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Throughout her entire relationship with the man/boy, she had always maintained an online presence on dating websites. She hadn’t met up with anyone of note, but mostly relished in the fact that these guys wouldn’t lose interest in her because they couldn’t see her in person and realize what a visual disappointment she was. Then, one gloomy day in mid-January, she was sitting in the beautiful one-bedroom apartment she had moved into a few months prior, and she came across the profile of a guy wearing a Montreal Canadiens jersey. In the background was a poster of Van Gogh’s Starry Night. Having been raised in a strictly Montreal Canadiens household, and being a huge art lover, this guy seemed worthy of sending a quick Hello. It’s a real mind-fuck to think about how differently her life might have turned out if she had just scrolled past him…

He replied pretty quickly. He was friendly and polite and complimentary and horny. He made it clear very quickly that he was a very sexual person and was interested in trying a variety of risqué things in the bedroom. Having limited sexual experience, she was at first taken aback by him being so forward about his sexual interests. At the same time, he was incredibly charming and made it seem like these crazy sexual experiences would be exciting and fun. He also made it known how sexy he thought she was and how much he wanted to meet her. They texted for a couple weeks and decided to meet up at a winter festival held in the city’s downtown core. It was Groundhog Day, she realized. Six more weeks of winter.

As she walked up the street towards the entrance of the park, she saw him standing there waiting for her. He was wearing his red and black lumberjack coat, black toque, and was sporting a faint five o’clock shadow. Shorter than she would have hoped but, oh well. He immediately complimented her on her bright blue pants. In the coming years he would tell her every now and then that it was the blue pants that sold him that day. They walked around admiring the ice sculptures and immediately fell into comfortable conversation. No awkward silences or moments of uncertainty. Everything was so natural right away. He bought her a hot chocolate. They walked down the long skating rink that circled the city if you made it the whole way around. She slipped on the ice twice because she is very classy. A proper lady, if you will. Fortunately, she had finished her hot chocolate before that. But he was charmed by her. Her innocence, her sense of humour, her eyes, her smile. The smile that he would later make her insecure about by constantly teasing her about the amount of gums that showed. When they came off the ice, they both agreed that they weren’t ready for the date to end and he invited her over to his place to watch hockey. The Montreal Canadiens were playing, of course. She naively agreed, genuinely thinking they were going to watch a hockey game.

When they arrived at his small, cluttered apartment, she could see directly into the bedroom and noticed immediately that he didn’t have a bed. “Odd”, she thought. He sensed her curiosity and explained that he used to live there with his crazy ex girlfriend. She took the bed when she left, along with their two precious cats who he loved so much and was still heartbroken about losing. “Poor guy”, she thought to herself. He was showing his vulnerability. She could comfort him and take care of him and fix all his problems. They settled in on his extremely worn, extremely used futon and started watching the Montreal Canadiens beat the Buffalo Sabres. They chatted casually throughout the first period. She felt comfortable and was enjoying herself. Then, the first period ended. He looked at her and without having to say anything, she knew what was about to happen next. He kissed her. A deep, slow, passionate kiss. Something she had never felt before. Her stomach fluttered with butterflies as he guided her backward, so she was laying down. He grabbed a condom and they started to have sex.

“How many people has he fucked on this futon?”, she thought to herself, but tried to push that question out of her mind. This was the first real casual sex experience she’d ever had. She was definitely not one to usually have sex on a first date. It didn’t hurt like it did with man/boy. It felt good. Really good. Better than anything she had experienced before. He was visibly enjoying himself as well. They finished just as the intermission ended and the second period started. Looking back, she wondered if he had planned it like that? As she stood up to get her pants back on, she smiled at him, and he smiled back saying, “This… this is really something…” Her heart exploded. The Habs beat the Sabres 6 – 1.

That evening she had plans with some girlfriends, and it took her literally 0.3 seconds to blurt everything out to them. They were happy for her. Anything would be better than that dirtbag she was with before, right? …

Right?!

Continue to Chapter Six

Fast forward a few years, on one of the first days of her new job at a hardware store that was opening up in her town, she met a guy. She was 22 and he was 27. “Ooh, he’s older,” she thought to herself. He wasn’t really much to look at. His eyes were a nice blue, but they slanted down and outwards in a way that made you wonder if his mother drank when she was pregnant. He had a decent smile though. He was taller than her. He paid attention to her. He flirted with her. And he was nice. “He must really like me. He talks to me and texts me and pays attention to me… and he’s not even drunk when he does it!” she rationalized. Clearly her standards were not nearly high enough, but she was so unfamiliar with the experience of someone actually reciprocating her feelings. He asked her to hang out. She tried not to seem too eager before she excitedly agreed.

It was then that she found out he lived in his mother’s basement – with his son (every second week). Her friends were quick to bring her back to earth. They tried to be supportive while also trying to make her see that this deadbeat-stoner-man/boy-with-a-kid might not be the best choice for her first real boyfriend. All she heard was “first real boyfriend”. She definitely had her blinders on, concerned only with the fact that she liked him, and he liked her and that maybe, finally, she would lose her virginity. She would finally know what it feels like to be intimate with someone and to feel all the feelings she knew would open her eyes to a vast world of new experiences…

… But it wasn’t that great.

In fact, it was awkward, and rushed, and dry, and painful.

She still lived with her parents at the time. Even though he did too, there was more privacy at his mom’s house. So, she agreed to experience her first time on the old, worn out hide-a-bed in his mother’s basement. Very romantic. They started fooling around and she was both surprised and underwhelmed with what he was packing down there. Probably a blessing, though, considering how painful it was. Could have been worse if he had had more to work with. At the time though, despite her notable disappointment with everything thus far, she still remained ecstatic at the fact that this guy liked her. This guy was willing to be with her, thought she was sexy, and seemed to actually like her. Her reservations were pushed back further and further with each rendezvous they had. For a while it seemed like things were actually getting serious. They even took a camping trip one weekend. They swam and drank and ate meals by the fire. Ever have sex while camping? It’s fucking in-tents! (Sorry – couldn’t resist) Things were going so well, her friends invited him to her university graduation party. What was even more surprising was that he actually came! He met all her friends, her parents, random extended family, even. And they had great sex later that night. For over two years their relationship was casual and fun. She was content.

Eventually, however, things started to change. Or maybe they didn’t. Maybe, actually, she just finally opened her eyes and saw the relationship for what it was. She had never met his friends. Never met his mom. Met his kid once, but by accident. He only texted her in the evenings and at night. He would make excuses if she wanted to really hang out. All they did was smoke weed, have sex, and she would leave. She stewed in the thought that he felt she just wasn’t good enough to be a full part of his life. Not really the dream relationship.

Then, one Christmas, things between them came crashing down when she finally got a new Android phone. Being a lover of the art of photography and of taking her own pictures, she had anxiously been awaiting the day she could download Instagram and edit and filter her pictures like all the cool kids were doing. That night she scrolled through the list of Suggested Friends and saw his name. Without thinking twice, she checked out his profile, which was public, and to her heartbreaking surprise, discovered why he hadn’t been able to hang out with her a few days prior. It wasn’t because he had his son that night, like he had said, but because he was seeing someone else. Someone who was worthy enough to meet his mother, to meet his son, and to share fucking Christmas dinner with!

She immediately typed up a message. She must have reread and edited it a hundred times. In summation, it said that he was a coward for not telling her he was seeing someone. That she knew she wasn’t his girlfriend, but as someone who he had had sex with not that long ago, it would have been common courtesy to let her know that he was also sleeping with someone else. It’s not that he met someone, but that he didn’t think enough of her to even tell her about it. His account became private very quickly after that and she never received a reply. That was the end of her first “relationship”.

And then she cried. She cried, and cried, and cried. That was only December 25^th. There was still at least ten days of holidays left. Ten days of nothing to do but sit and think about how undesirable she was. How worthless, how fat, how pathetic and disgusting and desperate she was. She went over it again and again, that a guy as pitiful as that was still not interested in her. She must really be at the bottom of the trash heap if even he didn’t want her. That New Years Eve was a blur, which is exactly what she wanted. She needed to be drunk and numb if/when she hooked up with another guy who would deny his interest in her if questioned. The new year was upon them, and she was done letting guys treat her like a second thought. Like she wasn’t good enough. If no guy wanted her, she didn’t want a guy either. She was going to be happy on her own.

That lasted a month.

Continue to Chapter Five

During that time, she was working after school and on weekends at a local coffee and bake shop. One of her coworkers was a guy she knew from her high school. He was a year older and her first impression of him was that he was a little bit scary. He had an angry energy about him. Big and tough, nothing to prove to anyone and Fuck You if you crossed him, was the impression she had. After working together for a little while, though, she discovered that he was actually pretty nice. He was helpful and kind and even a little bit funny. The more they talked and got to know each other, the more she realized that this guy had a crush on her. Someone had a crush on her!

What kind of parallel universe had she walked in to?! The only problem was that she knew she didn’t feel the same way (typical). Part of her wanted to like him like that, but a bigger part had let peer pressure dictate whether or not she would give him a chance. He wasn’t the most attractive guy. He was a bit sloppy looking, on the chubbier side, and was known in her high school as a bit of a dirt bag. Her relationship with him really only came to life when they were working. And then, she started getting invited to work parties. Occasions where people from her school weren’t around to criticize her for entertaining his flirtations. Add in her best frenemies Bacardi and Smirnoff, and she might have even married him if the idea had come up. They never had sex, but they definitely made out. More than once. Those parties are a very foggy memory at this point.

He eventually told her point blank that he liked her and wanted to date her. She tried as politely as she could to tell him she just didn’t see him that way but that she wanted to be friends. Her attention at that time clearly lay with guys who had no interest in her and who treated her like shit (i.e: Fancy Car Guy). He was likely pretty used to that answer, so they were able to continue on like nothing had happened.

And then, it was prom night. Even though he was a year older than her and had already graduated, he and his friend were still buddies with a lot of people in her grade. After their prom dinner, her graduating class celebrated at a nearby ski resort. It was June so obviously there was no snow. It was just a swanky chalet on the other side of the border where there were no chaperones and the legal drinking age was 18. She didn’t know he would be there. But once he saw her in her after-grad outfit, hair and makeup done, looking better than she usually did in her hair net and visor, he wouldn’t let her out of his sight. The night was a blast, and they all crammed into the school bus they had rented to shuttle all of them home. Her parents were gone away that weekend, so she had gotten permission to have her friends over for an after, after party. What should have been like 5 or 6 girls, ended up being at least 10 people or more, two of whom were her co worker and his friend.

The after, after party at her house was a drunken mess, to say the least. She and her co-worker somehow ended up together on her futon in her basement bedroom. They kissed and cuddled, and she definitely led him on. Intentionally or not, she did. She just reveled in the validation of knowing he wanted her. Later, as the sun began to rise, she ended up chatting with his friend in the front hallway. Leave it to her to never be able to resist a red head. Somehow, they ended up kissing. She was definitely more in to him. No contest. Then, before she knew it, both guys were engaged in a full-on fist fight right there in front of her eyes. Her co-worker had seen his friend kiss her, and without hesitating, dragged him outside to kick his ass. It was 5 o’clock in the morning and two guys were fighting over her in the street. She shouted for them to stop while one of her friends and a random girl from her school who had joined their after party, ate pepperettes and watched the drunken entertainment. Eventually the fight just ended and they both just walked home. He barely spoke to her after that and eventually moved out to the east coast for school.

Things with Fancy Car Guy were still going on through that drunken prom debacle. It wasn’t until midway through her first year of college that the showdown at the mall had occurred. Once all that was behind her, she wanted to branch out and meet people outside of her circle. One weekend in college, she was invited to a party with some people she only sort of knew. A few of the guys were pretty cute, but they were already dating girls in the group, and she was done being the other woman. Then she noticed a guy who she had seen around but had never talked to. He was tall, kind of awkward, and looking back now she realized he sort of looked like your big toe with curly-ish hair on top. They got along well and added each other to Facebook (which had just launched globally that year).

Another weekend a few weeks later, he invited her to a party with all the people she had just gotten to know and become friendly with. She accepted and met up with him at his buddy’s place after work. Everyone was just hanging out in the basement, drinking, shootin’ the shit. After an hour or so he decided that he needed to go back to his house to get more booze, and he asked her to come with him. Yes, she was drunk. But she genuinely, sincerely, 100% just thought that they were grabbing more booze and going back. She truly didn’t have a thought in her head that anything more might happen. They walked into his house and he directed her to his bedroom, which was on the main floor, as he searched for the bottle of vodka. She sat on his bed and waited. Soon, he came in, closing the door behind him. “Oh, holy shit,” she thought to herself. “We’re about to hook up!”

He stood in front of her, leaning down and hovering over her for a second, before he kissed her. She leaned back and he followed her as they made out intensely. Before she knew it, his pants were off, and his penis was out. “What the hell is that?” she thought. For a guy who was easily 6”, things down there were not at all proportional to someone of his stature. Also, why the hell was it crooked?? Then, before she knew it, she was having her head pushed down towards it. First time that had ever happened and she was definitely not a fan. Still, she knew the drill. She knew her worth and this was it. She gave him a BJ and he finished relatively quickly. No attempt to reciprocate, but what else was new with guys? It tripped her up though when he held her hand on their walk back to the party. The night wore on and is all a blur so many years later. After that experience, and knowing she didn’t remember a lot of it, she wanted so badly to make a change. She didn’t want to be the town slut getting passed around for blow jobs, which is definitely how she felt. She just wanted a mutually pleasurable experience with someone. A few moments that she naively thought might lead to something real. But it never did. She lived with the constant sadness of never feeling like she was worthy of that kind of love or attention…

Continue to Chapter Four

Her first real sexual experience was with a guy she met in that same circle of friends. He also went to a different school and was friends with her friend’s boyfriend. He wasn’t overtly nice, nor was he funny or witty. There was just something about him, though. Maybe it was that he was a ginger? (She developed her attraction to red heads at an early age.) Maybe it was the fancy car he drove that made him seem so cool? Or maybe it was his disconnected attitude? His nonchalant, laisser faire, cool, collected, I-don’t-need-anyone, way of looking at things that drew her in. That old stand-by, “you want what you can’t have”, is probably a good way to describe her feelings for him.

It was the biggest crush she had had on anyone in her entire life, up to that point. There was definitely a connection between the two of them, but they only really saw each other at parties (i.e.: when they were drunk), so she never knew if the connection was real or just a drunken attraction. Then, her worst fear was realized when his eye landed on another one of her friends. She was blonde, big blue eyes, and was literally half her size. A naturally thin, funny, beautiful person. Why wouldn’t he fall for her? They eventually started dating and she was left being supportive on the outside, but heartbroken on the inside. She had never told her friend about her feelings towards this guy, so there was no reason for her friend to have any reservations about being with him. That crush was crushed.

Time went on and she just became used to the twinge of jealousy she felt every time she was around them. But she had accepted that he (or anyone, as far as she was concerned) would never see her that way. The only guys that liked her like that were guys she wasn’t attracted to. Then, on one of the many nights they all spent just driving around in their parents’ cars, that all changed. She was the DD that night, cruising around in her parents’ silver 2001 Pontiac Grand Prix. The night had wound down, and she dropped her friends off at home, one by one. By sheer coincidence, he was her last passenger. “I’m not tired, are you?” he asked her. She definitely wasn’t. They decided to find a parking lot to just sit and talk. The conversation itself is a blur now, so many years later, but they definitely landed on the topic of her feelings for him. He told her that he had felt a connection to her too. They both stared at each other in silence, the tension mounting. Then he kissed her. Not her first kiss, but definitely the best one she had had at that point. Before she knew it, her hand was rubbing him over his jeans. She could feel his arousal growing. He took it upon himself to unzip his pants, and she began giving her first hand job. She had never seen someone experience pleasure like that. She felt so powerful.

He was getting close. She was so inexperienced, she hadn’t had the foresight to think about where he would finish, or even what actually happened when a guy finished. “Are you going to take it?” he asked hastily. She immediately realized that he wanted her to swallow. She had never done that before and the thought of it, honestly, disgusted her. However, in her panic of worrying about getting splooge all over her parents’ car, she did what she had to do. At 17, she had zero BJ technique, so she didn’t know there was a way to have it just go right down to avoid getting a mouth full of baby juice. Mmm, salty.

When it was over, he couldn’t have made her feel more used if he had tried. He was cold and dismissive. Her heart sank and her stomach tied in knots. Not only had she just betrayed her best friend, but it was all for nothing. She no longer felt powerful. She no longer felt sexy. She felt even more like no one else would ever want her. All she was good for was for getting guys off. They didn’t see each other for a few weeks after that, but she saw her friend the next day. She couldn’t tell her. She compartmentalized the entire experience. What happened, happened. She couldn’t change that. She could only move forward with the experience she had gained and the humiliation she had suffered. Except, that wasn’t the only time it happened.

Over the next few months, every time they saw each other she was overwhelmed by the desire to relive that feeling of being wanted. He would make eye contact with her across a party, even while he was standing next to her friend, and the thought of their secret became an aphrodisiac. There were a few times her friend wasn’t around during group hang outs, and it was on those occasions they would repeat their indiscretion. A lot of the time, too, he would be the one driving her and their friends around in his fancy car. He would intentionally drop her off last so she could give him car head and then experience the all-too-familiar guilt trip again and again. Eventually, her feelings for him warped into what she thought was something real. By then, he and her friend had broken up, but not because of anything to do with her. Turns out, he didn’t save his ass holery for just her. And even though she knew how shitty he had treated her friend, and even though she knew how shitty he had treated her, he was all she knew about “love” and relationships.

It all came to a head at the end of yet another drunken night. She’s not sure how she ended up being the only girl among her group of guy friends, but they had ended up hanging out at a local shopping mall at like 1am. Eventually it came out that he had told all his friends about what had happened between them. Every person she was with in that moment knew her deepest, darkest secret and there was nothing she could do to take it back. She ended up telling him off in front of his boys, and had to take a cab home alone because he decided to leave and refused to drive her. And even after that, she longed for his attention. Years later, she would make the revelation that it was her experience with this dick head that lead her down a path of bad decisions and big mistakes…

Continue to Chapter Three

She slammed the door behind her and raced down the stairs. Her cheeks were wet from the hot tears streaming down her face. She scrambled to get in the car, her hands shaking. The gravel sprayed as she took off out of the driveway. Turning the corner abruptly, barely slowing down at the stop sign, she realized she couldn’t drive in this frantic state and pulled into the gas station on the corner to catch her breath. Without thinking, she grabbed her phone and called in to work. She would not be clocking in for her afternoon shift. She sat there thinking. Crying. Crawling out of her skin with rage. “That’s it.” she said out loud to herself. And she meant it this time. Finally…

* * *

Growing up, she had what some would call an ideal upbringing. The perfect life. Her parents were happily married, her brother was quiet and reserved and didn’t bother her like a typical sibling might. She had dozens of friends. She was loved and cared about by everyone in her life. Never a witness or recipient of any type of irrational anger or abusive behaviour. She was always the happy one, up for anything at any time. Always available for another fun night or adventure.

Still, no one’s life is ever really perfect. At least not to the person living that life. She knew how fortunate she was to have what she had. And yet she longed for the attention and experiences her friends were having all around her, while she remained impressionable and naïve with no romantic prospects in sight. Everyone liked her, male or female. It was never a question of becoming friends with someone. It was always, “could this guy see me as any kind of match for him instead of the hot girl’s fat and funny best friend?” That was the other issue; her incredibly low self esteem. She was acutely aware that she was the most overweight one in her close groups of girlfriends.

Among her friends there were the two typical beauties with long blonde hair and that girl-next-door demeanor boys find so appealing. There was the French girl with the small waist and big boobs who would awkwardly laugh at the guys’ jokes while simultaneously dishing out her signature resting bitch face (which was really only because she had a hard time seeing and refused to wear her glasses). There was the blonde, laid back, hippie one who loved animals and smoked pot and never let the little things bother her. The smart one who, despite knowing she could do better, settled for the cool guy with the car and all the drugs. And then her – the funny, fat one.

She had many friends in other circles, as well. But those other friends, ranging in body types and personality, were also getting the attention that she so longed for. If even the girls who weren’t “perfect” were worthy of a guy’s time and interest, then why not her? The infuriating part was, that despite all the reasons the high school guys found these girls so attractive, and all these superficial reasons she had to be jealous of these girls, each one of them were (and still are) among the kindest, brightest, most caring, most generous, best people she was ever fortunate enough to meet. She was, and still is, so grateful to be able to call them her friends. Yet, despite her love for them, she couldn’t help but continuously compare herself to them.

She wasn’t ugly. She had a nice smile. Her eyes were a pretty colour. Her hair was long and silky. She knew she wasn’t ugly. Just fat. No one wants fat. Years later, she would realize that actually, no one wants sad, depressed, and insecure. The fat thing was not the problem (Well, it could have been for some guys, but really it was mostly the insecurity stuff). But growing up, during those high school years, through college and her early twenties, all she did was put herself down. All day, every day. No one would ever love her. No one would ever want to kiss her or touch her or be with her unless he was drunk. And even then, on those rare, always drunken, occasions, it was always a secret. No one was allowed to know. The guys were always ashamed of it. They would expect her to perform sexually for them, never returning the favour and always becoming distant and weird afterwards.

With everything in life, there is always an exception to the rule, and this wasn’t the case for every guy. To her surprise, when she was 16 years old, a guy she had met through her friends’ boyfriend was rumoured to have a crush on her. With peer pressure on both sides, she agreed to a double date. She and her friend met up with her friends’ boyfriend and his friend to go to a movie. They sat awkwardly beside each other and when it was over and they were walking back to the bus station, she and he trailed off so they were alone. It was then that he confessed his crush on her and asked if she wanted to go out with him. She was so blown away that anyone could feel that way about her, she said yes without hesitation. The problem was, she really wasn’t attracted to him in any way. He was tall and lanky, light blonde hair, nice blue eyes, and a mouth full of braces. Despite her lack of attraction, he really seemed like a nice guy. Maybe he’ll grow on her, she reasoned. Shortly thereafter, they attended a party and ended up in the laundry room, just the two of them, drunk. Inevitably, they started kissing. It was her first real kiss and it was not at all what she had hoped for. It was sloppy and wet and his braces were a real buzz kill. Still, she was excited to have finally had that experience.

They only saw each other on nights and weekends as they attended different schools. She would go over and hang out with him in his room. The kissing didn’t get any better, and both of them were too inexperienced and nervous for it to go further than that. She would often encounter his mother on her way out. What a nice lady. Eventually, though, she realized it wasn’t fair to either of them for her to continue dating him if she really didn’t like him like that. She ended things after a month, and though he was visibly disappointed, they were able to end things amicably and continue hanging out in the same circle of friends. She felt that she didn’t want to settle for someone she didn’t like that way. She had yet to experience settling for guys who felt about her the way she felt about him…

Continue to Chapter Two