First Time Sex With My Longtime Bestie

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Hi everyone Akshay here, age 23 from Chennai. I’m a reader of ISS for the past 5 years, and it’s high time I shared my experience. This happened a couple of months back. It was with my longtime bestie. Her name is Vaishali.

We know each other for around 6 years, starting from our college days. She lives half an hour away from my place. I’m pretty familiar with her parents. We got to know each other from our college days as we were from the same department.

She had a sexy shape, which gave me a boner many times while talking to her. We both were in a relationship in our college days, that ended right at the final year. Due to the breakup and end of college, we were a bit apart but still in touch.

Incidentally, we started work at the same company, which further brought us close. She used to dress up sexily for work. I’ve many times seem her cleavage without her noticing. We both share all our secrets, including the people we flirt with and have naughty chats with.

Once I had to travel to another city for work, and she started missing me. We were used to being with each other many times. As soon as I returned, she immediately suggested to go out as it was a long time. I too missed her, and so we decided to go to a mall and a nice restaurant.

When we were in the mall, she gave me her purse and mobile to go to the washroom. I opened her mobile to find out who she was flirting with recently. (We both know each other’s passwords) to my surprise, she was flirting with a guy from our college.

They were sexting. I immediately got a hard-on as I always thought her as a pretty reserved girl. When I further scrolled up, I found out that they went to a pub and made out. I was furious after reading all that. She never spoke anything regarding that and also the fact that guy got to kiss her.

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I immediately shouted at her when she came back from the restroom and left the place. That night, she texted me and started apologizing. Slowly my anger reduced, and I asked her how it happened. That’s when she explained how they casually went out.

He started making moves on her, and she just went with the flow. Hearing how they started with kissing and he played with her boobs gave me a hard-on. Then she again apologized and asked to catch up for a movie the next day. I agreed, and we met the next day at the same mall.

She was dressed up more sexily than yesterday. I was continuously staring at her boobs. (She had 34C boobs.) Once the movie started, we were holding hands and watching the movie (We hold hands most of the time). This time I planned to make a move.

I slowly put my hand over her shoulder. She leaned on me, showing her cleavage again. I slowly placed my arms near her boobs and started caressing her. She understood what I was up to and directly asked me to take my handoff. I was pretty disappointed, and I started watching the movie.

She again leaned on me. I was having a tough time seeing her cleavage. She saw that and with a mischievous smile said, “You can look at them, but don’t touch them.” That was the green signal for me. I said it’s too hard for me to control, and I asked for a kiss.

She said nothing, and so I made a move and started kissing on her cheeks. Slowly we were in a passionate liplock. I slowly kept my hands on boobs again. She again stopped me. But this time I bit her neck and she was too horny to stop me.

I directly took my hands inside her T-shirt and started playing with her boobs over her bra. They were so soft, and her nipples were so hard. She was enjoying me playing with her boobs. I was continuously playing with it and whispering in her ear how soft and sexy they were.

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She was biting my ears and neck in the mood. Slowly I took her hand and placed it on my hard cock( I have thick 6-inch meat). She just held it tightly over my jean and continued to kiss me. I asked her to play with my cock, and she obliged.

She unzipped me and took my cock out, and kept playing with it for some time. I asked her for a blowjob. But she refused to say this is her first time playing with a cock. We continued our foreplay till the intermission. During the break, I went to the washroom.

I made my mind to make the most of the situation somehow now. I went back in and again started with her boobs. But this time, I moved my hands down to her pussy. She was wearing a red color panty. I just placed my hand over her pussy, which got her shivering.

I slowly started to caress her pussy lips over her panty. It was too wet by now with all our foreplay. I whispered in her ears that I want to kiss her vertical lips, to which she said not here. I was a bit disappointed but continued to play with her pussy and tried inserting my finger.

She started moaning, and I had to kiss her to stop her from being heard by others nearby. I continued fingering her and playing with her boobs and biting her lips. We continued our foreplay until the movie ended. We adjusted ourselves and left for our home.

That night she texted me, asking whether I was happy. I replied, “Our happiness has just started. Get ready for more such sex adventures.” She immediately called and said I was such a horny guy. I replied to her, “You are too. I saw how wet your panty was.”

She laughed and said, “All because of your thick cock. I’ve never played with one before.” Slowly we started getting in the mood. I was describing how soft her body was and how I’m going to squeeze and enjoy her the next time I get a chance. She said she was waiting for it.

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I somehow convinced her of a video call. She called me only to catch me naked, playing with cock. She was shocked as this was the first time she was seeing me like this. But I convinced her saying she already played with my cock in the afternoon. She, too, agreed.

Slowly I convinced her to strip and show me her nude body. By this time, she was fully horny, and she agreed to everything I asked. We had an intense video call for around 40 minutes, and we both released our load. She was all blushing after the session, and she said she wants to enjoy the real taste of sex soon.

I promised to show her heaven, and we decided to meet soon and have fun. We both were waiting for a chance to get some alone time and space so that we can explore each other, and that’s when the eventful day came.

That’s the first part of the story, guys and girls. This is my first story here and sorry if I had dragged it too much or missed out on any details. Please do respond with your feedback to [email protected] or ping me in hangouts. The second part will be uploaded based on your feedback. Thank you!

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