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Thanks to my friend Jeremy

1640 words | 1 |4.67

How I became addicted to pleasuring gay older men.

This is a real story.
A bit of backstory about how I lived my life before my first gay experience. It started in grade 5, I was 10 years old and hadn’t had many friends.

I was bullied a lot so I became what you would call the quiet kid. I had 1 friend that I had grown up with all my life, he was my neighbour. He was the same age and looked almost identical as me growing up so we were mistaken as brothers by many.

We lived on a small street that was right across from a small playground. The playground had swings, a slide, and a baseball diamond that was surrounded by trees. Within the bushes there were as few places that we’re cleared enough to play around without getting smacked or stabbed by tree branches, and large, flat rocks to stand on. There was this one particular rock that was huge, it could fit 7-8 adults so as kids it was pretty big.

Anyways, that rock was called the “love” rock because everyone on the street said that’s where they caught 2 people having sex.

Growing up, I had very strict parents. Although my mom was native, she grew up in a christian home like my dad. I had no freedom and would be punished for small mistakes.

Anyways back to the story. Me and my friend were both 10 years old and were super close, we’d often visit each other’s houses when hanging out or play at the park.

One day we decided to go build a stick fort in the bush. After a few hours of collecting branches off the ground, we took a break.

Right beside where we were making our little fort, was the love rock. It was perfect for a clean place to sit and relax. He started to get undressed to his underwear and lied down on his back and I did the same.

Eventually he started playing with something in his underwear and popped out his dick through one of the sides of his boxers and played with it

I was super curious and asked him what he was doing. He replied that playing with it up and down felt good and told me to try it out I said his looked different than mine, so he looked over and told me to pull the skin down like he did. I was scared so I didn’t.

The next day we went back to continue with our fort when he suggested we took a break at tge same place. After we both undressed, he asked me to try touching his dick, so i said sure. I slowly pulled it down and up in my hand as he instructed me and i gradually started to move faster.

He than asked me to suck on it since that make it feel better. I was hesitant but did so. I sucked his cock until he came without warning into my mouth. I ended up swallowing his cum. We continued that for a few months until we just stopped.

I didn’t know what I did until I was much older. Nothing else happened until the first year of high school. We went to the same high school together and made a few new friends where he came out as Bi.

I became attached to one of our friends and me and her got close. We started hanging out together at her place where we would play videogames or study for classes we had together.

We were a good match as I don’t talk much, which makes me a good listener, and her who loves to rant about everything. One day she decided that she wanted to do my make-up and dress me up, while I don’t look very feminine at all, I had long hair and was closer to my feminine side of a personality. That became a weekly thing then daily.

Whenever I was over, we’d continue to do the normal things together while I was dressed up, and while it was pretty uncomfortable most of the time, through having my rock pressed tightly to whatever I was wearing, or hanging out from a skirt or something similar, she never cared.

Eventually we grew apart and stoped hanging out together and she ended up moving away. Well while we never done anything together sexually, I became addicted to wearing girls cloths around in private away from my family and friends.

Since no one else knew about it, I started stealing my younger sisters clothes and wore them to bed, or around my room, or her underwear under my clothes outside.

About a year after the pandemic hit and everyone started going back to school, I started to get brave enough to dress completely after school and wander around the bushes at our house. Since I had a face mask on, I believed that no one would recognize me since my face is what mainly yells out that I’m a dude. It worked and I would end up walking past people and people I knew never recognize me at all.

Of course I was exited and wanted to do more and that’s when I remembered about me and my friend Jeremy and what we did when we were younger. Well he strongly believed I was straight and he’s not very good at keeping secrets so i decided not to tell him.

Instead I started looking around for ways to show people me without them knowing It was me, that’s when i came across Grindr. I made an account and loved how easy it was. Quickly I was getting messages from guys and was exited to chat. Well a few guys wanted me to keep sending pics of me posing in the mirror all dressed up and showing everything off, when a few asked to meet up. I didn’t know what to do but agreed to meet up with one guy that wanted me to please him and a friend of his.

So i planned my way to leave the house close to dark and when night came, I slipped out all dressed up and started walking towards his place. I was about a 15 minute walk from my place so it was close.

When I got there, I knocked on the door and one of the guys let me in. There was a few guys there watching some movie which I was too nervous to pay attention to, when the guy I messaged started introducing himself and his friends. There were 4 including himself, all around the age of 30-40. I ended up sitting there in silence for what felt like an hour when one guy asked how many guys I’ve been with before, which I replied that this was my first time.

The next question he asked was If i was ok getting fucked, which i replied yea. He got up and slipped down his pants and asked me to suck on his dick first. So I got up off the end of the couch and sat on the ground in between him and grabbed his dick suck and started sucking.

He rested one hand one my head, not pushing down or anything while the other guys started slowly touching my arms and legs when the guy beside the person i was sucking off asked me to suck him off next when the fist guy pulled my head off, got up amd asked me to bend over on the couch.

I got up and pulled my panties down and got on the couch, bent over amd started sucking the second guy, the first guy stared spiting on his finger and slowly started fingering my ass, which felt pretty good.

I started sucking faster when the third guy had his phone pointing at me and asked if he could record, which I replied sure.

While he started recording the first guy was slowly poking my ass hole with the tip of his dick, when the second guy told me me to make sure to show the camera before I swallow, i was caught off guard, then he suddenly came in my mouth.

He pulled out of my mouth and pulled my chin up to show the phone screen where i opened my mouth and stuck my tongue out.

A few seconds after swallowing, the fourth guy got up off his seat and sat down in front of me, already naked and told me to suck him good.

He pulled out his phone as I started sucking him when the first guy started pushing a little bit faster and came inside me, then just leaned over me for a little bit. I felt really warm and my dick was super hard.

I got back into the pace of sucking the fourth guy off when the third guy passed his phone to the first guy and got behind me and just slipped it in and began pushing slowly, and holy fuck did it hurt, he wasn’t very long but he was thick. It really hurt, so much that I was off rhythm and couldn’t suck the fourth guy off properly. Because of thay, he started pushing my head down rapidly where he then pulled out and came in my face and hair.

Close to the same time the third guy pushed his last push and came inside of me as well. After a few minute to get cleaned up, I pulled my skirt down to its correct spot and adjusted the bra straps and put the panties back on and made my way out. I snuck back home and went to the bathroom and came the biggest load I’ve ever had.

Still to this day. Now when i have time, I go looking for someone to pleasure. And still my biggest secret.

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1 Comment

  • Reply Sammy ID:vuf1myhm

    Sometimes you never know what feels good my neighbor was an older guy and sometimes when I would go over and hang out with him he asked me if I wanted to let him see me naked I told him I was not ok with that the next week when I went over to see how he was doing he asked me if I wanted to come in and have a drink we had a couple and when he asked me if I wanted to let him see me naked I was ok with it when I took my underwear off and was standing in the living room he told me to walk around so he could see me better and he took off his underwear and started rubbing his cock against my ass a little but when He asked me to spread my legs open so he could see my ass I just wanted him to lick it he licked my ass for a while and then he asked me if I wanted him to put it in my ass he handed me some lotion and I started to put it on my ass and he sat down on the couch and told me to sit on his cock I started to move up and down on his cock and he told me to suck his cock and open my mouth