Jacki's Journey into Sissyhood

He then positioned himself in between my legs, aligning his weapon of ass destruction up with its target. I jumped a little as his soft cock head probed my entrance. I was full of lust, as I whined like a bitch in heat, "Pop that cherry daddy."

He slowly applied more and more pressure as he tried to impale me. The pressure was intense, and I tried not to fight it. I was beginning to think his swollen penis wasn't going to fit, when the enormous head popped free. I gasped in pain as I pulled Steve close and clamped down my sphincter mussels around the invader. He softly whispered in my ear, "Relax baby, Daddy isn't going to hurt you. Just relax and the pain will subside."

I tried to relax and as I did the throbbing pain in my ass slowly waned. With a tear in my eyes, I whimpered, "Ok daddy, I'm ok."

At my ok, Steve began to slowly push further into my depths. Slowly he fed his serpent into my sissy hole until he was all the way in and I was completely filled with man meat. He held himself deep inside of me, allowing me to adjust to his size as he kissed me intensely. Gradually my ass began to loosen and when he felt my death grip on his penis subside he began to slowly withdraw his cock about an inch and the replace it. I began to groan through our kiss as his body began to undulate on top of mine.

As I moaned, "Oh, daddy," his pace began to quicken and his strokes became longer. He would guide his member half way out then bury it to the hilt in slow smooth motions. As he withdrew and entered his cock began to stimulate something a spot in my bowels. The motion of slow love making caused the stimulation to grow ever more intense. As with the tongue bath early, my clitty once again began to leak.

Steve then broke our make out session, and pushed himself up and guided my legs up before pushing them down and commanding, "Grab your heels baby, daddy's about to make you his woman now."

I grasped the heels of my pink pumps as Steve set to work. His thrusts became faster paced and longer as he pistoned in and out of my tight pussy with his cock. "Oh daddy, yeah fuck that pussy," as his battering on my ass began. Now as he finished his stroke his nuts were slamming into my ass like little wrecking balls. I sighed and gasped encouraging him on, "Fuck me daddy, make me your slut, your cock feels so good in my pussy, Fuck me Daddy, Harder, Faster."

"God yes, your fucking slut hole is so god damn tight baby," he exclaimed as he hit another gear.

At this point he was slamming my ass with his rod. As his thrusts quickened so did the stimulus of prostate. After of couple about 5 minutes of fucking, I erupted, "Oh God Daddy, I'm cumming!!, " as my clitty began to spurt copious amounts of cum that began puddle on my lace bustier.

My climax must have sent Steve over the edge, "where do you want my load slut."

"Cum in me daddy, fill me up, make me a real slut," I encouraged.

He yelled, "Here it comes slut, oh shit,..., Ohhhh, Gawdddd." He slammed his cock home, and I felt the shaft spasm. Then his testicles unleashed a torrent of cum into my pussy. The cum just never seemed to stop, as his ball unloaded their payload, and soon is was full with cum squirting from around his cock and leaking out onto the bed.

We laid there gasping for air, covered in sweat and jizz, in all our post fuck glory. Steve finally broke the silence, "Now that was hot a hell, baby."

I echoed his sentiments, "I've never came that hard in my life."

Steve's softening cock slid out of my well fucked love tunnel, with a loud suction sound, like removing a rubber boot from a mud hole. As he removed the obstacle, cum began to spill out of my overfilled ass. Steve quickly grabbed my plug reinserting it into me to stop the flow. He looked at me with a sly grin, "That's I lot of cum baby, you might want to save that as a souvenir or something."

I laughed, "Yeah I guess so, how about a taste."

Steve took his hand and swooped up the cum puddled in my ass crack and shoveled it into my waiting mouth. Having never tasted cum, I was unsure what to expect, but it wasn't bad. Slightly salty, slightly sweet, thick in a gelatinous consistency and a hint of vanilla which I suspect was from my body lotion. I finished cleaning Steve's fingers, then he kissed me deeply as we swapped the cum back and forth. He broke the kiss saying, "That was delicious."

I nodded in approval.

Steve looked at the clock, it was now 1:30 in the morning. "Man it late, I guess I should go."

I grabbed his arm as he turned to leave, "or you could stay."

"Are you sure?" he asked.

"Of course daddy, we can cuddled," I laughed.

He laughed back and kissed me once more, "Ok if its ok with you, I'll stay."

"Yay," I exclaimed. "I guess I should cleanup for bed," I said popping to my feet and trotting towards the bathroom. I looked back at Steve lounging on the bed, "make yourself comfortable, I'll be right back."

I kicked off my heels, and threw them in the closet before trotting into the bathroom. I quickly stripped down. Using a washcloth I quickly washed the sweat and cum from my body, and reapplied some lavender body lotion. I removed my old makeup, then quickly reapplied some simple makeup to my face, and some clear lip gloss to my lips. I then began to rummage through my closet. I found my white silk and lace babydoll and matching panties, and quickly got dressed. I brushed my teeth, tossed my wig about then opened the door to the bedroom.

Steve had made quick work as well, blowing out all the candles, and retrieving his boxers. He was now partially under the covers watching TV. He rolled over when he saw me and said, "Wow, well aren't you dressed like my little sissy bride."

"Kind of the look I was going for," I laughed.

He lifted the covers up for me allowing me entry. I slid in beside him as he cocooned me in then wrapped his arms around me, and giving me a soft kiss on the lips. "I hope you enjoyed yourself tonight Daddy?" I enquired.

"I'm still here aren't I?"

I smiled and he kissed me once more. We fell asleep in each other's embrace.

TO BE CONTINUED...