Love & Sex

Ten Illustrated Stories About First-Time Sex

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Funny, sad, and nostalgic tales submitted by Hooksexup readers.

Do you have a great first-time story? Tell us! My First Time runs every Tuesday on hooksexup.com.

My First Time - Illustration by Thomas Pitilli

Illustration by Thomas Pitilli

Male • 18 years old • Maine

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.

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.

My First Time

Illustration by Thomas Pitilli

Female 17 years old Back of a car

My best guy friend, who had served as my first boyfriend years earlier, had recently come out to me as bisexual. His boyfriend was edging his way into our group of friends, which pushed us all a bit more to the wild side. The boyfriend was older and taught us to sneak out of our houses and steal alcohol from our parents. One wintry weekend, we made a daring plan to camp by the lake in our cars. We snuck out late, after listening at our parents' doors to make sure they had fallen asleep enough to miss the noise of our cars leaving.

Arriving at the beach, it became clear that the weather was not conducive to hanging out. It was pitch black and below zero. My friend Monica and her boyfriend, who had recently lost their virginities together, immediately holed themselves up in his car, and I knew they would be practicing their newly discovered hobby to help them generate heat.

That left me, my guy friend, and his boyfriend standing outside my SUV. We put down the back seats to make room, turned on some music and the heater, and chatted for a while. Soon though, we had to turn off the music and heater, because we knew that neither my gas tank or my battery would last through the cold night. So, we had to come up with a way to keep warm.

Both boys knew that I was a virgin. The boyfriend coyly suggested that they could help me out in that department. When I didn't laugh the suggestion off, my friend looked at me more seriously, and asked if I would honestly be okay with it. Partly because I still harbored hopes that he would fall back in love with me, and partly because I was sick of feeling more immature than all my friends because I was the only remaining virgin, I just shrugged and said "Sure."

I took a few shots of the whiskey the boyfriend had swiped for the weekend to fortify myself (even though I hated whiskey). Then it began. I didn't really do anything. It was all done to me. In retrospect, I didn't give up my virginity; it just disappeared one night. We started with me making out with each of them in turn. Then, because I felt more comfortable with my close friend, he went down on me while I kissed his boyfriend. They switched places a while later. Then, the process was repeated, but with each of them penetrating me this time. The experience was not pleasurable for me, but it wasn't particularly unpleasurable either, so I continually assured them that it was great when they asked.

Finally, I told them I needed to pee. I dashed outside naked and ran across the ice to some bushes. As I passed Monica's car, I heard nothing; she and her boyfriend had gone to sleep. This reassured me that the boys in my car would probably be tired too, so I waited outside in the cold, hoping to hear my car fall silent soon. Eventually I was so cold that I was sure my nipples could cut diamonds, so I ran back to my car and hopped in, but insisted that I was tired and it was time for bed.

The next morning, early enough that we were sure our parents wouldn't have woken up yet, my friend caught a ride home with Monica and her boyfriend. As far as I could tell, taking my virginity hadn't made him madly infatuated with me again. I was left with the task of driving his boyfriend home. We stopped for waffles at a twenty-four-hour diner. In the middle of our easy chit-chat, he suddenly looked at me and said, "Seriously, are you okay? Do you want to talk about what happened or anything?" His sincerity was touching, but I brushed his questions off, all the while thinking to myself, "There's nothing we can do now if I'm not okay."

My First Time, First Time Sex Stories on Hooksexup

Illustration by Thomas Pitilli

Female • 17 years old • Dakotas

The summer before my senior year of high school, I started dating a guy from a rival high school's debate team. I refused to have sex with him, because I thought it might somehow hurt my academic performance or make it too weird to debate him at competitions. (Yeah, I was a nerd like that.) It was easier because he lived quite far away. After five months of increasing sexual tension, he drove over to my side of the state one balmy weekend in early October — which just happened to be the weekend I had to take the SAT IIs. In a break between math and history tests, I thought to myself, "Goddamn it, my GPA is perfect, my SATs are great, I don't drink, I'm friends with my parents, I go to debate camp all summer, for Chrissakes. I'm going to lose my virginity tonight."

I don't drink, I'm friends with my parents, I go to debate camp all summer. I'm going to lose my virginity tonight.

So I stole a Trojan out of my dad's dresser — too lame to buy my own, but smart enough to steal one! — and told my parents I was staying over at a girlfriend's house. A big group of friends were there after midnight watching some horrible movies. But instead of staying with them, I left with the guy, in his shitty pickup truck, to get a room at a Days Inn on the other side of town.

By the time we got into the room it was after two a.m. — not my normal hours back in those days — and I was both electrified and absolutely exhausted. He was a virgin too. Neither of us had any idea what we were doing. It took maybe fifteen minutes to figure out how to get his dick inside of me, and I nearly gave up because I wanted to go to sleep so much.

But once it was in, I remember thinking, alternately, "Wow, this is sex?" and "That's all there is?" and then eventually focusing on keeping my eyes closed and not looking like I was enjoying it "too much." (So absurd in retrospect.)

But the most amazing part is, against all odds, I actually got off! I don't know how — I think it was out of sheer horny pervy excitement and the fact that he kind of accidentally bumped me in the right place once or twice. It took me another year and another partner to get off again, but that's a story for a different day.

The next morning we woke up to discover I'd been caught — my parents had figured out I wasn't at my friend's house. Oops.

My First Time

Illustration by Thomas Pitilli

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.

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.

I lost my virginity during an argument about socialism.

Illustration by Thomas Pitilli

Female • 16 years old • Andover, MA

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 lost my virginity during an argument about socialism…

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 Cosmo propaganda 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.

I did some recon at the YMCA, and found a convenient spot at the bottom of a stairwell...

Illustration by Thomas Pitilli

Male • 15 years old • Pennsylvania

The unceremonious throwing away of my virginity ended up being quite memorable, due mostly to venue: the stairwell of my neighborhood's YMCA. By the time I reached ninth grade, I'd had access to my fair share of pornography. I knew (in my mind) how to pleasure a lady, because I'd seen foreplay and penetration from every single angle you could ever imagine, thanks to the invention of the internet. It was time for me to put what I'd seen to the test. How hard could it really be?

I did some recon at the YMCA, and found a convenient spot at the bottom of a stairwell…

I'd been IM'ing with a girl named Ashley from a nearby school, and we had decided we should have sex with each other. She didn't take a lot of convincing. This shouldn't be surprising, since her screen name was "ThongCutie" followed by a few random numbers. (I'm not joking.) We had no place to go to have sex, being that we were both too young to drive and lived with our parents, so at some point, the YMCA became our most viable location. There had to be some place in that gigantic, three-story building where we could successfully pull off some teenage fucking. You don't encounter a lot of suspicion from your parents when you tell them you want to go to the YMCA on a Wednesday night.

I did some recon during one of my frequent trips to the YMCA to play basketball, and found a convenient spot at the bottom of a stairwell that seemed to lead nowhere but to an emergency exit. I figured nobody would come there, and reported back to Ashley that I'd found a place. Classy.

We met at the basketball court. She was in gym clothes with a lot of make-up on and I was in a t-shirt and basketball shorts with three condoms tucked into one of the pockets. (I've noticed that you always either bring superfluous condoms, or stumble upon the opportunity to get laid when you weren't expecting to, when you have none.) She went down the stairs first, and I followed approximately thirty seconds later, when I was sure nobody was watching.

It was all business. She didn't have to ask if I'd brought condoms, because we'd worked it all out online beforehand, along with the color of thong I wanted her to wear (lime green). We barely even talked, but just began kissing and groping each other. I remember how glossy her lips were, and I remember pulling mine away from hers to take a good look at her, like people always seemed to do in movies. This was as close as I got to being passionate during the whole process, and I kind of regretted doing it. We made eye contact, and it was actually more awkward than later, when part of me was inside her.

She wasn't exactly a knockout. She was a bit heavy-set, but she had some larger-than-average breasts and that cute, round face a lot of curvy women possess. The thing was, though, she just exuded promiscuity. This was not her first time. I had to remind myself that I was here to be rid of something, and she would do just fine for that.

The undressing was easier than what you might expect for a first-timer. There was no bra-unhooking, because sports bras don't have them, and the entire experience was completely devoid of buttons and zippers.

Once I had put a condom on, she guided me into her. No foreplay necessary. And then I began to hump on top of her quickly, which was what I'd seen from the veterans online. This girl probably didn't feel any pleasure during the thirty to forty seconds I lasted. She probably didn't feel any pleasure for the next two minutes I stayed inside of her and continued before rolling off, so as to avoid complete embarrassment.

There was no post-coital cuddling, and neither of us wanted it. She was probably disappointed with my performance, and I just wanted to get out of there to go and think about what I'd just done. I quickly dressed, and sat down on one of the steps while I waited for her to do the same. "You don't have to wait for me," she said, and added that it'd be better if we left separately anyway, so I did.

I'd left the condom on when I got dressed, for whatever reason, and went immediately to the bathroom once I returned from the stairwell. I took it off, threw it into the garbage, and then looked at myself in the mirror to see if I looked any different. As expected, I did not.

Then, I went into the gym, where I grabbed a basketball and started shooting around, just like I did most Wednesday nights during my teenage years. Nothing had changed, except that my shot seemed to have improved slightly. But this could've been my imagination. I only spoke to Ashley one more time after that, on the internet, where I apologized for my poor sexual performance, and was told I'd get better with practice. I like to think I have.

My First Time

Illustration by Thomas Pitilli

Female • 16 years old • Leicester, UK

I was sixteen and brimming with teenage angst, melancholy, and anger. Nirvana and the Smashing Pumpkins played constantly on my battered Sony CD player. My hair was dyed a cheap black that rubbed off onto all my pillowcases and the back of the couch. Basically, I was desperately trying to escape the realities of a middle-class, suburban family — the realities being that, rather uncool-ly, I was well looked after by mild, educated parents, fed, clothed, and given a generous allowance that I spent primarily on Silk Cuts, hash, and CDs.

He was twenty, from New Zealand, in a band, a casual pot dealer and skateboarder. Best of all, he lived with a friend in a chaotic, noisy house permeated 24/7 with the sweet smell of burning hash. My parents hated him.

I was sixteen and brimming with teenage angst, melancholy, and anger.

I had met him at a party thrown by his friend and housemate, and we'd spent a pleasant couple of hours smoking and making out. For the next six months or so, we had a sort-of relationship, in which he would text me a few times a week, I would go to his house, and we would smoke weed, watch horror movies, and make out. We were definitely not boyfriend and girlfriend. Nor were we really friends, actually — I was an utterly smitten kitten, but I got the distinct impression that he wasn't overly bothered, as evidenced by the facts that he occasionally forgot my name, and that his housemate used to walk me home because he didn't care enough to do it himself.

Eventually, I decided that the best way to advance our relationship would be to sleep with him. I had already broached the tricky subject of my virginity (in our group, still being a virgin at sixteen was unheard of) and he hadn't seemed too fazed. One day, we had the house to ourselves, and after awhile I decided to take the plunge. My exact words were "Get a condom. Let's do this."

There was a sharp, unpleasant pressure as we got started, and he seemed almost as nervous as I was. After the initial pain of penetration, it just felt weird, and not very pleasant. I was sweating, staring at the ceiling, and counting backwards from a hundred in my head, waiting for it to be over. Although he was disturbed by my lack of participation — I don't think I actually moved or made a sound during the entire process — he eventually finished, and went to dispose of the condom.

Looking down, I realized that the sex-ed warning that I might experience "light bleeding" was a huge understatement. The bed looked like a setpiece from The Texas Chainsaw Massacre, and my underwear was soaked. I had literally not seen that much blood since I'd broken my nose on a bouncy castle as a child. Nearly crying from shame and embarrassment, I tried to clean up as best I could, hobbled to the bathroom and fashioned a wad of toilet paper to line my pants, looking at myself in the mirror afterward to see if I looked different. (Apart from being a bit pale and sweaty, I didn't.) To his credit, he didn't mention the excessive bleeding, and we sheepishly went to share a cigarette in the garden.

It was actually my dad's birthday that day, and when I felt the blood start to soak through my pants, I quickly made an excuse about getting back to a party and left, half-waddling/half-running home. I immediately threw my knickers and pants into the trash, rang my best friend to tell her that I'd finally lost it, and went online to see if anyone had ever died from blood loss after losing their virginity.

Although our relationship died out a few months later, we met up again when I was eighteen, and now we live together. My dad's birthday remains known, between us, as our "sex-a-versary."

Illustration by Thomas Pitilli

Male • 18 • Pwllheli, Wales

I was with my best friend on my second holiday away from my parents. Our destination was the Butlins holiday village in Pwllheli, Wales. Not very glamorous but any playground away from your parents is bliss at that age.

The girl's name was Mel. It's so long ago now that I barely remember what she really looked like, just a vague image. Shoulder-length brown hair, pale skin, slim, quite pretty. She was sitting on a bench inside one of the clubhouses. What was immediately attractive was that she was with a girlfriend, and that meant me and my friend could go for one each. So I started talking to her, and after a few minutes the other girl got up and walked off. Turns out they didn't know one another. We were already getting on so well that we decided to just keep at it and drank into the night.

Somehow we convinced her to come back to our chalet…

All three of us were flirting like mad. Eventually we left before we all got too drunk. Normal drunk was enough. Lots of walking and talking in the freezing night air. She accepted one of our jackets to keep warm. Somehow we convinced her to come back to our chalet. There we continued to talk and be silly and somehow we got into a stupid tickling game that ended up not stupid at all, and I kissed her. As all is fair in love and war, my best friend graciously decided he was tired enough and would try to sleep. She was mine.

Kissing was fun. Her fumblings below the waist were nice too. Soon we were undressed and in my bed. Neither of us had condoms. We didn't care. I tried to go down on her. The taste and smell were odd. In hindsight it probably was normal — I just didn't know what normal was. Also I had no idea what I was doing down there. On the other hand, my cock was a solid rod of teenage testosterone and had been like that for a few hours. She decided to push me back, straddle me and just sink down on me. And fuck, that was nice.

I'd like to say we had sex, but the truth is she fucked me. I just lay there. I was also so hard that my cock was practically stuck to my stomach, which didn't give her too much room to maneuver. Still she fucked me, slow, fast, soft, hard. It just went on and on into the morning. While my penis was still like a steel rod, the alcohol had dulled me enough that I was not going to orgasm. She fucked me harder and harder and faster and faster to no avail. Thinking back on it, I'm surprised she remained so lubricated. Eventually, I touched her arms and told her I'd had too much to drink and we could finish in the morning. We slept together, which was also a really nice first for me. And in the morning, I finished.

A pretty basic story but there are some points that require mentioning.

  1. My friend didn't get to sleep. It was a one-room chalet. He basically got to hear, and probably watch, us fuck all night. After her first orgasm we slowed down and she looked at my friend's bed and asked, "What about your friend?" I asked out loud, "Do you want a go?" And though supposedly sleeping, he politely declined.

  2. On the third day of my stay, we were fucking on the sofa at her place (a two-room chalet) when her mother, aunt, and sister returned. With just one blanket that barely covered us, they decided to make tea and get to know Mel's new naked friend for a couple of hours. During that coversation I also found out a lot about Mel's boyfriend, who was waiting for her back home.

  3. She ditched me on day five after I got food poisoning. I never saw her again. My friend said the food poisoning was pure karma. He was probably right.

My First Time - Illustration by Thomas Pitilli

Illustration by Thomas Pitilli

Female • 17 years old • Germany

I decided I was ready for sex shortly after I found out my older boyfriend and first love was fornicating with half of his college. After our breakup, I escaped my feelings by going to visit my family in Germany.

At seventeen I was a late bloomer by the standards of the European party scene. Too inexperienced to handle my liquor, I drunkenly stumbled from bar to club with my cousins. By the time we got to a club called the Underground I had flirted with and/or kissed countless boys, partly from serious inebriation, partly from resentful bitterness, and partly from low self-esteem. But it was at the Underground that I met Timo.

After our breakup, I escaped my feelings by going to Germany.

He was absolutely beautiful. He spoke to me sometimes in German, sometimes in English, explaining that he was in town visiting his father from Spain, on vacation from his job as a fireman. When I flirtatiously feigned disbelief about his profession, he showed me his badge. Oh, was I in love. I felt like Goldilocks, trying boys all night until I found one that was just right.

I sat outside the club with him all night. I couldn't tell you what we talked about, but when my cousins emerged and were ready to head home, I knew I wanted the fireman to come with me. I leaned on him as we trailed behind my cousins, stopping constantly so I could push him into back alleys and kiss him for a minute.

Except for the two cousins I was partying with, my extended family was at their country home for the weekend, so I promptly locked Timo and myself in my absent youngest cousin's bedroom. We sat on the bed and looked at the posters of cowboys as he asked questions about me.

"Do you like Westerns? Are you hungry? Are you a virgin?"

I answered no to all the three — the last answer being a lie — and with that he started kissing me again. He took his shirt off, and his glorious body made me nauseous, an unfortunate and mood-killing result of Hooksexups and alcohol. I thought about my ex and how easy it was for him to take his clothes off for all those girls, and a wave of "bravery" washed over me. Trying to be as sexy as all the girls in the movies, I pulled off my top, and pulled the fireman on top of me. We kissed and he rubbed. I went back and forth about whether this was what I really wanted.

But he was the perfect blend of aggressive and romantic, playfully teasing me when I was timid and breathing Spanish down my neck to slow me down when I was coming on really strong. By the time he finally entered me, we were on the floor and I had given up pushing his hips away from me as I pulled mine towards the carpet. I'm sure by that point he had figured out I really was a virgin.

Trying to be as sexy as all the girls in the movies, I pulled off my top, and pulled the fireman on top of me.

I remember looking at his hair a lot during these first penetrating moments. It was dark brown and complimented his olive eyes perfectly. He was so damn beautiful it still amazes me to this day. And as he kept inching inside me I stopped being scared and started focusing on how great this was going to be.

Despite some pain and awkwardness, we did it (or rather he did me) on the floor, on the bed, against the closet, and on the computer desk, and it was amazing. He knew just what to do, and when we finally finished for the umpteenth time, I remember telling Timo to throw the used condoms out the window so my family wouldn't find them later.

The next morning, walking downstairs was agonizing. Four flights of pure torture — Catholic karma for desecrating my cousin's room and losing my virginity to someone whose last name I couldn't remember. As he walked out, the fireman kissed my forehead and said something about calling him before he left for Spain. (Sheer embarrassment stopped me from ever making that lunch date.)

My cousin came downstairs, looked at the scattered array of used condoms that littered the sidewalk, and laughed. The secret was out. I was a whore. But instead of judging me, he seemed perfectly unaffected by my behavior. Again I calmed down and stopped being scared.

My first time was not at all what it was supposed to be. It wasn't with someone I loved and wanted to marry. It wasn't in a romantic, candle-lit, rose-petal-adorned room. But none of that is me, which is what made it so great. Timo may not have been "the one," but I'm happy to know that my first time was with someone beautiful and heroic who I am lucky enough to think of as perfect to this day. How many people can say that about their first?

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