My first anal [MM]

I never thought of myself as gay, even now after having sex with a man, I still don’t check out other men on the street, BUT, in the last couple of years I’ve become obsessed with trying gay sex. I wanted to be fucked. I wanted to give blowjob. All of it. It’s come to a point when I don’t even masturbate without a toy in my ass while imagining a dick in my mouth. So I guess I’m bi, since I still love boobs and pussy.
But I live in a small town, trying it was impossible. So when I was told I’ll go on a three day business trip in my country’s capital, I knew I can’t pass that opportunity, I immediately started browsing the classifieds.

First day there, after work in my hotel room, I chose an add, a student, just the body shot, normal, average looking guy, called him and we set up a meeting for tomorrow evening. I was super nervous the whole day! Almost called it off, but then I remembered how long I’m fantasizing about it and said, fuck it, I’m going through with it. What happens, happens!

He came, was just like on the photo, average guy, even little shorter than me. We first got business out of the way. He was not cheap! But well worth it, as it turns out. I told him I was never with a man, this was my first time. He said it’s OK, we’ll do what I want and how I want it, I’m in charge. Him being so OK about it made me a lot more comfortable.

He then went into the bathroom, and came out with nothing on him but boxers! I don’t know why this surprised me :D He asked what I want to do, I said I’d like to start with him giving me a blowjob. I actually said that just because I wanted to establish some dominance, I was still nervous as hell about being fucked.
He told me to sit down, pulled down my pants and started to give me the most awesome blowjob. It didn’t last long, I was hard in seconds but I stopped him, I didn’t want to cum like that.
He stood up in front of me, I pulled down his boxers, and there it was, my first dick right there in front of me!
All naked and nice, everything completely shaven. I’m usually a smart guy, but at that moment smarts went out the window. I got down in front of him, he was completely flaccid, so I took him, pulled over his foreskin, and I put it in my mouth!
I couldn’t fucking believe it, it’s like I wasn’t me! There I am, sucking dick! And it was great! Playing with him in my mouth, sucking it, caressing with my tongue. He put his hand on my head like he was encouraging me. So I licked his balls! Feeling that texture on my tongue was absolutely fantastic! Turns out I could lick balls all day long :D Then I sucked him again, and he started to get hard. Having a dick grow in your mouth sure is something else! You did that! Your mouth made him hard!
Once he was hard I started to give a proper blowjob, it was probably a shitty blowjob but I didn’t care :D I was fascinated by the dick. At the same time hard and so soft and gentle. That head gliding over my tongue, locking my lips around it, sucking it in as much as I could, licking him from the balls all the way to the tip, kissing that cute little hole. I actually wanted him to cum in my mouth. But I was beyond horny at that point, I wanted him in me even more. So I stopped, took the rest of my clothes off and lay on the bed, we were now both completely naked. I’m guessing by my look and smile he knew exactly what I want, because he took his little purse and took out a condom and a bottle of lube.
He sat down next to me and rolled me over on my stomach. I instinctively spread my legs like it’s something I do every damn day :D He took the lube, poured some on his fingers and some on my ass. And then started to cares my asshole. Such pleasure! Soon after, one finger was in. Wow! Then another. Oh wow! No toy can compare to someone else touching you.
I was still a little nervous about his size, even though he had a normal size dick, it was still larger than my toys, I was afraid how will I take it, but at that point I couldn’t wait any longer! I said those magic words, “fuck me in the ass”. Note that that sounds so much naughtier in my language :D

He put on a condom, and I assumed a position. There I was, down on all fours, my ass sticking up in the air. This is it! He’s behind me! His hand on my back. It’s actually happening!
And then it happened! His dick touched my asshole and started to slowly go in! First the head. Then a little more. Then a little more. Couple of thrusts later and he was all in! No trouble at all!

Let me digress here and say that this is absolutely because I practiced so much with toys. When ever I read someone saying it was their first time and they got fucked and it was great I’m assuming it’s all a lie. You have to learn to control those muscles down there. When something touches you there, the reflex takes over and they contract. You have to learn to control them and keep everything relaxed. It’s nothing special, but still requires some practice. You can even use something really thin line a pen, doesn’t matter, just learn to take control. Back to topic.

He was all in. He took me by my hips and started to actually properly fuck me! Nice moderate pace, dick going all the way in, and out, all the way in, and out. It was amazing, so much better than I ever imagined.
First there’s the physical side of it. Thighs touching, my ass pressing up against his body, my body rocking back and forth as he fucks me, his hands holding my hips. And of course, dick in my ass. It’s like caressing, pleasuring and the best massage in your ass ever, all bundled up in one package of dick happiness. I can’t describe it, you just have to try it to know. No toy can even come close. When someone else controls the pace, and you don’t know every single move in advance. His, as I call them, surprises for my ass drove me crazy. He’d go all in, then when he starts to go out he goes just half way, and then sticks it back in. Fantastic! I caught myself smiling and moaning, which just made me even more horny :D
Then, there’s the physiological aspect of it. It’s happening. I’m actually getting fucked in my ass. I’m actually having another man’s dick inside me! I’m actually loving it! I’m giving my ass to someone, and his taking me from behind. There is something so exciting and liberating about it. Being on the receiving end is completely different! You give yourself and you love it, you love that someone wants to fuck you. I was completely his. I’d do or say what ever he wanted me. Nuclear missile codes? Sure, it’s 0000, just don’t take your dick out of my ass :D

At one point he grabbed my ass and pushed me forward, than pulled me back. I immediately knew what to do! I started rocking back and forth, fucking myself on that wonderful cock of his. I wanted to be a good fuck for him! His hands started to wander over my body. Grabbing my ass, touching me everywhere, caressing my back, shoulders, neck, sides, stomach, giving little slaps on my ass :D So wonderful.
Then he took me around my waist and again started to fuck me. This time just a little faster and harder. Not porn banging, we were never close to something like that, just a little more determined :D

Now, I don’t know what was it, his hands around my waist, or the change of pace, or all of the above, but I started “orgasming”! I put it in quotes because I wasn’t actually cumming, sperm just free flowed out of my dick but everything was still relaxed down there.
The feeling in my ass as this started to happen was like nothing I ever felt. I won’t even try to describe it. Pure pleasure! My feet got really cold for some reason, I guess blood gets redirected to more important parts at that moment :D
This drove me completely crazy, I couldn’t wait any more, I wanted to cum with a dick up my ass, I told him to make me cum. He reached down, took my dick and started to jerk me. It took exactly one jerk for me to start cumming :D
It was the. Most. Intense. Crazy. Violent orgasm I ever had! I though my dick will explode. My asshole clenched around his dick so hard he couldn’t even fuck me, he was just barely inching a bit in and out while jerking me. And he didn’t stop until I was completely finished.
It was indescribable!

I was so fucked! I just laid down, completely happy, with smile on my face from ear to ear :D
He went to the bathroom, got out clothed. I was still laying on bed completely naked and happy.
Got up to greet him. He gave me a peck on the cheek and a grab and a slap on the but :D He obviously knew how to keep a customer happy.

Went into the shower and I was actually proud of my own ass :D I was proud that it took dick so well, that it was such a good little fuck, and that it made me so happy.

Third day of my trip I was all smiles all day :D I can’t wait for the next one. I want to try other positions. Pronebone would be great, to feel more of his body on me as he fucks me. I also want to ride a cock :D
And there’s the matter of a blowjob. I don’t want to do that with a professional, but I so want to go all the way. I want to give oral pleasure, I want to make a dick cum in my mouth. Not sure if I’ll be able to do it, but in my fantasizes I always swallow everything, and drain that last drop. And then get fucked with taste of sperm still in my mouth. I’m such a little slut :D

And there you have it. My first, but obviously not last, gay sex. I’m horny now, off to jerk one out. With something up my but, off course :)

Source: reddit.com/r/gonewildstories/comments/ertzll/my_first_anal_mm