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Becoming a true sissy (fantasy)
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Here is a fantasy I have, please bear with me as it will be quite long but hopefully worth it.

I was talking to this guy we will call him sir and we agreed to meet up at a hotel. So I got there early made sure I was all prepped and ready for our day, as I got dressed the nerves were building, so I decided to have a shot to calm down a bit. I got dressed up in my little secretary costume, matching bra and thong, garter belt and stocking. I did my make up and wig and just waited staring at my phone. I got a message from him Will be there in 5. Be ready. I jumped up the nervous energy building, I replied back Told him room number and said where the key was. I sat on the bed and waited, the door opened and in he walked, he was taller and more built then my small frame I walked up to him and greeted him. He looked at me up and down asking me to turn around showing off, he lifted my skirt Nice sissy he said He placed his hand on my face and I went in for a kiss he stuck out his arm looking into my eyes not yet sissy. He pushed me against the holding me there, I felt his hand up my skirt as he grabbed my clit, he was looking me in the eyes Let's get this weak sissy cum out of you He started to play with me as I moaned and shook it didn't take long for me to cum, he grabbed a glass and put my clit in it, as I started to cum in the glass. He placed the glass on the counter and grabbed my cage and locked me up, He held the key in my face I'll release you once I'm done. He walked off to the bathroom to shower he called out for me to prepare him a drink. There I was dressed for him caged up drink ready for him waiting. I was feeling so subby waiting caged. The door opened and out he came just in a towel, I offered him a seat and gave him the drink, I sat down on his lap Where your drink he asked? I got up and started to pour one. Oh no sissy he said, yours is your sissy juice, so I grabbed the glass with my juice and sat back on his lap, cheers and he started drinking while I had mine, I felt so hot and horny drinking my juice, Good girl he said, here's your reward on your knees close your eyes. I was excited here I'll get his cock I hopped down and got ready, then I felt something around my neck, it was a collar and lead. I looked up at him he had a big smile on his face staring down at me, Go for it he said I opened up his towel to unveil his monster, it swung out and smacked my head it was big and thick a beautiful cock, I held it in my hand holy crap he wasn't even fully hard, I started to lick up his shaft and onto the head, I could feel it swelling in my hands, I opened wide and started to suck him, his cock still swelling and growing in my mouth, I started slow and worked up a pace trying my best to deepthroat him. He started to moan he was loving it. He stopped me after a bit And picked me up and placed me on the bed, he put me on my hands and knees ass up, He started to tease me, grabbing and spanking my ass, he slid my thong to the side and started to rub my bussy, I reached around and grabbed his hand and started to suck his finger lubing it up, Naughty girl he chuckled as he took his finger and started to push on my hole I let out a moan as he began to finger me, he started slow but would move his fingers to hit my prostate and drive me wild, He fingers me pulling on my leash driving me wild, I was hugging me pillow going insane, once he was done he lubed up his cock and told me to hold my ass, as I spread my cheeks he slowly started to insert his cock, I could feel myself stretching out to make way for his cock as the head popped its way in, Omg I panted, as he pulled it out holding me open it lubed it some more and slowly inserted again this time he slid it further I let out a little squeal, as he repeated this until it was all the way in, He pulled my collar lifting my head Good girl he whispered in my ear before he pulled me in and we started kissing, he began to thrust into me as we kissed until I couldn't control myself and I let go of my ass and gripped my pillow. I could feel his cock swelling and growing in me, As he just kept pumping me, He grabbed my arms holding me up and close to him I felt his cock really swell as he kissed me again letting out a large grunt, Suddenly I felt his cock pulse and release his seed, I could feel my bussy swell as it took in his huge shot, I was motionless feeling myself fill and his cock pulse a few times, he stopped kissing me looking into my eyes, your all mine sissy as he pumped his cum deeper before letting me fall down and off his cock, I just lay there for a second catching my breath and letting my bussy breathe as I felt him insert a plug. Let's not let that leak out yet. As he rolled me over to look at him he pulled my leash to his cock to clean him off. I layer back down we had a little laugh as he looked down and saw I had leaked a little, he wiped my cum and fed it to me as he rested his cock on my cage, comparing size. After I had caught my breathe I offered him a drink and something to eat before we started round 2.

I hope you all enjoyed that I definitely did. Started leaking through my cage just thinking about it. Really want to try it some time

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2 years ago