The Office Ogler Ch. 03

Story Info
Date night leads to me being fully broken in.
5.9k words
4.65
20.2k
15

Part 3 of the 3 part series

Updated 06/10/2023
Created 07/24/2021
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Every day I went into work, I couldn't help but feel nervous. I saw the office entirely differently now. I would take the long way to the bathroom because the fastest path went by where she was.

Since that original day, we would text a lot. The next morning I had woken up to multiple messages telling me that I was to report to work as usual and would continue to work there. I honestly wanted to quit but I feared what she would do to me. She continued to flex her dominance over me from there. In the morning, during the day, and into the afternoons and sometimes deep into the night, I would receive texts from her. Sometimes she would even call me. Our conversations would range from the incredibly boring talk of the weather to her going over the events of that night again. It had now been a few weeks and thankfully my butt was alright but she made sure that while the physical damage had gone away, the mental damage lingered. She would tell me about how I squealed and cried while being whipped and that she had the photos still.

Once, I think she masturbated on the phone. She had been making weird groaning sounds and moaning and breathing heavily while she commented on my cute "crying babyface." Admittedly, it gave me a boner. A guilty boner.

Weeks had gone by now though and I still wondered what the hell she wanted from me. Was it over? I felt like we were in some sort of fucked up quasi-relationship. I hadn't had many girlfriends but this felt like a relationship because we talked constantly, even over the phone, and she seemed genuinely interested in my life. She made fun of me constantly and the age difference was quite large but when she wasn't re-describing how she had beaten me the situation seemed okay. Maybe I was brainwashing myself because I felt like I was slowly convincing myself that this was a good situation; I had this beautiful woman who seemed to be obsessed with me. Yet that same beautiful woman had shown intense cruelty and seemingly got off on it.

I was confused.

And the confusion continued when Friday night she texted me at work. She made it clear I was always to respond to her even during work hours so I picked up my phone and unlocked it. It was a few messages.

-You told me already you had no plans for tonight except for your computer games. Tonight, you're going to come over to my house. I want you to go home first though and take a shower and pretty yourself up. Wear something nice and fancy-

The next message included her address and expected time. 8 PM. Oh god, the anxiety ran through my body immediately. I already had planning-anxiety where I hated when new plans suddenly popped up on me. I needed a day to prepare to do really ANYTHING. The anxiety was quadrupled by the fact that this was Abby inviting me over. A beautiful fearless woman who could have any man she wanted. She was in her 40s but any guy would count themselves lucky if she even looked at them. Then finally, there was the fact that this was my abuser...

Excitement also went through me. Why was she inviting me over? I had to dress up? Was she intending to make this some sort of date?

I wasn't sure but as soon as 5PM hit, I wrapped up what I was doing and sped on home. I wasn't exactly sure what to wear. I quickly took a shower and used body wash, shampoo and conditioner, and my facial scrubber. I shaved the little hairs that grew on my cheek since I was still incapable of connecting most of my facial hair. While still naked, I applied body lotion. I jogged a lot and as it got colder my skin was drying up bad so moisturizer and lotion everywhere was a requirement.

I threw on a nice thick navy-blue long-sleeved turtle neck shirt. My soft comfortable underwear with a pizza design on it. Khaki pants. Black belt and black socks. A nice pair of leather business shoes I had actually gotten specifically for this job but had only worn once since they allowed you to wear anything. I then sprayed some cologne on myself and felt good. I was a bit excited to dress up and head out. I wanted to please her. I wondered if that desire to please was from wanting to make her happy or wanting to not be hit. Or both.

I got into my car and drove over to the address she mentioned. But first I stopped at a quick liquor store to grab a bottle of wine. I made sure to go to a different liquor store than the one near my home. I was slightly embarrassed to be picking up a bottle of wine on a Friday night while wearing this outfit.

She was in a small town over. Definitely a nicer and richer neighborhood. She was the manager of our loan department and I'm sure she was paid nicely because of it. I stopped before her street however as it was 7:55 PM and I wanted to arrive exactly on time. I waited a minute or two and then finally pulled into her driveway. I proceeded to knock on her front door from there. Awkwardly swaying back and forth and looking at the dark street. I wondered if I looked weird.

The door suddenly opened and there she was.

Her height matched mine at 5'11. She stood in the doorway smiling at me. She had on a satin bluish blouse on. The first few buttons left undone which probably made it so that her breasts shivered as the cold air came in. Her blouse tucked into somewhat tight black slacks that had a nice gold button at her crotch. She had on a beautiful diamond necklace and a nice thin watch. She was barefoot. Her hair was pulled back at the moment into a beautiful bun and her blouse was rolled up. She was cooking something.

I felt like a cartoon character. I was staring with my mouth wide open. I then slammed it shut and stammered.

"H-hi Abby,"

I presented her the bottle of wine. It was a completely random bottle of Rose that was $30. I had taken the $30 tag off though.

"Perfect," she glanced at her watch, "right on time. Good boy. And bringing a bottle of wine, good manners."

She took the bottle from my hand and walked into the kitchen.

Looking into her house, from the left of the front door there was a rug staircase going up to the 2nd floor. The room I was staring into was the living room. On my right was the couch and a big flat screen TV on the furthest right wall. Directly in front of me was the hallway that went left to right. I couldn't see what was to the left on the hallway but to the right was the kitchen. The kitchen and living room were separated by a wall; the wall had a large open window in the middle of it that allowed someone to see into the kitchen or vice versa.

She had disappeared a bit as she was deeper in the kitchen but soon appeared in that window area between the living room and kitchen.

"Come on in and close the door already! It's cold out there. Make sure you take off your shoes. You can sit on the couch,"

I quickly closed the door, maybe slamming it a bit too hard but thankfully she said nothing. I sat down on the couch and just sat there twiddling my thumbs. I would look up through the big hole in the wall and see her cooking and occasionally washing something. I offered to help and she said I was sweet but that she wanted me to stay in the living room. It smelled like alfredo.

Eventually, I heard her signal that she was finished. I didn't want to say anything though so I sat there staring at the blank dead TV. I wanted to pull my phone out but worried she may say something. I heard her walk from the kitchen into the living room and her hands landed on my shoulders. I felt her breath on my ear.

"It's okay. You can relax for now. We're just having some dinner." She spoke in an alluring and sultry way. I nodded my head and thanked her and stood up. I followed her into the kitchen. What did she mean for now?

I was right and it did end up being alfredo spaghetti with some fresh baked garlic bread. She opened up that bottle of wine in a way that only someone who drinks a lot of wine could. I struggle to use a wine opener and always forget how it works but she had it popped open in mere moments.

The food was delicious and the wine was alright. I hope she found it to be pleasing. I thanked her again for the meal as we ate. I felt it only best to continue to thank her for the food. I needed to be on my best behavior. After all, I was in her home. We made light conversation. We discussed work and my current metrics with the loans I processed. She told me I was doing a good job and I couldn't help but feel overwhelmingly happy about that. I'd be lying if I hadn't begun to try even harder at work after my mistake of being a creep.

After the food, she put all the dishes into her dishwasher and lightly grabbed my hand and pulled me to the living room. Every time she touched me a shock went through my body. Her hands were so soft and delicate. My dick inevitably grew.

She laid down on the couch and grabbed the remote. Her hair was everywhere now as she released it from its bun. Drapery over her big breasts. She looked at me and curled her fingers; telling me to come over to her.

"Lay on me sweetie," I got onto her large couch and wasn't exactly sure how she wanted me to lay on her.

She patted her breasts. I got on all fours and scooched myself on top of her. Her arms wrapped around my body and I let myself fully lay on her. My head being supported by her breasts. I was in a state of paralysis. I felt I was in the safest and most dangerous area. I felt like she had me and could protect me. But at the same time, she could beat me senseless. Her arms tightened around me and I squeaked a bit.

She gave out a light laugh before flicking the TV across a few channels. Eventually, she went to Netflix and put on a random Christmas adult romcom.

Her hands were like a seatbelt strapped across my waist. Occasionally though, she would let go and run her fingers along my arm. The hairs would stand up and my chest would beat rapidly. Since laying down, my heartrate must have been sitting in the 120s. I was laying on her large breasts and when my head would move, they would jiggle and move ever slightly.

The romcom continued and while I somewhat understood the plot, I was not focused on it. My entire focus went to making sure my dick didn't get incredibly erect. I felt a sense of embarrassment but also comfort laying on her. I couldn't see her from this position. I didn't know if she was looking at me, looking at the small tent forming in my pants, or just ignoring me completely and watching the movie. She would occasionally chuckle at the movie and so surely, she wasn't paying much attention to me. I was in my own head now trying to understand the situation and where things would go from here.

"What's on your mind?" she asked me.

"O-oh uh, nothing really. Just watching the movie. Um, this is nice. I like this,"

Her arms tightened around me and pulled me in a bit. My body squishing against hers as her surprisingly strong arms were locked against me. My head pushed into her boobs more and for a split second in that tight embrace she was giving me, my cheek touched skin instead of her blouse. My cheek touched her breast!

"I'm glad to hear that. So, you're comfortable in this position?"

"Yeah, I'm comfortable," I remembered to continue to thank her. "Thank you for inviting me over. And dinner. And for allowing me to be so, well, uhm, like close to you but like physically, well, not that I, uhm, I don't know, thank you!" I spoke so quickly and sporadically

She laughed and I could hear her smirk.

"Turn over,"

I started to roll off her a bit but then she pulled me back.

"Turn over without getting up"

I started to turn over but realized a problem. My head had been laying on her breasts and while that seemed to be okay from behind, now if I turned over my face would be right into them. Plus my dick would be between her legs essentially because of the tent. And what would I do with my hands!?

"I said turn over. Do it now or I will not be happy,"

Upon hearing that, I quickly rolled over and her legs split apart a bit before clamping back together. My cock was now squeezed between her legs and I had a face full of breasts. I finally could see her now though.

Her face was tight for a second with a slight sneer which then thankfully turned into a smile as I fully rolled over. I looked up at her. Her left hand then craned my head to look back at the TV. She began to scratch my head.

What an insane situation this was. This was amazing. The only issue was my cock was uncontrollable now. Being tightly gripped by her legs as it pushed into the couch cushion made it only harder. I felt the urge to thrust but tried to keep it within me. I wanted to just start fucking and thrusting into the couch with the pressure that was on my dick.

I closed my eyes and tried to control any bodily instinct. I breathed a bit heavily with my mouth open. I would remember occasionally to close it and not breath so heavily but just a few minutes later, my mouth would be ajar and I'd be heaving. It took my full attention and focus to not show my true nature of being a horny creep.

She then brought up her right hand and caressed my face. Her thumb lightly slid along my lips. She pulled my bottom lip down a bit before letting it flap back up. At the same time, she said,

"Why are you breathing so heavily baby?" My mind was becoming blank. She was teasing me and pulling me along. I was her little puppet and she was just playing with me.

Her thumb then once again slid along my top lip. Caressing my cheeks and then pulled my bottom lip again. This time, however, she pushed a bit more. I opened my mouth and she lodged her thumb firmly in my mouth. Her fingers gripping my neck and jaw. I closed my lips around her thumb but kept my tongue towards the back of my mouth. I closed my eyes.

"Suck on my finger,"

I immediately sucked deeply on her thumb. My tongue wrapping around her thumb and rolling around. I pulled her thumb deeper into my mouth. My cock was pulsating at this point. Jerking by itself and pulling and tingling.

"A-Abby? I'm really sensitive right now," I squeaked out. It was muffled because of her mouth but still understandable. I was scared of her reply but was even more scared of what would happen if I came in my pants and it went through onto her or her couch.

She pulled her thumb out of my mouth.

"Get up and strip. Take all of your clothing off," I didn't need another word.

I was up in an instant and pulled off my shirt and my pants. Within a moment I was doing the leg shake to get my underwear and pants off. I was in such a rush that I wasn't immediately embarrassed of my petite and small frame like I usually was. I was skinny with runner abs. All I really did was work, play games, and jog. I was proud of my running but it still left me with low self esteem as I was skinny and weak. My arms and legs and chest were thin. My shoulders immediately slumped down instead of being big and broad like other men.

My dick was just an average size of about 6 inches. Maybe a little bit less but regular and average. Uncircumcised.

I stood there. My hands gripping one another behind my back. The air making my small tiny nipples erect.

She still laid there and looked me up and down. I surely wasn't impressive but she looked at me hungrily?

She pointed her finger downwards to the floor. She then finally stopped laying down and set up on the couch with her feet on the ground. I immediately got onto my knees.

She continued to direct me with her fingers. I crawled over to her and both her hands began to caress my face. Her fingers slowly began to get aggressive. Initially she scratched my head and ran her fingers lightly across my cheek but then they started to grab me more intensely. Her left hand grabbing the back of my head making it so I couldn't move. Her right hand around my neck. At first, she was just gripping my neck but soon it was much more than that.

She started to choke me. I looked up at her worried and scared but this only made her tighten her grip on me. She looked deep into my soul. Her eyes were dark and full of lust as I began to run out of air and choke. I must have been turning a different color after a certain point. A tear sprang from my eye and rolled down my cheek.

I began to pull my head back a tiny bit but she held me still. Her grip was so tight, I felt I might go unconscious there on her living room floor. I mouthed "please" to her and nothing. I finally started to feel lightheaded before she finally released me. She had been leaning forward while sitting on the couch as she choked me but now began to lay back. Her leg crossing over the other.

I gasped desperately for air. I coughed and choked on it. Sucking in everything I could get. The sudden rush of air made a few more tears flow down. I swallowed down the salty tears and looked up at her with fear.

She had treated me so delicately tonight but now there was a shadow over her face. A sudden darkness that told me that the woman who earlier was caressing me was gone. The woman I had gotten to know in that meeting room: She was back. Yet even with that fear, my cock stood fully erect. If anything, the choking had only gotten it harder. If she even touched my cock, I would surely shoot many many many spurts of thick cum.

I stayed there. On all fours. Looking up at her wondering what was next. I rubbed my eyes to dry up all the tears.

"Turn around, face into the floor, ass up and pointed towards me. Knees shoulder-width apart. Arms in front. Close your eyes," Each word dripped with lust and fervor.

I quickly followed her command but left my butt a bit limp. I was scared she was going to whip me again. The memories of the pain flooded back. At least I wasn't handcuffed now. I could get up and run if I really needed to. Did I want to run?

I heard her stand up and spank my butt lightly with her hand.

"I said ass up you little slut," I pushed my butt higher.

I closed my eyes tight and got ready for the punishment ahead.

"Now stay in that position. Don't move a fucking muscle,"

The next few minutes I heard her leave the living room and then come back. The movie started up again and I made a slight move but then put myself back. She was testing me.

The movie continued on for ten or twenty minutes. I'm unsure of how long. I simply stayed in the position. My ass presenting itself. My soft pale sensitive skin had goosebumps all over.

My arms began to get sore being in that position but I knew better than to move. She would occasionally chuckle and laugh at the movie but beyond that said nothing. I felt like an ornament in her living room. That someone would come into the house soon and she would show me off as the house "slut" if to use her words. Just another decoration.

My heart finally began to stop beating so rapidly. I had been basically felt like I had been on a run this entire time with the way my heart was beating. But as the movie played on and clearly was reaching the end, I began to get more comfortable. It was the same feeling that overtook me in the meeting room.

The feeling of defeat. That there was no reason to fight or be uncomfortable as what she was going to do next was completely up to her. I had no reason to concern myself with what was coming next as it wasn't my responsibility and I didn't have the capability to change it. It was set in stone with Abby. Abby controlled me.

The movie finally reached an ending. The couple getting back together and the family celebrating Christmas. The romcom ended and the credits began to play.

Netflix began to play a trailer and then another movie. She wasn't messing with the remote it seemed and didn't care I presumed. I couldn't know. I simply kept my eyes shut and waited.

After a few minutes of the next random movie, she finally broke the silence. It had been 30 or 40 minutes at the least.

"What's on your mind?" She repeated the same question as earlier.

12