1st Sex Stories

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1st Sex Stories
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20 Celebrities on Losing Their Virginity
You Don't Need to Tell Someone If You're A Virgin
Lauren L'Amie
Lauren is a writer and editor from Texas.


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No two first-time sex stories are the same. But if there’s one thing that’s universally true, it’s that first-time sex is awkward, sweet, embarrassing, messy, nerve-wracking, and hilarious all at once. If you thought you were the only person to lose your virginity while some awful song that was popular in the mid-2000s played, take comfort in the fact that you are not at all.
Here are nine men and women on what first-time sex was like for them, without sparing the intimate and cringe-worthy details.
"I don’t know if anyone else’s gynecologists comment on the strength of their patients’ vaginal walls—but mine has. Like many times. That should preface how my first attempts at sex went. I was 17 and very much in love/super horny so I figured we were ready to go. But he got on top of me and nothing happened. Somehow my tightly-wound brain was sending signals to my vagina that nothing would be entering my body.
Every day we’d try, and same thing — my body wasn’t having it. No peen was gonna pass. I reported back to my friends that it was never gonna happen. After some extensive Googling, I realized that when women are on top it gives them more control during sex. So we tried it, and like magic (actually about 15 minutes of me agonizingly lowering myself onto him) it happened. His eyes and face completely lit up when he realized we’d actually figured it out.
It was funny and awkward and sweet AF and it’s one of my favorite memories from being a teenager. My gynecologist still comments on how strong my weird vagina is, but figuring out ways to relax myself has gotten a lot easier." — Keren, 23
"I was in high school and had just started dating a girl who was a year older than me, which was a pretty big deal. We must have waited two, maybe three months before having sex for the first time (an eternity in the mind of a teen boy).
I finally got that ‘come over’ text I had been waiting for. I was sure I was about to have mind-blowing sex with my girlfriend. I had watched insane amounts of porn leading up to this, and I totally knew what I was doing.
That all changed when we entered her room. She had a lit candle on her desk. There were never candles in porn! Why was there a candle there? Was I actually ready for this? I felt queasy, and dizzy, and I'm pretty sure I was shaking a little bit. Maybe a lot. She asked me if I had done this before, and I panicked and I told her that I had sex once before in eighth grade — the same weird, shitty lie I tried to impress my friends at summer camp with.
After a few uncomfortable (and slightly painful) adjustments to our positions, I was ready to go to pound town. And 30 seconds later, my business in pound town was finished. I knew that she was a little disappointed in the length of my performance to say the least. Even though we don't talk anymore, I do wish that she had known that she was my first because that's a special, mutual connection that I can't have with anybody else." — Brian, 22
"His name was John, he had blonde hair and blue eyes, and he drove one of those weird Toyota FJ Cruisers in yellow. He invited me over one day after school while his parents weren't home. I remember being in his childhood bedroom, feeling very awkward and sort of waiting for something to happen. It was so bad — he was on top and it lasted like 45 seconds, maybe. No romance AT ALL.
The best part is the stupid playlist he had on. Literally while he was inside of me, 'Whatever You Like' by T.I. came on! I will never hear that song and not think of losing my virginity.
He apologized for only lasting a second and then, to top it off, when he pulled out the condom fell off inside of me. I ended up running into his mom when I went to the bathroom and left quickly after. Immediately afterwards I drove to my best friend’s house to tell her about it. Of course I panicked and bought Plan B that week. And of course, like we all do, I slept with him a few more times that summer. To be honest, I don’t think about it much anymore. I’m queer now, and in a happy relationship with another woman." — Nicolette, 25
"I was a teenager, and my friend's family when out of town, leaving their completely empty house available for me to ‘give away my gift.’ My boyfriend and I broke in, hopped on the window bed, and did the dirty to the Dave Matthews Band Pandora station. Afterwards, I remember looking in the bathroom mirror and saying to myself out loud, ‘You're not a virgin anymore.’
Obviously, it was something I'd built up. It was a really important moment to me. In hindsight I wish it had been someone who didn't end up breaking my fucking heart. Or at the very least I wish it had been someone who cared if I had an orgasm or not.” — Kacey, 22
"My first time story was a little shitty , but probably not in the way you’d expect.
I was in college, and I’d waited to have sex with my first real boyfriend. He had already had sex before but was very patient and put up with my wild insecurities. We decided to do it over winter break in a hotel room. He chose to blast the entire Outkast discography from his phone. So I willingly did it to ‘Hey Ya!’ in a tiny hotel room.
Everything went pretty smoothly and, again, he was very kind and patient. Afterwards, we went out for Chinese food. Probably feeling very jazzed about just having DONE IT, he ordered a giant plate of meat and ate it all, even though I warned him that it looked a little sketchy.
Lo and behold, on our romantic walk home, he stopped suddenly and gripped my hand. ‘We have to go back,’ he said. When I asked why, he looked at me, sweating and terrified, and said ‘I’m going to shit my pants.’ I ended the day I’d built up for so many years by waiting patiently, quietly humming ‘Hey Ya!’ while my boyfriend destroyed a Starbucks restroom." — Lucy, 23
"The first time I had sex I was 17, and it was very weird. It felt so much more calculated than I expected, like I was watching us from above trying to pick the perfect/right times to remove one article of clothing and the next and the next. Then remembering the correct way to put on a condom took a minute and I didn't expect the weird silence, inactivity, and pressure I felt while I fumbled with the wrapper.
After it was all over, I remember feeling that the entire experience was very underwhelming. I wasn't sure if I had finished or not but I just got so tired that I wanted to stop! The second time I had sex was so much better when I discovered that I actually hadn't finished the first time." — Tony, 22
"TBH, the first time I had sex it wasn’t consensual and it was with a guy. I much prefer to talk about the first time I had sex with a woman.
We weren't exactly sure what we were doing. We didn't really know if what we were doing was gay. It totally was. Now I see it but at the time we were like, haha this is innocent AF! We're just BFFs who want to feel affection and aren't getting it from boys so whatever! We would kiss everywhere but the mouth. Cheeks, neck, hands, face, head.
We eventually kissed on the mouth, which spurred a whole conversation about the reality of what we were doing. Then in the same week, she came over and we had a few glasses of red wine and she slept over. We started making out and I went down on her. It was a really weird experience because I wasn't sure where we were at emotionally. She came pretty immediately.
In the morning, as we were waking up she turned to me and was like, ‘Hey, you went down on me last night,’ and we both laughed. We dated for about two years." — Maggie, 25
"There was this girl who was really into me in high school. Senior year during spring break, one of my friends went on vacation with his family and asked me to house-sit. I invited my friends over to hang, but then homegirl texted me to ~hangout~ and I told her to come over. Basically, my friends were in the other room when we started fooling around.
When the girl and I were ready, I realized I had to go ask if any of them had a condom. My friend had to go out to his car to get it. But when I put it on I got nervous and was no longer hard, then I took the condom off and in the process I poked a hole in it. I asked my friend for yet another condom and he went to his car again.
We were finally doing it, but I was still so nervous that it was impossible to come. Plus, the whole time her dad had been blowing up her phone and was calling her friends. One of her friends didn't know what to do so she called my friend, who had to come into the room to stop us and tell us that the girl had to go home. " — Carlos, 22
"I had sex for the first time after college. I feel like the biggest hurdle I had to overcome was the confidence in my body and owning that, so once I got over that (s/o to Sex and the City ) I felt I could conquer the world.
But there was nothing special about the night, I kind of just ~felt~ it. Once the opportunity presented itself I was like, ‘OK GURL YOU CAN DO THIS. IT ISN’T SO BAD, JUST DO YOUR THING.’ I just let it happen and had no expectations in mind. I didn’t feel happy but also didn’t feel sad.
Overall, I think my mom was more happy for me than I was. Now I’m having to level with her in the sense that it probably won’t turn into anything (because in her world, we had sex so why not just date the guy?!). But I think the concept of ‘losing’ your virginity has changed, and that it isn't as big of a milestone as people anticipate." —

Sex. Celebrity. Politics. With Teeth
Sex. Celebrity. Politics. With Teeth
The 10 Best Stories About the First Time You Had Sex
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When we asked for the best stories about the first time you had sex , we knew there would be some weird offerings. And there definitely, definitely were.
Did you know John Stamos has a web series on Yahoo where he interviews other celebrities about…
There was more than one international affair. There were people who knew their relationships were doomed because "he is a spooner and doesn't believe in air conditioning which is a lethal combination when you live in the tropics." We learned that there are " sexual vampires " out there. People have sex in the woods and then walk through cow pastures. There are plenty of caught-in-the-acts . Condoms are left on for far too long. A Beer Lady . Blue vibrators . Men who reach orgasm "while looking dead into Tom Hanks' eyes." People having sex in closets at a Christian camp. Dead Heads .
But there were also amazing stories from people who described feeling accepted for who they were for the first time, from people who found this post to be a great opportunity to be honest about their sexual past in their quest for sobriety and people who, after dealing with sexual assault , found someone to love them consensually and without conditions. To those people: right on. Your stories are "the best" in a very different and more heartwarming way than a lot of the stories we're about to feature, and in many ways, far more important.
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Partner: 28-year old Swiss guitarist in my roommate's band
How it went down: The foreplay was amazing. I was on the last day of my period so I told him he didn't have to perform oral sex on me. Before he entered me for the first time he said (in a thick accent), "First I am going to put on this Swiss lube and then I am going to go inside of you". I was so tight (I couldn't even use tampons before losing my virginity) and it hurt so bad that I started crying and I kept making him stop. He then said "I kind of want to put a pillow over your face". I begged him to let me fellate him to orgasm just to make him stop and then I went home to my house where my 4 male roommates were playing Halo. They all high-fived me and then I went to bed.
Location: His bed, in his house he shared with 7 other dudes. His room was the attic.
Partner: boyfriend, who continued to be my boyfriend for the next 3 years
How it went down: The Big Lebowski was on. We had sex. Then I cried and stared out the window (it was raining) for an hour. Jesus wept. That was the night conservative right wing Buggie started to die.
Location: King suite of a fancy hotel in downtown Baltimore
How it went down: It was our wedding night, and despite having done damn near everything else, we had agreed to save the coitus, the final frontier, until we were married. We're Orthodox Jews, and hey, this was how we justified the everything else. He wasn't a virgin, having gotten religion in college after having his share of partners. I was, technically. After the wedding, still in our dress and suit (respectively), we drove over to the fancy hotel my parents graciously paid for (which is kind of weird in retrospect). I told him I had to "slip into something more comfortable", then went into the bathroom and got into a pair of fuzzy pink footy pajamas. I came out and did a striptease to "Natural Woman". I simply couldn't take this whole "deflowering" thing seriously. We commenced the consummation, in the bed and in the bathtub. I remember being underwhelmed, but knowing we would get better with practice. I didn't bleed, and it didn't hurt. I didn't come until we resorted to our usual fingerbanging - the clit wants what it wants, what can I say. Then we snuggled and watched Family Guy (which totally was still funny and not lame back in 2005), and ate leftover wedding food. It was perfect.
Partner: A guy from the periphery of our friendship group
How it went down: I was very drunk and it happened while we were watching Castle , so I stared into Nathan Fillion's eyes on the screen over his shoulder while he got off and I wondered if all sex was really this boring.
Age: 20 (a month-ish before my 21st birthday)
Location: My best friend's bedroom their house
Partner: My best friend and her husband
How it went down: Backstory - I'm a nerd, and was a bit of a chubster in high school, so I didn't date. After I graduated, I stopped talking to everyone but my best friend from school, got hired by the USDA after a successful apprenticeship, and went to community college. I had a bit of a breakdown from lack of social interaction, and over the course of a year dropped out of college, did a fair amount of drugs (mostly pot), lost 60 lbs, became a vegetarian, quit my science job and started working at the local co-op. I met my first boyfriend at our weekly Dungeons and Dragons session.
We'd been dating for all of two weeks, and had several awkward fumblings where he couldn't stay hard for the condom and would roll over to sulk, and I was getting fed up. He was a virgin too, but he wasn't the only frustrated party in the bed, and I was trying to be supportive but he was having no part of it. I was at the end of my rope, and called my friend to go hang out and bitch. I still lived at home, but she was married and lived with her husband and two kids, so I'd stay at their place frequently. When I got over there, I was greeted with a large bottle of Boone's farm and a bong hit just for me. I griped it out, got ripped, and we started talking about solving my problem. She (and her husband) had made it quite clear before that he was available if I was interested, and I'd engaged in kisses and fumbling with him but nothing more. (We had an unusual friendship, to say the least.) At this point, I was super frustrated, and the alcohol was changing my attitude on the matter from "Isn't this odd?" to "Why the fuck not?"
Her husband came home from work to find a plan hatched and two tipsy girls with devious grins. He was game, so we took the party to the bedroom. Even fortified with liquid courage, I was nervous, but I really really wanted to fuck. There was some kissing between the three of us while clothes came off. I remember sitting on his face kissing her while she rode him for a little bit (I didn't want to go first because I'm a dork). I was on my back when he entered me for the first time. He was big, but it didn't hurt because I'd been masturbating for years. Honestly, it was a bit underwhelming at first. It totally got better though, and we went through a few positions until I ended up on top of him. I didn't come, but I got pretty damned close.
The next day I broke up with my boyfriend. I didn't tell him what had happened the night before. I never slept with my friend or her husband again, and we drifted apart eventually. It was nearly a year before I had sex again. My second boyfriend was awesome, and we fucked like nerdy rabbits. I wouldn't change a thing, except maybe dumping the first boyfriend sooner. He was a tool.
How it went down: I attended a small liberal arts college in the south, and I ended up pledging a fraternity my freshman year. He was the president of that fraternity and three years older than me. Once a year the chapter would have this long, drawn out ritual that ended with the incoming pledges being assigned a "big brother," an upperclassman in the fraternity who would take the younger pledge under his wing. After the ceremony it was tradition for the big brothers to take their "little brother" back to the fraternity house to drink and whatnot. At one point in the night, we ended up going to his room to get some ice, which somehow turned into a slightly drunken awkward kiss that transitioned into slightly drunken awkward man-on-man action.
Partner: Then, she was the receptionist/dispatcher at my work. Now she's my wife. I didn't discover this till later, but she's three years older than me.
How it went down: She joined the company about a year after I did, I was in and out of the office a lot, because my job was mobile, so I'd stop and chat with her whenever I went by. She was fucking gorgeous, huge tits and whip-smart and funny. Me, being at the time, a fat, bespectacled nerd with a serious self-confidence problem, immediately thought "She's too good for me" and masturbated furiously to her image from afar but never made any moves on her for months. But we talked, laughed and, when my job gave me long breaks, I would keep her company while she wrangled the phones.
Conversations soon led us to discover that we had the same career plans (we both wanted to be cops) and just
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