My Sissy Son – Part 1 by CumCrazedCanuck

A gay adult story: My Sissy Son – Part 1 by CumCrazedCanuck ,
This first part is a little long because I had a lot I wanted to get through to properly begin the story. Future planned chapters will be more to the point. Hope you enjoy, please let me know if you want me to continue.
As my euphoric haze began to fade and my vision came back to me fully, I continued to look down at my son’s face. His glazed, messy, cum-splattered face. His eyes were closed lightly, as he began to lick his lips and “Mmmm” with delight. As he released my drained cock from his grip it rested on his cheek and he turned to kiss it again. I slumped back further on the desk and all I could think was “My God. How the fuck did we get here?”But to explain that, I have to go back to the beginning. Back to the painful memories of when this pandemic first hit.

What’s most important is that you understand that before this whole sorted affair started, we were a perfectly normal family. Jason was a normal high schooler, with decent grades and good friends. My wife was a regular Mom, with a good job and a great social life. I was a regular Dad, with plenty of hobbies and a nice, safe future. But that all changed when this stupid virus came and destroyed everything.

See COVID took my wife from us. A perfectly normal 46 year old woman with no health conditions to speak of. She got it very early on, before many of the restrictions had been put in place. Within a few days we had her in the ICU, but they couldn’t do much for her. Not long after, she was gone. I’ll spare you any more of the details because honestly it’s too hard to think about. All I’ll say about it is that it was the hardest thing I’ve ever gone through, and it tore me apart.

In hind sight, I really didn’t handle it well. I took leave from work and ended up trying to drown my sorrows for a while. When I did start working again, from home obviously, I put in little to no effort. I know now that I was severely depressed, and I should have sought help. But beyond all that, I also know now that my biggest mistake was that I wasn’t there for my son. As hard as it was for me to lose a wife, what I failed to realize is that Jason had lost his mother as well. I didn’t see it until it was too late. Until I’d already failed to be a father. We were together in the house, in lockdown, all day every day, and yet we didn’t talk much. I couldn’t.

If there’s one thing I regret above all else in this whole mess, it’s that; my failure to pick myself up and be a man when my son needed me.

I’m saying all this because I think it’s important. I think it directly affects what happened in this house. I think it affected Jason, how he is now. Or maybe not, I suppose I’ll never know. All I know is the day this all started for me was anniversary of my wife’s death, and that can’t be a coincidence.

So it had been just over a year that we were isolating, just the two of us. Every day felt the same. Menial chit chat at the breakfast table, then off to the den to work, while Jason did his online school or gaming or video chats with friends and whatever else he did in his room. He spent all his time in there. I honestly didn’t ask him about much of it because there was never anything interesting to know, and he didn’t have the inclination to share anyway. When I logged off work I would start dinner, and call him when it was ready. Some days he would stick around with me in the family room, maybe watch a movie or on very rare occasions play a card game or something. But generally speaking, every day was the same old thing on repeat. But this day was different. This day was the beginning of something very new.

I was having a rough time getting through work just because it was the anniversary and all. So I ended up in a chat with my boss around 2pm, and she offered for me to take the rest of the day off. I thanked her and logged out after the conversation. When I took my headset off I heard what sounded like panting, or crying maybe, coming from down the hall towards the bedrooms. I stood up and headed that way, calling out as I walked “Hey Jay? You Okay?”. The sounds stopped abruptly. “Jay?” I asked again. No reply.

As I reached Jason’s bedroom I saw his door was open. I peaked inside but he wasn’t there. Looking down the hall I then saw that my own bedroom door was open. Odd, I always keep that closed. I approached the door and saw Jason sitting on the side of my bed, with his back to me. It looked like he was fumbling with something on the side table, my wife’s side table. He heard me come in and spun his head to face me.

“Sorry. Sorry Dad, I… I just…” He began to say.

“It’s alright Jay. Don’t worry about it.” I said calmly, hearing the distress in his voice. I knew there was something wrong. “Were you looking for something of Mom’s, or…?” I asked quietly.

“Yeah, kind of, I guess.” He replied. “I don’t really…”

I cut him off again. “I get it.” I said quickly. I made my way closer and sat on the end of the bed. “Only reason I keep that stuff around is just to hold something of hers every now and then.” I looked for a response in his face, and saw a small smile. So I continued “You know, that table is only thing of hers that is still exactly how she left it.” I explained. When I said that, Jason’s expression dropped a bit.

“I’m sorry Da-” he tried to say

“No, no, I’m not saying you can’t touch it.” I jumped in again saying. “Not at all. You have every right to her things as much as I do. Seriously, it’s all good.” I said trying to ease his mind. But while the words I was saying we’re true, I also knew in the back of my mind that I didn’t really want him to go digging in that side table. One of the drawers was just full of her underwear, so it’d be kind of weird if he looked through that. But there was something else that I knew was in there, hidden in the back of the first drawer. It was a gift I’d gotten for her a few years ago, for her to use whenever I was away on business or even just out for the night and she felt the need. It was a purple dildo which was actually a perfect replica of my own dick. Not that anyone would know that if they saw it, it would just look like a normal dildo, because honestly I have a real average looking dick, but we had used one of those clone kits to create it, so she could always have me whenever she wanted, even when I wasn’t around.

“Well, that’s good to know Dad, thanks.” Jason said, snapping me out of my nervous thoughts.

“Is there anything in particular of hers that you were looking for?” I asked.

“No… Just.. umm.” He stumbled. “I mean I like looking at this photo of you two” he said, picking up a framed photo of my wife and I.

“Hmm, yeah, me too.” I agreed. But I could clearly tell there was more he wasn’t saying. He put the photo back down and suddenly his body language changed. He dropped his head and slumped his shoulders.

I put my hand on his shoulder and asked “Son… Are you okay? Did I hear crying before I came in here?”

“Crying? No!” He answered quickly. “I wasn’t crying, I…” He trailed off.

“What then?” I puzzled. “It’s totally understandable if you were. It’s a tough day. Hell my boss just let me off work early because she knows what day it is.”

“I know.” He said. “I mean yeah, I’m sad today, for sure, but not just because of Mom. It’s lots of things.”

“Like what? Tell me.” I said in a sort of begging tone.

He looked up at me with something in his eyes, sadness? Pain? Maybe guilt? Then he immediately looked back down again, staring at the floor. When I, too, looked down towards the floor I caught something in my gaze as it moved. Jason’s forearm was tight against his body, and I saw his track pants looked a bit off. There was a bulge, quite a significant bulge, in the crotch area. I hadn’t seen it until now, but I realized that he was trying to hide an erection. I instinctively removed my hand from his shoulder and turned slightly away from him.

In an attempt to ignore what I’d just seen, I said “You know you can tell me anything that’s on your mind Jay”. But I think he knew I’d just spotted his boner.

I saw his eyes close in my peripheral vision, and then he let out a light scoff and said “I doubt that.”

It actually hurt to hear.

Now I had a decision to make. How do I handle this? The last thing I want is for my son to think he can’t talk to me. I will not fail him again. So do I just try to reassure him that I’m here and I’m listening or do I straight up address the elephant in the room?

I took a gamble and turned to face him directly and put my hand on his shoulder again.

“Hey.” I started. He looked up into my eyes. “I am always here for you. No matter what. No matter what you’re going through, or sad about, you are never alone. I promise you that. You can tell me anything. Seriously. Anything.”

I thought it was a very sincere little speech, but his head dropped again and he simply said “Are you sure?”

“One hundred percent” I replied without hesitation. Then after a brief moment of thought, I played my gamble. “Even if it’s about that” I added, gesturing to his crotch, and the still hard tent pole.

I could see the embarrassment creeping into his face, and knew I had to continue to reassure him.

“Whatever it is.” I said “Your secrets, your truth, are safe with me. Always.”

“Even if it’s really weird? And I’m… I’m a freak?

“Hey! You’re not a freak Jason.” I said sternly. “You’re a seventeen year old guy, on a bed, with a boner.” I gave a light chuckle after.

He looked up at me again, and this time I saw clarity in his eyes. Relief even. I had broken through.

He laughed too, ever so slightly. “I guess so.” He conceded. “But one, I’m almost eighteen. And two, … There’s a lot more to it than that.” He added.

“Like what?”

“Honestly I really don’t think you’d understand.”

“Try me!” I challenged him. “I just might surprise you.”

He looked in my eyes again, and I remained calm and tried to keep my expression inviting. Inside though, I was quietly panicking. Is my son about to admit to something terrible? Has he done something unforgivable? Have I been ignoring him and his needs for too long? What have I done to him? He was about to speak, and it was all I could do to just shut up and listen.

“I do miss Mom. A lot. Obviously. But that’s just… Every day. I mean, it’s been a year, yeah, but honestly today isn’t any different from any other. I miss her the same as I always do.” He explained. I kept quiet and just listened. “The thing is… I also miss all the other people who are still here, and I just can’t… be with them. Ya know?”

I nodded in agreement.

He continued. “I mean, I get why we’re doing this isolation shit but it’s so frustrating! I miss the guys. I miss being with them. I miss…” He trailed off again. His voice had gotten a bit shaky and I could tell he was getting emotional.

“I get it.” I chimed in. “I know you’re close with your friends. It’s been really tough lately.”

“Tough? It’s not just tough. It’s…” He failed to finish his sentence again.

“It’s what?”

“It’s… it’s… like hell… for me.”

“Come on. It can’t be that bad.”

“It is!” He chirped. “You don’t get it. I need to be with people. I need the contact. I… I feel like…” Again he couldn’t find the words.

“Like what?” I said, genuinely puzzled. I honestly didn’t know my son was the type of person to need physical contact so much.

“I feel like I’m starving. I… I crave it. I need it. I need to be with them.” He admitted.

“Wow.” I mumbled, a bit confused about what to say. “Okay, well, I mean I know you like to hang with your group, but-” then he cut me off.

“Not just hang.” He said. “BE WITH”. He emphasized.

Not really sure what that meant exactly, I hesitated to speak long enough that he continued.

“I mean… Like… I miss being… in physical contact.”

“Okaaaay. So like partying and–”

“No, like… I miss the physicality”.

“What, like sports? I didn’t think you were really into spor–” cut off again. I was still so confused.

“No!” He said, clearly getting frustrated. “I miss… I miss…”

“What Jay?!” I questioned. “Spit it out!”

“I miss their cocks!” He blurted.

Wait. What? What the fuck did my son just say to me? That was my only thought. I was stunned into silence. He put his face into his hands, seemingly holding back tears now.

“I miss having their cocks.” He said again. “In my hands. In my mouth. On my body. I… I crave them. I have this… this insane desire. It overwhelms me.” He continued speaking into his hands.

All I could think was Holy. Fucking. Shit. My son was admitting to me that he was gay. He was coming out of the closet to me right now. This is huge. This is a very important moment for him; for us. And it’s a good thing. I mean, he’s being a little vulgar about it but still, it’s a great thing that he’s telling his truth. DON’T FUCK THIS UP.

“Son.” I started, with a calm, loving tone. “Are you telling me that you’re gay?” I asked plainly, but trying to inject a hint of enthusiasm in my voice.

He raised his head from his hands and said “No! Well… I mean, yeah… but no, not really.” Okay, now I was very confused. I quirked an eyebrow, which compelled him to continue.

“I’m telling you that. Oh, I don’t know. It’s just… it’s like you said, I’m seventeen and I’m just… all hormones right now. I can’t control any of it. You know I’ve had girlfriends, obviously. I love women. They’re beautiful. If anything, I admire women more than anything. I only said that about the guys because before all of this they were the ones I would be with the most. I mean, we all did stuff with each other, and it was…” He trailed off again. He saw my still confused expression and spoke again. “It’s 2021 Dad. Straight, gay, whatever… doesn’t really matter so much these days. I am what I am, and I enjoy being with all kinds.”

This was sort of a revelation for me. I never really thought about sexual relationships that way, and I certainly didn’t know my son felt that way about it.

“Well, shit. I guess I am out of the loop.” I admitted simply. I thought about for a second and honestly none of it bothered me in the slightest. “But if you think I wouldn’t understand that, then it might surprise you to know your old man has a pretty open mind.”

“Uhm, that’s not really the part I was worried about” he said coyly.

“Oh?” I muttered.

He sighed heavily, hanging his head again, glancing towards his crotch, where his dick was STILL hard.

“If you want the truth.” He paused, with a great hesitance. I could see the wheels turning in his mind. Then finally continued. “This… is the part I don’t think you’ll understand.”

Then he proceeded to hook his thumb under the waistband of his track pants, and pull it first upwards, to clear the tip of his hardon, and then downwards revealing the first 3 inches or so of his lace-covered cock. My jaw dropped, and I’m sure my eyes bulged out of my head and I looked down at the white panties stretching over the bulbous head of my son’s erection. Instinctively, again, I moved away from him slightly and then turned my head so I wasn’t looking at my son’s dick for too long.

“What? Jay! Please!” Was all I could utter, while I put my hand between my eyes and his crotch in an attempt to indicate he shouldn’t be showing me that. He quickly pulled the waistband back and covered up.

What was he thinking? Why had he pulled out his dick for me to see. He could have just as easily pulled the strap of the panties up out of his track pants if he just wanted to show me that he had them on. But he’d deliberately showed me half of his hard dick, which was pretty clearly visible through the light fabric.

“Sorry.” He said, with shame in his voice. “But these are what I actually came in here for.”

If I thought him trying to come out of the closet to me was shocking, this was surely a mind-bender. This wasn’t just surprising, but it was sort of a violation of my wife’s most personal things. Then again, why had I even kept them? Maybe I liked having them around still, but it’s not like I ever put them on. But again, I knew I wanted to tread carefully with Jason. I had just told him not 2 minutes ago that any secret he had would be safe with me. And I meant it.

“So…” I began slowly. “So, you’ve been wearing some of Mom’s things? Her… underwear? Is it… is it how you feel close to her?”

“In a way. Yeah.” He admitted. “But it’s not really about Mom. It’s about… me. How it makes me feel. I like to feel the way she felt, when she wore them. It feels nice, on my skin, on my… dick. It makes me feel good.”

“It feels… good.” I repeated. Beginning to understand. I thought about how this conversation had all gone down and it started to make sense now. Something dawned on me and I just thought out loud “So before I came in here, you weren’t crying, you were…”

“Yeah.” He admitted plainly. “Like I said… all hormones.” He added.

“Ahh.”

“It’s just… you’re always in your den until at least 5pm. I thought…” He said, not finishing his statement yet again.

“No, that’s… fine. I mean, we all do it. I do it too, obviously, how could I not?” I cracked a laugh. “But I would prefer if you did that in your own room. Don’t think that’s too much to ask”

“Absolutely!” He agreed. “And I totally meant to go back there. But as soon as I slid them on, it’s just… it’s like it just activated instantly and I couldn’t help it.” He gave his dick a hearty grab through his pants and kind of waved it a bit.

I thought that was a bit odd, but a part of me was sort of glad of his freedom in that moment. Like he had his own pride about his sexuality and his big hard dick. There was something oddly satisfying about his attitude, and how he’d gone from what seemed to be shame, just a minute ago, to this sense of pride. I couldn’t help but chuckle again.

“No, I totally get it.” I said genuinely. And I did. It was all making sense now. The poor kid was just horny, and ended up succumbing to his kink and then couldn’t help himself. I stood up slowly off the bed and said “I was a teenager once too. And uhh… I know what’s it’s like to be walked in on, so I’m sorry for that, son.” I took a step back towards the door. “Tell ya what, it seems like you still need to take care of things so I’ll give you some privacy. But maybe next time, just uhh, take it back to your room, eh?” And with that I turned to walk away.

In the next few seconds, a multitude of thoughts was going through my mind. My son had just admitted to being gay with his friends, but he also claims to love women. So he’s what? Bisexual? But he also enjoys wearing women’s panties while he masturbates? What does that mean? He’s a… crossdresser? Is that the right term? Or is it more than that? Does he actually want to BE a woman? Maybe I am too old to understand this. Too out of touch with kids and their lifestyles. I tried to shake it all off and just accept that it’s different from how it used to be, when I was going through my teens. But there was still one thing I really wasn’t getting that was nagging at me. My curiosity got the better of me, and before I reached the door I turned around to ask.

“So… Jay, just one thing.” I started, waiting for a response.

“Yeah?”

“The first thing you said was that you miss your friend’s…” I didn’t want to say the word cocks, so I hesitates and went with “…dicks.” his expression changed back to one of reluctance.

“I just… I don’t quite understand what that has to do with your mother’s underwear. Is it… is that what you think of when you…” I gestured with my hand below my waist.

“Uhhm.” He said. His shoulders slumped one more time and he let out a sigh. “Okay… I guess I’ve said this much, I might as well tell you everything. Full disclosure?” He asked, as if I would say no, never mind. Then he continued. “It’s not just the panties I came in here for.”

He turned back to the night stand and pulled open the first drawer. As he pushed some tubes of moisturizer and sewing supplies out of the way and reached further into the back of the drawer my heart almost stopped for a second. Oh shit. Does he know what’s in there? Does he know his Mom used a dildo? Has he seen it before? Has he touched it before? Good lord, has he USED it before?

As his hand found its prize and he slowly pulled it out from behind the other innocuous items, my fears were realized. He was indeed gripping the purple replica of my dick. He unfolded his fist and let the toy rest in his open hand, displaying it for me.

“This. This is what I really wanted.” He explained sheepishly.

“Oh.” was all I could muster at first. An awkward silence followed. “You… you know about that eh?” I finally said.

“Yeah, I found it a few months back actually. Sort of around the same time I started using the panties.”

“I see. And… so… what do-” he cut me off

“I really like it. The way it feels. It makes me feel… Oh I don’t know.” He said while gazing at the toy longingly. He lifted it to his face and turned it so the tip was facing his lips. “There’s just something about it.”

“I think… I understand now.” I said lamely. But he wasn’t even listening to me now. He was enraptured by the dildo.

“The feel of it. It’s so soft, but hard. It almost feels like the real thing.” He touched his lips to it. “And it’s just the perfect size. I mean, a lot of the guys have really nice ones. Cory and Sheldon are definitely special, but this… this is on a whole other level. I’ve never wrapped my fingers around one so thick.” As he said it he proceeded to grip both hands around the shaft, leaving just the bulbous mushroom head visible. “So deliciously thick.”

Then he leaned his head forward and slid his front hand back on the dildo revealing more of it while at the same time sticking out his tongue to touch the tip. His eyes closed as his lips wrapped themselves around the head of the dildo and I watched it disappear inch by inch into his eager mouth. I stood there stunned for a moment. I couldn’t believe he was doing this in front of his own father. I mean, if this were some female sex doll no boy would start sucking her titties in front of their parent. What in the hell is going on? Is he truly entranced by fake penis? Is he THAT horny of a young man? This is all too much.

I couldn’t say anything. I certainly didn’t have the heart to tell him that it was actually a clone of my erect penis that he currently had lodged in his mouth. Speaking of my penis though, that’s when I realized something had changed in the last few seconds. I could feel the pressure of my pants against my dick. It had started to grow. It must have been because my son was talking about it, or the clone of it anyway, so admiringly. Surely this wasn’t a reaction to what I was witnessing with my eyes. Though, now that I watch him, and that shaft glide smoothly into his mouth, it’s clear that there’s a level of skill there. A part of me wonders… No! What the fuck. It’s wrong to even think that.

“Uhhm.” I finally muttered, breaking my horrible thoughts and the silence at the same time. “I’ll just…” I whispered as I left the room, closing the door almost all the way but not shutting it.

I stood outside the room against the wall for a minute trying to catch my breath as it were. My mind was reeling from what had just transpired. I didn’t know what to think. And now my own swelling cock was confusing me more than anything Jason has said, or done. As I stood there leaning against the wall I couldn’t help but hear him now. I realized it was that same sound I heard from before I’d first walked into my room. It was the sound of muffled moaning. The sound of a person with a stuffed mouth, in ecstasy.

I really don’t know what compelled me to do it; confusion, curiosity, perhaps envy? But I turned back to the door and silently opened it enough that I had a view of my son through the crack. He was indeed stuffing his mouth now with the sex toy, deepthroating it in fact. At the same time he was rubbing his palm on his hard dick. His pants were down now, but the lace panties still covered his cock. From where I was standing it looked to be a fairly impressive cock too. I saw half of it earlier through the thin material, but now that he was rubbing the entire length of it through the sheer fabric, I could see from head to balls, and it was impressive. Longer than mine in fact, though, as he said, not nearly as thick. His cock head was really straining the panties waistband as if it wanted to burst through. As he continued to rub and suck and moan, I could see a wet spot forming in the fabric where it was stretched at the tip. It was probably several minutes, but it seemed like mere seconds before he was writhing uncontrollably and soaking his panties as he climaxed. He never actually took his cock out of them, even to finish. Just before it happened he’d shoved the dildo as far as it could go in his throat and held it there while the wet spot in the fabric painted itself like a work of art. I wasn’t sure if he’d done that just to muffle his cries of ecstasy or because that’s just how he likes to finish. Either way, it was eye-opening and sort of incredible to watch.

But I shouldn’t have watched that. What the fuck was I doing? Again, I was lost in thoughts that I knew were wrong. I should have been controlling myself, but I just had to see. Maybe that’s where Jason gets it from. His inability to control his urges. He gets it from me. Just another way I’ve failed him.

I heard Jason release a big sigh of relief, presumably after pulling that thick shaft from his throat and coming down off his orgasm. That’s what snapped me out of my thoughts and I realized he had just stood up to leave the room. Shit! I speedwalked as quietly as possible down the hall back to my den where I work. I made it in time to shut the door quietly behind me before I heard him close his door to his bedroom.

Holy shit. What just happened? I had to gather myself again. I made sure the door was locked and went over to the window to look out in the backyard. That’s when I felt a slight pain in my crotch. I put my hand on my pants and realized my dick was no longer just swelling, it was now fully hard. It was straining against my jeans, and I had to shift it to avoid more uncomfortableness. Fuck. Why the fuck? What is wrong with me? I just watched my son masturbate… No… I spied on my son masturbating, and it made me hard? This can’t be. It’s not right. I tried to think logically about it.

“Okay, it’s not like I’m any stranger to porn. Lord knows I’ve needed it for the past year. So, that was just basically like porn right? It just didn’t happen to have any women in it. Nothing wrong with that. It’s not like I ever exclusively watch lesbian porn. Men are involved. That’s what sex is. There’s men in sex. Hell I’ve been known to peruse a good cumshot compilation every now and then, and that’s just dicks cumming. On faces, on tits, on pussy, on panties! Not really IN panties though. Fuck.”

As I was thinking about this I then caught my hand rubbing myself through my pants.

“Fuck. Now this is happening.”

I couldn’t stop myself. I had to do it or I knew I’d be thinking about it for the rest of the day, and probably night.

I sat down at my computer and opened it. Immediately my mouse went to my browser and I typed in my usual porn site. As it loaded I unzipped my pants and freed my hardon. I had to get the thoughts of what I’d seen and talked about earlier out of my head so I quickly scanned for a video with a busty mature woman and clicked to watch. With that inspiration on the screen it only took minutes until I was emptying my seed into a wad of tissues and found myself also sighing in relief.

My head began to clear and I felt enormously better, like a weight had been lifted off my shoulders.

“See?” I said to myself. “It was no big deal. It’s not like he even knew I was there. Nothing to worry about.”

A few hours later Jason came into the kitchen for dinner. I wasn’t quite done preparing it, so he sat at the island with his phone while I finished up. There was sort of an awkward silence at first until I spoke up.

“Hope you’re hungry!” I said

“Starving actually, yeah.”

“Well there’s plenty here. And I’m sure we’ll have leftovers for lunch tomorrow.”

“Sounds good.” He said nonchalantly. “Smells good!” He added.

“One of your faves right? Chorizo scramble.”

“You bet! Anything Mexican is delicious.” He said, scrolling on his phone. “Especially Die-” he stopped himself.

I’m pretty sure he was about to say his friend Diego’s name. Another uncontrollable sexual comment. Well I suppose he stopped himself from saying it, so there’s some control there. But still, who talks like that to their father? I was beginning to wonder if we’d opened a door to a new phase in our relationship. One that likely couldn’t be closed. I want my son to be comfortable with me, obviously, but there is such a thing as too comfortable. Then again, if he’d said one of his girlfriends was delicious would I would I still be feeling awkward, or would I probably just envy his youth, and move on? It’s not really any different I suppose. Either way, this might be dangerous territory we’re in now. I want him to be open, but do I really want to hear it? I’m not so sure.

I decided to ignore the comment and just serve up the dinner for both of us. As I did that though, Jason put down his phone and put on a bit of a serious tone.

“Dad, I just wanted to, uh, apologize. Again. For earlier.”

I was willing to try to not really bring it up or pry again, but it seems Jason was interested in talking about it.

“No need son. Honestly. If anything I should be the one apologizing. I don’t think I even knocked before I walked in.”

“Well it is YOUR room.” He admitted.

“Right.” I laughed. “Still. I know what it’s like to be ‘caught’ by a parent. It’s not fun. So, I’m sorry for that. And I promise it’ll never happen again. You’re fully entitled to your privacy in this home.”

“Thanks Dad. I… I appreciate that.”

“Of course.” I said, then gestured to the table as I picked up the dinner dish. “All set.”

Jason took his seat and then lifted his head towards me. “So… it uhh, happened to you?” He asked.

I laughed again. “Yep.” I looked at him and hesitated for a moment, but then figured why not regale him with the story. Perhaps it’ll put him at ease and let him know it happens to the best of us. So I continued. “Your Gramma walked in on me once when I was 15 or so. Literally caught me with my pants down. I had my back to the door, thank god, but I was looking at some pictures online. When I heard her come in, I had a choice; do I try to close the browser window, or cover my dick. Back then the internet and the computers in general were really slow, so I figured I was probably screwed on that front, plus who wants their Mom to see their boner right? So I tried to cover myself.” I wasn’t sure if I wanted to say the next part, but he was listening with interest, so I just kept going. “Trouble was, I was basically at the point of no return at the moment she opened the door. And that last motion of trying to get my shirt over my dick sort of… set me off.” His eyebrows raised at that. “I ended up cumming in my shirt just as Gramma came around to see what I was doing.” He let out a hearty laugh, and I figured he was getting a kick out of the story. “Funny thing is, to this day I still don’t know if she actually knew what was happening at that moment, because… she didn’t leave. She actually sat down on the bed beside me and asked why I was looking at naughty pictures on my computer. Then she saw that my pants were down, and guessed it at that point. She gave me some little speech that I don’t remember because I had just had an orgasm in front of my own mother and wasn’t listening to a single word. Aaaaand then she left.” Jason laughed again.

“That’s hilarious!”

“Yeah. It’s funny now. But it wasn’t when it happened.”

“Ohh man, I can’t believe that. You must have been so embarrassed.”

“Sure was. But you know what, it never happened again. Gramma always knocked before entering, after that day. And I will too.” I ensured him.

“Well thanks Dad. But honestly, I’m not too embarrassed by today. I’m just picturing Gramma’s face when she walked in on you.” He chuckled again. “But it’s not the same with you and me. If anything, I feel kind of good about it. It’s sort of freeing, to have you know more about who I am. I just wanted to apologize again for, you know, being in your room, with Mom’s things and whatnot.”

I had to admire his attitude. Even if I felt awkward about it all, the fact that he didn’t helped ease my own concerns.

“Well, like I said, don’t worry about it. As far as I’m concerned this entire house is our shared space, and her things are your things.” I said. Then I thought for a second more while he nodded in response and took his first bites of dinner. “In fact, why don’t you keep that toy of hers.” I added.

He looked at me in surprise. “Really?”

“Yeah, why not. It’s not like I’m ever going to use it, and it seemed like you really enjoy it.” I said with a smirk.

“Hah. That I do.” He replied, and took another bite, as if this was any other normal conversation. As if that toy we’re talking about was just a yo-yo or something.

“Not that I can say I really understand what you get out of it, but if you want it it’s yours.” I said. I’m not really sure why I was pressing the issue. I knew he’d gladly take ownership of it, but a part of me wanted to make sense of why.

“Yeah. I’ll take it. Definitely. Thanks Dad.”

“No problem. Enjoy!”

“Oh I will!” He quipped.

I couldn’t help but chuckle at that. We both ate silently for a few moments, and I knew he could tell I wanted to know more, but didn’t want to pry.

“You want to know, don’t you? He asked

“Hmm?” I feigned innocence

“What I get out of it. You’re curious.”

“Ohh. Well… I mean yeah, kinda. But I’m not so sure that’s an appropriate conversation for you to have with your father.”

“Oh please. After everything I said earlier. And you saw my… you know. I hardly think it’s going to be too much at this point.”

“Hah. Yeah I guess you’ve got me there. Well… sure. If you want to share, I’m listening.”

He put his fork down and rested his elbows on the table. It seemed like he was thinking for a moment. I was just trying to play it cool. I kept eating while I waited for him to speak.

“So… I said before that I like all kinds right?” He asked. I nodded. “Basically what I meant by that is that I’m attracted to women, men, whatever, it doesn’t matter much to me, because the thing is it’s not really the whole person that I’m attracted to.” He probably saw the confusion on my face, so he continued. “It’s more just certain parts that I’m interested in. I mean, okay, you know Sarah right?” I nodded. “And you’ve seen her in a bikini. Even you can’t deny that her body is incredible. Well I’ve seen her with her top off and trust me those… Breasts… simply perfect.” I wasn’t loving the fact that my son was talking about a teenaged girls tits and expecting me not to think about them. Or maybe he was, who knows. But he kept talking so I kept listening. “Well, my buddy Cody has this incredible 9 inch… penis… that is also simply perfect.”

I could tell he was trying not to use vulgar words at the dinner table, which I actually appreciated.

When he put it in those terms it started making sense. But I was still hoping for more explanation so all I said was “Huh!”

“But they both attract me in very different ways. Like, with Cody, I have this crazy… hunger, for his… you know. But that’s kind of all I want from him. Just that one part. But with Sarah I love her softness, smoothness. Caressing her is like touching heaven. I just admire her shape and beauty so much. In a way I think it’s more like I’m envious of her. Which, I suppose ties into the whole women’s clothes thing. So, really I guess what I’m trying to say is; what I get out of the dildo is the desire part, and what I get out of the panties is the sexuality part. Does that make sense?”

By now I had sort of stopped eating and was just listening. It did actually make sense now. It’s no different from my own kinks really. I had always enjoyed a good raking from my wife’s nails on my back when she was close to climax. The dichotomy of the pain and the pleasure is something I’m into. Jason just has a similar but different kink.

“Yeah. It does. Totally.” I replied

“I hope so. I don’t really know how else to explain. But I suppose, if you needed to put a label on it, I’m what you would call… a sissy.” He said with some hesitation.

“A sissy?” I repeated back. What the fuck is a sissy? I mean I know what a sissy is to my generation, basically just a loser or a coward. That can’t be what he means here.

“Yeah. It’s just a term. It’s not what you’re probably thinking. It’s just something to define my sort of… sexual identity.” He explained.

“Hmm. Okay. Well I don’t think I’ve heard that before, but I’ll take your word for it.”

“Yeah, it took me a while but I’ve accepted it now. It caused me a bit of shame and whatever, when the guys started calling me that, but now I’m owning it, and it feels good.”

“And I think that’s awesome Jay.” I said before taking another bite. “I’m really glad that you told me all this. Makes me happy that you’re comfortable sharing with me.”

“Me too Dad.” He said with a smile.

Later that night, after Jason and I had finished dinner, watched some TV and shuffled off to our respective rooms, I immediately opened my laptop to learn all I could about what he had told me. I searched on the web to get more insight into his type of sexual preferences. I came across a lot of info from LGBTQ websites and the like, but the one thing I really wanted to find wasn’t popping up, that word, sissy. After some frustration trying to understand it through normal searches, it finally struck me; Porn. I would most certainly find the answer through porn.

So I went back to that site from earlier and this time I typed it in the search bar.

Boom. Hundreds of results. Scrolling down the page I read video titles.

‘Sissy trainer’

‘Sissy femboy gets fucked’

‘Feminization positivity trainer’

‘Sissy Princess stretched’

‘Femboy cum dump’

‘Caged fem sissygasm’

‘hypno cum training’

‘Daddy’s little cum whore – huge facial’

That last one caught my attention for obvious reasons, but I steered clear of it.

A lot of these terms I’ve never heard before, but the vast majority of the videos seemed to include the word training. So naturally it was one of those that I clicked on, titled ‘Sissy cum trainer’.

The video started and I turned the sound off immediately, just to ensure Jason didn’t hear anything. The screen was filled with quick cuts of large dicks in pussies, asses, mouths, one after the other, again and again. Suddenly some of them were cumming in their targets. Words started appearing on the screen. “YOU WANT HIS CUM”, it would say. “YOU WANT TO TASTE IT”. Flashing text intermingled and superimposed with the cocks cumming. I watched with some interest, wondering where this was going. Is this what Jason is into? Is this the kind of thing he likes to watch? As it continued, I noticed one of the quick cuts was a transvestite getting fucked. Soon after was another. And then another. Then there was a busty shemale cumming on her own tits. Still text was appearing on the screen as well encouraging the viewer to think about how delicious semen is. Eventually the video had transitioned into an endless barrage of trans cumshots. Some directly into the camera lens, but most onto their own body. Honestly it was kind of hot, and I found myself getting aroused yet again. But this time I resisted, and slammed the laptop shut.

Once again, I had to gather my thoughts and make sense of things. That video was some type of manipulation. It was almost hypnotic, like it was trying to make the viewer think in a certain way. The imagery was obviously specifically chosen to encourage a certain proclivity, but I noticed the transition it took. It’s not like it was subtle. I don’t think any of it was meant to be subtle. So if this is the kind of thing that my son is into watching, then he must WANT that… brainwashing. I couldn’t think of another word for it. That’s what it’s trying to do. But they call it “training”, and it’s not like you could make someone watch a video like that. So really, it’s up to the viewer to want to be trained.

As these thoughts were going through my head, I also noticed the fact that I, myself had been turned on a little by it. Not that it’s that surprising really. Like I said before, I do enjoy a good cumshot compilation from time to time. But by the time I closed my laptop, I definitely had a chubby going on, and those last images were all shemales. I wondered if that I meant anything about me. I was trying to understand Jason, but now my own sexual confusion was top of my mind. I decided I had to just shut it out and go to sleep. I can’t deal with this. It’s all too much for one day. I had to ignore my penis. Ignore my brain. Just go to fucking sleep. Tomorrow would be a new day.

For the next couple days I successfully managed to avoid both thinking about and talking about everything that had happened. Work was super busy because I had to make up for missing half an afternoon. Jason was mostly normal, and if anything he actually hung around more and seemed to be super relaxed. We chatted a few times and things actually felt pretty good.

A few nights later, after dinner, Jason came out to the living room and asked if I wanted to watch a movie with him. I said sure, and let him pick. We both sat down on opposite ends of the couch, with a space between us for snacks if we wanted later. It’s this time of night that I generally like to get comfortable in the warm house, and I usually take my shirt off to watch TV when it’s just us. So I did that and tossed it aside. I’m honestly not sure what the title of the movie was, but it started up with some action sequence and then had some nightclub scene and some mob boss thing happened. There were some topless ladies mixed in every now and then. You know, explosions, guns, car chases, naked chicks; your generic guy-flick. Then, about 20 minutes in, this sex scene starts between the two lead actors. The woman is busty and beautiful. The guy is tall and fit. They’re naked in the scene and suddenly to my surprise I see full frontal on the male actor.

“Huh! That’s unexpected.” I said. Jason didn’t acknowledge me, but I could see him turn towards me in my peripheral vision.

The scene continued, and the two on screen were now fully having sex. It wasn’t like it was porn, they weren’t showing penetration, but in some of the shots you could clearly see as the silhouettes moved on the bed their genitals were at least connecting. I was surprised. I didn’t think this kind of thing was in movies like this. As the minutes passed and the passionate love making went on I felt a stirring in my pants. It was definitely a hot scene, and I had no control over my bodily reaction. I squirmed in my seat a bit because my dick pressed against my pants, and also I was very aware of my son sitting just a couple feet away from me. Then I saw again in my peripheral vision, Jason’s hand was moving in his crotch area. Well shit, it seems like we didn’t have any secrets between us anymore, so I just decided to acknowledge it and turned my head to face him.

“So you… you like this?” I asked plainly.

“Hell yeah. Of course I do. You don’t?”

“Well sure. But I just thought you wouldn’t be interested really in-”

“In sex? What do you mean? Were you not here a couple days ago when we went through all that?”

“No, no. I mean. Nevermind.” I said sheepishly. I wasn’t really sure what to say. I was squirming again, and very uncomfortable.

“Dad, sex is a normal thing. There’s no need to be awkward. I thought we opened up about that.” He stopped touching himself.

“Yeah. No. I know.”

“Okay. Well you seem uncomfortable, so if you’re not enjoying the movie we’ll find something else.” Then he paused and looked directly at my crotch and said “Although, it looks to me like you are enjoying it.”

I looked down. Damn. I was fully hard now, and it was very obvious. Jason started rubbing his pants again slowly.

“You don’t want to turn it off, do you?” He asked.

I shook my head no as I stared at the screen again. The intensity was picking up and the characters were in the throws of ecstasy. My hand found its way to my crotch as well.

“Good.” Jason said as he untied the string of his track pants. “Cuz I can’t really help but…” he continued as he lifted the waistband over the tip of his dick and slid it down slowly, revealing his erection. I couldn’t help but look over and watch as he did it. His dick was long and hard, with completely smooth skin. He leaned back more in the couch and pulled the waistband all the way down past his balls and tucked it underneath them.

“Jay, what the f–”

“I’m sorry. I just… I have to.”

“No, you don’t!”

“Come on Dad. It’s okay. My friends and I used to do this all the time.” He quickly whipped off his shirt as well, and then started slowly stroking his cock.

“What? Like… together?”

“Yeah. It was a pretty normal thing for us. You know, before the whole isolation shit.”

“Okay, well, I’m not your friends. I’m your father. You need to put that away!” I said strongly.

“Oh come on. What’s the big deal? I know you jerk off. You told me as much.”

“Yeah. Of course I do. But not around other people. And certainly not my own son.”

“Why not? It’s perfectly normal. And totally freeing.” he argued. He hadn’t stopped stroking himself. His eyes were glued to the screen, and somehow my eyes were glued to his erection.

“Just… stop!” I begged.

“Nope. I’m not stopping.” He replied. “So you might as well start.”

“I’m not doing that.”

“Come on Dad. You know you want to. I can see it.” He said while turning to look again at my pants. “Seriously, it’s not a big deal. If you can’t do it with me here, then who?”

“No one! That’s the point! It’s called masturbation. Other people are not involved.”

“Well that’s not what my friends and I think. I enjoy the company while I do it.”

“It’s not right.”

“It’s not wrong. It feels good. Just… watch the movie. I don’t have to look if you don’t want me to.”

I turned my eyes back to the screen and the sex was intense. I was surprised how long it was going on for. I was really fighting it now. Jason was right, I absolutely wanted to pull out my dick and start beating it right there. It was a struggle in my mind. The man was now plowing the woman from behind in slow motion. Her big tits were swaying beneath her, and the camera focused on her nipples grazing the bed sheets. My cock twitched. Then a shot of the man’s hand gripping her thigh tightly as he slammed forward into her. It twitched again. Then a close-up of the woman’s face as she bit her lip and her long hair flowed with the motion of getting fucked. It twitched again. Then the scene cut to the woman on her back and the man between her legs missionary style. Still in slow-motion, her huge breasts shifting back and forth atop her chest like water balloons with every thrust. The camera focused close up again on her hard nipples, and that was it. That’s what did it.

The next thing I knew, my hand was moving on its own, unbuttoning my pants and pulling them open. With complete disregard for the fact that my son was sitting not two feet away from me, I yanked down my underwear and set my erection free.

“There ya go.” I heard him say. He had clearly lied and was indeed looking at me. Fortunately for him, I did not care in this moment.

I kept my eyes on the screen and proceeded to jack off to the sex scene. I had a tight grip on my cock, and began to stroke faster and faster. I had to hold my pants down with my other hand, but I held them as far away as I could so I could feel my balls move with every stroke. I got the feeling Jason was watching me intently now. I saw his hand start moving faster. I didn’t care. I wanted to cum to this beautiful busty woman on my TV before she was finished getting fucked. I beat my meat with more urgency as they switched positions one last time so that she was on top of him. Fuck yes, I love that. Her huge heavy tits hanging in the man’s face now. I imagined it was my face. He grabbed them both with his big hands. I imagined they were my hands. He took her nipples in his mouth one at a time. I imagined it was my mouth. Then as the camera showed a side view of her ass slamming down to meet his thigh and she screamed in ecstasy during her climax, the man grunted simultaneously, and I too shot my load all over my chest. While the woman collapsed on the man and they gently kissed in the aftermath of their lovemaking, I kept stroking my dick slowly, enjoying the scene.

“Whoa.” I heard my son mutter from beside me. That’s when I remembered he was there. I had completely covered myself in semen. I’ve always ejaculated a good volume, but this was a lot even by my standards.

After I surveyed my mess, I glanced over to my son. He now had one hand firmly wrapped around the head of his long cock, and the other wrapped around his balls, sort of stretching them outwards. Both hands were just twisting slightly and then suddenly, without warning, a burst of cum flew from the tip and landed on his neck. It actually startled me. Then another shot onto his smooth chest. And another, and another. He released his balls and they sucked themselves back towards his dick while it pulsed a few more times emptying semen onto his stomach. He hadn’t made a sound through his orgasm, just some heavier breathing. He dropped his towering dick from his hand and it landed on his stomach with a wet ‘thwack’.

We both sat in silence for a few moments, with just the sound of the movie in the background. Looking at each other, then the screen, then back to each other. It hit me that we were very different in some ways, but so similar in others. Physically, we were polar opposites. I’m a fairly tall, barrel-chested, hairy man with big tree trunk legs. I usually have a crew cut, but have just been shaving my head completely lately and growing my beard instead. My penis is average length but very thick. My son, on the other hand, is a few inches shorter than I am. He’s a thin, smooth-skinned boy with no hair to speak of except on his head. He’d decided to just let it grow since hairdressers closed during the pandemic. He must shave his pubes because even his crotch is completely bare. His penis stands tall and straight but is not thick like mine. I never really understood the big difference between us. All the men in my family have always been big and hairy. He definitely got all of his looks from my wife’s small family. Yet we seem to have similar libidos, as well as the inability to control them. And it looks like we both ejaculate a lot of semen, so there’s that.

The awkwardness definitely set in quickly for me though. In fact I think it was more than just awkwardness, it was more like regret, and shame. What had I just done? I can’t believe I had masturbated in front of my son. No, I had masturbated WITH my son. He was wrong, this was wrong. We shouldn’t have done it. I shouldn’t have done it. Then Jason spoke.

“Nice one… Dad.”

He was looking at my spent cock, and my cum-soaked chest and stomach. What the fuck? Was he talking about my ejaculation? Did my son just compliment my cumshot? I couldn’t react. I didn’t know how.

I sat up, trying not to spill my semen as I did. Not really too much of a problem since it was all matted in my chest hair.

“I’m going to uhh, go clean up.” I said, standing.

“Yeah. Okay.” Jason replied, while he grabbed the remote and paused the film.

I tried not to look at him again while I walked towards the bathroom, but out of the corner of my eye I saw him lying back again instead of getting up to clean as well. Just before I rounded the corner, I noticed him wiping his body but instead of using a tissue or anything, it was just his hand, which he then brought to his mouth and licked clean. Wow. This just keeps getting stranger.

I cleaned up in the bathroom with some tissues. It took quite a few. I didn’t really get it all because it was caught in my hair. As I scrubbed at it frustratedly, I looked in the mirror, and saw the shame in my own eyes. How could I do this? That was so wrong. I can’t believe what I’ve done. But more importantly, what the fuck do I do now? I can’t go back out there. How can I face him? If his post-nut clarity is as clear as mine he’s got to be on his way to his room by now. I hope so. But then again I don’t want him to feel ashamed about anything he does in this house. Fuck. What do I say to him now? What could I possibly say?

I took a few more minutes and came to the conclusion that I had to just bear it and go back out there and sit down. If he acts normal, then I can too. And if he doesn’t then we’ll just have to have a frank conversation. I’m the adult here. I can do this.

When I got back to the couch, Jason was still there, and he had his shirt back on and pants pulled up. He was just waiting for me patiently, not even on his phone or anything. Before I sat down I decided to cover myself as well, so I grabbed my shirt and pulled it on. Before I could say anything or even sit down Jason spoke up first.

“Popcorn?” He asked.

Well, I guess we’re going the not talking about it route.

“Uhh, sure. If you want.” I replied, and headed over to the kitchen. I microwaved a bag of popcorn, dumped it in a bowl, and brought it back to the couch with me. By now Jason was on his phone, but put it down when I placed the bowl between us.

“Awesome, thanks!”

“No prob” I said, picking up the remote and starting the movie again.

The rest of the movie went by but I really wasn’t paying much attention. A bunch more stuff blew up, a lot of guns were fired, some new tits were shown, but ultimately I have no idea what happened in it. When the credits rolled Jason stood up quickly and grabbed the empty popcorn bowl. As he took it over to the kitchen sink he said “Enh. That was alright.”

“Yeah.” I agreed. “I guess.”

“Best part about it was that sex scene.” He said casually, as he walked back past me heading to his room.

I didn’t know what to say to that, so I just scoffed.

“Oh well. They can’t all be winners.” He concluded. “G’night Dad. See ya tomorrow.”

“Yeah. ‘Night.” I replied.

I was baffled. To him, it’s like nothing had happened. Is this just how he was handling the awkwardness? Or did he honestly not care about what we’d done? Or did he just feel that it was a normal thing? Oh no. What if he thinks it’s a normal thing? What if he thinks it’s something we can do together now? Like he used to with his friends. Good lord, what have I done?

The next morning Jason came out for breakfast wearing nothing but his underwear. Not his Mother’s underwear, mind you, his own underwear, which were jockey style. They weren’t briefs but they were still plenty tight enough to see the shape of everything inside them. I think it’s just what he sleeps in, so he’d decided not to put on anything extra. It’s not like he has never walked around like this before, but it’s definitely not the norm, and with what happened the previous night I found it very suspicious.

“Mornin'” he said chipperly.

“Hey, how’d you sleep?”

“Ohh, like a baby.” He answered, also suspiciously.

“Good.” I said, ignoring the obvious bait to ask him why. “Ya want some eggs? Or just cereal today?”

“Uhm… Maybe just toast actually. Need to watch my waistline, ya know?” He answered with a smirk, and a pat on his bare hips. “And coffee?”

“Sure. I’ve gone through two cups, but I’ll put the pot back on. But really, you could stand to gain a few pounds I think.”

“Thanks.” He said, ignoring my comment, and started preparing his toast.

I knew something had to be said, and if I left it too long it would just become harder and harder to bring up. So I had to just get it over with.

“So, Jay, listen.” I started. “About what happened last night. What we… both did.”

He jumped in before I could say any more.

“Oh! Yeah. I was thinking…” He said somewhat excitedly. “Next time, I have the perfect film for that. I actually think you’ll really like it. It’s not like a porn or whatever but it’s got a lot more great scenes like that one, and I think you’ll actually dig the story. I watched it a couple years ago with the guys.”

Oh my god. It’s exactly what I had feared. He was under the impression that it was now something we could do together. I had opened a door, which I now had to close. I spoke up quickly.

“No. No no no. What? No. Jay, I was going to say… what happened last night… it can’t happen again.”

“What? Why?”

“Because it shouldn’t have happened in the first place!” I argued.

“Why not? You enjoyed it didn’t you? I mean, you very clearly enjoyed it. I saw the evidence.”

“No. I mean, yes but–”

“Okay, so what’s the problem?”

“The problem is you’re my son, and I’m your father. And we shouldn’t even be exposing ourselves each other, let alone gratifying ourselves in each other’s presence.”

“I really don’t see why not. After everything we talked about, and that day you saw me doing that… with the… toy. I don’t see why we should have anything to hide.”

“It’s not about hiding. It’s about common decency. Some things should remain private. Even from family. A father should not be… masturbating in front of his son.”

“Well, I don’t plan on keeping private for long. I’ll be eighteen in a week, so…”

“So, what? What does that mean?” I asked, genuinely curious. I wasn’t sure if he was just talking about masturbating in the house or something more.

“Nothing. Just… it doesn’t matter.” He stuttered.

“No, what does it mean? You’re going to start jerking off everywhere now?” I was getting frustrated.

“No, just forget I said anything.”

“No, really Jay. We’re not going to have privacy anymore? Is that it? So you’re just going to start cumming all over the house? First your bedroom, then my bedroom, then the couch… with me on it at the time. What’s next? You gonna whip it out here at the breakfast table?”

He laughed out loud. “Damn Dad, calm down. That’s not what I meant.”

I realized I had raised my voice and took a breath. “Okay. Well, all I’m saying is sometimes I appreciate MY privacy. So, while it’s great that we’ve opened up a bit recently, I just think we should have boundaries. And NOT masturbating in the same room at the same time is one of them.” I said, trying not to use the term ‘together’ in the sentence.

“Okay. Fine. I guess.” He reluctantly agreed.

“Thank you.” I said. “Here. The coffee’s ready.”

I placed the pot on the counter in front of him and he picked it up to pour into his mug.

“I still don’t know what the big deal is. It’s just a bit of fun.” He muttered under his breath.

I just shook my head and took a sip of my own coffee, then went into my den for work.

The day went by fairly normally. That conversation at breakfast was all that was said of the incident, so I figured it was done and dusted. Matter closed. We even got through dinner without mentioning it.

But after dinner Jason proposed we do something together. I liked that he was willing to hang out with me more now, so I asked him what he wanted to do.

“You want to play cards or something? A game maybe?” I asked.

“Sure. Probably beats sitting in front of the TV.”

“Alright, which is it? You decide.”

“Okay. Hmm…” He thought for a moment. Or faked thinking, I couldn’t quite tell. “Oh! How about my favourite game of all time. Truth or dare.”

“What? Jay, that’s not a game you play with your parent. That’s a game you play with your friends when you want to pull some pranks and shit.”

“Well my friends aren’t here. And I haven’t been able to see them in over a year.”

“I know.” I sighed. He was trying to guilt trip me. “But come on. You know it’s not the same game if you play it with your father.”

“Sure it is. There’s plenty of things I bet I don’t know about you.”

He had me there. And on the flip side there were plenty of things I could find out about my son if he answered some questions honestly. I thought about it for a moment.

“That’s probably true, but perhaps it should stay that way.” I replied.

“Okay well, you told me to pick but if you don’t like it then you pick something.” Again with the guilt tripping.

I thought for another moment. This really could be a chance to find out more about this new aspect of my son’s life.

“No. Okay. You’re right. I told you to pick. So… fine. We’ll play. Let’s go sit in the living room. I think I’ll need another beer for this.”

We got up from the dinner table and Jason went over to the couch. I stopped by the fridge to grab myself a beer and popped the cap as I walked to the couch as well. We sat down in the same spots as the night before, but he sat facing me this time, with one leg up on the seat.

“Alright. How do we start?” I asked.

“Uhm okay. Well… I’ll let you go first.” He said excitedly.

“Okay. So I just ask… Truth or dare?”

“Yep. I’ll say… Truth.”

“Truth. Okay… Ummm… Oh. I got one. What do you like most about online school?” I asked and then took a sip of my beer.

“Easy. Waking up five minutes before class starts.” He answered. We both laughed. “Truth or dare?” He asked me.

“Truth.”

“When was the last time you came as much as you did last night?”

I hung my head and sighed. I knew it. I knew that’s what this little game was about. The very first question he couldn’t help himself but bring it up.

“Jay. Come on. If this is what this is going to be then I’m not going to play.”

“This is the game Dad. This is how it goes. Dirty little secrets and shit.”

“Which is why I said it’s not a game you play with your parent.”

“But then you agreed. So we’re playing now. So, what? You’re going to back out? That’s not cool.”

I sighed again. And took another sip of my beer.

“Fine. It was probably a few months ago.” I answered reluctantly. He gave me a look that suggested he wanted more details. “I was kind of pent up from some stuff I’d seen, and hadn’t… you know… done it in a while. So when I finally did, it was… very satisfying.” I explained.

“Makes sense.” He nodded.

“Okay my turn. Truth or dare?”

“Truth.” He said. “And remember… secrets and shit.”

He was encouraging me to ask him something sexual, I’m sure. Like what’s his fantasy and that sort of thing. I definitely wanted to know more about this new him I’d learned about but didn’t want to fall into his trap.

“Okay, how about this.” I said. “How often do you wear your Mom’s panties?”

“Now we’re playing.” He said as a smile crept onto his face. “I probably do it a few times a week. Definitely not every day or anything. Only when the mood strikes me. Truth or dare?”

“Truth.”

“Did you buy Mom that dildo because it’s the same size and shape as… you?”

I was surprised, but not, at the same time. I suppose he’d examined my erection enough while watching me masturbate that he figured out the dildo was my clone, or close to it at least.

“Hah! You noticed that, I guess. Well, actually, truth is… it’s an exact replica of my penis, yes. I bought one of those cloning kits for her one year and we made it together. I just wanted her to have the option if I was ever away or something. It’s actually quite remarkable how identical it is.”

“No way! Holy shit.”

“Yep. No joke. It’s me.” I confirmed. “I should have told you earlier, I just didn’t want to freak you out, cuz you’d already used it. Honestly I just didn’t think it’d ever come up.”

“That’s…”

“Yeah, I bet it makes you feel weird about having it now. Sorry son.”

“No. Not at all.” He said quickly. I looked at him, puzzled. “I mean, it’s just, that’s funny is all. But it doesn’t weird me out. If anything I kind of appreciate it more. It’s like… personalized.” He laughed.

This was certainly an odd reaction I thought. But then again this was the kid who is trying to convince me it’s okay for family to jerk off together, so who knows what he’s thinking. I drank some more.

“Anyway. Your turn.” He said.

“Truth or dare?” I asked.

“Truth.”

“Alright. Hmm. Have you used the dildo since I told you could have it? I noticed it’s not in the night table anymore.”

“Of course! Several times. Pretty much every day actually. Sort of my new go-to technique now.” He answered with another smile. “Truth or dare?”

“Truth.” I said yet again.

“Okay. How about something from my world. Have you ever had thoughts about another man?”

This one actually caught me off guard more than the others. I didn’t really know the answer. I mean I know I’m not sexually attracted to men, or even just their parts as Jason had explained he was, earlier. But had I EVER thought about a man before? Maybe. I’m really not sure.

“Wow. Uhhm. Honestly I don’t think so.” I said while I thought about it some more and took another swig of beer. “I mean, I know some attractive men, but I wouldn’t say I actually thought of them in any way that would suggest I am attracted to them. If that makes sense?”

“Okay. Fair enough.”

“Alright, truth or dare?”

“Truth.”

“Is it just panties you like to wear, or do you wear other stuff of your Mom’s as well?”

“See, I knew you had questions.” He said before thinking for a second. “There’s a few other things. The pantyhose, though I would prefer knee-high socks but I don’t think she had any of those. A few of the crop tops fit me okay. I mean, in the way they’re supposed to fit me anyway. That’s it really.”

I took a few more sips while he answered. This was getting to be a bit much, and I was definitely feeling the beer now. He didn’t even let me process the answer before he kept the game going.

“Truth or dare?” He asked me.

“Oh geez. Let’s do dare, this time.” I said, thinking the truth bombs we’re getting out of hand.

“I dare you to take off your pants and underwear for the rest of this game.”

“Okay. Nope. That’s enough of this. I’m out.” I said, standing up.

“What? Dad! You can’t just–”

“Yep. I can. We’re done.”

“That’s the game Dad! You try to make people uncomfortable.”

“That may work for your buds, but I’m not your bud, I’m your father. I’m not just gonna rock out with my cock out while we play a stupid game.”

“It’s not stupid. We’re learning about each other.”

“Oh really? What would me sitting here with no pants on teach you about me?”

“It would teach me that you’re not embarrassed by anything.”

“Suuuure.” I said, noticably slurring my words now.

“It would teach me that you have the confidence to be vulnerable around your son.”

“Uh huh.” I mumbled.

“It would teach me that you don’t back down from a dare.” He said, staring daggers at me.

I stared right back and gritted me teeth.

“Damn right I don’t!” I said as I put my almost empty beer bottle down. Then I grabbed the button on my pants and ripped it open, quickly unzipped the fly and yanked both my pants and underwear down in one swift motion. I collapsed back down onto the couch, with my pants around my ankles still. I picked up my beer and up-ended it to finish it off. I looked over at my son who’s eyebrows were raised up high. “There. Happy?”

“Yep.” He chuckled.

“Great. Now truth or dare dammit!”

“Well, I guess we’re going with dare now.”

“Okay. I dare you to go put on all your favourite things of your mother’s, and sit here in them for the rest of this game.”

He seemed a bit surprised at the request, but if he was going to try to humiliate me, then screw it, I was going to make him show me his feminine side, in full. He didn’t actually say anything but had a look on his face as if to say “Okay, you got it”. He immediately got up from the couch and went down the hall towards my bedroom. I figured he’d be a few minutes so in the mean time I got up as well to grab another beer. When I almost tripped over my pants, I kicked them off completely in frustration. My dick danced around limp as I did it and I thought to myself “This is ridiculous. What am I doing?” I half ignored myself and made it to the fridge, grabbed another beer and went immediately back to crash down on the couch. I sort of took up more than half of it with the sloppy, mostly laying down position I was in, but I didn’t care.

Minutes later Jason came around the corner. My jaw practically dropped. He was wearing my wife’s pink lace panties, with black pantyhose that were held up with garter belt suspenders. A pink and black striped crop top that showed his belly button rode higher when he raised his arms to present himself to me. He did a spin and I watched in both amazement and shock. He had even put his hair up into pigtails.

There was nothing else. Just 4 items of clothing that left nothing to the imagination. His slim teenaged body actually fit very well in it all. Everything but his poor squished penis. I could see the bulge through the lace, and thought it must be uncomfortable. It was also the first time I’d seen his ass mostly bare. The panties were quite tiny, and his tight butt wasn’t covered by them at all.

“Oh my.” Were the only words I could muster.

“You asked for it. Dad. This is me.”

“I… I don’t even know…”

“This is sort of my favourite outfit that I’ve put together so far.”

“Well it’s… it’s something.” I had no idea what to say.

He smiled at me again and came back to sit down, trying to find space now that I was sprawled out more.

“Well. So is that.” He said, pointing to my crotch. I hadn’t noticed but my dick was growing. Not exactly getting hard, but definitely thickening and moving on its own. Jason cleared his throat. “Truth or dare?”

I was distracted by how he was sitting now. He had sat with both legs together, sort of on his side with his feet tucked up behind him on the seat. My brain couldn’t comprehend where his genitals had gone. They must be crushed somewhere in there. That couldn’t possibly be comfortable. But with his slim figure and smooth legs covered in pantyhose if I was looking away from his face he really truly looked like a flat-chested woman. It was remarkable. I could tell I was really feeling the beer now because he had to clear his throat again before I responded.

“Uhm. Truth.” I said, figuring it would be safer at this point.

“Okay. How long has it been since someone else has given you an orgasm?”

“Jay. That’s not–”

“Because I know we haven’t been anywhere or had anyone over in forever.”

“Well. Yeah, exactly. It was your mom. Obviously. So really you’re just asking how long before she passed did we last have sex?”

“I guess. When you put it that way… I… you don’t have to answer, I’m sorry Dad.”

“Nahh nah it’s okay. The game is the game.” I said brushing off his apologies. “Umm let me think. I think it was probably about 2 weeks before she got sick. So I don’t know, you do the math.”

“Oh man. Dad, that’s… so long. That must be so frustrating for you. I’m so sorry.” Jason said, as he placed his hand on my thigh.

“Yeah. Well it is what it is.” I replied, shrugging my shoulders. “And I’m sure it’ll be probably another two years before I can even try to meet someone to take care of that. If I ever even want to.”

“You’ve got to Dad. Every man needs it. It’s just human nature. Nothing to be ashamed of.”

“It’s not about that. But whatever. Truth or dare?”

“Truth.”

“Alright. Here’s what I really want to know.” I said, putting up both my hands, almost dropping the beer in the process. “When did this all start for you?” I asked, gesturing to his new attire.

“Ha. Funny you should ask actually, because it started like this. With a game of truth or dare.” He answered.

“Oh really?”

“Yep, hence why it’s my favourite game. You want the short version or the long version?”

“Whichever one will make the most sense in the end.”

“Okay. Long it is.” He said as he sat up a bit higher and prepared to tell the story. “So on New Years Eve, before the pandemic, I went to Joanie’s party remember? You and mom went to aunt Carol’s.”

“Right.” I nodded

“Well, a bunch of us were staying over and eventually we decided to play this game. Everyone was choosing dare, so it only took like twenty minutes for the whole circle to be half naked. Every girl had their top off, and Cody was sitting there with his glorious dick out, because it’s the one everyone wants to see. Then Joanie gives the big dare to Kate. Tells her to suck Cody’s dick in front of everyone. I think maybe she just wanted to see Cody hard because she’d heard all the stories and never seen it for herself, but she didn’t want to do the blowjob so she was just waiting for her opportunity. Kate LOVES sucking dick. And everyone knows it. She’s not at all shy about telling people. She brags all the time that she’s the best. Well, she WAS the best, until I came along.” He paused briefly and glanced up at me to see if I reacted. I didn’t really. The story was already a little crazy to me. This is what my son does with his friends? Sits around naked basically having orgies? Anyway, I shrugged it off and kept listening. “So Kate goes ahead and blows Cody in the middle of the circle. He’s lying down on his back and she’s basically in a downward dog over him, so everyone is also getting a nice view of her ass while she does it. Anyway, the reason this is relevant is because as Kate was doing her thing, her panties started to soak through. She was getting so horny from the dick in her mouth that her pussy was literally dripping. Everyone saw it and the other girls started freaking out. Like, in a good way. Like they were so excited that she could be so excited by giving head. Like it was blowing their mind that she actually liked doing it THAT much. So anyway, as this was all going on, the game was still happening. And someone dared Joanie to make out with Kate after she was done with Cody. Well Joanie didn’t really put two and two together, but as soon as Cody blew his load in Kate’s mouth, Kate gets up and grabs Joanie to kiss her. The look on her face was fuckin priceless. Cum spilling out of their mouths and shit. It was great. Anyway, that part’s not relevant, just a super fun story. So, after everyone is done watching the show and we’re all sitting there, all the guys are rock hard, except for me. To be honest, I’m really not sure why I wasn’t. I mean I’d basically just seen a live porn show and for whatever reason I was just sitting there like normal. Well, except for the dribble of precum in my underwear. I had realized at some point while it was going on that I actually wasn’t jealous of Cody, but rather Kate. She looked so good in just her panties, with her perky tits hanging down, hair up in a ponytail, just slurping on a beautiful cock like it was a popsicle. But it was just how much she was enjoying it that got me. Like I’ve never seen a girl in such heaven before, with an audience to boot. But anyway, Steve called me out for my limp dick, which was clear, given how all the other guys were stretching their underwear, or already had their hard dicks out. So everyone looks at me. Cody says ‘Truth or dare Jay’. I froze. The last thing I wanted them to know was what I was thinking about that whole time watching the blowjob. And I knew if I said truth I’d have to answer something about it. So I chose dare.” He looked down bashfully and ran his hands along his pantyhose-covered legs. “Cody dared me to take off my underwear… so I’d be naked at that point… and put on Kate’s wet panties.”

“Ohhh shit.” I whispered.

“Yeah. Exactly. But I had to do it. So I stood up in front of everyone, dropped my shorts. Kate stood up, dropped hers, and lifted her foot to hand them to me. They were tiny. Like, not quite a g-string, but very small all the way around. I bent over and stepped into them, slid them up slowly. I figured I’d make a bit of a show of it, just to prove I wasn’t embarrassed or scared, but really my heart was pounding. When I got them all the way up, I tried to keep my dick in them but they were too small to hold it. So I was just like fuck it, and let it slip out. But the real thing was, as soon as that warm wet spot touched my balls, that was sort of the moment. It hit me how good it felt. Cody asked me how it felt and all I could say was that it felt good. Everyone blew up laughing. They were all like ‘Oh my god he likes it!’, and ‘He looks like a sissy boy’ and that shit. It was just so different and soft. It made me feel… sexy. So I sat back down in my spot and just wore it. I was like stroking the fabric and like rubbing myself. Anyway, the game went on. Every now and then someone would glance at me and I just couldn’t do anything but smile back. At some point Steve couldn’t help himself and says ‘I want to dare the sissy to do something’. The rest of the guys started teasing me calling me a faggot and a femboy and all that. At first it got to me, but the more they said it the more stubborn I got, and just kept the panties on out of spite. Eventually I got fed up and said ‘Fine. Steve, you want to dare me to do something. Then go ahead. I chose dare’. So Steve says ‘Okay ya fuckin sissy fag, crawl over here and suck my dick’. Just like that.” He stopped his story, and looked at me waiting for a response.

“So… what’d you do?” I asked with my eyebrows raised.

“I sucked my first dick.” He answered plainly. “And everyone watched… the entire thing. No one stopped it. No one left. No one even really said anything or looked away. I just did it right there like Kate had. And just like Kate, I loved every second of it. In fact, if anything, I wished Steve had lasted longer, but I made him cum in like two minutes. Swallowed it down like it was water. I was instantly hooked.”

“Wow. So, that’s how it started eh?” I said.

“Yep. And the game went on for quite a while, but that’s probably a long enough answer for now.”

“Well, that’s one hell of a story.”

“Yeah, it was good times. Hah. Kate and I actually had a bit of a competition later on because Steve was ranting about my… skills. But she wanted to prove herself to me as well and ended up getting her panties back only after she ripped them off me and gave me head in exchange.”

“Geez.” I said lamely. “Sounds like you and your friends have some… wild times.”

“Hmm. Yeah. I guess.” He agreed. “But I realized that night just how good they all are. Like no one really judged me for what I did. If anything they accepted it and kind of encouraged it like right away. I mean, I think originally Steve was just saying it to make fun, expecting I would back out. But when I crawled over to him and yanked down his boxers he was surprised sure, but he didn’t stop me. Everyone was stunned but I think they could all see I actually wanted to try it. So they made me feel safe about it. And when it was done Steve basically was like ‘holy shit that was awesome’ and told all the other guys they had to try me out. Which… they all did… I think. I don’t remember. But now they still call me those things, but it’s more in an endearing way. Like it’s an inside joke almost. Yeah, I love my friends. They’re the best.” He explained, getting lost in his thoughts.

“Call you what things?”

“Like, sissy, femboy, faggot. That kind of stuff. They say it all the time now, but only because they know they can. I like it when it comes from them. In fact, it’s sort of a trigger. Let’s me know when they’re down for some action, and really gets me in the mood, if I’m being totally honest.” He seemed a bit bashful with that last statement. “So anyway, your turn Dad. Truth or Dare?” He said, lightly slapping my thigh.

“Oh geez. Uhm.” I couldn’t think properly after that crazy story, and I was definitely feeling the booze. I was scared if I said truth I wouldn’t even be able to answer a question properly. So, stupidly, I said “Dare.”

A sneaky grin came to his face immediately and he said “I dare you to let me rub that out for you.” while eyeing my crotch.

I looked down and realized my dick was rock solid. Jason’s story about his horny teenaged friends must have seriously aroused me, and I hadn’t even noticed. In fact there was some precum glistening at the tip of my swollen head.

“Oh, fuck!” I screeched, trying to cover my erection with my hands. “No! What?”

“Yep. A dare’s a dare. You can’t back down.”

“That’s not a dare! That’s just wrong!”

“Nope. It’ll be fine, you’ll see. Come on, you have to now.”

“No I don’t. That’s insane!”

“Dad. Come on, you don’t even have to do anything. And it’ll feel so good.”

“I don’t care. That’s too far. WAY too far.”

“Oh please. Why? Because we’re family? It’s not sex!”

“It basically is.”

“No it’s not. And you said yourself, it’s been forever since you’ve had someone else do it for you.”

“I don’t care.”

“Dad. I just want to help you. I want to make you feel good. I’m practically a pro at this point. You realize that right?”

“I don’t care.” I repeated, shaking my head.

“It’ll feel sooooo good. You just have to lay back and close your eyes. Just imagine it’s someone else. Hell, imagine I’m Mom. Imagine it’s her hands.”

“Oh my god that’s even worse.”

“No it’s not. I’m the only one who knows you like she did.”

“That doesn–”

“Let me do this for you. I promise it’ll be amazing.”

“I can’t–”

“Yes you can. Just relax, and lay back.” He started rubbing my thigh now, and pushing on my chest with his other hand.

“This isn’t righ–”

“Thaaaat’s it. Close your eyes, and just… enjoy.” He said quietly and slowly. I did as he asked.

“Oh my god, this is craz–”

“There ya go. Good.”

Just then I felt a palm of a hand run up the length of solid dick. When it reached the top it wrapped around the head softly. I heard him moan in delight, and I think I did the same. I felt his other hand wrap firmly around the base of my dick and lift it off my stomach. He gave it a good hard squeeze with both hands.

“Ohhh man. It really is the same.” He whispered. I understood he was talking about the dildo that was now his. “Holy fuck.”

He stroked it a few times with that firm grip. It felt amazing. It had been so long since my cock was pleasured by something other than my own hands. I’d almost forgotten the feeling entirely. One of his hands left me, and a second later I heard a squirting sound. Soon the hand returned directly on the head of my dick. A brief shock of cold hit me and I squirmed slightly. Then he started swirling that hand around my head. It was gliding smoothly now. I see, it was hand lotion from his side table over there. I didn’t care what it was, I practically melted at the feeling. I moaned out loud and relaxed deeply into the couch. His gliding hand was like magic on the head of my dick. He had worked the other hand into it now and both were sliding on my shaft easily and softly now.

“Mmmm. How does that feel Daddy?”

“Oh my god, so good.” I said in panted breaths.

“I loooove this cock soooo much.” He said in a low voice. “This is the best, most beautiful cock I’ve ever seen.”

I couldn’t respond. His hands were working on me now in a way I’d never felt before. His strokes were long, slow and deliberate. We was feeling every inch of my dick, and I could feel his hands in detail, as if his fingerprints were ribs for my pleasure. He grabbed my balls and pulled them, while using the other hands on my head. I squirmed again. I hadn’t felt anything like this either, and it was incredible. His hands started twisting and my body jolted. I instinctively reached my hand out to his leg. I felt the smooth pantyhose, and ran my hands upwards and felt smooth skin. I couldn’t take it much longer. As I started panting he began to encourage me.

“Ohhh yeah. Come on. That’s it Daddy. Let it go. Give it to me.” He whispered while stroking now, faster.

That was all it took. I arched my back and let out a great big moan while I blasted a shot of cum that went over my head. His hands slowed again and gripped the entirety of my shaft at once. With slow twisting strokes, he coaxed the rest of the cum out of me.

“Mmmmm yeeeeeah. Come for me Daddy. Come nice and hard.”

Shot after shot of my load erupted out of my swollen cock, painting my shirt.

“Thaaaaat’s it.” He kept saying while he finished emptying my balls with slow firm strokes. With a final sigh, I knew my orgasm was passed. I opened my eyes and looked down at myself. He kept holding my dick with both hands, feeling it pulse even after it was entirely spent. Then he kneaded it from base to tip, milking out every drop of cum that he could. I looked at him sheepishly, and he had nothing but wonder and bliss on his face. “That must have felt sooooo good Daddy.” He said.

“Ahh, yeah. It did.” I admitted. I let my head fall back on the couch pillow while I reveled in the feeling of that orgasm. Just like his buddy in his story, Jason had made me cum in a matter of minutes, and it was one of the best orgasms of my life. Wait, did he call me Daddy? He hadn’t called me that since he was a boy. I shook off the thought.

My son finally released my spent dick and gave it one last loving caress as he did. Then out of the corner of my eye, I saw him bring his hand to his face. I lifted my head to see just as he licked a long drip of my semen off the back of his hand.

“Jay!” I yelped.

“What? I had to see what it tastes like.” He said, with a wicked grin. “It’s divine.”

“Oh my god.” I said to myself. What have I done now? I sat there, well laid there really, stunned, not knowing what to do or say. My mind was swimming and the room began to spin a bit from the beer.

I looked down at myself and the mess I’d made and noticed Jason’s legs spreading open. His erection was already sticking up out of his panties, and he pulled them to the side to release it fully. His tight ballsack popped out of them as well as he leaned back a bit to get comfortable. Then he looked me right in the eyes as he began to work on his own member. I felt my mouth drop open as he started. I hadn’t noticed until now but did he put on some lip gloss as well? My eyes drifted down to see his creamy hands gliding up and down his long shaft now. The mixture of lotion and my cum were coating it in a white sheen. For some reason I couldn’t look away. I was mesmerized.

He worked it with both hands, slowly but firmly, just as he did with mine. I couldn’t believe what I was seeing. He was close enough to touch, but I didn’t. Our legs were touching actually, which made it all the more… confusing. I liked the feel of the pantyhose against me, but I was frozen, I knew I couldn’t touch him. I didn’t want to. Did I? It didn’t matter though because he seemed perfectly happy touching himself. He was moving through the same exact techniques he used on my dick not a minute earlier, and just as I had finished, so did he. He had one hand twisting on the head of his long cock and the other squeezing and rolling his balls when the first shot erupted. His mouth opened wide and I noticed his eyes lock on my cock. He stopped everything except some tiny little pumps on his dickhead and he breathed sharply as another jet shot up onto his face, some landing on his tongue. Then he just moaned continuously as he launched spurt after spurt cum onto his mother’s shirt. I watched in amazement as his balls contracted and his shaft pulsed with each surge of his orgasm. As it subsided and the last dribbles of semen dripped over his knuckle I looked at his face again. He was licking his lips but still focused on my cock. I followed his eyes and saw that my dick was almost hard again. What the fuck? I literally came just two minutes ago, how was I possibly getting hard already? But more importantly than how was why? I had just watched my son masturbate… again. Why the fuck would that make me hard? I couldn’t take anymore, I had to leave.

“I think that’s game over.” I said commandingly as I tried to sit up. With my feet planted on the floor I rested my elbows on my knees and put my head in my hands. The room was spinning. I looked down and all I could see was my dick, sticking straight out, semi-hard.

“Whoa! Take it easy.” Jason said, reaching out for me.

“Uhhg. I think I’m–”

“Yeah, just sit back. Here you go.” He coaxed me back to a laying position. He stood up off the couch and let me take it all. He helped me put my feet up and then kneeled beside me. “Dad, just… lay down. It’s okay.” He whispered.

“Sorry son, I–”

“Don’t be sorry. This was… this was a lot of fun.” He said. “Just… get some sleep.”

The last thing I remember was watching cum drip down his crop top, while his hands wiped my crotch. Then… darkness.

I was awoken by Jason shaking my shoulder lightly. I squinted and rubbed me eyes because the sun was pouring into the living room.

“Hey. Mornin.” He said quietly. “How ya feelin?”

I looked him over. He was wearing just his underwear again. My immediate thought was that I hoped that wasn’t going to become a regularity, but as the morning sun bathed his milky smooth skin, I began to warm to the idea. I looked at my own situation. I could feel that I was still not wearing bottoms, but at least I was covered with a blanket. That was nice of him. The issue was that I really really needed to relieve myself.

“Uhg. I feel okay.” I answered. “Just uhh… got to hit the head. Badly.”

“Ha. Of course.” He said. “Coffee?”

“Please.” I replied, as I stood up, wrapping the blanket around me. I quickly grabbed my pants from the floor and practically ran to the bathroom. As I relieved myself, I stared down at my penis and noticed how nicely moisturized it felt. Yet there wasn’t any excess of the lotion remaining on it as last I’d seen. Jason must have cleaned me up. I couldn’t decide if that was thoughtful or just weird. It all started flooding back into my mind, everything from the night before. I knew I hadn’t dreamt it, and I could hardly believe it had happened, but what could I do about it now? I had to face facts. I had allowed my son to give me a handjob. Sure it was the best handjob I’ve ever received, but that didn’t make it okay. Whether I was under the influence or not, I had done something undeniably wrong. It was immoral, despicable, hell it was illegal. My flow slowly came to an end and I shook off. I put my pants back on and stood in front of the sink, rinsing my hands. As I stared into the mirror I told myself “Never again. This stops now.” Intoxication is no excuse for what I did, and I can’t let it happen anymore.

When I returned to the kitchen Jason had my mug of coffee waiting for me. I could also smell the toast he’d started.

“So before you say anything” he said, unprompted. “I just want to let you know that I really enjoyed last night. It was a lot of fun. And I hope you… agree?”

“Uhhm. Geez. Jay, I–”

“I know you weren’t expecting it to go that way, or anything. And if you think any of what happened is your fault, I assure you, it’s not.”

“Look.” I said, trying to get my words out. “I may have been a little tipsy, but I still shouldn’t have… allowed…” I didn’t know what I was trying to say.

“No. Dad. You don’t have to try to explain, or make sense of it or whatever. I enjoyed myself. And judging by the mess you made, you really enjoyed yourself too. Didn’t you?”

“It’s not that simple.” I said, looking down at my cum-stained shirt.

“Why not?” he asked harshly.

“Because. What we did… it just isn’t–”

“Oh come on, would you stop with that. If it’s not right, then why did it feel so fuckin good?”

“Because that’s how sin feels sometimes.”

“Ha! Sin? Since when are you religious?” He had me there. “Okay, let me ask you this. Do you love me Dad?”

“Of course I do.” I replied with a sigh.

“Right. And guess what. I love you too. So what exactly is so wrong about two people who love each other wanting to make each other happy?”

“Well–”

“Nothing. The answer is nothing. Whether it’s emotionally, or physically, what’s the difference? I want to see you happy Dad. I want to be the one to make you happy.”

“That’s really–”

“You know what the best part of last night was for me?” He asked, and then continued without waiting for a response. “It was watching your face, that moment before the first shot of cum sailed over it. It was even better than when I came myself, because I knew then that I’d shown you a pleasure you hadn’t had in so long.”

I had lowered my coffee to the counter, and stood there stunned by his words. Just then, the toast popped up.

“Anyway, I just want you to know that I don’t regret any of it. And I hope you don’t either, because I’d like to continue to make you happy. That’s what family’s for.” He plucked his toast out of the toaster, and casually spread some jam on it. I didn’t know what to say. I didn’t know how to argue against his point. I stayed silent too long, and he just tossed his toast on a plate and walked away. I’d missed my opportunity to speak up.

I took a shower before work, to try and wash away the horrible feelings I was having, but it really didn’t help.

Throughout the morning I tried to get some work done but I really couldn’t focus. My head was hurting and I was just too overwhelmed with thinking about what I could possibly do about our situation. At lunch I decided I needed to go have a talk with my son and lay down the law once and for all.

I tapped on his bedroom door. No response.

“Jason?” I said with my face right up against the door. “Can we talk?”

“Uhh. Yeah. Hold on a sec, I’m in class.” He shouted.

A few seconds later, he told me it was all clear, so I opened the door. Jason was just lowering the lid of his laptop as I entered, but left it open a crack. An unusual odour hit me when I walked in, but I couldn’t quite place what it was. He swiveled around in his chair as I walked over to his bed and attempted to sit down.

“Uhhm. Here. You sit here Dad.” He said abruptly as he ejected himself from his chair and practically lunged towards his bed. He was acting very suspicious. Something was up.

“Uhh, okay. Sure.” I agreed hesitantly. I noticed him shuffle his sheets about when he sat down on the bed and I took a seat in his computer chair.

“So what’s up?” He asked casually.

“What do you think?”

“Come on Dad, I thought we talked about this?”

“Well, sure, you did some talking, but I didn’t really get to say my piece.”

“Oh? Okay then. I’m listening.”

Something was definitely off. He was acting strange. I looked around the room for a second to see if I could tell what was going on. That’s when I spotted it. His dildo, MY dildo, was peaking out from under his ruffled bed sheet. I narrowed my eyes at it and he gave me a face as if he’d been caught. I spun my chair around and bent my head down towards his laptop, when I could barely see the screen still lit up. I instinctively opened it up full and moved my hand to the touchpad.

“No no!” Jason pleaded suddenly.

I saw the browser window down in the taskbar, clicked it, and up popped a window full screen. Low and behold, it was porn. Not just any porn either, it was what appeared to be a live cam of another young man wearing nothing but green panties and some kind of chain attached to both his nipples.

“What the fuck!” I yelped as I slammed the laptop closed and stood up angrily.

“Don’t freak out!” Jason said, holding his hands up like I was the police.

“What is this shit Jay?” I shouted. “Is this what you’re doing in here? You’re not in class!”

“No. I was in class… earlier.”

“Is this fuckin LIVE? Are you and this… other boy… on cam… what? Jerking off together?”

“No!” He answered. “I’m not on cam. I wouldn’t do that. I know I’m not old enough. Don’t worry. I’m just… watching.”

That was a relief to hear. But I was still furious about this situation and wanted to push for more answers.

“So what’s that for?” I asked, pointing at the dildo tucked under the fold of his bed sheet.

“It’s just. I mean… I was watching, and… you know… enjoying myself.” He replied as he slid the toy out from under the sheet. That’s when I saw it was glistening and suddenly the odour I had smelled earlier got a little more pungent. It was the lubrication he’d put on it. It had a scent of strawberry, I think it was.

“Jesus Christ Jay. Is this all you do? All you think about? Are you just all about sex now and nothing else?”

“No. Geez.” He said slumping his shoulders. “It’s just… I was on with my friends after class, and they were asking me what I wanted for my birthday, which just got me thinking about… stuff. So I couldn’t help myself, is all.” He explained.

He twirled the dildo in his hand a bit and was gazing at it longingly. That’s when it struck me how odd this was. Why was he acting so sheepish and secretive about this after everything that had happened last night. And even this morning he’d taken control of the narrative and tried to tell me how none of it was a big deal. Was this some kind of act? Or was last night the act? It’s like this was a whole different Jason. One of them has to be fake.

“Why?” I asked. “What do you want for your birthday?”

He looked up at me with puppy dog eyes and I knew instantly, this was the act. He was about to try to convince me of something. In fact you might even use the word seduce.

“There’s really only one thing I want for my birthday.” He said, feigning innocence. His eyes drifted down my body and landed at my crotch.

“Oh my god.” I said, rolling my eyes. “Come on Son. You can’t be serious.”

“It’s what I’ve wanted for days now.”

“Oh you didn’t get enough of it last night?”

“Not what I truly wanted, no.”

He was grazing his fingers along the dildo replica of me now, spreading the lube around it.

“Well too bad!” I said firmly. “Because that’s exactly why I came in here. To put my foot down and put a stop to any more of that.”

“That’s not fair.” He pouted. “It’s my birthday.”

“You’re birthday isn’t until next week. And I’m sorry to say, you’re not getting what you want.”

“What if I’m a really good boy?” He said seductively, shifting his voice to a more feminine tone. “What if I’m a really good… girl?”

He was really trying now.

“I’m telling you it’s not going to happen. Ever again.”

“But I made you feel so good last night.”

“That’s not–”

“Just imagine what else I can do.” He said as he shifted his weight to the side and pulled on the waistband of his shorts, beginning to slide them down.

“Jay, don’t.”

He slid his shorts off his hips and down over his legs, kicking them off slowly with his feet. He was wearing another pair of his Mom’s panties. They were stretching and straining against his thickening cock.

“I just want the real thing in my mouth.” He said softly, holding up the dildo inspecting it. “Just once, at least?”

“You know tha–”

“I’m really, really good with my mouth.” He said breathily. “Don’t you want to find out how good I am?”

“No!” I shouted. But my body betrayed me. As I looked down at his smooth, slim legs and the tight panties I could feel my own engorgement beginning. He was fiddling with the dildo and my mind instinctively imagined it was actually my dick he was handling. The night before sprang into my mind and within mere seconds my pants were having trouble hiding my excitement.

“Are you sure?” He said with a sly smile, as he looked directly at my crotch again. “You might want to tell your dick that.”

I looked down and could do nothing to deny it. It was painfully obvious that I was getting an erection. My god. What a sucker I am. How easily am I swayed, that this is all it takes to be seduced? By my own son, no less. A member of the same sex, of the same family, and yet I can do nothing to stop my impulses from coming on.

It was at that moment that I broke. I let go of all notion or morality or ethics. I gave in to my carnal desires, and basically just… let myself be seduced.

“Well. Fuck.” I said defeated. “Happy early birthday, I guess.”

Jason didn’t need another word. He quickly dropped onto the floor in front of me, setting the dildo down beside him, careful not to let it tip over. He whipped off his t-shirt in one swift motion and then reached for the button on my pants. In a few short seconds he had my pants and underwear down around my ankles and was staring face to face with my slowly enlarging dick.

At first he just stared at it admiringly. Then he finally reached for it and gave it a good hard squeeze with both hands. In the light of the mid-day and with sober eyes, I noticed his hands barely wrapped fully around it.

“Whoa.” He said softly.

And with that, he opened his mouth and dove towards me. In one fell swoop he devoured my cock as if it was his favourite food. I was pushed back, my butt landing on his desk, as he pushed onto me with his head. The warmth of his mouth on my dick was like nothing I’d felt in literally a year. I braced myself on the desk and let out a nice groan of delight. Jason kept his face pushed against me and I looked down to see his nose firmly buried in my pubic hair. My cock was fully engulfed by his throat. He held there for a moment and I could feel his tongue working on the underside of my dick. It felt heavenly. He slowly backed his head off of me, taking a deep breath as he did, finishing with a satisfying “ahhh” after releasing my dick fully.

I saw a look of absolute bliss on his face, as he began to lick and caress my cock softly, lovingly. It was still enlarging, and I think he just wanted to watch it fully stiffen. It didn’t take long. After a few more seconds of caressing and massaging of my balls and shaft, it was as hard as it was going to get. He marveled at it again and gave a soft kiss on the head. Then several more open-lipped sensual kisses down the shaft, as if he was making out with it. He kissed his way back up to the tip before bending it down towards his lips and taking it back into his mouth.

What followed was a series of sensations that I can’t even describe. He took his time slowly making love to my erection with his mouth. He swallowed me down deep into his throat, then backed off and tongued my dickhead with care. All the while massaging my balls with one hands and using the other to stroke whenever my shaft was exposed. I’d never received such attentive servicing before. It felt like heaven. I put my head back and just enjoyed every second of it. And so did he.

I heard him moaning with pleasure, and saying “Mmmm” or “Ahh yeah.” Everytime he took a breath. He would take short breaks and pump my shaft for a few seconds before hungrily taking me in again. It felt like hours, I was in this bliss, when I’m sure it was really only mere minutes. But I felt the familiar signs of my orgasm building and opened my eyes to look down and watch the last few moments of this amazing experience.

I was watching his hot mouth intently now, and I think he knew I was getting close. Between the thrusts of his face on my cock, I saw his own dick was free of the panties, and he was stroking it as well. His motion wasn’t just his head through, he was moving his whole body while he fucked me with his mouth. That’s when I noticed the dildo was missing from beside him. It hit me; holy fuck he was riding it. Just as I realized that, he slammed himself down on the floor while at the same time pushing his face all the way down my shaft. He started moaning and shaking uncontrollably. I instinctively put my hand on the back of his head to keep my hardon deep in his throat. It struck me that this was the first time I had touched him throughout all this sexual exploration. It felt good, running my hand through his long wavy hair. That’s when I felt the warm bursts hitting my feet. This moment was pure ecstasy for him. My son has got my thick dick down his throat and an exact replica of it deep in his ass at the same time, while he erupts in pleasure.

It was all too much for me. The thought of his filled ass. His obvious state of pure pleasure. His hot, wet, moaning mouth devouring my cock. I couldn’t hold it for even a second, and I surrendered to the same ecstasy. I let go of a forceful blast in the back of his throat and he immediately pulled off of me, gasping for air. We both let out loud grunts as he finished spewing spunk on the floor beneath us and I unleashed the rest of my load onto his waiting face.

“Ah yeeeeeah. Daddy, give it to me.” He cooed.

I did as he asked and pumped string after string of my warm juice across him.

“Fuuuuck. Yeah. Just like that. Give me more Daddy.”

He was stroking my erection hard now trying to get more cum out of me. I watched in amazement as more thick globs covered his nose and lips.

“Mmmmmm. Yeah. It’s so good.” He moaned.

His pace on my shaft slowed as the last of my cum dribbled out. He gripped it tightly and milked it from base to tip just as he’d done the night before.

“Every. Last. Drop.” He said as he tried to open his cum covered eyes.

I felt my knees weaken, and my vision blurred in a haze of post orgasmic bliss.

So… That’s how we got here. Me and my son.

My sissy son.