A Nostalgic Yahoo Messenger Chat Sex Story

Hi guys, it is been some time I have been reading stories on ISS. Here is my first attempt to write one on my experiences.

About me, I am 36 years old, work in an IT firm, married and looking for discrete NSA fun. I found it relatively safe to chat on the internet and make new friends, exchange views and have fun in general. It was like another dimension for me. Here I could make new friends and we could say anything without being judged.

I met many good friends online. Of course, there were times when you are looking for sex online. It was 2001. I was around 21 years of age. I used to chat in different chat rooms, perving around at times and participating in serious discussions. In one such time when I was home for vacation (from the hostel), I met a girl in one of the chat rooms and we started chatting and went our ways.

In the night when I was online again, it was a coincidence we were in the same chat room. She said her name was Jenny and after chatting for a while, we added each other on Yahoo messenger. Our times to come online aligned and we would chat online and leave offline messages.

Then I had to go back to the hostel in a few weeks. But in these weeks, we had become good friends. Very strangely, we exchanged landline numbers and used to talk a bit over the phone sometimes. But it was online chats most of the time.

We were very open and shared very small things with each other. While in the hostel, I was fortunate to have internet in the college lab and we had this thing where we used to type out long replies and so did she. In those emails, we would tell about what happened in the day and all minor things that happened.

Next time when I was home, we started chatting a lot. There were many instances where we were chatting till 6 am in the morning and didn’t realize we had burned the entire night together.

We decided we should meet one day. We had never exchanged pictures as I didn’t have any online at that time. Then we talked over the phone and decided the time and place.

After some days, we met up near the McDonald’s in CST, Mumbai. It was funny, I had not seen her and she had not seen me.

I saw a few people waiting and walking around. Then I thought it was going to be difficult to actually approach a stranger and as if she was Jenny. So instead, when I saw a girl standing, I stopped and asked one of the guys passing by to check if this was the only Mcdonald’s near CST station. That prompted her and we looked at each other and said each other’s name at the same time.

From there we started walking and talking pretty much all through CST to cuff parade where she used to live. It was a shocker as that was one of the richer areas.

While talking, I found out that they were staying there temporarily as her dad was posted in Mumbai for his job. We walked up to her place, waited a few minutes for her parents leave and then entered her apartment. We talked a lot there. When showed me a photo album, we decided we both should try slow dancing.

She put on some music and we were a little conscious of touching each other. We held hands for the first time. She knew that there was another girl (a school friend that I was interested in and all). She had a boyfriend whom she had lost connect with as they moved to another city. We were just moving around a bit, holding hands.

Then she put her hands on my shoulders and I held her waist. We were enjoying the music and looking at each other. We were not talking as much now but were standing closer.

The next song was a little more slow and romantic, she rested her head on my chest and I held her caressing her back. I planted a couple of casual pecks on her hair. Her palms were on my chest and she planted a couple of kisses on my chest.

We looked at each other and hesitantly, our faces came closer. Our lips brushed and we could feel each other’s breaths. We broke away and now we were breathing heavier and after a pause, we held each other to kiss. We kissed a little and then hugged. I kissed her neck slowly and she had her hands caressing my back.

We were stepping up, kissing more passionately now. As seconds passed by, we were in some sort of trance. In those moments, to me, it was only her lips and tongue that mattered. And they tasted awesome. She was liking my thick lips a lot too and kept nibbling on them.

We consciously stumbled on the twin bed in her room and lay on it. We were laying side by side and looking into each other’s eyes. I placed my palm on her boob very lightly and caressed it. I could tell she liked it from the expression on her face and I could now feel her nipples getting stiffer.

She had her fingers in my hair and pulled a little to her boobs. I unhooked her bra and now I could feel her stiff nipple through the fabric of her kurti. I nudged the nipple with my nose naughtily, looking at her. She let out a light moan. I held it between my lips and pressed it lightly, driving her to raise her kurti.

Her bra came off too as it was unhooked. Now I had those light brown nipples in front of me. I gave each of them a lick while my hands were on her ass cheeks kneading them firmly. A soft moan escaped her mouth as my lips ran on her boobs pleasuring her.

I came up and we were now looking into each other’s eyes and getting a grasp of what we were doing. At that moment, we were in our senses and still nothing else mattered. It was just pleasure. Neither of us wanted to stop. I grazed my lips on hers and felt her arms coming around me to hold me closer.

We were cuddling again and this time, my bare chest was on her boobs. We didn’t know when our clothes came off. My cock was brushing on her soft thighs. She wrapped her legs around me. Our hips were moving. All the caressing already made me hard.

We were kissing as if there was no tomorrow. Her fingers wrapped around my thick cock and she let out a moan as she placed it on her pussy. I could feel her lips vibrate as she moaned, “Mmmmmm mmmmm”.

Then I adjusted myself such that the shaft of my dick was rubbing up and down her pussy rather than going in and out. I gently kept moving up and down, listening to her moans, kissing her neck, and then moving to her jiggling boobs sometimes. A few minutes into this, her moans changed and I could feel my cock get wet with her juices.

I was kissing her neck and went up to her earlobes and nibbled on them. I whispered in her ears, “Can I eat your pussy?”.

As I said that, my fingers were already feeling her pussy lips. She moaned again. I took that as a yes and kissed and licked my way down to her waist. I looked at her pussy and then at her. It was glistening with juices. I rubbed my lips on her inner thighs. They were really soft. I bit her and licked her inner thighs.

I moved up a bit and kissed her pussy while looking into her eyes. Without breaking the eye contact, my tongue slipped out and caressed her clit. Her thighs were resting on my shoulders and my hands were cupping her boobs now. They were playing with them while my tongue flicked up and down.

I got lost in licking her pussy. I felt her hands on my head pulling my head closer to her pussy. Then I held her clit between my lips and suckled on it. She clenched her thighs around my head and let out a long moan. I gave a few more light licks to soothe her. Then I came back up and we cuddled. She started playing with my cock. She went down and started suckling on it. It was awesome.

After a few minutes, I pulled her up and kissed her hard. She again held my dick and placed it on her pussy. I put my hands behind her knees and slowly went deeper with each stroke till my entire dick was in her slippery pussy. The room was filled with our moans, grunts and the thumping sound.

When I was about to cum, I pulled out and squirted the cum all over her boobs and tummy. We then hugged each other and cuddled, kissing and caressing each other.

Later we had a nice steamy shower involving kissing and fondling each other. Soon, it was time for her parents to return. Before they came back, I moved out and traveled back home. We spoke again later that night on Yahoo messenger.

If you liked the narration, do drop me a message [email protected].

I would like to chat and make friends.