My Sissy Son - Part 2 free porn video

This is a FigCaption - special HTML5 tag for Image (like short description, you can remove it)

When I think back to that moment, I knew I should have felt ashamed with myself. But while I was looking at his beautifully messy face and thinking about how we got to that point, I realized I wasn't ashamed. I wasn't upset with myself for being weak like I had been in our previous encounters. I wasn't embarrassed or confused. I was satisfied, content and to put it simply; happy.

I was happy because Jason was happy. When he carefully wiped my semen out of his eyes and scooped the sticky goo from his nose, cheeks and chin right into his mouth, he had the most euphoric look on his face. It was as if he'd waited his whole life for this moment. He held his mouth open wide and showed me how much I'd given him, then happily drank it down, remarking how delicious it was.

Looking past him to the floor I saw the massive splattering on the carpet beneath me. He had cum more than I did, and I hadn't had my penis inside of anything in over a year, so that's saying something. As I surveyed the whole scene, all I could do was smile, and think about his joy. I'd never seen my son as happy as he was in that moment. Granted, most father's don't ever get to see their son in the throws of ecstasy, but I'd done that for him. It was because of me that he felt such pleasure. I couldn't deny that it really made me feel good. I should have felt shame, but in reality my heart swelled with pride. I was able to show the boy who I loved most in the world the greatest pleasure of his young life.

So in the aftermath of that mind-bending blowjob I didn't run away from him. I stayed there and let us both revel in the feeling for a while. I didn't even pull up my pants right away. He was still on his knees, caressing my softening dick, kissing it softly, loving it. When we finally came back to reality, I stayed with him in his room a while and helped him clean up his semen from the carpet. By the time he finally got up from the floor and slid off of the dildo, I'd totally forgotten it was there. He plopped it on his desk and I couldn't help but chuckle.

"You really love that, don't you?" I asked.

"Oh yeah." He answered quickly. "But not nearly as much as the real thing." He added with a smile.

I stayed with him for a while and we chatted, being sure to tell him at some point just how amazing the blowjob was. It wasn't like any normal conversation, but it also wasn't awkward or weird. He even made a joke at one point about how he'd eaten his own brothers and sisters. A day earlier and a comment like that would have had me asking what the fuck was wrong him. But for whatever reason, I just laughed it off. Somehow the whole thing felt okay, it felt normal. Like I said, everything changed at that point. Our relationship would never be the same and we both knew it. Something in my brain told me to accept it, so I just... did.

Over the next couple days his horniness would lead to the odd handjob here or there. Okay okay my horniness as well, now that I could no longer deny it. Each time it got a little easier and more natural.

He had started wearing nothing but underwear around the house on a regular basis. And not his own underwear anymore, his mother's panties. It got to the point where I'd have to shut the curtains in the living room so neighbours couldn't see in. But I didn't mind. I started to really enjoy it actually. His plump little bum looked great in those panties and he hid his package so well sometimes I forgot it was even there. He started to have this real sexy, smooth attractiveness going on. He even walked a little different, and did his long wavy hair up in feminine styles. If he'd had breasts I would honestly have a hard time telling he wasn't a girl. I had to admit it was beginning to drive me wild, having a sexy little thing like that walking around the house all the time.

Part of me wanted to see what other looks he could pull off. So a couple days before his birthday I was lying in bed with my laptop and I decided to get him something thoughtful, in addition to the computer stuff he asked for that I'd already bought for him. I remembered what he'd told me that night we played truth or dare. He wished his mother had some knee-high socks that he could wear, but she never owned any. I went online and picked out three pairs. Two were just fun colourful stripes, but one had a pretty bird pattern. I thought that was perfect because his mother used to call him Jay-bird when he was small. I ordered them for delivery and just hoped they would come in time for his birthday.

Just as I closed my laptop and shut off my light I heard a knock on my bedroom door. I told him to come in. He slowly pushed it open and just stood at the doorway, silhouetted by the hallway light in the darkness of my room. All I could see was a sexy skirt, bra and pigtails. He leaned against the doorframe, suggestively.

"Hi Daddy." He said in a soft, breathy tone while he ran one hand down his torso. I knew exactly what he wanted. If the outfit wasn't enough, his first words were a dead giveaway. I'd caught on by now that he only used the term 'Daddy' when he wanted some action, or more specifically wanted my dick.

"Well look at you" I replied, admitting to him, and myself, that I was also in the mood and very willing to get some.

Jason slowly entered my room, each deliberate step sexier than the last. As he approached me I noticed the front of his skirt was bulging out. He was getting hard already and he hadn't even touched me. I smiled and slid the bedsheets off of my legs, revealing my body in it's nude entirety. I sleep naked, which was no surprise to my son, but still his jaw dropped. I squinted my eyes to see his face in the darkness and all I could think was how badly I wanted his talented mouth on my cock again. It started to rise at the thought.

He finally reached my bed and leaned down to crawl over my legs. I spread them open to make room for him to sit. As his hands landed on either side of me my wish came true, and his mouth immediately found my hardening cock. Like some kind of hungry animal, he threw his head around my crotch in circles, capturing the head of my dick with his teeth, gently of course. He slowly but surely sank my dick deep into his hot, wet mouth. I closed my eyes and let out a great big sigh of pleasure. His pig tails flopped around on me, tickling my stomach as he began to work his magic. He slid his mouth off my shaft, letting it smack down on my body, then lovingly licked it from top to bottom and sucked one of my big balls into his mouth. With a pop, he released it and then immediately went for the other. What a sensation, gently massaging with his tongue. He went back to my cock and sucked it down deep again. Then he began to quickly pump his head up and down on my solid shaft, bobbing and weaving, twisting and sucking. It didn't take long before I felt the familiar rising of a release coming.

Suddenly he pulled off and sat up, his hair flying in circles as he did. I looked down and saw him pumping his own hardon. that's when I realized he hadn't even used his hands this whole time. That's because he was using one for balance, and the other on himself. He sat up between my legs masturbating his long dick over mine, for just a few more seconds. Then he threw his head back and moaned in this high-pitched feminine cry. "AAAAHHHhhhhh yeah". He bellowed as he proceeded to empty his seed onto my crotch. I'm pretty sure my mouth dropped open as I watched his little balls contract and his dick pulsate, throb after of throb of orgasm juice. He finally looked down too and aimed the last few shots of his cum to ensure they landed on his target. With a final anguished moan as he milked out the last drops, he grinned and shuffled back to his previous position. This time with his ass up high in the air, he bent his head down towards me again and began to lick clean the mess he'd made on my cock and balls. He lapped it all up with a fervour, sending shivers through me in the process. I was in awe of his hunger for cum and cock. It was sending me over the edge and he hadn't even taken me fully in his mouth again yet. When he finally licked up the last drop and brought his mouth to my dick tip I was almost ready to explode. As I felt my cock enter his hot mouth again I couldn't resist reaching out and grabbing his pig tails.

"Mhmmm" I heard him moan, encouraging me. His lips surrounded my big swollen head and his tongue massaged my frenulum. That was all it took. I grunted out loud as I erupted and pulled sharply with both hands. I couldn't help it. That's when he finally grabbed my shaft with his hand, when his mouth was forced further down my thick dick. After the first shot I eased up a bit. He held it firmly and just kept his mouth around the tip, continuing the tongue massage. I relaxed my grip and just pumped shot after shot of his little brothers and sisters into his wanting mouth. He stroked my shaft with his hand while I did and never stopped tonguing me at the same time. I heard him "Mmmhmmm" again as he accepted everything I had.

As I came down off my orgasm, I let go of his pig tails. He held my head still in his mouth but looked up to meet my eyes. I saw another grin. Then slowly he slipped his pursed lips over the tip, careful not to spill any of his reward. I saw his throat move as he swallowed fully. He gave my dick one last kiss and let it rest on my stomach.

"Mmmm, thank you Daddy." He said quietly. "Now I can sleep."

I didn't respond. I was still breathing heavily and sort of out of it, ready to pass out myself.

He patted my leg as he got up off my bed and carefully slid my bedsheets back over me. Then he fixed his skirt and walked out of my room, closing the door behind him. I drifted off to sleep within seconds.

I awoke the next morning thinking it was a dream. But when I pulled off my covers I saw some left over sticky evidence that it had in fact happened. All I could think was how much I couldn't wait for the next time it would happen again.

But the next couple days were a bit busy. I had a lot of work going on and Jason was looking forward to his birthday, spending a lot of time chatting with friends. On the phone, or on video chat, or texting constantly. It was good to see him excited, though I didn't really understand why it was such a big deal given that we were still in lockdown and it wasn't like he could have a party or even see his friends. I guess either way, the 18th birthday is sort of a big one, and at least it was something to enliven the week.

When I was on my lunch break, reheating my leftovers, I saw Jason's tablet sitting on the counter. It kept lighting up and dinging. He was in his room texting friends on his phone, but because his devices are all linked it was coming through on his tablet as well.

I couldn't help but glance over each time the screen came on.

- Are you ready for tomorrow?

- Hell yes! I've almost got it all set up. As long as my Dad got me the rig I asked for, I'm ready

- Awesome!

- Can't wait to see you.

- Thanks bro.

- I'm really looking forward to finally doing it.

- Me too!

- LOL

- LoL

- It's Jaybird right?

- That's your account?

- Yep!

- Just do a search on the site and you'll find me.

The microwave beeped, distracting me from the rest of the conversation.

What on earth were they talking about? He must be planning a big online gathering or something. But I wondered what website that was. He mentioned the birthday gift he'd asked me for. He sent me a link to this adjustable camera stand that you mount to a wall or desk and then you can move it into position and it'll stay put. Pretty neat contraption actually.

A few months after the pandemic started, once I started working again, I realized it was going to go on for a while so I got both Jason and myself new webcams. I figured if we were going to be home all day every day online we might as well have some good hardware. They are nice full 4k high quality cameras and I know he gets a lot of good use out of his, in classes and with friends, every day. So I got him this rig he asked for to go with it, but I also got him a ring light, which he didn't know about yet.

If I'm honest though, now that our relationship has changed so dramatically, I'm more excited about giving him the clothes I bought him than any of the fancy computer gear.

My mind wandered a bit while I thought about what big birthday event he was planning with his friends, but ultimately whatever it is is none of my business so long as he's home and safe. I went back to work and practically forgot all about it.

The next day was Jason's birthday. The package had arrived just in time so I was pleased to be able to give him all his gifts.

I was up pretty early and wanted to make him some breakfast for when he woke up. To my surprise when I left my room I found he was already in the shower. The bathroom door was open a crack. He'd started doing that now, leaving the door open, probably trying to get me to spy in while he showered. I can't say it didn't work. I watched him for a little while, soaping his legs and then grabbing a razor. Obviously he shaved his legs but I'd never seem him do it. It was kind of sexy to see his leg up on the tub, the razor gliding smoothly. He hadn't noticed me but I didn't want to stare, so I continued on to the kitchen and started cooking up some french toast, his favourite.

It took a while for him to finally join me. He'd spent quite a lot of time in the bathroom, presumably grooming I suppose. But whatever he did, the result was fantastic, he looked amazing. His skin was fresh and clear, his hair was blow-dried straight, his super smooth legs and butt looked amazing in his blue panties. The little crop top he picked out showed off just a bit of his lean tummy.

"There's the birthday boy!!" I exclaimed as I took him in. "Happy birthday Jay!"

"Thaaaaaaaanks Dad." He said, rolling his eyes and blushing slightly.

"Grab a seat. I made french toast for your special day."

"I thought that's what it smelled like in here." He replied. "Thank you!"

"So? How does it feel to be eighteen?"

"Actually... Kind of different to be honest."

"Yeah? How so?"

"I don't know. Just... a little freer, I guess."

"Well, I must say, you look amazing." I blurted out, completely distracted by his convincingly feminine look.

"Yeah? You like?" He asked, as he raised his arms and presented himself to me.

"I love it." I replied. "I think 18 really suits you." I added, trying to steer away from my obvious horniness.

"Thanks Dad."

Dad. He's still calling me dad, not daddy, so I'm sure the last thing he's thinking about on his birthday morning was my cock, even if I couldn't take my eyes off his panty-covered ass.

We both sat down and enjoyed some breakfast. While we were eating his phone started blowing up with messages of birthday wishes from his friends and our family. When we finished I asked him to put the dishes in the sink and I went to grab his gifts.

When I returned to the kitchen with his gifts in hand, I saw a hint of excitement on his face. He opened the bigger boxes first, and thanked me profusely for getting him the stand he'd asked for. He was surprised by the ring light and seemed grateful for that as well.

But just as I'd hoped, I saw a much more satisfying emotion on his face when he opened the knee-high socks I'd got him. I could tell it really meant something to him, just as it did to me. I think he knew it meant I had not only listened to what he wanted but also was accepting and even encouraging of who he is and wants to be.

"Oh thank you Daddy!" He said as he threw his arms around my shoulders in a big hug. Daddy eh? I think I did good.

"You're welcome..." I replied quickly, slipping my arms around his slender back, pausing briefly then adding "Jaybird."

He loosened his grip and pulled his head back a bit so we were face to face. I kept my arms around the small of his back. He had a smile on his face and for the briefest of moments I thought he was going to kiss me, but instead he said "That's why one has birds on it."

"Of course." I answered.

"They're beautiful! I love them!" He yelled, throwing himself over my shoulda once again.

I gave him a good hard squeeze and said "I'm glad!" Then I released him from my grip and he let go of me as well.

"I'm going to go put them on." He said excitedly.

"Alright, you do that. Unfortunately I have to get to work." He frowned at me. "But I'll come and help you get that camera stuff set up on my lunch break, okay?"

"That would be great. Thanks again!" He replied, going off to his room.

I worked through a fairly busy morning. Jason had come to show me his outfit with the new bird socks at one point, but I was on a call so all I could do was smile and mouth the words "You look great". He had happily gone off back to his room. But it was hard to stop thinking about how great he actually looked. He'd leaned against the doorframe of my office showing off the sexy panties and top and sliding his fingers along his legs, smoothing the socks. Work was becoming hard to concentrate on.

Finally my lunch break came, and I took off my headset and went to find Jay.

He was, of course, in his bedroom. I knocked on the door and it slowly opened on its own.

"Oh, sorry." I started "I didn't know it was ope--" My words were cut off when I saw Jason on his bed.

He was lying sideways, with one hand on his hip, looking backwards seductively at me. The cheeks of his plump little bum were perfectly separated by a g-string now, and his hip curved beautifully into his crop top. The high socks accentuated his long smooth legs, and he had pulled his hair back into a ponytail, letting it fall on his shoulder.

He raised his hand off his hip and curled his finger several times, urging me into the room. I complied.

I slowly stepped in the room and my mind went blank, as if I were on autopilot. I didn't know what would come next but I knew I wouldn't resist, no matter what he had in store for me. As I got closer, he slid himself over the edge of his bed, turning onto his stomach. With his legs bent at the knees and his feet in the air showing off the socks, I couldn't help but stare at his ass as it flexed and bounced while he turned towards me. Without words, he immediately began to unbuckle my pants and within seconds my meaty cock was staring him right in the face. He held it for a moment, feeling its weight, and then slowly but surely pulled it deep into his mouth. He tongued it for a while, letting it solidify until it filled his throat completely. I looked down in awe, watching my beauty boy swallow down my cock yet again. His eyes were closed and he moaned with delight.

After we both enjoyed it for a while, he finally pulled off me and spoke.

"Mmmm Daddy. It's so good." He whispered, slowly tickling my dick with his fingertips. "This is the best present of the day." He continued. "The one I've been waiting for."

"Well, happy birthday son." I replied with a grin.

He smiled and looked up sheepishly now. "This isn't all I want though. What I really want for my birthday..." He paused, feigning shyness, though I'm pretty sure he was just doing it for dramatic effect. "I want it inside me. I want YOU inside me daddy." Staring into my soul with big puppy dog eyes he added "Please daddy."

My jaw dropped.

He took that as approval, and got up on his knees. The g-string stretched when he moved and I watched his perfect little ass as he turned around to present it to me. My cock reached a whole new level of rigidity and I knew in that moment there was no way I would resist doing this. Ethically and morally this would be the final straw of wrongness. But looking down at this beautiful round ass with perfect milky smooth skin, I was ready to go straight to hell for it. I thought to myself - if my son wants me inside him, then I'm going to give him what he wants. It's his birthday after all.

He turned his head to look back at me, his pony tail falling to one side. "Give it to me Daddy. Give me my gift." He said, as he pulled the g-string to the side, revealing his rosebud. Below it his little balls were cupped in the panties and barely visible. In fact it could have even been mistaken for a juicy swollen pussy if you didn't look too hard. I reached down and helped the g-string aside which allowed him to let go and put his hand back on the bed for balance. I noticed his asshole was already lubed. He must have prepared for this. I didn't wait any longer and bent my boner down to towards him. As the head touched his hole I heard him moan lightly. In fact I think I did as well. I slid the underside of my thick dick along his crack, in long full strokes, getting it nice and slick. Even just this sensation was sending shivers through me, I could only imagine what actually entering him would do to me. But I didn't have to imagine for long, as I lost my propensity for foreplay and could no longer resist the main event. With my hand on his ass cheek, thumb holding the g-string to the side, I had to push my rod downwards it was so hard and upright. I placed it directly on my son's hole and with a firm thrust forward, entered him for the first time. As the big mushroom head of my cock disappeared inside him, we both groaned at the same time.

"Ohhhhhhh yeeeeeah." He moaned.

I slid deeper, watching my dick vanish inch by inch. His man pussy swallowed me as easily as his mouth had. It seemed almost effortless. That's not to say it wasn't tight, however, just that I suppose he'd been practicing for so long it was easy for him now. It was like nothing I'd ever felt. His mother had only ever let me fuck her ass once, and it wasn't particularly pleasurable for either of us. But this, this was heaven. His hot hole engulfed and squeezed my dick like it was made to do it. By the time I had fully pushed in the the hilt, I was ready to cum. But I didn't. I had to hold off. I had to give him his gift.

I rested my massively swollen cock fully inside my son for a moment while we both reveled in the feeling. I moved my free hand to the small of his back and he fell forward off his elbows, putting his face and shoulders into the bed. It dawned on me then that this was the first time I'd really touched him like this. I kneaded my hand into his skin, feeling how smooth it was. I squeezed his ass cheek lightly and let my other hand explore his back.

"Oh my god Daddy." I heard muffled in the sheets. "It's sooooo good."

"You like that?" I said, without really thinking.

"Mmm I LOVE it."

With that I began to pull out of him, all the way until I saw my head appear, then pushed in again. I slid back in easily, stretching his hole as I did. My god what a hole! I could still barely hold back my cum, but began to rock in and out of him now. I wanted him to feel the full long strokes of me reentering him with each thrust. I began to lose myself in it, staring down, watching this ass take my cock like no other ever had. I was going slow but firm and pushing hard each time, making sure I was fully inside before going again. He was groaning consistently and his muffled cries were just egging me on. He finally turned his head and I could hear him clearly repeating his favourite words.

"Give it to me. Give it to me. Give it to me Daddy."

I'm really not sure how long I lasted, but it probably wasn't long. Soon enough, I gave him his wish. I pulled hard on both his hips while I skewered him one last time and exploded deep into his bowels. I think I grunted like a madman as I emptied my balls into my son, all the while he begged and encouraged me to keep cumming. Wave after wave of orgasmic bliss washed over me as I injected my seed into his heavenly hole. When my balls were finally drained, I eased my grip and let my hands glide over the plump cheeks and caress his silky back.

He propped himself back up on his hands and looked back at me. Slowly and smoothly I withdrew my spent cock from him, and watched as his gaping cavity spilled my white nectar. It flowed over his panty-covered balls and down onto the bed. He giggled and his ass puckered suddenly. I took a step back and he spun onto his side, flopping down on the bed again, with a satisfied "ahhh".

"That was--" He started

"Incredible." I finished.

He smiled and looked at me. "Yeah. Exactly." He said.

I flopped myself down on his chair, exhausted. He just lay there, running his fingers over himself, caressing his own butt, and rubbing some of my cum in places. He fingered his asshole a couple times and softly rubbed his balls through the panties. I just sat there, watching. Then it hit me that he hadn't had his own orgasm through this. I could see a definite wet spot in his panties, but it must have just been precum because it certainly wasn't enough to be one of his plentiful loads. With all our previous encounters he always liked to cum too, but now, on his birthday, he hadn't. I felt bad.

I spoke up "What about you? You didn't..."

"Hmm? Ohh.. no that's okay. I don't need to right now. This was amazing just as it was. I'm veeeery satisfied. Trust me." He explained.

I still felt bad, but I wasn't exactly willing to take care of him like that, at least I don't think I was. So I let it go and after some recovery time, we both got up and cleaned up.

Afterwards I helped him set up his new camera rig, drilling it to the wall between his desk and his bed, as he requested. We finished attaching the camera and the light and everything was all set. It was a cool rigging arm that he could move and swivel around a few feet in all directions and the camera would stay in position. A new and improved set up just in time for birthday video calls with friends and family.

I had to go back to work, but had a real hard time concentrating at all anymore. My mind was swimming with the fact that I'd fucked my son for the first time, on my lunch break, on his 18th birthday. My whole life had changed so much in the past year but it all seemed like nothing compared to this.

But Jason had plenty going on, and I had to meet some deadlines so we didn't end up together again until dinner.

Throughout the day, there were tons of phone calls and a few deliveries. Jay answered them all knowing they'd all be for him on his special day. When I finally emerged from my den at 5pm I discovered a few empty boxes and some flowers in the living room. Above them floated two big balloons in the shape of a one and an eight.

I wanted to go see what he was up to, see if he was waiting for me to come into his room again, but I resisted. I wanted to get dinner started.

So I powered through cooking and dinner, trying not to think about my son's inviting ass, or mouth, or hands. Trying not to picture his arching back in front of me while I hold his ponytail and go balls deep in his ass. Trying not to imagine his talented tongue licking my sack while my dickhead swells in the back of his throat. Trying not to remember how lovingly he caresses my manhood like it's the most beautiful thing he's ever touched. It was all I could do, to sit there eating with him, while he told me about his day and not throw everything off the table and bend him over it.

But I made it through without incident, because I knew we had a video call planned with the family right after dinner. He sat down on the couch and set up the laptop while I did the dishes and then got out his cake. I heard him saying hello to the family while I was putting the candles on it. I could see the laptop from the kitchen and waved to everyone on screen. I lit the candles and started walking over with it. As I approached Jason from behind I started singing happy birthday, and everyone on the call joined in. By the time the song was over I'd sat down beside my son and was holding the cake in front of him. Bashfully, he closed his eyes and blew out the candles. Everyone in the laptop applauded.

It was a surreal circumstance, sitting there so close to my son, who just hours ago had my hard dick in his ass, talking to all of our family together. At one point someone said something funny and Jason inadvertently slapped his hand on my leg, but then he let his hand linger there for a bit too long. I wondered if anyone noticed it. But by the end of the conversation my sister had commented that the two of us seemed closer than we used to be and it was nice to see. Jason and I looked at each other in that moment and we both smiled. If they only knew just how close we were now. If they only knew.

After our call with the family I was wondering if Jason was going to initiate anything else with me. If I'm honest I suppose I was kind of hoping for it, but it was not to be.

I knew he had some big event planned with his friends, based on what I'd seen on his tablet earlier, so I wished him one last happy birthday and retired to my own privacy so that he could have his.

It wasn't late enough for me to want to sleep, so I cracked open the laptop and tried to get my mind off my son with more work. But after an hour or so of trying I just couldn't stop thinking about it. I wondered what this big thing was that he was doing with his friends. But I'd promised him his privacy and I would not betray that. I thought back to those messages I saw. "Jaybird" I thought. Did he tell his friends that was his mother's nickname for him? Maybe it was the password for the chatroom or something. But no, his friend had said that was his account name. But account for what? The more I thought about it, the more I couldn't shake the feeling that something was going on. After everything we'd been through lately there was still something off. He's up to something.

Then it dawned on me. The first time he gave me that stunning blowjob, he was on a website when I walked in his room. He was on a porn site. A cam site. Watching another boy masturbate. Today was his 18th birthday, and he'd convinced me to buy him new webcam equipment. He wouldn't. Would he?

I opened a browser window and instinctively typed in the same porn site I always use. I clicked on the magnifying glass icon and started typing...

J - A - Y - B - I - R...

That's when the search result popped up. "Jaybird (18, M)"

I clicked.

The webpage loaded a streaming video, and there it was. A closeup of my son's gaping asshole, in glorious 4k. Up in the top right corner of the video was a red dot beside the word 'LIVE'.

My mouth dropped open and I clenched my hands. My immediate reaction was anger. As I sat there seething with rage I surveyed the page. The title of the stream was '[Free] First live show - 18th birthday'. There were currently 48 viewers. I wondered who they could possibly be. I could clearly see the bird socks on his legs and could make out some of the details of his bedroom in the background. But he also made sure to get the 18 balloons in the shot behind him. Somehow that made it even worse. How could he do this? This is so dangerous, so reckless. What if someone recognizes him. What if someone knows. I wanted to storm down the hall, burst through his door, and rip the camera off the wall. I couldn't believe what I was seeing.

But I had to think about the consequences of anything I might do. He just turned 18, technically he's an adult and can do whatever he wants now. If this is his life, who am I to judge? If I interrupt his first broadcast he may never forgive me. This newfound bond between us could be ruined forever. I may never get to slide my meaty dick in his deep dark hole ever again. It looks so inviting. Dammit. No! I shouldn't be thinking that, of all things.

But it does look so inviting. I had been fixed on the video while I thought about what to do, and without realizing it my penis had grown in my pants to the point of uncomfortableness.

Jason was fingering himself for the camera. Two fingers at the moment, and then adding a third. Soon his hand disappeared out of frame while his hole puckered a few times and then gaped again, as if it were waiting to receive something. Low and behold the thick purple dildo made its way into frame. He'd clearly already been fucking himself with it and happened to be taking a short break when I joined the stream. But back inside it went, quickly, easily. He moaned for the camera as it hit it's maximum insertion. He pulled it out quickly and slammed it in again. It seemed his show was getting to a certain point, I was just late to the party. My hands worked with a mind of their own as they yanked the waistband of my track pants down, and tucked it under my balls. With my cock out and stiffening, I had no choice but to just accept my son's new venture and see where it took him. I maximized the video on my screen and just let it unfold while I gripped my member with both hands and started stroking to the rhythm Jason had set for us.

He had laid on his side now, and pushed his cock and balls under his legs, then closed them tight. The camera, and his audience, were now staring at his tight sack and long hard dick straining against his legs while he pumped the dildo in and out of his used ass. He was picking up the pace now and so was I. Seeing the way his sensitive hole stretched and strained from this angle made me realize that's what was happening earlier in the day when it was my rod in there. I was jacking myself quickly now and I was ready to burst at any moment. Jason jammed the dildo deep in his cavity and with a great feminine cry, suddenly his meat surged and pulsed, and a great big squirt of cum flew out of the tip. I heard myself say "whoa", and watched in awe as more of his juice streamed out. It was so unexpected. He hadn't ever touched his cock, and he was cumming like he's been masturbating for an hour. I quickly beat my dick to catch up and a few strokes later I was joining the cum party. I barely even acknowledged my own semen splattering my chest because I was watching this close up of my son's pulsating dick dance on its own, unleashing a steady flow of cum all over his new knee-high socks. What a view! After 6 or 7 heavenly gushes, he started moving the dildo again. Still not touching his dick, the motion of the dildo seemed to milk out more of his sap, until finally he pulled it out and turned his ass to the camera for his audience to look into the abyss.

My own hand was covered in my ejaculate and I milked out the last drops from my dick and dropped it on my stomach with a satisfying sigh. On the screen, Jason finally turned around to face the camera. He had a facemask on, thankfully. And with his long straightened hair falling around it you couldn't see much of his face at all, just his eyes really. He winked at the camera, repositioned it for a wider view. He fell back onto his bed and showed the audience the big mess he's made on his legs. He winked again and then blew a kiss to his viewers. Then he waved and reached toward the camera. The video went black.

I happened to glance down at the viewer count. It was now over 100. I wondered if that would be considered a successful show. Even if it wasn't that looked like one hell of an orgasm he had.

All I could think was; someday soon, I hope I can do that for my son. My sissy son.

-->

Same as My Sissy Son - Part 2 Videos

3 years ago
  • 0
  • 59
  • 0

Sissy Stepson 10 Stepmothers Sissy

Part 10 - Stepmother's Sissy Mrs. Monet put another knee high on the exhausted sissy and got an open toed spike heel with a very small opening in the toe of the shoe. Mrs. Monet forced the shoe on the sissy's limp dick, which started to harden within the shoe. "Come on sissy, just three more milkings, I know your balls ache and your sissy stick is red and sore, but you promised to hump my shoes!" his stepmother cooed. Finally, Caroline's sissy stick got hard enough for the just the tip...

4 years ago
  • 0
  • 25
  • 0

Sissy Stepson 8 Carolines Milking

Part 8 - Milking Caroline "Our sissy is going to get ready for milking, I have enough knee highs for everyone to participate" said Mrs. Monet excitedly. She gave everyone three knee high's, sissy Caroline was going to get the milking of her life! Caroline came back to the group with here outfit on and was instructed to sit next to Regina for milking. Regina encased the Caroline's sissy stick with the nylon and instead of using her hand. She took off her high heel and stuck the toe...

3 years ago
  • 0
  • 17
  • 0

Sissy Stepson 9 Forced to Suck

Part 9 - Forced to Suck "Get over her you bitch NOW!" screamed and angry Maryann. Caroline's aunt grabbed his limp red puny dick and put the knee high. "What's a matter limp dick sissy, can't get it up for a woman, maybe you need some perversion or more man cock" crowed Aunt Maryann. "Look sister, he's getting a little stiff, he must love to be degraded" said his stepmother wickedly. "Lay down in front of my feet and Phil put a knee high on your cock and start jacking off in front of...

4 years ago
  • 0
  • 67
  • 0

Andersonville 21 Sins of the father Sins of the son

"Good morning, Miss Anderson," Crius said in a formal tone. "Please, call me, Linda," I replied. "Only if you call me, Crius," he answered. The Titan God smiled, but I detected no warmth to it. "Okay, Crius." I returned his smile with some reservation. I couldn't put my finger on it, but I didn't feel at ease with him. When he had asked me out to breakfast, I had been tempted to say 'no', but my curiosity had gotten the better of me. "So, what can I do for you?" "Nothing,...

4 years ago
  • 0
  • 17
  • 0

Sissy Stepson Part 5 Pantied and Punished

Part 5 - Pantied and Punished Carl begged his stepmother not to spank him and he pleaded, "I'll be good, I will never try your things on again, please!" "To late, you can't be trusted and must be properly punished, but first I want the truth about why you did this. If you don't tell me the truth I will make sure your father knows, his family, your friends and everyone at school!" Carl shook with fear and started to cry. "Please I couldn't help it, I am attracted to your sexy...

3 years ago
  • 0
  • 19
  • 0

Sissy Stepson Part 2 Sissy Heaven

Sissy Stepson Part 2 ? Sissy Heaven Carl knew she was going shopping, so he feigned being sick to stay home. He saw that his stepmother wasn't wearing her stilettos and this excited him. They would be his to explore and touch. She bitched at him, "You're not sick!" "Yes, I am, I feel sick to my stomach." plead Carl. "Well, I am still going shopping, I am not waiting on you today, you're on your own!" bellowed Mrs. Monet. "No problem, I just...

4 years ago
  • 0
  • 47
  • 0

Sissy Stepson Part 4 Stepmothers Test

Part 4 - Stepmother's Test She crossed her legs and began dangling her high heel again and Carl became excited. His sissy stick started to stick up as he watch the dangling show and fashion models prancing on the run way. He had no where to escape and his stepmother noticed her panties bulging with his sissy cock. She nonchalantly let the shoe fall on the carpet and said, "Well, missy are you going to pick my shoe up and place back on my toes or can't you get up!" "Yes, ma'am, I...

3 years ago
  • 0
  • 13
  • 0

Sissy Stepson Part 3 Caught in the Trap

Sissy Stepson Part 3 ? Caught in the Trap He was worried about the stain until he started watching a game show with the sexy female host. She had a stiletto's like he was wearing and was dangling them. Once again Carl's sissy stick became hard and began oozing translucent sissy cream all over the nylon and panties. He sat there for ten minutes watching the dangling, mesmerized and in a sissy dream like state with glazed eyes and an oozing cream stick confined...

3 years ago
  • 0
  • 209
  • 0

Andersonville 12 The Day Linda Anderson Came To Town

I slid the report into the proper file just as he walked into the room. Dennis Butz stood there wearing his three-piece suit, looking as handsome and charming as any man could. But I was not to be tamed by his charm. "Hello, Linda," he said with a friendly grin. "Judge Herns isn't in today," I replied back in a frosty tone. "I'm not here to see her." "My plane leaves in less then an hour Dennis, what do you want?" I slammed the file drawer shut and walked past him to my desk...

1 year ago
  • 0
  • 22
  • 0

Sissy Puppy Fifi Part2

Chapter 2 I tried as best as I could to get comfortable curled up in the corner of the room. At first I kept squashing my tail which either caused the vibrations to start or pushed the plug further inside. I had eventually worked out the best position to lie in when Mistress appeared. "Time for bed Fifi," she said as she attached the pink lead to my collar. I was then led through the house and up to her bedroom. This was a strange feeling to enter her bedroom not in my usual maid's...

2 years ago
  • 0
  • 25
  • 0

SISSY DANI PART3

CHAPTER THREEMistress Jennifer and Mistress Susan's plans to create an entire"harem" of transformed men and boys continued apace. The lure ofTeasing Tammy (the transformation name of Susan's teen-agedbrother Tommy) proved quite effective. Each of the young men (theyoungest just 14, the oldest 22) the little tease brought back tothe home we all now shared was turned into a different kind offeminized sex-toy, all designed to please the Mistresses andtheir dominant friends.The little...

3 years ago
  • 0
  • 20
  • 0

Sissy Dick Johnson

Sissy Dick Johnson by Throne He was really annoying. Dick Johnson was a wimpy guy. Short, unathletic, with his brown hair falling over his forehead and ears. At 21 he had no significant experience with females. And he was smitten with Angel Giovanni. She was stunning. Short and buxom, with her jet-black locks streaming halfway down her back. At 24 she had confidence born of being a sex bomb. And she was irritated by Dick Johnson. Since he had moved into her apartment...

2 years ago
  • 0
  • 47
  • 0

The Chronicles Of Sonali 8211 Part 5 Video Of Vinita Fucking Her Son Rick

The moment I typed ‘mom, the search engine immediately displayed ‘mom and son’. I found my index finger click on the mouse. It was as if a dam broke open and my jaw dropped to find out that there was so much of it. I filtered for videos and still, the search results seemed endless. After scrolling for around twenty minutes one video appealed to me as the lady in it looked similar to Vineeta – not Indian – but quite similar – some Latina pornstar. I watched the video for two minutes. However, it...

Incest
3 years ago
  • 0
  • 48
  • 0

Sonyas Siren Song Part 2 Educating Sonya

This story continues on directly from my first story, Sonya’s Siren Song. In the morning, I opened my eyes, and there was Sonya, in the bed beside me, still fast asleep. I realised that whatever happened last night had really happened, and there was no going back. I wasn’t sure what would happen when she awoke, but just in case, I quietly slipped out of the side of my bed, and put my pyjama pants back on.I looked down at the still-sleeping Sonya, lying with her back to me, and I remembered that...

Taboo
4 years ago
  • 0
  • 49
  • 0

The Chronicles Of Sonali 8211 Part 21 Son Cumming In Mom8217s Mouth

Joy clenched his jaws as he answered his father, “Dad, it is too good to describe. Mom’s mouth is out of this world, dad, almost unbearable. Oh, mom, I think your mouth is going to make me cum soon.” Suvendu gestured me to stop my head movements as he wanted to see his son cumming. “Hold it, Soni, don’t make him cum so soon. Son, take a break. I’ve special plans for your first ejaculation with a real woman. Let your cock get some fresh air while you watch your mother suck mine.” I moved my...

Incest
3 years ago
  • 0
  • 44
  • 0

The Chronicles Of Sonali 8211 Part 12 Best Cowgirl Sex For My Son

I went to the restroom to redo my hair and reapply my favorite cherry red lipstick. With all that friction of my son’s cock against my lips, the previous coat was wiped out. I was pleased to notice the glow on my face. No wonder, as Vineeta had mentioned, a young man’s cum does wonders for a woman. The intake of warm young cum in your digestive system generates a lustrous glow within a week. In one day, I had swallowed two huge loads. What a cum slut I had become. As Joy drove the car back...

Incest
3 years ago
  • 0
  • 124
  • 0

The Chronicles Of Sonali 8211 Part 6 Sonali Sees Her Son8217s Masturbation

That night I tossed and turned in the bed and tried hard to sleep but just couldn’t. images of Vini with her son and Joy fantasizing about me kept on bombarding my brain. And more than anything the words of Vini, “Sonali you should fuck your son,” kept me hitting like a torpedo. In the morning I hit the gym with a vengeance and sweated it out hard in an effort to get all that had happened out of my mind. It was nothing but a bad dream, I kept on telling myself and succeeded to an extent. I was...

Incest
3 years ago
  • 0
  • 133
  • 0

The Chronicles Of Sonali 8211 Part 10 Mom Loses Anal Virginity To Son

Joy put two pillows beneath my stomach so that my ass protruded up for his unhindered vision. I squirmed a bit as I felt a generous amount of almond oil drop in my asshole. It was followed by a gentle push of finger which started massaging my anal passage expertly. I could not believe that within a few minutes my son’s oiled finger was moving in and out of the passage effortlessly. Then he inserted the second finger and I felt a pressure in the rectal muscles. However, due to another dollop of...

Incest
4 years ago
  • 0
  • 48
  • 0

Sissy dannis birthday party

My last "true life" story was about how I became Heidi's sissy crossdresser "Danni" - I only explained the initial experience of Heidi coming home to find me in one of her dresses - followed by spankings, punishment and eventually getting pegged by her wearing a strapon. Of course there is MUCH more to what happened next (like being taken out in public and going shopping, to hair salons, etc...), but I'd like to for now jump ahead to what happened to me on my 19th birthday. By then I...

2 years ago
  • 0
  • 44
  • 0

Sonyas Siren Song Part 2 Educating Sonya

In the morning, I opened my eyes, and there was Sonya, in the bed beside me, still fast asleep. I realised that whatever happened last night had really happened, and there was no going back. I wasn’t sure what would happen when she awoke, but just in case, I quietly slipped out of the side of my bed, and put my pyjama pants back on. I looked down at the still-sleeping Sonya, lying with her back to me, and I remembered that under the covers, she probably still had her silk nightdress...

2 years ago
  • 0
  • 23
  • 0

Sissy Sisters Party

SISSY SISTERS PARTY by Throne Bob Clump, the friendly retired guy at the end of the street, was taking advantage of the mild weather of late Spring. He was sitting on his front porch enjoying a fine cigar. Or at least a cigar. Those fine ones cost a lot more than what he smoked. As he sat there, a car pulled up across the street, in front of the house diagonal from his. In the dimming light of dusk he saw two figures emerge. The first was a woman, quite attractive in a slender,...

3 years ago
  • 0
  • 21
  • 0

Sissy Girl Party

SISSY GIRL PARTY by Throne Danny felt so ashamed, standing there before his wife Melba in a pink and white party dress that would be appropriate for a nine year old girl, not a grown man like himself. He cringed inwardly and unconsciously took one of his short pigtails and wound it around his finger. His feet were shod in pretty ballet-type slippers, pink ones with little rhinestones on them. "You look so sweet, Dee Dee," she said with a smirk that he knew all too well. He had...

3 years ago
  • 0
  • 46
  • 0

The Chronicles Of Sonali 8211 Part 3 Vineeta Fucks Her Son

Rick looked at me with desire in his eyes and moaned, “Mom your lips are so juicy and hot.” And in a swift move put his lips on mine and started feeding on them. Such was the intensity that a short gasp emitted from my mouth. But got submerged in his soft groans of pleasure. I also found myself gorging on his mouth. Within a few seconds lost total control immersing ourselves in the most passionate kiss of our lives. I felt his penis growing hard and long and banter upon my thigh. It must have...

Incest
3 years ago
  • 0
  • 27
  • 0

Sonali Er Narom Sona

He iss readers, I am back after long time. Here I will tell u how I seduce my uncles sexy maid, sonali. I am from kolkata and I will tell the story in bengali. If anyone want to know, may write to me Sonali, bachor ponero solo er halka gom ronger meyetar sorir chilo khub akorsoniyo. Amar kakimar bari kaaj korto. Sbsamoy bra panty er sathe porto ekta paatla naity. Naity er arale or panty er rong majhe majhe bojha jeto, ar besirbhag samoyei or bra er fite beriye thakto. Ami takhon college e...

1 year ago
  • 0
  • 45
  • 0

The Chronicles Of Sonali 8211 Part 8 Son8217s Dick In Sonali8217s Pussy

Joy emerged from his room with an envelope in hand and entered my bedroom and came out with a smile of relief on his visage. “Ma, it was a great relief to write all my feeling for that unique lady. Read it with patience and tell me what you feel. You might get angry but all I have been is bluntly honest. Whatever will be your next step, I’ll accept it gladly.” “Why do you think I might get angry?” “Well, it’s not the matter mother and son usually talk about.” “I told you, dear, I won’t get...

Incest
2 years ago
  • 0
  • 9
  • 0

Sissy son in law

I met my wife Janine in high school, she was the hottest girl in class she is 6 feet 3 inches tall and a former model , she informed me that we'd be living together following school, but first I had to have her parents Okay so One weekend we went to see them her mother was as beautiful as Janine ,her father was a very mousey kind of guy . When I went into the parlor and asked the big question her dad ( Jeff) said it was okay with him, but carol said your not the type we were expecting. She...

3 years ago
  • 0
  • 29
  • 0

Sissy Bachelorette Party

'You want it again?' She said, as she climbed between my legs, spreading them with the force of her knee. 'Yes Mistress.' I said, turning my head to the side. Her gloved hand grabbed my chin and turned it towards her. 'You want to be my girly lesbian bitch?' She said, as she tweaked my puffy nipples with her other hand, the dry latex chafing me. 'Yes Mistress - I want to be your girly lesbian bitch,' I rubbed my horny cunt against her stocking clad leg, ignoring the pain, wanting, no, needing...

2 years ago
  • 0
  • 34
  • 0

Sissy spit roast sleep over

Pt 1: Long black limoSissy Saraya was very excited because her new mistress had told her they were going to continue with her corset training tonight, she had been wearing her waist trainer and inflatable plug all day along with her favourite pink maids outfit and cute sissy 6" white heels and stockings with pretty pink bows, She had been watching BBC porn all day and was dreaming of cock while she finished her chores, Mistress text to say her driver would be arriving at 6pm sharp, Mistress...

4 years ago
  • 0
  • 30
  • 0

Sissy School Part 3

SISSY SCHOOL - PART 3 By Missy Crystal After Sissy Heather had swished and drooled a couple of more times, she began to give me gentle nibbles and licks to clean the cummy residue on my lips and chin. After the kitty bath, she stood up. Since her crotch was now at my eye level and since her short skirt exposed her frilly panties, it was obvious that I wasn't the only one that got turned on by her sucking my dick. She must have been aware of it too, because she pulled her panties down...

2 years ago
  • 0
  • 34
  • 0

Sissy tasks

Your First Sissy AssignmentThis is your first step on your journey into femininity. A journey that will change your life. You will be humiliated and embarrassed. Most of all, you will be feminised. If you don’t intend to follow all of these assignments to the letter, then turn away now.Your first assignment is to buy yourself a pair of panties. Be sure to measure your hips before you set off. You will go to a smart department store or, better still, a specialist lingerie shop. How exciting – a...

1 year ago
  • 0
  • 19
  • 0

Sissy and Paul

The double ended dildo had appealed to her sense of humour and made her wet thinking about using it on me. Sissy and Paul Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married several months...

Mature
3 years ago
  • 0
  • 30
  • 0

Sissy School Part 6

SISSY SCHOOL - PART 6 By Missy Crystal The sissies flounced out of the kitchen in a train of swirling petticoats and went into the living room, which was also the classroom. I was the caboose, following Sissy Heather. As soon as we were all in the room, Mistress Mary appeared. Either she had ESP or she really was constantly monitoring us. Either way, I was glad I decided not to try anything for the time being. "Today we will have a deportment class," she announced. "Yeth, Mithtwith...

3 years ago
  • 0
  • 23
  • 0

Sissy Slumber Party

Sissy Slumber Party I was on my way to the slumber party and I was so excited that my panties were getting wet. As I felt the moisture between my legs I blushed and giggled. My high heels clicked on the sidewalk as I went and my full skirts and petticoats swooshed around my baby smooth nyloned legs. I wiggled down the street and my long curly hair and bangle earrings swung from side to side as I walked. Some men in a passing car whistled at me and I just smiled. But my panties...

3 years ago
  • 0
  • 34
  • 0

Sissy Farm Chapter Sixteen

Sissy Farm - Chapter 16 By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

3 years ago
  • 0
  • 31
  • 0

Sissy School Part 4

SISSY SCHOOL - PART 4 By Missy Crystal Mistress Mary came over and stood next to us. To my surprise, her voice was calm. "The purpose of discipline is correction, not cruelty. There is nothing to be gained by punishing a sissy for behavior that cannot be improved and no profit in breaking her spirit by making her fearful of mistakes over which she has no control. I do not require perfection. Only that each sissy tries her best to be perfect. You have always done so, Sissy Heather."...

1 year ago
  • 0
  • 41
  • 0

Sissy Farm Chapter Eleven

Sissy Farm - Chapter Eleven By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's brother.) James: AKA. Auntie...

1 year ago
  • 0
  • 45
  • 0

Sissy Emma is turned

Sissy Emma is turnedI had been a crossdresser all my life but completely in the closet and hidden from all my friends and family. To ease my tensions, I often chatted with people on line, at first with females and other crossdressers but as I got braver with men as well. I loved to chat with them and their strong demeanour made me feel even more feminine.I had been chatting with John for a couple of weeks, about my fantasies. And let me get this straight, that's all they were fantasies. I mean...

4 years ago
  • 0
  • 23
  • 0

Sissy Farm Chapter Eighteen

Sissy Farm - Chapter 18 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

2 years ago
  • 0
  • 28
  • 0

Sissy Hypnosis Fun

Sissy Hypnosis Bet I have always been something of a night owl, which means that I take a while to get up and going in the morning. My alarm generally goes off at 7am, I hit snooze two or three times, then I finally get up and hop in the shower while my coffee pot starts to percolate. I grab my coffee and try to head out the door by 7:45, which is just barely enough time to get me into the office by my 8am start time. Needless to say, I frequently arrive with my hair still wet and...

2 years ago
  • 0
  • 42
  • 0

Sissy gets a black master

Sissy Gets A Black MasterI got up wearily from my long and exhausting night being fucked andpunished by my new Black Master. As I awoke, I could scarcely believe thatall those depraved things had happened to me. One minute I had been merelyexchanging emails with a man, who could have been anywhere and the nextminute, that very man was at my door, in my home, and then inside mybody. Black Master, a man whose name I didn't even know, a man who lookedto be about ten years my junior, had taken me...

3 years ago
  • 0
  • 27
  • 0

Sissy Training at Last

Sissy Training at Last The email came at 3pm on the Saturday before my birthday. All things considered, I have to admit that His timing was perfect. I'd just returned home, and as I had the rest of the weekend free, I'd decided to have a little fun. For me, "a little fun" meant that I'd indulge in some sissy fantasy play. You see, I've been a closet sissy for years, and even though it's my main sexual kink, I hadn't really found anybody who wanted to make my weekend fantasy into my...

3 years ago
  • 0
  • 29
  • 0

Sissy Farm 20

20 Sissy farm List of Characters. Me. Michelle A Natural transvestite sissy. Janice My Younger sister Aunty Bev Janice and My mother's Sister. Mistress Janet Headmistress of the young lady's academy Doctor Shirley Williams. My endocrinologist. Miranda. A very effeminate Sissy sales assistant. Miss Stern Miranda's mistress who owns the shop. Peregrine AKA Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James AKA Auntie Jamie Peregrine's...

1 year ago
  • 0
  • 31
  • 0

Sissy Farm Chapter Fourteen

Sissy Farm - Chapter Fourteen By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty...

4 years ago
  • 0
  • 24
  • 0

Sissy Velina

I walk into the living room of my master. I am completely sissified and wear a very frilly sissy maid outfit. My 6" white leather peep too high heels have thick leather straps around my ankles and are closed with medium sized padlocks. I wish I knew where my master holds the keys. On my lightly sun tanned and smoothly shaved legs I wear white sheer seamed stockings and with a nice lace band at the top. At the back the pink seams end with large pink girly satin bows. Just above my...

3 years ago
  • 0
  • 51
  • 0

Sissy Rules Reads like a proper job description

(Found this on the internet... #65 seems especially made for me) Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows...

1 year ago
  • 0
  • 35
  • 0

Sissy Rules

Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows big fake titsRule#14: A sissy is a pro cock suckerRule#15: One is...

2 years ago
  • 0
  • 38
  • 0

Sissy Julian Chapter I Beginnings

Here we go again. Some boys simply are sissies. This is the story of one of them. It is not a story of discovery, although there is much of that, but rather a tale of a lovely boy's trip to self-realization, albeit a tad 'forced.' If lots of frilly sissy boy and girl outfits, super swishy behavior and a little sex, not to mention dominant women, are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fictional fantasy work. No references...

1 year ago
  • 0
  • 30
  • 0

Sissy Crissi Chapter 3 Leroys Turn

Chapter 3 - Leroy's Turn But Leroy had been left out for too long. Eager for his turn, I had no sooner finished pleasuring my Mistress when I felt his hands reach up under my skirt and start pawing my panty covered ass. Standing behind me, Leroy bent down and lightly held the back of my thighs in the palms of his large hands. He slowly slid his caress upward, off my stockings, across my garter straps, up to where he cupped my round bottom in his palms. He then placed his fingers...

4 years ago
  • 0
  • 41
  • 0

The Chronicles Of Sonali 8211 Part 2 Horny For Her Son

Vineeta took a large sip of the champagne and started her narrative. Vineeta’s Story It was morning when I bathed my son and gave him a handjob. Now as I was preparing his favorite chicken biryani. I started replaying the whole scene in my mind. The only thing that was recurrently playing was his hard, erect penis and the thick ropes of sperm that hit the bathroom wall. Any trace of guilt had evaporated from my mind and I was feeling horny. But I decided I won’t make any first move and let...

Incest
3 years ago
  • 0
  • 39
  • 0

Sissy discovers Part 5

Part 5 of the story about Sissy and her sexual awakening ****************Brad did not hesitate when invited to go over to Lisa’s. Sissy was not surprised. What young male would not want to hangout with a girl who flaunted her nude body in front of him only hours before. They decided to take the pontoon boat over as it is ten minutes by boat and almost 40 minutes by car. Evening cruses was a family specialty and Brad was good at handling the boat. As they pulled up to Lisa’s family dock Sissy...

4 years ago
  • 0
  • 27
  • 0

Sissy gracie Life begins anew

Sissy gracie, Life begins anew Chapter 2 As i stood to dress.. the first guy asked me.."So cunt.. you are wearing sissy clothes underneath and all lockedup. Do you have other clothes .. other sissy clothes?" 'ohh Yes Sir' i replied... "Good .. tomorrow.. bring the key.. and wear more.. i want to see you all sissified...... no pants.. just sissy clothes.. prissy dress.. stocking.. high heels.. make up... make your tits look big...... do it up...... and I will hold your key...

4 years ago
  • 0
  • 40
  • 0

Sissy thoughts 2 Questions From Sissies

1. I am about to have my first experience as a sissy with a Man! How can I make it more special for us both?A: How wonderful! You are at the very start of your new sissy life. It will of course be special and memorable, but to deepen the reprogramming of your still-forming sissy mind, try dressing as a sissy schoolgurl. Not only will it drive your Man wild with lust, but the symbolism of your costume, and the reality of the loss of your virginity will combine to kickstart stronger, more...

3 years ago
  • 0
  • 24
  • 0

Simpsons Father and Son Camp Bonding

As Bart loaded his bag, in the car, he couldn’t help but complain again. He didn’t want to be up so early, didn’t want to go camping and certainly didn’t want to go there alone with his father for a whole day and night. He couldn’t blame Homer however. It wasn’t his idea after all, it was his mom’s. “Please Bart, do it for me,” she had said with her pleading eyes, the ones which no son could resist but agree to. Homer had complained as well and Marge had dealt with him...

2 years ago
  • 0
  • 30
  • 0

Sissy Farm Chapter Twelve

Sissy Farm - Chapter Twelve By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's brother.) James: AKA....

4 years ago
  • 0
  • 24
  • 0

Sissy Sally

CAUTION: This is a forced fem story. If this is not your thing, please move on. All rights reserved. Sissy Sally Sam Smith fretted anxiously at the kitchen table while he waited for his mother to return from the district attorney's office. How could he have been so stupid? Breaking into the new neighbor's house had been a disastrous idea from the start. Ms. Johnson was an attractive, impeccably dressed older widow who had moved into the house-...

2 years ago
  • 0
  • 28
  • 0

Sissy discovers Part 4

the continuing original story of a young girl finding herself****************************Breakfast was filled with the usual mumbles of ‘good morning” and banging of pots, sizzling bacon and gurgle of juice being poured into tumblers. Sissy and Brad avoided looks at each other at first, and then Sissy sat down across from him at the table and patted him on the head saying, “what’s the matter grumpy?” in an exaggerated baby voice. “Nothin’ - hand me that fruit will ya?” He replied and gave...

2 years ago
  • 0
  • 35
  • 0

Sissy School Part 2

SISSY SCHOOL - PART 2 By Missy Crystal I followed Mistress Mary back to her office. She left me standing in the middle of the room and sat down behind her desk. After ignoring me for a few minutes, she looked up and said, "I told you that you would be severely punished for disobedience." Crap, I thought to myself. I already have six strokes of her leather paddle coming. What did I do wrong? My face dropped. She smiled, "but I can also reward, when I am pleased with your behavior. You...

1 year ago
  • 0
  • 28
  • 0

Sissy Cruise 3

"We are going on a Caribbean cruise, in two weeks time......." stated my wife Penny. "Oh......Okay," I queried. "With Samantha and Tim," she finished. "Oh really." Samantha is a new friend in my wife's life. They have known each other for a couple of months, but they are already quite close and always scheming together. My relationship is mixed. It seems that the only time she talks to me is to point out my faults which is somewhat annoying. However she is very domineering...

Porn Trends