Hello, dear readers! This is going to be a long but fun story, so I request your patience. All the names have been changed for privacy purposes.
My name is Raj, and this is my 2nd story on ISS. This is a real encounter that happened 2 years ago. But it still excites me when I think about it. I hope you all will enjoy reading this piece.
To aid your imagination, here is a brief self-description. I am a 27-year-old fair-complexioned man standing 5’11, have an athletic build and wear specs. I am shy to approach new people, but once I do, I usually end up making friends.
Back in 2023, I went through a terrible breakup.
So, I went on a solo trek to the famous Kareri Lake in Himachal Pradesh, hoping that it would help my mental health. Little did I know then that this would turn out to be one of the most memorable trips of my life. I was a part of a trekking expedition led by a seasoned guide.
Most of my group mates had come with their special someone. It made me feel lonely until my eyes fell upon a mesmerising beauty standing alone at some distance. She was 5’6, had a dusky complexion and short hair that touched her shoulders.
She was wearing a down jacket and flaunted an unmissable bulging ass in her body fit pants. I instantly knew who she was. Overcoming my hesitation, I approached her.
Me- Hi, my name is Raj. I don’t usually do this, but I think I’ve seen you somewhere. Did you go to St. Mary’s school in Delhi, by any chance?
She- Oh, hi! Yeah, I did. How do you know?
Me- Ayesha Khanna, batch of 2016?
She- Hey, yes. Were we in school together?
I extended my hand and she shook it gently. “Yes, we were. You were one of the popular kids so that you wouldn’t remember me. But we were in the same class. Small world!” I said.
Ayesha seemed a little confused. After a few seconds of contemplation, she finally realised who I was.
She- Oh yes, you’re Raj Patel! How could I have forgotten that we even acted in the school production of Romeo and Juliet together!
Me- Well, yes. Now you’ve been able to connect the dots.
She- I blame you! You’ve changed so much since school. Looks like you’ve started hitting the gym, and that beard really suits you.
Her compliments made me blush, but she was right. I was a chubby bookworm back in those days.
Me – Haha. Yes indeed, time changes us all. So, are you alone here for the trek?
At this point, our conversation was disturbed by the instructions of the guide. He asked us to look out for each other, stay in small groups and keep close. And thus, the trek began.
Ayesha and I were walking together. She picked up the conversation from where we had left it. But there was a certain gloom in her eyes now.
She- By the way, yes, I have come alone. My boyfriend was supposed to accompany me, but we fought. I came nonetheless because I needed a change of scenery. What’s your story?
Me- Oh well, similar story, except my girlfriend broke up with me recently.
She- Oh, I am so sorry to know that. I am glad we have each other to keep company here.
We trekked through the beautiful scenery of the Himalayas. We got so deeply engaged in our conversation that the rest of the group had moved significantly ahead. That didn’t bother me as I was thoroughly enjoying Ayesha’s company.
Me- So what’s up with your boyfriend? Why the fight?
Ayesha seemed a little sad at that question. But since it was a long route, she was probably comfortable in my company.
She confided in me. “Well, just the regular issues. He’s always busy with work and doesn’t pay enough attention to me. I feel a certain emotional distance. It’s just not working out, I guess. I wish to feel more wanted, you know?”
I knew what she was talking about. What an idiot her boyfriend must be not to worship this gorgeous beauty every night.
Me- yeah. I get you. You certainly deserve better. And if it makes you feel any better, I did have a serious crush on you back in school.
I scratched the back of my head like a silly boy as I said that. Ayesha seemed a little taken aback.
She- are you serious? Why didn’t you ever tell me?
Me- never thought I had a shot, simple as that!
At this point, we had to climb a steep slope. I did it with some effort (thanks to strength training in the gym). Ayesha needed a helping hand, which I gladly extended. As I pulled her up, my hand accidentally brushed against her side boob. The feeling was so good, it made me semi-hard.
Ayesha noticed what had just happened, but she didn’t seem to mind. She thanked me for my help, and we moved on. That moment made our conversation awkward. I realised that all those feelings for her I thought I had buried long ago were becoming alive again.
The path was tough, but now, our regular touches and brushes against each other’s bodies (some intentional and others not) made the journey fun. Once, Ayesha brushed her hand against my crotch as I was helping her cross a brook.
I was already becoming hard from all this sexual tension that was building between us. The climax of our upward journey came just before we reached the mountain top. I was waiting for Ayesha to cross a tricky hike. Standing on the other end, she tripped and fell right into my arms.
I will never forget the excitement of that moment. Her boobs were firmly crushing against my chest. My hand accidentally rested on her ass as I tried to support her. Our faces were so close I could feel her breath. In that moment, Ayesha shocked me by placing a light kiss on my lips.
I had been aroused all along, but wasn’t expecting this, as she was already committed. We both decided not to talk about what happened. We reached the top sometime after the rest of the group. As it was cold as fuck, the group lit a bonfire and we started drinking, singing and dancing, having a merry time.
Finally, Ayesha spoke to me again- “I am sorry about what happened earlier. I don’t know what I was thinking.”
Me- “It’s okay. For what it’s worth, I enjoyed it,” I said, only half-jokingly.
Finally, it was time to go to sleep. Ayesha’s tent wasn’t very far from mine. As I was preparing my bed, I heard her call me out.
She- “Hey, Raj, come out for a minute.”
I did.
Me- “What’s up? You’re not sleepy?”
She- Not at all! Who wants to sleep when we are beneath such a beautiful sky! Wanna go for a walk with me?
The sky indeed looked heavenly. I instantly agreed, and we started walking slowly away from the tents, towards a gentle cliff, hand-in-hand.
She- “It’s so cold, can I please hug you?”
I was a little hesitant knowing what could happen, but I couldn’t leave her freezing.
Me- Sure, come here.
Her touch sent shivers down my body. We were close enough for me to smell the alcohol in her breath. Yet, I tried to maintain my control and looked away while talking to her about random things.
Me- I am so glad we are here on such a beautiful day.
To my utter surprise, Ayesha pulled my face close to hers, looked into my eyes for a fraction of a second and began kissing me again. She didn’t let me finish.
I didn’t know what to do. I pushed her away.
Me- “Listen, Ayesha, you have a boyfriend! This is just the alcohol talking; you’ll regret this tomorrow morning.”
She would have none of it. “I don’t care about tomorrow morning, I want to live in this moment,” she said and again locked her lips with mine. Just when I was about to protest again, she took my hands and placed them on her ass. My last defence was now broken, and I couldn’t hold back anymore.
I started squeezing her ass hard and opened my mouth to invite her tongue in. What a heavenly feeling it was! After smooching passionately for about 5 minutes, I pulled her hair back. She struggled to look me in the eyes even as I unzipped her jacket.
There was a loose white top underneath. I pulled it down, and out popped her right boob. I started pressing hard as she moved her hand on my cock over my thick pants.
“Please, Raj, I want you so bad. Please don’t make me wait,” she implored weakly. I was sniffing her slender neck, gently at first and then started biting it.
“Babe, you’ve messed with the wrong guy; now pay for it,” I whispered in her ear.
I ran my tongue down her neck to her right nipple, nibbling at it gently.
Under that starry night, on a cold mountain top, I was sucking this hot chick’s boobs as she was pressing my rock-hard dick! This was truly life at its best.
“Come inside with me,” I ordered and lifted Ayesha in my lap, all while smooching her. We entered my tent. I sat down on the tent floor and made Ayesha sit on my lap, her legs around my waist. She placed her hand on the back of my head to press my mouth against hers.
Meanwhile, I hurriedly took off her jacket and pulled up her T-shirt. There she was, topless before me, her boobs inviting me desperately to maul them like a hungry tiger. That’s exactly what I did. I groped both her boobs while kissing her and pulled them together, hard.
Ayesha broke the kiss and whispered in my ear, “Make me your slut tonight! I want you inside me.” Her words drove me crazy with lust, but I wanted to tease her further. I unbuttoned her jeans and put my cold hands inside her pants. She was so warm.
I found my way through her pubes and found her glory hole, inserting 2 fingers at once. Ayesha moaned uncontrollably as I twisted and turned my experienced fingers in her vagina. Her “Ah!Fuck!” and “Oh, this feels so good!” were enough indications that this was a job done right.
I suddenly rose with her in my lap and gently placed her on the tent floor. I stood up, took off my pants and boxers at once and sat across her boobs without putting too much weight on them. She’s a petite girl.
Me- You want my cock, baby?
She- Oh yes, please, I want it so bad.
I didn’t need a second invitation. I moved ahead, asked her to open her mouth and inserted my dick inside her mouth in that very position.
Ayesha was a pro at sucking, as a slut like her should be. She spat on my dick and began working her magic. I enjoyed fucking her mouth for another 10 minutes, thoroughly enjoying the feeling of her soft lips wrapped around my long cock.
She- Fuck me already, you bastard, I want to feel you inside me!
I knew it was time. I took off her pants as she sat up. I took a condom packet out of my wallet, tore it open and handed it to her. She knew exactly what to do. While looking into my eyes, she slowly rolled the condom on my cock.
I asked her to enter the sleeping bag with me, and she followed. I lay with my back on the floor. Ayesha came on top of me, facing me, with her legs spread a little wide apart. As we were kissing sloppily, I positioned my dick at the entrance of her vagina.
Oh! She was so wet and so tight. I started stroking, gently at first but vigorously later. Meanwhile, I groped her boobs, and my fingers kept playing with her erect nipples. I finally came in the condom after fucking in this position for 20 minutes.
Ayesha’s eyes, too, were teeming with satisfaction. In the dead of that cold wintry night, our bodies were covered in sweat and each other’s fluids. I couldn’t have asked for a better trip. We got out of the sleeping bag. Ayesha wanted to cuddle naked, and I was game.
She- Can I tell you something?
Me- Yes, what?
She- I’ve never experienced a beast like you. My boyfriend isn’t half as good.
Me- Don’t worry, baby, you haven’t seen the last of me.
Saying this, I placed my hand on my right boob and started kissing her again, even as she was stroking my semi-hard cock.
Me- Want to do this again?
She- yes, a thousand times yes!
I knew that it was time for round two, but fucking without foreplay is a sin in my eyes. I came on top of Ayesha, gently kissing her forehead, then cheeks, then the tip of her nose. Just before reaching for her beautiful lips, I moved my face slightly and bit her earlobe gently.
This move works like a charm every time! She moaned and scratched my bare back with her nails, spreading apart her legs again. “Open your mouth,” I ordered and dove inside with my tongue.
After kissing her wildly for some time, I started moving down. First was the turn of her slender neck. But her round boobs were too inviting for me to stay there for long.
I moved further down and started sucking her left nipple while pressing the right one as hard as I could. While I left love bites all over her left boob, my hands were already imprinted on the right one.
After giving similar treatment to her delicious melons, I finally inserted my mouth into her wet pussy. The smell and taste of her fluids was working magic on me. As I ate her clit like a hungry dog, Ayesha moaned loudly, and I had to cover her mouth with my hand.
She- I’m loving this, Raj, but I beg to God, please fuck me again!
Me- Come on your fours baby, let me make you my bitch tonight.
It was time for my favourite position- doggy style. Before entering her, I rubbed my dick on my vagina to excite her further.
She- Enough, enter me already!
As I was about to wear a condom again, she said- No need. I’ll be on my period tomorrow. I want you to come inside me.
Nothing can make a man happier. I gently entered her pussy. The strokes were slow and romantic at first, prompting Ayesha to say- “Oh Raj, I love you so much!”
“Not so soon, bitch!” was my response. I started fucking her roughly at this point and pulled back her hair. As her moans threatened to expose us, I bent forward, kept my right hand across her boobs and asked her to look back.
We smooched as we fucked in doggy- pure porn stuff that was happening to me in real life! After fucking in this position for another 30 minutes, I finished inside Ayesha. She was yet to come.
I turned her around and started fingering her. Finally, Ayesha came too, the third time in one night! As we lay peacefully in each other’s arms, I realised that it was already 4.30 am. The dawn was arriving on us, and people would start to wake up soon.
Ayesha quickly put on her clothes and, before sneaking back into her tent, planted a light kiss on my lips. “Thanks for the best night ever. This isn’t over yet!” was all she said.
Indeed, it wasn’t. While trekking down the next day, Ayesha told me about her fantasy to fuck in the woods. I, being a good friend, helped her live that fantasy to the extent that it got forever etched in her memory. But that’s a story for another day!
Thanks for reading the story. I hope you enjoyed reading it as much as I enjoyed putting it into words. Any feedback is welcome on Google chats at [email protected].