Sissy Awakening Ch. 02

- A Sissies Choices -

It was sometime in the middle of the night I woke cold, just laying on top of the covers I realized I was hungry as hell too.

Still wearing the clothes they had put me in when I left the spa, I wrapped a blanket around my shoulders and headed for the kitchen. Standing there hungry but not wanting to really make anything I saw the jar of cookies that Sarah had made from a day or so ago. Grabbing a glass from the cupboard I filled it with milk and sat dunking the cookies in the milk savoring the act of eating until the pain in my stomach let up.

Making my way back to my bedroom I tried to strip out of the thin white jumper. The damn buttons were at the back and my finger nails were far too long! I was resigned to the fact that I wouldn't be able to remove the outfit without help from Sarah.

Standing at the door of her bedroom knowing she was likely dead asleep I tentatively knocked at the door. When she didn't answer I knocked again slightly louder, still no answer so I turned the handle quietly opening the door and stepping in. Gently grabbing her shoulder I shook just a little bit.

"Sarah, wake up... I need some help." I leaned in and said to her.

"What the hell do you need right now?" She said not sitting up but just turning her head toward me.

"The spa put me in this outfit, I'm trying to take it off but the buttons are at the back and my finger nails are too long!" I said somewhat frantically.

"Turn the light on sis." She said sitting up in her bed.

I stood in front of her as she sat at the edge of her bed undoing the buttons at the back of my outfit. Looking down at my feet as she undid the second button. I thought back to a couple days ago. I might have been standing in this very spot, but my toes were not painted a bright neon pink, I wouldn't have been wearing a soft pink bra and panty set as my girlfriend removed the buttons from my jumper. I realized a lot had changed in the last two days. I was wearing bras and panties, and being made more feminine each day. Sarah was even calling me sissy, or sis. I liked it when she called me sis because I could imagine we were sisters or at least lesbian lovers, but I just had to eat being called sissy.

With the final button undone on my outfit I turned around and offered a hug to Sarah as thanks for helping me. Reaching down I hugged her deeply., feeling her breasts smash against my chest, my arms dropped to her waist, and my cock began to stir. It felt like ages since I had even touched her, and I wanted to bury my cock deep in her pussy... or have her wrap her arms around me as I drifted off to sleep, yeah... cuddling would be nice too.

"OK go to bed sis." Sarah said as she patted my back three times. I knew that was a universal sign for, we are just friends and this hug is over. Holding the hug for just a moment longer Sarah released her arms from around me. It was just a one-sided hug at that point. Me holding her and nothing else.

"Let go!" Sarah pleaded.

I released her and backed up half a step dropping my head. I just stood there for a moment. I was sad and near tears. Everything had changed in such a short amount of time. I was in shock. My whole life was different and I felt like the one person that I relied on for comfort, my best friend in the entire world was now pushing me away! Tears began falling down my face. Tears I had no control of, they seem to just fall directly out of my soul. I begin to sniffle and sob quietly like a little girl.

Sarah reached out, pulling me into her embrace, she held me tightly, while gently rocking from side to side. I sobbed for long stretches into her shoulder as the back of my outfit spread open and started slouching off my shoulders. Sarah played with the straps on my bra, Running her fingers over the clasp at the back, she lifted and flipped it slightly on my back, exactly like I had done to her so many times in the past. This pulled me out of the fit I was in, and I smiled realizing I was wearing a bra and panties. Still sniffling, I released the hug and whispered an apology in my best friends ear.

"I'm sorry I woke you up, thank you for helping me." I said to her softly.

"A lot has changed and this all happened so fast!" I added.

"It's the weekend so maybe you can relax just a little bit, and maybe we will have some time to talk about things tonight." She said.

"Thank you." I said as I released her and stepped back.

Standing only a foot away, I dropped my head. I wanted to tell her how sorry I was for the things that happened, but I couldn't, I wasn't sorry. I wanted to say I didn't want to make all these changes, but I couldn't. The only thing that I really fear is how society will treat me once I become my true self. Well... the version of my true self that Sarah sees in me. I loved looking down and seeing my painted toes, or seeing my painted nails when I touched something. I loved wearing the bras and panties too! I really loved it all. I just wished people would leave me alone and let me live my life!

Laying in bed wearing just my bra and panties, I began rubbing my hands on my hairless crotch. I was amazed how smooth and soft everything was. Running my fingers back to my butt I touched around my anus. It was the smoothest I had ever remembered being, I could probably shove my fingers right in without any kind of lube. Feeling my penis grow I tugged at the tip, imagining Superman kneeling between my legs. I imagined his codpiece stripped away, he pushed a huge cock into my hungry ass right at the same moment I plunged two fingers deep into myself. Jerking my cock and imagining Superman filling my ass with spunk, I shot cum all across my belly in violent jerking motions. My stomach muscles were stone hard as I cum and my ass was spasming, almost gripping onto the fingers I buried inside myself. I imagined it was milking the final bits of cum from his balls as my orgasm subsided.

Waking the next morning, I strip in the bathroom, dropping my underwear in a small pile I stepped into the shower and leaned against the wall letting the hot water cascade across my body. Reaching behind my head, I started undoing the braid. I ran my fingers through my long hair, and started massaging my scalp. Feeling the wefts of hair where Sarah's friend had sewn them into my own hair ruined the illusion that it really was my own hair. She did a really good job of it though, because when it was dry, I couldn't even tell. Washing my body with Sarah's loofah and body wash, I let the feminine feelings go wherever they wanted that morning. I grabbed 2 towels this morning. One for my hair, which I patted dry best I could before rolling it up into a towel bun atop my head.

I spent a bit of time shaving my face. I didn't want any stubble, and kinda wish they could have just waxed my face too. I then tended to my new earrings, and adorable pink nose stud. I cleaned around the edges of the studs, making sure they didn't get infected. Looking at my face, I noticed the eye makeup had all but worked itself clean from my face and I sort of missed it already. Reaching in the drawer I found Sarah's eye liner and mascara. I was sure she wouldn't mind sharing at all. Hell... just 2 days ago we shared a fucking bed, she could share her makeup too!

Not being super skilled at makeup, I closed one eye and applied eyeliner to it realizing it was far more difficult than I had anticipated. I washed it off 4 times before settling on a simple line around the outside edges of the eye, and as much mascara as I could manage to apply before it tickled my eyelashes too much to continue. I tried a small dab of eyeshadow right on top of my eyelid, and blended it out as well as I could. Finishing off with simple lip gloss that made my lips shine, I felt I'd done more than I probably aught to have for work at a construction company, but I planned to meet with the boss today so I wanted to look nice considering all things.

Moving onto my hair, I pulled it free from the confines of the towel and began drying it with a blow dryer. Everything was more difficult with my new nails. Yeah they were cute but they didn't do anything to help at all! Yeah paint them fine whatever but why do they have to be almost an inch long?

Once my hair was dry I decided to go the simple route for the day. I grabbed a hair tie from the basket on the counter and put my hair into a ponytail as high up as I could manage without it poking up into the air. I tied three more spread out evenly throughout the length of my hair and left it at that. I wished I knew how to do more, there was so much potential with this hairstyle.

Standing at the doors of my closet only for the second time ever, I opened the underwear drawer to started getting dressed for the day. If I'm going to have long girly fingernails painted bright pink, I may as well get used to the entire ensemble. Looking through the bras I find A dark red one with thin shoulder straps and absolutely no cups. Copying a move I saw Sarah do so many times before, I wrapped the bra around my body, hooked the clasp together and then spun the entire bra around pulling the shoulder straps up into place. I lifted the naturally fatty bit of my chest up into the underwire portion of the cupless bra and got a small slightly flabby little titty on each side. A color of panty nearly matching the bra caught my eye and I took them free from all the others. They were a deep red thong that screamed sexy and I was happy about what I picked as I slid them on.

It didn't seem right that I should cover this beautiful lingerie with work pants and a work shirt, but I can't really go do construction in a skirt either though. Headed out the door I was somewhat nervous about the reactions my looks may cause with my coworkers but I was beginning to not really care what other people thought. With everything I've been through over the last couple days, what could they really do to hurt my feelings? I did need to talk to my boss though, explain to him that my appearance may be changing somewhat in the future as though it hadn't already!

Upon arriving at work the first thing I needed to do was to discuss certain changes with my boss. Walking into the office I received a few strange looks from the office staff as I walked toward the owners office. Standing outside I knocked three times quietly at the door.

"It's open, come on in." he hollered from behind the closed door.

Great fear flooded through me before I even opened the door! I didn't know what the fuck I was doing! This type of guy didn't look kindly on people like me. I could be beaten severely for just looking like this, or at the very least I could be fired, and I didn't need to be losing jobs right now either. I felt like running away, quitting my job, losing all the perks and benefits that came with employment here, but lack of judgement caused me to stay. Twisting the handle I slowly pushed the door open. There he was sitting at his desk, even sitting he had a powerful presence. Faking confidence I close the door and sat in front of him at his desk. His eyes were burning holes into me, weakening my resolve.

Doug, sat in his chair, his desk hiding his huge belly, one that he'd acquired from drinking far too many beers every evening and even more on the weekends. He was typing with only his index fingers because his fingers were quite large. His hands were rough because he still worked in the field most days. Looking up at me with his deep inset eyes, he stopped everything he was doing. He had started the company twenty years ago. I had been a part of it for ten years so this was a bit of a surprise for him.

" Sir, I feel the need to tell you that my apperance may be changing in the future." I said.

He leaned forward looking keenly into my eyes. it was as though you were looking through me, seeing me for exactly who I was without me even being aware of it.

"What Sam, like hair, make up, and girly fingernails?" he asked.

He didn't look away, even though I could no longer look him in the eye. I came in with confidence and he had figuratively put his boot on my neck. He was in control of the situation and we both knew it.

"Any other changes I should know about? Stand up, come sit right here." He said patting his knee.

I was scared! Petrified, I couldn't move, I couldn't even breathe. He was asking me to sit on his lap! My pulse pounded in my chest, I'm pretty sure he could tell I was mortified!

"Come... now!" He almost yelled.

My Feet moved first. Kicking my legs out I stood up and almost scurried around the desk. I must have looked quite foolish, a grown man with bright pink fingernails, three brand new face piercings, and a shitty makeup job, sitting on his bosses knee.

He placed his hand on my back, I could feel his fingers playing with the clasp at the back of the bra. I wondered to myself if I made the right decision wearing a bra today or not. I felt the latter until he tugged at the waistband of my panties.

"Go lock the door, and strip down to your underwear only." He said calmly.

I knew he was serious because when he said the word 'ONLY', he squeezed my arm quite hard. Getting up I walked to the door and locked it. Unceremoniously, I kicked off my shoes and disrobed leaving only my cupless bra and thong panties. My cock had become slightly engorged, as it was pushing at the thin material at the front of the thong. I stood head dropped, hands clasped tightly in front of me. I was scared. I had no idea what he was going to do, or why I had complied with his demands. He walked around me, almost assessing my body like it were some treasure he had found. Every now and again, he would run his fingers over parts of my exposed flesh. My skin would betray my mind and rise into goosebumps wherever he touched me. Standing directly in front of me, he pinched both of my nipples hard. A whimper escaped my lips as I turned my hips away from him. Then he applied pressure to my shoulders.

Dropping to my knees in front of him, I begin unbuckling his pants. I knew what he wanted without him even uttering a sound. I knew what the requirements were to keep my job. I also felt these were the requirements for me to leave the room safely. So I pulled his cock free from his underwear, and placed my mouth around the head. I began sucking his dick, trying desperately to make him come as fast as possible. Playing with his balls, I knew he was close. Just as they tensed up and started retracting he pulled me up by my armpits, his cock ripped from my lips with an audible popping sound. He pulled me up onto my feet, and he kissed me. Well, more like he stuck his tongue as deep as he could into my mouth. As he was fucking my mouth with his sloppy tongue more or less, as he was walking me toward his desk. I could guess he wanted more than a kiss and a blow when he pushed me face first over the desk, and pulled my thong over my ass cheek.

Standing behind me, I heard Doug spit. Then I felt his wet hand rubbing at my anus. He spit again, and placed the head of his cock at my asshole. As he pushed his cock inside me I let out a small moan. I didn't mean to moan, it just felt good. I didn't want it to feel good, but sometimes your body has a mind of its own. I felt myself pushing back into him. I didn't know why I was pushing back into him, I was slightly repulsed by the fat from his stomach as it touched my upper ass cheeks but my insides were feeling great! My cock became hard and was tensely poking at the front of my panties. I could feel a little wet spot developing right at the head of my dick. The eroticism of it all flooded my mind. Here I was getting fucked in the ass by my fat boss Doug, over his desk, when everyone else in the company was working. When half a dozen women were just on the other side of that wall! He flipped me over, and threw my legs up over his shoulders. His upturned cock pounded my prostate, and caused little spurts of precum to erupt from my penis.

" Cover that thing up girl, I don't want to look at it!" he hoarsly growled at me.

Between moans of pleasure, I cupped my hand over my penis, and tried to hide it from view. He continued pounding my ass as though it were a pussy. Enjoying the fucking so much, I reached out for him, I was pulling him into me when his head fell back and I heard a low guttural growl and he exploded in my ass. I felt shot after shot of cum flow into my anal cavity. If I were a woman, I'd have surely gotten pregnant that day. Pulling out of me he wiped his cock off, did his pants back up and sat back down behind his desk. I pulled my panties back into place and started to get dressed as he began speaking to me.

"Take the rest of the day off." He said. followed by,

"I don't have anything for a person like you out in the field, but I can make a position here in the office if you'd like."

"If you do decide you want to keep your job, make sure you show up to work on Monday in clothing much more fitting to a person like you."

With his last statement, he gestured with both hands, pointing to my whole body. I was still standing there in my bra and panties, clothing in hand, just listening.

"And for gods sake, do something to hide that fucking thing!" He said pointing directly at the wet patch in the front of my panties.

"You are dismissed." He said as he went back to work.

Quietly I put my pants back on, pulled my shirt over my head, and slipped my socks over my bright pink toes and stepped into my shoes. Standing upright, I felt the first glob of sticky cum start making its way out my ass. Opening the door, I began to wonder to myself... where might I be right now if I hadn't put that lovely green teddy on?

Stepping through the door at home, I am greeted by the sounds of sex. I can hear panting, grunting, and Sarah is moaning softly. Walking by Sarah's partially open door, I see a man's back, and her legs in the air. I can see his ass rhythmically pumping like a piston into her. Her little hand is reached around pulling at his thigh. She is pulling him into her. I realize... this is my life now. She fucks whoever she wants, because she doesn't see me as a man. And I fuck whoever she tells me to, because I can't see living without her. I'm fine with that for now. Right now, I want to get this cum cleaned up from my ass, so I strip, and step into the shower.

Maybe ten minutes into my shower, Sarah came into the bathroom accompanied by her friend. He apparently just needed to piss before he left. She wanted to clean up, and to see why her sissy was home so early. She stepped into the shower naked with me. Looking at me she saw I'd tried to do my makeup, and smiled warmly at me.

"Your makeup looks nice, did you have trouble doing it?" She asked.

"Yeah, it's a pain in the ass." I said.

Reaching between her legs, Sarah pulled her fingers away from her pussy and they were https://pokemaster.es/social/bealle-adams/

covered in cum. She saw me eyeing her fingers intently.

"Do you want some sissy?" She asked.

"If it would make you happy... yes please!" I replied.

Then she placed her fingers, soaked in cum right at the base of her clit and said,

"Come suck it clean then!"

Completely abandoning the hot water, I dropped to my knees and put her sticky fingers in my mouth and began sucking them off like it were a little she cock. I could taste her sweet pussy juice, but there was another taste in there... the cum coated my tongue and throat. It taste like the smell of bleach. When she thought her fingers were clean enough, she would drive them back into her hole, to scoop out more cum for me to suck from her fingers. Eventually she stopped having me stuck her fingers and I was allowed to just lick the cum directly from her pussy. I tried my best to get it all, but a few short minutes later, she was grabbing at my hair, pulling my face into her pussy as she had an orgasm. My dick was hard as a rock and I wanted to fuck her right there.

Sissy Awakening Ch. 02

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