Helping My Roomie With Daddy Issues

He made a point to not look at my face. He held me in his palm and silently stroked me. His dad chose that moment to call, and to my surprise, he answered it and kept jerking me off. He spoke to his dad and I knew that he had been waiting for the call all along.


Our country was a bit slow to catch up with the virus. In March of 2020 things started to go really bad. Our college shut down indeterminately, but me and my roommate, Leon, decided to stick together; we didn’t want to put our families at risk.

Before quarantine, we had lived together for a year. We were used to each other, and I mean, very used to each other. We were comfortable showing our bodies, sleeping naked, and yes, jerking off.

Leon was my age, 20, lithe and dark skinned, he had curly black hair and a pretty face. He was popular with girls, and also a great person. But he was knee-deep in daddy issues. His dad was as overbearing as they come.

In fact, his dad was the reason we started to get closer. With quarantine, we had to stay indoors and jerking off together became more frequent.

We didn’t look at each other. I knew my cock was bigger, and his was thicker and darker, I knew that my head was more bulbous, and his leaner. We noticed, but we didn’t stare. But once we were forced to spend so much time together, things changed. I did watch him cum a few times, the creamy jizz gushing right out of his dick. He would always make the same face and close his eyes.

It was close to the end of the first month of quarantine when he asked to do it for me, not in words, but slowly touching my hand while I jerked and shooing me away, so he could grab it.

He made a point to not look at my face. He held me in his palm and silently stroked me. His dad chose that moment to call, and to my surprise, he answered it, answered it and kept jerking me off. He spoke to his dad and I knew that he had been waiting for the call all along.

He squeezed and ordained my cock, while his dad talked to him on the phone, and him telling his dad he shouldn’t worry. Somehow it was incredibly good, and I shot my load on top of his hand and through his fingers. Leon looked at me and then at my cock, but he didn’t let me go, even with cum all over his hand, a notion that made me hard again.

Leon cummed too, without touching himself, and struggled to hide his pleasure from his dad. He looked as surprised as I was, trying to control his breathing.

Cumming without even touching his cock? Just jerking me off? It was a little past the point of friends just helping each other. He shot three, four times… His body trembling, his eyes closed for a moment. Then he let go of my semi-hard cock.

We cleaned ourselves in silence. But then he made a joke or two and pushed away all the weird thoughts. We sat down side by side, and he talked about his dad, complaining as usual about the pressure of being the only child of a man who expected too much. ‘He talked about you. He really doesn’t like you. He says I should find better company.’

His sincerity startled me. I found comfort in knowing that, while the father had been trash talking me, the son had been stroking my cock.

‘Was that when you came, or did you just enjoy watching me?’ I asked anyway, stung.

Instantly, I had a moment of regret. I shouldn’t have brought it up. Now things were going to be weird again.

Or so I thought.

Leon laughed, and pointed at me, saying that I had cummed all over his hand. I pointed out that his hand had been on my meat, which was kind of the whole reason.

‘Did you like it?’

The question definitely took me off guard. I didn’t want him to assume things, but I nodded, while staring right back at him.

He reached out and squeezed my cock through the fabric of my sweats. I leaned back, surprised. It was happening again. What caused in him this sudden interest? Was it always there and I didn’t see it? Was it just a kink because of his dad?

The most terrifying thought was that his hand was exactly where I wanted. It was so terrifying that I was about to push it away.

Before I could, my cock betrayed me utterly. It woke up so quickly, I could only stare at my own erection, as if it didn’t belong to me, it shouldn’t be mine. It was. I bit my lip as he squeezed me in his palm. Leon let out a sigh.

‘So big,’ he said, and it seemed like it was involuntary. He looked guiltily at me and seemed truly sorry. I placed my hand on top of his and helped him squeeze me harder. He gained a little more confidence. ‘Want some help?’

We didn’t talk for a dozen minutes, and Leon’s hand was all wet and creamy for the second time that day.

We both seemed to agree things had gone too far, because the next day, we didn’t even talk to each other.

He wasn’t weird, just silent. We only talked past afternoon when his dad called again and they screamed at each other.

He apologized to me. I felt bad for him. A few minutes later, his hand was wrapped around my cock, making me cum like crazy. Leon watched me with a big smile.

That time, when I was done, he washed his hands and then pretended nothing had happened. I expected one of us to just be too weirded out by the whole thing and just give up, him going back to his previous roommate, or me going home.

Instead, what happened was that Leon grew more and more used to my cock. I even tried to jerk him off some times, but he usually just took over and told me to relax. During the next days, I was so used to his hand around me, and his voice telling me I was big and thick, and urging me to cum, that if I spent a day without him, I felt frustrated.

What Leon liked the most was to milk my cock while talking to his dad over the phone. He was never more agreeable with his old man than when my cock was spurting some cum on his hand. Sometimes he looked at my jizz very closely, making me think he was about to lick it, but he never really went for it. And I wanted him to do it. I began to feel jealous of his own dad for the time he spent on the phone, and I just wanted him to focus on me, my cock, all the time.

Then, one day, during one of those heated calls where I knew that Leon was about to burst some anger with his dad – the man wanted to know if Leon was still studying, every day, even if college was out because of the pandemic – I sat down on his bed and removed my shorts. I took his hand and made him jerk off. Leon started to calm down. I could see gratitude shining in his eyes. He actually grew calmer.

‘It’s my cock you should be worried about, not him.’ I whispered. Leon smiled. ‘Tell dad I will take care of you now.’

His smile disappeared. He looked at me for a few seconds.

‘Keep going,’ he whispered back. I could hear his father talking, but couldn’t understand.

His hand resumed his strokes. He was pressing me harder in his fingers. He closed his eyes and leaned back on me.

‘I’ll make dad’s boy busy with my cock all day. Tell him not to worry, that his son is all grown up now and ready to make me proud. I’m gonna cum on dad’s precious boy. You’re mine. Not his.’

Leon was listening attentively, and as he leaned more and more, I could see that his erection was leaving wet marks on his shorts. My friend was ready to lie down on top of me, pushing his body and heat against me, while his hand was still stroking me. He had to end the call, because he couldn’t talk anymore.

‘Say more, please,’ he said. I could barely recognize that mellow voice.

‘Just think about what he would say if he could see you now,’ I said. ‘He would be so angry at you. You’re just so bad. So bad. He used to be so proud of his son, and now you’re my bitch. You love to make me cum.’

‘Fuck!’ he said loudly. His whole body shook with the strength of his orgasm. I had to hold him down. He even squeezed my cock so much it hurt, as if, for a moment, he forgot what he was holding on to. He shook a few more times, then stopped, trembling slightly. I held him tight. I was so focused on him, I only now realized I had cummed too.

This time, Leon licked my cum from his fingers, while we both recovered our breath. To my surprise, he seemed to enjoy the taste.

I could only stare. It was really my cum that his tongue was so eagerly licking from his fingers? He even let out some happy sounds.

It was hard to ignore our current position, not only literally, his body still resting against mine, but also how our friendship had crossed the line. Also hard to ignore was the fact that I was enjoying too much watching Leon savor the taste of my juice. It awoke some deep desire I didn’t know I had, to make him eat my cum every day, and much more.

Everything came into play to make Leon the object of my dirty mind. I enjoyed the thought of breaking and bending to my will the guy whose father was so determined to control, the guy who was more popular than me and more intelligent, the guy who seemed to have everything, he was the guy who was milking my cock and licking my cum.

That’s not to say that Leon came easily to this role. After getting a bit of my taste, he tried to ignore me, but we were locked in this place by ourselves. A few hours later, he was the one who sought me out, who interfered in my studying hours to complain about how his dad wanted him to leave me and come back home. It was obvious to me what he wanted. I wondered if it was as obvious to him, or if Leon didn’t quite grasp how much he was begging me.

The role-play was the same. I was stealing him from his dad, there was nothing that the old man could do to stop me from ruining his precious son. Leon loved to hear those things. He came so willingly that he didn’t even protest when I took off all his clothes and lay him down on the bed. He was spread out and naked. His legs so wide open that his anus was exposed, a tight pink hole.

Leon was so unused to that sort of thing that he came all too soon. I didn’t let him abandon his role yet. He was to be obedient, and think about pleasing me instead of his old man. He apologized to his father aloud, as if the man was there.

I couldn’t believe how hard I was, and there was more to it than just the experimenting stuff and curiosity. My one year roommate was spread out in front of me, and I wanted nothing more than stick my cock inside him and pound his ass. He looked good like that, specially because he was doing it with so much need, like he needed my validation.

I kept the game alive. I told him that he could pretend all he wanted, but behind his dad’s back, he was just a slut and a cocksucker. Because of that, Leon was determined to suck my cock.

He didn’t know how to. When he first put the head inside his mouth, he suckled for two seconds… the next time he lasted five seconds. I enjoyed watching the agony and indecision in his eyes while he looked at me. I encouraged him, calling him a good boy, saying that I was going to raise him right. The words came so easily, it felt so right, but at the same time, I was blushing from the ridiculousness of it. Each time he put my cock in his mouth, he lasted a little longer, until he accepted his fate.

Leon’s mouth was so warm. It felt weird to think of him like that, but there it was. He was sucking me. It was kind of funny that his father hated me, and now I was making a cocksucker out of his son. I could see why Leon was enjoying himself so much.

I watched as the realization reached Leon’s eyes that he actually enjoyed sucking cock. His mouth started to work faster and better, his tongue lolled around my veined dick, going through my balls – he particularly enjoyed the balls, which astounded me. As he put them in his mouth, I asked what he thought his father would think of him if he could see his son at that moment. Leon actually moaned. It made me chuckle to be able to actually see so much of him, so see him so exposed to me. Leon must have felt the same, because when he stared at me, I saw insecurity and fear, but also a good deal of amazement. It was like he saw me for the first time.

I decided that, from now on, I would always hunt for that expression in his eyes, that admiration. Then I surprised Leon again by cumming all over his pretty face. He had tasted my cum already, so it was easy for him to deal with it. I was more shocked at that sight, at my own pleasure of seeing him all covered with my semen. Nothing could ever express the message better, that he belonged to me.

His cock gushed cum all over my bed. He looked so tired later. The after was my weakness, because I didn’t know what to do to make it all okay. It was his job. Leon could choose to end it all, to be offended, to call his dad and say he would leave me. Thankfully, he just silently walked away and cleaned himself, and later he treated me normal, and I was glad that I could rely on him.

My family would ask me if I was okay and if I would rather just come back home to stay with them. I could never express how much I wanted to be left alone. They didn’t know about my newfound part of me.

Thinking about Leon’s relationship with his dad, I asked myself if my own dad would be disappointed if he knew about what I was doing. Still, I think that his disappointment would have been nothing compared to Leon’s father. The things I did to his son weren’t what a father would wish for his only male child. But I guessed the man had his own share of guilt. And Leon seemed to enjoy himself.

I felt no guilt as I convinced Leon to give up his ass. It started with just a finger, but a finger can do wonders, this is true not only to girls. I brushed and pressed my finger so much in Leon’s ass that he started to ask and even beg for it. When I started to use my tongue, Leon had accepted his fate once again. He knew I was only preparing him, teasing him, but his ass was mine.

The call from his dad that made everything better came a bit before sleep time on a Sunday night.

Leon started to ignore his dad, cause now he had better things to do, higher priorities. His dad was furious that was being ignored. He seemed to want a claim over his son that no dad should. Leon was supposed to be only an extension of his dad’s needs, it was painful to watch Leon’s face as he tried not to scream out of frustration. As I watched from the other bed, Leon started to stroke himself, because he knew that I would help him out. I went over to him and lay beside his body. His hand found my cock, and instantly he was able to endure his father better. I whispered in his ears that he was mine to do as I please. It was the first time that he kissed me. I was so surprised, I dropped my act for a moment, just letting him stick his tongue inside. However, I wasn’t surprised that I enjoyed the kiss so much. He was a bit out of breath when he told his father to leave him alone. He turned off the call, threw away the phone, and mounted on top of me. He kissed me for a long ass minute.

‘Fuck my ass, sir,’ he said. ‘I want it now.’

He was all about surprises that day. Being called sir was a whole new sensation.

“What would your father say?”

As an answer, he rubbed his hard cock on my belly.

I did not need much convincing. I wanted to fuck him from behind, and used as much lube as I could, telling him to open up his legs.

‘Show me how much you want it,’ I said. He arched his back and pushed his ass up. Then, he used his hands to stretch out his butt and show me his hole. I stared at the tight little thing, feeling a bit guilty about thrusting my big cock inside. I would love to see him in pain from that. It would be so sweet. ‘Tell me who you want to please more in this world.’

‘You, sir. Uhhh.’

I thrust my tongue inside, against the resistance which was only a reflex and that made my entrance a sweet victory. My mouth did all it wanted with him in that position. But I could feel he wanted more.

‘Talk about your father, Leon. You know you want to.’

‘Oh. I’m more yours than his. He’s just an old man. You’re my daddy now.’

I froze for a moment. My cock jolted from hearing that word. I was never into the daddy stuff, but it made perfect sense in this situation.

‘Say that again, slut boy.’

‘You’re my daddy now. You took me away from him. He is nothing to me.’

I could not believe my happiness. If I didn’t fuck him now, I would probably cum and waste all of my cream, instead of filling him up. So I pressed the head against his tight hole and watched it stretch all the way until it engorged my cock.

Leon moaned like a girl, and he seemed to be in pain. But he also spoke. ‘Fuck yeah… Oh, fuck… like that.’

At that moment, I did wish I could make his father aware of his surrendering, just so he could feel how much his son was not his anymore.

I wasn’t intending to go all the way, but Leon urged me.

‘I can take it. I can take it, daddy.’

So eventually I was balls deep. I could feel everything that went on inside of him, my cock pulsing against his walls. It was amazing to watch my cock disappearing inside, and the sound of my balls against his ass, and the way he would moan when I was getting in, and sigh when I was on the way out.

I tried to last as long as I could. But I shouldn’t have worried, because he took my cum in his ass, and my cock didn’t even grew soft. I fucked him for a good fifteen minutes more, and there was no talking, only the sound of my thrusts, each one making my claim on him stronger.

I fucked him in my bed too, the very next day. And he sat on me on the couch, riding me like a true cowboy. I guessed he was as surprised to the sensation as I was, my claiming and his surrendering. He was loud, and I worried about the neighbors, and tried to shush him. He loved to moan. It sounded like a painful cry, but it was the way he liked it.

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5 thoughts on “Helping My Roomie With Daddy Issues

  1. Studman says:

    I agree with skyreader, this is a very well written piece, and it is disguised in a sort of reportage format—this is what happened. But what readlly happened is two guys learned a lot about themselves by engaging in intimacy in a way that was new to both of them. And they both liked it, and grew into it, becoming accolytes of their unique gay sexual activity. Really well one and I’d love to read more from this writer.
    Speaking of that, why don’t you give writers’ credits?

    • Pen says:

      Darn 🔥 🥵 🔥 🥵 🔥 🥵. Leon has truly found his new daddy. What 🔥 🥵 scenes first teaching him to suck cock and then getting his virgin 🍒 popped and loving the seed. ❤️ 😍 💖 ❣️ 💕 💘 this story. Wish Leon was here to play.

  2. skyreader says:

    Superbly written with a hot theme: Getting even with his overbearing Dad by sexually pleasing his roommate.

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