The Office Ogler

The door gently closed behind me. I was struggling to keep myself stable. The handcuffs limited my ability to keep myself upright. She shoved me forward so that I collapsed onto the table. My legs spread apart to hold my unbalanced body.

Thankfully with the door closed if anyone else came into the office they wouldn't see this. However, the windows pointing outside were still viewable. The blinds were still open but thankfully it didn't point to any parking lot. It pointed out into the dense woods where hopefully no one would be. The long wooden table was bare and empty. It hadn't been used in a while because of Covid and beyond a few chairs there was really nothing in this room.

I suppose it didn't matter though. I don't know what she intended to do to me but I'm sure once she was done, she would expose me. She had the evidence. She had the capabilities to not only get me fired but to publicly label me a creep. She could plaster this online. She could tell my parents. In this day and age, even some pictures of me staring at her ass would ruin my life. Now I was handcuffed and there was no telling what she would do.

Tears had already been streaming down my face from the physical pain but the emotional weight of what I was in for and how fucked I was made me sob. I was sweating profusely. I could feel my shirt clinging to my pits and it seemed like my jeans had gotten suddenly tighter. My heart was beating so quickly.

I let my head droop down so that my forehead hit the table and my vision was dark. I could hear the light pitter patter from my tear drops hitting the table. The moments seemed to be taking forever but only a few seconds had passed since I had entered the room and only a few minutes since the destruction of my life had begun. I suddenly remembered that I had been barely breathing. My body was already becoming a wreck and I was forgetting oxygen.

I took a deep breath and with a snap it seemed like the physical world rushed back to me. The air filled my lungs at the same time that my hair was suddenly gripped and I was yanked back. My neck craning first before it ripped my body up with it. I scrambled my legs to keep myself upright and not collapse onto the ground. I yelped.

"Stop fucking crying. I stepped on you a bit and here you are sobbing like a little baby,"

"I'm sorry, I'm sorry," a hiccup forced itself between my words, "I'm scared. Please let me go. I promise I will never show up here again. I'm gone. You'll never see me again please. W-why have you handcuffed me? I'm sorry for what I've done. Please let me go,"

She made no sound or movement but the tight grip on my hair was not let go.

I continued, "I know I'm a pervert. I promise I will never make this mistake again. B-besides, this is maybe a bit extreme?"

I continued to take deep gulps of air and common sense seemed to come back to me as well. This was a bit ridiculous. I know I was a creep and that she could fuck my life up but why was I handcuffed. She was hurting me!

"You're hurting me please stop, I don't want to be here"

She let go of my hair and I collapsed forward.

Suddenly, her arms wrapped around my waist and my incredibly tight belt, that often-put pressure on my dick throughout the day and gave me inklings of pleasure, was released. She whipped it out of my jeans. These jeans were already a bit too big for me and they collapsed. They fell and folded at my shoes. The hairs on my legs stood at attention as the cold air circled my now exposed bottom half.

She laughed. It echoed in this big meeting room where it was only the two of us.

"WHAT ARE YOU DOING?" I screamed. I was terrified. Within a moment, she simultaneously grabbed my hair and grabbed my hip. She whipped my head back with her left hand and in her right, I could feel she was still holding my belt. I whimpered as I stared toward the ceiling.

I heard her place the belt on the table and then listened as she fiddled with something. I could hear a chain jangling before suddenly my mouth was filled with some sort of plastic object. A ball that forced my mouth wide open but seemed to cover the entire opening so that my sounds were muffled. She let go of my hair and used both hands to strap it around my head.

I began to put everything together. As my head moved back to its natural position, no longer held by her tight grip on my hair, I was able to see everything she placed on the table. It was an assortment of instruments. Things I had seen in random pornos. Not that I watched those kinds of porn but just something that when you watch a lot of porn you were bound to run into. I now understood what the sound was when she had been rustling through her desk.

"I didn't think you would be that loud. Thankfully no one is here but we can't have you screaming in the office." She slapped my cheek lightly, "I don't think you'll be making any more sounds now though."

I tried to speak but nothing came out. The ball restricted anything from leaving my mouth. Well, except for the spit that began to pool up and drool out of my mouth.

I realized that through all this I had still yet to actually look back at her. Even when I screamed, I had stared straight forward, not daring to look her in the eye. I finally turned my head and she met me dead on. Her eyes peering into my soul. A gaze that put me in a never-ending loop. An icy stare that froze my entire body and then was immediately melted by her beauty and confidence before eventually freezing me over again. I whipped my head back and stared straight at the wall again.

I felt my dick stir. I could feel it grow just a tiny bit. I could feel a hiccup from my earlier crying get caught in my throat. I was on the verge of crying again as my cock seemed to grow in size. I didn't know what to think.

Her hand touched my underwear. She moved in circles over my right butt cheek.

"What cute underwear you have. An adorable design," she laughed as she continued to touch my butt. I was wearing the Halloween edition of the most recent MeUndies shipment. I had sensitive skin and found this was one of the best undies to wear. But now I simply felt embarrassed.

Her hand then continued going from my butt to the front. I could feel that she was within a few millimeters of my dick. Her fingers stretched out and touched the seam of my undies. They pushed themselves so that they were between my skin and underwear. She then pulled down and took my underwear cleanly off. It dropped to rest with my pants. Goosebumps rippled across my skin as now not only was my butt showing but my dick was completely out.

I was fully exposed and felt true terror. I began to shift and try to move a bit but she was quick. Her right hand gripped my hip and kept me still. Fingers pushing into my soft sensitive skin.

"You're going to stay still now. No movements. Understand?" I grunted, forgetting that I was gagged. She let go of my hips, seeming to understand what I meant by my gagged noise.

"For tonight, I've decided to take leniency on you. Leniency in that your punishment will not be as severe. To be quite honest, your naivete and young baby face and," she squeezed my leg a little bit before pulling away, her fingers streaking across my skin as she walked to my left side to be in front of me, "soft smooth body has convinced me that maybe you could have a use. Maybe I can really help you. You clearly have never had a woman touch you before"

My dick jumped a tiny bit.

She sat on the table and looked at me deeply with that same gaze as before. And just like before it evoked a deep visceral feeling from within me. Her eyes were that same deep dark blue. I was still getting used to seeing her without her mask. I was starstruck. Her nose was tight and thin. Her cheek bones were so prominent and her jaw line was strong and intense and sculpted. The golden hair fell completely straight to the ground. It was a whirlwind of intense infatuation. I was completely caught and we stared for what felt like hours. In reality it was maybe 30 seconds.

"But first!" she got off the table and walked back behind me.

"You still need to be punished. This will hurt. This will be the first time tonight that you'll have a real reason to sob and cry so feel free to let all that out. Oh and I think we need to take some pictures so we can have a before and after,"

I moved suddenly but it's as if she was expecting it and her fingers touched the back of my shirt. At this point the sweat had dried up but it still clung to me tightly. Her fingers gently kept me still and I stopped moving.

However, not even her fingers could keep me from trembling. I shook deeply and I questioned what was next. What did she mean that she was going to take leniency on me? Naïve? Was she going to ruin my life? What punishment was I going to receive? These questions and more flooded into my head. The room was silent once again except for my nose rushing with constant air. The pitter pattering on the table continued however not with my tears but with the drool that leaked from my mouth.

I continued to stare straight ahead. I didn't dare move my head or even move my eyes. It felt like she would be able to notice any small shift.

Then abruptly, my vision was gone. A velvety feeling ribbon was wrapped around my eyes and I was blind. I wondered just how scared one person could truly get. I was shaking and quivering and the cold air was not helping me.

I heard a few snaps of a phone camera. I heard it behind me and in front of me. I felt humiliated.

I tried to tell her I was sorry and to please let me go but the gag destroyed all my pleas. With my voice and vision taken from me I felt it was over. I needed to just accept what was about to occur and try to just get this night done with.

Abby was in control. I was not. Any thought I had concerning how to get out of this whether it was to try to fight back or to plead for my life was futile. I had low self esteem already but that had nothing to do with my next thought: I was a weak, skinny, young perverted white kid and there was nothing I could do. It was best I accepted what was coming and appreciate the leniency she was apparently going to show to me.

These sick thoughts of capitulation flooded my mind as I heard something slide off the table.

A hand pushed me fully onto the table so that my chest was flat on the table and my butt pointed outwards to her. I brought my legs together and squeezed my butt tight. The sight must have been pathetic.

Finally, the air whipped and something lashed my butt cheek. I screamed but the gag kept it all back. It reverberated in my own mouth and body and yet within a few seconds another one came crashing onto my butt. The pain cascaded over me and my legs wobbled, threatening to collapse.

It was my belt! It was my fucking belt. The belt that I squeezed my cock with every day was now causing so much pain, I thought I might die.

My right leg shook intensely.

She spoke and commanded something of me but it was in one ear and out the other. I couldn't think or process what she said as the two lashes to my butt were searing. While I couldn't process what she stated, I understood what she meant.

I was to not move an inch and take this punishment fully. I steadied myself by leaning harder onto the table. My head laid down and my ear pushed into the table. The vibrations going through the table caused by my trembling was all I could hear.

A few more seconds passed and then the next lash hit. And then the next. And the next.

I thought I had no more tears to shed but she was right. This was a real reason to sob. It all came out of me and I shook and shuddered. Tears sprang from my eyes and my drool pooled on the table. It seemed to continue on forever.

My ass was scorching as each lash seemed to cause an exponential effect. The current lash making the last lash feel worse which had already affected the previous lash.

Time stretched.

At certain points she would touch my butt. Her fingers cold and felt soothing on my burning skin. But it would be short and quick, as if she was inspecting the damage before laying another lash across it.

There was a rhythm to how she beat me and my muscles tightened every time the next lash was expected. However, she clearly knew what she was doing as she would break this pattern every once in a while. She never allowed the pain to become cyclical and routine making it so I never fully got used to it. I was on edge and it did not feel lenient.

Finally, I heard what I presumed to be the belt hit the floor. She dropped it.

"Alright honey, it's over," how dare she beat me so senseless and then call me honey. What was this?!

I immediately collapsed. My legs became jello and I hit the ground. I sprawled across the floor with my butt facing upwards. It continued to burn.

Suddenly the ribbon was pulled apart and I could see again. My cheek was kissing the ground and looking to the right all I saw was her feet and long legs. Next, she bent down and removed the gag from my mouth. My face was a blubbery mess.

My mouth finally closed and I gulped down my own spit and salty tears. I opened my chapped lips and then closed them immediately after wondering if it would be okay to even say anything. Did I have anything to say? I felt I should say something after having been gagged for so long and after this terrible experience but I was frightened at what she may do next.

"I hope you've learned a lot from this. You will never make the mistake of staring at me or any other woman again like that,"

I choked out "leniency?" and then braced for her to hit me again realizing how rude that sounded.

She laughed.

"Yes honey, leniency. Yes, the physical punishment hurt and was harsh but it could have been worse. However, you misunderstand. I am being lenient by not ruining your life after this. I've decided I will keep you. Initially I intended to beat you into submission and then expose you but I decided that you're just so cute and naïve that it would be unfair to discard you so quickly. I will turn you from a pervy creepy boy into a man. Now what do we say?"

I turned my head to look up at her. I saw her smile and I wanted to cry again but at this point, there really were no tears left.

I choked out "Thank you..."

"You're welcome Honey. Now, let's get you all better."

I was laying down still on the ground but she began to pull up my underwear. Thank god for the soft fabric. It still burnt and I gasped as it went around my butt but it could have been worse.

"No one is here anymore and you should be fine to go out in your underwear in the parking lot if you want to avoid wearing those jeans because of the pain. You're going to add my number to your phone and I will send you instructions on dealing with this. Now come on, you need to head home and relax,"

After that, she began to help me get up and get all my things. It was a quick few minutes and she touched me gently.

As she set up the office to be locked up for the night, she had me wait at the front door for her. I leaned against the wall. She strode out and had me grab onto her arm. She escorted me to my car and I leaned on her for support as I limped.

Soon I was placed into my seat and my butt burned intensely.

She kissed me on the forehead and told me "You came in the office ogler and have come out a much better boy already,"

The confusion swirled in my head. The feelings of abuse and care frightened me and I wondered what would be next. She walked to her own car and began to leave. I drove home and as soon as I managed my way into my room and into my bed my phone dinged.

My first message from her.

I stared up at my ceiling and felt complete fear. What was next? I curled myself into a ball and cried myself to sleep.