Sissy New Year Ch. 01

The year 2012 was a crazy year for me. It had an end and a beginning, most things do. Typically when I think of any year I don't think about the start and the end. Somehow, the events that happened to me that year seemed to line up perfectly and I don't know why...

I was at a New Year's Eve party a friend brought me to, it was already the New Year and the party just seemed to have gotten crazier. Most were drunk and just finding anyone to make out with, people were playing beer pong, some doing shots, and others pushing each other in the swimming pool. I had retired to the couch, I was sipping on a Miller Light alone in the living room. Observing from afar just seemed to be the smart decision right now.

As I was looking around the room I spotted a beautiful older woman. She looked to be in her late forties and was wearing jeans and a t-shirt. I was surprised, everyone here was in there twenties. I was twenty-five myself and had recently graduated from the University of Miami. I was an assistant chemist and worked in a lab nearby.

Our eyes met across the room. I looked away immediately, I must have been staring. I tried to casually drink me beer and look at the ground. I looked up and saw the woman walking over in my direction.

"Hi! What are you doing over here by yourself?" a voice asked.

I looked up to see the woman. I know I was sitting but she was awfully tall, maybe 6'0. I was only 5'6, she towered over me.

"I'm just... relaxing," I thought out loud.

"That's a funny thing to do at a party," she laughed out.

She was very intimidating, especially being older. She sat next to me on the couch, she was very close.

"So, do you go to many parties?" she asked.

"N-not really that much," I said.

"Uh-huh, how old are you?"

"T-twenty five years old,"

"Do you get out much?" she asked.

"No, I mean y-yes, really only sometimes," I said.

"Oh, okay. Are you single?" she said.

"Yes! I mean y-yeah I'm single,"

"What's your name?" she questioned.

"Umm it's just Chris," I said.

"Well just Chris, do you mind grabbing me a glass of wine?" she asked.

"Yes! Of course!" I said.

I jumped up and headed over to where the drinks were at. My friend was there mixing vodka with some soda.

"Having fun Chris?" he asked.

"Yeah just chatting with people, how about you Ryan?" I said.

Ryan turned his head toward the older woman waiting for me.

"You're chatting with her?" he inquired.

"Yeah, she just sat next to me." I said.

"Be careful man, she owns this big ass place. Her name is Misty and she throws parties like this all the time," Ryan said.

"Oh, how come?" I requested.

"I don't know, they're always fun so I come. Some say she throws these parties to pick up young guys," he said with a shit eating grin.

"Wow, I'm sure that's her plan," I said, pouring a glass of wine and grabbing a beer for myself.

"Whatever man, I'm just glad you're doing something else instead of playing COD at home." Ryan said.

I went back to the couch and sat next to Misty. I handed her the glass of wine.

"Thank you very much Chris," she said.

"No problem ma'am," I said.

"I like your attitude Chris," she smirked.

"T-thank you," I blushed.

She crossed her leg over her other. Her toe nails were painted a dark red and matched her heels. I could see her leg a little through the bottom of her jeans, it looked very muscular. I checked her out a little more and noticed she was very toned all over. I looked up at her face and could tell she noticed my little look over.

"How about instead of you undressing me with your eyes, we go to my room?" she asked.

"S-s-sure!" I said nervously.

She stood up and I copied. She grabbed my hand very firmly and led me up the stairs. We went down a hallway and she grabbed a key from her jean pocket. She unlocked the double doors at the end of the hallway and opened up the doors.

It was a large room with a big bathroom attached onto the side, a large king size bed in the middle with maroon sheets, and art work all over the wall. There was a love seat off to the side and a couple book shelves a dressers. The room was very fancy.

Misty went over and sat at the end of the bed.

"My feet are sore, take off my high heels," she demanded.

I got to my knees and removed them as efficiently as I could.

"We'll work on your technique later," she commented. "Since my feet are sore you best massage them."

I gently caressed her perfect feet, I started with the right one and put pressure on her toes. My hand worked it all over. I moved over to the left one and gave it the same loving treatment.

"How about you use your mouth now dear," she said.

"O-o-of c-course!" I stumbled out.

I only had a few sexual experiences, not many like this! I started with the left this time and started sucking on her toes, long and hard on each one. I went up and down her soles and switched to the right to the same. I my tongue would start to dry up as the flavor of her foot settled in. Her feet did not smell good or taste good, they tasted like sand. Yet I loved kneeling below her and licking her raunchy smelling feet. She stared down at me from above with a mischievous smile.

"You've got a good start boy" she laughed. "Now how about we switch it up a little."

She started to adjust herself and in the process lethargically rubbed her foot across my crouch. My cock twitched as time seem to slow a little.

"Lay on the bed, right in the middle," she commanded sternly.

I got up to do her biding. I laid right in the middle of the giant bed. She turned around and crawled over me. She beamed down at me with intent in her eye. Misty's face lowered and she started to suck on my neck. I moaned softly, her hand traveled down to my cock. Her hand was in my pants squeezing and caressing my dick.

I could feel my cock twitch and pre cum leak. She started working my neck really hard, it almost started to hurt. I was so horny, hard, and excited everything felt good. She rubbed and squeezed faster, I couldn't take it anymore.

I felt my dick tingle, my balls tighten, my toes curl, and then pressure build up. I felt cum gush out of my dick faster then it ever had. I didn't know one of the moments that would define my year was just about to happen though...

Misty squeezed every drop of cum out of my dick into her right hand. The hand on my dick kept going and it hurt, post orgasm sensitivity. I tensed and cringed. She kept jerking on my prick.

I gasped, "M-m-Misty! Could y-y-you please s-stop!"

She leered down at me and kept jerking my dick. "I'll stop, only if you eat this cum."

Her right hand was now by my mouth and my dick felt so uncomfortable.

"P-please stop!" I begged. "I don't w-want to e-e-eat my cum!"

"It's that or I continue, better hurry up slut!" she growled.

I reluctantly, but swiftly, licked up the cum off her hand. My diet wasn't pineapple, it showed. My cum tasted so awful. My face cringed and Misty laughed. My eyes closed as I felt disgusted with myself. Before I could do anything, I felt metal slide down on my dick. Something tightened and I heard a click.

"That's better now," Misty said.

I looked down to see some metal cage over my dick, it was locked with a tiny padlock. My dick twitched in it.

"Well, don't stare forever," Misty laughed. "Better get use to it slave!"

She turned and sat on my face.

"Eat my pussy bitch!" she commanded once more.

I really didn't have many options and started servicing her. I flattened my tongue and went up and down here pussy lips. They were thick and tight, I couldn't explain it, but she tasted old. I worked my tongue around her lips and licked inside. I sucked all over and flicked her clit with my tongue.

"Ohhhh!" she moaned.

Her ass started to grind on my face. Her anus seemed to rest on my nose now and didn't smell too fresh. The smell from her pussy and ass was intoxicating. My dick struggled against the cage and I squirmed. Her ass cheeks held me firmly and place and I kept going. Misty started to tense up.

"OHHH that's good slave!" she started to tremble. "OHHH I"M CUMMING!"

Her juiced flowed in my nose and mouth. I lapped up what I could, the rest was on my face.

"Oh, now work on my asshole," she breathed out.

Her ass relocated on my mouth and I continued my service. How I ended up like this confused me. I started to rim her out and stick my tongue up her dirty anus. It almost tasted like she didn't wipe. I kept on and made sure to work my tongue around.

"Wow, you're pretty good for a young boy!" Misty said.

I kept going and her click away at her phone. Her ass started to bounce slightly on my face. My tongue was deep in her ass at the moment, and I felt my air being cut of every time her ass landed down on my face.

She turned around finally and I breathed deeply. As I did so, she spit in my mouth and laughed.

"You're definitely a keeper," she laughed out.

As I gasped, and tried not to choke on spit, she grabbed one of my wrists and attached it to a cuff. She got ahold of my other wrist, twisted me over, and cuffed my other hand. She laid on the bed, wear I was in the middle, and laid on her stomach.

"Well, I'm going to go to sleep. You better lick my ass to sleep slut!" she barked.

My wrists were cuffed in a way that my arms were near the side of the bed. I couldn't move them, instead I rested my face on Misty's ass crack and went back to work.

"Better get some sleep when you're done, you have a long day tomorrow," Misty said.

I don't know what she had planned but my dick hurt, it felt heavy now, and mouth tasted terrible. My wrists ached as I licked her asshole for another hour, just before finally falling asleep in Misty's ass.