First Time Sex Letters

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First Time Sex Letters
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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." —


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Penthouse Letters have covered a range of topics over the years. Here are the greatest submissions ever sent to the popular adult magazine.
"I never thought this would happen to me...", a line that is now classic thanks to Penthouse Letters, a section reserved in the popular adult magazine for stories. For many years these stories have been a staple of Penthouse, this is a list of the most popular scenarios readers have enjoyed.
Growing up in the eighties there were three magazines teenage boys wanted: Playboy, Penthouse and Hustler. Despite the name, Penthouse was always more Hustler versus Playboy. One area it differentiated from the others was through running section known as Penthouse forum where they printed sexy letters sent in by readers. These stories are and have always been accompanied with colorful photos of hardcore adult situations. The stories are supposedly real, but definitely embellished and in many cases, probably flat-out fiction. Regardless of true or false, these stories are fantasies for the reader.
Honorable mention goes to “Jailhouse Stories”. That’s right, this subject, a mainstay didn’t even make the list! Jailhouse sex stories go one of several directions; it could be a gay sex, guard sex, or even better, escape sex. In case you haven’t figured it out, the one common component to all of these stories is sex.
This list has everything ranging from chance encounters to multiple partners to painful situations. Grab your favorite beverage and for Christ’s sake, pull up your pants, man! This is a list of the greatest Penthouse letter subjects of all time.
“I never thought I would be into pain, but now whenever I smell leather I think of him.”
These stories typically fall into one of two scenarios; first one is that someone gets an appointment as a gift or suggestion. I guess this is the gift for the girl or guy who doesn’t do spa days. Anyway, the person is usually shy and conservative until they feel the leather hit their bottom. The second scenario is the “dating a dominatrix” situation. Many guys fantasize about, but are probably too scared to put themselves in this situation. According to the letters, those who dare are rewarded for their sense of adventure.
“I never thought it would happen to me, but seeing my High School sweetheart after 20 years…”
The old friend tale is often a coincidental encounter followed by “coffee” and then a Fatal Attraction type romp nearby. The good story tellers have a back story of how this boy (starting quarterback in high school) would never talk to her, but now she has finally had him and it was spectacular. At some point the tale may even turn vengeful (again, Fatal Attraction ) where the girl rights her wrongful past, leaving him naked and tied to a bedpost while she calls his wife (who just happened to be the head cheerleader in high school). Yeah, revenge stories are always the best.
“I’ve never been with another woman so you can understand my surprise when she took my hand and placed it…”
One of the more popular topics is lesbians, specifically first-time lesbians. The storyline is often that the girl is very shy and surprised by how fast she is turned on by her friend. Keep in mind this isn’t two men, these are women; the climate is sensual until of course she gets really turned on with a combination of candles, touching and margaritas. I don’t know what the Penthouse Letter phrase is, but I know in movies it’s known as the money shot!
“I never thought I would write a letter to Penthouse, but then again, I was never that into bikers until recently when…”
I don’t know why (maybe it’s the s
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