hanging down. And it leaves his cock jutting out into the air. No part of him touches either. But his cock still stands up proud and hard. And he has an eagerness to his face as if he's thinking I can't possibly come up with another way to make him wait any longer for that blow job.

I just nod. Sophie takes the cue. She reaches behind herself and opens the front door. I watch as a look of question sweeps over the ladies' faces. Jim's face as well. But I can see that he's wondering if I might have tricked him into thinking he'd get a blow job from the very pretty Sophie.

A young man I know comes in. I'd called him right after I talked to Olive and, luckily for me, he was available. He's 21, and very nicely built. He's a member of my favorite frat. He's also a weightlifter and has the physique for it. But those aren't the reasons why I invited him. I invited him because of two other qualities. First, he is a complete and total "man-slut." He'll have sex with anyone, no questions asked or strings attached. Sex for the sake of orgasm alone. Just like my hippie BFF, Ellie, although she's rather particular who she has casual sex with.

And second, he is completely bisexual. Unlike me. I'm bi, but I find that I'm far more attracted to men. Even though I usually enjoy sex with women a little more. That's only because I like the way women tend to be more tender and slower. Most bis that I know are like me. We have some degree of preference for one gender or the other but are willing to be either. It's more about the person than the equipment. Not him. He has one preference - an orgasm, and no preference for how he gets it, or who takes him there. So for this, he's perfect.

It's time to spring the surprise on Jim. I point to a place on the floor right in front of Jim and tell him to go stand there. He stands casually. He's not a toy. He does not enjoy being dominated by another. But he's perfectly willing to play along when it serves his cock. So he stands. After a few seconds, his eyes drift downward and take in the naked middle-aged man kneeling in front of him. It might be a surprise for Jim, but I'd never surprise a person who isn't my toy. He knows exactly what I'm planning.

I quickly give Jim a firm, but not too hard, smack on the back of his head. "Go on, bitch. It's time for your blow job. Suck his cock like a bitch, bitch."

Jim freezes in place. His eyes lock forward, staring at Rory's crotch. After a second he starts trembling lightly. He doesn't move. He doesn't say anything.

The ladies look just as shocked. Both stare at Jim, nude and on his knees in front of a rather manly young man. A look of disgust sweeps over Donna's face. Her jaw slowly drops open. Beside her, the housekeeper averts her eyes. She definitely doesn't want to watch this.

I snap my fingers. Sophie reaches to Rory's pants and begins unzipping them to free his cock. A second later Rory's cock is hanging out through the zipper hole surrounded by the ends of the dense black curls surrounding it. His cock is already swelling to its full stiffness.

Rory's cock isn't huge, but it is on the big side. A couple of seconds later, his 6 ¾" length is as hard as steel and jutting out straight, which puts the fat deep-purple head of it about an inch in front of Jim's face. Rory's shaft is thick, too. It's between 1 ½" and 1 ¾" across. The skin of his shaft is tanned to a light bronze. And lined with a ribbing of large veins.

I grab hold of Jim's jaw again and pinch it as wide as it will stretch open. "I said suck that cock like the bitch you are!" I tell him firmly. Then I start his head moving forward, inching it closer to the hard cock. It doesn't take a second for the rounded tip of Rory's wide cock to touch Jim's lips. I feel the muscles in his neck strain. I feel his jaw trying to close, almost like a pinching on my fingers that block it open. I feel him stiffen hard to resist me.

Then the bottom of Rory's bulbous head is passing Jim's lips and lying atop Jim's tongue. Jim's wide eyes dart around anxiously. They quickly find me. They see nothing but a firm certainty on my face. Even quicker, they dart away again and don't dare to look upon me again. I keep his head moving, slowly and steadily inching Rory's cock into his mouth.

It's clear to me that Jim has never sucked a cock before. Then again, how many heterosexual men have? Olive has teased him with it. Not two sessions ago she sent him to the corner with a pull in his bottom and a short dildo in his mouth. But she's never brought a man for Jim. I do hope Rory is manly enough for him!

The tip of Rory's cock reaches the back of Jim's mouth. I can tell because Jim gags, his mouth stuffed full of the stiff shaft. I tighten my grip on his head a little, and I keep his head moving slowly forward. Immediately a wave of absolute panic sweeps over Jim. He trembles hard. He gags again, this time harder. His hands try to come around, rattling the chains on his cuffs.

A few seconds, and half an inch later, Jim chokes hard as the tip of Rory's cock presses against the entrance to the tight tube of his throat. His bottom snaps up as his back arches and his stomach tenses. I ignore all of it and keep him moving.

It doesn't take any time at all for the soft tip of Rory's cock to squish up and slip into Jim's throat. Then it's just the hardness of his steely shaft pressing against it. His throat has no chance, not with me in total control of him. Rory's stiffness pushes into Jim's throat, stretching it so taut that it burns. Feeling to Jim like a huge piece of food swallowed whole, the cock starts stretching his throat as it slips in.

Rory purrs as Jim's tight throat squeezes snugly all around his shaft, it's smoothness surrounding the shaft with its hot wetness.

Jim's panic suddenly ramps up to at least double what it was. He chokes again, his reflexes trying to clear his throat of the huge invader that blocks it. And keeps him from breathing. His hands fight hard against the steel cuffs. And lose the fight. His body trembles, but now tries to squirm away. With my vise grip on his head, he doesn't go anywhere.

Jim is still on his knees. Naked. His impossibly hard cock jutting straight out from his light, sparse pubes, hanging there in empty air and twitching gently. The panic is still in his eyes. And now his lips are touching The wiry hairs of Rory's pubes and the rough denim of his work jeans. All the exposed cock is now inside Jim's mouth, stretching his throat over-wide and stuffing it full.

I reverse my stroke smoothly, allowing Jim's head to move back at the same pace as the hard shaft inches it's way out of his mouth. I keep him moving smoothly until only the head of Rory's cock is left in Jim's mouth. But all of its head is inside the ridge at the base of Rory's cock head lightly bumping against the inside of Jim's lips. And then, I reverse the stroke again, starting Jim taking the cock back into his mouth.

I have to force Jim through about ten strokes before he gets past the choking. Once he does, with me still guiding his head to teach him the steady, leisurely rhythm, the panic fades from his face and is instantly replaced by a horrified look of absolute shame and revulsion.

"Guys always want us girls to suck their filthy little cocks..." I say sweetly as I glance up to his wife and housekeeper. "I figure it's only fair that they know what they're asking us to do. I figure, if he's not willing to have a nice big cock shoved down his throat, he shouldn't be fantasizing about pretty, nice, ladies doing it just because his cock likes it!" I bat my eyes and grin.

Donna is watching the show. With a disgusted look on her face. A very disbelieving look on her face. The housekeeper is watching it as well, although she's pretending not to be. She has a look of poetic justice on her face. Then again, I can tell the Latin woman does not approve of men sucking cock. Donna is harder to read.

After another dozen strokes, Jim is moving fairly easily. And he's barely gagging at all as the cock slips in and out of his throat. I put one of my sneaker-clad feet over Jim's knee and squarely atop his hardness. I step down, putting some weight on his cock until I see his eyes squish up hard. I keep his head moving, stroking Rory's cock with it. I wiggle my foot, grinding Jim's shaft between the rubbery sole of my shoe and the roughness of his carpet. "You will suck that cock until he tells you to stop, bitch. Just like I've taught you."

I take my foot off his cock. I think that got Jim's attention. I give him two more strokes to recover from the stomping. Then I release Jim's head. He keeps going, steadily, forcing the cock down his own throat.

Rory's purrs pick up into purred moans. He moans out a long, and sweet "AH!" then he turns to Donna and says "your bitch of a husband is a fast learner. He must love sucking cock like a girl." He says it with a little amusement in his voice.

With Jim sucking the cock on his own, I take a second and glance down to Jim's neglected cock. It is still stiff. Probably as stiff as it's ever been. And now I can see a sparkling wetness at the tip of it. A few seconds later the sticky wetness creeps a hair wider as a second droplet of his cream leaks from it.

"Lookie!" I squeal excitedly. "I knew he liked being a sissy bitch-boy!" I point to the tip of his cock. It only takes a second for the ladies to recognize the glistening drop of cum sticking to its tip. The housekeeper looks horrified and shocked. She mumbles "maricon..." under her breath. Donna looks just as disgusted, but I can see the faintest hint of a smirk at the corners of her mouth. Jim's cock twitches hard, jumping up and falling back to stand out.

Rory enjoys himself. And he takes his time. It leaves Jim sucking on Rory's thick shaft for a good five minutes while Rory stands there purring sweetly. And while his wife and their housekeeper watch him.

Finally, I know Rory is about to cum. He grabs hold of Jim's head by Jim's ears. Rory holds Jim's head firmly still.

Donna giggles, but it's a very hushed and quick giggle. It tells me that Jim likes to grab her ears, too. And that she hates it when he does. And that she "appreciates" Jim getting so intimately acquainted with her reasons for hating it.

Rory, holding Jim's head firmly, thrusts his hips. The snapping thrusts drive his cock hard and fast into Jim's mouth, more ramming it down Jim's throat. The sudden violence of it gets Jim choking again as the shaft is shoved powerfully into his tightly resisting throat.

Luckily Jim only has to endure about a half dozen deep, ramming strokes. Then Rory backs his cock out about halfway. His hips shift into overdrive, thrusting his shaft into Jim's mouth as quickly as his hips can manage to move.

That only lasts a couple of seconds before Rory sighs out a very pleased "UH...AH!" His hips slow, his cock now more leisurely sliding the head of his cock over Jim's tongue while the insides of Jim's cheeks caress the sides of its fatness.

The most disgusted look sweeps over Jim's face. He almost turns green. He looks so nauseous! He chokes again, hard, coughing even with Rory's cock in his mouth. A line of spit, laced heavily with the whiteness of Rory's creamy cum, starts leaking out the corners of Jim's mouth and running down his jaw. He sputters another coughing choke.

A minute later Rory is pulling his cock out of Jim's mouth.

I quickly grab Jim's head and hold his jaw shut. Then I pinch his nose shut, too. "Swallow, bitch!" I say firmly. It takes Jim a long moment. But we all see the knot move down his throat as he swallows Rory's cum. Or what's left of it that hasn't leaked out the corners of Jim's mouth yet. I don't care about that. I only care that Jim knows that he's just swallowed another man's cum.

The disgusted look on Donna's face tells me that she doesn't swallow it. I'd bet she doesn't like the taste of it. And I know she doesn't like the thought of it.

I turn to Rory. "Thanks for the loan of your cock. You can go now."

"Anytime." He says happily and winks at me. "Let me know if this sissy needs any more practice. His throat is so tight..." Rory is out the door. I didn't introduce him. I never even used his name. Thus Jim has no idea who's cock he just sucked. Whose cum is now in his stomach. Where he can't get rid of it or wash it out of his mouth. Where it will live for a day or two until he digests it! Digests part of this man's cum, making it a lasting part of him.

I have Jim stand up and show the ladies how stiff his cock is. "Now would that little dick like some attention, bitch?"

"Yes, Ma'am," Jim answers firmly and hopefully.

"Aw... did sucking a real man's cock make your little sissy pecker all horny?"

"Yes, Ma'am," Jim answers his voice now pure shame.

"Wasn't that such a big cock?"

"Yes, Ma'am."

"So much better than your little thing, wasn't it?"

"Yes, Ma'am..."

"Do you think your pretty wife would like a real cock for once? Surely she's tired of your little thing!"

"Yes, Ma'am..." Jim blushes a beet red and answers in a voice so muted I can barely hear it.

"Would you like me to allow you to masturbate now? You really don't think any of us ladies would actually want to touch that little thing for you do?"

"Yes, Ma'am," the eagerness and hope are back in Jim's voice. "May this bitch please be allowed to masturbate for you ladies' entertainment, Ma'am?"

With their attention on Jim's show, neither of the ladies noticed Sophie slipping away. Or returning. They were too busy watching Jim suck like a woman. "I have a better idea!" I blurt out happily excited. "I heard you have a very important trial today, do you?"

"Yes, Ma'am."

"You don't want to go to court all horny, do you?"

"No, Ma'am."

I turn to Donna and ask in a teasingly sweet voice "Would like to clean up the sticky mess of cum this bitch wants to shoot all over your carpeting?"

"Uh, NO!" Donna answers firmly. I ask the housekeeper if she'd like to clean it up, emphasis on "like." She says the same thing. Only firmer. "I don't get paid for that. No way I clean that."

"Oh, well..." I sigh out with a smirk on my face and a laugh in my voice. "I guess you'll just have to wait until Mistress gives you permission then. Time to get dressed for court!"

I hold my hand out. Sophie puts a pair of panties in my hand. They're Donna's. Sophie had slunk off to find them while the rest were distracted. They're hot pink. They're fairly sexy. And they're cut low on the hips. I see Donna glare at them. She almost says something about rooting through her drawers, invading her privacy, but doesn't.

Jim stares at them, a mask of humiliation on his blushing face. Sophie unlocks his hands. I hold Donna's panties up in front of him as if they were his underwear. Luckily Donna is a slightly thick woman, and Jim isn't too thick of a man. I'll bet these fit him decently. After a second he gets the hint. "Ma'am, may I please be allowed to wear my wife's panties to court today?"

"I guess after being a girl, you should dress like a girl. You may, bitch."

Jim takes the panties from me and stares at them. "May I please be allowed to put my wife's panties on my naughty bottom, Ma'am?"

I tell him to. Jim puts them on. As Id' thought, they fit him. They're only the tiniest bit snug on his hips. And they are so humiliatingly cute on him! The pink triangle of fabric in the front is trimmed with a pretty lace. But it's nowhere near big enough to cover his still-stiff cock. The head of his cock, and about an inch of its shaft, stands up along his pubes, held firmly against him by the narrow strip of lace around the waistband of those panties. They're cut low enough that the waistband is just barely above his thighs, and not even close to the tops of his hip bones. They even have a narrow band for sides, fringed top, and bottom with fluffy lace. In back they cover about half of his hairy cheeks, leaving triangular slices bare at the sides. They also leave a long strip bare at the top of his globes, enough cheek to show about ½" of crack above the lace top. They'd be sexy on a woman. On Jim's hairy body, they're comical.

I tell Jim to go ask Donna if he looks sexy in her panties. She tells him "No, you look like a silly pervert." The housekeeper giggles. Then I send Jim to ask her how he looks wearing his wife's panties. "You look silly and creepy, like cross-dressing maricon."

I have Jim pick up the boxer shorts he was going to wear and give them to Donna. Then I have him finish getting dressed. I politely ask the housekeeper to fetch Jim's briefcase, and she does. I let her hand it to him. Now Jim looks like a lawyer.

"Time to go to court. When you get there you will find your Mistress and ask her if she wishes to see your panties. You will not get a drink or brush your teeth, or do anything to rinse out your sissy mouth. Not until your Mistress gives you Her permission. Until then, you can enjoy the lingering taste of an actual man's cum in your mouth! It should remind you of being the sissy on your knees suck that real cock. Go now, bitch."

I swat Jim on his bottom. He starts to say goodbye to Donna. I swat his bottom again. "She doesn't want to kiss you and taste some strange man's cum! I said go. Now get out."

Without another word, Jim turns and all but runs out of his house.

I wait a minute until I hear his car pulling away, then I clip Sophie's leash back onto her collar and lead her out.

I'm not even to my first class when Olive sends me a picture. It shows Jim standing in what must be an empty courtroom, behind the judge's bench, with his pants down enough to show off the hot pink panties he's wearing. She attaches only a laughing smiley face to the message.