My First Anal

This is the story of the first time I was fucked in the ass.

When I was a kid I had a friend named Jason. He was a year older than me and he was my first teacher of sex. We started masturbating together, I don’t remember how it started, around the time I was 11. I’m assuming our method was pretty similar to most boys our age. “I’ll show you mine if you show me yours”

Eventually it lead to us getting completely naked and just rubbing up against each other until we both came all over each other’s stomach. At 13, that was as close to sex as I was going to get and even though it wasn’t actually sex, I still felt like I was getting some.

I’m married with kids. Socially I identify as straight but behind closed doors I am bisexual. Despite getting naked with my best friend and humping each other, I never thought it was gay. Of course I was lying to myself about it and I knew that the first time we did oral sex on each other.

It was just a regular sleepover when we were 14 and I was totally expecting to do our regular routine of making out and rubbing up against each other. Jason surprised the hell out of me when instead of getting on top of me, he got between my legs and started sucking my dick. I was already unbelievably turned on and I came in about 20 seconds. Losing myself in the moment I returned the favor without any hesitation. Jason only lasted about 45 seconds before he came in my mouth. Neither of us were too crazy about the taste of cum at first but the more we did it, the more we liked it. And holy shit did we do it a lot! We started sucking each other off daily, then twice a day! One night we just went back and forth for an hour or more sucking each other off. Neither of us could get enough. The pleasure was awesome and it was equally satisfying to pleasure the other.

This went on for almost two years! Realistically, we probably gave each other between 500-600 blow jobs in 2 years time. We were two horny boys that weren’t drawing any interest from girls so we stayed inside and sucked each other’s dicks.

We’d sleep over at each other’s houses all the time and sleep naked together. We never said it out loud but we were boyfriends. We kissed each other regularly, cuddled in bed together and as I said, constantly sucked each other’s dicks. We always talked about one day having sex but neither of us could tell if the other was joking or serious nor did we have the courage to go through with it. Until we did.

I was 16 and spending the night at Jason’s house. His parents were out on a date night and we had the house to ourselves for a few hours. Somehow we ended up in the shower and we were all over each other. Aggressive making out and rubbing our wet bodies against one another. I went down on Jason first and he came in my mouth very quickly. It was unusual at that point in our relationship for either of us to cum so fast. After I was done, I stood up and he got on his knees and sucked me off. I lasted much longer than him. When I finally did cum, Jason swallowed it and stood up. We started kissing and groping each other some more.

Jason and I never really set any kind of labels on who we were or what we were doing. We just set out to sexually please each other in any way we could think of. One part of this worth mentioning is that I’m a bigger guy. I weigh about 300 pounds. A lot of it is muscle but a lot of it is just fat as well, and with that, as shameful as it is to admit sometimes, I have man boobs. Jason loved sucking them and I did enjoy when he did it. As I said we never put any labels on our relationship but most times I was the bottom or the woman or whatever you want to call it. I just called it two people having a good time.

Back to the shower….

We spent a few minutes kissing and groping each other. Jason fondled my tits and sucked on them for a bit. My hand wrapped firmly around his 7” cock and he was hard as a rock again. I gave him a look like I was going to go back down and suck his cock again but to my surprise Jason took the initiative and became the dominant one in the relationship at that moment.

Jason turned me around and pressed himself against my back. I could feel his rock hard cock sliding between my wet ass cheeks. My heart raced as I began wondering what was he going to do but my mind was racing as well hoping that this was the moment.

I wanted him to fuck me so bad for so long but I was terrified it would hurt or I wouldn’t like it and he’d be disappointed with me. Jason didn’t talk about it as much at this point and I worried we’d never try it. I had been reading everything I could about anal sex and how to make it comfortable and enjoyable and I was as ready as I could be.

At first Jason just slid his dick up and down between my wet cheeks. The more he did it, the more eager I became! When I couldn’t take it anymore and I had lost patience, I reached back, grabbed his cock and pressed the tip against my asshole.

“I want you to fuck me! I’m so ready for you!” I moaned out

Before Jason could respond I started pushing his cock into my hole. As I pushed my ass against him, I felt his head slide into my ass. I moaned out very loud. It hurt like hell but at the same time was the most beautiful feeling I had ever felt. Jason slowly slid himself inside on me. Each time going a bit deeper until I felt his balls slap against me.

Jason lifted my leg and put my foot on the edge of the bathtub and with it was able to go a bit deeper inside me. I was on cloud nine at this point. Jason had on hand grabbing my hip holding me in place and the other reaching around playing with my nipple. My face was pressed against the shower wall and I screamed out in blissful anticipation as awaited the moment he came inside me.

I couldn’t believe how hard and fast Jason was fucking me and how much I was loving it! Sucking him off a few minutes before really helped him last a good long while.

Then I heard the words I had been eagerly awaiting to hear!

“I’m going to cum!” Jason grunted

“Cum inside me!” I cried out

Jason increased his thrusts for a few seconds and then shoved his cock as deep inside me as he could. Both his hands now gripped firmly on my hips pulling my ass as close to him as he could. I could feel his cock pulsing inside me and I could faintly feel his cum squirting against my inner ass. Jason continued to hold me in place as spurt after spurt went into my ass.

When he finally finished, Jason slid his cock out of my ass. That in and of itself was an amazing feeling. I could feel his cum draining out of my hole and trickling down my leg. Jason spun me back around and kissed me with his tongue for a very long time.

“I can’t believe you let me do that!” He said trying to catch his breath. “I was just going to rub it against your ass cheeks.”

“I’ve wanted you to fuck me for a long time now.” I said equally out of breath

“Was it good?” He asked

“I fucking loved it! I want more! Maybe tonight in bed we can go for round two?” I asked

“Absolutely!” He responded, then proceeded to put his tongue back in my mouth.

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