Sissy to Military School Pt. 02

Our bodies were both covered in sweat. Jack was grinding and pounding me into the mattress. My cock sliding on the sheets. My entire groin was a wet spot. I could hear the undeniable slapping of flesh on flesh as he had picked up the pace. Every time it seemed my anal ring was open just a tiny bit more. I felt him stop as he lay flat on my back. My anal ring had spasmed and half his cock head had penetrated me! I was gasping for air. Jack on top of me asked, "How is it, baby? Do you like my cock in your ass?"

"It's not as painful as I thought it was going to be" I replied.

Jack ground his hips in a circular motion. His cock head popped in past my anal ring. Once the crown of his head passed through, that's when I saw stars! That pain shot through me! I buried my face in his pillow again, this time in pain I groaned. Thankfully he stopped, laying perfectly still. His pecs pressed against my shoulders. His cock head still buried in my sphincter.

Jack said, "You're wonderful baby. Relax take a deep breath." Take a deep breath he says?! I was hyperventilating into the pillow! I raised my head out of the pillow taking a deep breath as Jack suggested. The pain was ebbing. I pushed back with my ass.

"God, you're so unbelievably tight." Jack whispered into my ear."

"I told you, I've never done this before!" I replied.

I felt like my entire ass was stuffed to the brim. Only his cock head and an inch of his shaft were in me!

"How could girls do this on the regular," I thought to myself.

I rose up onto my elbows. "nnng," I grunted with my eyes shut tightly.

Jack followed me up, his hands on my hips. His cock driving deeper into my ass. It felt like his cock was spreading my anal walls apart! I braced myself into the four-point stance. I was in the full-on doggy position. My hair was plastered to my face. My body had a sheen of sweat. I could feel the last bit of Jack's cock slide into me. I let out a sigh of relief! It felt like I could feel his cock in my stomach! I could feel Jack's balls bump mine. Jack's hands were on my cheeks squeezing them.

"God Steffi, your ass is so perfect. I'm balls deep in you. Your ass is gripping my cock so tight!" I wiggled my ass on his cock. Jack let out a hiss.

He started pulling his cock out and stopped as his cock head was just inside my anal ring. He then slowly pushed all the way back in. I could feel his pubes on my ass. He began a steady rhythm into my ass. The pain was gone. Replaced by pure physical stimulation in my ass ring. There was no more resistance. My ass ring was now stretching and pulling along his cock shaft. I could feel his cock head deep within my ass. He was hitting that perfect spot. Making me shudder. It felt as if he was fucking my cock from the inside. My cock was drooling fluid.

Jack slapped my ass cheek again. My anal ring involuntarily clenched around his shaft.

"Oh god I'm close, I think I'm cumming. Please keep going!" I wailed!

"Keep going, what do you want me to do Stefi. Tell me what you want." And Jack slapped my ass again.

"Fuck me, Jack! Please keep fucking my ass!"

Jack really picked up the pace. He was hammering me. I was no longer thinking clearly! There was heat radiating from my asshole to encompass my entire ass. Jack slapped my ass again. "Maybe that's the heat encompassing my ass!"

Jack said, "Who's my girlfriend?" As he drove his cock balls deep into my ass, he pulled my hips back, forcing my ass tight to his groin. My legs were trembling, every nerve in my body seemed to be connected to my anus! I think I was in a constant state of cumming!

"I am," I breathily replied.

"You are what?" Jack asked as he was pounding me at a feverish pace. He slapped my ass again! My body was no more than a wet rag, my entire body was in rhythm to his furious pace. Attached to his cock by my anus! My thighs were covered in the fluid steady streaming out of my cock. Had I been cumming this entire time?!

Jack slapped my ass cheek again. "You are what?"

"I'm your girlfriend!" I shouted. There was an explosion coming from my cock! Now, this was beyond cumming! I fell into bed. My body was totally spent. I was supremely satisfied. Jack was still fucking me at a furious pace. "How long can he keep this up? God my entire ass is numb!" I thought.

I felt his cock twitching in my ass. "I'm cumming," Jack said.

I ground my hips and mashed my ass into his groin as I felt his cum filling me. I could feel it sloshing at my anus as he slowly churned into my ass. I could feel him going soft in my ass as he rolled off me. Laying on his side facing me.

"I guess it's official," Jack said.

I turned and looked at him, still on my stomach; cum leaking out of my ass, smiling exhausted and contented. I said," I'm your girlfriend." I closed my eyes and drifted off to sleep.