My sissy son 1.

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.


"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.


"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.

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