Sissification

Copyright Yuki 2011. This is my story, and it shall not be posted anywhere without my permission.

*

I rested my head on my arm as I sat on the torn bar stool. It was an old building, the bar. To the regulars of this place, like myself, it was simply known as 'The Pub'. Tonight was no different than any other. I ordered my usual club soda and water, some guys from work ordered their beers. The background noise was made up of billiards balls cracking against each other, men laughing and cheering, loud talking, sports blaring from the TVs around the place, and some music from the karaoke machine. My head was spinning, another long day in a small cubicle which does absolute wonders on adding stress to my body and mind.

Tonight, I felt a bit more social than usual. I joined in on a game of pool. We shot ball after ball, missing every shot. They were drunk, I was just a bad player. My turn came up, and just as I was about to pull the cue back, a new sound filled the pub. "Hey cutie, come here often?" A slim woman, probably in her mid to late 20s was leaning on the far end of the pool table.

I was a bit shocked, so as such, I didn't -- Or couldn't, rather -- think of anything to say back. The bartender saved my ass, "Hey Karin. What brings you here on such an average night?" She walked over to the bar and took a seat on the stool I had sat in earlier. They began talking. I looked around to see if the guys had seen that display of failure on my end. One was passed out in the corner, another was staring at me. He was standing behind me, leaning up against the wall.

"Dude, you blew it. You might've even got laid, bro." As he ended his sentence, another man came out of the bathroom. I think his name was John, but I'm terrible with names.

"Wait, who'd he miss?"

"That woman at the bar. Freakin' hot."

John paused a bit before speaking. He went a bit slack-jawed to say the least. "Oh man, that's 'The Vix'. Don't get involved with her, man. I've heard some awful shit about her."

Now, at this, I was skeptical. "Why? What have you heard?"

"Like, she like kills men after having sex with them..."

This, of course, went ignored. I laughed at him a bit before walking up to the bar and taking the stool next to her. "Hey, miss."

"You can speak now, I'm glad." She laughed a little.

"Heh, yeah. Sorry about that, it's not often a woman as beautiful as you comes into this old place." Now, when I say 'beautiful', I mean 'drop-dead-gorgeous'. Her hair was a light brown, lightly curled, hung behind her trim shoulders and down to her mid-back. Her eyes were a hazel, and he lips were pink. She was wearing a loose black dress, V-cut and open in the back.

"You're sweet. Do you have a name?"

"Yeah, friends just call me Dog."

She giggled, "How fitting. I'm Karin."

"Fitting? How so?"

"Oh, nothing. You just seem like the loyal type." She giggled to herself again. I, however, took that was an ego boost.

"Well, Karin, care to continue this conversation elsewhere? My place, perhaps?"

Her lips curled into a seductive smile, "How about mine? It's just up the road."

"Anything's fine with me, babe." We started heading toward the doors, I glanced back at the guys, they just stared at me as I lightly pounded my chest with my fist.

She took my hand in hers and led me up the block and across the street. "Here we are. Told you it was close."

"Well you certainly weren't kidding." Her place was a small house, looked to be two floors.

"Come on!" She pulled my arm and walked up the stone walkway and into the front door. We immediately headed to the left, to the staircase right next to the entryway. It headed to the second floor, leading to a balcony where three doors were visible. Bedrooms and a bathroom, probably. When we reached the top, we took another immediate left into a door right next to the stairs. It led into a bedroom with a large bed and a vanity mirror. There was a door in this room, master bathroom. Next to that door, however, were two brown paper bags. They seemed out of place. "Mind if I get a little more comfortable?"

"Not at all. Take your time." I winked as she made her way to the bathroom, picking up one of the bags. I was already liking where this was going. She closed the door, and I sat on the bed, taking off my tie and unbuttoning my shirt about half way. A few minutes passed, and she came out with a bath robe on. She bent down and picked up the other bag. As she stood in the doorway to the bathroom, she opened the second bag, looking into it and smiling. She threw it on the bed. "Put those on. I'll be back in a minute to check on you."

"Uh... Alright." I wondered what could be in the bags, but I figured I could put up with whatever it was. I was wrong. As I turned the bag so it was facing me, I saw a pink thong, a skirt, and a small shirt of some kind. There was also make-up and other things I didn't recognize. "I think you gave me the wrong bag... These are women's clothing."

"No, I didn't give you the wrong one. Put those on. I'll help you with the rest in a little bit."

Now, my mind was racing, I wasn't really sure what I was doing. I certainly wasn't even sure if I should go along with this or make a run for it. I figured my dry spell had been going on long enough. I'd just make up some story to tell the guys later; no way I was going to tell them the truth. I took my clothes off and laid them in a pile on the bed. I picked up the underwear from the bag; a black thong. I slipped my feet into it and pulled it up my legs. This type of behaviour would have seemed wrong, but my now-hard cock was saying otherwise. The fabric felt smooth as it slid along my skin. I tucked my shaft into the small triangle and out a leg hole. Then I grabbed the skirt. It was pink and black plaid with black frills. At first, I thought I'd have troubles fitting into it, but I managed to get it around my waist and zipped up. It was a bit snug.

I heard a knock on the door, "How's it going in there?"

"F-fine..."

"Need any help?" She sounded eager.

"N-no..." I stammered along "I think I've got this..."

Next up was the shirt. I picked it up and held it out to see what I was getting into. It was a belly shirt, one button in the front. I sighed and slipped one arm in the sleeve hole, then the next. I pulled the shirt together and buttoned it. Again, a bit snug, but not enough that it wasn't possible. I looked in the bag again, the only thing I knew how to put on that was left was a pair of stockings. They were pink and tight mesh. I slid them up my legs, and to my surprise got me even more excited. It felt smooth and luxurious.

"I... I don't know how to do the rest of it..."

She opened the door slowly, as if expecting disappointment. "Oh, you are just adorable!" She smiled at me, looking me up and down. "You've got no make-up on, deary."

"It's not like I've done this before..."

"Oh no, no. It's a good thing! That means I can do it for you!" She reached into the bag and pulled out a stick of something. She twisted the bottom, it was a pink lipstick. She rubbed it lightly on my bottom lip, all the way across. "Now pinch your lips together." I did as she said. "Perfect! Let's see... now we need some blush." She grabbed a powder kit from the bag. She dipped the brush in a reddish coloured powered and brushed my cheeks with it. As she continued this, I got even more excited. I'm not sure why, but it felt nice to be pampered like this.

She grabbed another stick, twisted the cap off to reveal a smaller stick in some coloured, thick liquid. "Hold out your hands." Again, I did as she said. She held my hand in hers, painting my nails with a bright pink paint. One by one, she made her way along all of my fingers. "Now don't touch anything with them. Close your eyes, and don't flinch." I heard the bag ruffling again and a moment after, I felt a brush along my eyelids, then another brush on my eyelashes.

"You're missing something... What is it... Stand up, dear." I did so. She looked me up and down, and then down and up. She stopped at the top of my head. "You need a wig!" She made her way over to her vanity mirror, below it was a dresser. She reached in a dresser drawer and pulled out three wigs. A blonde, a brunette, and a red one. I stood there in the middle of her room as she held the wigs up, imagining me in each of them. She turned down the red first. Then the brunette. "You're going to be a blonde."

I didn't mind the thought of that. I did like blondes. "Can I see... what you've done to me?"

"Oh, of course! Should have asked sooner, cutie." We walked, my hand in hers, to the bathroom. She still had on her bathrobe, I actually hadn't thought about it much. I looked in the mirror and my jaw utterly fell. Hard. "This... can't be me." In the mirror stood a woman, one that I would have been happy to see at the bar. The change was astonishing. I didn't even recognize myself. She pushed my jaw back into place and led me to the bed and sat me down. She let go of my hand and got on her knees.

She lifted my skirt, "Oh, someone's enjoying this..." Before I could even respond, she began licking the head of my swollen cock. Her tongue seemed to dance up and down my shaft, teasing and toying with me. Then, without any warning, she stood up.

"Why'd you stop?"

"I didn't get you dressed up for nothing." She undid the tie holding the robe closed and let the clothing fall. Before seeing anything, I started to speak, "You look gorgeou-..." Something caught my eye. "W-what is that?" Underneath, she wore a black lacy bra, matching stockings, and a black strapon.

"I'm pretty sure you know what it is, and I'm pretty sure you know what it's for."

"Oh, no. I did not sign up for this one." I started to get up, but she pushed me down onto my back.

"You're not going anywhere, deary." Beads of sweat formed on my forehead. For the first time in a long while, I was scared. "Now, turn over and get on your hands and knees. I want you to suck this big piece of rubber off." My fear turned into willingness, not intentionally. More like I was too scared to say no or disobey. I did as she demanded and began licking skeptically at the black toy. "Good girl..."

Soon enough, she grabbed the back of my head, pulling my hair and pushing my mouth deep onto it. I started choking, she just continued bobbing my head on it. She finally released her grip and I freed my mouth of the gag. As I choked for air, she moved behind me. I felt the moist rubber resting on my lower back and bottom, and a cold liquid forming around it. As I look to the side, only to see a girl on her knees and another behind her pouring a small bottle of lubricant on the strap-on. I couldn't help it, the sheer sight of this would turn any man on beyond a breaking point. Just as she positioned the tip of the shaft at my virgin hole, I lowered my chest onto the bed, sticking my round ass up even more. She grinned, and I couldn't resist anymore. I wanted it, I wanted my release. She forced the tip in, and even with all the lube she had layered on, it still took a bit of effort to slide in. To her surprise, as soon as the tip was all the way in, I pushed back to meet her initial thrust. Almost the entire length of the shaft was buried deep inside me. I cried out in pain and pleasure.

"Now, now, my pet. Let's not get greedy." She slapped my left cheek and began slowly gliding the hard shaft in and out of me. She soon picked up pace and was pounding my bum relentlessly. With each thrust, my dangling cock would brush up against the skirt as it moved forward with my body. The fabric's gentle embrace sent chills up my spine. We had only just started and I was near climax already. Then, as if to enforce her control over me, she stopped. She pulled out and denied me the satisfaction of re-entry. She went over to her dresser and pulled out a satin pair of panties, "Get on your back, ass on the edge of the bed."

"Yes, mistress." the words passed my lips without a second thought as I shifted my body as she demanded.

"You're picking up things on your own. I like that. For that, I'll let you have this treat." She grabbed a second pair of panties, black cotton. Then she kneeled on the floor between my legs, positioned to enter once more. She held the cotton panties in both hands, rolled up, and smothered my mouth with it, "Hold it between your teeth like a good girl. You'll need something to bite down on for this next part." With that, she took the tan satins in one hand and wrapped my cock in it. My body shuddered and chill after chill went through my entire being. She thrust her cock deep into me once more, this time stroking my shaft with her smooth panties. She was right; I definitely needed to bite on something. I bit down hard on the cottons as she stroked me to orgasm. My cum shot upward at first, but then she aimed it at me for the rest of the waves of hot seed. They streamed on my stomach, chest, neck, face, and in my wig. "You got my clothes all dirty..." She paused, "take off the top and suck out your cum. Clean up your mess."

"Y-yes, mistress." I undid the button in the front and squirmed to get my arms out while on my back. I manged to get the shirt off and did as she commanded once more. The smell of my own fluids was strong; a salty, bitter smell. I licked at the wet spots, cringing at the initial flavour.

"Keep going." I obeyed without hesitation, pressing my lips up to the biggest wet spot and sucking it out. The flavour was much better when there was more of it to taste. I took a big sniff of her clothes with my seed, and the smell alone made me hit my second climax. I guess the ceaseless pounding in my asshole probably helped a bit, but the intoxicating aroma was just overwhelming. "A second already? You must have been pretty pent up, deary."

I just nodded and proceeded to lick up more of my cum. As she continued thrusting, my body seemed to slide up and down along the bed, my cock bobbing with my body. I couldn't believe I was still hard after that, but sure enough, I was. Again, as if out of cruelty, she stopped suddenly, pulling quickly out of my ass.

Almost as soon as she was out, she undid the clip on her waist holding the strap-on in place. It fell to the floor as she stood up. "Time to please me, my pet." She grinned, "I want you to eat my ass out." I was hesitant at this, another thing I'd never done before... "Maybe I wasn't clear. Get over here and lick my back hole. Now." Once more, fear overtook thought, and I did as she asked. I positioned myself behind her as she leaned over, holding onto the edge of the bed. I spread her cheeks apart and dove my tongue straight in. Now, I can't say the taste was bad, but it certainly wasn't great. It did manage to arouse me even more still. "Mm, stick your tongue deeper. It feels so good..." I pressed my face to her ass, delving my tongue in as deep as it would go. She moaned loudly and pushed back against me. And then, just when I start enjoying it, she stops, pulling her body forward, freeing herself from my face. "Your cock. My ass. Now."

This one I was less disappointed about. It took me no second warning to get myself in position. As she reached out to get the bottle of lube, I pressed my cock all the way in with one thrust. She cried out, but it didn't sound as if she minded much. I continued thrusting in and out as she began playing with her pussy. She would occasionally reach back and tickle my balls while I was still going slow, but that ended when I sped up and she needed to grip the bed with both hands to keep herself steady. "Good girl, fuck me harder! Fuck my ass!" she cried out over and over again.

Again, I took a look in the mirror as I thrust deep into this woman. I still had my wig, skirt, and stockings on, and I looked like a dickgirl, pounding a defenseless woman's rear. With each thrust, her breasts bounced like my dick had earlier. My mind snapped back to the actions at hand with one utterance, "I'm close, fuck me faster~. I want you to cum in my ass!"

I had nothing holding me back, and a few pounds later, I shot the first wave. My body shuttered as I continued fucking her. She screamed out in orgasm, I kept thrusting through the sensitivity of my cock, and my seed flooded her tight hole.

We both gasped for breath as the final wave of seed filled her up and began dripping out with my cock still in place. I pulled out and the cum poured out onto the floor. "Eat my ass. I want you to drink up your own cum!"

"Yes, m-mistress..." I stuck my tongue into her ass once more, scooping out my thick cum and swallowing it. My cock twitched with each gulp. After I had got all I could, she stood up and wiped the sweat from her forehead.

"You made a lovely pet, my dear."

"Thank you, mistress." I smiled, my make-up smeared and mixed in with cum on my face.

"You can use my bathroom to clean up, and you can keep the clothes... you deserve them."

---------------------------------------

The next morning, I took my usual seat in my cubicle at work when one of my coworkers walked by. "Hey man, what happened last night?"

"Nothing special." I smiled to myself.

"Oh, that's co-... Are your nails painted pink?"

My mind went blank, but I just laughed awkwardly and he walked away.