my sissy encounter turns into a bondage fuck-fest

by BillyBoy

27 Feb 2023 4251 readers Score 8.6 (23 votes) PDF Mobi ePub Txt


Greg was a bit of a pussy. Not much of a 'Dom' type. He was posting for a meet-up with another submissive sort of gay man. I wasn't interested in him at first. I was hoping for the old "I'm in her underwear and he catches me" scenario. I've always thought being caught, humiliated and dominated would be the best way for me to start exploring my bi/gay side. A side that I've been repressing for years. I'm not sure I can willingly just walk into a gay encounter. I need a push.

Greg was horny and told me he would give having me wear his sisters party dress and tying me up a try. He said having a guy dress like that and being bound had always been a turn on for him. He wanted to get sucked off, and I wanted to try sucking a cock for the first time. He was a shy, simple sort of guy. He seemed nice, and safe. We planned to meet at his apartment. 

Greg was a normal looking man. In his mid 30's, average height, average weight, average looking. His apartment was nice, clean and well kept. He leaned in and kissed me right on the lips, right away. I backed off a bit. He looked at me like "This is what we are here for, isn't it?'

He's holding a long fluffy pink prom dress and a set of police style handcuffs in his hands. " You're going to dress up, put these on, then suck my cock, bitch!"

Music to my ears. 

With the dress was a nice bit of lingerie. I didn't think at the time about a normal bi guy having so much fancy ladies' underwear on hand. I quickly pulled on the white lace bra, garter belt, stockings and lace thong back panties. Everything was a pretty good fit. The prom dress fit me pretty well too. I didn't think about all of that until later either. 

"How should I put on the handcuffs?"

"Behind your back, you stupid cunt." 

More music. Maybe this guy has some potential after all. I'm really not experienced at this at all. But I've dreamed of it forever. Caught in a prom dress. Handcuffed like a kidnaped schoolgirl. Forced to suck a big cock like a whore. I came here. I told him what I wanted. He is delivering. Here we go!

He steps into the bedroom holding two beers. He is looking me up and down. He seems different. His pants are gone, His cock is hanging down from under his T shirt. Half hard and looking tasty. This might be fun. He says in a stern, dominant voice, "You look like my stupid, drunk prom date. Lock those cuffs on and lets' get this party started." 

Suddenly I realize I'm alone, up in a strange man's bedroom, with only one way out. And he is blocking the door. I see myself in the bedroom mirror. The dress makes me look ridiculous. I'm not a girl. This isn't a date. He could do anything to me. I'm hesitating. The cuffs aren't locked yet. What the fuck should I do?

He perks up as we both hear the click of the clasps snapping loudly. It's a final and disturbing sound. I've pushed the handcuffs together, locking then. I'm all in now. What have I done? He is smiling. I'm feeling humiliated, embarrassed and horny, all at the same time. Is this a nightmare about to begin, or a dream come true? I can't take my eyes off the glistening head of his erect penis. I'm so fucking nervous. The cuffs are tight. I squeezed then too hard. I'm sweating with fear and anticipation. But for some crazy reason I think to myself, "This is perfect!"

The beers are set on the dresser top. Grags shirt comes off. I feel myself falling back, away from him. But he is on me, and I can't stop him. He has me wrapped in his tight grasp. He forces his tongue into my mouth. I've only kissed two other guys. He isn't the submissive guy I was expecting. He has a handful of my hair. He is pushing his tongue in deeper. His other hand is exploring my body draped in the satin dress. I can feel his hard cock poking me. It's happening so fast. I catch my breath and try to pull back. I quickly realize having my hands cuffed behind me makes me very helpless. He looks me in the eyes and says, "You're ours now, bitch."

That doesn't sink in until I'm already on my knees sucking him. My dress is half off. The lingerie is pulled aside and twisted around from him groping and molesting me. My knees hit the floor with a thud when he roughly pushed me there. He is being rude and demanding. I suppose I asked for that. I should take what I asked for? "Suck it you tramp! Suck harder! Use that slutty mouth for what it was made for. Suck me, bitch!"

I'm doing my best. I'm not sure what to do. I try. I suck. But his orders and demands are making it hard to concentrate. Plus evert 3rd or 4th thrust he pulls my head in and slides his cock back into my throat. So, I'm choking and gagging like a cock sucking rookie. And what he said. "You are 'ours'? "

Finally, we get into a rhythm, and he comes. I didn't know there would be so much. I choke and cough and drool and even swallow some of it. He laughs. 

He is breathing easier now. So am I. I figure I'll be uncuffed and we can finish the beers and have a laugh over how shitty I am at it. My mistake. Instead, he straightens up my bra and pulls the dress back up over my shoulders. He has a large, soft red rubber ball in his hand. I can't figure out what it could be for. It's much too big for my mouth. It's as big as a very large orange. He takes my head by a handful of hair, looks into my eyes, and says, "You were a good cock sucking bitch. Now open up!" He roughly pulls my head back. I gasp and complain from my hair and head being jerked back so hard. 

My lips and mouth are so drenched in cum, the ball slips right in. Well, most of it anyway. It's huge. My mouth can't open any more. But the ball forces it open even further. He is pushing the ball back into my mouth as he is pulling my head forward. I hear myself make a very loud "Ahhhh!'. Then a muffled "Mummphh!" Finally, after more stuffing and pushing, it's nearly all the way in. 

A wide black nylon strap running through the middle of the ball is pulled back around and behind my head. A buckle tightens. Then more. The ball is forced even further in. Greg is pulling and stretching the strap much too tight. My cheeks puff out. But the strap squeezes them back. My mouth is spread wide open, and stuffed full. My eyes are wide open too. I can't believe the ball went in. Cum is squirting out of my mouth, drooling over my chin. Some is dripping down and staining the front of my pretty pink dress. 

When he is satisfied the ball in in place, and I am completely subdued, I am lifted onto the bed, sitting up. "Don't fucking move! Or you won't like what happens." I obey.

Part 2, coming soon..

by BillyBoy

Email: [email protected]

Copyright 2024