Hello everyone, this is my first story on ISS. I’ve been reading stories here for almost 6 years now. Had a few encounters myself, but never really felt like posting anything. Maybe hesitation or just laziness.
Anyway, I finally decided to share this one experience. If people like it, I might post more later.
Names are changed, obviously.
So, I’m Sam, 26. I’m about 5’11. Athletic build, but yeah, I’ve put on a little belly over time, which I’m trying to get rid of now by working out again. Not gonna lie, I’m decently gifted too, around 7 inches.
The girl in this story is Shweta (name changed). She was 30 at the time. Very slim, hot in a subtle way, someone who doesn’t get too noticed, a shy personality, one can say. Her stats were 32-25-34.
I used to work as a customer care representative a few years back. That’s where I met Shweta. We weren’t close friends, but we spoke often at work. I always felt she was interested in me, like small hints here and there. But I never made a move because I was already dating someone seriously at that time.
Eventually, I left that company and slowly lost contact with almost everyone from there, including her. About one and a half years later, I had just gone through a breakup. One of those messy ones. Anyway, one night I was scrolling through Snapchat randomly.
I saw Shweta’s story. First snap said “Back on Snap,” and the next one said “Deleting again.” I laughed and thought, what’s wrong with her. Without thinking much, I replied:
Me: Have you lost your mind?
She replied almost instantly.
Her: Hey! I actually wanted to ask you something.
Me: Yeah? What is it?
Her: Are you single?
Me: Yeah. Just broke up recently. Why?
Her: I liked you since we worked together. I tried giving hints, but you never noticed.
Me: I noticed. I was just in a relationship back then.
Her: So, what now?
Me: Are you sure you like me? I roast you all the time, and I’m not exactly some handsome guy.
Her: Do you want to date or not?
I was like, whoa, someone’s on defence today.
I called her. We spoke for a bit, and there was no awkwardness at all. I was with my friends at that moment, but my mind was already somewhere else.
I thought for a while and told her, “I’ll come over. Let’s talk properly.”
She agreed. So, I left my friends and headed to her place. So I headed over to her place, honestly, to do an intent check to see if she was serious or just bluffing. I booked a cab and reached her place around 2 at night.
She opened the door, and I won’t lie, she looked really cute in a purple shirt. It was a small 1BHK apartment. We went inside, and I sat on her bed. For a while, we just talked casually. I asked her what was going on and why she suddenly brought up dating.
She opened up and told me she had recently gone through a breakup and was trying to move on from it. I was honest with her. I told her I wasn’t in a place where I could be serious and that if anything were to happen, it would have to be casual.
I also said that it seemed like she wasn’t looking for anything serious, either. She just wanted to get over her ex. She went quiet for a bit, thought about it, and then said yeah that is true.
While we were talking, I held her hand. At one point, I pulled her in for a kiss, but she got startled and pulled away. I immediately apologised and asked if she was okay. She said yes, but that she just needed a little more time to feel comfortable. I respected that.
She suggested we lie down instead. We lay down next to each other, talking softly. I could tell she was still a little tense, so I just held her, rubbed her back, and tried to calm her down. I stayed close, reassuring her, letting her feel safe.
Slowly, she relaxed. At one point, she leaned in and kissed me this time, completely on her own terms. The kiss was intense and full of pent-up emotion, which felt natural and mutual.
So, I moved my left hand behind her ear and started rubbing there (trust me, it makes them go crazy), right hand in her hair and massaging the scalp slowly but hard, like taking control of her. Oh my god, she lost control. She climbed on top of me, kissing me. I could see something open up in her.
I held her by her throat and said that’s more like it. I kissed her really hard, biting her lips, exchanging saliva, and fighting with our tongues. All the while kissing like there was no tomorrow. Then we took a second to catch our breath. I got down from the bed, grabbed her hand, pulled her close and lifted her chin.
I looked right into her eyes and said you want this princess, she bit her lip and said, after letting out a slight moan, “Yes, Daddy. You want me to do whatever I want, however I want. Should I make you my slut for the day?” Surprisingly, she replied, “Yes, Sir, please use me as you want.”
I pulled her close and kissed her again and whispered now that’s a good girl. I held her shirt and ripped it open; she gasped for some air. I didn’t wait for another second and grabbed her hair, and started going wild on her neck, leaving a trail of marks over her shoulders.
She begged me to continue more. She said, “Yes, make me your slut, mark me all over, make an example out of me. Show my ex what he lost.” I kept on going wild and started mauling her tits and started sucking on these nipples one by one.
Then I stopped and asked her to bring in two rubber bands. She was so confused, I said, ” Trust me.” She has long hair (you will know later). She brought that, and I kept it in my pocket. She removed my t-shirt and started kissing my face all over.
She started to go down, kissing my chest, sucking my nipples. She knew exactly what she wanted. I calmly watched her movements. While sucking, she started unbuckling my belt. I helped her out a bit, and she got down on her knees.
Sliding my pants down, my dick popped up in her face. She was awestruck after seeing my size. I had a grin on my face. She said, “I have never seen a cock this big. My ex was just 5 inches.” I replied, “Don’t worry, baby, I’m going to reshape that mouth and pussy of yours to my size.”
I grabbed her hair again and asked her to pull out her tongue. I slapped my cock on her tongue a few times, then on her face. She was smiling through it. I let her hair go and asked her to start sucking it. She started slow by licking it all over, moving down to my balls and sucking them, making them wet.
I was moaning literally, eventually she moved up and started suck of the tip. Slowly going deep, taking up the pace. I was literally in heaven. I remembered the rubber bands I asked for, I divided her hair into two parts and made pigtails out of them.
I held her head and started deep throating her, taking back the control. She was choking on my cock, drooling all over it. I love a sloppy blowjob. Then I held those pigtails and started fucking her mouth. I continued fucking her mouth for 5 more minutes, deep throating her in between.
The room was filled with those ‘pach pach’ sounds of her mouth. My moaning and occasional gasping for breath. Then I pulled her, kissed her again, and patted her head, saying, “Good girl. Now let me give you your treat, kitten. Get on the bed and take off those pants.”
She did the same and followed my orders like a good slut, and then she spread her legs on her own. I said, “I like it when my princess does these things without being told.” She was so horny at that time, I didn’t waste much time. I got on my knees to return the favour.
I started with kissing her thighs, both sides, biting a little bit, not too much. Slowly moving towards our pussy, I blew some air around it. Hovered my tongue just close enough that she feels it around. She started begging me, “Please, Daddy, I can’t take it anymore.”
I didn’t say anything at first, but then I slapped her pussy lightly and rubbed a little. She started to shiver, saying, ” Oh God, this is too much.” I did it 3 more times, she went crazy begging me, “Please eat my pussy, this is too much, I can’t take it anymore.”
She literally grabbed her head and shoved it between her thighs. I gave her what she needed. I started licking her whole pussy, which was dripping wet by now. Slowly, I shifted to licking and sucking her clit. After 5 minutes of licking, I added it to my fingers.
I directly inserted two fingers inside her, which slid in easily. I licked and finger fucked her for 10 more minutes, and she reached her first orgasm. She cum all over my face. She was gasping for air and trembling after this, so I kissed her forehead to calm her down and hugged her.
Yes, folks, Daddy knows how to give after care. Once she calmed down. I took out the condom I carry in my pocket. I placed it on my dick, and then I picked her up and bent her over and entered her slowly. She was in pain because it was her first time taking a 7-inch cock.
But it went in smoothly because she was still damn wet. I started off going slowly. I pulled my dick out and started rubbing it on her pussy, teasing her after giving her the taste of it. She tried to adjust her pussy so that it could slide in. I suddenly rammed into her completely without any warning.
She screamed, and I didn’t show any mercy and continued to fuck her like there’s no tomorrow right then and there. I fucked her for approximately 8-10 mins, and she was screaming at the top of her lungs. I turned her around, lifted her in my arms and fucked her in the air.
I moved to her kitchen and placed her on the kitchen slab. I placed her legs on my shoulders and continued fucking her in that position. She felt a huge wave coming. She told me she was close, she was going to cum. “Please don’t stop, yes, right there. Oh god fuck!”
She had another orgasm, and she was exhausted by now. I carried her to the bed in my arms, caressed and cuddled her till she calmed down. Once she was normal, she got on top of me, saying now I will do it this time. She started riding me and grinding her ass in between, and damn, she was so good.
She later told me her boyfriend could never last this long (let alone make her orgasm twice). She rode me for a good 5-7 minutes. Then I pulled her down. I took her in front of her dressing mirror and shoved my cock from behind again. I grabbed her by the neck with one hand.
The other hand was on her tits and started to ram her really hard. I fucked her like that for 5-6 more minutes. We both were so close to cumming. I increased my pace and started to ram her at full speed. And she cum again. I slowed down and asked her where she wanted it.
She said, “I want to swallow it, Daddy.” I took out my cock, removed the condom, and started fucking her for a minute or two raw. Then I pulled out, and she got on her knees. She started to deep throat me while playing with my balls. I couldn’t hold any longer.
I held her face right there deep on dick and came all inside her mouth. She swallowed it like a good slut. Then we moved back to the bed where she rested her head on my chest, tracing slow patterns with her fingers. We drifted off to sleep.
I knew this wasn’t going to be a one-time thing. The look in her eyes wasn’t about release anymore; it was curiosity. Hunger.
This was just the beginning.
If you liked this story, let me know. There’s definitely more to come. And if any women or milfs resonate with this dynamic and want to connect, feel free to reach out: [email protected].
What did you think of this story??
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