What Now, Sir? Ch. 02

Yes, I know. I've been the silent partner so far in this escapade. An ex-girlfriend used to call me Mr. T, because she said I was such a tease, so let that be my moniker for now.

I'm in my early thirties, an average guy in looks, with perhaps a bit of a baby face, or so some have said. I stay in shape and women generally find me attractive, particularly the older ones.

And I do enjoy older women (40's to 50's usually). Why? Well, for starters, the fact that they find me attractive certainly makes the dating easier, more relaxed, and I must say, ultimately more fun and rewarding. I don't have to work very hard. Maybe I'm just lazy.

I also appreciate that they generally know what they like, are less sexually inhibited, and quite eager to please a younger guy. I suppose they want to show me the advantage of experience over a tight young body. I'm in complete agreement, though I prefer not to let on. I find it keeps them motivated.

I also like the older ones, because they seem to like big dicks, which is a pretty fair description of my equipment. Don't get me wrong. I'm not cocky about having a large penis. In fact, more often than not, a big one can be more of a curse than a blessing. Young women are nervous when they pull it out of my briefs, which usually dampens my enthusiasm.

I knew I was an oddity in high school. When I showered after gym class the comparison was unavoidable. I felt self-conscious then, but have learned to just accept myself. It's not like anyone ever called me out on it, lest someone else think they were gay, staring at my huge schlong. But, I don't doubt there was some talk behind my back.

Enough about that. So what do you think about my date tonight? A real live wire, eh?

I meet women in a lot of places, but found Barbara ("Call me Barb, honey!") in a typical location, a singles bar. In my neighborhood, there are three bars famous as haunts of older singles. We refer to this grouping as the "Viagra Triangle". Clever name, eh?

Well, Barbara and I hooked up one Friday evening in one of these. She was out with a girlfriend, I sat next to her at the bar, blah, blah, blah. You know the story.

Actually, nothing sexual happened. A lot of flirtatious remarks, double entendres, and what not. I knew she was very interested. She touched my arm, thigh, shoulder, back at every opportunity. I thought she was sexy in her own way, but decided to play it cool, took her phone number, and headed home after a couple hours. Tough week at work.

I did call her the next day, we met, took in a movie. Other than Barbara resting her hand quite close to my privates, and whispering very lewd comments in my ear during a few scenes, we behaved very civilized. I was attentive, polite, but still maintained some emotional distance.

I sensed Barbara's increasing need for approval. I must confess that control and power I feel from that neediness is quite the aphrodisiac for me. She seemed thrilled when I invited her to dinner at my house the next evening.

I assumed I was going to fuck her once we were together in the privacy of my home, but even I was taken aback at her thinly veiled seduction when she arrived.

For starters, that outfit! The dress was scandalous. This fifty something year-old tart was in a tight, very short, knit dress, such as a young woman would wear to the clubs. The bottom hem barely made it past her ass cheeks, which incidentally, looked like a couple of volley balls.

Barbara is fat. Let's not mince words. Fortunately, I'm a guy who appreciates a little extra baggage on a woman, provided it is distributed to the right places. Barb's aforementioned large booty and huge hangers up top made an enticing combination on this chubby cougar.

As Barb minced around in her 5 inch classic pointy toed stiletto pumps, I had to marvel at the lengths these middle-aged sluts went to increase their attractiveness. Taking every possible opportunity to model her physical assets, bending over to examine a houseplant, feigning a fascination with the leaves, Barb made sure I had ample time to take in that impossibly large and round ass stretching her slutty dress to the absolute limit.

The big buxom blonde certainly had a practiced routine worked out. As she strutted around the living room on my hardwood floors, the staccato sound of her heels was having the desired effect on my libido. It took great restraint on my part to not give this wanton whore the pleasure she obviously craved.

As Barb teetered a bit on her ridiculous footwear, probably from her copious wine consumption, I suggested she join me on the couch. She readily agreed as this was her objective, after all.

After some preliminary kisses, Barb soon had her hand on my thigh, then on my rapidly inflating penis. Quickly agreeing to her boss/secretary sex roleplay scenario, I soon had the overripe slut going through her paces. After dropping to her knees to remove my huge appendage from its tight confines, my top-heavy assistant began flaunting her charms, at my direction. Strutting around my living room in those too high stiletto heels, the main effect was to create an obscene amount of jiggle in Barb's tits and ass.

Once the dress came off, it was apparent that I had underestimated the size of that huge bottom. Amazing how an ass so big could be so round and shapely. Not generally impulsive, I had to spank those fat buttocks. Can you blame me? Let's resume our story. This should be a fun evening.

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Smack! Smack! Smack! "Oh Sir!," cried out the big blonde.

Smack! Smack! Smack! "Please, Sir! That stings!," moaned the heavy hootered assistant.

"Keep that ass up. Grab your ankles," he calmly responded. "This is a routine exercise I do with all new secretaries. This will reveal your ability to take direction as well as your oral, ahh, verbal skills, under duress."

"Very well, sir. I understand now. I want to cooperate fully. I just don't know if I can balance like this. May I remove my pumps?"

"Out of the question," he replied. "You must be in proper office attire."

"Yes, sir."

The big, buxom cougar slowly bent over enough to grasp her ankles. Fortunately, her giant bubble butt was balanced by her heavy hangers in front, which were in danger of escaping the miniscule shelf bra she had selected, her ridiculous pointy-toed stiletto pumps acting as the fulcrom in her obscene balancing pose. Silently cursing herself for wearing her highest heels, the pseudo-secretary waited for the next blow.

Smack! "Ohh!" Smack! "Ohh!"

Slowly walking around the volupuous woman, he carefully took in the scene before him.

"Just a few observations, Ms. Buxton."

"Ms. Buxton?"

"Yes. That is your name, isn't it?"

She smiled. "Oh yes, Buxton, of course," she said quickly.

He continued. "As I was saying, Ms. Buxom, err, Ms. Buxton. This pose is particularly seductive. Your legs, though thick, are quite muscular. Those shoes really define your muscular legs, though I'm sure that was your intent. It's obvious that you didn't choose those shoes for comfort. I think you might be trying to seduce your superior, Ms. Buxton. Are you trying to seduce me?"

"Sir, I was just trying to ..."

Smack! "Oww!" Smack, smack, smack! "Ohh!"

The big blonde concentrated on maintaining her balance under the repeated spanking delivered by his large hand with increased intensity.

Her heavy breasts were on the verge of escaping from the tight confines of her custom bra. She knew it was only a matter of time before the large drooping teardrop shaped masses would be hanging in her face. She never expected the roleplay to transpire like this.

"Here's another observation, Ms. Buxom, err, Buxton. You have the most unusual areola, can't say I've seen any so large and dark. They're easily the size of saucers. Very attractive reddish brown. They cover almost the entire fronts of your breasts, don't they? Can't see the nipples. Despite that tiny little bra you're wearing. Surely you didn't expect that scrap of material to either support or cover those giant udders. I think maybe you wanted me a see your big breasts. Maybe you are trying to seduce your boss. Was that your intent when you dressed this morning, Ms. Buxom?"

"Buxton, sir. I, ah, I just want to do a good job for you, sir, ah, to please you."

"Yes, of course," came the curt reply. "Now, let's test your verbal accuity, Ms. Buxom."

"Buxton, sir. Ready."

Holding her pose for so long, Barbara's leg muscles were beginning to ache, but she did her best to comply, hoping the payoff would be a wild ride on that incredibly thick appendage she briefly fondled earlier in the evening.

Smack! "Oh!"

"Describe what I'm doing, Ms. Buxom."

"You're spanking me, sir."

Smack! Smack! "Oww!"

"More descriptive, Ms. Buxom. Try again."

"Your spanking my bottom, sir."

Smack! Smack! Smack! "Ouch!"

"Sir, you're spanking my big bubble butt!"

Smack! Smack! Smack! "Ouch!"

"Ms. Buxom. I'm disappointed."

"Sir, you're spanking my big slutty bubble butt!"

Smack!! Smack!! SMACK!!

"Please, sir. I'm getting so wet."

Pausing from his activity for moment, her date examined the two huge meaty hemispheres, which glowed bright red.

"Ms. Buxom, spread your legs."

"Please, sir. I just don't know...," whined the big busty blonde.

"Spread."

Carefully, the overdeveloped assistant attempted to spread her stiletto clad feet without losing her grip on her ankles. Expecting her huge udders to escape their confines and plop onto her face at any moment, Barbara managed to spread her feet close to three apart. Her aching leg muscles grew more taut with her movement, while her enormous buttocks raised to an even higher profile.

Leaning over to closely examine Barbara's enormous deriere, her date was fascinated. Rick whistled, thinking, "This is the hairiest cunt I have ever seen." His oversexed assistant was showing obvious signs of arousal. Her thick dark mat of dark reddish brown pubic hair was saturated with juices and literally dripping. Some of the moisture coated the insides of her thick thighs, while an increasing amount was dripping onto the floor in a small puddle between her feet.

In his excitement, the slut's date began probing her hair covered vagina, first finding the opening by worming in one thick finger. Sliding his digit slowly in and out of her warm wet cunt, finding little resistance, then adding one, then two additional fingers the wanton whore's response was immediate and loud.

Rick was amazed. "I've got three fingers in there and this whore is loving it," he thought.

Spurred on by the moaning of the voluptuous cougar, Rick slid a fourth finger into her cunt, then curling over his thumb, began to pump his hand in and out with more vigor, never pushing his hand in completely, but stopping at his knuckles. Her copious juices increased with this action, completely coating his hand and splashing onto his arm, her thighs, and his hardwood floor.

The ardor of the overripe middle-aged slut was out of control. Shaking her head from side, she attempted to meet her date's probing hand by bouncing her big beachball butt up and down, desperately trying to get more penetration, to swallow his hand. Her vigorous hand fucking and gravity finally forced her oversized udders from the confines of her miniscule bra.

Denying his date the pleasure of a good fist fucking, Rick continued fucking her with his hand, but never sliding past his knuckles. He was enjoying the filthy pleading of his wanton whore. Her imploring was muffled by the fat fleshy bags bouncing around in her face. Her enormous bell shaped udders, capped by dark pebbly areola, jiggled continuously. The wet slapping of Barbara's boobs, combining with the squelching sounds of the finger fucking and the lewd demands of the wanton cougar, combined to elevate Rick's sexual tension past the breaking point.

Abruptly stopping his finger fucking of the rapturous woman, Rick wiped the juices and foamy froth from his hand and forearm onto the hussey's fat buttocks, giving the still red globes a shiny sheen which further increased their size and spherical appearance.

"There now, Ms. Buxom. I think that went rather well, don't you? You may stand now," her date/boss said in a clipped businesslike manner.

The overweight bottle blonde slut groaned with chagrin. She was so close to having one of the biggest orgasms of her life. She remained bent over with her legs spread.

"Please just a little more of the exercise. Surely you haven't tested my oral, ahh, I mean verbal skills enough. I want to impress you. I know I can do better."

"Now, now, Ms. Buxom. You will have ample opportunity to impress me with both your oral and verbal skills in this next exercise. Enough dilly dallying. Stand up straight."

With a sigh of resignation, Barbara straightened her body. The relief her aching leg muscles received was outweighed by the aching of her fat sloppy hairy pussy, so close, yet so far from nirvana.

"My, my, Ms. Buxom. It appears that your frilly little bra is no longer doing its job. We may need to find you something a bit more supportive. I'll think on this problem for a while. I have some excellent resources. I dare say, you are not the first top-heavy assistant to work for me.

Without looking down, Barbara understood his comment. Her too tiny bra was completely hidden behind her humongous hooters, their size and heft having increased throughout her life. Their weight and sag made the bottom portions of her bosoms expand, seeming to stretch the already impossibly large areolae to the size of medium sized pancakes, maybe 8 inches across.

During one drunken night of amorous activity, her date, a nice, handsome young man with a less than average penis, actually made the breakfast food comparison as he played with her huge sacks. In a bit of giddy playfulness, and not anticipating any mindblowing coitus, the overweight cougar, suggested that he fetch some maple syrup from the pantry, which he did posthaste.

After mounting her date's small penis, Barbara proceeded to pour most of the contents of the syrup bottle onto her giant protuberances and suggested that her young man "have at them," which he did with gusto. He must have quite the sweet tooth, she remembered thinking, because no man up to that point had ever licked and sucked her tits with such abandon.

Eventually, Barbara had a nice little cum, due to her date's enthusiastic tit-sucking. He also managed to squirt a surprising amount of semen into her despite his little cock making little contact with the walls of her cavernous vagina. She attributed this to the warm wet environs between her legs, the highly stimulating sight of her huge sacks swinging and bouncing in his face, and her highly erotic, lewd, and loud insistent pleas.

"As I was saying, Ms. Buxom, and what an appropriate name may I say, for a woman of your...ahh...development."

"My name is Buxton, sir, not Buxom," his play secretary interrupted.

"Ahem, be that as it may, quite appropriate. As I was saying, there have been a succession of well-endowed women sharing this office with me, not simply a happy accident, I might add, but you may have achieved top billing. A few careful measurements later will confirm, of course, but so far I am impressed. Very impressed."

Barbara thought the roleplaying have gone far enough. "When is he going to get to some good old-fashioned fucking?" she wondered. "And at what point did he put his penis away?"

"They're almost like little handles, aren't they?"

"Huh?" Her thoughts interrupted again.

Her date pointed at her nipples, which were still very erect and almost pointing at the ground. Slightly more than 1 1/2 inches in length and very thick, they would have been freakishly large on most other females. Centered in her huge areolae, they seemed in scale.

Barbara decided to get the ball rolling again. Rick was becoming a little too observational and docile for her taste.

"Oh, sir. These? Yes, I suppose they are a bit like little handles." she said as she lightly squeezed and tugged at the fat knobs. "Here, sir. You try."

Rick smiled sheepishly and said, "Me? Oh, I don't really think I should."

Barbara was getting a little confused, as well as sexually frustrated. "Where is this roleplay going?" she wondered, "and where is the dominant man who was spanking my fat ass just a while ago. Is he losing interest already? Maybe he really thinks I'm too fat...or old. Oh, damn."

Pleading now, Barbara said, "Please, sir. Just try it." Grasping his hands, she pulled them to her jutting prominences. "Start gently, then increase the pressure."

To further encourage him, Barbara placed her hands under her oversized bosoms, lifting them so the fat nipples were pointing directly at her playmate. This seemed to have the desired effect, as Rick began to handle her big teats more roughly. Observing his flushing face and shallower breathing, Barbara realized this was all part of his game. He pleasured in her pleading and insecurity. "Well, I'll give him what he wants, and maybe I'll soon get what I want."

Moaning loudly with desire now, the oversexed cougar began spouting out a littany of indecent requests, trying to further inflame her date's passion.

"That's it, sir. Pull on my big teats. Be as rough as you need to be. You're the boss, I'm the big-titted secretary. Show me who's the boss. Milk your big fucking cow, sir. I'm your office whore, sir. Spank my huge nipples, sir. I'm holding out my big udders for their punishment, sir. Big, naughty udders. Spank'em, sir!"

Rick had dated some shameless hussies before, actually preferring them, but this bitch was something else. Her foul-mouthed sexual demands and coarse language were exciting him to no end.

His fat dick was on the verge of bursting from his trousers, and he needed to get relief soon.

The lusty harlot seemed to be in ectasy as her play boss abused her, squeezing, tugging, slapping the dark rough pebbly areolae and long fat nipples. Her excitement only seemed to increase, getting louder and more profane by the minute as she continued to hold up her enormous boobs, squeezing them together to form a long line of cleavage, all for her date's visual delight.

Abruptly, Rick ceased his tit play.

"Well, Ms. Buxom. I thought that went quite well, don't you? Now, you may want to get a bottle of water from the refrigerator before beginning this next part of your secretarial orientation."

Confused, Barbara began "Buxton, sir, but I'm not really thirsty. Maybe some more wine..."

"Now, Ms. Buxom, we don't drink alcohol during working hours. Water. Come on, chop, chop. I'll be waiting here for you."

"Should've suggested the prostitute/john roleplay scenario," Barbara thought as she walked toward the kitchen. "This is getting a little drawn out. I wonder what he has in mind now."

Cognizant of her play boss staring at her big arse as she walked toward the kitchen, the fat cougar made sure to put extra strut into her walk, swaying her huge bubble butt from side to side, mincing in her over the top stilettos. "We'll see who blinks first," she decided.

After removing her useless bra in the kitchen, and taking a couple of swigs from her water bottle, the middle-aged floozy returned to her date in the living room, making sure to put extra jiggle in her juggs.

"Ok, Ms. Buxom. I know you have had numerous secretarial positions in the past. I have read your employment history and contacted former employers. Curious. So many employers, yet almost universal glowing reviews from those said employers. What am I missing here?"

"Well, sir, sometimes there were extenuating circumstances, certain misunderstandings about parts of my job description, which required a change of bosses or companies. But I assure you, all of my managers have been extremely satisfied with my job performance. The gratification of my superiors has always been job one in my book."