Autobiography Ch. 02

Amanda was one kinky bitch; she left me locked me locked in a pair of pink stilettos, this also included a removable pink harness and dildo, and she wouldn't be back until Friday which was a few days from now.

Our next meeting would be on Friday for another fun filled kinky role playing adventure; girl on girl action. I was to accompany her to a party dressed as a female which would, like usual, lead to a night of out of this world sex. However, to be perfectly honest, I was beginning to over think my predicament and fear started to creep into my mind.

What if I was found out?

Would the guys literally kick my ass if I was found out?

Not only that; but my identity spread throughout the school, the ridicule, the embarrassment... my parents.

I was perched and needed a glass of water to quench it which brought me back to reality as my stilettos hit the floor.

I chuckled as I looked down to see the pink stilettos locked to me feet; a small price to pay to continue my relationship with Amanda.

I steadied myself as I used the nightstand for leverage; once up I tiptoed to the sink filled my wanting desire.

Now, for the truth; would I be able to adapt to walking in these shoes or not. I cautiously took one step at a time as I steadied myself on the kitchen counter top then laughed as I successfully reached the end of my first journey.

Now, it was time to venture freely around the condo. I made it to the isle taking one single step at a time, now; it was time to venture to the entry door and back.

My confidence was soaring on my successful venture and it was time to conquer these shoes once and for all. I began my journey across the floor once more at a normal pace; half way to the door my ankle twisted and I fell to the floor as I lifted the weight off my ankle.

The next three hours I practiced walking until I was confident in my balance and pace then I took a break to have a bagel with cream cheese and a coffee.

As I thought; I wondered if I was really walking like a woman or a man in heels. I picked up my cell and went on Google and entered a few key words and gathered all the info I could muster up to help me in my quest.

I hurried, well, as fast as a novice, like myself, could walk in stilettos to my mirrored closet in the bedroom. From the opposite side of the room I began my walk toward the mirror and found the stilettos actually gave me the mild every day feminine sway to pass just as long as I keep my shorter steps.

For fun, I walked toward the mirror swaying my hips like a runway model which in turn sent off erotic sensations throughout my body; it was the pink dildo up my rear hitting the right spots while swaying my hips. I practiced for my runway walk for a little while more before becoming overly excited and spewing cum all over the floor as I held on tightly onto the isle.

I cleaned my mess from the floor before unbuckling the harness and removing it along with the dildo. Having worn it all night I felt empty and reinstalled the harness along with the dildo.

I practiced walking in my stilettos for the rest of the day. Around eight pm I removed the harness and gave myself a sponge bath. Though the feeling of the dildo up my rectum was exciting I removed it for the bedtime not wanting to rely on it for an orgasm.

** The next few days I practiced in my heels and used the harness sporadically at best. I also connected to Youtube to study women's poses and to steady my walking,

** Friday morning was finally here and my girl-on-girl date with Amanda was about to take place. I got out of bed and did my morning rituals and waited for Amanda to contact me. It was about eleven-thirty when she text me that she'll be here around noon.

When she finally arrived she insisted that I walk to show her I've been practicing like she had told me to; I even threw in a few lady-like poses.

"Very good," she smiled.

"How about a little action?" I asked nodding toward the bedroom.

"Sorry, no time for that; but I do need you to shower and shave your entire body," she smiled taking out hair removal cream and a razor from her bag.

"My entire body," I replied.

"Fine, go as a hairy girl," she remarked.

The thoughts of a thorough ass whipping entered my head before I took the cream and razor from her.

"It's not that bad; besides you don't have much hair anyway," she laughed.

"That's a relief," I smirked.

"Do you want to call off our date?" she asked.

"I don't think that's an option after wearing those shoes the last couple of days," I replied.

"Good, I'll help you shave in your not so reachable places," she laughed as she squatted and unlocked the shoes.

"My calves feel a bit strange," I admitted.

"Stop complaining; you'll be back in stilettos later," she giggled.

"It really wasn't a complaint," I said as I stepped into the shower and began rubbing the cream all over my body.

"Good, then it's on; from this moment on you listen to me if this relationship is to flourish," she giggled.

The cream worked its magic as I rinsed off all my unwanted after shaving my face, arm pits, and groin area.

Once I passed inspection she instructed me to dress simply; a tee shirt and jeans.

Instead of taking me to her place she took me to the hair salon in the mall.

The girl at the front desk walked us to the back of the salon and sat me in a chair. There, she introduced me to the owner who proceeded to give me the look over.

"Amanda, nice to see you again," a man's voice relayed from behind me.

"Nice to see you again," she said as they kissed one another on the cheeks.

"Hi, I'm Victor," a man introduced himself.

"Hi, I'm Zack," I replied.

"What can I do for you today Zack?" Victor asked.

"Well," I stuttered looking at Amanda.

"Well, we have a girl-on-girl date tonight and will be attending a party; he has to be one-hundred percent passable," she explained.

"Well young man you have a full head of hair; it looks like you let your crew cut grow out a bit; but it's too short in the front for a cute bob... a nice full layered pixie would suit you... and with a few golden ad platinum highlights will certainly give you that classy and sexy appeal," he told me.

I looked at him like he was speaking Martian.

"Victor, that's perfect... and do the ears too," Amanda told him.

"Zack, should we go for it?" Victor basked me.

"Sure," I looked up at Amanda; this was her show and I really had no idea what a bob or a pixie was.

"Victor, he's fine with everything... and add a manicure please," she giggled.

"Okay," he said as he went to work on me.

"I'll be back in two hours," Amanda told me before she left.

Victor turned me toward the mirror as he was finishing up.

I couldn't believe the person looking back at me was me; I looked like a fucking girl.

"How do you like it?" Victor asked.

"I look like a girl," I replied. My hair was teased; an imaginary side part .

"That was the effect you were looking for, correct?" he smiled as he turned me back around.

"Yes," I smiled just because I couldn't believe the drastic change a haircut and highlights could do to my appearance.

"Okay Zack, close your eyes," he told me as he turned my chair away from the mirror.

"OW," I cried out as I jumped slightly.

"Zack, I didn't hurt that much," he laughed.

"What happened?"

"I just pierced your ears," he continued laughing.

"Why?"

"Zack, don't act like you didn't agree when Amanda said to do your ears too," he giggled.

"I thought she wanted you to trim around my ears," I admitted.

"Well, she wanted you to be one-hundred percent passable, that means two pierced ears not one," he smiled.

"Fine," I took a deep breath, relaxed and let him pierce the other ear.

Victor wiped my ears down and inserted something into my ears then spun me around toward the mirror. I opened my eyes and I was just stunned by my appearance; the earrings just made my entire look pop.

"Oh... my... gawd," Amanda walked up to us.

"What do you think?" Victor asked her.

"Perfect, just perfect Victor," Amanda remarked excitedly.

"Thank you," Victor replied.

Amanda made me pay the bill and we were out of there but I felt uncomfortable as soon as my feet crossed the threshold; I looked like a clown with a girl's haircut and earrings. She sensed my nervousness and clasps my hand until we got to the car.

She complimented me on how beautiful I looked and everything would be fine; especially once I was dressed.

Amanda walked me back to her bedroom once we got to her place and began explaining how and why as she applied my makeup. I found my transformation amazing as I watched my androgynous look morph into a beautiful woman. From eyelashes to fake nails; it was simply amazing.

"How do you like your new look?" she asked excitedly.

"Amazing," I answered with enthusiasm

"Watch this tutorial and complete the task," she demanded as she laid her cell phone in front of me.

It was a tutorial on how to tuck your testes into their sockets; though at first painful I was finally successful on the ninth try; the second one went in after three tries.

"How's it going?"

"It was difficult at first but I'm done," I replied as my cock was stiff and standing at attention.

"That's not going to work; if you cum now will you be able to cum later?" she asked looking at my hard cock.

"I'm confident that won't be a problem," I assured her only because this whole scenario was such a turn-on

"I'll be right back," she said as she left the room and returned with a glass.

I had no idea what she was up to.

"Lean against the vanity and spread them," she ordered as she reached between my legs and began milking me.

"Ah... ah... ah," I moaned as she stroked me.

"Moan like a girl," she insisted.

"Ah... ah... ah," I moaned.

"That's much better," she giggled.

I really got into character once I began moaning like a female and ejaculated into the glass she held right below my cock. Once drained she set the glass on the vanity and lubed my ass liberally. She stood, went to the closet, and retrieved a black/silver dress and black dress from her closet including a mid-sized bag.

"Panties," she pulled a pair of black laced panties from the bag and handed them to me.

I stepped into them; my cock started to twitch as the satin panties rode up my legs.

"Let me," Amanda giggled as she pulled them up and around my waist then reaching through the backside pulling my cock toward my ass and letting go. The panties were thick at the bottom and held my cock in place. "There, no boners," she remarked as she sat and applied her makeup.

I walked around a bit getting use to my cock resting between my legs; it actually felt quite comfortable.

"Hurry, we're running out of time," she told me as she waved me over.

I guess that explains her demands to get things accomplished; apparently we're running late.

"Slip into this like a shirt and clasp the front," she explained as she handed me a black laced bra.

"I have breasts," I laughed.

"They're inserts to give the illusion of breasts; remember, use a girl voice," she explained as she adjusted the bra to her standards.

"Sorry," I laughed.

"You'll be really sorry if you let it slip and get your ass kicked," she giggled.

"I understand," I actually took it t heart as I studied voice fluctuation all day yesterday just for the reason of not wanting to get my ass kicked.

"Now, take your dress and step into it like this and pull it up and then put your arms through the sleeves," she explained as I followed her example and she zipped me up.

"Wow," I remarked as I turned to the full length mirror; I was all in on my transformation.

"It's a Gradient Color Striped Bodycon Dress; very sexy," she whispered into my ear.

"It pretty short... and tight," I said due to it was just inches below my tucked cock and hugged my body

Amanda laughed.

"What's so funny?"

"That's the whole point to these dresses; to show off your assets; you're going to have to beat the boys off with a baseball ball," she laughed.

I laughed.

"I got you the perfect shoes to go with that dress too; three and a half inch black velvet zip-up bootees," she told me handing them to me.

I slipped them on and zipped them up as I sat at the vanity; then stood and walked around the room.

"How do they feel?"

"Great," I answered as I admired my overall look in the mirror. The dress actually showed a female figure, petite, but still female; obviously due to the inserts and my slim waistline.

"Come here," she told me as she stood by her dresser.

Amanda handed me a pair of silver loop earrings, silver necklace with cross, silver wristbands, and a silver watch; the silver matched the dress I was wearing.

Amanda wore a white strapless bodycon dress, which was as short as mine, with gold jewelry; she slipped on her shoes and we left the house.

I now have total respect for the time and effort that women put in to get ready to go out.

** It was around six-forty-five when we pulled into the rich neighborhood and pulled into a driveway; the house was huge and so was the property. Amanda assured me again that everything would be perfectly fine and to stay on track with my voice; she pecked me lightly on the lips before we got out of the car.

We went inside to a house full of people; the girls noticed us but the guys followed us with their eyes. We walked through the crowd toward the backyard to find the alcohol.

That is what a party is all about isn't it; the alcohol and getting wasted?

We found the alcohol; and Sandy.

Amanda and Sandy hugged; Amanda introduced me as Brigitte and Sandy introduced her friend us to her friend Penelope. We talked for some time until we finished our beers, refilled, and then went out on the patio and danced as a group until we were interrupted by Sandy's boyfriend who whisked Sandy and Penelope away.

We headed toward the keg and were immediately hit on by two cute guys; not that I'm into guys, but, I have to give credit where credit is due.

Tom and Rick introduced themselves and then refreshed our beers including their own.

Minutes later Tom and Rick had us out on the patio dancing with them.

What happened next was my fault; I was on my third sixteen ounce beer and let my guard down.

"You're beautiful," Rick told me as he laid his hand on my waist.

I smiled but needed to be rescued and turned to find Amanda... but to no avail.

"Hey, are you okay?" he smiled confidently as he delicately turned my chin toward him.

I smiled again... trying to act as feminine as possible.

"Do you want to go back to my place?" he asked as he lightly kissed me on the lips.

My heart was racing; I was confused... but I wasn't gay. These three days made me feel something I have never felt before; but still... I wasn't gay nor was I bisexual.

"Come on," he told me as he took my hand in his.

"Wait," Amanda called out.

I was saved.

"She's mine." She insisted.

"What do you mean?" Rick asked curiously.

"We're lesbians," Amanda answered as she stood beside me and kissed me on my cheek.

"Bullshit," he laughed.

"Well, we're bisexual; but... I'm fucking her tonight," Amanda giggled making me giggle in relief with her.

"Fuck, can I watch?" he asked.

"No, maybe next time," Amanda smiled.

Amanda clasped my hand and walked me to the staircase; she turned and blew Rick a kiss as we headed upstairs to a bedroom.

I have to admit, I felt bad for Rick, really bad; he was good... but not nearly as good as me. He could have bedded any girl tonight but unfortunately he didn't have any girl... he had me.

We reached the open upper hallway; Amanda opened a bedroom door and motioned me to enter first; and that's exactly what I did.

The door slammed behind me.

"What happened to Tom?" I asked.

"Do you really want to know or do you want to fuck me?" she told me seductively.

Amanda approached me and put the most brutal passionate kiss on me. Then she reached behind her back, unzipped her dress, and stepped out of it.

"Unzip my dress," I insisted turning my back toward Amanda.

"No, panties off only for you," she gave me that devilish smile. She dropped down to her knees, pulled down my panties, and began to suck my cock.

"Oh yeah," I moaned enjoying her warm mouth wrapped around my cock.

"You like that?"

"Keep going."

"Mmm," she moaned.

I quickly became hard as a rock and she stopped.

"What's wrong?" I asked.

"Do you want to fuck my pussy or my mouth?" she asked; then she pulled me down onto the Persian Rug.

We had one of those forever kisses but I was horny as hell and eager to get to her sweet nectar. Excited, I broke the kiss, slid beside her, and began kissing and lightly sucking on her neck while fondling a nipple. Eventually, I moved on from her neck and concentrated fully on nipple play; both with my mouth and fingers. Once she started getting anxious I slid my hand between her legs and began rubbing and fingering her soaking wet pussy.

She finally had enough, opened her legs, and pushed my head into her crotch where I enjoyed her sweet nectar.

I definitely wasn't use to wearing a dress and found it to be slightly binding compared to be totally naked.

Amanda moaned until she finally motioned me to mount her; she grabbed my cock and led me to the promise land.

We fucked for at least ten minutes before I felt two hands shoved me forward burying me balls deep into Amanda; confused... I froze.

"Kiss me," she whispered softly as she pulled me in and kissed me passionately.

Suddenly, my skin tight dress was forced up and over my ass. Now, I panicked and tried to pull away from her kiss but to no avail; she had her hands locked behind my neck.

Next, a warm body snuggled up to my backside. The look on my face probably said it all as I peered deeply into her eyes awaiting some kind of explanation.

"It's okay," Amanda whispered sweetly.

Her voice was calming but still my heart began to race.

Something brushed against and teased my back door; it was a real dick.

"It's okay," Amanda again whispered sweetly.

The look on my face must have said it all as the pressure of his cock pushed against my opening.

I immediately began to pant heavily holding my breath for a second before exhaling again.

"It's okay," Amanda smiled.

"Ah..." I sustained as his the head of his cock penetrated my pre-lubed orifice and parked. It was obviously bigger in girth than the dildo I was use to; I could tell by girth and pressure upon it's entering my orifice.

"It's okay," Amanda whispered trying to calm me.

"Ah..." he pushed forward and then stopped.

"It's okay," Amanda smiled.

He pulled his cock out slightly just to put it in deeper than before.

"Ah..." my panting became heavier as the pressure inside me was building.

We continued this pattern until he was more than half way in.

"Ah..." I maintained as he slowly pushed the rest of his manhood into me stretching my cavity. My head dropped and rested on her right shoulder, my panting raced like I just ran a marathon and my head was spinning a million revolutions per minute.

"I love you," Amanda whispered into my ear then kissed me.

I was completely out of it; but... I was completely into it. I had no rhyme or reason for my thoughts, emotions, or what my body was going through; though it was leading the way.

I moaned and continued to pant heavily as he slowly fucked me; and I mean really slowly.

Amanda continued to kiss me lightly and run her hands through my girly hair trying to calm me as the man behind me had his way with me.

Minutes later he stopped leaving me balls deep inside Amanda and the head of his cock past my sphincter.

I was emotionally and physically high and was not thinking straight.