On Friday Night My Wife Had Some Friends From Work Over. We Ordered In And They Relaxed And Had Drinks,

FM Spanking, Spanking,

Last Day

This was it. It was time to transfer the money and disappear. It would be my last day at work. I was nervous, naturally, but not expecting any trouble. I arrived at the office at the normal time, went to my computer, and started transferring the money from the business account to a personal one. I left as this was happening, locking my office door to go use the bathroom, then headed back to the office.

I hadn't even noticed the door was no longer locked when I entered, and halted at the door to see the company fraud investigator, Cynthia Lockwood, sitting in my chair, her booted legs crossed as she looked at me with a smile.

"Well, well, this is very interesting, Ryan," she said. "Obviously I have caught you stealing, but I had a look around inside your computer and found some very interesting things as well."

I blushed and trembled, rooted to the spot. I should run, I should fight, but I knew I was caught, and was about to be very embarrassed.

"Apparently you fantasize about being arrested by a woman," she told me. "And fantasize about being spanked by one."

She laughed at my blush. "Well, sir, as of this moment, you are under arrest. Step over to that wall and put your hands on it."

I shook, wanting to burst into tears. I'd been so close to pulling this off, only to be caught by the female investigator. As I walked on shaky legs, knowing I was taking my last free steps, I reflected - was there a part of me that wanted this to happen?

She moved behind me as I put my hands on the wall, and she searched me VERY thoroughly, finding the shameful evidence of my arousal. "Hands behind your back."

I obeyed, and I heard the clicks as the woman handcuffed me. She double-locked the handcuffs and pressed me to the wall.

"I should bare your bottom and spank you right now like those women in the pictures," she mocked. "But that wouldn't be very professional. So you'll have to stay content with the female officer who's on the way to take you to jail."

A single tear escaped my eyes. Yes, I'd fantasized about being arrested by a woman, but now that it was happening, the shame was overwhelming me.

fucking a pretty boy and him covering his blushing face just so you can pull his hands away and pin them down

Could you do Sydney Sweeney with pegging and chastity please

Hmm... that's a good request.

You lost yourself for a minute as you stared at Sydney. It was still kind of surreal to be here with her... again. She used to call you only a few times a year. Inspect her chastity cage, then fuck your ass for hours. Then when you woke up, she would be gone.

This time though, she'd called you up again a few days after your last 'session' with her. She got interrupted by call and had to leave you unfinished.

You got quite nervous when you got that call from her so soon, this your body still got crazy hot and now that you stood there in a hotel with this bombshell of a woman you were trembling with nerves.

After you entered you found in her elegant black dress looking just absolutely stunning. The dress put her ample assets on display which made your caged up dick more that excited. It throbbed and ached in its cage. The keys were hers. The only orgasms you had were given to you by her.

"I'm glad you came." She spoke up, breaking the silence that had taken a hold of the room. She took a step or two away from the windows, grabbing the curtain before pulling it close, her now only dimly lit by the few lights in the room.

"Of course, Miss Sweeney." You replied, remaining polite even through your nerves. Even though you'd been here plenty of times before. A sweet smiled formed on her face.

"Always so sweet and polite." She noted as she walked toward you. She placed a hand on your cheek, gently caressing you. Her eyes darted up and down. "and so -fucking- submissive." She purred sending a rush down your spine.

She took another step closer then she pulled you in for a kiss. You froze on the spot. She had never kissed you before in any of these hookups. You were just a little fuck toy for her.

It didn't take long for you to be swept up into a passionate exchange. Sydney kept her lips planted on yours as she started taking off your clothes. You helped her out and soon you were naked and being shuffled toward the bed. Sydney's hands were all over your back and your ass before she pushed you onto the bed leaving your breathless.

There were something in her eyes beside the usual hunger. She usually would make a little show when taking off her clothes but this time she rid herself as quickly as she could revealing her naked perfection underneath.

Your cock strained as you watched her. She crawled onto the bed and she laid her body against yours and started kissing you again. Your heart was melting quickly and she turned your brain into mush.

Sydney pulled off again after a while, chuckling as she saw the lovestruck expression on your face.

"Miss Sweeney?" You spoke up softly as she stepped away to slide into her harness.

"Yes, my pet?" Her words made you shudder. Another thing she had never called you something like that before.

"I.. uhm.." You tried to look for the question that had just escaped your brain as soon as she turned around and you saw her cock dangling there ready to take your ass.

"Lost your tongue my sweet boy?" She teased you, stroking her toy for you. Your mouth was still open but you still couldn't speak.

"Turn around." She commanded and your body obeyed without thinking. You felt Sydney get onto the bed with you. then her strap found its way onto your ass and like the well trained little slut you were it easily spread you open and filled up your boy-hole.

"Oohhn.. God..." You moaned as inch by inch entered your ass until you felt her deep, deep inside you. Her body leaned over you and you felt her breasts press up against your back. You groaned as her toy was lodged inside you.

"To answer your question. I want you to be more than my occasional fuck toy. I want you as my submissive." She whispered, your whole body started shuddering as you felt her warmth breath on your neck.

And hand traced all the way down your spine before she used both hand to grope your behind.

"Unless you object to that idea." She added, slowly pulled her strap back out as her hands now slid onto your waist.

"Nnnoo... Miss Sweeney." You moaned.

"I didn't think so. I molded you to only cum by my strap, didn't it?" She playfully mocked you, slowly pushing her length back inside you till she was buried inside you to the hilt.

"Nngg.. y.yes... I am your little slut, Miss Sweeney." You purred in between moans and whimpers.

"Yes.. you are." She said with a growl. Her fingers dug into your skin and she suddenly started pounding you hard and fast like she always would. But with all that had happened it felt different.. better... so much better.

You heard her grunting and cursing at you as she drilled you.

"You are mine.. all mine." She growled in between powerful thrusts sending wave after wave of pleasure through your submissive body.

"Yes.. yes!! I'm yours!" You cried out back to her. Crying out when she smacked your ass.

"Shut up you little bitch. Shut up and take my cock!" She spat back at you melting you brain even more. Long deep, sultry and slutty moans coming from your lips.

"That's it baby. I want to hear all your whorish little moans." She encouraged you, giving you another little smack for good measure.

She kept fucking you hard until you screamed out in a orgasm that hit you like a fucking tidal wave. But Sydney did not even slow down for a second. She just laughed.

"Yes!!" She yelled at you as you let out the sluttiest moan she heard all night as she fucked you through your first orgasm of the night and it wouldn't be your last. She drained your balls dry and fucking you till you yelled out your safe word when your body couldn't take anymore.

You fell asleep in her arms like you always had and come the next morning. Your heart fluttered when you opened your eyes and found yourself staring at her face, she was still sound asleep and look so peaceful.

Your dick started throbbing away as happiness overflowed inside you.

She stayed this time.

You really were her pet now.

Wait for it….💥

I was restrained and gagged and had already taken a fair amount of strikes and impact with hand, paddle, and the cane. This clip was taken from a vid that goes on for another 2 min or so in similar fashion. The caning carried on for some time afterwards. Let’s just say the sheets were a bit messy by the end of it all.