Helping My Son Relax
Returning home from Dublin and getting back to my everyday routine was tough, when all I wanted to do was go to my father and say "Can we do that again?!" The fact that we wanked together, side-by-side, still blew my mind! If I had my way, we'd be doing it every single time we saw each other now.
Yet, I knew things were different for Dad. For one, he wasn't gay. What happened was a "spur of the moment" kinda thing for him, I had no doubt, fueled by the sounds of the straight couple fucking across the wall from us. My uncle Kris and Mia were off to Paris now, however; probably keeping someone else up with their unrestrained sex sounds.
I've been a horny lad for years now, ever since I started going through puberty and discovered porn, so thinking about sex was nothing new to me. Yet ever since Dublin, it was becoming a bona fide OBSESSION! I couldn't focus on anything else, least of all my schoolwork. I'd even started eyeing some of the sexy blokes round school, which was new for me, since I usually only had eyes for daddies.
Daddy-boy porn was always my most-viewed category, and that didn't change after meeting my father. Quite the opposite, it only increased. Now, I spent all my free time locked in my room, wanking for hours at a time, even neglecting some of my homework, which I never used to do.
I knew I wasn't special when it comes to this; most of the boys at school made jokes about being obsessed with porn, and they came to the conclusion that the only solution to the problem was to start shagging. Easy for them to say! They were all straight (or pretended to be) and their options were much more plentiful… not to mention the fact they didn't need to worry about the horrors that might come with doing anal.
I looked up "how to have gay anal sex" on the net, and for once I wasn't looking for porn but rather a helpful tutorial. It was surprisingly difficult to find anything useful! It all either went over my head, or it was so obtuse and medical that it sounded like it had no real-world application. We had some sex ed in school, but it was also very general, and it offered next to no information useful to gay teens. Among my peers, both boys and girls, the consensus seemed to be: "sex ed is useless; you just gotta do it, and once you've done it you'll know what it's like."
So with that in mind, I strolled through Soho one Saturday afternoon. I didn't have a date with Dad – I didn't even know where he was – I just liked strolling through the gaybourhood whenever I could, looking at all the gay men around me and envying them for having more experience. Until, I bumped into a familiar face.
"Paul, hi!" I said to my dad's neighbour; the first man whose cock I ever sucked.
"Hello, good to see you again. It's been a while," Paul said as we stood chatting in the street. It was a sunny day in late March and all of Soho seemed to be out enjoying the weather. I looked down at Paul's grey trackies, showing off his cock like always. I wasn't the only person to notice it either; several guys in the street eyed his bulge as they passed us by.
"Yeah, I've been all over the place," I said, "I went to California for Christmas and then Dublin for St. Patrick's Day, in between taking care of stuff at home." I tried making myself sound as adult as possible, not even mentioning school.
"Taking care of stuff, huh?" Paul smirked. "Good lad. I might have some stuff for you to take care of."
As he said that he grabbed his bulge, giving it a shake and making it obvious that he was freeballing. I admired his brazenness to do this in the street, as well as his directness. Then again, I'd already sucked his cock right after meeting him at Dad's Halloween party, so there was no point in pretending I was hard to get.
"We– We can do that," I tried to be as cool as possible. Next, I even surprised myself by putting my hand on his bulge and giving it a squeeze, feeling his cock through just one layer of material. A gay couple who sat outside at the nearby Caffè Nero spotted us, and just smiled in amusement. Normally I would feel mortified, but instead I felt encouraged; so I rubbed Paul's cock some more, stroking it through the thin cotton of his sweatpants.
"Let's head upstairs," Paul said to me with a grin, and five minutes later we were up in his flat. We'd walked past my father's door on our way up and it felt weird to be passing it on the way to a hookup... or possibly even getting fucked for my first time.
"Have you been sucking a lot of cock since the last time we met?" Paul asked as soon as we were inside his flat, dropping down his sweatpants and exposing himself to me. Once again, he wore a metal cockring, which is probably why his bulge was so obvious in the street.
"N– No," I admitted, salivating at the sight of his cock.
"Well let's make up for lost time," he suggested, stroking his dick which got larger with each stroke, pulling back his foreskin until his cockhead was exposed. I dropped to my knees and quickly had my lips around it. This time, there was no chance of Dad walking in on us… which was kind of a let-down, frankly. The pervy side of my brain wanted my father to see me sucking cock again. I wanted him to hear Paul's moans of "Mmm, yes," "Good lad," and "Just like that!"
Dad's neighbour was now fully hard and fucking my face, holding my head with both hands and going in deep, all the way to the back of my throat. I gagged and chocked a few times, but I'd seen enough deep-throating videos to know what to do.
"Good job, Son," Paul said. He knew talk like this turned me on!
"Mmm, Daddy," I moaned while sucking on his cockhead, swallowing the precum leaking out of it before going back and deep-throating him again for several minutes.
While sucking dick, I reached in my joggers and started playing with my own boner. "Take your clothes off," Paul instructed me, so I took off everything I had on, including my socks and underwear, leaving it on the sofa. "Get on the couch," he said next.
I sat down, and Paul turned me over until I was on my knees with my arse pointing out, my elbows leaning against the backrest. He squatted behind me, and a second later I was getting my first rim job.
"Oh, god!" I shouted. I'd expected it to feel good, but not this good! I had no idea; it was difficult to imagine someone else's tongue on your hole until you've actually done it. And Paul was a pro, I was certain of it! He was older, and had probably hooked up with countless men and boys in his life. "He's the perfect person to do it with," I figured.
I continued to moan and shout as Paul's tongue went in circles around my arsehole, finally going it. "Relax, Son," he said to me as he rimmed me and I tried to do just that, feeling my hole open up in the process, granting him access to venture even deeper.
"Is this your first time, Son?" he asked, before shoving his wet tongue inside my arse again.
"Yes, Daddy," I let out a high-pitched moan.
"Enjoy it, baby."
He spread my cheeks open, kneading and squeezing them, when all of a sudden my phone started to ring.
"Answer it," Paul said to me. I was surprised to hear him say that, until I looked at my phone on the couch and saw my father's picture and the word "DAD" flash on screen.
"Hello?" I answered my phone, still remaining in the same position.
"Callum, hi. What're you up to?" Dad's voice said just as his neighbour's tongue went back inside my teenage hole.
"Umm, not much," I replied, trying my best to sound normal, which was NOT easy with Paul tongue-fucking me.
"Where are you? I talked to your mom and she said you might be in Soho."
"Uhh, yeah, I'm – uff – I'm close to your flat," I said. If he only knew.
"I'll be back home in about an hour. Wanna drop by?"
"Su– Sure," I said, just as I felt a new sensation: a finger going up my arse. It felt very different than Paul's tongue; it was much more uncomfortable and it made me let out a loud "Oww!"
"You okay?" my dad asked.
"Yeah, I'm – mmm – I'm fine," I said as Paul continued to finger me. "I'll see you in a bit."
"See you soon, Son."
We hung up the phone and I turned around to see a shit-eating smirk on Paul's face.
"You like that?" he asked, his finger still thrusting inside my arse. By now I was getting used to the sensation, and my hole was opening up even wider.
"Mm, yeah," I nodded, dropping my phone and closing my eyes. And then…
"Do you want Daddy to fuck you, Son?" Paul asked.
"You just gotta do it, and once you've done it you'll know what it's like," went through my mind. There was no point in prolonging it.
"Yes," I nodded, and felt a second finger of Paul's slip inside me. It took more getting used to, but a few minutes later I felt ready. Paul got some lube and applied it to his cock, as well as my hole. As I felt his fingers lubing me up, I started to feel REALLY nervous, but I did my best not to show it. "This is it!" I told myself, as I tried to brace for impact.
Paul's cockhead felt nice and warm against my hole. "Open up," he said, and I wasn't sure if I was open or closed. All I could do was try to relax, but I couldn't tell what was going on back there.
Then, I felt a pain beyond what I expected. "Ow, ow, ow!" I yelped, and felt Paul pull out a little bit.
"Just relax. You were more open than this when I was rimming ya."
I tried to do as I was told, but it wasn't easy. As soon as I felt Paul's cock slide in past the cockhead, I yelled out in pain again. "Stop. Stop!"
Paul pulled out of me and I felt immediate relief. I started to tear up and I did my best to fight it. I wasn't even sure why I was so close to crying.
"I gotta go," I said, reaching for my underwear and putting them on.
"Are you okay?" Paul asked, taking a few steps away from the couch.
"I'm fine. I just need to meet my dad," I said, avoiding eye contact.
"Listen… I hope I wasn't too rash or anything. You seemed ready…"
"No it's fine, I just told my dad I'd go see him," I insisted. I got dressed and a minute later I was on my way out of Paul's flat, with a polite goodbye but without a kiss.
"do u have a minute to chat? x," said a text from Josh's mom Gemma that Saturday afternoon. I was surprised to hear from her and I texted back, "Sure."
After a couple of minutes of smalltalk over the phone, we got down to the main reason for the call.
"Listen, I was just wonderin' if you and Callum ever… if you ever talk about sex or anyfin' like that."
"What do you mean?" I asked. I was out shopping in Camden Market and I walked away to a spot where I could have a bit more privacy.
"Well… lately 'e's been lockin' 'imself up in 'is room even more than usual. 'E's in there wankin' round the clock, it's clear as day. I've tried bringin' it up delicately, but 'e just gets embarrassed and tells me to shut up. Which is understandable, granted. I wouldn't even say anyfin' but it's startin' to affect his schoolwork, like. So I fought you might have more luck. You're both blokes and… and 'e didn't know you when 'e was little, so 'e might feel more comfortable."
"Okay. Listen, Gemma, I'll see what I can do," I said. Callum's mom obviously didn't know anything about what happened between the two of us in Dublin.
"Fank you, Josh! Are you home? Cos I fink Callum went to Soho as well."
"No, I'm in Camden. But I'll give him a call."
After a few more minutes, I hung up and called our son, arranging to meet him at my flat an hour later.
When I arrived home, I saw Callum sitting on the stairs right outside my flat, looking like an abandoned puppy.
"Are you alright?" I asked. He almost looked like he'd been crying, and it struck me as weird that he wasn't even listening to music or playing on his phone while waiting for me.
"I'm fine," he said casually, but it looked like he was trying to put on a brave face.
"Listen, I got a spare copy of this key, maybe I should let you have it," I said as I unlocked the door. As soon as we were in, I fetched the extra key and gave it to my son, kicking myself for not doing this earlier.
"Thanks, Dad," Callum smiled, already looking a bit better.
We sat in the living room and I got us some cider – which here was an alcoholic drink. I kicked my shoes off and put my feet up on the table. I always had a very relaxed relationship with my dad and brothers, and I wished I could get there with my son as well. Of course, after what happened in Dublin, many might say that our relationship was VERY relaxed. However, I knew fully well that talking about your feelings was often much more difficult than having a wank with someone. There was clearly something bothering Callum, and it might be related to what his mother mentioned on the phone. Either way, I wanted him to feel comfortable to open up about it.
"I have a date later tonight," I said. I wanted to stir the conversation in a sexual direction, and this seemed like a safe place to start.
"Oh, that's nice," my son said, taking a swig of cider.
"Yeah. I met her on Valentine's Day. She's a bit young so it probably won't go anywhere serious, but she's one hell of a fuck."
"What about you?"
"Wha– What about me?" Callum asked.
"Are you dating anyone, crushing on anyone? Hooking up with anyone?"
"No, no I'm not," he shook his head, bringing the conversation to a dead end. I tried to think of a way to revive it, but it was Callum who spoke next.
"Dad... How old were you when you had sex for the first time?"
"14. A girl in my class, same age. She ended up pregnant when she was 16, but it was another guy, we weren't doing it by that point anymore."
"Yeah. At least I guess unwanted pregnancy's not something you need to worry about," I smiled. "Then again, there's other things."
"Yeah, that's what's bothering me. I don't know…" Callum left his thought hanging mid-sentence.
"You don't know if you're a top or bottom?" I tried to guess. It seemed like a dilemma someone in his position might have.
"No. I mean, I'm pretty sure I'm a bottom. But… How can I be a bottom if I can't take a cock?"
"So you've tried?" I asked my son as we made eye contact.
"Yes. I knew it would hurt but not that bad."
I took my drink and went to sit right next to Callum, putting one arm around him just like I did in our bed in Dublin.
"I can imagine it's not easy."
"No. And like… What if I'm too tight? What if I can never take it?"
As soon as the words were out, Callum started blushing and he looked away. I could understand how he was feeling, and I wished I could let him know that there was no need to feel embarrassed.
"Listen, I can't speak for every person in the world, but I'm pretty sure there's no such thing as 'too tight.' You just need to practice and get used to it. That is, if you even want to do it. You're never required to do anything if it doesn't feel good."
"But how do I… how do I practice?"
"Well, they make toys for that. I've seen tons of stuff. There's literal sets that you can buy."
"Yeah, well, I don't have anything like that," Callum said, looking down again, peeling the label off his empty cider bottle.
"Well why don't we get you some?" I suggested, patting his knee. "We're in Soho, there's a sex shop on every corner. We can get you something right now."
"Can I even go inside a shop like that?"
"I'm not sure, to be honest. Are you allowed to legally have sex with adults, but not to go inside a sex shop? That seems fucked up. Either way, we can pretend to be a couple, that'll make you look a couple of years older."
"How do we pretend to be a couple?" Callum finally smiled.
"Well, you can hold my hand and tell me how much you love me, and call me sweetie pie and honey bear and darling," I said in an exaggerated lovey-dovey voice while holding Callum's hand and kissing his face repeatedly until he started laughing and pushed me off of him.
Ten minutes later we were in a sex shop right on my block. On the street level, the store sold underwear and rainbow flags and T-shirts, and the downstairs was where they kept all the sex toys. If anyone noticed Callum's age, they didn't say anything. He and I discreetly examined some dildos and butt plugs, laughing at the ones that were literally larger than my arm.
"See, no such thing as too tight," I laughed. "If someone can take THAT, you can surely handle a dick."
I paid for five dildos, all in different sizes, all made from the finest, most expensive material. It wasn't until we were back at my flat that I realized I should've bought some lube as well, since Callum couldn't use them without it.
"I have some lube you can take," I said. Luckily, I kept several bottles at home, all of them open and partially used.
"Thanks," Callum said, taking the bottle I handed him. In his other hand he was holding the smallest of the plugs we'd just gotten, like a child examining a new toy.
"Do you wanna try it on?" I smiled.
"Yeah, you can go to the bathroom and pop it in," I said casually. I wanted my son to know that this was no big deal. If he tried it right here and now, I could be here for him if something went wrong. The plug was hardly bigger than a man's finger, and I was fairly certain Callum could handle it.
"Umm, okay," he said. He took the toy and the bottle of lube and disappeared into the bathroom.
I waited a few minutes, pacing around the flat and tidying up. After a while, when it started to feel like Callum had been in the bathroom for too long, I decided to go knock on the door.
"Everything okay in there?" I asked.
"Kinda. I dunno. I'm fine."
"Umm, that doesn't sound too convincing. Anything I can do?"
"No, I just can't get it in."
"What do you mean, what's the problem?"
"I don't know."
Since this didn't seem to be taking us anywhere, I said, "Can I come in?"
A moment of silence was followed by an "Okay," and I walked in.
Callum stood at the same spot where I'd caught him sucking a man's dick at my Halloween party. This time, Callum was in his boxer briefs, his sweatpants down to his ankles. He was holding the butt plug in his right hand, as if it were a foreign object he had no idea how to use.
"Is it too big?" I asked, knowing that that couldn't possibly be the problem.
"I don't know. I tried shoving in it, but it just won't go. It hurts too much," my son said, sounding frustrated and disappointed in himself.
"Let me see, do you have any lube on it? You gotta put more than that," I said when I noticed that the toy hardly had any lubricant. I took the plug from Callum and lubed it up myself. "There."
"Dad? What if I am too tight?" Callum said nervously.
"Listen, Son, there's two sides to having sex, whichever way you do it. There's the physical one – the things your body does – and there's also the mental one. I know it sounds easier said than done, but you gotta relax. Whenever we do anything for the first time, we tend to get anxious. Sex is right on top of that list. Men have been taking things up their ass since the beginning of time. I promise you, you do not have a freak asshole that is too tight. You're probably just nervous, which makes you clench up."
My son laughed, and I could tell he felt more encouraged after my little motivational speech. And then...
"Do you want me to help you?" I said, faster than I'd had time to really think about it.
"Wh– What do you mean?" my son asked.
"Well, if it's hard to reach back, I can try… inserting it for you."
"You'd do that? I mean, it is kinda awkward doing myself, but…"
"Don't worry about it. If you want me to, I'll do it," I said generously. My son and I looked at each other's eyes for a moment longer, until he turned around, poking his ass in my direction.
I squatted down behind Callum, facing his meaty asscheeks that were filling up his black boxer briefs.
"I'm gonna pull down your underwear now," I said, pulling down the back of it. It wasn't until I did that that I realized that Callum's dick was hard in the front. He must've boned up while playing with his ass.
"Damn, that's one nice ass," I thought. As wrong as the thought was, there was no denying it; I was in awe of my son's impressive behind. The sight of it even… it even gave me a twitch in my shorts and an involuntary chub.
"Okay, ready?" I asked. I'd inserted toys in women's asses plenty of times, and with the size of this plug I knew that it shouldn't be a problem, as long as my son learned how to relax.
"Okay, go," Callum gave me the green light.
"Just breathe," I advised him as I took some of the lube that was on the butt plug and smeared it on my fingertips. Next, I brought my fingers to my son's ass and reached in between his cheeks, locating his hole and rubbing some lube on it. As I did so, I felt it pulsing, as if kissing my fingertips. A tiny bit of my index finger even went inside, making sure to get enough lube in there as well.
Callum's hole was certainly tight, but there was no reason for him to worry about being "too tight." After massaging it for a few seconds, I could already feel it relaxing. I noticed my son's hard cock bouncing in the front of his underwear as well, which could only be a good sign.
"Okay, in we go. Just relax, Son," I said as I brought the plug to Callum's asshole and gently slid it in. Just like I thought, the size was perfect; it went in with next to no resistance.
"FUCK!" my son suddenly shouted. At first I was afraid that something was wrong, that I'd somehow hurt him, but then I realized there was a completely different reason for the outburst: Callum was cumming! Without either of us touching it, my son's cock was blowing a load inside his underwear; his pearly-white jizz seeping through the black fabric.
For a moment I was quite taken aback. If this is what taking a small butt plug did to Callum, my son could rest assured that he was a bottom! I smiled, feeling happy for him. With my fingers still holding the hilt of the plug, I pulled it out just a tad, before inserting it deeper again.
"HOLY SHIT!" Callum yelled out even louder, his voice echoing in the bathroom. He was having potentially the strongest orgasm of his young life, and I was here not only witnessing, but directly contributing to it as well. I pulled the plug back and forth a few times, effectively fucking Callum's ass with it. After all his nervousness and insecurity, my son deserved this.
After he'd flooded his underpants, Callum pulled his cock out and continued to shoot my grandkids all over the bathroom floor. Even I – a decent cummer – was impressed by the amount of sperm his 16-year-old balls could produce. "That's my boy," I thought proudly, pulling the plug once again before pushing it all the way in, making Callum's cock shoot out a few more spurts of cum.
Leaving the toy safely inside my son's ass, I got up. We were both speechless; Callum could hardly control his breathing. I started to laugh out loud and patted his back with strength and pride.
"I told you you could make it, Son," I said, and I went in to give my boy a big strong hug. Callum let his head rest on my shoulder and he finally did what I'd been telling him to do: relax. We stayed hugging in my bathroom for several moments, my half-boner pressed against my son's stomach. I didn't even care about the fact that his cock was dripping cum all over my bare leg.