Everyone has had some sort of concept of how they thought their life was going to be after high school. It’s funny how fast things spiral and change. At least that is something I could say of my life. My name is Cassie. In high school I was a popular preppy school girl. Unlike the Hollywood concept of a mean blonde white girl, I think I was always open minded and kind with the students around me. After all, we were all growing up in a new era in which it wasn’t uncommon to have a friend or family member who was different. I would say I was definitely in a privileged spot in high school though. I always dressed nice and had the body to get all the attention from the boys, did all my school work, was nominated for prom queen. I was pretty much a perfect girl goodie two shoes.
I would say my life started when I got to college. I went to college in Chicago which I didn’t think was that crazy compared to many of my friends and family who went to the farthest parts of the state or even across country. My boyfriend had gone to SIU, and I knew I was going to miss him very dearly. There are definitely signs in high school that could have predicted how he was going to end up during college. He had gotten a scholarship for football and he had been pretty neglectful of me. He always had an excuse of course. He was at morning practice, afternoon practice, he had to stay after class… was in a group project… at first I didn’t think too much of it because sometimes I got busy too. However he was always being tagged at parties doing stupid things.
At first college life had been pretty lonely. My friends had gone to other colleges and like me took their school work very seriously. We really only had time to talk to one another through FaceTime during the weekends. Summer had gone and fall had settled in. I remember the leaves and the breeze I felt everyday walking by the sidewalks along the lake from my dorm to school. Solitude was something I was slowly but surely getting used to. The North side of Chicago was very beautiful but unique in its culture. The bars and restaurants had their own atmosphere. Living in the upper north side of Chicago things were calmer which I really enjoyed. Sometimes I’d go for walks away from the lake to explore the city. There was this lesbian bar I would walk by that looked so quaint and quite. Nothing at all like Wriglyville with the obnoxious atmosphere. There seemed to be some a level of calmness and happiness walking by that bar where the wind blew the leaves and you could smell the leaves and the musky smell of the bars. So many smells, yet it all seemed like one. I wanted to be happy. I was getting depressed being away from home, my friends, my bf.
One night while writing an essay, I was checking up on my bf and having my fb on another tab on the laptop. Everytime I did my homework I always new it was a bad idea to be on social media. Nothing good ever comes from it. Despite this I feel like we have this urge to connect even when we really aren’t connecting. My bf hadn’t talked to
Me in a few days so I kept on texting him. I felt like a crazy girl texting someone constantly only to see my own texts. It felt as though we weren’t even dating and I was some kind of crazy girl trying to get his attention. I suddenly get a notification on FB saying that my bf was posted in some pictures. I see a bunch of pictures of him at a frat party with him making out with a bunch of girls. I guess they were playing some kind of drinking game.
I was hurt. I felt worthless and discarded. I had been very loyal and affectionate with him. I couldn’t finish my essay… I couldn’t think. I couldn’t sleep. I of course wrote a bunch of texts demanding for him to call me back. I had cried the whole night. The next morning my face was swollen with the sadness and anger from the night before. He was my first love. I remember how excited I was when he picked me up for the Spring Dance sophomore year. He helped me pick out my dress and I liked him so much I wore a dress that showed more cleavage and leg than I was used to. But I remember how we looked like that one couple that would last forever… all those moments a young girl has of innocent love just fluttered away from my heart as I sank into despair. It wasn’t too long ago that I had given myself to him and we held each other’s hands talking about the journey we were going to
Go through together into adulthood. It was all gone. The next morning he called me back. I had tears roll down my eyes when I picked up my phone, but I was angry. I don’t remember what he said exactly, I just remember my anger. He said something along the lines of what the hell is wrong with me, I’m fucking crazy, I don’t respect what he has to go through to be where he is, all of a sudden I cut him off and I told him we were done. Which he interestingly turned around on me. That I was looking for something to break up over. As though I was planning it out, and I was probably cheating on him. It ended with him saying I was a fucking whore, and silence… My anger and sadness probably didn’t disappear like it felt it did. However I did feel pretty relieved. All that stress and anxiety felt cut from my life the moment he hung up. It did feel like a new start. I wasn’t sad or angry. I just didn’t know what to do.
It was that Friday I decided to leave my comfort zone. I’m not sure what really motivated me that night. It was Friday night, and that’s usually where the girls dress up and line up to go to the bars and use the L. Through my eyes I never understood the motivation that other girls had to put on bad makeup, wear something so skimpy and line up to something. They just seemed like a line of cattle. Their heads constantly moving left and right due to self consciousness. After Class i showered, cleaned myself in the right areas. Lol. Dried my hair. Put my make up nicely and chose my outfit. As I said before I wasn’t really sure about my motivation. But in a way maybe I wanted to get back at him, or maybe I wanted someone to want me and take me. I wanted to belong and be loved… too much thinking. But I wore my cutest marine blue matching lingerie, picked out a plaid pencil skirt which was black, white and several colors of gray. My legs looked amazing, and when I looked in the mirror I couldn’t help but feel somewhat good about myself. My skirt complimented my nice hips and butt. I wore my white Burberry shirt that had plaid binding. It really showed my cleavage. I was blushingIn the mirror. I straightened my shoulder length dirty blonde hair and looked myself in the mirror one more time. It was there I knew I wasn’t ready for the night that was about to happen. It’s funny how I took a black cardigan thinking that somehow it was going to shield me from evil eyes.
It started when I jumped on the L early that night. It wasn’t too bad. Boys were looking at me, and I felt pretty good about myself. When I got to the Wrigglyville stop it was like being dropped off in the busiest place on earth. It was just too much too absorb. The drunk boys starring at me with animalistic eyes, and getting nasty hit lines like she’s so fucking hot, I’d totally fuck this shit out of her… I was scared. I had made a mistake. I instantly went back on the red line back. I don’t remember too much to be honest. I remember being really cold, frozen. There were a couple of homeless people saying nasty things to me. They got more aggressive as I was frozen and shocked at how nasty these guys were talking to me. I kept on thinking, don’t move… don’t breath… don’t talk… it’ll go away… as I stared into the abyss of dirty floor. It was a long ride back. I wanted to cry… but I just couldn’t. If I didn’t do anything I would be okay. The L stopped one stop away from mine, and I heard the word BITCH as one of the homeless guys grabbed my legs. I ran out of there. I must have looked ridiculous running out of that train with my heals.. and panting deeply as I went down the steps.
I was alone. I was safe. There was not a soul in site. I probably should have been alert seeing as what happened earlier. I just walked with my head down as I strolled down the sidewalk. No purpose, and just letting life guide me. I was definitely in my own head while I was strolling down that sidewalk until I felt the wind touch my legs and I smelled something familiar. It was the smell of old leaves and the beer of the lesbian bar I had walked by several times. It felt safe and calm. I could use calm.
It was definitely a interesting yet relieving experience to enter my first lesbian bar. There was black lady bouncer who towered over me and had huge muscles. She looked at me defensively at first, and approached me to check my ID. But something about her and how she looked at me changed. It was as though she could see how my night went. She relaxed her expression, gave me a kind smile, winked at me and told me to come in and get comfortable. I felt safe… I can’t express that enough. I was definitely getting many looks as I went to the far end of the bar. I was shy I must admit. But I felt good to be there. The bartender turned to me and smiled. She asked if she could get me a cold one, and I simply nodded. It was a calm scene compared to most bars I’ve seen. I constantly got looks from the other girls. For the most part it was filled with older women. A mixture of earthy, butch, and a few women wearing evening dresses. I looked up to the bartender and asked how much I owed her, and she kindly said it was “on the house kid.” Then she asked if I wanted another. It was amazing the connection this place and people had with me. It was as though this place was shielding me from my bad night. I got comfortable enough where I started to look around and catch some lookers checking me out. I’m sure I stuck out like a sore thumb.
Then I heard a couple of boots walk up behind me and come to my left. She was tall and bulky. I couldn’t see her at first until she stood right next to me. I remember the smell of leather, cigarettes. She was wearing a black leather jacket which was studded and had a skull on the back. She looked like a biker or a truck driver… I wasn’t sure. She had these tattoos on her neck and these jeans that had grease stains. She had short white hair and a strong jawline and deep blue eyes. She was anywhere between 50 and 60. I could tell by her raspy voice that she drank a lot when she was younger. She had this stern authoritative presence as she put her hand up and said, “ONE,” very rapidly and the bar tender quickly uncapped a bottle and handed it to her. She took a huge gulp. I must have been starring at her the whole time… she had this terminator look to her. She put the bottle down and gave me this smile. Then I smiled… shit… then I blushed. I didn’t mean to smile like that. What was going on with me? There was something I liked about her instantly. It was her walk, her confidence, her aura. I felt with her there, nothing in the world could hurt me.
“What’s a nice young girl like you doing in a place like this.”
I felt put on the spot. I liked her aggressiveness but I was annoyed by her confidence a little. I guess that’s why I teased her. “Same as you…”
Her smile got bigger… “oh really? What do you think I’m doing here? In fact… why do you think I walked all the way down the bar to talk to you?”Oh damn… checkmate. She is pretty confident. I giggled, As I tried to think of what to say. The truth… easiest. “Well honestly, I had a scary night, and this just seemed like the safest place to stay for a bit.”
Her face got serious, almost concerned. She took her drink and came and sat right next to me on the empty stool on my right. “My name is Sam.” Her leather studded hand greeted me. I met
Her firm grip of a hand, “I’m Cassandra, my friends call me Cassie.” We had a few beers but mostly talked. She had a friendly way of opening me up. She seemed interested and concerned. We were easily there a couple hours just talking like friends.
“You are too young to be going out in the city late at night. There will be plenty of time to have fun when your older. How old are you?”
I felt scolded at a little. I know she didn’t mean it but it sounded pretty condescending. I simply replied. “I’m nineteen.”
She scoffed and said she could be my Grandma. Then asked if she could take me back home.
I felt a little betrayed. Did she want to get rid of me now because of my age? She pissed me off a little. So I gave her a little attitude.
“Well you can do what you want. All I know is I’m staying here tonight.”
I could tell I got under her skin. “Well I’m not going to let you out of my sight until I drop you off.”
I was really pissed off. I didn’t like being treated like a little girl. It really bothered me. So I decided to test her bullshit.
“Well maybe I want someone here to take me back to their place.”
I saw her lips purse. And her eyes widened. I had pissed this lady off.
“Is that what you want? You want some older butch to fuck you? Have you ever been with another woman?”
Sam paused and looked around.
“You are too young for this place, these women will chew you up and spit you out literally. They will fuck you stupid.”
They were now moving the tables and the disco ball was coming on. The music was starting to get played and the ladies immediately started to get the club started.
Sam then ran her hands up my legs. “These vultures will pick you clean.. is that what you want?” I think she was trying to scare me. I wasn’t scared or her. I let her run her hands. I dared her. It was as though she was expecting me to move or something… I knew she liked it… even if she was trying to scare me away… ”
Sam stopped. She looked at me.
“let me drop you home… please.”
I didn’t say a word. I got up and joined the other ladies on the floor. Sam looked bothered and annoyed. Good. She thinks she’s like my mom or something. I’ll let whoever gets me first do what they want to me. It’s amazing the immaturity I displayed that night. I wanted to escape what was left of my childhood. But more than anything, I wanted someone to want me…
It wasn’t long where this woman with brown short hair, tall and slender started grinding on me. I was getting hot. I was enjoying this. Sam looked at me from the stool with a resting bitch face. She hated me. Then she turned away. I was dancing with this younger woman and I could tell she really wanted me. She was getting handsy, groping my ass. Her hands ran up my waist and groped my breasts… she was controlling my body and my face turned to meet hers… she was going to kiss me… the song was over and I needed to pee. Damn, I excused myself and went to the bathroom which was next to fire exit. I went to restroom, freshened up and walked out. I headed towards the main floor when all of a sudden I felt someone grab my right arm and pull me out of the building from the exit. Sam pushed me against the wall and started making out with me.
She was strong. My shock slowly melted away with passion as Sam pushed her tongue in my mouth. She was an animal. She tasted of beer and cigarettes but I was just turned on. She picked up my 5’4 body by my legs and starting grinding on me. I was able to look around. Just garbages and a wooden fence. We were all alone. I wrapped my legs around her. I wanted to feel her tongue in my mouth. She pulled my hair to move my head aside and leave my neck vulnerable for her and started to kiss and naw on my neck. It was so passionate, I was moaning and breathing hard. Then she undid the first two buttons of my shirt and pulled my bra cup down and feasted on my left breast. I shrieked! She licked, sucked as it seemed like she wanted to eat my whole breast. I helped her as I put my hand around her gray hair and pulled her head closer. As she took more of my breast In her mouth… I came. I gently stroked my lover and kissed her head as I encouraged her to feast on my lovely breasts.
She grabbed my hand and took me to her place…
I don’t think I did much walking when she dragged me to her apartment and carried up the steps. I thought she was being aggressive outside… she started pulling and tearing my close off. When she got to my bra me underwear she took a whole minute to look at me. I felt special… helpless but special. She was taking to places I had never been… She took me to her room and kissed me. She was a great kisser. I needed a few moments to catch my breath. She put two of her big fingers in my underwear and I yelped. I hadn’t had sex in ages. But the pain faded away and she slowly finger fucked me. I was starting to enjoy it… so much so I started grinding on her hand… both her fingers were deep inside me as I was basically eating her face.
The only time we stopped that I can remember is when she asked if she could go deep inside me with her strapon. I wanted her inside me so bad. Without hesitation I said yes. She opened her drawer with her long arm and pulled out this long… thing… she took off her clothes quickly and put her strapon on. There were two sides of it. One was long and thick, the other was short and thicker. She pushed it insider her and pulled my underwear off. Without hesitation she slowly shoved her thick cock inside of me. She kissed me slowly and gently and I looked deeply into her kind beautiful eyes… she said I was the most beautiful thing she had ever seen. She was such a stud… omg… I wanted her to have me… she was being so gentle with me, so I encouraged her… I wrapped my legs around her. She was such a big and thick lady, I pulled her inside me. I told her to fuck me. I wanted her to have me… without hesitation she fucked me fast and hard and deep. I could feel her pleasure as she really got deep in me. I Imagine she was having her most intense moments when it was deep inside her too. I was building up… I was grabbing her sheets because of the tensity, but they were coming off the corners of the bed… I unconsciously used my nails on her back and it just encouraged her to go faster… I came… came so hard I passed out. She came right after I did as she pushed in one final time. It was as though she was coming inside me… we savored that last moment before passing out that night.
I woke up early that morning to a wet sensation on my legs. Sam was kissing my tummy, my legs, and now she was feasting on my pussy. I never had anyone down there before… it was so amazing. It literally felt like she was eating me out. She was using her long tongue to lick my clit while fingering me. And then sucking all my wetness. I had more orgasms that morning than my whole life. Then she fed on my breasts while her fingers were inside me. I felt like this woman devoured my body literally. I fell asleep again for about an hour. She was asleep this time… So I though I’d return the favor. I started to lick and suck on her hairy pussy. At first it was very different for me but it slowly became natural. She woke up and pushed my head down. So I guess I was at least okay. She did all the work it seemed as she grinded on my face and in my mouth. I helped her cum and She thanked me.
She went back to sleep and everything seemed to quite and beautiful.
I stared out the window at the beautiful Saturday sunlight gleaming and radiating her apartment that morning.
A woman had been born.