Unexpected sex with best friend Sifali

Hey everyone, thank you for selecting my story for your session with imagination. Make sure you have your tools and wipes ready, and pants down, ladies and gentlemen. Let’s make you cum.

This is my first story at ISS. I have been waiting to write a story for a few years. My life wasn’t very spicy until recently when a girl whom I never expected or imagined to be next to me when I wake up, entered my life. Let’s get started.

My name is Sasi, just a typical average guy with a medium belly, healthy enough to satisfy any woman. Her name was Sifali. She had the perfect sex doll figure for any guy, with stats of 32C-28-30. All her beauty used to be covered with a hijab. Yes, she was a conservative, god-loving girl, who had been told to show her body only to her husband. I had seen her probably twice, once naked and once in a costume, despite knowing her for 5 years.

Coming back to the story, I never had feelings or sexual attraction towards her, although we discussed those topics. We both did our undergraduate studies together and got jobs in the same company, which was not planned but happened anyway. Most of the time we spent together, she either covered her full body or only her hair. Her parents had planned her wedding, which was in 6 months.

Everything was going smoothly until I had a huge breakup with my girlfriend, with whom I had been in a relationship for 6 long years. It was a devastating time. My best friend Sifali was there for me, managing her wedding preparations and taking care of me because she knew how deeply hurt I was.

One fine day, it was the rainy season in Chennai. I usually dropped her at a bus stop 2 km from my office, where she took a bus to her PG, which was some 20 km away. We lived in opposite directions. But that particular day, she asked me to drop her at her PG. I informed my home that I would be coming late.

There was huge traffic due to the rain. We started talking about various topics. She asked me how my sex life was with my ex. I told her it was okay; we used to have sex at least once a week. Then she said, “You know I am a virgin, right?” I laughed because I knew she was a virgin, but her pussy had regular action now and then from the toys she owned. This kind of conversation was normal for us.

She then told me she wanted to lose her virginity before marriage, and I said she should call her fiancé, go out somewhere, and have sex. Then our conversation shifted to planning that day. Still stuck in traffic, some 10 km away from her home, she surprised me by saying, “I know I am going to spend the rest of my life with him and have a lot of sex and kids. But before that, I want to experience how it really feels with another guy, with a real dick.”

I thought about it for some time and told her she could always book a guy online and plan it accordingly. Then she said something shocking, “We can’t be friends after my marriage as I am moving to Canada with my husband. Let’s finish our friendship here and start a sexual relationship.”

It was a valid question, but before answering her, we reached her PG. I dropped my best friend off without saying a word, started my car, took a U-turn, and stopped to smoke and think about it. It seemed like a valid idea. I called her and said, “Okay.”

She told me to book a room immediately. I called home and said I wouldn’t be coming. I booked a beach-facing room just 5 km from her place for two days, as the next two days were the weekend.

Sifali packed her bag, I picked her up and kissed her on her lips, which was our first kiss. Meanwhile, she was wearing a kurti with jeans and a hijab. We drove towards the resort. She was stroking my dick on our way.

We reached the resort, got the room keys, and she gave me a blowjob in the parking lot, which was empty. I asked her if it was okay to record us, and she said yes, but she asked me to be careful with the video (email me if anybody wants the video; her face is clearly covered).

I placed my camera in a good spot to record. We had a long kiss, and while kissing, I removed her hijab and saw her hair for the first time, which was a beauty in itself. We removed each other’s clothes, standing there with just her inners and me in boxers with my thambi struggling inside.

We kissed for some time and meanwhile, my soon-to-be-married friend had her hand on my dick, and my hand was on her ass and back. I sensually removed her bra, which was front-opening (which I like and even she knows that). Inside, I saw a beauty that will remain in my eyes forever – the most beautiful thing I had ever seen. I had seen my share of breasts but had never been mesmerized by such beauty.

Sifali started laughing, seeing me drooling, and took my hand, placing it on those beauties which were gentle stress toys for the next hour of our session.

She then knelt down, removed my shorts, and started stroking my dick. It was almost at its full capacity but still needed some work, which she did beautifully with her silky lips and smooth hands while maintaining eye contact (just imagine how hot that would be). This made me cum for the second time in the last hour.

Then I lifted her, and we locked eyes. She went to wash the cum off her mouth, came out of the washroom, and we kissed. I threw her on the bed, removed her wet panties, and slowly kissed her from her mouth to her neck to her boobs, where I took some time, then to her belly button, where I teased her for a while. Meanwhile, she couldn’t control her moans and pushed me towards her pussy, which was clean-shaven.

Slowly, I put a finger in my friend’s pussy, kept my tongue on it, and started licking her. I found her G-spot and started circling it while licking at the same time. She pushed me further down her pussy with her hand and made me lick her deep and deeper. She came after about 10 minutes of vigorous licking, which is a good time for a virgin.

Then we lay next to each other, catching our breath. Meanwhile, food arrived, which is essential for good sex.

Then Sifali helped me get back with a tiny blowjob, and during all this, we forgot to use a condom. We ordered one through Dunzo, which took over 20 minutes. I ran over to the parking lot to get the pack, and then we continued our session in the missionary position, where she locked her legs around me. She was a virgin but she did not have the blood if that is what you guys are thinking because she had broken her hymen with her dildo sessions.

We tried different positions for the next 30 minutes. She came again, and I came on her boobs. We slept alongside each other as it was almost 12:30 am.

In the morning, my friend ordered breakfast while I was sleeping and woke me up with a blowjob. Then we had breakfast and continued our session. We had similar sessions for the next three months. We stopped having sex just a month before her wedding because a guy can easily recognize if a girl is having regular sex or not.

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Thank you again for reading. Let me know your views and comments/share your experiences with me at [email protected]

(I am bisexual, so guys who want to share experiences can email me. You know what I mean.)

Feel free to reach out.