Pretty Boys Don't Cry: Chapter 1

TEENAGE LOVE

It was my second year of high school and I was still a virgin. It seemed like all of my friends were having sex. There was an expectation that I was too because of the attention I was getting from girls. I always arrived early to school and before I could reach my locker, I’d be greeted by a plethora of girls trying to put their hands up my shirt to rub up on my abs. In lunch lines, they attempted to grab my manhood. They openly discussed how curious they were about the length and girth of my phallus. 

I was a heartthrob that looked like a member of a boy band but had the maturity of a crooner. Sprinkled with bad boy braids that were paired with diamond studs and I was a father’s worst nightmare. The girls in school treated me like a sex object and I loved it. 

But call me old-fashioned, I wanted my first time to be with someone I would one day marry. 

That’s when I met this Canadian Jamaican girl who wasn’t well seasoned in the patois dialect and wasn’t proficient in dancehall dances or Caribbean wines. Much like me, Shawna didn’t fit in with her family because she was more westernized, and this made her the black sheep. Before I got to know her officially, it was her appearance that held my attention and my fantasies of her that kept me in anticipation of what things would be like if we were more than strangers in a hallway. 

I had a blindspot for pretty girls with long legs, in short skirts, with a hypnotizing walk and a smile that put you in a trance. Combined with her chocolatey complexion and girl next door persona, she was my Kelly Rowland. If anyone was going to be my first I wanted it to be her. If there was anyone worth risking pregnancy or an STI, it would be her. Her merit for these sacrifices was based on beauty alone and I dedicated most of my time to trying to win her over.

Prior to me, she was dating a baller by the name of Jerome. He was a better baller than me but I was more attractive. As soon as he heard Shawna and I were talking, he wanted to confront me. We were in one of the portable washrooms when he asked, “Hey, are you and Shawna talking?” I responded with, “Yes, I heard you guys were done a month ago.” 

“She doesn’t put out,” he said. “I was with her for like six months and she never let me hit once. If you’re just there to hit it and quit, it would be a waste of time.” He laughed and continued to say that no pussy is worth waiting that long. 

I looked at him and chuckled. 

“Thanks Jerome, but girls don’t tell me no, they tell me not here.” Then I walked out of the bathroom and went to class. Next time he saw me, I had my arm around Shawna’s neck and a smug look on my face.  

Shawna and I had intimate conversations that would start at sundown and go on until sunset. We talked about anything and everything. Not knowing how to express myself emotionally, I relied on R&B music to profess my love. I modified the Teddy Pendegrass song You're My Latest, My Greatest Inspiration in love letters that I sent to Shawna: 

“I have a plan to give her all that I have, that I would be everything, everything she thinks I am. That she made life a joy to live and I was thankful that I was blessed to know her.”

Maxwell’s Fortunate lyrics read: 

I never dug anyone like this, that I never had tasty lips to kiss, that I never had someone to miss.

It wasn’t long before she told me that she loved me and that she would be willing to do anything for me. That kind of love was something I didn’t even receive from my own mother, and just like that, I was in love with her too. 

It was time to take our relationship to the next step. We had already talked about having children and spending the rest of our lives together. Despite how flirtatious I was with girls at school, Shawna was known as wifey. I started bringing her roses to school. The attention that she got from everyone made me feel like a good boyfriend. 

But from the perspective of our peers who didn’t know me, I was a flirt or a womanizer because of my interactions with other girls in my school. To my male peers, I was a gyalist (A man who obsessively seduces and deceives women) or a pimp. I had girls buying my lunches, taking my notes, carrying my books, and providing me with affection that my male friends wanted.

I didn’t understand how it was considered disrespectful. The short-term high I got from the validation of my peers created long-term insecurities for Shawna. Even though she had already put me on a pedestal, she began questioning my loyalty. She started giving attitude to my female friends. She would accuse me of having sex with all the girls that gave me any kind of attention, even my teachers. 

“Since you like spending so much time with them, why don’t you go and be with them instead.” That was Shawna’s favourite line. 

She didn’t understand that I couldn’t give up the perception of me. I enjoyed the respect I received from my peers and how it made me feel. But Shawna began to question if she would be enough for me sexually. If she could live up to what she thought were my high expectations. The validation that was increasing my confidence was lowering hers and I wasn’t willing to give it up just yet. At 15, that kind of attention was still important. I wanted to have my cake and eat it too. 

Being solution-oriented, I decided to increase my gestures of love in hopes that it would strengthen her trust in me. When I ran out of my allowance, I could no longer afford to buy her gifts. It was time for me to get a job. 

One of my female friends hooked me up. The job was easy and paid more than minimum wage. All I had to do was read a script to conduct surveys. 

My persona at high school had followed me to work. A coworker named Nita looked like an actress or model that you would see on television or in movies. She looked like Regan Gomez and had this beautiful caramel complexion, an ass that was shaped like an onion matched with a small waist and wide hips. She was a blindspot that I tried to ignore and giggled when she caught me mesmerized at my desk. 

I was too shy to talk to her and she was tired of waiting for me to say something, so she made the first move. I felt she was out of my league especially being three years older, but my persona allowed me to be the exception to her rule of dating younger men.

It started out with me making her laugh in between calls then evolved to me confiding in her regarding my frustrations with Shawna. Mainly being that I didn’t feel she was putting as much effort into our relationship as I was. Nita would hear me vent and then remind me of how I wouldn’t have that problem with her. She teased me with stories about the gifts she bought her ex lovers, bills she would pay for them, followed by her romantic gestures—lingerie, candle light dinners with R&B playing in the background during the times they made love.

She told me one day, that could be me. 

Over time our feelings for each other became stronger. Our flirting and conversations crossed boundaries that I knew Shawna would frown on, but I felt as long as I kept it a secret that it would be okay. 

I was becoming frustrated with having to wait for sex and Nita reminded me that I didn’t have to wait with her. But I didn’t want to lose my virginity to Nita and her experience with other men intimidated me. She was so tempting, though, and when I was close to giving into her, an opportunity arose for Shawna and me to finally get some time alone. 

My best friend Mark told me his mother wouldn’t be home one evening and that he would have a couple of hours for us to have sex with our girls without being caught. I would finally have my chance to get it in with Shawna. 

But while we plotted the details of our opportunity to have sex, Mark confessed to me that Shawna was coming on to him behind my back. 

“Carlos, your girl is bringing talks to me,” Mark said, which is slang for she was trying to get with him.

I didn’t believe him because he was chubby and besides him being light skinned, I felt he didn’t have any advantage over me. Plus I didn’t think Shawna could betray me. I thought after all the time I had put in with gifts, romantic gestures and allowing myself to be vulnerable with her, she just couldn’t. It didn’t matter if I was doing the same thing with Nita. From my perspective, if Shawna and I were having sex, then I wouldn’t need Nita to remind me that I was enough.  

Regardless of how insecure I felt around Mark, I couldn’t miss out on the opportunity to finally have sex with Shawna. A sheetless mattress on the floor of his basement was where all the magic was going to happen. I was annoyed because it was our first time and I was hoping he would do me a solid and let me use his room. After all, I was the ghostwriter for his MSN messenger conversations with the girls he was sleeping with. But he didn’t understand romance. 

Nevertheless, I was going to make it work. I turned on the charm but it was rushed. I didn’t want to lose what felt like our only opportunity. The faster I went the less romantic our first time felt. She didn’t get wet enough and I was having trouble putting it in. 

When I had finally got it in, Shawna asked me to stop. She said she wanted to check on her cousin upstairs. Feeling rejected and insecure, I started thinking about what Mark had said. I couldn’t stand the sight of looking at her or the thought of being played. We escorted the girls to the bus stop. On the way back to his house he bragged about his experience. I pretended that I enjoyed my time but couldn’t be as enthusiastic because I wasn’t satisfied.

My ego was hurt. I felt like less of a man but was afraid that if I communicated my feelings to Mark that he would laugh at me. Guys like us didn’t have these issues. 

I wouldn’t have to tell Nita what was going on with me. She could see from my body language and my face that I was unhappy. She just didn’t know what was causing it. Ashamed of what was happening to me and wanting her comfort, I told her it was family-related. She tried to cheer me up by taking me out to the movies. She covered the cost of our tickets and our food and made me feel special again. It seemed like she would actually keep her promises and live up to the expectations that she set for me.

I started prioritizing my time with Nita. The more time we spent together, the more sexual experiences I had. The only thing I wasn’t willing to do was have sex bareback. She expressed how much better it felt, but I was nervous and despite the fact that I went from crossing boundaries to full-on cheating, the consequences were too high. 

That all changed on a day that I skipped going to Nita’s after school and headed straight home.  I had five missed calls and they were all from one of Shawna’s best friends. Before I could go through my voicemail to hear the messages, she called again. When I answered, she said, 

“I don’t know how to tell you this, but Shawna has been cheating on you this whole time.” 

She said that Shawna and her neighbour Justin had been sleeping together since he took her virginity on Boxing day. 

I was dead silent on the phone. I had no remarks or witty comeback to combat how I was feeling. I just tried finding ways in my mind to justify what Trish was saying. I tried making the affair seem less significant by telling myself, “well, at least it wasn’t on my birthday or Christmas.” 

I didn’t want to believe Trish or come to terms with the fact that my first love would play me for a fool, but I thought what reason does Trish have to lie?

I wanted comfort and the only people around me were my parents. If I showed any display of sadness or told them how my heart was broken they would have laughed at me and teased me. I would never hear the end of this failure so I kept my moping for the hallways of my high school and found comfort in between the legs of Nita. I left my home that night with a mission to feel better and punish Shawna the only way I thought I knew how. 

I would one-up Shawna by having sex bareback with Nita. All I could think about was that the whole time, I was holding out to lose my virginity to someone who wasn’t worth it. Nita assuring me that she was on the pill brought me no comfort, but it was too late to turn back now. I wanted her to get off of me and stop but couldn’t help but think about the judgement that came with turning down a girl that looked liked her. Then her uncle knocked and I exhaled.