tagTransgender & CrossdressersSissy Tested by New Daddy Pt. 02

Sissy Tested by New Daddy Pt. 02


I leaned back, admiring my work. Daddy's cock stood hard and tall. It must have been almost 10 inches and so thick.

I heard his booming voice. "Time to show me what your other hole can do."

I swallowed hard. This was it, the moment I finally show my new Master what his new sissy could do with her boipussy. I was so nervous, I had butterflies in my stomach as I considered what would happen if I disappointed him. I would be a pariah in the sissy community, I wouldn't be able to show my face at Sissy School again! They took pride in turning out the hottest, sluttiest, most cock-crazy graduates and I had to live up to that legacy. I dreamed of making it into their Hall of Fame of alumni who went on to be champion sluts. But most of all, I wanted to please this man. This dominant, hung, strong man. This was my new purpose in life, to please this man. I was his sissy slut and I had to drain his cock of that cum one way or another!

"Yes daddy," I purred before giving his cock one final lick. I looked at this cock again and imagined it filling me up. My boipussy was about to get re-sized!

"Skirt on or skirt off, daddy?" I asked timidly and in my high-pitched voice.

"On." He commanded. Looks like I was right about this Daddy, he really like for his sissies to look the part and stay in character.

"Yes of course, Daddy!" I beamed - I loved fucking in skirts. This schoolgirl outfit just made me feel so slutty and it would mean I wouldn't be able to see my sissyclit, which was rock hard at this point despite being so puny.

I took a deep breath and stood up on the bed. I paused, trying to sense what position he wanted me in. He didn't move. He was still testing me, trying to see how good of a sissy I was.

I stepped forward, my feet straddling his body, until I was at his chest. If he wanted to see slutty, I would show him slutty! Slowly, I lifted up my skirt and eased my thong lower while shimmying my hips, teasing him. My sissyclit came into view, pointing straight ahead and looking so useless and pathetic. Daddy smiled when he saw my little clit. Somehow that made me melt even more, the feeling of him confirming his alpha place in this world and my role to be under him. His smile just assured me that I was meant to be like this, serving him.

I eased my thong further down, and stopped when it was wrapped under my ass cheeks. I tightened the thong there and started pulling it up and down, making my asscheeks bounce. I looked down at Daddy's face and winked. He stared at me, his stare dominating my brain. I felt to submissive. I felt...owned.

I pulled my thong down more and let it drop to my feet before kicking it away from the bed.

Squatting down, I reached back and grabbed his cock. I could barely wrap my one hand around its thickness. This cock was meant to tame sissies!

"Ok, gurl. You were made for this. You trained for this. And...you're soooo gonna love it!" I thought to myself. Be a good gurl, show Daddy your skills.

I tilted the cock towards my hole. I had put a little lube in there as I was taught to do at the beginning of each day - a sissy never knows if she'll get to serve a man any day! I pulled the cock up against my asscheeks. Mmmm, the warmth of his cock felt like a roasting campfire against my skin.

I slapped the thick cock against my cheeks playfully. His cock felt so heavy! Pointing the cock up and letting it slide right between my cheeks, I reveled in how good it felt to have a big cock like this to dominate me. I shook my ass up and down, letting the cock enjoy my full sissy ass. God, it felt like it just got harder!

But now it was time to give Daddy what he wanted, what he had purchased. I eased my ass back until I felt the cockhead against my hole. It felt like I was trying to inhale a pipe with my asshole! I felt uncertain, wondering if my hole would open up to him. One step at a time, one step at a time.

Easing back more, I felt the crown breach my boipussy. "Nnnnnnngh," I uttered. I start breathing in short stabbing breaths. I backed up a bit more, the head driving into my hole, until the whole cockhead was in. God, he was as wide as my favorite buttplug!

Ok, that was always the hardest part. I looked back and flipped the back of my skirt up. Oh my god, there was so much cock to go!

I started squatting more, taking another inch. This thing was re-sizing my boipussy already! It felt so warm, so thick. I rose up a bit, feeling the cock ease out of my hole. Then I went back down again, letting out a little "Aaaaaaah". I did that a couple times before stopping. I had to take more of this. I eased another inch in then came up again before squatting down more and taking a couple more inches. Each time I took some more it was like I could barely breathe. I was so focused on this task, so focused on getting this cock fully in me. The pain was exquisite. There was such pressure in my ass, like a throbbing pain but one that felt earned. As if this was the silence before the storm of pleasure would break loose.

I looked down at Daddy, his face was unchanged. He wasn't going to do anything, just witness his new sissy acquisition work her body for her master. I was performing for him, so I knew I had to give him a rousing show. I must have had about 5 inches of cock in my boipussy. I tried forcing more in but I felt some resistance. That made me feel so worried! Was I going to be able to take the whole thing? Would I disapoint Daddy?

"Calm down, gurl. You managed to take 5 thick inches in you, that's a good start! Show him what you can with just those 5 inches!"

I eased up and down again, feeling this cock pull my insides around. My boipussy was wrapped so tightly against his cock, it was like a perfect sheath for his tool. Up and down, up and down. I started going faster. The pressure and pain eased up, and gave way to a new feeling. The nerve endings in my boipussy must have turned on all at once because I was in a new world of pleasure! It emanated throughout my body, making my skin tingle and my head light! Oooooh, this is gooooooood!

Faster and faster, I bounced my ass on those thick 5 inches, and I must have fit a couple more inches in with my fast movements! I was bouncing up and down 7 magnificently thick inches of Daddy's cock and the pleasure well inside my asshole was bursting! Oh my god, this was so much fun!

"Aaaah! Aaaah!" I squealed, getting louder. I was bouncing like a madwoman on this cock and loving it! "Oh my god! Oh my god!" I put my hands on Daddy's muscular chest and shook my ass faster.

"Ahahaha!" What was that? Omg, I was giggling! I was bouncing on this cock and giggling like a little slutty schoolgirl! My pigtails were flying everywhere while my skirt flipped up and down fluttering wildly!

"Daddy! Daddy! Daddy!" I squealed in joy, my head flung back and eyes looking to the sissy heavens.

I had to have more of this boipussy-destroying cock.

"Oh yes, oh god, mmmmm ooooooh!" The air stolen from my throat as I sank down further on Daddy's thick dick.

I sank down further, oh god Daddy's cock was conquering new regions of my boipussy.

"Ooooh it feels so...goooooood" I managed to say before feeling my thighs against Daddy's. I did it, I had taken Daddy's cock to the root!

I held myself there, basking in the glory of this moment. No one could tell me I wasn't a slutty sissy queen! I hope I pleased Daddy with this.

Daddy's hands grabbed my asscheeks. He slapped my left cheek hard, my ass jiggling wildly in response. Fuck, Daddy was showing me how much he owned this ass!

And then Daddy just took over! He rolled my ass up and down while pistoning up with his hips.

"OOOOH FUUUUCK!" I yelled, surprised by this onslaught. He wasn't holding anything back, just pounding his new sissy property with abandon! And I wasn't complaining! I was seeing stars as his cock rubbed against my sissy button in my boipussy!

"Ooooh oooh oooh!" I moaned girlishly as I felt his cock take me to new heights. I was getting close. I hadn't spurted my sissy cum in weeks and this was building up to be a big sissygasm!

"Yes Daddy! Yes Daddy! Thank you Daddy! Oooh thank you daddyyyyyyy!!" I trailed off as the words were stolen from my mouth by his jackhammering into my hole.

Then I heard it, "AAAAAGGGHHHH" Daddy groaned loud. Shot after shot after shot of cum jettisoned into my hole. It bathed my insides in sticky goodness. I sank back down on his cock, which somehow remained hard, and felt the cum collect and drip in my asshole. What a feeling.

"Sissy," I heard Daddy's smooth voice.

"Yes, Daddy?"

"You may cum now." And just like that, like he had set off a trigger in my brain, I felt my orgasm shoot from my boipussy throughout my body, climaxing in my head.

"AAAAAAAAAH" I moaned loud, feeling my sissy sperm burst from my sissyclit like a volcano.

"Oooooh" I kept feeling the afterglow of that wonderful assgasm trail out. Oh god, it was like my body was stretching this orgasm out, making me feel warm and full and perfect.

"Oh thank you Daddy, thank you so much!" Where girls may take a rest at this point, this sissy knew her training. I hopped off of the cock and immediately placed myself back between his legs and licked all over. I needed myself a taste of his cum! And it was so thick, and salty and had such a pungent odor. I was going to enjoy this!

When I finished cleaning up his cock of our juices, I kissed it and stood up at the foot of the bed looking at Daddy. My skirt was stained with my sissy cum and I could see myself in the mirror, looking like a well-fucked schoolgirl, remnants of cum all over her face. "Just as a sissy like me should look," I thought proudly.

"How may I serve you now, Daddy?"

Daddy smiled.

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