Much Deviltry Afoot

Nov 17, 2021

Much Deviltry Afoot

Preface: This is a story about two women. One of them, very strong, and dominant. The other...soon to be. This story is fictitious, any similarities to real people are purely coincidental. All characters in this story are of legal age.

It was 7:55 am, a beautiful spring morning on Long Island. My shift would start shortly and we were waiting to clock in. The director of my machinist operations, John A, came over to the clock area and greeted the crew.

He shook my hand and said, "Dave could I please see you in my office for a moment? I have an offer for you."

Who knew that this offer would change my life drastically.

"Sure, be right there."

He told me that he wanted me to go to a convention in Aruba to evaluate a new lathe for use in the CNC machining department. "I chose you because you have sixteen years of experience working as a machinist. Nobody else in the company knows the product and machines as well as you do."

I'm not one to look a gift horse in the mouth, so I immediately accepted. An all-expense-paid week in Aruba....sweet. I received an itinerary of the machine demonstrations. Hot stuff, two of the events were being hosted by female machinists/instructors from our company. There are six female machinists in our company. Female machinists are a rarity, as machine work is typically male-dominated. Most people don't know or have forgotten that during WW2, 95% of the machinist force were women...Rosey the Riveter, et al. Takes a strong woman to make it to the top in a male-dominated occupation.

One of these instructors was Marlena, a very well-spoken, fifty-five-year-old pattern maker that didn't look her age. A tall gal with legs that went on for miles. She was self-confident, intelligent, and very well-read. In my book, that spells sexy. She had a certain je ne sais quoi that made my dick hard just from talking to her. She exuded sensuality. Little did I know that she secretly had the hots for me. I would soon find out how hot.

The other instructor was a past lover of mine, Sienna. She was thirty-five years old and very pretty. She was brilliant when it came to lathes and milling equipment and was very well respected by everyone in the machine shops. She was a strong confident instructor/leader, yet oddly, a very quiet, almost mousey person outside of work. Unfortunately, the lass was sadly lacking in self-confidence in the bedroom.

I'm a male, a 40-year-old tool and die maker. I take drawings from the engineering department and use them to make and evaluate prototypes for CNC lathe tooling. You know, a big shot..a legend in my own mind.

I went over to Marlena's department and sought her out. She was operating an old Leblond lathe so I waited for her to finish before calling out to her...safety first.

We chatted about the upcoming convention, what the hotel was like, dinner, nightlife, all of the new machines to be exhibited, etc...

She told me that she and Sienna had adjoining penthouse rooms that overlook the ocean. Sweet! I told her that my room was one floor below.

A woman wears a certain look when she's on the prowl. She was giving me that look, "You know, you might not be spending too much time in your room...."

I was genuinely surprised. "You know, I think that we should have dinner one night and get to know each other a little better?" Boy did that sound corny.

She smiled at me again, "Are you trying to seduce me?"

"You're darn tootin, Rabbit!", I said in my best Yosemite Sam voice. (Bugs Bunny reference for all you late millennials and gen Z)

She laughed, "Good. Remember, this rabbit loves a nice firm carrot, so make sure to bring yours." She laughed again as my jaw hit the floor and my eyes bugged out of my head. I like a woman that knows what she wants and isn't afraid to take it. This one doesn't play silly head games.

A week in Aruba with a hot cougar....even sweeter. I owe you one John A.

The work week went by and on Friday we decided to Uber it to a quiet Japanese restaurant for dinner. The hot Sake was flowing like water, the udon noodles were hot and chewy, and the broth was spicy, much like Marlena. I found out that Sake makes her very horny. Guess who's going Sake hunting when he gets to Aruba? We spoke as though we'd known each other for years. The easy conversation varied from sports to religion, lathes, and eventually, to sex.

We were surprised to find that we're both Atheists, that sort of explains why neither one of us is judgemental. Funny how the most judgemental people are the ones whose big book says, "Judge not". I guess they missed that Sunday school lesson.

Forgive me, I digress.

We got to talking about our likes and dislikes regarding bedroom fun. She told me that while a big cock is nice, it isn't everything. She's had boring lovers with nine inches. Guys that just climbed on and humped till they came...ok done. She's had wild men with six inches that did everything they could to please her and succeeded in doing so. She said that guys with average size cocks had more to prove and always made the extra effort for her.

Having just six myself, I was happy to hear that. Who am I kidding, bigger is better. You'll have to read on to find out how I came to that revelation.

I told her that I fit into the second category. I will do almost anything to please my lady, and I'll let her do almost anything to me. I draw the line at scat. Don't leave me with a Cleveland Steamer and you can have your way with me.

She also told me that she likes pegging and using double-end dildos to connect her to her lover more thoroughly. My imagination is now running wild trying to picture that. She also likes the taste of a young lady...hmmmm, I know a young lady that needs to be tasted.

I told her that Sienna, having been lonely for a long time, might lean that way with some gentle prodding and a wee dram or two of liquid courage. "She's in the room next to you. If we leave your adjoining door open, she might come to investigate. I'll have to plant the seeds very carefully though. She scares easily and doesn't usually step out of her comfort zone. We were lovers once upon a time.... She feels safe with me. She might just..."

Marlena's eyes brightened at the prospect of burying her face between Sienna's strong thighs. "Ohhh, I would love to bring her over to the dark side, young Jedi. The force is strong with me. I just hope that your lightsaber is fully charged and up to the task at hand."

I whispered, "You're making me hard again Marlena. But fear not, my lightsaber works very well and I can procure some little blue pills...just in case. This Jedi knight will not fail."

She laughed and said, "Good, as long as you don't start talking like Yoda. He sounds too much like Fozzie Bear and I'd probably fall off the bed laughing and break my hip."

We hit it off that night, I wished that I had gotten together with her sooner.

She confirmed the address to her house in Muttontown with the Uber driver and we were off. Muttontown is a very posh neighborhood where grand homes are the norm, I'm impressed. How can she afford this on a machinist's salary?

We arrived at her home and she invited me in for dessert. I began wondering if she was my dessert or if I was hers. Or both. I didn't have to wait long to find out. No sooner had she closed the front door than her shirt, bra, and skirt were off. She was wearing a pink thong and heels, nothing more. She twirled in a circle, then kicked off the heels and ran like the aforementioned rabbit. I gave chase and found her hiding behind her bedroom door.

She closed and locked the door after I entered. "Now, there's an obvious problem here, I'm almost naked and you're fully dressed. We need to correct this fault before we get in the shower. I hope you wore clean undies."

I set a world speed record for getting undressed. I told her that I had to pee first.

She grabbed my hand and dragged me through her bedroom towards the bathroom. "You can pee in the shower." As she passed a closet, she opened it and retrieved a strapon with a rather long dildo attached.

I thought, "What the fuck have I gotten myself into...locked in a bedroom with a dildo-wielding cougar. I'm doomed."

Seeing the look of apprehension on my face, she cooed, "Fear not young Jedi, you will learn many things about yourself before the night is over and I am a gentle teacher. You will let go of things you fear to lose, like your anal virginity."

I waved my hand in front of her, Obi-wan Kenobi style, and said, "This isn't the anus you're looking for, move along...."

She brandished the dildo like a lightsaber, "Your Jedi mind tricks will not work on me young Skywalker, now get that tight little ass of yours in the shower!" " I have much to teach you."

Ohhhh boy, did I mention before that I was doomed?

She locked the dildo in the harness..."Ohhhh, this is my favorite toy," she moaned as it nestled between her thighs. The harness had a rear-facing dildo that slipped easily into her pussy and a knob that would rub her clit as she used the larger dildo on...gulp!...me!...DOOMED.

She dimmed the lights and turned on the rainfall feature in the cavernous shower. It was like being naked in a gentle summer rain. Grabbing the liquid soap, we lathered up and gently washed every part of each other's bodies. I never took my eyes off the dildo as it waved itself at me, right at ass height. She maneuvered herself behind me to wash my back and ass, using far more liquid soap than was necessary. Sneaky twat, she's gonna fuck my ass using soap for lube! Ohhhhhh mamma, what am I gonna do!?

She hissed in my ear, "You said you would do almost anything to please your lady. Do I assume correctly that you're a man of your word?"

I quietly replied, "Yes, I'm a man of my word, just...well... realize I'm giving you my anal virginity, so...gently.... please."

She squirted some of the liquid soap into my asshole like an enema and began to rub the soapy dildo between my equally soapy butt cheeks while whispering, "I told you, I'm a gentle teacher. Besides, I want you to enjoy this, and I'm pretty sure you will. Now, lean over and put your hands on the wall, assume the position. Slow deep breaths, relax. You're gonna love this."

I had gotten a good look at the dildo whilst we were soaping up, the head was very narrow and it wasn't nearly as thick as I'd originally thought. 'Ok, it's thin, this might not be so bad, please let her be gentle'.

An old army saying goes, 'there are no atheists in foxholes', boy do I wish that I had a god to pray to right about now. Please let her be gentle! I was rudely awakened from this silent prayer by the firm, but gentle intrusion of her rubber phallus. I hadn't been paying attention and my anus had just relaxed enough for her to slide it in almost halfway.

She cooed, "See.... you've already taken half of it. Deep breaths...deeeep, like the dildo in your pretty ass. Only eight more inches to go."

Eight more inches! A sixteen-inch dildo!? That should be illegal! But.... it

feels...admit it, Mr. Macho straight guy, it feels fucking great! I would never have thought receiving anal would feel good! It was filling me up! As it inched its way northward, I could feel it moving through my intestines. Oh, I like this... I wanted more! I started to push back against her, trying desperately to impale myself on all sixteen inches. Then I felt the harness against my ass. I continued to push against her.

"See, I told you it would feel great. It's all the way in! And you're still pushing back like you want more! I should have brought the big dildo."

"Ohhh fuuuuuuuck! I do want more! I want to feel it moving inside me!"

She poured more liquid soap on my dilated asshole and grabbed my hips... "Yeeeesss, please fuck me, just don't rip me apart."

She was now in command, and I was about to be fucked as I've never been fucked before. She pulled out about eight inches then thrust into me hard...Out easy....slam...in. She built up a rhythm that was fast and deep. Slam, slam, slam.....on and on it went. She reached around and started jerking me off. This babe knows her stuff. I'll gladly submit to this again.

Then she slowed and pulled it out all the way. 'Wait! Nooo! I haven't cum yet!'

I was turned around and made to lay back on the padded granite bench. She squatted and pushed my legs back towards my chest and expertly reinserted the lance. The dildo was slowly advanced...more soap....the final eight inches were in again. As she squatted and pumped, she held my legs over her forearms. Strong machinist's forearms! Fuuuuck! She's as strong as an Ox!

Note to self, Never piss her off.

She began to hammer me with long deep strokes that constantly massaged my prostate. Semen began to leak from my cock. After five minutes of anal savagery, I wanted to cum, I needed to cum. I had reached the breaking point.

I grabbed my cock and my fist flew up and down keeping time with her pelvic thrusts...I bellowed, "OhhhhhMaaaaarrrrleeeeeenaaaaaaaa!!!! As ropes of semen jetted out of me. I aimed the blast at her, hitting her square in the face with the first two wet splashes. She licked what she could off her lips, never missing a beat... slamslamslamslam! The last of my cum didn't so much blast out, as drool out. I was done. Ripped apart at the anus... drawn and quartered.. done. I hoped that I wouldn't bleed to death.

I hadn't been able to pay much attention to her during this epic onslaught, but I vaguely recall hearing her scream a few times from the dildo in her twat. Every time she thrust into me, her dildo twisted forward and slammed into her G spot and clit. My ragged breathing slowed and my heart rate went from full-on wild gallop to an easy trot.

I was still alive...alive and wondering what my poor asshole was thinking. I could hear it deep in my bowels... 'What the fuck was that!? What did that she-devil do to me!?'

'Shut up asshole, it was fucking great, even if I have to wear a diaper for a week...it was so worth it.'

She was proud of me, she was proud of herself too, "You trusted me, I think the trust was well placed. You stepped way out over the line and, more importantly, you kept your word. I hope you enjoyed that as much as I did. Now I'm gonna pull out slowly, there may be a little poop, but don't worry because I have the handheld showerhead if we need it. Here we go."

She slowly pulled the dildo out, inch by inch until it flopped out of me like a long, overused cock. "Try to tighten your butthole. Wow!, There isn't any poop on the dildo, you must have gone before we went to dinner."

I finally could focus on something other than my ravaged asshole, "Yeah, I did the three esses before I left. Shit, shower, and shave. I'm glad I did. That would have been fucking embarrassing. As far as tightening my asshole...I don't think I'll ever be able to tighten it again. With all that soap lube, I'm gonna fart bubbles for a year. I need a large cork."

Laughing, she leaned over and kissed me gently on the tip of my cock, "Haa! Bubbles...I like bubbles. I know, maybe a little lemon juice will get you puckered up."

Considering what she had just done to me, the thought of her giving me a lemon juice enema seemed relatively normal.

I needed help standing, she held me up with one arm and used the handheld shower to rinse the soap off of us. She's fucking strong, I weigh 230lbs and she's holding me up with one arm! I told her that she still had my cum all over her face.

She looked in the mirror and then back at me, "Why don't you lick it off and then kiss me with it in your mouth?"

What the fuck have I got to lose? I already had a sixteen-inch rubber cock in my ass, a mouth full of my semen isn't gonna kill me. So I surprised myself for the second time tonight. I licked my cum from her face and kissed her, swapping spit for cum.

The teacher was right, I was learning a lot about myself tonight.

1. My cum is sweet.

2. Bigger is better.

3. I still had to pee.

I sat on the toilet to pee, not trusting my legs yet. I also squirted out a load of liquid soap. My asshole was sore as fuck, but at least it was squeaky clean. I went to her bed to lay down. I needed to rest from my anal deflowering. She brought coffee and some itty bitty pastries. We sipped and ate in silence for a while.

She asked, "Do you really think that Sienna will let me make love to her?"

I thought for a moment, "yeah, If you tell her you want to make love to her, she might. Making love, not fucking. She's very sensitive and has been without any love since we stopped seeing each other. The one thing she needs is a gentle hand."

We discussed ways to loosen Sienna's tight moral belt. Once the belt was off, her panties would very likely follow.

Over the next week, Sienna and I discussed such topics as societal norms and mores. Why does society get to tell us who we can or can't love? The rules change with the times. In the 1950s homosexuality was considered a sickness. Seventy years later, it's socially accepted. Don't let anyone tell you who you can or can't be with. I think she understood what I meant. I told her that she was missing out on some great people and some fantastic sex because of how she viewed religious and societal rules.

We all flew down to Aruba and were greeted by hotel staff, "BON BINI NA ARUBA!" Welcome to Aruba in Papiamento. The hotel was a huge affair with some fourteen floors, a casino, and a convention center. I went up to see the penthouse rooms with the ladies. Three-room suites are what they were. Bedroom, living room, computer office, huge bathroom, and a large terrace overlooking the ocean. I could deal with this for a week.

I asked how the two of them got penthouse suites and management got regular rooms. Even the CEO had a standard room. Apparently, Marlena comes from old money. She paid for the room upgrades.

The ladies took a tour of the grounds and headed for the beach while I made dinner and room arrangements. We had decided that I would stay with Marlena and give up my room at the hotel. Saves money for the company, it also puts me closer to Marlena's pussy...and maybe Sienna's as well. The gears are turning...

The girls spent time on the beach, soaking up the Aruba sun. The beach was nearly empty, and there were only a dozen or so patrons at the beach bar. I watched from my shaded cabana as Marlena rubbed suntan lotion all over Sienna.....ALL over Sienna. She kissed Sienna's feet and massaged her legs, then worked her way up her back to her shoulders and neck. Marlena told her to turn over so she could do her front. The look on Sienna's face was one of shy nervousness. Tread lightly, Marlena...very lightly.

I could hear Marlena talking to Sienna in an attempt to relax her a bit. When Marlena's lotioned hands reached her breasts Sienna became tense. Marlena spoke softly to her, gently massaging the tops of the young breasts. Sienna started to relax and appreciate Marlena's delicate touch. At one point, Marlena's hand must have brushed across a nipple, because I saw Sienna's hands tightly grip the lounge chair and she thrust her chest up to meet the massaging hands. Shields are weakening..now at 50% Captain Kirk.

Marlena knows her way around a machine shop and seems to equally know her way around the female defense system.

Occasionally, Marlena would wipe her hands and feed her young lady friend a strawberry or a piece of slippery mango. Deftly holding the fruit just out of reach so that Sienna would have to make an effort to suck it into her mouth, and also suck a finger in at the same time.

Fuck! I had a tent growing in my swimsuit. This was so hot, that the bar patrons had stopped talking in order to watch Marlena's erotic show.

Marlena's hands slowly worked their way down to the bikini line and massaged lotion all over her exposed skin...the front of her thighs, down to her toes, and then up again.