It was half past one and I had just heard my mother turn out the lights in our house and go into the bedroom. Actually, it was about time for me sleep as well, but I really wanted to jerk off to a hot video I found on pornhub earlier that day when I secretly surfed porn on the bus home from school, and I didn't want to do that as long as my mom was still up. I took the toilet roll from the desk drawer, put on my headphones, but only over one ear, so that I would hear if anyone would come in. I know it's natural for an 18-year-old boy to watch porn, but I didn't want anyone in the family to come in and see me jerking off to gay porn and thus find out my sexual orientation.
As soon as the clip started playing, I pulled my pants down to my knees. I had longed to jerk off while I watching that handsome guy, who looked to be around 20 years old, smooth but still trained, in the middle of four muscular men who took turns using his throat and ass. I got so horny imagining that it was me standing there on all fours and getting fucked by those men, and I fantasised that they would hold me in a tight grip with their big hands and force me to take their big cocks all the way in. As I continued to jerk, I brought my other hand down under my balls and caressed the hole, licked the finger to get some saliva on it and then brought it back and continued caressing, and then let it gently and slowly slide in, but only a small bit at a time, and no longer than about an inch, not so that it hurt.
After stimulating my ass with my fingers for a while, while I fantasised that one after the other fucked me and emptied his load in me, I came and hit both my stomach and the t-shirt, even though I had pulled it up a bit to avoid stains on clothes.
When I went to bed, a thought gnawed at me, a thought I had pondered for quite some time - I will really be able to be fucked as hard and sexy as I fantasise about. Fingers work well but as soon as I tried something bigger it had always hurt. Once I put a condom on a cucumber to test and barely even got the top in before it hurt and I had to cancel. After waiting for a while for the worst pain to subside, and for me to apply quite a lot of lubricant, I tried again and could at least take the cucumber a couple of inches inside. However, it hurt more and was not at all as nice as I had hoped. I wondered if it hurts less with real cocks, but why would it make such a big difference?
I was active on apps for men seeking sex with other men, but had not dared to meet anyone yet since worrying about how bad it would hurt had kept me from daring to do it. I did not want to meet anyone and give the expectations that he would be able to push his whole cock in and fuck me as hard as on porn movies, and then maybe not even be able to fuck me at all, and let him settle for a boring blowjob.
I picked up the phone to go into the app and see if someone interesting had written something to me, but it was nothing particularly exciting, mostly guys I had wrote with earlier when I was horny who wanted more nude pictures, but it had to wait until later. I was just about to shut down when a message appeared in my inbox: "Hey buddy, can't sleep?". I clicked on the profile and saw a man who was actually much older than the ones I usually write with, 42 years old according to the profile, not much more text than his name is Bradley and seems to like outdoor life and exercise according to the few pictures he posted. He looked fairly good for his age, short stubble and brown short hair, with hints of gray. I do not know why, if it was his kind eyes or the fact that he was a man with a lot of experience that I could be anonymous to, that made me entrust myself to him regarding my thoughts. What did I really have to lose?
"Hello. In bed and just thinking about stuff ". I didn't want to be perky and seem desperate. If he wants to hear about my thoughts, he must ask for it himself first. He answered at once.
"So, something special you're thinking about?"
"Yeah then. Might be weird to write to someone I don't know at all, you can tell if you think it's weird. Or just block me in that case"
"Hehe okay, shoot"
I explained that I have never had sex with anyone yet more than a few blowjobs, that I fantasize a lot about getting fucked but am worried that it will only hurt. As soon as I sent the message I felt stupid and shut down the app, worried that it would be an awkward conversation, and fell asleep shortly afterwards.
At breakfast I came to think of my short conversation with the man and picked up the phone. He had responded with two messages right after I put the phone down:
"Hey I absolutely do not think you have anything to worry about. First of all, most people say it feels much nicer with a real penis than both fingers and toys, even though fingers are smaller. You can take it slow in the beginning and find out what you like, and there are tons of techniques and tools to help you out, so don't worry"
Shortly afterwards he had written:
"I actually happen to be a doctor, though not specialised in exactly this area but I know what I'm talking about :) Just let me know if you have any thoughts or questions"
I did not really know what to answer, and quickly put the phone down when I heard my dad come into the kitchen where I was sitting.
Later in the evening I saw that Bradley was online again. There was something about him that appealed to me and made me feel that I could entrust myself to him, but I did not know what to answer, I had already expressed my thoughts and didn't know what more to say. Suddenly another message appeared from him in the inbox:
"Hey, if you want to, and are comfortable with it, we can meet and talk more about this. You can get some products that you can practice with, etc. I do not mean it as something sexual between us even though you seem very handsome, I just want to help you. You can come by the clinic after working hours if you want to and if it feels less uncomfortable :)"
I didn't know what to think about this. It could obviously be some creep trying to lure me over to try to have sex with me, but something made me want to take this chance to get to learn something from an experienced man. I couldn't continue to keep these thoughts to myself, I needed some advice. So I answered and we arranged a meeting at the clinic the very next day.
"Hey buddy, I'm Bradley"
He smiled welcomingly and held out his hand. He was wearing a white coat with a name tag, but unbuttoned with a knitted sweater and jeans underneath. The clothes were tight enough for me to see a clearly marked muscular chest, strong thighs, but also a hint of a belly that bulged out modestly - typical daddy body. Even though he was not my type at all I could not help but think for a moment about what he looked like under his clothes.
"Hi, ehm I'm Kevin" I said and held out my hand, which he took in a firm grip.
We went through an empty waiting room and then directly into Bradley's room.
We sat by his desk and started with some normal small talk, like "how was your day" and he asked me about school, before he brought up what I was here for.
"So, I understand you're a bit anxious about being a bottom for a man, especially men with bigger dicks? I'd say this is a very normal concern and hopefully I can give you some advice and we can try experiment a bit and see how that feels, alright buddy?"
I had not expected that I would try things out there with him, but that he would talk and give some advice. As I said earlier he wasn't really the kind of guy I'd see myself have sex with.
"I thought we could start by me checking quickly that everything looks fine. So we can talk further later about different techniques and so on. Does that feel alright?"
Getting my butthole checked up by a random gay man seemed a little weird, but he was a doctor after all and I thought I might as well just do it since I was there, how bad can it be? And it might be really helpful actually.
"Yeah sure"
