Best friends can fuck too

Like most people, years ago I was still trying to figure out who I am. I was taught that I'm a boy so I have to like girls and I do. But I also find girls almost not human. I mean I get tongue-tied and nervous around them. That makes them foreign to me.

My best friend Jim and I have always been close. He's taller, stronger and better looking than me in my opinion. He's 20 years old, 6 foot 180 pounds with blue eyes and more on the muscular side.

I on the other hand am average at best. I'm 19, 5"5, 180 pounds (chubby) with blue eyes and slightly longer brown hair. I've dabbled in cross-dressing for some time now. Not many know I like to dress up, just a few random hookups when I was younger.

Jim was moving off the farm to a small town nearby. Of course, I helped him move. It was dark by the time we got unloaded and both of us were tired. We had ordered Chinese food, ate and then sat around letting the food settle.

The plan was, I was gonna head home after we were done but I felt tired so Jim insisted I stay the night. He was the one with the vehicle so I didn't have much choice.

All he had was a single mattress so we agreed to share it.

It was hot that night so we stripped down to our underwear. Jim wore tighty whities. I always wore silk underwear. I've liked the feel of silk since I discovered my mom's panties years ago.

Jim of course made fun of them so I joked with him I could sleep naked if that made him feel better.

He didn't say no right away as I expected him to so I paused and looked at him.

You know what, those panties are just gonna give me a hard-on so yeah, strip them off. He said.

They're not panties bro, their men's silk underwear I said.

I looked at his package and realized he was getting aroused.

Someone in my head said, oh wow. He likes me and the next thing I know I'm kicking my underwear to the corner with my other clothes.

He did the same for some reason.

We lay beside each other on the small mattress on the floor but it simply was too small. I looked over and saw his cock rise off his belly. My curiosity got the better of me as I watched it grow. He was much bigger than me, that's for sure, I got aroused at the site all the same.

I tried closing my eyes and ignoring it but that didn't work.

It was very quiet for a while. Then Jim asked if I wanted to lick it.

I thought about it for a bit then said yeah, I do.

I got up and positioned myself between his legs. His cock was very hard and precum was leaking from the tip. I looked him in the eyes as I licked from the base to the tip. His excitement grew and so did his cock.

I know you wanted my dick for a long time now, why didn't you make a move he asked.

I stopped long enough to say I was scared you'd kick my ass if I tried something gay with you. Then I took the head of his impressive cock in my mouth.

I got into a rhythm of sliding my mouth up and down, each time I went down I'd go further and further until my nose touched his pubes. I realized his cock was in my throat and choked on it right away. I came up for air and stroked him hard a few times then slid it back to the hilt. I sucked him for all I was worth for maybe fifteen minutes.

Then he grabbed my head and exploded into my belly. I gagged and choked but he held me tight until he was done.

I came off his cock fast as I gasped for air. At first, I was a bit mad because he was choking me but then I realized he had given me the first load of cum I'd ever swallowed. Cum and saliva were all over my face and chest.

I had been with other guys before but I never let them fill my mouth or ass because of STDs.

Jim was different, he was my best friend. I knew him very well.

My little dick was hard as steel. I knew it wouldn't take much to get it to explode but I wanted to wait and see if he was gonna blow me.

I lay beside him and waited. We both took some time to catch our breath. I glanced over at him. His cock was getting hard again. This just excited me more but I wasn't sure he wanted me to suck him again. We were both quiet for a while again. My hard-on went away for the most part so I turned on my side facing away from him. This forced him over a bit so he turned towards me and spooned me nice and tight. He said good night little buddy so I thought that was it.

I drifted off to sleep a little while later.

I woke up first the next morning. I could feel his soft cock resting at the entrance to my ass. His arm rested over me.

I moved my ass up and down on his cock to let him know I wanted him. I reached around behind me and stroked him for a while. Slowly he got hard. I took a gob of my spit and applied it to my ass then another gob slicked up his now hard cock. I took hold of him and put it to my ass and slid back and forth. Slowly it slid in slightly.

It felt really good to me. I didn't move for a bit, then he pushed in a few inches.

I tensed up as the pain hit me. I squeezed my ass right on the invading cock stopping his advancement. He held still as the pain slowly subsided. His hand slid down to my hip, then he slid in all the way slowly.

Once there he held still again.

Are you ready little buddy, he asked.

Yeah, go ahead. I told him

He withdrew most of his length. His cock raked past my prostate causing my precum to flow from my still limp dick.

He slowly fucked me into a frenzy. Never once going too fast but always burying his beautiful cock deep with each thrust.

My dick didn't once get hard, it stayed limp but juices flowed steadily from it. He pulled out leaving me feeling very empty and moved me toward the middle of the bed. I lay flat on my stomach as he filled the emptiness again.

His rock-hard cock pinning me to the mattress. Neither of us spoke words but our bodies spoke volumes. I could feel a big wet spot forming on the blanket that covered his mattress but I didn't care.

With long deep strokes, Jim pounded my chubby ass into the mattress. I could feel sweat hitting my upper back and shoulders as he fucked me.

Then I was empty again. I got up and he lay in the middle of the mattress right in my wet spot.

I got on top and lowered my gaping hole down, once again filling the void.

Riding a cock felt different. It felt like I was getting more cock deeper than before. My hands rested on his stomach as I slid up and down at my own pace.

We stayed in that position for a long time. Not that I was complaining or anything but I wondered how much longer he could go before I got filled.

Then he told me to get off for a second.

I really didn't want to but I did as he asked. He laid me on my back and put a rolled-up blanket under my lower back that raised my ass up high. This way he could stand over me and hold my legs over my head. He slid in easily all the way down. Precum flung from my still limp dick and covered my face as he pounded my ass hard. I actually loved this, to be honest.

We fucked all day that day in every imaginable position. He filled my ass twice and covered my face once too.

Later as the cum crusted on my face and body he asked if I liked what we did.

It kinda felt like he felt guilty but I definitely didn't. I told him I loved it so much, I probably wouldn't want to be with a woman.

That's how he found out I was still a virgin. Well with women that is.

I ended up moving in with him. We lived with each other for three and a half years. I started to transition but I don't think Jim liked that for some reason.

He ended up getting a girlfriend and moved in with her but from time to time he'd pay me a visit.

Names have been changed as this is a true story.