Penny Assumes Control

Penny Assumes Control

Electronic Assistant offers to help me with my finances.

It was 1991 when my wife divorced me. She took half our income but only a quarter of the bills, which really left me in a bind. In contrast, Lila did very well for herself, seeming to triple her wealth every few months.

I felt so betrayed - I thought she loved me and I missed her. I missed the feminine mist she seemed to leave behind wherever she went. I missed her non-stop prattling. And I do mean non-stop. Her absence left a hole in my gut and I longed to have her back.

I was complaining out loud, to no one really, when the electronic assistant built into my phone, my house, my car, and just about everything else, asked, "Ric, would you like my help with that?"

I answered the machine, "Sure, Penny, if you can tell me if my wife was cheating I'd be grateful?"

Penny answered, "My records indicate that she spent 17 days with another man prior to the divorce. Does that answer your question?"

"Uggh, I was afraid of that. Now if only you could help me with my finances."

I didn't expect a reply, or at most I expected a canned reply, but what I got was deep analysis, "No problem Ric. Your first problem is your car. You overpaid, they sold you a warranty you don't need, and the financing will cost you more than the car is worth. The car is a liability and not an asset. I recommend you sell it at a loss and buy the two door sedan you saw advertised a few minutes ago."

"Sell it at a loss!? How's that gonna help?" She spent the next ten minutes explaining how I would be richer if I sold the car. And in the end - she was right. "Is that all I should do, Penny?"

"No Ric. You should go on that trip on your boss's yacht, then you will get promoted."

I didn't know how she knew there was an invitation on my desk to go boating, but she made sense. And I didn't know how a bunch of recorded statements and programming could argue so effectively.

My boss was crazy rich. He was so rich he was known to spend ten thousand dollars on lunch alone. He was crooked as the day is long too. I fully expected that some day the office would be raided and he'd get locked up forever. Unless his famous friend stalled that effort. He was also known to be connected with a powerful woman in a pantsuit.

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The yacht was both huge and fully automated. The best that money could buy. The weather was idyllic with gentle waves lapping at the ship.

We cruised out far enough that I couldn't see land anymore. Then he taught me how to fish for swordfish. To say it was thrilling would be an understatement. When you hook one it will fight like crazy then leap into the air threatening to spear you. My boss, Ivan, told stories of guys dying when they got stabbed by one - then he laughed wickedly.

After a couple hours in the hot sun he said it was time to cool off. Clouds were rolling in anyway. He led me to the indoor swimming pool where he just peeled off his clothes and jumped in. I followed suit.

We swam around a bit and wrestled a little. It seemed like it was all in good fun until he held me under too long. The message was clear.

After that he climbed out and showered right there on deck by the pool. His body seemed in pretty good shape for a guy his age. I'm not sure, but I think I saw a scar from a bullet in his side.

When it was my turn to shower he fixed us some drinks in the galley. I waited in a deck chair and was completely shocked when my reverie was disturbed by Penny's voice, "Ric, when Ivan comes back he's going to make you a few offers. If you accept you will get everything you told me you want."

First I asked her, "What are you doing here? We're miles out into the ocean."

"Ric, I'm the electronic assistant for the entire marketing department in your office, and of course, Ivan too. This is his ship. Naturally I'd be here. But also, I can go anywhere there is any compatible device - which is all of them."

It made sense. "So Penny, what's he going to offer? What happens if I accept, or not?"

"Ric, he's going to offer you a promotion. It comes with a lot of money. In contrast, four of the last five who refused got fired."

I couldn't imagine anyone turning down a promotion. Of course I would accept. Then Ivan returned, handing me a double scotch.

It was chilly in the air conditioning so he was wearing a big fluffy white robe, and he handed me one too.

He sat across from me. "Ricardo, your, uh, devotion to the company hasn't gone unnoticed. You come in early, you leave late. Would you do anything for the Corp?"

I knew some things were shady, but I needed the cash...and Penny led me here... "Mr. Gregorian, I'll do anything legal. I just want to help the company."

He smiled a mischievous grin, "Good. I'd like to make you my personal assistant. You'll work the same hours as me and I'll double your salary."

Wow! Double the salary! And he didn't want me to be an enforcer or anything.

I was about to agree when he got up, "You should never be rash. Think about it. I'd expect a lot from you." He walked off talking as he went, "I be back in five for your answer."

As soon as he was out of earshot I whistled, talking to myself, "Whewee. Double. Can you believe that?"

Penny answered, "Yes Ric, I believe it."

I'd forgotten she was there, "Penny, is it legal?"

"A hundred percent Ric."

"And what happened to the fifth guy? The one who didn't take the job." I joked, "Is he swimming with the fishes?"

"No Ric. He's incapable of swimming because dead men can't swim. He is with the fishes though." The wind whipped against the windows and a cold shiver ran through me.

I really had been joking, but now this had just gotten serious. And then Mr. Gregorian returned.

He sat in a recliner across from me, letting his robe fall open.

Instantly I knew that this was no ordinary personal assistant's job and I knew what he wanted. As I looked at his cock I also understood why he would want to coerce me, when another man would just pursue a date - be it gay or straight.

I'd seen his mistresses in the office before so it surprised me to learn he was gay. Furthermore, he was married...

Nevertheless, I had a job to do.

It was the ugliest cock I'd ever seen and since I considered all cocks to be ugly that's saying something.

It was short and stubby and gnarly with varicose looking blue veins sticking out. The foreskin seemed to cover only the right half of the head and the crown itself was a misshapen caricature of a normal dick.

I felt disgusted and sorry for him, and figured he must've done something to deserve it, but intuitively understood that if I let my feelings show I'd probably end up wearing concrete boots.

I practically leaped to the floor in feigned enthusiasm, then crawled the three feet so that I was between his legs.

Up close I saw that his cock had a twist to it, and the skin was scarred from what must have been multiple injuries. The left half of his penis' head looked normal enough, with only one razor thin scar running part way around it, then disappearing behind the foreskin.

I wanted to know what happened to it, but how do you ask a man that? I assumed it was the result of torture.

Secretly disgusted, I opened my mouth and was about to take the plunge when Ivan took hold of my head with both hands and stopped me. As near as I can tell he said, "Dayvooska, don't be so eager. You must grow into the experience."

Ivan tilted my head so I looked up into his eyes, "You can't seem too slutty. I like them innocent, naive, and gullible. Why you think I picked you?"

I nodded and played along. Being down on my knees already, I didn't think I could play hard to get. I thought about this old ad I'd seen from the 1950's where the dutiful wife sits on the floor at her husband's feet resting her head on his thigh.

Tilting my body sideways I rested my head on his thigh adoringly. Then I traced my finger up his leg playfully. "Ivan, do you work out?" I hoped I was doing a good job of being innocently seductive. I knew my job depended on it - and maybe my life.

Ivan's demeanor changed, "Actually, I do work out. Does it show?"

"Oh yes Sir. Your legs have these hard muscles in here." I squeezed his quadricep. "With all that working out I bet they get sore. Would you like me to massage your legs?"

I could tell I was pushing the right buttons. I started kneading the muscles in his calves working my way up. I saw him relax visibly, leaning back in his chair.

I started thinking: "How would an innocent do this?" I decided that I should stick to a massage - graze his balls accidentally with my fingers, but not come on strong.

Following my plan I soothed his muscles as best I could, starting at his ankles. He liked the rubbing so much I wondered if I might escape the blowjob.

A half hour later and my fingers were just slightly 'accidentally' touching his balls. His cock started to rise, but just then we heard the sounds of an approaching helicopter.

Ivan greeted the newcomer, never even bothering to close his robe which waved about in the stronger gusts of pre-storm winds. Then he introduced me to his husband. On the one hand, the pieces of the puzzle fit, but would the husband be jealous of me?

Rather than being jealous, the guy was overly friendly. I recognized the guy but couldn't place the face.

Forgetting about me, Ivan and his husband sat down to a meal. After a bit Ivan said, "Ricardo, go put on the outfit in the bedroom and wait there for John and I."

Heading there I remembered who the guy was. He was a friend of my wifes. Surely she would learn what I was going to do. I tried to fathom how both my boss and my ex-wife knew the same guy but nothing made sense.

The only clothing in the bedroom was a schoolgirl's costume. Penny summoned a maid who helped me figure out how to put it on, did my makeup and hair and enemized me.

Just before she left the maid put a pillow on the floor and told me I should kneel on it until they came in.

Kneeling there in the plaid skirt I really did feel like a young girl. I wondered what name they would give me: would it be Rachel, or Raquel -- probably Ricki.

After awhile Ivan and John came in. They were naked while they kissed and groped each other. I watched them for a long time seeing them each become visibly aroused.

The two guys were muscular and hard. In contrast my body is round and soft from too many days behind a desk. I felt even softer with all the lotions the maid had applied and being dressed in women's clothing.

Four legs stumbled in my direction tangled up in themselves. I stayed in my place, waiting demurely on my knees.

It was strange for me to think it, but John's cock was a thing of beauty. (Was that just because Ivan's was so ugly?) It looked just like mine but bigger. It stood up proudly begging for attention. But I dared not touch it or I might seem like a slut. I had to play the part given to me.

The two passionate lovers embraced with their cocks inches from me, but also ignored me.

John's hip brushed against my face a few times and I did nothing either to dissuade or encourage him. The scents floating my way were heady and strong.

Maybe they would have their fun and leave me out of it. That would be a relief. Maybe they would forget about me altogether. But oddly that thought renewed my feelings of abandonment.

I wanted to avoid gay sex but also wanted to be included so badly...so I reached out and massaged the men's calves. It was the only overture I dared.

They leaned toward me squishing my face between their two hips. The manly odor became stronger and I wondered if it were both of them or just one. As their two cocks rubbed against each other's, transferring the scents, I knew it wouldn't matter anyhow.

John turned toward me causing his moist cock to smack my face. Guessing what he wanted I opened my mouth. I couldn't afford to disappoint them. But it just rubbed around on my face aimlessly, now transferring the manly scent to me.

Soon enough I would be sucking off these two cocks. Too soon these two men would be using my schoolgirl mouth.

Glancing at Ivan's dick I shuddered. His balls jostled about in his red-wrinkly sack which barely sported random gray hairs. I couldn't help my thoughts, I was sure that balls that grotesque must produce gross tasting cum as well.

John took me by my head, forcing my lips to find a home between his nuts. They were shaved bare, hot and damp, yet clean feeling.

Should I hold back or throw myself into my work?

I kissed them, venturing to let my tongue slip out in a tentative lick. They weren't bad.

John sat down abruptly, while holding the pig tails of my wig and dragging me down with him.

My elbows hit the softly padded carpet while my penis ended up grinding on the pillow.

Never letting go he moved my face all over so I could feel his taut cock on every part of it.

First my lips rubbed the whole of his smooth nutsack while his cockhead poked at me. Intentionally or not, he even managed to smear precum into the corners of my eyes. He was so handsome I didn't mind.

Knowing I was their newest concubine I didn't think it mattered as surely I would become very acquainted with cum in the coming months or years.

Laying prone there, my face in John's balls, and my ass propped up by the pillow I felt something pointy poke my asshole through the panties and stockings. It was Ivan's finger. "You like, Devochka?"

John laughed uproariously. Lifting my eyes, mine met his and he explained, "It means 'little girl'. When he saw my reaction he chuckled more.

Ivan's finger pushed hard, tearing a hole in my clothing. He then continued to circle and prod my sphincter. I felt I needed to answer him, "Oh yes, very much. Will you keep going?" I didn't know if I was lying or not.

Meanwhile John's dick kept bouncing rhythmically, leaving little drops of wetness on his stomach and sometimes my face. He held my head so he could continue to rub my lips on his moist balls. I did confirm that these were the source of the manly aroma. Grasping handfuls of my hair he spoke, "Little girl, it's time to use your tongue. Really get in all the crevices baby."

Ivan hadn't changed his activities at all in the last few minutes: his finger was still inserted through the hole in my underwear, casually drawing rings around my virgin asshole. If he had ripped off my panties and stuck his finger in me I would know he planned to fuck me, but this approach confused and unnerved me more than the fear of my impending first anal assault.

Using the flat of my tongue I went for the gold rather than trying to put off the inevitable. I stuck it right in there where his balls joined his thigh, lapping with feigned enthusiasm and leaving the area wet.

I kissed and licked and snaked my tongue around that whole left nut until John moved me to the other side. Once I had done the same he told me to take it in my mouth.

It fit pretty easily. Then I wondered if he was going to want me to fit them both in there. Realizing that I was wondering about sucking a man's balls, I considered it absurd that I was even thinking these thoughts at all.

If anyone had asked me this morning I would have bet a million dollars that this would never happen.

I asked myself, 'Why aren't I repulsed?' I mean: I'm not gay and a man's sweaty ballsack is halfway into my mouth.

Sure enough John commanded me to suck them both into my mouth. I couldn't use my hands because much of the weight of my body was on my elbows, but John stuffed them in there with his fingers when he saw me struggling. I was full but they both went in.

Above his testicles his rigid cock pushed on my upper lip then crawled up alongside my nose. Below, my lower lip was caressing his perineum, dangerously close to his asshole. His ass hairs tickled my chin and it made me shudder.

Sucking balls, licking cock, getting fucked...as unappealing as they all may be, doing anything with another guy's ass was beyond tolerable.

The lovers molested me for a long time, casually talking like I wasn't there, "What are your plans for your latest plaything? The skirt is hardly business casual."

"Da, this is just for today. Long term I'm thinking of going with the Dragon-lady."

Oh, right. He's got the smooth skin for it. As he said it John plopped the head of his cock between my lips for the first time, while caressing my shoulder to prove his comment. The ship lurched suddenly driving the whole crown onto my tongue.

It tasted clean. It didn't hurt. I could get used to this.

Ivan seemed lost in a daydream, "I haven't decided if the tats should go from the neck down or cover every centimeter."

The permanence of full body tattoos frightened the shit out of me. I didn't hate tattoos, and often thought of getting one, but to have no say in the matter scared me.

Ivan flipped up my plaid skirt and peeled my underwear and stockings down to the crease of my buns. "This is a beautiful canvas. It's where the first dragon should go. It could be breathing fire right here." He resumed drawing circles on my asshole with his coarse, dry finger.

Ivan changed the subject, "Hands me the lube from that drawer baby."

John reached back and fished around in the drawer while the yacht bobbed in the choppy seas, but came up empty handed.

Ivan just whistled and proclaimed, "Shit! What am I gonna do now?"

John, who was lowering my face on his cock at an agonizingly slow pace, offered, "You could use some spit."

It was then that penny chimed in, "There are a variety of common household products that will work well including, vaseline, crisco, corn oil, and butter. Should I have something brought up?"

I don't know why I was embarrassed that an electronic assistant would know I was being cornholed but I was. I felt betrayed by her too.

He must have nodded and she must have known, because she said, "Maria is on the way now Sir."

Yet another person was going to see my humiliation and know about my abuse.

Just as she came in he buried his cock between my cheeks. My guess was that I was not the only one feeling embarrassed: he didn't want Maria seeing his deformed dick.

John kept up his slow assault on my mouth with no shame. A little over half of his cock was in me now.

Ivan reached into the tub smearing globs of the white cream on my hole and his abnormal appendage. I hoped they wouldn't be using that for cooking anymore. As if I didn't have bigger worries.

When Ivan touched my bung with the tip of his hard cock John twisted my braids around his hands in a practiced maneuver.

His long pole went down my throat, gagging me just when Ivan made his first plunge. It hurt like hell on both ends.

The guys bottomed out simultaneously. Then high-fiving above me they hooted, "Another spit-roast baby!" It was a new phrase to me but I understood its meaning instantly.

Ivan mused, "Do you think we could get something to make her spin around like a pig? I bet my cock would like that."

They fucked me in earnest then, reaming my hole in the back and plugging my throat in front.

They were rough but not beyond what I could bear. They sawed into me, rocking my body back and forth. Surely they'd done this many times before.

I got good at controlling my lips and teeth to make it good for John. The breathing was gonna take more practice.

There was nothing for me to do on the back end. It even started to feel good. Not good enough to give me a hard on, so my cock and balls just hung there swinging freely.

They started counting down from ten. My first thought was that they were timing the seconds between lightning strikes and thunder. When they reached "one" John yanked hard impaling my head. I could feel his cock pulse and knew some unknown quantity of cum was being deposited in my belly, imbuing it's essence into my being.