Jacki's Journey into Sissyhood Pt. 02

"Wow, that is amazing," I exclaimed as I starred at a feminine young goddess in the mirror. I saw what she had meant about my makeup job, this was totally different. It wasn't too heavy, but lite and fresh. The transformation was made perfect by the new styling of my dark hair. It was a hip, young luck, kind of punk-rockerish but was quite cute. "I love my hair."

"Yes much better than that cheap mop you were wearing," she laughed.

As much as I loved my blonde wig, I had to agree with Laura, this was much better.

"Now that's out of the way, on to the outfit," Laura noted as she started digging through my bag. "No, no, no, oh the shoes are cute, no on these things. The butt plug and the shoes will work." She turned to me and told me, "Stand up dear."

I stood up as she twirled me around, "yes, I have something I think will work." She disappeared into her closet, on to return a few minutes later carrying some clothes. She dumped the things on her vanity and then held up a hot pink, vinyl overbust corset.

"Have you ever worn a corset before," she enquired as she sized me up.

I shook my head, "no."

"That's fine I can help you get into it quickly, so strip out of that dress and bra," she commanded. I hesitated a second, and she laughed, "Don't be bashful, I'm going to see it all anyway."

Upon her encouragement, I quickly let my dress fall to the floor, then unhooked my bra setting my breastforms free. She squeezed on of the false tits, making a disapproving face, "These really don't work on you, but they will have to do for now."

She then unclasped the corset and draped it around my body as she instructed me, "Start fastening the clasp from the bottom up."

I followed her instructions, fastening each steel clasp bottom up until they were all done. She then tugged the corset into place, and stuffed my silicone tits down at the top, and motioned for to sit. I sat on the stool in front of her, holding the top in place as she had wanted. I was the instructed, "Now take a deep breath and hold it." As I did she began pulling on the laces of the back of the corset, tightening the fabric against my body. She tightened and tightened, and then tightened some more. The vinyl material and steel ribs of the corset compressed and reshaped my torso. It felt as if all my organs were being squashed together. Eventually, Laura tied off the laces, and told me, "Now breathe out."

I did as I was told, but found it incredibly hard to get another breath. Laura place her hand on my bare shoulder and said, "Breath slowly in through your mouth and out through your nose." I followed her instructions and was able to regain my composure.

She laughed, "You'll get used to it I promise." She then handed me a matching pink thong, and a pair of white fishnet stockings. "You can handle it from here, I need to get myself ready, oh and just wear your white peep toes you have on with that outfit." She motioned me out into the bedroom and told me, "get ready in here, I'll be out in a minute."

I carried my things into the bedroom and laid them out. I started by trying to take my green thong off, only to find I was unable to bend at the waist in the constricting garment. I finally figured it out and wiggled the thong off. I then stepped into the pink thong that Laura had given me, I squatted down and drug the satin thong into place. It just barely covered my clitty and was little more than two strings running up my ass crack. Next came the stockings, which took some imagination on my part. I stood up and placed my foot on the bench at the foot of the bed, from there I was able to draw each fishnet stocking up and fasten the garters. Holding onto one of the bed posts, I then stepped back into my heels.

"What a sexy sissy slut you make," Laura called from behind me. I spun around to face Laura wearing a purple, open bust corset. Her massive tits hung free, unsupported. She obviously had some work done, as they didn't sage but just sat on her chest and bounced with her every movement. Her plump nipples were pierced with metals bars that caused them to glisten. She wore black fishnets stockings and high heels, with a large strap on dildo fastened across her pussy."

"I think that might fit you better than it does me," she joked. She moved across the room towards me as my eyes were affixed on the large rubber phallus, she wore. She came up to me and kissed me firmly, sticking her tongue down my throat. I returned her kiss as her manicured hand dug into my exposed ass cheeks. "Where is Steve," I protested.

Laura kissed me again, and said, "He told me what a good fuck you were, so I thought I give you a test drive before he joins us." She licked her lips and looked at me lustfully, "why don't you show off your cocksucking skills, on my friend down here," while she shook the fake cock with her hand.

She placed her hand on my shoulder and commanded, "On your knees."

I lowered myself to my knees and took the dildo into my hand. From this angle I could see that while one end of the cock was in my hand, another end was firmly inserted in Laura's juicy cunt. I looked up at Laura as I began sucking the shaft of her toy. She moaned and sighed, "Good girl, Jacki."

I covered the shaft in saliva and then used my hand to milk the shaft as I bobbed up and down on the shaft, as I had done on Steve's cock. "Well, aren't you just a cock loving slut," Laura chided as I made love to her strap on.

After a minute or two, I guess Laura became bored, and pulled the cock from my mouth, "Steve said you can take all of him in your mouth, let's see if you can deep throat this." She grabbed my head and held it still and drove her tool into my mouth. I swallowed as much as I could but her speed and length made me choke with about an inch of shaft left. "Not quite, but we can work on that."

"Enough of that, let's see how well you fuck," she insisted as she pointed to the bed. "On your back sissy bitch."

I hopped to my feet and moved quickly to the bed, and laid down as instructed. Laura grabbed a bottle of lube from the dresser and followed me onto the bed, taking her place between my legs. She greased her rubber cock saying, "Legs up, grab your heels."

I grabbed my heels and pulled my legs to my chest exposing my ass to Laura. She pulled aside the pink cloth string, and massaged my hole. "What a pretty pink pussy you have sissy. You want me to fuck your slut ass with my big cock Jacki?"

"Yes fuck me Laura," I answered.

My response was followed by a swift smack of my ass, "No, sissy in here, I am Mistress," she jeered angrily, then swatted my bare bottom again.

I jumped and yelped at her smack, "Yes, Mistress."

She then lined up the fake phallus with my hole and pushed into me. Steve had been slow and easy, Laura was anything but. As soon as the head cleared my sphincter she buried the cock in my pussy. My eyes watered and I gasped in gain, "Oh shit, that hurt."

My tears, had little effect, as she immediately withdrew the strap on and slammed back into me laughing as she did so. Laura continued her strokes as my ass throbbed around the dildo. As she worked herself in and out she began to moan as the other end of the strap on stimulated her pussy. The pain in my ass began to yield to the pleasure of the cock stimulating my prostate, and I too began to moan. My cries of satisfaction, caused a lustful smirk to appear on Laura's face. "I knew you were a cockloving sissy at heart, tell me how bad you need mistresses' cock."

"Oh god, that's it, your cock feels so good mistress. Fuck my pussy harder mistress. Please fuck me," I pleaded.

Either her clitoral stimulation or my cries cause her speed to increase, as she continued pounding me. In and out, in and out; faster and faster she went as the replica penis probed my bowels. All of sudden she shuddered and slammed into me, and shouted, "Oh yessssssssssssssss, I'm cumminnggggg!!" She collapsed as her body conversed in orgasmic bliss.

Laura gathered her composure, and removed the phallus from me. I objected as my now empty pussy throbbed for cock, but Laura laid down beside me and said, "Time to put the pretty mouth back to work."

"Yes mistress," I replied, then crawled between my legs.

"Clean up my toy, first." She harassed as she waved the cock in my face. I returned to sucking and cleaning the rubber dick, tasting my ass in the process. To my surprise I tasted good, and I happily lapped at the dildo. Laura unhooked the harness, and slid the strap on from her vagina. She then stuck that end into my mouth, giving me the first taste of pussy in over a year. Her scent was primal, and strong, and her taste mellow and smooth. I greedily lapped at the pussy stick till it was cleaned thoroughly. She sat the strap on aside, "now make me cum again," she said and tapped her pussy.

"That was the only instruction needed and I dove in lapping her labia like a dog, she cooed and groaned. I felt her hand grab my head and then jam my face into her sex. My nose dug into her pubic mound and my tongue fought at her clitoris. She moaned and began grinding her hips into my motions. I looked up at her lost in ecstasy. Laura then looked up and motioned to someone else in the room to join us. I never lifted my head as to keep with my task to make her cum, but crawled to my knees and lifted my ass into the air, as the bed undulated and the visitor climbed aboard.

"She's such a good slut isn't she, her hole is nice and ready for you just slide right in baby," Laura instructed the stranger. I then felt two large hands on my hips and the familiar feeling of Steve's hard cock at my love canal entrance. My earlier fuck session with Laura had indeed loosen up my tight pussy, as Steve pushed is meat into my rear completely.

"Oh god, yes," I muttered into Laura's pussy, while Steve began fucking my hole with his rod. We continued fucking and licking in ecstasy for several minutes. My tongues gyrations on Laura's button began to bring her close, she threw her head back and moaned loudly, and her hand kneaded and teased her nipples. His girlfriends cried of joy, kicked Steve into high gear, his trusts quickened and his balls began smacking my taint. The motion of Steve's cock sent me over the edge first, sending ropes of cum from my clitty, and began to drip down as the satin G-string did little to contain it. As my ass orgasmed, I sucked hard at Laura's clit, sending her into a second orgasm. The spasms of Laura's body, caused Steve to grunt then bury his sword, and began spilling his seed into my sissy pussy.

We froze in that position as our heads slowly stopped spinning. Laura broke the silence, "Holy god, that was intense." We all laughed in agreement. She then looked at Steve over my shoulder, "Did you cum in Jacki?"

I interrupted, "Yeah, like a fire hose." We all giggled as she grabbed my butt plug from the night stand, "Here you go honey, plug her pussy so she has something to take home." Steve took the plug, removed his cock and inserted it into place. He tapped my ass, "There you go, baby. We will let that cum incubate in there for a bit."

We all collapsed on the bed in our post sex stupor, and laughed and talked. Apparently Steve had been in the room for pretty much the whole session, I had just been so focused on making Laura happy that I didn't notice.

"Well Laura, what do you think? Did she pass the test," Steve asked.

"With flying fucking colors, babe," Laura exclaimed. I blushed as the two gushed over me.

After a while we climbed out of bed, as it was early in the a.m. now, and I needed to get home. Laura told me to keep the clothes as a gift. Since it was so late, and I was too tired to change, I borrowed a mini skirt from Laura to cover my ass gathered my things and headed out.

Laura walked me out, putting her phone number in my phone along the way. She told me as I loaded my bag into my car, "No pressure, but I'm really excited about where this could go, I think you really enjoyed yourself tonight," as I nodded in agreement, "well I know we did to. Thank over our offer, and when you're ready, call me and we can talk."

"Ok, Laura, I will," I replied.

We kissed passionately goodbye and I made my way home.

My drive was a blur, as my mind danced with images of the night and the offer at hand. I had never intended on becoming a woman or a sissy, I quite enjoyed my old life as a man. But I had just had two of the most powerful sexual experiences of my life, like mind alerting sex, as a woman essentially. My mind was so preoccupied that I never even thought to look around the apartment complex before walking to my apartment. I was still wrapped up in post sex euphoria.

I closed the door to my small one bedroom flat, and it seemed emptier, bleaker than it had before. I set down at the table, to hear a "rap" as my crystal plug touched the wooden chair. It reminded me that I was still carrying Steve's payload. I had to see my trophy for the night, I placed a bowl on the floor and squatted above the saucer and removed my plug, pushing the large glob of jizz from my rear. The cum splashed into the container. Once I was empty I picked it up. The bowl now contained about a quarter of a cup of still warm jizz, from my sex partner. There was never a better sign that I was now a sissy slut forever.