I had sex with a man for the first time and now I think I’m fucked in the head [MM]

I’m a 28yo man, fairly fit, and I’ve been told by more than one girl that I’m quite good looking. I’ve been curious of what it would feel like being with a man for as long as I can remember, but until now I had never acted on it. I’m sexually attracted to women and I’ve had many girlfriends, but I’ve always had this nagging feeling that I might be missing on something that I’d enjoy.

So last week I chatted up a guy on Craigslist and I told him about my situation. I told him that I had never been with a man (even though I’ve masturbated with toys many times) and that I wanted to try. We exchanged some photos, he asked me a full pic with body and face and I obliged him. The mere fact of taking nude photos of me for a complete stranger excited me to no end. In return I asked him to send me a pic of his dick. I realized I was not really interested in how the guy looked, I just wanted to see what the dick that was going to pop my man cherry looked like.

He sent me a photo of his decent-sized tool (I would say between 6 and 7 inches, decent girth) and from the little else I could make out it was attached to a hairy fat body. I didn’t give a fuck.

We chatted on kik for a couple of days and he asked for more pics. I asked him what he liked and tried to look pretty for him in my photos. I went as far as taking a naked pic of myself on my balcony, where I risked being seen by my neighbors, just because he mentioned it was one of his kinks – even though he didn’t ask for it explicitly.

I couldn’t understand what was going on in my head. The more I thought about this guy, the more I felt the overpowering need to be treated as a slut. I was horny all the time.

We finally decided to meet in a bar in the city center. I arrived half an hour early and sat at the bar, waiting for him. Unless he decided to show up with his dick hanging out of his pants I had no way of recognizing him, so I just had to wait for him to approach me.

He arrived almost an hour late. He was fat as a whale, probably close to 350 pounds and maybe 6 foot tall. He had a full beard, and by any standard he could be considered ugly as sin.

We chatted a bit and he asked me if I was sure about what I was doing. He told me that if I wanted to back out, this was the moment. He had a friendly tone but he seemed to be sizing me up. Maybe he was trying to understand if I was just a tease or if I was really serious about this, I dunno. I simply told him to take me to his place. I think my pants were about to explode.

When we arrived at his place (a very nice and well kept apartment btw) he asked me if I wanted something to drink, but maybe due to the beers I had already had while waiting for him, or to the fact that most of my blood was in my nether regions I couldn’t think straight. I simply replied “you decide”. And to make it more clear, I added “about anything, tonight you’re in charge”.

His tone and demeanor changed almost instantly. He stood up, and facing me he unzipped his pants and extracted his flaccid penis. I instantly got to my knees and took him in my mouth.

It was the first dick I had ever touched (apart from mine obviously), the first dick in my mouth and, as I was going to discover very soon, it was going to be the first of many firsts for me that night.

I sucked him off for a couple of minutes hoping not to be too bad at it. He got hard almost immediately so I was probably doing a decent job. The sensation of having a penis in my mouth, per se, was nothing special. The guy was fairly clean, there were no funny smells or anything. But what was really getting me going was the idea of being submissive to him, of giving him pleasure and just being a slut. That, and the fact that he was fat and ugly. Something must have short-circuited in my head, idk what the fuck was going on.

We moved the party to the bedroom, where we stripped naked and I resumed sucking him off. He seemed to be enjoying it, while I was going down on him he explored my body with his hands. He then told me in a commanding tone that he was going to fuck me. I didn’t say anything. I just obediently turned around an all fours, stuck my ass up and waited while he grabbed a condom and lube. He lubed me up and shoved his dick inside me without even asking me if I was ready. I recoiled from the surprise and the sudden excruciating pain, so he bent over and pressed my head down on the pillow with one hand. The guy was way bigger (and way heavier) than me, so I really couldn’t move even if I wanted to (I didn’t).

He plowed me doggy style, grunting and sweating, and it fucking hurt. I was being filled in a way no toy can and I had the sensation that I was being ripped apart. After a few minutes of pumping and grunting he pushed me forward and laid all his massive weight on me. He kept on fucking me like his life depended on it. He was seriously hurting me, both my ass (for obvious reasons) and the rest of my body. I tried to move a bit to find a more comfortable position and he must have taken it as a sign that I was trying to push him off, so he passed one arm under my neck and pinned me down. I could hardly breathe.

After another minute or so of this agony, he stopped pumping. He still held me down with his weight and started fumbling around his dick with his free hand, while the other arm was still around my neck in a sort of reverse headlock position. He told me that he couldn’t come with the condom on, so he was taking it off.

I barely had the time to register what he had said that he entered me again with such a violence that I could not help but scream in pain. For one weird second I thought, this must be fucking painful for him as well. I was not thinking straight. After fucking me for what seemed forever he let out a growl/scream and flooded me with his cum. He really fucking flooded me. He alternated grunts, pauses and violent thrusts until he had fully unloaded in my ass.

When he finally finished cumming his body went limp and he rested all his weight on me, sweating and panting like a goddamned animal. I couldn’t breathe.

After a while he thankfully got up and went to the bathroom. I checked the situation down there, and I was oozing a mixture of cum and blood and in the process I was staining his bed sheets. When he came back into the room I asked him if I should go or spend the night, and he said “you decide”. It seemed that he couldn’t less care one way or the other.

I decided to spend the night there, I was in no shape to go anywhere. He fell asleep almost immediately, so I went to the bathroom to assess the damage and clean up, in case he decided to fuck me again during the night.

I went back to bed, but I couldn’t sleep. I was overwhelmed by what had happened. I was in a strange bed with an ugly fat bear of a man loudly snoring next to me. I was hurting badly. But mostly I was horny as fuck.

After a couple of hours I tried to wake him up with a blowjob, but I only managed to have him sleepily telling to get the fuck off him. I tried again at dawn, and this time he obliged and fucked me again, and this time he lasted a lot longer and it hurt even more. After he finished in me (bareback again) he basically kicked me out.

Now two days have passed and my asshole still hurts, and I’m waiting for him to contact me again. If he doesn’t I’m going to message him. Or maybe I’ll just go to his house and see if he’ll let me in.

If you’re interested I’ll let you guys know how it goes.

Source: reddit.com/r/gonewildstories/comments/6c6w2w/i_had_sex_with_a_man_for_the_first_time_and_now_i