IT Nerd and CEO Boss

I had recently graduated and started a new job at a company in Delhi. I had only just started and I was only trusted with menial tasks such as replacing faulty computer equipment for the employees.

My role was redundant and I often thought why I spent so long studying for such a menial role. A habit I developed was to spy on employees and their favourite internet searches. I found it strange that certain employees would always search porn when they were in work. They were the usual suspects. The most popular category was Indian Aunties. A category I also enjoyed.

I was called up to the CEO one morning. Her name was Shilpa Doodhwala and she was in her mid-forties. I only knew that she was married and she had children. Everyone seemed to fear her as she was stern. She was having trouble with her computer. I had never met her before and I was nervous. She was working on some papers and did not even look up at me and said matter of factly, "It is not working. You need to fix it. I have a lot of important information on there."

Most of the employees saved their information to the server but she had saved all her information on the computer. I tried a few simple tricks but it did not seem like a quick fix. I was scared to break the bad news, "I will need to take it down and figure out the problem. It seems to have contracted a virus. I have brought another computer to set up for you until yours is fixed."

She was dismissive and said, "I want daily updates on what is happening. Now leave."

She was arrogant and rude and it really made me angry. But I had only recently started and I could not afford to upset the boss.

I set her up and took the computer without a fuss. As I got down my manager, Ajay, greeted me and said, "Salman, this is a priority. I will have a look at it."

He took it off me to look at. I still felt resentment towards Shilpa but I tried to put it behind me and get back to work. It had been 3 days and I had not heard about Shilpa's computer and I thought no more about it.

It was the afternoon and Ajay called me into his office. He said, "I cannot figure this out and all I can think is to delete it and start again. But Shilpa will kill me and everyone in this department. Can you take it with you this weekend to figure it out? She has only given until Monday for it to be done."

Ajay was as inept as he was lazy but it was our jobs on the line, "I can take it with me tonight."

I was resigned to losing my weekend on this mission to fix the computer. Ajay had wasted 3 days and came up with nothing. Sometimes I wondered what he did all day.

I left it in my bedroom and tried not to think about it. I went to bed and I could not sleep thinking about the problem. Also having to fix the problem reminded me of Shilpa's rudeness which added to my anger at this imposition.

I ran some basic diagnostics on the computer and it showed multiple errors. I had to do a system wipe but Shilpa had given strict instructions not to do this. There was something about the errors that irked me. It reminded me of something but I couldn't put my finger on it.

It then hit me, I had the same virus a few years earlier from a porn website, MilkySluts.Com. I had to do a system clean on my computer but I was younger then and I had learned a lot more about getting rid of viruses since then. As I knew what the virus was, it did not take me long to find it and erase it. I had my weekend back but the way Shilpa talked to me really bothered me and I wondered what she had that was so important on her computer. I also wondered how she got the virus, could it be the same way that I did.

I was not going to sleep tonight. I was going through her files and there was a lot of work documents and they seemed important. I went through her internet history and that is where I made the real discovery.

She did get the virus from the same website. That took me by surprise. The website is for people with a lactation fetish. But as I went through her internet history I realised that website was not a one off. There were various other websites with the same fetish being explored. I just found it strange and wondered if someone had used the computer but I knew that was not possible as she was so protective over her privacy and no one would dare cross her. But as I looked further she regularly visited a dating website. The account was still logged in and I could not help myself.

She did not post a picture and it only used her first name. At the office everyone knew she was married and I found this really strange. I tried to think of innocent explanations but there was nothing innocent about these websites.

I went through her messages on the website that is where I learned a lot more. This was where I discovered that she was divorced. This was something that nobody at work knew about. She never seemed to reply to older men but she would engaged in chats with younger men. Some of the messages became explicit but they always seemed to end and she would move on to the next person.

I found it interesting, it seemed like she knew what she wanted. That resentment I had towards was turning into something else. I began to read her emails. This was gross violation of her privacy but an obsession was coming over me.

Her emails were fairly normal but then I found an email from her husband. It was dated 6 months earlier. I found it odd that her husband was sending an email in the age of text and calls and various other quicker forms of communication.

His email was odd. It started off in a normal tone but it soon spiralled. He was blaming her for choosing her work over her family but I found the ending lines strange, "We all know what you did with Summu. He was my nephew and only 20. Whore." It became clear that she had blocked him from other forms of communication and he was now blocked from her email.

I now knew her experience with younger men and I wondered if that is what triggered her fascination with younger men. I created a profile page on the dating website. I used an old college photo where I wore sunglasses and a hat. I used my normal details but made it clear I was into older women and used preferences I knew would appeal to her.

I could see the sun coming up and I could not believe that I had spent all night obsessed with Shilpa.

In the morning I was regretting creating that profile. I did not know what came over me. How could I be thinking of seducing my boss? I was inexperienced and I had never had a serious girlfriend. That weekend I prepared her computer to be returned on Monday. I installed the latest software so she would not have the same problem again.

On the Monday, I told Ajay that the computer was fixed. He was visibly relieved and said he would speak to Shilpa madam. He was obviously going to take credit for my hard work.

Ajay seemed impressed with my work and he was giving me more responsibility. I was pleased that my role was getting more challenging.

I had forgotten about the profile and by midweek I was more focused on work. But then I got an email saying someone wanted to connect with me on the dating website and it all came back to me.

The message read;

"Hi Salman. I found your profile appealing. I am hoping to connect and see if you appeal to me more. Love, Sexy Shilpa."

I could not believe it and I sank in my seat as I saw the message. I didn't accept it but then I didn't reject it. It was late and I was tossing and turning in bed. My brain was working overtime telling me to accept the request or it will look suspicious.

I convinced myself I had to accept the request. So I hit the acceptance button. I had to reply right away or that would be suspicious. But I thought I would go in hard to scare her off. I did not want this going any further. So I replied;

"Hello Sexy Shilpa. I am 21. I don't care about jobs or relationship status. If you cheat, that is your business. I don't play games so I am going to tell you my fantasy and you either get to the point of what you want or don't bother replying. I want an older woman. I find them incredibly sexy. I like curvy older women. I like them to have big tits. And if you want to know the truth, I want them to have milky tits that I can suck on them until they are dry."

She was online and I could see that she was typing a reply but then she stopped. She started again but then stopped. I read my message again and I thought to myself, if I am scaring her off then why am I basically describing her physically and then mentioning a fetish I know she has. It was fetish I have had for some time and I always found the idea of adult breastfeeding extremely erotic.

She then logged off without replying and I thought I had succeeded in scaring her off. But I had a tinge of disappointment at the thought.

It was almost midnight when my phone beeped to let me know I had a message on the dating app. I was half asleep but it soon had me fully awake;

"Ok Salman. You have my attention. If you have a lactation fetish then you have messaged the right person. I find a young man feeding on my breasts very arousing and I am still producing milk. It causes me many problems but I find it nurturing and sexually arousing."

I was in a horny state and this informed my reply;

"Yes I want to feed on your milky tits. But that is not my whole fantasy. I want to collar you and put nipple clamps on your tits. I want to control you. If you disobey me, I will spank your ass and tits until they are red. Do you want a master or are you wasting my time? I don't have time for the cock teases that waste their time on these sites."

I was trying to push her buttons. I did not want to be one of her other boys that she teased and then forgot about. She was either going to be repulsed by me or drawn to me. She did not seem to like the slow and soft approach from the other young men.

She again began to write something and then stopped. I seemed to have her rattled and she seemed unsure. It was different to how she was in the office where she was dismissive and arrogant.

She logged off again. If she did not reply to me, I would have dodged a bullet with my work. But if she did reply, I wondered how far I could take this?

I was sleeping when I heard my phone beep again. I woke up annoyed as it was the middle of the night. But then I saw that it was the app and I wondered what her reply could be, would she tell me to fuck off or would she be intrigued;

"You bastard. I am not a cock tease. Your fantasies are bad. You are a bad boy."

She couldn't sleep. She was probably fingering herself as she wrote the message. So I felt bolder than ever;

"How do I even know you are worthy of this bad boy? Send me a picture and don't be a cock tease."

It was getting under her skin calling her a cock tease and I had to push her buttons or she would get bored again. She sent a picture where she was wearing casual short dress. She looked hot but I had created a persona for this profile so I replied;

"Cock tease. Show me a real picture or don't waste my time. Cocktease."

I sent a picture of my cock to give her an idea of what I was looking for.

She didn't reply and I tried getting back to sleep thinking it was over. It was strange that I was taking on this persona as in reality I was a short fat nerd and I wore glasses but the way she talked to me in her office had brought out a new side to me.

She then replied after 20 minutes, "I am not a cocktease."

She then sent 2 pictures. One of her bra covered tits and panty covered pussy. The underwear was really pedestrian and I had to admit I was disappointed at her choice but excited by the pictures but that would not be enough for dating app Salman;

"Your panties and bra are boring. I have sent you links for what I want you to wear. If I ever agree to fuck you, make sure you wear something worthy of my attention."

Even I was impressed with my arrogant tone, it was so unlike me but I also wanted to put her in her place.

I went to sleep ignoring the app. I saw her message in the morning and it said;

"You are so ungrateful. I never do that for anyone."

It was true she had not done that for anyone before as I had been through her messages but if I softened now it would be over as she would lose interest.

I ignored her during the day. I then messaged her to say, "I will only reply to you if you send me a picture of bra and panties I have selected for you. Nothing else will do. I don't care about what you do for others. I am all that should matter for you."

I heard that she had left the office urgently on an errand. I carried on with my day as normal. As I was getting into bed that night, I received a message on the app.

She had sent a picture and I was excited. I had selected a bra and thong for her. The material was see through lace. It came in red and black.

She sent me a picture of her bra and panties from the front. I could not believe my luck but the persona kicked in and I replied;

"Take a picture of your ass and show me your thong or this is the last message you will ever receive."

She complied and sent a picture of her thong covered ass. I replied;

"You have pleased me today. Tell me how you masturbate? I want details."

She was typing as soon as I sent the message;

"Oh god. This is so hard. I usually play with my breasts. When I am horny my breasts produce a lot more milk and I start to play with them to release the tension. I like teasing them but as I get more turned I am rougher. I pinch and pull on my nipples. It turned me on when you said you would slap them. I then play with my pussy. I run circles around my clit but I then finger myself using two fingers to climax. I am self-conscious about my breasts. Can you send me a picture of your cock with your hand around it?"

I was not well endowed at 7" but it was thick and I could not fit my hand around it. I sent the picture and asked;

"Did you finger yourself last night? I want to abuse your tits. I want to play rough with them and spank them. Your body is a treasure that I want to plunder. You are stunning."

She replied;

"Yes I did. I have never been so attracted to someone before. I lost confidence in my body and I have been unable to show it to anyone in a long time. It was around 6 months ago, my confidence was low and my husband would not touch me. I had stopped breast feeding for a year but my breasts would not stop milking. My husband found it disgusting and he would not touch me. His nephew came to stay with us and he seemed to be fascinated with my breasts and I gave into temptation. My husband said he would not reveal my indiscretion if I gave up the children and I had no choice. I was never much of a wife or mother as I focused on my company. I am the CEO and I have a lot of responsibility."

It was a lot of information but I saw how she ended it. She wanted me to know her status but it was not going to make a difference;

"Your husband should have ravished your breasts every night. Your milk should not be going to waste. I want to treat you like the horny divorced slut you are. Show me your fingers in your horny divorced cunt."

Her reply took my breath away. She sent a picture of her thong pushed to the side and two fingers inside her cunt. I could only imagine how horny she was.

She replied;

"I have searched so long for someone that shares this fetish. I want to see you."

My nerves came back and I did not know how to reply. I was confident playing this dominant persona online but what would she think if she saw a fat chubby nerd.

I had to prolong this online interaction;

"You will in time."

My other problem was keeping her interest. I had seen she often grew bored of men and I needed to do something to keep her attention.

The next day I had an idea to give her something closer to meeting but also allow me to keep my mystery.

I sent her a package. I could not let her know I was one of her employees so I had it delivered. It was carefully wrapped to hide the contents. I left a note that read, "There is only one Shilpa that is a CEO in Delhi x."

I was not sure about acknowledging her status as this may bring out her arrogance but I also wanted her to know that I was not bothered by her status.

I then sent her a message on the app;

"Wear that for me under your CEO power suit. You may be a CEO to the world but underneath those clothes you are a horny divorced slut for my cock."

I sent her a pair of nipple clamps. I saw her walk into the office as I arrived early. After I had sent the message I did a walk of the office checking for IT problems. As I was walking past her office, I saw her draw the blinds and I knew she would be trying out the nipple clamps.

An hour later she sent me a message, "I am wearing them."

I tried to catch a glimpse of her to see her squirm with the clamps but she did not leave the office and her blinds were still closed. I then sent her a message, "Send me a picture of your clamped udders."

I wanted to degrade her and remind her that to me she was just a milk titted slut. I eagerly anticipated the picture. She sent it after a few minutes with the message, "They are swollen like never before."

They looked enormous and I could feel the saliva build in my mouth. I wanted to barge into her office and attack her tits right then but I had to pick the right moment.

I replied back, "Good Slut. You have pleased me. You must wear them until I order you to take them off."

It was late into the evening and everyone had left the office. Shilpa had not left her office.

She then messaged me, "I need to milk them. They hurt too much. I need to milk them now."

I replied, "Milk your udders now. Finger yourself while you milk them."

I crept to just outside her office. I was completely obsesses with her. I could hear the breast pump whirring my mind was stirring. I wanted to interrupt her and suckle her breasts but I was unable to take that step. My real life personality was nothing like my online personality.

I could hear soft moans over the whirring. She was masturbating while milk those beautiful breasts. I was getting aroused as I heard her moans becoming louder.

My cock was so hard and with my ear perched against the door I unzipped my trousers and pulled out my cock from the slip in my boxers. I was so hard and I could feel my precum around the tip of my cock.

I began to gently stroke my cock slowly building up a rhythm to match her moans. As her moans became more pronounced my stroking became faster.

I then heard her moan, "Salmannnnnn", as she came loudly. I could not control myself and I shot cum all over the floor outside her office. I let out a groan and all of a sudden I heard her stop and I could hear her scramble. I quickly tried to clean up my mess and left hastily.

***

Shilpa

It was so risky doing what I did at work and when I heard the sound from outside of my office I panicked in fear of being found in such a depraved state.

I had breast pumps attached to my nipples. My tights and panties were down with my skirt hitched up and I was fingering myself with two fingers. I could not let an employee find me behaving so wantonly.

I quickly arranged my clothing and went outside of my office. But there was no one there but there was a distinct smell. I was certain it was semen but I was in a horny state and I was not sure it was just my mind playing tricks on me.

As I was trying to sleep I kept thinking about Salman. I looked at his pictures and something about him seemed familiar. It was almost as if I knew him from somewhere.

There was also something else about what he said about there not being many CEO's in Delhi named Shilpa. I did a google search and found at least 10.

There had to be another way he knew who I was. A nagging thought kept coming to me, "Was he one of my employees?"