Cock of Ages Ch. 14

Evelyn yelped, looked at me accusingly over her shoulder like I was insane, and saw the look on my face. Whatever thought it inspired she kept to herself, turned back around, and put her face down while I plundered her asshole. Then I forced her to her knees to clean up the sticky mess that clung to my cock. She vomited in a corner, called me a pervert, and stomped out. You almost couldn't notice how funny she was walking.

All in all, it was a successful night. Seven more freebies to add to my total, and at least five of them had a decent shot at getting pregnant. I didn't even make Lori perform for me that night, unless you count taking the bartender into the back and letting him fuck her doggie style, to thank him for his hospitality. After seven fucks in four hours, even I was bushed. And I still had a secretary and a secret plan to get through.

***

I took it easy the next day, making more preparations for my big evening. I had told Cromwell I needed just one more day to take care of my last assignment, and while he was feeling antsy about it, he didn't see the harm. Reports from downstream were becoming more and more ominous, it seemed. He gave me the supplies I needed without comment, merely telling me to hurry the fuck up. I thanked him and went out to Casa Nova to get ready.

I was back in the hotel room by one o'clock, and ready for the interview soon after that. We would conduct it in my room, I decided, and I procured a few props beforehand to make me look like a real businessman. At about six o'clock Lori led Miss Jennifer Miller into the sitting area of my suite and waited with her for me to appear. I was on the phone to my bookie, Milo, in the other room, trying to calm him down about how much money he now owed me.

I tried to keep it cordial, and make it sound like a business deal. In the meantime, Lori served a very nervous Jennifer some very doped-up iced tea, allowed her to inhale plenty of pheromones, and soothed her about the whole thing by mentioning how much money she could make if she got the job. I have to admit, Lori did a first-rate job of prepping her. By the time I was done, Jennifer was bound and determined to do whatever it took to get the job.

Finally, after getting the bookie calmed down, I hung up the phone and came out, all smiles and handshakes. I introduced myself and dismissed Jennifer for an hour, then sat down and began the interview.

Jennifer was winsome, if tall, a lanky babe nearly five-eight with just enough up top to give her a feminine shape. She had big sorrowful eyes that were only slightly sparkling with the prospect of changing jobs. Her voice was low and deliberate, and while I could tell she was no rocket scientist she wasn't an idiot, either.

"So, Jennifer, let's get to business," I began, clapping my hands together eagerly. I think I startled her, which was good. I wanted her a little off-balance. "I've recently invested in some property here in Tampa, and I have a few other business deals I'd like to see to fruition, once I've moved in. So I'm going to need an office and a secretary. Have to have a secretary. And you come very highly recommended."

Her eyes widened slightly.

"By whom?" she asked, clearing her throat.

"A business associate," I assured her. "Someone who knows good talent when he sees it, and someone who doesn't want a reputation for sniping his colleagues' staff, so he shall remain anonymous. But you've been with Gulf States . . ."

"Three years," she finished, swallowing. "I started out in the steno pool, and then was assigned to Mr. Lucas for six months, and in June of last year I was permanently assigned to Mr. Carter. We handle all the property claims above $50,000," she said, smugly.

"And may I ask how much you made last year?"

"I, uh, I don't usually talk about money, but . . . I made about $12,000 last year." She sounded hesitant about the figure, so I assumed that she was inflating it, probably around 10%. As it was, that kind of money was outstanding in a clerical position in 1963.

I looked aghast, and for a moment she was worried that the figure was too high. "I've blown more than that at the track in a long afternoon!" I laughed. "This position starts at . . . say, twenty five? With raises every six months or so. Oh, and full health insurance coverage, including dental."

"Dental?" she asked, still in shock over the high number. Health insurance was rarely a perquisite in the clerical field in '63, but then again most health care here was a barbaric joke. People still died of syphilis in 1963. Executives, professionals, and highly-paid union manufacturing jobs got health insurance as an incentive, but almost no one covered dental.

"You do have teeth, don't you?" I asked, amused. That won me a smile, proving my point. She looked a lot better when she smiled.

"What would I have to do?" she asked, the hook firmly set. She was comfortable at twelve. At twice that much she would be far more than comfortable.

I shrugged. "Virtually nothing," I admitted. "Oh, the odd letter, some light filing, and answering the office phone. But most of the real work will be done by attorneys and accountants. You will have to keep my schedule, but considering I'll be out of the country much of the time I don't think that will be an arduous task," I said loftily in my homemade Harvard accent. "But I will need someone in the office, more or less, every day. Oh, except for vacation – you'll get two weeks, plus two sick days a month." I swear I saw her nipples go erect through the bullet-proof monstrosity from Maidenform she wore.

"And we'll contract an answering service for after-hours, lunch breaks, and the like. Oh, and you'll get a clothing allowance – say an extra $100 a month? You'll be representing me when I'm abroad, after all, doesn't pay to dress like a . . . " I waved dismissively at what she was wearing, which was no doubt a blow to her womanly ego.

"I'm . . . very interested in this position," she said, shifting in the seat. The aphros were starting to work, as was the lure of easy money.

"I'll warn you now, I treat my employees like family – family," I repeated for emphasis. "I'm very loyal to those who work for me. If you give good service, and prove my trust in you, I am apt to be very . . . generous," I said, the first hint of suggestiveness in my voice. She missed it completely.

"Oh, yes, Lori said you were a great boss to work for," she nodded, enthusiastically. "She told me about the shopping spree you sent her on, and dinner last night, and . . . well, lots of stuff!"

"Exactly," I nodded. "I like to keep my people happy . . . when they keep me happy. A sound business principal, no?"

"Uh, of course!" she agreed, nodding vigorously. I thought there was a glimmer of recognition, somewhere far back in her head, as the aphros turned up the heat in her loins. "But, Mr. Winthrop, you haven't even asked me how fast I type," she noted. "Or which system of shorthand I use."

"Anyone can type," I dismissed. "And shorthand . . . I don't give a rat's ass which one you use. I'm far more interested in your . . . other . . . skills," I said, as deliberately as possible. I fixed her with a long, serious stare.

Bingo. The light went on.

"You don't mean my, um, my filing, I take it," she said, meekly.

"Not particularly, no," I said, matching her tone. "My secretary will be sharing all of my secrets, Jennifer. ALL of my secrets. I have to know I can trust my people . . . utterly. And the easiest way to ensure that, I've found, is to make certain I am keeping a secret for my people." I leaned forward expectantly towards her. She hadn't grabbed her purse, yet, which was a good sign, but neither was she cooperating as well as I would have liked.

"Um, Mr. Winthrop, sir, I . . . I'm a good girl," she burst out. "I mean, I know that sometimes you have to . . . do things for your job . . ."

"Exactly," I said, nodding. "Very discrete things," I added.

"Right. Well, I, uh, I haven't done anything like that—"

Oh God, was she a virgin? I asked myself. That would change the dynamic significantly.

"—since I was in the steno pool," she whispered.

"Tell me about it," I said, leaning a little closer – and breathing a sigh of relief. I hadn't prepared for a virgin.

"Oh, God, do I have to?" she whimpered. I nodded. "Consider it part of your qualifications," I said, knowingly. Thankfully, the whole concept of sexual harassment in the workplace was a decade or two away. Gotta love the Sixties.

She swallowed, and looked away. "Okay, here it goes," she said to herself. "When I first came to Gulf Coast, I was in the steno pool, where all the new girls start out. It was pretty easy, really, just transcribing letters and taking dictation and typing. Every now and then one of the real secretaries would go out on vacation or maternity leave or something, and one of us girls would be dispatched to substitute for her until she came back.

"Well, the first time that happened to me I was sent to the small satellite office over in Clearwater. Only two agents over there, and one was almost always out on sales calls while the other stayed at the office and wrote policies. It was just them and me," she said, shamefully blushing.

"Go on," I coaxed.

"I . . . I did everything they asked and I thought that I was doing a good job the first day or so. Then late Tuesday afternoon, Mr. Haney – he was on office duty that day – locked the door at four-thirty and asked me to come to his office. I thought he just wanted to dictate a letter, but when I came in . . . he had his pants off." Jennifer looked mortified, and couldn't look me in the eye.

"Continue," I urged.

"I didn't know what to do – there he was, sitting in his chair with his . . . thing sticking up. I couldn't say anything. I couldn't move. I should have screamed or something, I suppose, but . . ."

"He was your superior," I supplied.

"Exactly. He was my boss. One call from him back to my supervisor, and I'd be out on the street. So I asked him, 'what is going on?' and he just looked at me . . . he looked at me like I was stupid or something."

"Had you never seen a man's penis before?" I asked, matter-of-factly.

"N-no—yes," she admitted, her face a sheet of scarlet. "I . . . there was this boy in high school, and he was going into the Army, and . . ."

"Say no more," I said, sparing her revealing the details of the loss of her virginity. For now. "Just tell me what happened in Clearwater. What did Mister . . ."

"Mr. Haney," she supplied, helpfully. "He just told me that part of the duties of the branch secretary included . . . entertainment of the agents," she said, venturing a bit of a wry chuckle. "I asked him what sort of entertainment, and he looked at me like I was stupid again. Then he told me that no secretary ever got out of the steno pool without 'proving' herself. I—I tried to keep calm, but he lost patience and pulled me over to him, and then pushed me down. On my knees. In front of him," she whispered.

"And . . .?"

"And . . . I entertained him. With my . . . with my mouth. I put his thing in my mouth."

"You became . . . a cocksucker, I believe the term is," I suggested.

"I—no—y-yesss," she hissed, finally, a tear leaking from her eye. "I . . . sucked his thing. Until he . . . went, in my mouth. He made me swallow it!" she revealed, shamefully. "He pushed my head up and down and when he did his business, he told me that all the senior secretaries swallowed. So I did. I didn't want to be in the steno pool forever – this was my big chance."

"You were right to be so far sighted," I agreed, gravely. Her nipples were poking out magnificently. Her breathing was deep and measured, and her eyes were just a bit dilated. Between the aphros and the tale of her shame, she was getting horny as hell. "Was that the sum total of that kind of experience?"

"Uh, no, no it wasn't," she admitted. "The next day I almost didn't come to work, but I did. I was late, but Mr. Haney didn't say anything. It was raining that day, and Mr. Stewart was there with Mr. Haney, so I thought I would be okay. He wouldn't try anything with Mr. Stewart right there, and besides, they were in a meeting writing a policy all day. But about four o'clock Mr. Haney told me to lock up early, because it was 'hump day'. I thought he was being crude, but I knew some of the satellite offices have looser rules than the main branch.

"So I locked up. That's when Mr. Stewart told me to join them in his office, the big one in the back. I asked him why, and he just said that it was hump day. So I went back, trying to figure out what 'hump day' meant.

"Well, when I got back there, both agents were looking at me . . . expectantly. They had a bottle of bourbon out, and both were drinking it out of coffee cups – which is expressly against Company policy!" she said, a trifle shrill-ly. "But they were drinking, and they asked me if I knew what day it was. I said 'hump day', and they asked me if I knew what that meant. I said I didn't, and that's when they told me that every Wednesday they got to . . . hump the secretary. It was tradition, they said. I guess I looked a little shocked. Who wouldn't be?"

"So . . . what did you do?"

"I . . . they asked me to show them my underthings," she said, her voice wavering, now. "My panties. I almost didn't – I wasn't raised that way, you understand Mr. Winthrop. My family may not have been affluent, but . . . well, we weren't trash, either. My mother always taught me that . . . good girls wait for, for marriage," she choked out. "But . . . well, I knew, Mr. Winthrop, I knew that if I didn't . . . 'play ball', that they might not even let me go back to the steno pool. I had to, you understand, Mr. Winthrop. I had to. I had no other choice."

"It must have been very hard for you," I said sympathetically, putting my hand on her knee. "That first time," I added. She didn't contradict me.

The idea that every cute young secretary was being used for sex back here in the dark ages might seem naïve – but historical research indicates that it happened a LOT more than most people suspected. While rape was, of course, still on the books as a serious crime, acquaintance rape, date rape, workplace rape, and the like were considered more of a legal gray area. This was the Golden Age of the executive, when white men enjoyed the perks of power, and those perks often included bagging all the young stuff in the office. I could get used to that. Jennifer's story seemed to support this conclusion, and despite the fact that I was sporting a raging boner, now, I wanted her to continue. Besides, she was clearly getting worked up, too.

"It was," she agreed, tearfully. "They had me raise my skirt and show them my, my privates, and then they took off my panties. Didn't even ask, just took them right off me and left me exposed to God and everyone. Then . . . then they had me sit on the desk, the big desk, and they looked at me, y'know, down there, and put their fingers inside me. They accused me of being a slut because I didn't have a maidenhead. A slut! Me! I had only been with one man before then, and . . . well, they kept putting their fingers in me, really fast, and something came over me, something like a fit. I think I might have fainted. Whatever happened, when they put their . . . things in me, I didn't even try to fight. Not really. I let them, like I was stupid or something."

"Did they squirt their semen into you?" I asked, trying to sound clinical about it.

"N-no, I was spared that, at least. I know where babies come from. They pulled out and squirted on my belly," she admitted. "That time. The next . . . 'hump day', they made me kneel and . . . take it in my mouth again." The thought was clearly humiliating to her, I could tell. It also aroused her, which I could also tell. She continued without prompting, "And then the next day I came in and they acted like nothing had happened. Nothing! Until lunch time.

"I brought my lunch that day, and was going to eat at my desk, but then Mr. Stewart brought me in his office and I had to put his thing in my mouth again. That happened every day, after that, the whole two weeks I was there. Whomever was tending the office that day, I had to service them at lunch. And if the other agent came in at four, like they often did, then the agent on duty watched the desk while I had to service the other agent."

"What happened after the assignment?" I asked.

"I got promoted. That was when I was made Mr. Lucas' secretary. He's in claims. He didn't touch me, he's a kindly old gent, but he had this claims adjuster who would get me in the supply room and put his hands under my skirt. He just laughed when I protested. And now, with Mr. Carter, he . . . well, he was fine until the Christmas party a few months ago. Then he caught me going downstairs for more ice, and he pulled me into the mimeograph room. That place always makes me woozy, and I had already had a smart eggnog. So I didn't struggle much when he . . . took me. But that was special, I guess, he was drunk. After that, he just looks embarrassed, although he did grab my breast a few weeks ago."

"So, you know your way around the business," I said, matter-of-factly. "Hate to tell you this, Jennifer, but that is how the business world works. The only difference with working for me is that you know up front that that's how it's going to be. And I am very, very discrete. But please understand that a man of my means has the resources to enjoy a number of pleasures, and a secretary who fucks him is one of them." She gasped a little at the f-word, but her nipples didn't fail. "I expect sex from my employees, if I want. Good sex, too. And very, very discreet."

"L-lori has sex with you?" she asked, doubtfully.

"On demand," I agreed. "Any time I want. And she makes . . . well, significantly more than a steno girl at Gulf Coast. So I want you to think very carefully about this: I want to 'interview' you and assess your skills. Your bedroom skills. And if I'm happy with them, then we'll proceed. If I'm disappointed in either your attitude or your performance, well, there are a lot of pretty girls in this town who can type and would leap at a job like this. You come recommended."

She thought about it, I give her credit for that. She thought for the better part of a minute before she sighed and closed her tear-stained eyes and nodded.

"I'll do it," she sniffed.

"Do what, Jennifer?" I asked, toying with her.

"I'll . . . have sex with you."

I unzipped my slacks and let my hard as stone cock out. "Let's get started then," I said, evenly, and nodded toward my cock.

Her eyes were wide. "I've never . . . I didn't . . . I didn't know they got that big," she whispered.

"Family inheritance," I said, dismissively. "Now show me what you can do, Jennifer. With your mouth." She nodded, walked around the coffee table, and sat slowly on her knees in front of me. She didn't look me in the eye at all, just grabbed my dick gingerly and stooped to put it between her lips.

She was a mediocre fellatrix at best, but the kinkiness of the situation made it pretty erotic. I let her slobber on my bone for ten minutes or so, making plenty of noise (which embarrassed her greatly) and called her all sorts of nasty names while she did so. She leaked a tear or two, but soon got into it. Great things, those little aphrodisiacs.

Finally, I pulled her standing again, then raised her demure skirt to reveal her very unattractive panties. Paneled cotton, as romantic as an army tent. I pulled them down perfunctorily and examined her twat. It had plenty of fur, of course, a slightly darker shade than her hair, and it grew across her thighs and up to her navel. While I'm not a fetishist about hair I can appreciate a healthy bush. I ran my fingers through her curls a few times, eliciting an accidental moan, and then pushed two of them into her pussy. She almost fainted when I did – she was soaked. I finger banged her for a few moments until she started to sway, and just as she began to abandon herself to the feeling I pulled out abruptly and found her clitoris. When my finger hit that sensitive little bud, her knees nearly gave out. I grinned at the wide-eyed response, and then turned her around.