NS, tell me the story of when you lost your virginity

and i might share :D

So it all starts off in Puerto Rico, I was there visiting my sister who was attending the university there and one of my friends Søren (Swedish and very very wealthy) was staying at one of the upscale hotels in San Juan. Anyways my sister had night classes on the weekend so i ended up meeting Søren and booking the Presidential Suite at The W for 5 days. (was roughly around $8,000) So for the first couple days we attracted a lot of attention because you are basically treated like kings and people aren't used to seeing a couple young adults blow so much cash. Anyways there was this girl who was talking to me for the first couple days we were there and i never thought anything of it. I got to know her a bit better and her name; Megan and we hung out at the pool and stuff like that, well one night me and Søren go out to a party at the Don Q brewing factory (Puerto Rican Vodka) and well we get fucking destroyed. Since we have a monster room with 6 bedrooms and our own pool we decide to invite roughly around 20 people from this party back to our place to continue the party and with me not speaking that much spanish i had no idea who i was inviting or if they were coming so there ended up being a lot more people there then we had anticipated. So our car pulls up to the hotel and about 6 of us stumble out with vodka bottles in our hands not knowing how to get back to our room. So we make it to the common area you could call it and i see this Megan girl sitting on one of the sofas at the bar. Drunkenly i think i called out to her to join us and anyways after some time talking we head back up the the room. So at this time i think its around 1:30 and 2:00 am and there seems to be a lot of people in my hotel room. So we all decided to take the party to our pool and we all jump in. Im pretty sure there were a bunch of naked people in there but between trying not to drown and hold this Megan girl i couldn't focus on everything that was going on. At this point Søren grabs our complimentary bottle of champagne pops the cork and starts to dump/spray into the pool. From this point on i don't really remember that much but the next thing i know me and Megan are out of the pool and looking for my room, it turns out most of the rooms were already occupied so we stumble over to the balcony... We took a seat beside each other and started to kiss, well i imagine one thing led to another and then the next thing i know is I'm wrapping my tool and we start to do it on the balcony. At this point the alcohol is flowing through me and i am ridiculously drunk. I don't know how long i lasted but we ended up passing out on the balcony naked. Well it turns out the balcony faces the common area and bunch of other rooms. (our room is basically the rooftop of the hotel so very visible through windows of other rooms and what not.) luckily it was super late and not many were in the area but the next morning i was woken up by a phone call from the front desk with complaints about a couple having sex on the balcony. So at this point i am like what the fuck happened??? As I walk through my hotel room i see people passed out everywhere and broken bottles and throw up all over the place and then i see Søren passed out of the floor with some girl in his arms i wake him and tell him I'm going to the beach to relax and try to get rid of my wicked hangover. I start to make my way out while kicking some of the randoms out of my room. Over the next couple days I blew off this girl i slept with because i was somewhat embarrassed and didn't really want to have to explain myself. Regardless the time comes when i have to come home and so i pack my bags and head to the airport. On my flight back home i have a lay-off in Chicago, and I never thought anything off it. Well i should have. I end up having one of those seats in the middle of the isle with seats on either side. I like to be early and board as soon as possible so I am one of the first on and i throw my bags in the overhead and take a seat and put my iPod in and sit back. As more people start to board I see this Megan girl coming down the isle... I'm think fuck fuck fuck fuck fuck and then a sudden calmness comes over me and i reassure myself that there is no way she has a seat by me. Well as she makes her way father down the isle I kind of begin to sweat and duck my head behind the seat in front of me, well 30 seconds pass and the next thing i know she is looking down at me and then back up at the seat number. FUCK right? It turns out she lives in Chicago and she had the seat right beside me... She asks me where i have been for the last 3 days and I made up the lamest excuse i could think of and out came "I was playing chess" well that wasn't the answer she was looking for and for the next 8 hours confined to our seats we didn't say a word to each other. It was the worse 8 hours of my life but the previous days were well worth it!

so me and a buddy went to watch a basketball game at another school and we were just hanging out there and my friend was talking to the girl he knew so i start talking to her too. well after a while we end up like joking about stuff related to sex and basically the girl was like "i'd like to try that" and sarcastically i said ok lets go do it and she thought i was serious so all of a sudden me and her are walking out of the gym and i take her through the parking lot and before i know it I'm banging her in the backseat of my dads truck. i lasted longer than i thought i would (like 10 minutes) so then we're done and get dressed and get out of the truck and my buddy and another dude were walking towards the truck and saw us getting out.

sparknotes i fucked a girl in my dads truck in a school parking lot and then got high fives when i got out of the truck

Anyway, there was this woman, idk, in her 20's that worked for us. I remember, she lived on the top floor in this room by the stairs. I was 15.

I am an athletic person, as I was back then. When I couldn't run outside (raining or something), I'd lap the stairs. She would always seem to watch me, and I admit she was pretty fine. My sister knew about this, and she kept urging me to do it with the woman.

Finally, one rainy day I was pretty far into my stair running and darn sweaty. She called me into her room, and I went, knowing what would happen. It was odd, because she clearly wasn't a virgin as I was. She kinda told me what to do, but it was great nevertheless. I lasted for a while and she was happy about that. So, I was in her room a lot those rainy days. We never really did anything else, and then when we moved to Vienna, i never talked to her again.

and that's my story.

i had been hooking up with this girl in my town on and off... i say on and off because i went to boarding school and was almost never in town. we'd basically hook up multiple times during breaks and once or twice if i came home on a weekend. she wasn't that hot, but i could care less, i was more in it for the practice so that when i met a smokeshow i could show off my moves. anyways, at some point she told me she wanted to lose her virginity, i said that i did too. she suggested that we have sex, and of course i agreed. multiple hookups later, we still hadn't fucked. i was getting impatient so i told her that if we didn't have sex i wasn't gonna hook up with her anymore. she said okay, bring a condom next time you come over. two weeks later i was back in town. i drove back in the morning, then took a 3 hour boat ride with my homies down the charles river. we borrowed my friends 21 foot speedboat and gunned it past the rowing regattas, ate dinner at legal seafoods, and then we drove back in the sunset. she texts me on the way back and asks if i'm coming over tonight and if i have a condom. i lied and said i'd come over but i don't have a condom (i didn't have one, but i could've gotten one easily). she tells me that it's okay because she recently got off of her period, so i'm fucking pumped. i head over, we chill for a little bit and then things start getting heated. next thing i know, were both naked and she's blowing me. she asks me if i want to fuck and of course i said yes. i try to go inside of her, it DOESN'T FUCKING FIT. i go soft after trying 2 or 3 times cause im somewhat nervous, so she blows me again to get me hard and i try again. this happens like 8 times, eventually it works. i take it easy cause she's a virgin and cause i don't want to blow my load inside of her with no condom. 30 minutes of fucking and i haven't came yet, she tells me i need to go home (it's 4:30 in the morning at this point), sucks me off, and then i walk out the door.

walked back home to a sunrise and saw a family of coyotes on the way back straight chilling on the road, walk of shame? more like walk of fame.

This happened at the start of last summer. I met this guy on a school trip to Montreal in April, and we hit it off like I didn't think was possible. I pretty much fell in love in a matter of a few days. When I came back home (I live just outside of Toronto), we stayed in close contact, skyping every night, doing the long distance relationship thing. The next time I was seeing him was in June when we planned for him to come to the end of the year formal with me. That's just about 2 months away from each other.

Now in a long distance relationship with no physical contact its easy for the imagination to get away with you. Basically we planned to do the deed while he was visiting because it seemed like the perfect opportunity and we were pretty seriously head over heels for each other.

He arrived, and the last night he was staying was the formal + afterparty. We had been sneaking around hooking up for the past few days but we hadn't had sex...and time was running out. The dance was great, we got all dressed up, took pictures, blah blah blah, the whole shebang. Once the formal part was done, we took the limo back to my friend's house, who was hosting the afterparty for our grade. We chilled around for a bit, I introduced him to my friends, and then we were like alright let's get going because this party is our last chance.

He grabbed the condoms and we went downstairs in search of a room and managed to find one off of the laundry room. It was a double bed and it was the best we could do, except we realized the door did not lock AND it opened out, making it impossible to guarantee security. So I grabbed my friend and her boyfriend and basically they were in charge of guarding the door. Except the problem was that a guy in my grade had some sort of evil vendetta against my friend's boyfriend and he and his drunken comrades from the hockey team (assholes, every single one of them) had rocks in their hands and were on the hunt to beat him up. A few of my other friends made their way into the laundry room and were promptly informed as to what was going on in the bedroom the next room over. So the guard was set up except for the fact that there was a mob combing the house looking for my friend's boyfriend.

Clothes were off, all that fancy schmancy stuff that happens and literally right as I was about to lose my virginity, we hear screaming and yelling coming from outside, and tons of voices chanting "SANDSTORM! SANDSTORM!" (the significance of which I do not know to this day), looking for my friend's guy (let's call him John). John and my friend channelled their inner Anne Frank and ran to hide in a crawlspace as the mob managed to break down the door into the laundry room to look for them. A couple of my friends were chilling, pretending my friend and John weren't anywhere nearby. Of course, the next place they wanted to look was the room where I was lying, clothes off, and silent with my guy from Montreal.

In order to scare off the mob, on of my friends screamed "DON'T GO IN THERE, KATE'S HAVING SEX" which made for a very audible silence in the room outside the door. The drunken hockey players stormed off and we were so freaked out that he had "lost interest" and we needed to repeat everything we had already done in order to finally do the deed.

It was terrifying but hilarious to look back on and though we're not together anymore, sharing the experience of listening to a mob try and get into the room where you're about to fuck someone for the first time makes for a good laugh.

Sparknotes: long distance relationship, we had one chance to bang at a party, my friends were guarding the door, mob tried to break in, friend yells to the entire party that i'm having sex, mob leaves, we finish awkwardly