By Ali McPhersonIn Insecure, the heroine Issa gets it on with four lovers. Lawrence, who she previously dated for five years, her ex Daniel, her lowlife neighbor who she met like twice, and her most recent lover Nathan. From the makeup sex with Lawrence to an intense rendezvous in a recording studio with Daniel, it didn’t surprise me when she got down on a Ferris wheel at Coachella with Nathan (who—spoiler—then abruptly disappeared near the end of the current season). Despite the turbulence of her relationships, Issa made it look easy and fun. Unfortunately, my first time was nothing like this.My single mother helped me make the right decisions when it came to dating and sex. Having been on the dating scene since she was seventeen, my mom had enough experience to back up what she was saying. She always respected herself and gave me the confidence never to need a man to complete me. “Be patient, wait for someone good to come along,” she would tell me. Her best advice was to never get too attached. Well, too late for that.During my sophomore year in college, I met a handsome Ukrainian guy in my journalism class. One day after school he asked me, “Hey, you busy Saturday night?” That following weekend, we sat in a pizza parlor talking for hours, and not long after that we were inseparable. After six weeks of sexting and late-night intense make-out sessions at school, we decided to take it all the way. Turning twenty-one in a month, I was excited and nervous. Growing up in New York City, the boys I met either just wanted to hook up with me or were interested in someone else entirely. Something about this guy was different. He was kind, and respectful. He didn’t pressure me to do anything I didn’t want to do, and made me feel comfortable around him, like we had known each other all of our lives. There was also the intense, burning sexual attraction that had led me to him in the first place, but that was secondary. I had fallen in love with him because he was a brilliant man, and that made me want to sleep with him, more than any other reason. It was during Christmas break that we decided to consummate our relationship. Before doing anything, we waited until his roommates were out of his Staten Island three-story home. “Let’s play some music to set the mood,” he said. I expected my first time would be intense with a sensual R&B artist playing in the background, like in Love & Basketball where Sanaa Lathan’s Monica lost her virginity to her best friend Quincy (Omar Epps). But a soft jazz melody filled the room instead. It was the first time I had come over to his place, because I had wanted to leave a little bit of mystery between us for the first month and a half. Instead of showing me around, we went straight to his bedroom and removed our clothes. We both felt overwhelming sexual attraction to one another, and were anxious to show each other just how intense our emotions were. The passion was rising as we made our way to his bunk bed. As I sat down, I bumped my head against the wood, momentarily breaking the mood. I rubbed the back of my cranium, rolling my eyes at how lame I felt. “Relax,” he whispered between kisses. Telling a virgin to relax was like telling a girl scared of bees to stay calm while a nest of them buzzed around her. “Babe, I can’t get inside unless you open up,” he said. I tried my best but I felt a sharp pain. I started to cry, feeling like a child. We laid on our backs, and he looked over with pity. He wrapped his arms around me, and we bonded for a minute as I wiped the tears from my face. “No crying allowed here,” he said gently, holding me tighter to him. We tried again a few more times throughout the night; each attempt was worse than the last. He was patient, always stopping when I asked him to. When I became very emotional, he even offered to watch The Night Before with Seth Rogen. There has to be an easier way to do this, I thought to myself. Popping one’s cherry can’t be this damn hard. My boyfriend told me, “It’s okay, I’ll wait, we can always get back to it,” yet I knew that he was as concerned as I was. On a day off from work, I decided to call my gynecologist to get some professional advice. Examining me, my doctor explained that there was nothing wrong. “First make sure you are using a condom, and just relax,” she said, using that damn word again.“Your muscles can’t be tight or you’ll make it worse.” She suggested that we use a lubricant. The next few times we tried to be intimate, I’d tighten my muscles, again and again, making it impossible to consummate our passion for each other. Lube or no lube, it wasn’t happening. I also lost count how many times I was told to relax which probably didn’t help things. When I spoke to my mom afterward, she told me not to force it. “When you’re ready, it will happen. If you are not ready, let him know you need more time.” I made it clear that I was more than ready physically, but for some reason, mentally, I was not. The initial sharp pain that came with consummating for the first time was too much to bear, and Instead of letting the pain subside I would just keep him from entering. “When the right time comes, you’ll be able to let go of your fears and let him in,” she said. Three months and a hundred wasted condoms later, I took a deep breath and after a few failed tries and gentle reminders from him to loosen my muscles, we finally did it. It was as if the angels were singing above our heads. I’d be lying if I said it didn’t hurt like hell, because it did. Yet after the sting subsided, lovemaking became wonderful. I was relieved to know that there was nothing wrong with my body. The cure really was to just relax and trust that he was not going to hurt me. Fifteen months later, we broke up for reasons unrelated to sex. On the night we decided to end things, we fell asleep beside each other his arms wrapped around me. The morning after, we went for it one last time before I hit the road. Much like Issa and her ex-boyfriend Lawrence, who hooked up on her couch months after they parted ways, there was still a physical attraction for one another and there was no better time than the present to end things with a bang.–Based in New York, Ali McPherson has published work in the New School Free Press and is currently an editor for Eleven and a Half Literary Journal.