Becoming A Sissy Baby

Chapter 30: Surprise

Sam's POV:

A roar of laughter erupted from the room as my cheeks flushed. Someone suggested they can't imagine me behaving like a puppy. So, Miss Claire then proceeded to connect the leash around my collar and walked me across the room.

I felt others smacking my butt which Miss Claire encouraged saying I get a hard-on by getting spanked. Which earned a few more swats and chuckles as she walked me towards each guest present. I had to kiss their feet and lick their shoes till Miss Claire said stop.

Then she played with me making me run around, and bark, jump and roll over for everyone. I did as instructed adding my own spin to make it look more embarrassing and put on a show for everyone in the hope that Miss Claire would give me the Star.

After they had their fun with me, they were laughing out loud. The whole room was filled with voices of laughter. On the inside, I was ashamed and embarrassed but on the outside, I pretended to smile. I think I am doing great. Everyone seems happy.

"Okay everyone I have to tell you something. You see I promised Sophie here that if she behaved well and everyone was happy then I would allow her an orgasm. So, is everyone in favour of letting little Sophie play with her sissy clitty?" Miss Claire asked.

"Yes," I heard unanimously as I felt relief. Finally, I get to have a proper orgasm. All my hard work is going to pay off now.

I stood there while I felt everyone around me move. Miss Claire's heels clicked as she walked away probably to get the key to my chastity. Guests mingled around me. asking me to bend over so they can see the dildo wedged in my ass. Smacking me while laughing what a pathetic sissy I am.

Or saying how they Love my panties as they are perfect for a sissy like me. they pinched me in my nipples and butt and cheeks while I yelped. Someone then asked me to lie down on my front and then another wave of laughter came when they saw my dick. Saying what a small sissy clitty I have and how I am rightfully locked.

They kept making fun of me for everything while I could only let them. I am so close to my orgasm that I am not going to mess this up. So I behaved accordingly, putting on a show of embarrassing myself further to keep everyone happy till Miss Claire came back.

Which she did jingling keys. She made a show of opening the cage. Letting everyone gawk at my private parts then she asked me to get on all fours while she took out the dildo in my ass. Strangely enough, I did feel so empty.

I wait in anticipation thinking how I would be cumming. Maybe I will give myself a handjob? Or will I get a blowjob? Maybe I will even get fucked. My dick wants inside a warm and soft pussy, it feels like forever since I had my last fuck.

Miss Claire then asks me to kiss the dildo, which I happily comply with as I know that means it will be put away. I give it the best blowjob I can, licking and slurping while deep-throating it. Miss Claire told me to stop and I immediately did.

"Now Sophie I want you to be very vocal, don't try and suppress your sounds. And I also want you to speak, say what you are feeling and how you are enjoying. If at any point you go quiet all this stops. Understand?" Miss Claire asks and I nod in excitement

She asked me if I was ready for my orgasm and I said yes in anticipation. What happened next was something I never thought of. Someone grabbed me from behind and slammed into my asshole.

I yelp with the pain as it earns me a smack. They went hard on me pushing fully in and out and within seconds I was a moaning mess I didn't want it this way but I will take what I can get. I kept moaning saying how good this feels, how I Love having a cock in my ass, and how turned on I am. I was lost in feeling when I orgasmed. Letting out a satisfied sigh.

"You did so well Sophie. I hope you enjoyed that" Miss Claire says

"Ywes Miss Claire. I wuv gewtting fwucked in my sissy pussy so much. Thwenkyou Miss Claire" I say genuinely

I felt someone bend before me and I lifted my face. They removed my lenses and I saw Miss Claire, giving her a droopy smile.

She got up and moved away and my vision started returning. I was horrified to see the room full of women some were laughing with tears, others were holding onto their stomachs in laughter. I momentarily forgot that there were other people there.

But the worst part was I recognized everyone. They all were my ex-girlfriends. All of them are present in the same room. Pointing at me laughing their asses off.

"What a faggot!"

"Look at the mess he made"

"he certainly loves to be fucked in the ass"

They made filthy comments on me as a new wave of embarrassment washed over me. I was in the centre of the room, wearing cutout panties with my cock out getting fucked in the ass in front of all my past girlfriends.

"Now Sophie lie down so we can lock you up properly, we wouldn't want you to have any naughty ideas now do we." Miss Claire said and I noticed her wearing the strap-on with the same pink dildo that was in me all evening.

I was in shock as I lay on the floor while they all laughed at my now flaccid cock while Miss Claire made quick work of locking me in. Then she pulled me onto my knees

"Don't you want to thank your good friend dildo for giving you so much pleasure?" she said as the dildo touched my lips. I shut then closed but then someone pinched my nipples and I screamed in pain as Miss Claire shoved the dildo in my mouth hitting the back of my throat while I was gagging and choking on it.

After she was satisfied with the dildo being cleaned she made me beg her to put the dildo back in my ass as it feels so empty. I didn't want to do it but I was punished with swats from the riding crop till my skin was red and throbbing then I was told I needed to beg again. This time I did what was expected of me.

The dildo was slid back into my mass and I got a few spankings from my former partners as Miss Claire instructed me to get up and start serving again.

------------------------⚜⚜⚜------------------------

Constructive criticism is appreciated.

Please comment, vote, and give your feedback on this chapter.

have a great day!

⁓TinyTales