It was the end of winter break, and I was meeting a girl at the airport to head to NYC for a week of sightseeing before school started up again for the spring term. She had been my best friend for the past six months, and I think she'd known all along that I had a massive crush on her. She hadn't acknowledged my interest, though, except to say that she wanted to be single after a bad experience breaking up with her last boyfriend. I arrived an hour late, and as we were loading her luggage into the trunk of my '94 Volvo, it stalled out, so we were stuck waiting in the front seat until it would start again.
While we waited, we talked. I asked her about her vacation (she lived in Hong Kong, so any story was interesting), and told her about mine. And then it was silent. "I missed you," I said. "A lot."
"Me too," was her answer, and she leaned over and gave me a quick hug. In the darkness I fumbled for my keys and tried the ignition again; the car started and we headed for our college.
That night we were staying in the dorms, planning to make the trip to NYC the next morning. I dropped my two duffel bags off in my room, then went upstairs to hers to keep her company as she sorted through her three suitcases and two boxes of clothing, electronics accessories, and documents. Hours later, she finished putting everything into its proper place, and it was time to sleep so that we could get an early start in the morning. We hugged, said goodnight, and then I hesitated before going out the door. "You don't want to go downstairs tonight, do you?" she asked.
"You have to understand that I don't love you," she said.
She had a liberal attitude when it came to physical affection. All sorts of hugging and holding hands and kisses on cheeks were acceptable, which was very different from my upbringing. So I'd been surprised the first time she had asked if she could just fall asleep in my bed (we'd been watching the Colbert Report online and she said she was too comfortable to get up). But I'd gotten used to it, and understood that it didn't mean anything. I thought that that night would be no different. I wanted to stay with her, even knowing that my affection wasn't reciprocated.
She had a liberal attitude when it came to physical affection. All sorts of hugging and holding hands and kisses on cheeks were acceptable, which was very different from my upbringing. So I'd been surprised the first time she had asked if she could just fall asleep in my bed (we'd been watching the Colbert Report online and she said she was too comfortable to get up). But I'd gotten used to it, and understood that it didn't mean anything. I thought that that night would be no different. I wanted to stay with her, even knowing that my affection wasn't reciprocated.
Imagine my surprise thirty minutes later, when, after lying in the dark talking for what seemed like an hour, without warning, I felt her lips against mine. It was just a quick peck, but it stopped me mid-sentence. "What was that?" I asked.
"What was what?"
I rolled over and pulled her head toward mine, and kissed her as passionately as my inexperienced lips would allow. "That," I answered.
We made out for hours, and I felt and saw real breasts for the first time in my life, but we stopped short of going further that night. The next night, after driving to a friend's place in NYC, I audaciously reached down and teased her with my fingers, but she prevented me from pulling off her underwear when I made an attempt. The third night began the same way. We kissed, I fingered her, she ground against me for all she was worth — and then abruptly she was still. "I can't help myself," she whispered in the darkness. "I want your dick."
I was stunned momentarily, but my instincts took hold and I started to fumble with my pants button in the dark. But she grabbed my arms. "You have to understand that I don't love you," she said. "If you don't want to do this with someone who doesn't love you, I'll understand."
It was at that moment that I realized that I, tragically, truly did love her. But my body didn't give me time to think about how miserable that would make me in the near future. I wanted her more than I had ever wanted anything before in my life. Every fiber of my body was screaming at me to stop stalling, to pull this girl against me as tightly as I could and never let go. I pulled down my pants, peeled off her underwear, and lay on top of her, hard as a rock. I whispered breathlessly, "That you would ask that question means that you care. And that's enough for me," and slid into her.
My unrealistic expectations and her relationships with other boys spelled disappointment for me and disaster for our friendship. We had sex a few more times, but it was never like the first time again. It was worth it though, for that one night, that one hour of honest innocence and senseless happiness. I'll never forget it, and I'll never forget her.
I lost my virginity during an argument about socialism...
I lost my virginity during an argument about socialism.
I was always a pretentious kid, so the fact that a political argument got me heated in more ways than one wasn't surprising. And the guy I was with, Jesse, was everything a teenage girl could want: tall, dark, handsome, older... and obsessive compulsive, but never mind. Even at sixteen I knew that sometimes, in love, you had to overlook the little things. At least I knew his hands were always clean and well-manicured.
I had known him for years. We met in an alternative school, when I was a twelve-year-old depressed Goth-in-training and he was the moody poetic genius I read about in my dogeared Anne Rice novels. An Armani-wearing "poor little rich boy" cliche, Jesse was the excitingly advanced age of fifteen, and of course knew everything about everything. I was smitten from the beginning, but he was always out of reach. We talked all the time, but I worried I had become his friend with no hope of being anything more, especially since I was insecure about my body. It had betrayed me, going from slender and prepubescent to hourglassed, which, to a teenage girl, means fat. So I crushed in silence and hoped in that terribly Goth way that one day he would see my suffering and tell me he loved me back.
Four years went by with me holding a torch for this boy. We changed schools, and, since this was before everyone had internet or mobile phones, we constantly wrote letters to each other. He had a penchant for the dramatic, writing on heavy paper with calligraphy pens and stamping his notes with his own, personalized wax seal. It was all stupidly romantic, mostly about our worldly concepts and our plans to change humanity. Jesse was born into a wealthy family, while I was fighting through on my own — with his money and my passion, we thought we could do important things.
One letter in particular changed everything. He wrote to me while I was in boarding school, saying that someone he knew had a dilemma. This person loved three women. One was his soulmate, but it was unrequited; one was familiar but the passion was lacking; and one was an enigma. Who should his friend pursue? I was no idiot — I knew this was about him and, potentially, me, if I could figure out which one I was. I took a stab in the dark and wrote back, "He should go for the enigma. Why chase the girl who doesn't want him, and why stay with someone he doesn't love?"
Soon we had our first date. I was ecstatic and probably overeager — I hadn't yet heard that Cosmopropaganda that all men prefer to pursue, so I was upfront about my excitement. Our first kiss was deep and sweet. I felt safe, mostly, with just a touch of fear of the unknown to keep it interesting. He asked me what I liked and didn't like, what I wanted, giving me agency in a way I hadn't experienced with other boys. Slowly dates turned to snuggling at his home, discussing the political news of the day.
And that's how I lost my virginity — crosslegged on his bed, spouting idealistic nonsense about how socialism could work if only we tried hard enough. Jesse deftly refuted my argument, I retorted, and the next thing either of us knew we were kissing, hard. My shirt came off, then his, then we tried to remove each others pants but gave up and, giggling, removed our own. He kissed my neck, biting gently while I moaned and writhed under him, my nails digging into his pale skin. His lips pressed against mine as he slid his hand into my bra to feel my breasts.
I remember not feeling self-conscious. I felt safe. I had known him for years, forever in high-school time, and I loved him dearly. I didn't try to cover my belly as I would later in life, when I again struggled with body image. I just let him touch me, and touched him back, marveling at how soft his skin was and how sensitive mine was. One hand slid into my panties, and he looked at me, as if asking for permission. I nodded, and he slowly pulled them off me, kissing my thighs as he went. My foot got tangled in them at one point but they were eventually removed and on the floor.
He put a condom on without asking, without being cajoled. Years after I would realize how precious this behavior was, and how it demonstrated a respect for me and my body that was rare. Jesse had a small bottle of lubricant next to the bed, and used some on his fingers to get me even more aroused and ready. His cock head pressed against my opening, and a few kisses later, he thrust in, slowly but firmly. I don't remember there being pain, just a sense of overwhelming relief and smugness that I was having my first time with someone I actually loved.
Well, he was just getting started. That boy fucked the living hell out of me. He was gentle at first, sure, but it didn't take long before I was clawing him to get him to go harder and faster. I loved my first time so much I insisted we try it a few more times that night.
It wasn't made to last. We split up eventually, I moved away, we lost touch. I wonder where he is, sometimes, but he's not on Facebook so I'll never know. But he'll always be special, and I'll always love him for making my first time memorable.
Male • 19 years old • Alabama
Sophomore year in college, I had a girlfriend whom I'd been dating for a year. She didn't want to have sex until marriage. I respected that, but as a teenage boy who'd never had sex, I felt pressure building.
One weekend, I went on a "team building" trip in the mountains, away from my girlfriend. It was full of new freshmen, one a girl named Lisa who was extremely friendly towards me. She'd tease me by taking my papers, smile at me, and sit next to me when she could. I knew she was crushing on me.
The first night of the trip, I was staying in a lodge with four other guys. We were just hanging out in our room; Lisa found me and came in to hang with us. When the time came to go to bed, I invited her to stay the night in my bed, on the bottom bunk, while four other guys were sleeping around us. Bold, huh?
She agreed. I had no intention of anything sexual happening — I had a girlfriend. But then our bodies began to rub and our pelvises began to grind. She made moaning sounds, and I didn't want her to disturb the guys sleeping around us, so I kissed her. I was sleepy so I wasn't thinking straight. She apparently liked it, and we started making out. Our hands wandered. Hers went into my pants, mine under her bra. Eventually, she gave me a hand job, and I came on her stomach. I could tell it wasn't her first time giving one. That was the end of the night's activities.
I had no intention of anything sexual happening — I had a girlfriend.
Once we returned from the trip, I had no idea what I was going to do. Could I really try to have two girlfriends at once? What if one of them wanted to be in a relationship on Facebook? About a week later, my original girlfriend was staying in my dorm room and Lisa called. I didn't know it was her until I picked up, and she said she was out front and needed me to let her into the building. Being nice, I did. She came in. I introduced Lisa to my girlfriend as "my friend," and that was when things got tense. Lisa wanted to stay the night. My girlfriend was already in her pajamas planning to stay the night. They obviously couldn't both stay.
Once we returned from the trip, I had no idea what I was going to do. Could I really try to have two girlfriends at once? What if one of them wanted to be in a relationship on Facebook? About a week later, my original girlfriend was staying in my dorm room and Lisa called. I didn't know it was her until I picked up, and she said she was out front and needed me to let her into the building. Being nice, I did. She came in. I introduced Lisa to my girlfriend as "my friend," and that was when things got tense. Lisa wanted to stay the night. My girlfriend was already in her pajamas planning to stay the night. They obviously couldn't both stay.
Taking Lisa out into the hall, I explained, "My parents don't want me to have a girlfriend. They want me to focus on studying." I also said that my friend in my room was having a bad day and I was taking care of her. I was in essence breaking up with Lisa; she cried, but said she was okay. I walked her back to her dorm room across campus, and she wanted to "kiss goodbye." Our kiss turned into a makeout session which then turned into the question, "Do you want to have sex?"
We agreed we would, and the clothes came off. I raided her roommate's condom stash, and lay on top of her. When I entered her, she said, "Slowly!" I began thrusting, kissing her. She moaned. But because I had to pee, I was extra sensitive, so I came in about a minute and pulled out. Lisa didn't really seem to mind. We cleaned up, and I kissed her goodbye, saying that we would stay friends. I was embarrassed about my performance, but I had to get back to my girlfriend waiting in my room before she got suspicious.
Returning to my room, I told my girlfriend that Lisa was a girl who liked me, and that she'd been crying in the hall because I'd told her that I already had a girlfriend. My girlfriend accepted the story, and we went to fool around in bed with my body still covered in another girl's sweat. So my first time was cheating on my girlfriend with a girl I'd known for about a week and had just broken up with — and it lasted for only sixty seconds. I am a horrible person.
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