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Teen first time sex story

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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.

Partner: 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 , 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.

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?

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.

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 when I had barely wrangled up the gusto to ask "maybe we should train together some time?

The run was scheduled for friday night, at the university campus next to her house. I got lost. Like, really lost. We were supposed to meet at 9pm we both got off work late and I didn't get there till closer to She was good-natured about it, and off we went, running around the track at the university.

At this point, I really didn't notice that her eyes were pretty much boring a hole into the crotch of my running shorts. And I really didn't pick up on the three times, she got super close to me and asked me whether I'd had any girlfriends no , or had anybody kissed me no or whether I had anyone I had a crush on at the office her, but I wasn't going to admit that straight out, so no.

To say I was an oblivious sap would be an understatement. After the run, she brought be back to her place, which was really a basement room she was renting, and fed me pie pumpkin, this was Thanksgiving weekend , and basically, now that I have the benefit of hindsight , chatted me up for two hours straight, inching closer and closer to me as the minutes passed she had started out on the opposite couch, but then by the time things came to a head, she was sitting at my feet with her head in my lap.

It wasn't until this point that I realized what she was after, and to say I had no idea what to do would be an understatement. I remember staring awkwardly away, trying not to burn holes in her cleavage, making vague "I'm not sure about this Thankfully, I was in the hands of somebody on a mission, who was not even going to let the vague discomforted of a horny, unsophisticated year-old virgin stand in her way.

I later found out that this mission was due to the fact that she and the other receptionists had been speculating on the size of my penis for months.

This is when I discovered, low and behold, I was good at touching. Watch lesbian porn, everyone, they are good teachers.

Either way, she initiated everything, from pulling my clothes off to climbing on top of me. I was too lost in a state of delighted misbelief to do anything useful.

I seriously thought I was dreaming. Up until, mid-act, my brother calls - and me, making dumb virgin moves - actually picked up. Hot beautiful girl raises eyebrows.

I drove home shortly after, wondering if she had slipped something into my pie. How it went down: For the longest time I couldn't figure out how to use a tampon so I went to the school nurse and had her show me how.

Then I got overzealous and decided to start using a Diva cup. My boyfriend was hanging out with me while I was trying to work it in. I couldn't get it in and was frustrated and on the verge of tears when I decided to have him help me stretch out.

It was completely unromantic but he was totally into it and then neither of us orgasmed because I didn't need us to orgasm in order to get the Diva cup in.

Poor guy. Things got better later of course. Location: Air. I couldn't afford anything else and was already in a shitty apartment in a shitty neighborhood after being told I could not stay with my parents for a summer between college semesters.

The room was incredibly tiny. It was also in a hot city in the South in the dead of summer, and we did not have air conditioning.

All of this will play into the saga. How it went down: He was my boyfriend I'm a girl , and also a virgin. Having sex on an air bed is at best a calculated risk, and at worst a complete and utter shitshow.

This was the latter. Both of us were virgins, and he got a little Because of the previously mentioned heat, we were both gruesomely sweaty this will come into play later.

We struggled a little bit with the condom and subsequent insertion, as novices are wont to do, and he started going to town.

He must have thought that the more athletic the thrust and the wider its range of motion, the better the sex. So the air bed was rockin and rollin, when suddenly he thought it was a good idea to try to put his hands under me during a particularly hearty thrust.

We lost our balance a bit and shifted to the edge of the bed, which as any experienced air bed user will know, caused it to tip over completely, ejecting us from the bed.

I heard his cries of anguish and stood to help him, but because his body had tracked sweat across the floor, I slipped, fell back on top of the air bed, and popped it completely.

It didn't hurt for me at all, and we went on to have a pretty fulfilling sexual experience together. At his place. On a real bed. Anyway, I love trotting out this story when sharing worst experiences with sex.

Age: I was 16, he was 17, and I felt like a goddamn badass. Location: Rural Pennsyltucky, against the upstairs wall on his divorced mother's condo's hallway, and because she wasn't really a person, it was lined with white shag carpet, and why this matters will soon be clear.

How it went down: I was an emerging poet who loved and dated a boy for over a year just because he was the lead singer in a band and this is what's more important wrote the lyrics to all their songs.

His mom—a local public high school English teacher who wanted desperately to be a writer, and with whom I hoped to connect so sweetly with that we'd go see Charles Dickens' plays together at Christmas, both of us wrapped up in scarves she'd knitted, or else we'd take bus trips to New York City just to smell the public libraries—hated me.

Luckily, she hated Pennsylvania more, but before leaving for a week-long vacation in the Florida Keys with her overweight Match.

To this day, I've never been able to find these condoms in a store again, which means that obviously way back in , his mother must've ordered them specially from an online porn shop, which is great fun to think about!

Chris and I were, as you might well guess, completely disgusted and freaked out, but we were also seventeen, so after striping one another bare, we began to have sex the only way we knew how: the way they do it in porn, with my back pushed against a wall, my legs wrapped around his waist, and Chris thrusting anxiously into me with unparalleled awkwardness and noise.

I began to bleed—just a little at first, and "Keep going," he said, "don't worry! We stopped having sex to try and clean the carpet, but the wet paper towel only smeared it and made it worse, and then we decided, Well, fuck it then, and resumed our former position, except now Chris' hands were bloody and wet from all the failed cleaning and we smeared it all over the wall.

I came, which is perhaps what's most surprising here, but we spent the whole rest of the week repainting the hall, scrubbing the carpet with every kind of "sit and wait" foaming cleanser available from our small-town hardware store, and every time I was over, we'd return to the hallway to neurotically examine the spot from different angles and in different light.

That should preface how my first attempts at sex went. 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.

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. My gynecologist still comments on how strong my weird vagina is, but figuring out ways to relax myself has gotten a lot easier.

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 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.

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. The best part is the stupid playlist he had on. Literally while he was inside of me, 'Whatever You Like' by T.

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. 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.

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. 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. 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. 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.

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