Flirting with the Devil – Part 2 (Anthony’s POV)- {F/27} { M/32} {BDSM} {CNC} { D/s} {Anal} {Forced} {Spanking/Pain/Torture}

****All, some, or none of the trigger tags may be contained in the story. To be on the safe and overly cautious side, if you have triggers of any kind, respectfully, please do not read my content, my writing is not appropriate for you. Read at your own risk. Thanks!****

**To my dedicated readers: I love you guys! I never expected this kind of following, interaction, support, and encouragement. You guys are the best! Writing is a true creative passion of mine. I am open to writing requests, if you have something you would like me to turn into a story. I will confess, I felt a bit of pressure writing part 2, so I do hope it lives up to the expectations.**

Anthony’s POV

It’s Sunday morning and with that comes the daunting reality that the work week grind is inching closer. But the beautiful woman asleep on my arm is begging for the weekend to last a little longer. Her petite frame looks so delicate curled up next to me, her fair skin, green eyes and auburn hair halfway down her back. Don’t think I did much to deserve this beauty. And I am starting to wonder if I took advantage of an unfair situation. I shake away the thought.

Flirting with the Devil – Part 2 (Anthony’s POV)- {F/27} { M/32} {BDSM} {CNC} { D/s} {Anal} {Forced} {Spanking/Pain/Torture}

****All, some, or none of the trigger tags may be contained in the story. To be on the safe and overly cautious side, if you have triggers of any kind, respectfully, please do not read my content, my writing is not appropriate for you. Read at your own risk. Thanks!****

**To my dedicated readers: I love you guys! I never expected this kind of following, interaction, support, and encouragement. You guys are the best! Writing is a true creative passion of mine. I am open to writing requests, if you have something you would like me to turn into a story. I will confess, I felt a bit of pressure writing part 2, so I do hope it lives up to the expectations.**

Anthony’s POV

It’s Sunday morning and with that comes the daunting reality that the work week grind is inching closer. But the beautiful woman asleep on my arm is begging for the weekend to last a little longer. Her petite frame looks so delicate curled up next to me, her fair skin, green eyes and auburn hair halfway down her back. Don’t think I did much to deserve this beauty. And I am starting to wonder if I took advantage of an unfair situation. I shake away the thought.

Flirting with the Devil – [M/32] [F/27] [BDSM] [Anal] [CnC][D/s] [Forced] [Spanking/Pain/Torture/Rough]

*****To be on the safe and overly cautious side, if you have triggers of any kind, please do not read my content.*****

I have finally had it. Everything is unsatisfying. I have been the good girl my whole life and after spending the last five years at the bank working my way up, being polite, wearing my nice pencil skirts and blouses, I have officially had it. I had nearly straight A’s in college and barely knew what the definition of a frat party was. Then I got my job at the bank and being little Miss Perfect just continued. Everything about me and my life is typical, predictable, mundane, boring, and more than vanilla.
Get a tattoo? Nope, Cassandra would never do that.

Show up to work hungover after a Thursday night happy hour that lasted too long. Never.
Have sex on the first date. Not Cassandra.

I don’t know what happened, but I can’t live like this anymore. My life isn’t fulfilling, not even something I look forward to anymore. Granted, I can’t just quit my job at the bank, but outside of those 40 hours a week, I have to find something else to do with my time. Something exciting. Find a passion about something. Anything but continuing on the road I am on.

Flirting with the Devil – F/27 M/32

I have finally had it. Everything is unsatisfying. I have been the good girl my whole life and after spending the last five years at the bank working my way up, being polite, wearing my nice pencil skirts and blouses, I have officially had it. I had nearly straight A’s in college and barely knew what the definition of a frat party was. Then I got my job at the bank and being little Miss Perfect just continued. Everything about me and my life is typical, predictable, mundane, boring, and more than vanilla.

Get a tattoo? Nope, Cassandra would never do that.

Show up to work hungover after a Thursday night happy hour that lasted too long. Never.

Have sex on the first date. Not Cassandra.

I don’t know what happened, but I can’t live like this anymore. My life isn’t fulfilling, not even something I look forward to anymore. Granted, I can’t just quit my job at the bank, but outside of those 40 hours a week, I have to find something else to do with my time. Something exciting. Find a passion about something. Anything but continuing on the road I am on.

Unexpected hero (M32/F22, Slow Burn)

I hate having to stay overnight in the truck stop parking. It couldn’t be avoided with this load. I can’t make the drop until the facility opens in the morning. Most truck stops are noisy and filthy. Sometimes you’re interrupted all night by girls working the lot. Some guys are into that, but I don’t like to pay for my pleasure. I have been listening to a girl getting railed in the truck next to me. What I can’t tell is if she is enjoying it or crying, the sounds coming from her sound muffled and strained. I turn up my radio and start getting ready for bed. It isn’t my business.

I was just starting to fall asleep when a pounding started at my passenger door.

“Open up please. Hello, please open up, I… I… I need help.”

I start to get out of my bunk. Feeling cautious. Listen, these truck stops are a crime haven, this could easily be a fucking scam to rob my ass. Not that they would get much, I don’t carry a ton of cash, but I grabbed my Glock, and kept my hand behind my back as I went to the front of my truck. I looked out the passenger window and there was no one. Then she started at the drivers side. Surprised the shit out of me.

Unexpected Hero (M32/F22, Slow Burn)

I hate having to stay overnight in the truck stop parking. It couldn’t be avoided with this load. I can’t make the drop until the facility opens in the morning. Most truck stops are noisy and filthy. Sometimes you’re interrupted all night by girls working the lot. Some guys are into that, but I don’t like to pay for my pleasure. I have been listening to a girl getting railed in the truck next to me. What I can’t tell is if she is enjoying it or crying, the sounds coming from her sound muffled and strained. I turn up my radio and start getting ready for bed. It isn’t my business.

I was just starting to fall asleep when a pounding started at my passenger door.

“Open up please. Hello, please open up, I… I… I need help.”

I start to get out of my bunk. Feeling cautious. Listen, these truck stops are a crime haven, this could easily be a fucking scam to rob my ass. Not that they would get much, I don’t carry a ton of cash, but I grabbed my Glock, and kept my hand behind my back as I went to the front of my truck. I looked out the passenger window and there was no one. Then she started at the drivers side. Surprised the shit out of me.

The Leather Maker- Threesome, BDSM, M/38, F/35, F/40

Alex and I headed to the festival dressed in steampunk attire with our hearts set on talking to one of the leather crafters about some custom pieces for our bondage collection.

After enjoying the sights and eating some delicious food we went to find the leather maker, Jesse. Everyone at the festival was raving about Jesse being the best leather maker there, so that is who we went in search of.

We found Jesse’s shop and we’re quickly in awe of the displays in the store. Some many beautifully crafted pieces, we couldn’t wait to discuss a custom order fit for me.

“Can I help you find anything?” A gorgeous woman asked from behind one of the counters.

Alex answered, “Yes, we were hoping to discuss a custom request with Jesse, is he around by chance?“

“Custom fit pieces? Those are expensive and take time to do properly.”

“We know, we have used store bought and online products for years and are ready for the best quality now.”

“Well then, let’s she what we can work out. Hello, I am Jesse.”

Disobeying Daddy- BDSM, M/38, F/35, M22, CNC, Forced, Aggressive, Anal

“You are losing your opportunity to fulfill what I asked you to do.”

I was fidgeting in my seat. Twisting my hands in my lap. Alex gave me a set of instructions for our date night. We were staying at a fancy boutique hotel with 5 star dining. I was already in a flashy dress with no panties but he had a set of expectations for this evening. During dinner, I was to flirt with and share a sexual act with our sexy young male waiter, Oliver. I flashed a few smiles, batted my eyelashes, highlight my hard nipples through my evening dress, and even excused myself to the ladies room
In his presence. He wouldn’t take the bait. He didn’t follow me or seek me out during my bathroom trip. I was not going to be able to do what Alex asked me to do. I was going to fail him and have to pay the price very soon.

We finished our dinner and retired to our suite.

“Kneel, while I get everything ready for your punishment. You disobeyed me by not fulfilling what I asked, and you agreed to do. Delilah, you could have just stood up and told him to come with you and he would have.”

Delilah’s show – Recording a BDSM Scene [M38/F35] [BDSM] [Anal] [D/s]

Alex led me into our room, holding my hand in his, I surveyed the room. Several things were already set up. Lighting and cameras were positioned. Restraints hung from the ceiling. The spanking bench was out. The bed contained all four cuffs, the flogger, the crop, nipple clamps, open mouth gag ring, shibari rope, a variety of anal plugs, and a few vibrators. 

Alex put me in front of one of the cameras and began turning them on. He then started undressing me.

“You will be putting on a show for me and all of our subscribers this evening. Delilah, you do not have a say in what will be happening, much of which will be pushing your limits…”
I was already turned on by what he was saying and could feel my arousal and wetness pooling from my core. 

“…your safe word and signal are always in play, but Delilah, I plan to play you like the toy you are and the longer you stay on for the ride the more pleasure I will pull from you.” 

“I am ready to play Daddy.”

“Good girl.”

First Time with Two Men MFM [M/37,F/34,M/40]

I have always had a fantasy involving two guys. A few months ago, Alex and I discussed trying
to make this fantasy real for me. We found Matt online. After a couple months of discussing one
on one and as a threesome, we laid the groundwork for meeting and potentially having a scene
together if the chemistry was great in person. Our agreement would include a consent/non-
consent scene if I gave it the green light. My code to proceed with our plans would be ordering a
Shirley Temple from the bar. Everything was agreed upon and Matt and Alex discussed their
plans separately.
We planned a date halfway between our locations, in a city with an active nightlife. Alex and I
booked a hotel for the two, possibly three of us, and were meeting Matt at a local night club.
Matt fits my type. Slightly older, built arms and shoulders, and tattoos for days. You could easily
see the similarities between Alex and Matt. As a submissive, Alex is my husband and dominant.
He took the lead and pulled us to the bar. He ordered our drinks as Matt approached and
introduced himself formally. The conversation flowed, laughs were shared as the small and
subtle touches started from both men. The attention was intoxicating. The anticipation was
electrifying. I ordered my Shirley Temple from the bartender and set things into motion.
It wasn’t long before I needed a bathroom break. I excused myself and headed towards the
back. I felt two sets of eyes watching me walk away from the bar and down the hall. The
bathroom was loud and crowded. I handled my business in the stall and watched two boots
appear under the door. Whispers started from the other girls in the bathroom. I opened the door
to stand face to face with Matt.
He pulled me forward into him. I put my hands on his chest to catch my balance as his grabbed
my neck, pulling me straight to my tip toes as his lips crashed to mine.
He turned my head to the side and growled into my ear, “You’re mine for the rest of the night
and coming with me now.”
“Wait, what about Alex?” I objected.
Matt gripped the back of my neck, led me from the bathroom and further down the hall and out
the back door. Once outside he slammed me against the side of the building and groped me. I
know what I agreed to but I was still a bit shocked. Matt slide his hand up my dress and hit my
ear lobe.
“No panties, does Alex make that rule for his little submissive?”
He turned me around, pushed my front up against the brick side of the building and shoved two
fingers into me from behind. Matt finger fucked me until I came on his hand.
He shoved his two finger into my mouth, “lick them clean baby girl, quickly, we have a hotel
room to get back to.”
I did as I was told. Matt removed his fingers when he was satisfied. I was a mess, I could feel it.
My dress was disheveled, don’t doubt my make was smeared, my heart was racing, and my
legs were shaking.
Matt eased back, letting me have some space, and I pushed back from the wall only to stumble
as I tried to turn around to face him. Matt caught me in his arms.
“Here, I got you.” He picked me up and cradled me to his car in the parking lot. We were back at
the hotel valet in a matter of minutes.
“Is Alex back in the room already?” I asked during the elevator ride.
“He is.”
Matt opened the room to the suite and ushered me inside.
Alex was there, enjoying a glass of whiskey, half undone, button shirt opened. I started to go to
him and Matt pulled me back. I was still facing Alex as Matt slid the zipper of my dress down. He
pulled one of the straps off my shoulder and I let it fall to the floor. I was naked facing Alex and
Matt behind me. He grabbed my wrists, pulling them behind me into one of his hands. He pulled
loose his tie and bound my wrists together.
He pushed me toward Alex across the room.
“What should we have our little play thing do first?” Matt asked Alex.
“Has she been good for you?” Alex asked in return.
“She has.”
“Then we should probably reward her with a facial.” Alex laughed.
I watched Alex pull out his dick, stroking it as he approached me. I try to be good, especially
when I am getting so much attention from two handsome men. I got to my knees without asking,
proud of myself for doing what I should be doing and opened my mouth for him. He grabbed a
fist full of hair and pulled my head back to look at him.
“Be a good girl and make Daddy cum for you.”
He pushed my head down on him and started fucking my mouth. Tears pricked at my eyes as I
started gagging immediately. He did not go easy on me and this was not gentle. I knew things
would be tougher with two men but this was roughest blow job I have been subjected to. Matt
came into my frame of vision and I could see him stroking his own cock. This is the first glimpse
I have gotten of him and he was long and thick, just like Alex. Panic set in thinking about how
this night could go and if my small frame could take these cocks together.
Alex pulled my head back long enough to catch a few breaths before slamming his cock to the
back of my throat. “Do you want to taste Matt too?”
I moaned yes because I couldn’t speak.
Matt moved closer to Alex, his cock standing tall for me. I willing took as much of him in my
mouth as I could. This started a pattern of me choking on one dick for a few stroke and then the
next. Back and forth between the two. Matt started to cum in my mouth forcing ny head to stay
down on him.
“Drink me up baby girl,” he said.
The sight must have set Alex over the edge because he shot ropes of cum on my face. I had
cum dripping from the edges of my mouth with a cock still stuffed in me and cum in my eyes,
nose, and everywhere.
Alex grabbed a towel to clean me up first. Matt came back with a glass of water and gave me
gentle sips.
Both men were naked in front of me when Matt spoke, “let’s just check in for a minute. Delilah
are you good with continuing with our plans? There will be more pain, bondage, we still plan on
ending the night how we discussed.”
“Yes, Sir, I want to continue.” I remained kneeling in front of the men.
Alex went to the desk which had an array of toys and other items I have seen before and I didn’t
know he had. Maybe they were things from Matt.
Matt pulled the comforter of the bed back revealing the restraints one of them must have put
there prior.
Alex instructed me to stand. He took the tie off my wrists and replaced it with a cuff on each
wrist and the same for each ankle. My body shivered. Matt grabbed something from the table.
“Go to the bed and get on all fours, face the headboard.” I am not even sure which one said it. I
did as I was told, ass and pussy on display for both men. One of them approached me and I felt
the cold metal of what Matt grabbed being dragged along my skin, up my back, around my
shoulder.
“Open Delilah.” Matt placed the small size butt plug into my mouth. “Get it good, warm and wet
for you ass baby girl.” Once he was satisfied, he pulled it out of my mouth, gentle spread my ass
cheeks and pushed it into my tight back door. I fisted the sheets.
“Good, now spread Eagle face down on the bed.” Alex began to fasten my cuffs to the four
corners.
“Tell is your code word again.”
“Orange.”
“Tell us your slow down and ease up code word again.”
“Yellow.”
Smack! Right to my ass. I don’t know which man landed the first blow but I yelped. The hand
carassed my ass cheek as a riding crop came down on the back of my thigh. Then fingers were
stroking my wet pussy lips. I couldn’t tell who was doing what, who’s hand were who’s, or what
would happen next. The dark edges of sub space were closing in on me as my body began
reacting on its own.
I could feel my hips moving into the bed. I wanted more to fill me or something or someone to
rub my clit. I was feeling desperate to come. An assault began on my ass and pussy. The
flogger would come down on my ass hard, then the crop would slap between my legs onto my
wet pussy and then two fingers would push into. This continued until my body was bucking
against the restraints, my ass was throbbing, pussy was soaked and burning, my moans turned
to scream into the bed. I came so hard.
As I was coming down, one of the men, pulled out the butt plug and dragged the next larger one
through my wet folds before pushing the bigger one into ass. My vision was blurry as I watched
the other unhook my wrists and ankles and turn me right side up.
Alex’s face appeared above mine as he pushed his dick into my throbbing pussy. I almost came
instantly from being properly filled with my Dom’s cock.
“Matt come up here and choke her. She is going to soak the bed.”
Matt placed his hand around my neck as Alex fucked me. I couldn’t suck in a breath and I
gushed over Alex’s cock. His moan turned to a growl.
Alex pulled out. Matt let go.
“You gotta try it. You fuck her now and feel this”
They switched places and Matt finally put his dick in me. He felt amazing, thick and hot. Just like
Alex. Alex held my neck and kissed me before he squeezed and sucked the air out of me. I
fished again.
“Holy fuck!” Matt moaned. “You are amazing Delilah.”
Watching these two Gods make love to me pushed me over the edge again. I started to orgasm,
arching moody body clear off the bed, my eyes rolled back and I passed out.
I came to with a man on each side of me. Both affectionately stroking my body. I was still hazy
when Alex asked, “are you ready for your finale.”
I knew what I asked for, but my body was spent. I also didn’t want to waste the opportunity. I
knew the plug was still in me too so it was now or never.
“Mmm hmmm. I want to do this. I want to know what it feels like and to share it with both of you.”
Matt pulled away. Laying flat on his back, his huge cock sticking straight up.
I pushed myself up slowly and climbed on top of him. Impaling myself on his cock. Alex moved
in behind us and slowly pulled the plug from my ass. I leaned forward as Matt took both my tits
confident he was distracting me from Alex’s big dick that was about to violate my ass.
Alex pushed in slowly. My body went stiff, sweat broke out all over me, this was too much.
These men were going to tear me apart from the inside. Matt bit down in my nipple and slide his
other hand between us to my clit and rubbed. They both started speaking.
“Relax baby girl.”
“Breathe.”
“Let him in.”
You got this, you can take us both.”
“We will do the work just open.”
Their voices, those sexy deep voices, soothes me and my body. I could feel my wetness pooling
between me and Matt as Alex pushed in the rest of the way. We were all still for a minute. Alex
pulled back out and pushed in again, he found a rhythm. Each man had a hold of me and Matt
began to thrust alternating from Alex. I was being fucked by two men for the first time ever. So
complete aware of every single inch, every breath, and touch.
I gave my body up to these two men and the ecstasy was beyond my wildest fantasies. I would
never feel like this again, this first time. My orgasm was building and in the build I had a desire
to move and push and pull with both men, letting Alex drive into my ass harder and deeper and
the grind of Matt on my clit. I became a woman possessed, unrecognizable. My head was back
against Alex in abandon. Wave after wave hit me in a never ending orgasm, exploding from my
core.
“You’re so tight.” Alex said as he started to cum.
“I could fuck you all night Delilah.” Matt groaned as he started to cum in me.
I collapsed on Matt’s chest, breathing heavy, dripping sweat and cum from all three of us.