tagTransgender & CrossdressersKeeping My Sissy Secret

Keeping My Sissy Secret


YES! She really won't be home! I thought to myself as I cycled towards my house. My mother's car was missing from the driveway, meaning her plans for visiting a distant aunt hadn't been cancelled after all. Her wardrobe would be all mine for the entire weekend and I couldn't wait to try on her clothes. Aside from everyday clothes fit for a single mom, there were several items for special occasions such as going out for drinks. And even better, during a previous raid I had found a hidden box with lingerie.

Fantasizing about wearing your mother's clothes might seem strange or even perverse, but not to me. I have secretly been a crossdresser since I turned 19. Things didn't stop there, as I found about sissies when I was looking for crossdresser porn. I now own several toys and some lingerie, sometimes cam and occasionally try to meet a man for sex. Unfortunately, that last part isn't really working out so far, with the men often being total weirdo's and when they aren't I get cold feet. I know, pretty terrible.

"Hey Peter, you seem happy. Anything good happen?" my neighbor asked, noticing the large grin on my face. I hadn't noticed him while fantasizing.

Jacob, a man in his late 40's or early 50's was one of our neighbors and currently smoking a cigarette in his front garden. His large belly hung over his trackpants, while his shirt had some stains on it. Because of his size and friendly demeanor my mom had started to jokingly refer to him as the local Buddha, supposedly sharing ancient wisdom while going on one of his many smoke breaks. To me he was just an ok dude as I didn't have much interaction with him.

"Yeah, I got the house to myself this weekend. I already invited the supermodels."

Jacob laughed at that, blowing his smoke in my direction causing me to cough.

"Hey, watch it!" I managed to get out between coughs. "You are killing me here. Just when I have the house to myself!" I jokingly added, laughing with him after the smoke dissipates.

"Well, you weren't gonna get laid anyway if you are acting like a sissy. Just a bit of smoke never hurt anybody." He laughs even louder at his own retort, although I stopped smiling. Just like how some people cannot use the word 'daddy' anymore, the word 'sissy' in everyday language is ruined for me. Still, I do my best to force a smile.

"Oh, cheer up, just a harmless joke." He grunts, taking another drag from his cigarette. "Now, I won't keep you any longer. Go and call those lovely ladies of yours. I'll see if I can contact mine." Waving dismissively, he walks back into the house.

"Sage wisdom my ass. Bad jokes, that is what he got." I muttered while putting away my bike.

I run to my room to boot up my computer. Not waiting for it to finish I go and check on the bounty in my mother's closet. There is just so much choice! I pick out several items I really want to try, carefully remembering where I took them from. The picked clothes don't make a coherent outfit, having been solely chosen because of sexiness and how the fabric might feel on my skin. After all, the entire weekend could be used for experimentation, so I can always switch.

I put the bundle of clothes on my bed before logging in. Once again, many people were online in my town. In the end I decide to just put the filter on preference instead of distance. I probably would end up just camming after all, so why limit myself? While accepting a few chats and sending out 'Hello' a few times to potential doms I stripped quickly.

Looking at the large mirror on my door I grabbed a pair of stockings and started to put them on, watching myself while doing so. The soft feeling on my skin was like heaven causing me to almost purr like a cat. They just felt so nice and snug on my legs! The suspenders were next, although they required some fiddling to put on correctly. Even though dressing up had become a regular thing, putting the items away gently was still something I refused to do. And every time it would bite me in the ass, having to spend several minutes untangling everything. Next was a party dress that showed a lot of skin and was quite short. Thankfully it covered the breasts rather well, meaning I could use it with my homemade breasts, made from socks with rice.

Only then I noticed I hadn't picked out a bra. Damm, I needed one to hold up my tits. I wondered why I hadn't taken one before while I walked back to my mother's closet and started searching.

Shit... There were none in the wardrobe... Where could they be? A quick search and a tipped laundry basket later I suddenly realized where they might have gone. Glancing out the window into the backyard my fears were confirmed as all the bras my mother hadn't taken with her were hanging out to dry after being washed. There probably was a list of chores somewhere, but in my rush to become my slutty true self I hadn't noticed.

I hesitated for a moment. Could I just walk out the door to quickly grab them? Would anyone see? I couldn't risk it, but didn't want to redo everything later... In the end I grabbed my large winter coat that covered most of my stocking clad legs and put on some shoes. Hurrying outside I snatched the bras, hurried back and slammed the door shut behind me.

I let out a slow breath as I slumped down against the door. The chances that somebody would have seen my stockings was very slim but only after I remembered the treasure in my hands I calmed down again. After a quick inspection of the options I choose a black classy bra and went to my room to finish up.


In my absence several messages had popped up. I scanned them for any potential cam session or at the very least a naughty conversation. I had learned to ignore messages that only said 'hi' as they would just lead nowhere most of the time. As I did that I put the finishing touches on my outfit.

There, I now looked like the sexy femboy I knew I was on the inside: surprisingly wide hips for a man, a skinny frame, completely shaven smooth and my self-made breasts. The illusion of me being a biological woman was only broken by my little pecker forming a cute but tiny bulge in my dress. That and my face. Because while my face was very feminine looking and would certainly be passable if I was to put in the effort and put up some make up, I had opted to just wear a black hood made from some stretchy material. This saved me time and made sure there was no way I could be recognized.

With a few taps on the keyboard the cam turned on, my body immediately appearing on screen. Being a bit vain (or insecure according to my mom) I always did a check on the angle before actually streaming myself. Thankfully no adjustments were needed aside from turning on an extra lamp to highlight my pale skin.

All ready, the stream began. allowing everybody to see me. My starting position was always lying on my side, with my clothing covering as much as they were able to. What makes lingerie so hot is that it teases, instead of outright showing the goods. The added bonus from this slow approach was that I could edge for hours if nobody interesting came for a chat. The view number was on 17 people currently watching, so I just kept checking my chats for a few minutes while occasionally groping my bulge.

Out of nowhere something hit my window with a loud crack. Snapping my head towards the noise I kept completely still and tried to hear what was going on outside.

Silence. Just silence.

I didn't dare to open the curtains while dressed so all I could do was sit there and something to happen. With my sound turned off and the hood covering my facial expressions nobody watching seemed to notice there was anything happening. After a few more minutes I shrugged and went back to reading my messages. Must have been nothing...

Chat was still quiet, so I got up to speed quickly. Except the last message from somebody I didn't know made me freeze again.

It simply read: "Peter?"

I stared at it for a few seconds before quickly stopping the stream and unplugging the cam, just to be sure. I closed all the porn and other messages, not even saying goodbye or explaining why I was leaving.

Just the message stating my name was still open. I hugged my legs and just stared at it, hoping another message would come and somehow explain what was going on.


Slowly I started typing a response.


More silence. Until suddenly "anonymous user is typing..." popped up in the screen.

"You look sexy Peter."

My heart was pounding fast and my breathing a bit ragged.

"I think you got the wrong person."

"Something hit your window just now didn't it?"

The response followed immediately, dashing the little hope I had that it was just a misunderstanding.

"I know it is you. Does your mother know?"


"No" followed by "What do you want?"

"What your profile says, a sissy."

"Who are you?" I tried, hoping to get some answers.

"Your new daddy"

"What do you want?"

"What does my daddy want?"

I sighed. This person was ruining my life and now trying to get me to jump through hoops for him. If this was a regular roleplay I wouldn't even be impressed with his dirty talk.

"What does my daddy want?"

"To have you stand by and make him cum whenever he wants."

"You could have just watched the stream. WHAT DO YOU WANT?"

My patience was wearing thin. Fear made room for anger. This shit had to stop.

"I don't want to watch. I want your holes around my cock."

This guy wanted me to meet him? Was it somebody I knew personally? For some reason I had assumed it was some kind of hacker or stalker that found out my personal details.

"Come to my house, right now. Don't change, just wear your coat again. I see you in 5 minutes, tops. Don't make me wait, I want my supermodel for this weekend."

Only then it clicked in my head. The mystery man was Jacob... Fucking Buddha...

Like a zombie I got up from my seat and went to grab my coat. My mind seemed to have been fried from the revelation that not only was I found out, but my nearly obese neighbor was blackmailing me. That was just too much to take in within only 5 minutes.

Standing in front the door I almost couldn't be bothered to check if my coat was covering most of my stocking clad legs but decided that more exposure certainly wouldn't be the answer. With the hood in my pocket and lead in my shoes I walked to the neighboring house.

The door was already slightly open, so I just stepped in and closed it behind me. The hallways was surprisingly dark with the door shut and stank of cigarettes. The smell was horrid, but I had to push on and walked on. The doors in the hallway were all shut, except for one. There was light there, but I couldn't tell if it was one of those very old lamps that was very yellow instead of white or that the walls were just that dirty. Jacob probably had to be there.

The first thing I noticed was the massive smoke cloud hanging in the room, the result of indoor smoking and a refusal to open a window every now and then. The second thing I noticed was the large frame of Jacob sitting on a chair in front of a desk, with a computer screen showing the same site I had been frequenting for a while now. He wasn't wearing his shirt anymore, showing of his chest hair and the large belly underneath.

His eyes seemed to be glued the screen, or he had simply chosen not to acknowledge my arrival. Between his lips dangled another one cigarette, and I could see an ashtray filled to the brim on the desk in front of him.

That explains the stench at least.

In no hurry to start this confrontation I let my eyes wander over the room. It was clean, I guess. No stacks of newspapers or piles of dirty clothes. Aside from the desk, chair and a closed wardrobe there was a bed and nothing else. The bed had black, slightly shiny sheets on them.

Silk? I wondered. Not something I would associate with a slob, but maybe my dislike for tobacco had clouded my judgement.

"You have arrived. About damn time." Jacob suddenly spoke, turning his chair towards me as he put out the remains of his cigarette.

I was completely frozen, staring with wide open eyes at his crotch. When I came in I hadn't noticed, but his cock and balls were hanging out of his trackpants. Jacob was big. It must have been slightly shorter than my dildo at home, but it was much, much thicker. He was uncut, the head was poking out of the skin slightly. Does this mean he is half hard or soft? Underneath his member his sack was saggy and I could see both balls individually. My sack always was more like a tight pouch, even when it was very warm.

Despite my horrid situation my sissy fetish was getting the best of me, causing me to carefully examine his big dick. Realizing this, I bit my tongue. This is fucked up. What is wrong with me?

"Are you done staring?" Jacob spoke. A wide grin was plastered to his face.

Thankfully I still had the decency to turn red and stare down.

"How did you know?" I managed to get out, still not making eye contact.

"I have watched you once before, but I never realized it was you. Not until your weird reaction when I said sissy."

"That was it?"

"Well, that and the fact that I saw you in the backyard looting just the bras from the washing line."

Oh, fuck. I had been so busy with not being seen in women's clothing that I hadn't thought about also taking other things to mask my real intent.

"Then I still wasn't sure, so I threw something against your window while checking your stream. And hey, there was a reaction."

Now I was shaking from anxiety. How had I been so careless?

"Peter... My sissy... It doesn't matter. I have read your profile. I know that I fit your preferences, kind of. I won't out you. All you have to do is give in to you desires and we both walk away happy here."

Jacob used his feet to move his chair forward, coming slowly closer to me. His big meaty hands unzipped my coat, revealing my dirty secret once again.

"You look better than on your stream. Where is your hood?

Now that he was so close I had to look to the side to avoid his gaze. I patted the pocket it was in, not having the will to take it out myself or answer him. He took it out and put it on his naked lap before helping me out of the coat and throwing it in the corner of the room. His eyes wondered over my body, causing me to cross my arms in a bad attempt to shield my body from his scrutiny.

"Sexy little thing, we are going to have so much fun... Now get on your knees for me, sweetheart."

His hands moved up to my shoulders and gently started pushing down. I debated fighting it, but I let him in the end. His large hands felt rough on my bare shoulders. I didn't know what kind of job Jacob had, but it must have been something physical.

"Now take of your shoes for me."

I complied, still not saying a word. Meanwhile he got the hood and put it on my head. Checking if I could see out of the eye holes and if my mouth was accessible he forced me to look forward, straight at his crotch. His penis was becoming erect, like a snake slowly waking up from a nap.

"You like what you see? Cause I know I like what I see. And it is making me so very hard... Why don't you help it grow a bit more?"

My head was being dragged towards his large dick, Jacob's iron grip not giving me any choice in the matter. Just before my nose was about to make contact however, he forced me lower but looking upwards.

The first thing to touch was his tip with my forehead, before the entire length came to rest on my face. Up close it was even thicker, making it almost impossible to still see his grinning face looming above me. I released a breath I didn't know I had been holding in. Even with the hood on I could feel the immense heat from his cock on my face.

This should feel bad, but it felt so good.

I closed my eyes and sucked in his scent. So masculine... Maybe just this once...

Jacob moved a bit forward on his chair and I could feel the weight of his balls on my chin now.

"It is funny how you look like a precious princess. I am pretty sure your profile said you were a massive slut and liked being treated like one. Time to get to work!"

His hands grabbed the sides of my head and started moving me back and forth. The big slab of meat was being dragged over my face and I could feel a drop of something wet land on my forehead near the tip. He wasn't rubbing his cock on my face, but rubbing my face on his cock like a masturbation tool.

I could feel my clitty getting hard as I was slowly getting drawn in, letting go of my inhibitions and fears. This was what I had been yearning for when I started all of this and now it was finally happening!

Carefully I stuck out my tongue, trying to get a taste of his dong. It tasted a bit salty, but I couldn't tell if it was sweat or something else. Clearly he liked this, as he grunted and started moving me faster.

"That is right bitch, give that popsicle a good spit shine! Make daddy happy!"

His movements were getting rougher and his 'strokes' broader. His balls hit my chin each time and I moved a hand towards my clitty to get some relief. Just then, he decided he wanted more. Moving my head back even further until just the helmet was laying on my lips he tilted my head straight again and pushed forward. I wasn't prepared and could offer no resistance even if I wanted to the swollen fat cock invading my mouth. He grunted loudly as he drove as deep as he could, which wasn't very far. Cheeks bulging, I gagged and sputtered, but he kept pushing.

"Come on! Useless sissy! Do I need to do everything myself?"

I had sucked on dildoes before, even tried my gag reflex. But there is a clear difference between wanting to act slutty on cam and a large man trying to get his massive prick off in your throat.

Jacob got out of his chair, hunched to still get the angle and started trusting his hips frantically. His babymaker was too fat to go deeper, but that didn't stop him from trying, cursing and grunting all the while. Tears were filling my eyes as my face was being violated. Saliva was streaming down my chin and each time his sack would slap against it, all the spit would splatter around. I had stopped masturbating, but my cock was still throbbing underneath my dress.

Suddenly Jacob's grunting got louder. With a roar he pressed my face as deep into his crotch as possible, hunching even more forward. My throat stretched wide and his massive donger slipped inside, burrowing down into my gullet. My head was almost hidden by his fat belly hanging over it.

Then I felt it. His balls against my chin were jumping up and down slightly.

Oh my god, he is cumming!

His throbbing member started spewing baby batter. He was to deep for me to taste it, but I could feel it sliding down towards my stomach. Jacob hadn't stopped roaring, sometimes even shaking my head as if to milk his cock faster. There seemed to be no end to his flood of cum, before he suddenly fell quiet again. Still holding my head, I could feel the torrent go down to a trickle until it finally stopped.

A few moments passed. Then Jacob just started laughing. Slowly he pulled my face out of his crotch, retreating his cock from my gullet and mouth. He let himself fall in his chair wile I wobbled on my knees and started coughing violently, trying to clear my throat of all the saliva.

My fat neighbor had just blackmailed me, facefucked me, come down my throat and was now laughing. What the hell is going on?

"Oh babe, we are going to have so much fun, you and I." Jacob managed to get out between fits. "You just are the perfect slut, aren't you? Now daddy is going to take a leak and then we are going to see how much anal training this bad sissy has done..."

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byVrijeVogel© 4 comments/ 34933 views/ 38 favorites

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