Introspection

I pulled the black Chevy Suburban over to United arrivals lane at Bozeman Airport. I was late and she was already outside waiting with her two large brown suitcases and a smaller black one. Jesus, she brought a lot of gear for a short ski weekend. She was also shivering. Maddy was always cold. Her tall, skinny body and low body fat made her an easy target for winter. I shook my head and smiled at her. She looked fantastic. Tight jeans, white sweater, brown boots with her long hair flowing down to her mid back. "Punishment" I immediately thought in my head. She knows she is always to greet me in a short skirt, no panties and slutty high heel shoes. I got out and kissed her roughly while my right hand groped her tight little ass. "Baby, you are in so much trouble" I announced. She gave a fake half smile and abruptly jumped in the front passenger seat. I took her bags and threw them in backseat and assumed the driver's position. Lenny Kravitz belted "American Woman" as we started our long drive to my ski chalet in Whitefish.

Maddy was noticeabley quiet during our drive through beautiful big sky country. I joked with her and teased: "What's the matter baby? You worried about your hard spanking later? I promise to be kind of gentle." I rested my hand and forearm on her thigh and started to massage her pussy through her jeans.

"Pull over" she suddenly instructed.

"Here?" I inquired looking around at the farmland and the remote dirt pull off.

"Here!"

I brought the suburban to a stop. Maddy removed the keys from the ignition and dropped them on the floorboard at her feet.

"What the fuck Maddy? What has gotten into you?" I was starting to get irritated and annoyed. We still had quite a drive in front of us. And I never have time for drama.

She grabbed my face with both of her slender hands and looked deep. "You know that computer you lent me for my research" she asked without a hint of a smile.

I stammered out a faint "yes" immediately thinking about all my emails to previous little cumsluts I used and abused. "Shit - she is jealous and I am going to have to explain my previous two timing ways" I thought to myself.

"Well, I was doing a little forensics one night wondering what I would find on your machine. Your google search history you thought you deleted was so ridiculously easy for me to pull up." Oh my. Oh no. Maddy was always resourceful and I knew exactly what she had found. This was bad. I started to stammer our a bullshit excuse.

"Stop. Baby, just stop. You are a wonderful lover, an amazing mentor and a great friend. But you are also a little sissy cumslut whore that needs to be put in her proper sub slut place. And it's going to happen this weekend. Either that or you can immediately drive me back to the fucking airport." Her steel eyes told me she wasn't even remotely kidding.

"Baby..." I protested.

"Don't even fucking start with me" she said as she started to pull off her jeans and lower her panties. I was so confused. She started to rub her pussy. "Fuck me Jack. Fuck me hard and fill my pussy up with your hot cream." My head was reeling. First my girlfriend calls me out for being a closet sissy cockslut

and now she wants my manhood and seed in her wet cunt. I could smell her sweet scent and I started to arouse despite my mental limbo.

Her tone suddenly changed. "Look, you have five minutes to deposit your load in me and trust me you should, as it's the only time your cock will be anywhere near my sweet pussy all weekend."

"Baby, you know you are going to need more pussy pounding than that" I responded laughing starting to feel I could gain hand once again.

"Oh, I plan to get plenty of pussy pounding by big cock this weekend sweetheart. Just not yours."

"Maddy! Be fair".

"Four minutes and fifteen seconds" was her only response.

I hustled my pants down and climbed on top of her. I was diamond cutting hard and entered her fully in one full thrust. I started to pump and own-my-woman again but she pushed back against my chest and started to close her thighs. "Baby just rest your cock inside me and let me tell you about the start of our weekend. You are going to fill my pussy up with your seed. Then you are going to pull up my panties. Your last cum will be a tasty creampie treat for Jackie later tonight. Then you are going to take my little black suitcase and pull out the panties, dress, stockings, heels and wig out of the main compartment. And get yourself completely dressed. Finally, you will throw your clothes and shoes in the ditch next to the car and you will never see them again."

"Baby"... I begged. We had kidded about Jackie in the past but it was always innocent banter fun. She instantly pushed me away and closed her thighs and pushed her powerful legs back into me. She almost drove me into the front windshield. This was Maddy at her most resolute. "You do it or I am going back to San Francisco and you will never see me again."

"Fine" I relented knowing I needed to get my rocks off.

"Now fuck me" she demanded. I started to thrust and both of us started moaning and moving together. I started to get my groove going and I could feel her body and breath respond. "Thirty seconds" Maddy abruptly instructed.

I immediately released into her pussy. I drove my hard tool in as deep as possible and just rested. I figured I was due a "love you" or "that was amazing." Nothing. She pointed for me to get off of her.

"Suitcase" was her only word as she pointed to the backseat. At this point it was pitch dark outside. I knew Maddy well enough to know she was serious but I had never seen this side of her. I climbed into the back seat and opened the suitcase. I pulled out black lace G string panties, black thigh high stockings, garter belt, blonde bob wig and a black and white striped short cocktail dress. And last my definitely not least, very slutty fuck me black pumps with little ankle straps. I put the backseats down and struggled mightily to get into my new weekend attire get up. The entire time Maddy casually texted and typed on her phone. She only looked back a couple of times. There was never even a hint of a smile. I finally buckled the shoes and announced myself complete.

Maddy jumped into the front seat and ordered me to sit in the passenger seat. She took out her purse and pulled down the passenger visor mirror and started to apply a little make up to my face. Not a lot. Just a little blush, eye liner and some deep ruby red lipstick. "God, you have such an amazing cocksucking mouth" she exclaimed. "I simply can't wait to see it in full action this weekend."

Suddenly I saw her face turn red and her lips purse. She didn't say anything. She just pointed to my clothes still sitting in the back seat.

"Baby..." I started to try and reason with her.

"You fucking little disobedient disrespectful slut - recline the seat all the way and lie flat face down!" I knew she was super pissed. This was not an act. I did as commanded. "Pull your panties down and lift your dress." I did as directed and immediately got goose bumps. I heard her fumbling with her purse. Suddenly, I felt red hot intense pain on my bare vulnerable ass. I knew it was her antique wooden hair brush assaulting my poor bottom. The violent spanking seemed to go on forever. At least thirty hard whacks. I kicked my high heels. I squirmed. I begged. I was shaking and truly close to tears.

"Jackie." She whispered in my ear as she finally stopped the beating. "Jackie, I am not fucking around this weekend. Get that through your dumb blonde, little cocksucking brain or else your ass is going to be striped all weekend by me and a variety of my guests.

And if you disappoint me in front of my new friends the ass beating we will deliver will make this one seems like child's play. Do you understand me?"

"Yes, goddess" I whimpered.

"Will you be an appropriate respectful little slut and do whatever I ask without hesitation?"

"Yes, goddess."

"Have you been fantasizing about sucking big thick cock and getting yourself fucked silly by big alpha males?"

"Yes, goddess." I couldn't believe what was coming out of my mouth. It was like an out of body experience.

"Good girl" she cooed as she rubbed my soon to be bruised tush.

I then felt her start to write with what felt like a Sharpie on my sore butt. I had no idea what she was writing but at that point it just didn't matter. I was truly broken. I had just received a brutal spanking and confessed my darkest fantasies to my beautiful girlfriend. I felt warm lube massaged on my puckered asshole. Maddy gently fingered me as I bucked my hips and pushed back against her hand. I craved more penetration and she knew it. She chuckled as she withdrew her finger. Next a much bigger intruder dove deep into my wanton ass pussy. I gasped at the sudden pain and fullness. I knew from experience it was a large anal plug. Then every thing melted and my world changed. I felt truly feminine and slutty. My body relaxed. My mind eased. I rolled down the window and threw my clothes and shoes out. I buckled my seatbelt. Maddy finally smiled and gave me a huge kiss. She laughed and winked. It warmed me. Maddy put the key in ignition and started to drive. To who knows where...