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An Entrepreneur’s Cuckold Story – Part 1

⏰ 18 min read

Hi guys,

I am Ramu, a 32-year-old guy from Bangalore. This story started four years ago when I was 29. As you all know, Bangalore is a startup hub, and there are many hot girls and guys there.

I had a good revenue-making software startup for my age and background. I was making a really good amount of money. My company was listed as a unicorn in a very short amount of time with a net worth of around 30 million US dollars.

I had so many side businesses, and all in total, I used to earn one crore per month. So I had a good house and car. My family was well-to-do in the hometown in north India, so they used to never visit me at all.

For my richness, any girl would fall for me, but I needed a bit of a sanskari girl for marrying, and I did not want to create any affairs at that age.

Then, I went to one of my friend’s parties where I met the beautiful girl, Roopa. She was so sexy and had thick hair till her shoulders, good round boobs, dark eyes, and was fair in color.

She was not that involved in drinking like what others were doing, so I approached her and spoke for a bit. I understood that she had a breakup very recently and she was a bit depressed.

Once she was comfortable with me, she started drinking, and then she was all over me. To be fair, looks-wise, I am not at all fit for her. Then, her friends took her home, and it ended there.

The following day, she texted me, and our love started from there. But we were never physical before marriage as she insisted not to go far before marriage, which I liked then. So our love continued for one year.

When I was 30, my family forced me to get married, so I introduced her to my family, and she introduced me to her family. Then finally, both of our parents agreed as both families were okay with each other, and we both got married. During our marriage, I was 30, and she was 26.

After our marriage, during the first night, we both saw each other’s bodies for the first time. She was milky white in color, and her hair was silky smooth. She had soft lips, and her navel was too good to resist from kissing.

She had a neatly shaved pussy and round hanging boobs with light brown nipples ready to pop out from her bra. On the other side, I was a bit dark in color, chubby a bit, with a small dick.

At first, she was excited for the first night, and then when I was undressed, her excitement reduced. After our first round of sex, she told me this is the smallest penis she has ever seen and the smallest amount of time someone has fucked her.

I was in shock to hear that. So I asked, “How many guys have you been with before?”

She replied calmly that she had three exes. She had mentioned to me about that before. I thought she was not physical with them as she was not with me. She told me they had a bit bigger dicks, not the biggest as in porn, so I was relieved.

But they used to fuck her for at least 10 to 15 minutes before they came, whereas I came in two minutes. I was tired. So she just consoled me and told me not to worry if it happens the first time. She said, “Let’s try another time.”

This continued for almost five months. I was unable to perform, and she was willingly okay with that and encouraged me to go to the gym and increase my performance and all.

On our sixth month anniversary, when we were having sex, she was frustrated a lot and told me it has been one and a half years that she did not have proper sex. She said, “If you are unable to satisfy me, just throw the divorce papers and leave me with half of your property. I will get as many studs as I want to satisfy me.”

After listening to that, I was in shock. Then I pleaded with her and apologized to her for not satisfying her. I requested her that I will listen to whatever solution she is okay with for this problem other than divorce.

So she cooled down a bit, took a deep breath, and she replied that from now on, as soon as I enter the house, I will listen to her and be like her slave. I was relieved after listening to her.

Then that night, she told me from now on I will please her using my tongue. Till then, she never asked me to give her oral. Then she made me lick her feet and all. For some reason, I felt good.

I was her slave for the next three months. But to be fair, she did not exploit me being a slave in terms of expenditure and all. She simply used to keep her legs on me at home, kick me sometimes in a loving way, make me sit near her feet, lick her feet, and pleasure her through licking her pussy. That is it.

And for some reason, I felt that was really good. Then I confessed to her, “I am liking the way our relationship is currently.”

She replied, “See? I am your boss.”

And I may be a good boss, but internally, I need someone to control me. That is lacking in my real life, which she is doing here, so I am liking it.

I had a very bad habit of watching porn when I am alone. I used to watch at least 30 minutes a day. Usually, I used to watch straight normal porn, and I used to get aroused. One day, I searched for master-slave porn as me and my wife were in such dynamics, and I used to enjoy it a lot.

For almost two months, I used to watch only the master-slave porn category. One day, in the suggestions, I got cuckold porn, and I watched it. Then, I researched about it, which aroused me so much.

The thought of seeing my wife fucked by another man in front of the husband fascinated me. This is one part, and cuckold humiliation was another thing I enjoyed more.

Watching the cuckold humiliation porn and reading the sex stories was a feast for me. I even developed the fantasy of sucking men’s cocks for my wife, which addicted me to the cuckold fantasy.

Then, I got the thought that I have a bit of an ideal situation to try this in real life, but I was not sure how Roopa would react.

All these things were there in my mind. Just then, one incident happened in my professional life. Our company needed an investor to support in some technology we were building.

So, when we were in search of the investor, I met Ben from England. He is a 38-year-old unmarried hot gym hunk with alpha male energy. He is an investor in the UK already and had invested in a company in the UK with similar technology research.

So, when we approached him, he was kind enough to accept our offer. He scheduled a tour to India for 10 days to check on the accounts in the company and the R&D work, then to meet all directors, investors, and staff.

Ben came to India in the month of January 2023. Our office was not that large, so he shared a cabin with me. Within three days of his visit, he was convinced by the offer and ready to invest in the company.

So, to have a small party, I organized a party for directors, investors, and their families and Ben. Everyone arrived there, including my wife. She was looking stunning in a black one-piece dress with subtle makeup.

Ben’s eyes were on her only all the time. Then I introduced her to him. He hesitated a bit and shook hands with her. I went to attend other guests. Even Ben was with others as he was the center of attraction of the party since he is the investor. Everyone was talking to him.

After all the celebrations, only a few people were left. Then, Ben started talking to Roopa generally. I was busy with arrangements and bill settlements. They almost spoke for 30 minutes that day.

The party ended, and Ben stayed in the same hotel, so he returned there. Me and Roopa were driving back home, so then I asked her what she felt about Ben. She told me she got intimidated by him after so many days.

Some man intimidated her. He looks like a hot macho stud. She guessed he has a thick tool inside. So I was on cloud nine when I heard that. I asked her if she would be okay if he fucks her.

She replied, “What the fuck are you talking about? He is a great man, but I don’t know how I could sleep with him.”

Also Read: The Perfect Start With A Stranger

So by her reply, I got to know that she is okay if he fucks her also but not ready for the cuckold fantasy. The next day when I went to the office, in my cabin when only me and Ben were there, he asked me about my wife and how we met and all.

Then, I asked him what they spoke about that long yesterday. He just replied it was just normal conversation. Then he told me, “Your wife is too hot, man.”

Then it confirmed me he is also intimidated by her. So I just told him even she felt the same thing about him. He was in shock and asked, “Really? What did she say?”

Then I confessed to him that I cannot satisfy her and told him about our personal life but not about cuckold, slave, or humiliation. I just told him I would be fine if someone satisfied her sexually.

So, he asked me if I would be fine if he satisfied her. I replied gently that I would be more than happy if he is the guy satisfying Roopa.

He thanked me, and then we started planning how to begin and get her into our plan. He suggested that I invite him for dinner. He will take over from there. I was overjoyed by hearing that.

Then casually, I called Roopa and informed her, “Ben is coming for dinner, so please prepare good food for Ben and us.”

That day I left the office early, went home, and arranged for dinner. I asked Roopa to get ready nicely to give a good impression.

After she got ready, I was stunned by looking at her. She wore a translucent black saree where her navel could be easily seen. The blouse was a bit deep and backless where we could see her cleavage easily. Which was enough to make any man mad at her.

Around 8 PM, I booked a cab from the hotel to our home for Ben. He reached our home by 8:30. On the way, he picked some flowers for my wife. As soon as he came, I saw his look, and I fell for him by looking at his hotness.

He was in a light brown formal shirt and brown formal pants with flowers in his hand. He complimented my wife by telling her she looks damn hot and gave her flowers. Then me and Ben were casually talking, and Roopa invited us for dinner.

We both went and sat for dinner. She started serving. All the time, Ben was staring at her. She made roti, paneer, and fried rice. We are vegetarians, so the usual menu was there.

All the time when she used to serve rotis, he used to stare at her cleavage and try to peep inside. Sometimes he even tried kissing her on the cheek, and she did not react or resist.

Then, my dinner was done. Ben was still eating, so I told Roopa to sit and eat. I will make rotis now. She was fine and sat beside Ben and started eating. Ben started a conversation like, “So, do you like me?”

She replied, “Yes, I like you, but that’s it. I don’t want to do anything with you. You are hot though.”

He asked, “Okay, why don’t you want to do anything with me?”

She replied, “I am married. If I was single, for sure I would have had an affair with you.”

For that, Ben told her, “Forget Ramu for a moment. Do you want to have fun with me?”

She told him in that situation, for sure yes. He replied that she was his girl, then squeezed her boob and kissed her cheek properly.

She asked, “What are you doing?”

He gently said, “Nothing. I just wanted to know your feelings about me, naughty girl.”

They just smiled and finished dinner. Then Ben left and just hinted to me that it was set.

I asked Roopa what they were talking about. She told me in a dominating tone, “Why do you want to know?”

I kept quiet. She asked me for oral that day, and she squirted thrice on my face. So I thought it was a green signal for whatever I was thinking.

The next day, when I went to the office, Ben told me everything in detail and asked me if any special occasion was coming nearby for us.

Then, I told him her birthday is the day after tomorrow. He asked if I would like him to gift her on her birthday. I was very happy listening to that, and we made a solid plan for her birthday.

Days passed, and all the arrangements were made for her birthday. I bought her a Gucci bag as her gift. So I thought, “Let Ben give her that. I will hand the bag to Ben in the morning so he can give it to her.”

The party was called for 6:30 PM. Only our close friends, colleagues, and Ben were invited to the party. She wore a sexy shirt and jeans. Everyone gave her gifts, and she asked me for her gift.

I told her it is very special and waiting in the house. Ben handed a bouquet of flowers in front of everyone and told her he has some personal problem and left.

The party was over at 8, and everyone started leaving by 8:30. We settled up the bill and started leaving for the house. It was just a 20-minute drive to our home, and she was dominantly asking me what the gift was.

I did not reply to her. Then we reached home and opened the door. Nothing was there.

[A small flashback from when Ben visited for dinner. I gave him the home tour, so he knows our home structure roughly. The ground floor has our dining, kitchen, and guest bedroom. The first floor has one master bedroom and a guest bedroom. We planned everything in the master bedroom, and I only gave Ben my home keys to go and plan according to him.]

I closed her eyes with my hand, locked the door, and took her to the first floor and opened the master bedroom door. I was shocked to see what was there. Ben was lying in his underwear.

To describe Ben, he is a 6.2 feet tall hunk with a muscular body, hairy, and pure British color. The first time I saw Ben in that attire, I was flattered. The whole room had rose petals.

His clothes were removed and thrown in a specific way to make it cozy. On the ground, white sheets were spread on the bed with a red heart made of rose petals, and a Gucci bag was beside him. The lights were dim to make it cozy.

I gently removed my hand from her eyes. She was shocked and was not ready to process what she was seeing. She went from excitement to shock in a minute seeing Ben in such a way. Then she turned towards me and asked, “What is this?”

I replied, “This is for you to enjoy what you are not getting from me.”

She exclaimed, “Really?”

Then I replied, “Yes dear… I am not going to judge you based on this any day. Please enjoy as you wish and be happy tonight and be completely satisfied.”

She hugged me and told me, “This is the best birthday gift.” This confirmed Ben that she is his property for the night.

He got up from the bed and came towards us when we were hugging. He took her from me and told her, “Hey, from now on till tomorrow 7 AM, there is no Ramu in your life. There is only one man, and that is Ben. You will be completely mine till morning.”

Saying that, he removed our engagement ring from her hand and kept it aside. He removed her mangalsutra and gave both of them to me and told me to keep them with me till tomorrow. He said, “Now, she is not your wife. She is mine till tomorrow.”

He took her to the bed, made her sit, and gave her the bag I bought. She got so excited and kissed him left and right. She told Ben he is the best. He told her, “This bag will be there with you forever, but I will be there till tomorrow morning, so let’s start to make love, hottie.”

She gave a smile and kissed him on the lips, which changed into a lip lock for a solid two minutes. Then Ben jumped onto the bed with her and placed Roopa’s hand inside his boxer.

That time, my wife looked towards me with an uncomfortable look. He asked Roopa if my presence is distracting her or making her uncomfortable. In a very slow voice, she nodded, “Yes.”

So he came near me, pushed me out of the door, and gave me an empty bottle. He told me, “You don’t exist till tomorrow morning. Fill water fast and give it to us, and don’t dare enter this room till tomorrow 7 AM.”

He said it in a very dominating voice. I did what he told me. I just went down, filled the bottle, and went upstairs and opened the door. By then, Roopa was rubbing his dick inside his underwear happily, and Ben was continuously kissing her on her face at different places.

Then in action, he told me to get out of the room. So I closed the door, left a small crack so I could see, and then went outside. I started peeping from the door crack and keyhole. I could see full action, though not with clarity, but still it was manageable.

First, he stopped kissing and removed Roopa’s top. That made him mad as he saw the cleavage. He went over it wild and played with her boobs over her bra for a solid five minutes. Then he removed her pants. She was in her bra and panties, and he was just in his underwear.

He went on top of her, hugged her tight, and started lip locking. They exchanged juices for three to four minutes. Then Ben started to put his hands inside her panty and started fingering her pussy. She was going mad by that and started biting his lips in that horniness.

Then he stopped fingering her and removed her bra. After seeing those white milky boobs with light brown nipples, he went wild on them and started biting them. That made her wild, and she was unable to resist him. He was going wild on her.

Then she pushed him, and both of them caught their breath and laughed about their situation. Then there was small smooching in between, and then he removed her panty. She was clean shaved. He started licking and biting her pussy.

She squirted once, then she caught her breath slowly. Roopa then made Ben sleep properly and removed his underwear and started giving him a blowjob. She sucked him for a solid 10 minutes, but there were no signs of cumming.

Then she was tired. By seeing her condition, Ben asked, “Shall I fuck you now?”

She replied, “Yes honey… waiting for that.”

He took the condom which he brought, and Roopa put that on his dick gently and kissed it once.

He got up from the bed, and then she took the doggy position. He fucked her for a solid 10 minutes. Still, there were no signs of cumming. On the other hand, Roopa was completely exhausted, but Ben was completely filled with energy.

Then he changed the position to missionary and fucked her for another 15 minutes, and finally he came and collapsed. Then both faced each other and kissed like teenage lovers and were cuddling. I heard Ben saying, “I love you, darling.”

Then both were talking. I could not hear properly, so I went to sleep as I was tired from staying in an uncomfortable position for a long time.

*****

In the next part, you will know what they spoke and what Roopa and Ben discussed and how I became the cuckold slave.

Thank you for reading!

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