Secret Sissy

by BillyBoy

10 Dec 2021 3581 readers Score 7.4 (9 votes) PDF Mobi ePub Txt


Innocent and horny

I've heard most boys and men try on their mommy's or sister's or some girl's underwear at some point in their lives. Just for fun, you know? For most, it ends there. But for many, like me, it never stops. 

After several girlfriends and 3 wives, I've decided I'm just not cut out to be a regular normal guy. I spend way too much time and energy playing in ladies' underwear and clothes. I love it! I can't stop. I'm addicted. What the fuck?

After surfing gay and sissy websites it's pretty clear that gay men don't prefer a sissy in a dress. And straight guys don't really like them either. So that doesn't leave very many possibilities.

Rather than chase an impossible dream of a real man wanting me, I resign myself to dressing up like a woman, looking at myself in the mirror, and jerking off in the privacy of my own home. It's nice to share my thoughts and some of my best pictures on a few of the sissy websites and chat with like-minded, confused, and horny sissys.

I take the plunge

'Master Savage' likes my pictures. He frequents the websites too. He lives in Seattle. He says he has several sissy girlfriends. He says he is always looking for new 'victims'. He is in his 50's probably. tall and skinny. Horny all the time. He is always wearing a black leather vest and chaps. He has a lot of his cock pictures posted. He is hairy. His cock is long and throbbing. The veins on his cock are thick, blue, and purple. They seem to be begging to have a sissy mouth on them. I go back and look at all his pictures a lot. 

He tells me he has helped several girls come out. He says he likes showing them exactly what they really are. He says he will make me realize I am only a submissive tool for a man to use as he pleases. Like a hammer or a wrench. The man can use those for many tasks. Any task he chooses. And the tool can only do as the man instructs. I would be that simple tool for the man to use as he likes. I would be there for him, at his beckoning. He would take me through the process of becoming a willing slut. A whore for him. He will teach me. He will use me. And then he will throw me away until he desires me again.

I was so fucking hard as we chatted. Seattle is like 4 hours away. He says he usually doesn't keep his 'victims' overnight. There is a hotel nearby. I have to schedule an APPOINTMENT. I'll show up and he will decide if he is willing to waste his time with me. Otherwise, I'll have to drive right back. Disappointed. Humiliated. Unfulfilled. And still really horny.

The hotel was nice. A Holiday Inn. I dressed in my best black lace lingerie and a short, red party dress. I'm not all that fem. But he knows that. He said it's all in the attitude. His house wasn't as grand as I expected. I was hoping for something spectacular to be trained and violated in. I parked beside the house and put on the dog collar and ball gag as he had instructed. I had to buy the collar, cuffs, and ball gag myself. I was ok with it all until I saw the ball gag. The one he picked out for me to purchase had the largest red rubber ball they sold there. It took me several tries to get my mouth around it. It hurt my jaw immediately. I was already wearing the cuffs, ankles, and wrists. Pink leather BDSM cuffs. I hoped he would approve.

My room

A younger man opened the door. He had been instructed to bring me in and show me to my room.

"Master will be here shortly. He asked me to welcome you. " 

 He hooked a chain leash to my collar, used a paddle lock to secure my arms behind my back by the wrist cuffs, and led me through the house. It was plain, boring, and kind of scary. We silently went through the back of the house, then down a concrete stairwell. Not really too nice. It was dark and cold. I was getting really nervous. I pulled at the wrist cuffs. They weren't coming loose. I was all in now. I was fucked. 

At the bottom of the stairs and through a narrow hall we arrived at our destination. A heavy, dark wood door. He pushed it open and turned on a light. There was a small bed with no blankets or sheets on it. Just an old box spring and mattress. He pushed me over to the wall. Backing me against it. There was a long wood board attached to the wall, running up and down. It was securely screwed to the wall. Every 6 inches or so was an eye bolt. A heavy steel bolt screwed into the board with an eyelet showing. It is there to chain something to. Like my collar. He used another paddle lock, snapping it closed, holding my neck back to the board. I tried to ask for mercy. I suppose I thought I needed some right now. But you can't speak with a ball the size of a tennis ball strapped into your mouth. 

The young man looked me up and down. He used his phone to take some pictures of me. Chained up in some stranger's basement. Fuck! After several different angles of me, closeups of my gagged face, and panty-clad ass, he was done. He reached up, holding me by my chin, looking me seriously in the eyes. "Master is going to like you just fine. He may even tell you so. After he fucks your pathetic brains out. Bitch!"

He gave my cheek a little slap. And he was gone.

As I struggle with the huge ball in my mouth and the tight bondage cuffs, I look around my stark surroundings. The first thing I notice is a large video camera on a tripod just a few feet in front of me. It's pointed right at me. A small red light is on. I decide I can't do anything about it and continue to look around. There is the bed, a small nightstand, and a dresser. On the dresser are several bottles of colored liquid. Sex lubes and the sort I assume. Next to the dresser is a small, open closet. Inside are hanging an assortment of black leather and vinyl garments, leather belts, and chains with metal handcuffs. The rustic and minimal bed frame is all metal. There are a few handcuffs hanging from different points on the head and footboard. It's cold in here. But I'm sweating. 

by BillyBoy

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