Sissy Blog  POST

His First Sissy Bondage story

September 16, 2018

Get a sissy training trail here: Sissy training

 

I have been a very big fan of bondage especially sissy bondage. I like putting a sissy in a predicament but still trying to look sexy and slutty. I may not look threatening, with my soft features and always a sincere smile on my lips. People usually mistake me as soft. But after a session of sissy bondage with me, their opinion of me takes a 180 degree turn.

 

A young CEO new to the lifestyle viewed my profile and asked if I was truly a domme. He said I did not quite look the part of a pro-domme. He was looking for something new and harsh. But nothing brutal that would leave visible marks. He said he had doubts with me since I look nice and sweet to be a domme. But he still agreed to meet with me.

 

We had the usual dinner meet up, talking face to face, gauging each other, knowing the limits, negotiating. One thing he has been fantasizing about is being a sissy. Talking to him face to face gave me an idea of his personality and inspiration for our first session - sissy bondage.

 

After finishing our meal, I gave him his first task. I told him to put snicks on the sole if his foot, one snick per hour on the dot, not before the hour and surely not after. If he's late he has to tell me. His lates will be the number of clothespins I will put on him as punishment. And he has to do this for the next two days until we have our first session. 

 

He looked nervous sitting patiently on my living room couch. I hid all my wonderful toys so as not to scare him. I kept it to a minimum so he won't get discouraged and to build trust. On the coffee table in front of him I laid a long piece of string, a ball gag and several clothespins. He was surprised when I walked in the room in full domme outfit with a riding crop in hand. I assured him I won't use the crop on his body. Even if it did touch his body, "hold out your hand." He raised his open hand and I hit his palm with the crop. "See, it doesn't hurt that much." And he looked at his open hand, waiting for the pain.

 

I pointed to the corset and thongs laid at the back of the couch and told him to wear them. He stood up and shyly took off his clothes in front of me as I watch him. He was looking at my reaction to his body. I was just standing there, arms crossed in front of my chest still watching him. I started tapping my foot to show my impatience as he fumbled with the thong panties. Next he studied the corset, figuring out how to wear it. I grabbed it from his hand and motioned for him to come closer. We stood inches from each other, I could feel his breath as I put my arms around his waist to wrap the corset around him. He stood there motionless, watching my every move. I could feel his amused smile as I fastened the hooks in front. Then I grabbed the side of his waist to turn him and caught a glimpse of his shy smile. I remained stoic as I tightened the laces at the back of the corset. I could hear him holding his breath as the bodice got tighter. 

 

I walked to the table and picked up the long string. Then I slowly walked towards him, looking seductively into his eyes. He was holding my gaze, lips slightly apart in anticipation. I stood inches from him, looking up to his eyes as I rested my hands on his thighs. His eyes slightly widen as my nails scraped his skin slowly working their way to the middle. My hands stopped and I glanced down to see the head of his cock peeking above the waist of the panties. I held it with one hand and looked up at him again. I slowly lowered myself to face his hard on and he was just holding his breath. I yanked down the panties to free his cock. Slowly I tied the string around the base of the head then gave it a light kiss. I could feel his eyes on me as I did this and he gave out a long breath. I stood up and let the string dangle from his cock. He was slightly confused and yet aroused by this. I gently placed my hands on both his hands and slowly raised them above his head. He was still wondering what I was up to. I slowly run my hands down his torso as I walk to his back, my hands not leaving his body. I work my way up again to his arms and slowly pulled them to the back of his neck. Next I squatted behind him and reached between his thighs. I grabbed his cock and pulled the dangling string back from under him till it reached his hands. He slouched a bit which made me smile. Then I tied his hands with the string connecting to his pulled back cock.

 

"So how many times were you late?" 

 

He tried to raise his foot to show me, "twenty Mistress." as I walked back to the table to get a few clothespins.

 

"I see." I proceeded to clipping the clothespins around his crotch, 5 on each side, then another 5 on each butt cheek.

 

I stood back to inspect my work, "I do enjoy sissy bondage!" Laughing at him as he winced in pain and he wanted to put his arms down. He was whining a bit so I put the ball gag in his mouth and fastened it behind his head.

 

"This is your punishment for not doing my task on time!" I gripped my crop ready to strike. I can see his eyes widened in horror. "Stand still bitch! You don't want me to hit you with this!" And he did as he's told. I raised my crop and swoosh! His muffled cry was audible as I hit two clothespins off from his crotch. He shut his eyes close in pain.

 

"The longer I wait the longer the agony for you." Then he opened his eyes again to look at me and braised himself. Swoosh! His muffled cry was louder as I hit 3 clothespins off this time. I walked up to him and gave him a kiss on the cheek.

 

"There. There. Fifteen more to go."

 

I noticed his boner did not diminish even with him crying in pain. I guess my sissy bondage works for him!

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