Cassie's Sissy Bitch Pt. 01

I was never the most popular boy in around, I was a 21 year old virgin and really did not have any experience with women. I had left home to go to college, and I was just beginning my third year but I never really found a social niche. Even after 2 full years in this college town I still was pretty much without friends and spent nearly all of my time by myself. I was about 5 foot 9 and was pretty skinny for my height at only about 145 pounds, as I could never get into the habit of working out. My hair was chestnut brown and I normally kept it under control but this summer I was working my part time gig from home so I had gotten a little lazy and had it grown out to about my shoulders. If I had wanted to I could have tied it up into a man-bun, but I wasn't really cool enough to pull it off.

But now I was back in town and for the first time I had a one bedroom apartment all to myself. It seemed like the perfect opportunity to start really making some friends and maybe with a bit of luck even meet a girl. But I would need to actually make an effort to get the ball rolling, so the Friday before classes started seemed like a good as time as any to hit the bars and try my luck. I put on a plaid button down shirt, some nice khaki pants, shaved, showered and combed my hair back.

The street with all the college bars was not very far from my apartment (I was as close to campus as I could afford), so it was only a five minute walk, and i entered the first bar probably about 11 pm. The place was packed, but I was able to push my way up to the bar and get myself a beer. There were people shoulder to shoulder and it was so loud that I couldn't really get a word in with anyone. My timidness took over and I spend nearly an hour in the bar standing around, getting pushed about by the sea of people shuffling in and out.

I decided that this wasn't the place so I waltzed out and made my way into the place next door. Unfortunately it was much of the same. Crowds of people all basically yelling. This pattern continued for the next 2 bars as well.

It was getting late and nearing closing time when the crowds finally started to lighten up. I had made absolutely no progress the entire night so I was feeling pretty discouraged and I started to get myself together to head back home and fall asleep. Maybe things wouldn't be any different this year either. But then I saw a girl sitting at the bar.

She had to have been the most beautiful person that I had ever seen in my life. She was wearing a light blue floral sundress that she had hemmed up to the point that I could see the very bottom of her beautiful round ass peaking up beneath the folds. She had a pale completion, with some cute freckles dotted around her rounded cheeks. Her long hair was partially curled, and fell in gorgeous golden rings down to the small of her back. She had piercing blue eyes that looked like the deep sea. I had to go over to her.

As I took my first few steps towards her, my heart sank as another guy, mid twenties by the looks of it, walked up behind her and leaned himself onto the bar. He was definitely out of my weight class, probably 6 foot 3 with some serious definition to his arms. She turned to him and fluttered her eyelashes seeming to reciprocate his approach. I was disappointed but not really surprised. Oh well, I decided I may as well get one more drink before I go and walked up to the bar, probably 5 feet or so to the left of her.

I ordered a beer and the bartender brought it to me as I handed him my card. "No need. She's got you covered." the bartender replied. I stood there staring in confusion for a moment, not really sure what happened. Then I look to my right and I see the tall guy with a sour look on his face walking away, and the girl staring right at me.

"I hope you don't mind I bought you your drink." She said to me in a voice as sweet as honey.

It took another moment for me to register what was going on. I was certainly not used to getting any attention from women, and now this gorgeous specimen just ditched a 10 so she could talk to me. I didn't want to blow it so I collected my thoughts as quickly as I could. "I'm pretty sure I am supposed to be paying for your drinks." I finally said a tad sheepishly.

She stood up and her hips swayed from side to side as she walked over next to me. "If you think that then I guess you don't know me."

"I guess I don't." I replied.

"My name's Cassie." She stated. It was astounding to me how much more confidence she had in herself than I did.

"I'm Mark." I stated as I got a tad distracted as she began to push her D sized breasts out, clearly for me to see.

"Let me see your phone." She said and I handed it to her without skipping a beat. She handed me hers and told me to put my name, phone number and email into her contacts. I obeyed as if I was hypnotized by her words. Once done we swapped our phones back.

"The bar is almost closed" she stated, and leaned in close to my ear and whispered, "Maybe you know somewhere else we can go?" Instantly my erection shot up in my boxers. I tried to adjust to pull it off to the side, but the grin she gave me told me that I wasn't hiding anything.

We wasted no time getting out of the bar and I began to lead her back to my place. We talked as we went back and she let me know she was also 21 entering her third year of college here. She had originally come out to the bars with a few of her girlfriends, but they had all found guys to go home with, which was why she was alone. I wondered how hot her friends must have been for Cassie to be the last one to get picked but I kept that comment to myself.

I unlocked my place and walked inside and she instantly hopped up on me and planted a deep kiss on my lips. Her tongue wasted no time sliding right past mine and deep into my mouth. She was so enthusiastic and I was simply frozen in place. I had never kissed a girl before so the sensation was simply too much for my brain to handle and I shut down. She broke off the kiss and gave laughed. "You don't usually do things like this I'm betting."

"Uhh well no." I stammered. "But I am pretty sure I like it."

"Well good because I have got a some plans for us tonight" she smirked as she looked into my eyes. She was just a few inches shorter than me so with her heels she was actually looking down at me. "Excuse me, I need to use the bathroom."

I pointed her in the direction of the restroom and sat back on the couch wondering if any of this was real or just some insane dream. It definitely did not help when she walked back into the living room wearing absolutely nothing. My eyes nearly popped out of my skull. Her beautiful breasts were perky and round, and her pale skin had absolutely no tan lines. Her ass was round and immaculate.

"Why are you still dressed?" she said as she gave me a slight pout. I did not need to be told twice, and stripped faster than anyone had ever stripped before. She walked over to where I was sitting on the couch and sat on my lap facing me, with her legs straddling mine. My erection was pushing firmly against the front of her pelvis. I had never wanted anything so bad in my entire life.

"Do you want me?" She asked.

"Yes." I replied without breaking eye contact. I could feel the heat of her glistening pussy on my thighs.

"Would you do anything to have me?" She asked me in the same voice as before.

"Absolutely anything" I responded, mesmerized. She leaned into my ear.

"Then I want you to do something really really hot for me." She whispered. I was ready for her to tell me I needed to fuck her brains out.

"Yes Cassie" I said eagerly.

"I want you to go put on my clothes." She said in a monotone sharp voice. It was no longer sensual and soft, but cold and hard. I was again shocked frozen for the third time this evening.

"What?" I said with a confused look on my face.

"You heard me. Go put on my clothes. They are on the bathroom floor." She paused a moment and looked down at my still erect cock. "That's the only way that this night will continue."

I was flabbergasted but I thought about it for a moment. I have basically never had a full conversation with a girl before an hour ago but now I'm this close to losing my virginity. I of course would have to leave this bit out whenever I talk about my first time but as long as nobody ever found out Id pretty much go to hell and back in order to fuck Cassie right now. "Uhh ok, but it seems pretty embarrassing" I said finally.

"It's just us here, now stop wasting time" she snapped back.

I got up from the couch and wandered into the bathroom where she had peeled off all her clothes. I found her silky sky blue panties and held them up to the light. I could see a slight wet spot where her pussy had been dripping on them. I paused for just a second while I second guessed whether or not I was going to go through with it. Eventually I decided that if she was a freak whatever, I'm in no position to be turning down any opportunity to get laid at this point, and slid the panties up my legs.

The silk felt soft on my cock and it pulsed when the panties rubbed up and over the head. I nearly felt light headed as there probably wasn't enough blood left for my brain. I put the bra on and clasped it behind my back. The big empty cups swung off my flat chest and I reached over and pulled some toilet paper off of the roll and shoved it down into the cavity. When in Rome I thought to myself. I pulled the sundress over my head and it fell down gracefully over my body. It was short on Cassie but on my it was so short that it didn't even begin to hide my raging boner. I picked up the heels and shoved my feet into them. It was a tight fit, and I'm sure I was stretching them out but that what she asked me to do so its not on me if her shoes get ruined. I caught a glimpse of myself in the mirror and had to take a quick double take. I still looked like myself, but there was certainly a sexy quality to how I looked dressed up in Cassie's things. I tasseled my hair a bit and it flowed down nearly to my shoulders, still a boys haircut but something just a touch more feminine. I was ready to finally know what its like to get my dick wet, as I turned and walked out of the bathroom, a bit wobbly on the heels.

When I walked out I didn't fully understand what was going on. Cassie was back to being fully dressed, in clothes that it looks like she had taken out of my dresser and was standing next to the door. I once again froze while my brain tried to make heads or tails of what was happening. Cassie didn't waste a second. She pulled a nice camera out of her purse lightning fast and there were 3 quick flashes from the as I stared directly into the lens like a deer in headlights. "Smile sissy bitch!" She laughed at me while opening the door and slipping out into the night.