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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 istanbul travesti 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.
“Then you can start by taking off your pants and underpants and take a seat in the chair”
He showed with a gesture towards a chair in the corner that I think gynecologists have, where you lean back and fold up your legs. I undressed and sat down on the chair, wearing only a sweatshirt.
Henrik sat down on a stool and rolled forward so that he was sitting directly in front of me, told me to lay down backwards while he folded up my legs.
“From the outside, it looks like it should. I’m going to carefully insert my finger inside too see so istanbul travestileri that everything all good”
I didn’t reply but just watched as he pushed lubricant out of a tube on his fingers and lubricated my hole gently. The thought struck me that it was a little strange that he was not wearing any gloves, when a finger slowly slid inside.
“How does this feel?”
“You said you usually put fingers inside your butt when you jerk off and so on?”
“Ehm well yeah”
“We can test gently with one more finger and you can tell how it feels”
I closed my eyes and took a deep breath as I felt another finger slide inside me. It did hurt a bit, but it was still alright. I let him touch my prostate with his fingertips, and felt his deep exhalations against the skin down there.
“Seems like it’s going very well. I thought we would try this one “
He held up a perfectly smooth black dildo. “It’s very smooth and not that long either. And therefore it will not hurt as much as many other toys. I think it might be easier than a finger, even though it’s thicker”
I felt the dildo slide in, and just like he said it didn’t hurt at all.
“Feels good doesn’t it?” He said with a smile. “This is probably the most stretched out you’ve been without pain. It’s almost like you’re taking a medium sized cock”
When he said that I felt my dick getting harder, which made me stressed. Out of pure instinct, I took a hand down and held it over. Bradley smiled.
“Hey don’t worry buddy, it’s all natural to grow a boner when the prostate is stimulated. I’m actually pretty hard too” Bradley said before he stood up so that I could see a clear contour of his dick under the jeans. It seemed very thick, and pointed down to the right trouser leg. At least around 8 inches, a really big one.
“It’s actually good that you get horny, then it will be easier and more comfortable to stretch” he added with a smile, and then gave me a wink. “Ok I have an idea. Do you have any porn videos you like that you can watch on the phone? You can use mine”
He gave me the phone and without thinking I went in on pornhup and found the clip I found the other day, with the young guy who got group fucked.
“Wow, that’s hot. I guess you’re fantasising about being the guy in the middle?”
I do not know why I felt shy to answer. I lay in front of him with a boner, and let him stick a dildo inside me. But he was right so I replied with a shy “yeah…”
“Yeah I get that, it’s hot. Sexy men fucking him really deep with their big cocks. Is that the kind of cocks you want to be able to take?
“Then I think it’s about time to switch to the next toy. This is a dildo that feels very similar to real skin. It’s thick and a little veined, but I think you can handle it. I’m going to be careful so you stretch slowly, okay?”
I immediately became very nervous about how big it was, but trusted that Bradley knew what he was talking about.
“Ok now, look at the screen, look at the guy on the left there and think about how much you want his cock”
He held up the screen in front of my face so I couldn’t look down, and then felt him press his face against my ass, licking my hole. I gasped, it felt so good and so sexy at the same time. His stubble rubbed against my butt cheeks while his tongue caressed the hole, and sometimes he pressed the tip of his tongue inside. I do not know for how long he licked me, maybe a few minutes, all I thought about was that I did not want him to stop. He put my hand around my cock, and moved it back and forth, instructing me to wank. I kept jerking off and couldn’t help but moan.
“Is it nice buddy?” I heard him say
“Hehe good. You have a really sweet ass”
The next thing I remember is how the top of the dildo penetrated me, just one inch though. It hurt and I gasped.
“Schh, lay still one moment. The whole top of the dildo is inside you. Let it stay now while you take a few deep breaths”
It did not take many seconds before it stopped hurting, and Bradley let the dildo gently slide in some more, only about half an inch at the time. I listened to his panting, and saw on his body language, that he was also jerking off.
“Shall we go even deeper?”
“Well, I don’t know travesti istanbul if it will work…it’s quite painful”
Bradley thought for a moment, then he said “we will test another thing. Close your eyes!” Then he put a blindfold over my eyes. I wondered what he would do now, but was so horny that I felt that it didn’t matter. He had to do what was necessary to make me stretch more.
“Think about you being the guy in the video. That you lie here in the chair and get fucked by the man with the biggest cock, while another of them stands here where I stand so that you can suck his cock at the same time”
Suddenly I felt him putting his cock heavily over my face. I gasped, clearly felt the smell of his cock, felt it caress my lips, felt a drop of precum on my lower lip. It made me so horny and I wanted more, I wanted to taste his cock, so I opened my mouth for him, and immediately he inserted his cock into my mouth.
“There you go buddy. You enjoy the taste of cock, don’t you? Now relax” Bradley said and pushed in the dildo at least another inch, which made me gasp. But it did not hurt, I just felt very filled up
“Good boy, now almost the whole cock is inside you. You are very good at being a bottom”. At the same time, he also pushed his cock deeper into my mouth and down my throat, so deep that I felt his pubic hair and belly against my face.
“Wow! Open up your throat boy, just like that. Does it feel good?”
Because I had my throat filled with his cock I could not answer, but just nodded eagerly.
Bradley laughed “Good. Do you think you can take something even bigger?”
I was not at all sure about that but was so horny that I nodded anyway. I wanted more!
Carefully he pulled the cock out of my mouth, and at the same time pulled the dildo out of me. I saw nothing and wondered what he would do to me.
“Take a deep breath” Bradley said, and in the next moment I felt how my butt was being filled again, and this time it was even bigger than before but softer and warmer. And when it slid all way in, and I felt his hairy body against me, and heard him moan, that I understood that he had pressed his cock inside me. “Schh, good boy, let it stay. I promise to pull out before I cum. Lets stretch you a little more “
Now I could barely move my cock without cumming. I loved being so submissive, to lie here and be taught by an experienced daddy how to take big cocks.
“Damn, you’re doing so well buddy, does it feel good?”
And it sure was really nice. Just to lay back and enjoy being completely handed over to Bradley, so I just nodded.
Suddenly the blindfold came off, and I met Bradley’s gaze as he stood in front of the doctor’s chair, and I could see drops of sweat on his face. He had thrown off his doctor’s coat so that his muscular arms were clearly visible through the sweater, which began to show clear patches of sweat all over his chest.
“Mm it’s so great to fuck you. Your little butt is so tight, I’m amazed that I can push all my 8 and a half inches inside you”
I was getting so turned on by him being so horny and hearing him breathing even faster. “Oh I’m about to cum. Do you want daddy to cum over you? Huh? Do you want me to pull out my big cock and cum all over you? “
I did not even have time to nod before he did as he said. His breathing became even heavier until he moaned loudly while he sprayed over me, it kept pumping out all over my stomach, my sweater and in my face. Three or four large squirts came over me, and the last two hit me right in my face. I instinctively reached out my tongue and licked it. It was so hot, and I started take up as much of his cum as I could with my tongue, while I felt him pushing his cock back into me again. The thought of me lying here completely covered in his cum while his cock probably continued to pump out even more inside me made me cum right away.
Bradley smiled “wow, big load from you as well buddy” and winked.
Bradley drove me home. Before I got out of the car, he handed me his business card. “Just text me or send an email if you want”
I nodded, gave him a hug and then got out of the car. Before I closed the door he said
“Hey you, I thought I’d let you know – if you are curious to try out something like what we saw in the movie at some point, I know some men with nice cocks who I bet would be up for it”
I smiled and closed the door, and heard him drive away behind me.
As I walked towards the house, I thought about the offer, and what it would be like to let several daddies fill my holes with cock, and thought “well, why not?”
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