Roommate’s girlfriend: A forbidden fantasy realized

I am Abby, a 23-year-old guy. I am originally from Chennai, but I studied Engineering in Mumbai. I used to live in a hostel with a roommate. That guy’s name is Prajwal. This is an incident that happened a year ago with Prajwal and his girlfriend, Anisa.

When I first joined college as an 18-year-old, I was quite innocent. I come from a conservative household, and I did not really have much privacy in my home. So, I had never watched porn or masturbated. I was waiting to go to college to enjoy the newfound independence.

We all have that one friend in college who introduces us to all the dirty things. For me, that was my roommate, Prajwal. He was a very charming guy with an amazing sense of humour. He always used to crack double-meaning jokes, which everyone liked.

We loved talking to each other, and we became good friends. One day, I was sleeping in my room when he was not there. He came and knocked on the door. It took me a while to open the door. He started making fun of this, asking, “ You were jerking off, weren’t you?”

After this day, we frequently used to have conversations around sex, masturbation, our crushes and so on. He even used to send me good porn videos to watch. He opened a whole new world to me where I could not just consume this kind of content, but could also talk about it in a fun way with someone.

I started enjoying spending time with him. Over time, we lost all filters in our conversations and could tell anything to each other. We even had conversations where he would tell me how to increase the pleasure when I was masturbating. I used to call him my ‘sex guru’.

Just after a few months into college, he started dating a girl from our senior batch. Her name was Anisa. God, she was gorgeous! She had huge boobs and used to wear very short skirts that showed her seducing thighs. All the guys used to check her out all the time.

My roommate Prajwal was lucky to have her as a girlfriend. Sometimes we three used to hang out together as I was his closest friend. Over some time, I grew comfortable around Anisa as well. So, the dirty conversations Prajwal and I used to have started to happen even when she was present.

Our dynamics were set in such a way that Prajwal used to come and share about his sex life with me. He would describe what he and his girlfriend did and what new things they are trying, in all details. He was excited to talk about it to someone.

I also started making jokes about their sex life, sometimes even when Anisa was there. This became common for us. We all felt extremely close and comfortable to talk openly like this.

While I enjoyed the conversations and was happy for my friend, I also felt envious of his sex life as he was hooking up so frequently with someone so hot. I used to jerk off thinking about his girlfriend.

Sometimes, I used to feel bad about thinking of my close friend’s girlfriend in this way, but I couldn’t help it. I had no idea what was coming next.

One day, Prajwal came to me and said he wanted to talk about something important and sensitive. We went on a walk in the park on our campus.

Prajwal: How do you find my girlfriend?

Me: What do you mean?

Prajwal: You are always checking her out. I have noticed it many times.

Me: Sorry, yaar. I’m really sorry. Yes, I’m not going to deny that. I could not control myself, even though I tried.

Prajwal: Oh, you find her so irresistible?

Me: Well, I don’t know what to say to that.

At this point, I got super worried. I thought I lost a close friend due to my poor self-control. Seeing me visibly worried, Prajwal started laughing.

Prajwal: Dude, chill. I am not angry with you at all. I feel nice about the fact that my girlfriend is so hot that guys find her irresistible.

I didn’t say anything. I was confused about where the conversation was going. I looked at him expecting him to continue what he was saying.

Prajwal: Okay, let’s talk this out openly. You are such a close friend. What is the need to beat around the bush? I have a perfect plan that’s a win-win for everyone. So, you find my girlfriend hot and obviously would love to sleep with her. I also fantasize about seeing my girlfriend enjoy sex with someone. So, why don’t you two fuck each other while I watch?

Me: What!? Let me process this. Are you saying you like to watch your girlfriend being fucked by someone else other than you? What kind of a fantasy is that?

Prajwal: Well, you know it’s like this. You watch porn to look at people having sex, right? You would love to watch porn of someone you find very hot, right? That’s why we all have our favourite pornstars. Obviously, Anisa is someone I find the most attractive. So, I fantasize about watching her enjoy sex. Who better to try this with other than my closest friend, whom I can trust?

Me: Wow, I never thought of it that way. Anyway, this sounds like a plan! But what about Anisa? Will she agree?

Prajwal: In fact, she is the one who suggested this.

Me: WTF? I can’t believe this. I am nowhere close to being as attractive as you. Why would she desire me?

Prajwal: Come on, dude, you are not unattractive. But there’s another angle to this. So, I told Anisa about how I used to send you porn videos and how I taught you how to jerk off and all that. I also told her that you used to call me your sex guru. That somehow turned her on.

Prajwal:  She said that she finds it hot that her boyfriend has such a reputation with his close friend. So, she wants me to teach someone sex, and she wants to watch that. She told me this, and that’s when we came up with this. You are a virgin with no experience. And you were the one who called me a sex guru.

Prajwal: So, isn’t it best to teach you sex instead of anyone else? Till now, I taught you how to jerk off. Now, I will teach you how to pleasure a woman. You need to listen to me and make sure my girlfriend has a great time. You will love it. She is supremely talented in bed. Do you see how this is a win-win situation for everyone involved?

Me: I still can’t believe this is happening.

Prajwal: It’s not just happening. It’s happening pretty soon. I told you that Anisa and I are going to Lonavala for the long weekend, right? We are leaving tomorrow. You should join us. We will have 3 days of great time filled with pleasure. We should fuck at least twice every day, lol.

Wait for the next part to know what happened on the trip. This experience revealed the bisexual part of me that I was not really aware of. We had the most memorable sex of our lives in those three days.