Thanks for stopping by to read, this is the tale of my first time having anal sex with another man.
I was in my early 20's. I, at the time was by all means straight, I dated girls, fucked girls, and loved every minute of it. But from around 17 years old I had gone through the shemale stage of porn, and eventually (I can't remember how exactly) I had moved onto gay porn.
I still remember the fear i felt when watching it, because I knew this meant I was bisexual. I don't think I actually came watching it for a good 6 months. Maybe my way of making it less gay, I dunno. First it was twinks, twinks and more twinks. Then it moved onto daddies fucking twinks, which one of course would assume that I had an obsession with young skinny emo dudes, but then I realised one day that I was actually watching the daddy the entire time. Fuck. I was a bottom.
I had slowly made my way onto the hookup sites. Terrified of being caught I was always on alert, made sure my pics were completely unrecognisable etc.
One hungover Sunday morning I had the usual hangover horn. I made the normally-drunk decision to hop onto my favourite site and waiting for me were several messages since my last visit to the site. I only went on when I was fucked up so there was always a big gap between my replies to these guys.
Having a quick look I could see it was the usual 50+ overweight, small cocked men asking to bottom for me. Not my cup of tea at all. I was slim but relatively muscly, short back and sides with some piercing and tattoos, a bit of body hair here and there but nothing to worry about.
One of the messages was from a guy in his 40's, he looked very well kept and had a tight body, muscles but not ripped (gym fit) and a bit of a tan. His face was showing slightly in the pics but was covered by the camera flash. Fuck it why not.
I sent a reply to his attempt at small talk from 6 days prior and went on browsing the site. The page refreshed a few mins later and I had a message in my inbox. It was him! I excitedly clicked on and opened a new tab up so I could check his pics out again while I read.
He was asking if i was looking to meet and I said yes but I had not done anal before but was keen to try. I had given oral to a couple guys before but it was so few and far between by this point I was pretty much at experience zero.
Again he replied almost instantly. Asking if i wanted to come round some time and we can take it slow. Damn my hungover dick was furious already. I said that I would love that and then asked if he was free now. To my delight, it was a yes.
I asked where he stayed and as soon as he sent his address I felt the urge to close the laptop and never do this again. Luckily I was still a bit drunk, so my lack of inhibitions stopped me from doing that. I said i was going to get the bus as it is on the same route, he offered to pick me up but I said no as i thought that would more than likely make me bottle it.
A long, nerve racking bus ride later and I got to his street. Mouth dry as hell because of the nerves, I jumped into the nearest shop and got myself some juice. I opened the site to say i was a few mins away. When i got to his building he was waiting outside at the door for me. That weirded me out, but I couldnt back out now. We walked up the stairs and into his apartment. Despite the rough area that we were in, his place was incredibly nice.
We sat in the living room and he asked if I wanted a drink, "Just a water please" I barely managed to say out of my even more increasingly drying mouth. I should've asked for a beer to make the whole thing easier. He sat on the couch cornering where I was and asked me what I had done with guys before, I said just some kissing and some head, but never any anal sex giving or receiving. He said that it wasnt a problem and he had been with many virgins before, a bit weird I thought but at least he'll know how to be with me.
He asked if i wanted to go to the bedroom, or alternatively the bathroom, there was a large jacuzzi style bath in there, but I said the bedroom as this was all new enough to me as it is. I took my clothe off in the bedroom while he was strangely absent, had a quick look around to see any signs of hidden cameras and awaited his return. He came through with a condom, a small towel and a bottle of lube.
I just stood there like a deer in headlights, confused and a bit scared. I had been through this scenario hundreds of time with women, but in this case, I did not know how to proceed. It also wasn't til now that I realised he was about a foot shorter than me. I stand at 6'3 so this was of course not uncommon but in all the Old+Young videos typically the daddy dominated the twink in both sex and size.
He almost leapt up at me and his lips locked to mine. He kissed deep and passionately and started sucking me tongue every so often. I thought to myself he needed to calm it down, but then when he lead me to the bed while kissing me and we both fell onto it, I got so so turned on by the kissing when he had me underneath him. The height issue now was not a problem. He was ontop of me and I felt the body heat, I felt his strong shoulders and I felt the fair sparsed all over him. I am about to live out my ultimate fantasy.
He worked his was down my body and started sucking my dick. I was only semi hard at this point but it was hands down the best blowjob I'd ever had. Next thing I know is his dick is now in my face, for a 69. I did what I had done the last fe times, took it in my mouth and essentiially emulated what I believed felt great. He was moaning alot, something I first found weird. I had been told I was great at it, something that made me feel bad for women (who have given me some shockingly bad ones in my time) because having a dick means you know what is great. We continued like this for about 5 minutes, my dick hadn't gotten to 100% hard yet, which I blame on last night s intoxicants.
Eventually we detached and he asked if i had been rimmed before, as soon as he said this i thought fuck, i hope i was completely clean down there! I said I hadn't, but wasn't sure if it was my thing. Without any option he dove down to my ass and stuck a warm tongue right onto it. I dont like this one bit i thought, then, without warning, he made circular motions and my entire body turned to mush, then tensed up, then back to mush. Jesus this was absolute heaven.
He circled and pushed, changed speeds and pressures for what felt like an eternity but in reality was probably only 5-10 minutes. Next was an incredibly cold feeling on my ass from the heat that I just felt, that must be the lube. His fingers were dancing around me tight virgin hole until they started to hint at penetration. I could feel ever so slightly a finger going in, then out, then in further. Before i knew it I felt his knuckles on my cheeks, he had a finger right up there, gently poking around. No feeling of my prostate/gspot yet thought which confused me, I was that ignorant back then that I assumed it would be an automatic feeling straight away. "Well done" he said to me, "You're pretty much half way there," then he slowly took his finger out. "Are you ready?" I nodded nervously. "It's okay, I will go slow."
I was on my back with the small towel slightly tucked under my lower back/ass, he came up to my face level and started his kissing again. I was still not fully erect but then realised that this didn't matter, I wasnt with a girl I was about to get fucked. Erection preferred but not required. My thoughts were interrupted by the feeling of something bigger than a finger tip touching ontop my butthole. Did he just gain some size? It felt much bigger than what I had just had in my mouth minutes before. His dick was about 6 inches, not too thick and cut, a bit like mine.
Still kissing deeply, he slowly started to hump his dick into my hole. I thought it was never going to go in, no way, it started to hurt the more he worked it in, but I knew this would be the case so I powered through. Eventually I felt his entire tip inside the first inch of my ass, thats the biggest part done which felt like a relief. Apologies in advance for the vulgar mention, but the further he got in the more I was worried about shitting myself. I am a straight guy who hasn't openly discussed gay sex with anyone, so no one had told me what I'd feel. Despite realising that all that is happening is something is going in and out of my hole, pretty much like being on the toilet, I still had the worry in my head. This didn't help my case as I was tensing up with the panic. He told me to relax an let him do his thing.
His assurance actually worked and I felt much better lying back and going through the motions. He was about half the way in with his thrusts and I felt him reposition to a more tactile stance. His thrusts were going deeper now and they felt stronger and more controlled. I started to feel his thighs touching mine, with my knees in the air, and his balls slowly hitting against my arsecheeks. He was almost fully in by this point and the discomfort I felt before was belittled by the massively arousing feeling of being fucked. Not just the physical feeling inside of me, but also the general thought of the act itself. I was underneath a grown man and he was pleasuring himself at my expense.
He started to speed up, kissing me ever so often, my lips, my neck, my chest. I kept my eyes closed the entire time, unsure if this was the correct etiquette. It did not seem to bother him, as he kept getting faster but without hurting me with his thrusts. They were strong but not wild. Even faster now and I started to get this feeling in my balls, at least I thought thats what it was, It was as if all of the parts of my genitals, including a new part that I had never felt before, were heating up and tingling. The increase of the speed made this even better now an oh my god this was the elusive prostate I had heard of. I never wanted it to end.
As if out of nowhere his entire body froze up and he made the 'I've just came' sound. I didn't feel it like I thought I would because he was wearing a condom. Truth be told I was actually quite upset because I was really starting to get into it, and the feeling was really getting me off. He lay there ontop of me breathing an sighing.
He asked me if I wanted to fuck him, this wasn't really on my agenda and I also wasn't hard enough i thought. I said no thanks, but he wasn't let down, he just then asked me how the fuck was. "Better than I expected" I said. He seemed joyed at my response an instantly went back down on me. It felt much better than before, but I needed my ass filled again. I was too nervous to ask for a finger aswell, as I had just said no to a request of his. He sucked me until I came and swallowed my load.
When all done I was sat on his bed and started to gather my things from the floor then started getting dressed. He said I did not need to go so quick but I had the post orgasm regret really badly. I could've stayed there and played with him all day, but the conversationw prior to the fucking I could tell that we weren't a good match personality wise.
I left, with the feeling of pride that I didn't need to stop, but also with the feeling of regret that I didn't get the chance to wank my cumming dick while being fucked, but theres always next time.