#1 01-09-2012 10:18

Amy881
Baby Bimbo
Amy881
Registered: 01-03-2012
Posts: 129

Funny/awkward stories about your first time :)

I loved reading through the "funny/awkward stories about having your period" and also noticed a few people giving advice to a girl about her first time having sex so I thought why not make a thread about funny/awkward stories about your first time having sex? lol

I guess fairs fair so ill go first... its not really funny but it was a bit awkward... i was 16 almost 17 (i know i was a little later than most but i was a little scared because someone told me that it really hurts the first time!) and we didnt really have anywhere to be alone so it was in his parents car when he borrowed it for the night, it was in an empty parking lot of some empty building on the edge of town not really sure what it was... anyway we were in the back seat but it was a really small car and it was so awkward to move around and we could barely fumble around enough to well... get in the right spot wink anyways after he started doing his thing i had my eyes close cuz i was scared about pain lol and i didnt see the security guard coming up to the car and tap on the window... omg we were so scared we'd be in trouble with him or the cops or our parents but the secutiry guard just told us that we couldnt be there and had to go away. We were so scared after that that we didnt try again for like two months lol. oh and i didnt really have much pain after everything i heard so i was happy about that smile

edit:  as someone suggested feel free to share funny stories about other times besides your first wink

Last edited by Amy881 (01-09-2012 13:28)


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#2 01-09-2012 11:43

Xenita
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Registered: 09-28-2008
Posts: 2187

Re: Funny/awkward stories about your first time :)

Haha, your first time sounded eventful.

I'm afraid mine is boring.  I was 16, he was 22.  He was also a virgin, with a 4 and a half inch c*ck and a tight foreskin... go figure, the whole thing was torture.  It was in my parents house, on their sofa.  I laid there, pretending it felt good and then afterwards, we laid there and I thought to myself "...is that it?"  He lasted for around 20 minutes, since he took breaks here and there but it was really an awful experience.  I went off to be on my own for a while afterwards.

I'm happy to say my current partner is much bigger and average and performs very well...  Thankfully.  No more boredom for me.

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#3 01-09-2012 13:13

Ehly
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From: Sweden
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Re: Funny/awkward stories about your first time :)

Isnt funny stories about sex more fun than just about the first time? We have it on another forum Im on, hilarious!


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#4 01-09-2012 13:26

Amy881
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Amy881
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Posts: 129

Re: Funny/awkward stories about your first time :)

Ehly wrote:

Isnt funny stories about sex more fun than just about the first time? We have it on another forum Im on, hilarious!

sure! thats a good idea lets her 'em!


~ Amy <3

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#5 01-09-2012 16:23

MissNoirCherise
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From: Oxfordshire, UK
Registered: 04-23-2008
Posts: 4972

Re: Funny/awkward stories about your first time :)

My first time was boring and I swear it only lasted a few minutes. I barely felt it and really it was a huge dissappointment. I waited 18 and a half years for that really?
I had more fun experiences since then.

One time I was having sex with this guy then he go like emotional and was like I cant do this and told me he was infertile... I was like hmm /wtf? Why is that a reason to not have sex. Anyway he was a nice guy so I was like "It's fine don't worry" Then we went to sleep. He also told me not to tell anyone. Next day I am in the kitchen my friend (also the guy I sort of slept with's friend) Came in and was lauging about how he had been told he couldn't have children and thats why we couldnt have sex.
Why it was such a huge deal I didn't say anything I'm not sure because he went and told everyone himself.


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#6 01-09-2012 16:53

KanameGackt
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KanameGackt
From: Sibiu
Registered: 03-30-2009
Posts: 1057

Re: Funny/awkward stories about your first time :)

Oh well, I was on my period lol and it hurt not only because it was my first timeh , but because of that thing too and after that we both discovered that my pants and his underwear were all stained with my blood
He said "Don't worry, I can get it out with Vanish :]"
I had a pair of very light short jeans so he started scrubbing them with some Vanish solution... which only made the blood pink, but it would still not ... vanish lol.
So much for his liquid Vanish >.<
So it was already late and I had to go home 'cuz my dad would kill me. He gave me his sweater which was a very long one and covered my jeans. He's much taller than me and i think that saved me for giving an explanation for my bloody jeans tongue
The next morning I was home alone (thanks god!) and I washed my jeans and let them dry along with other clothes, so my mom would not realize that I specially washed those jeans(she would've find out, because i NEVER wash clothes tongue)
And I washed them so hard and so much that the skin from the back of my finger went off -.- I had a "living" memory of that day for long, and it was on my finger...

Last edited by KanameGackt (01-09-2012 16:54)



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#7 01-09-2012 17:37

Miss Lacy
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Re: Funny/awkward stories about your first time :)

I lost my virginity not too long ago. I had done oral stuff with guys before so being naked and all was nothing knew to me so when we started stripping, I just looked at his d*ck and thought 'Oh my god, is that all?'. He looked a little less than average. But kudos to him, he did a good job and I really enjoyed myself! Just shows you don't need a big 'un to get the job done.


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#8 01-09-2012 18:14

Kinkymuffin
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Re: Funny/awkward stories about your first time :)

I had an argument with him during my first time. Rediculous!


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#9 01-10-2012 06:11

Amy881
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Posts: 129

Re: Funny/awkward stories about your first time :)

kinkymuffin wrote:

I had an argument with him during my first time. Rediculous!

really? what about if i can ask?


~ Amy <3

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#10 01-10-2012 06:38

Rayek
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Rayek
From: Notre Dame
Registered: 03-08-2010
Posts: 583

Re: Funny/awkward stories about your first time :)

I had been dating my boyfriend for about 6 months before our first time.  We did quite a bit leading up to it, but hadn't actually did the big IT for a while. 

We tried it in his parents car, but we both got really nervous and stopped before it actually happened.  A few days later we ended up doing it in my living room while my step mother was sleeping.  It was nice... I was kind of lucky, he was a great guy (ahem and well endowed).  Even now, 17 years later, we still talk a lot.

The only odd moment was after it was all said and done, he asked me if I was a virgin.  It kind of hurt my feelings, though he didn't mean for it to.  Made me feel like he thought I was some sort of slut at the time though... you'd think, if we waited for 6 months before doing anything... bah, anyway. 

The act itself wasn't really difficult or weird...  we just sort of... mixed well.  Hormones, instincts, not to mention the months non intercourse practice we had that led up to it... everything worked well and we were both pretty darn satisfied without ourselves after wards.

Mind you... I didn't find out until about a year and a half later that we missed the most exciting part of sex for the woman (imo), not only the first time, but the multitudes of times after that.  Neither of us knew about the clit.  (That's a little embarrassing, but hey, I was young and we didn't have the internet).


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#11 01-10-2012 07:03

Florallover
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florallover
From: Tiny land called Malaysia
Registered: 04-20-2008
Posts: 11419

Re: Funny/awkward stories about your first time :)

I'm not sure that I should go into details, but we're both virgins when we're first at it... He didn't know that he needed to do foreplay to get me ready and so it really hurts, he is a big sized man while I'm a thin, petite girl... By the time he goes in, I'm already crying in fear and pain and then he stopped...
He took me to see a doctor when I'm still in pain after 4 days...


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#12 01-10-2012 09:48

Typhani
Big Breasted Bimbo
Typhani
From: England, living in Germany
Registered: 07-15-2008
Posts: 23323

Re: Funny/awkward stories about your first time :)

The first time I got naked with a boy, he tried to ease the tension by joking "It's not normally yellow, I am wearing a condom". I did that thing where I say "What?" even though I heard him perfectly the first time, so he had to repeat it, and the tension rocketed to about 5 million, hahah.

We did not manage to have sex on that occasion... I thought it would just slide in - it did not, probably due to said tension.

Btw yeah I guess it was a coloured condom, and I learnt later that he was in the habit of always putting a condom on before coming to see me, due to the delightful reality of Leakage.

Last edited by Typhani (01-10-2012 09:49)


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#13 01-10-2012 13:05

Amy881
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Amy881
Registered: 01-03-2012
Posts: 129

Re: Funny/awkward stories about your first time :)

Typhani wrote:

... and I learnt later that he was in the habit of always putting a condom on before coming to see me, due to the delightful reality of Leakage.

lol sounds like a compliment to me wink


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#14 01-10-2012 17:45

Sleapyhead
Dandruff Bimbo
sleapyhead
From: Gotham City
Registered: 03-29-2008
Posts: 4543

Re: Funny/awkward stories about your first time :)

Everything was pretty awkward and terrible about my first time. The guy meditated for 20 minutes before anything happened so that was the extent of the foreplay... nothing. I just kind of sat there watching him not knowing whether I should be quiet or talk. I also never told him I was a virgin because it was embarrassing for me... and that was incredibly stupid of me. So as soon as he's done meditating he just pounces on me and starts ripping my clothes off, and I'm like wtf half liking it-half trying to slow him down a little. And then he just goes and rams his c*ck in me like he's expecting my vagina to be a pocket pussy or some kind of sex toy contraption... and that is when I screamed. I screamed on the top of my lungs every word I could imagine. Then I screamed stop. And he stopped.

So my first time lasted, Oh I don't know, 3 seconds. I couldn't walk and bled for like 3 days. I probably should have seen a doctor because I'm pretty sure he tore something.


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#15 01-10-2012 18:01

PirateHookur
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From: Anywhere with gin
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Posts: 532

Re: Funny/awkward stories about your first time :)

I laid there and hoped for the best.    didnt come.  took two tries for anything to happen. The first time i didnt feel anything, and he tried a 'different' position by sitting on a chair and dropped me.


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#16 01-10-2012 20:59

Kinkymuffin
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kinkymuffin
Registered: 03-28-2008
Posts: 98

Re: Funny/awkward stories about your first time :)

Amy881 wrote:

kinkymuffin wrote:

I had an argument with him during my first time. Rediculous!

really? what about if i can ask?

I was complaining about how much it hurt, and said it hurt all girls their first time (not necessarily true but it made me feel better about the situation) and he goes and argues this point while i'm lying there in pain neutral And then he continues to throw me into shapes insisting he needed to break the hymen even though i knew full well that had broken years ago, disregarding the tears running down my face.


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#17 01-10-2012 21:08

Amy881
Baby Bimbo
Amy881
Registered: 01-03-2012
Posts: 129

Re: Funny/awkward stories about your first time :)

kinkymuffin wrote:

Amy881 wrote:

kinkymuffin wrote:

I had an argument with him during my first time. Rediculous!

really? what about if i can ask?

I was complaining about how much it hurt, and said it hurt all girls their first time (not necessarily true but it made me feel better about the situation) and he goes and argues this point while i'm lying there in pain neutral And then he continues to throw me into shapes insisting he needed to break the hymen even though i knew full well that had broken years ago, disregarding the tears running down my face.

god what a selfish jerk sad


~ Amy <3

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#18 01-11-2012 08:59

Eleintje
Fugly Bimbo
Eleintje
From: Belgium
Registered: 08-22-2008
Posts: 6144

Re: Funny/awkward stories about your first time :)

Hurt like hell. We tried for a few minutes and then I couldn't take it any more and started crying. He stopped, and I was so horrified I just sat there staring at nothing, he had to shake my shoulders to get me out of it blebl. Then I turned around and there was a massive blood stain on his sheets, and I was even more horrified and started crying again. He was really sweet though. He comforted me, told me everything was ok, flipped the sheets and told me to lay down and just hugged me smile. After a while he gave me some of his clothes to sleep in and I stayed over.

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#19 02-01-2012 22:14

Model2oo9
Virgin Bimbo
model2oo9
Registered: 09-29-2009
Posts: 40

Re: Funny/awkward stories about your first time :)

My Experience happened not too long ago smile You see I was with this guy named David for about 3 months and everything was going well we were really in love and stuff but after the 3 months he broke up with me saying it wasn't what he expected and stuff. I was a bit shaken for about 2 weeks but thn I wanted to stay friends with him. So even though it hurt to talk to him I did just to keep in touch. We were mocking each other and laughing a lot. We remembered the good times we had and said decided to be a little more thn friends when he proposed the term friends with benefits. I was up for it as I felt comfortable around him as we were on the oral stage. The only problem was the location...

We decided to meet in a secluded apartament and do it in the corridor where the stairs are because noone uses them. I was 15 and he was 17 and we did the foreplay and had fun cause thts what its all about smile So there we were getting ready and he opened the condom packet and he but the condom to his mouth... (facepalm) I asked him what is he doing and he said blowing up the condom........... I couldnt help but burst out laughing big_smile I showed him how to put it on and he slowly went into me. At first I couldn't feel anything but then I felt this sudden urge of pain. I was lying there and him on top of me not moving because he knew that if he moved he wud cause me pain. He was very sweet asking me if i'm ok and kissing me to ease the pain. After about a minute i told him to try again and this time it didn't hurt that much. He didn't last long maybe for 10 mins but right after it he took care of himself and i was there in the corner needing a hug... Awww well after it we went to a chipper and talked about the experience big_smile Till today I'm still laughing about the condom 'blow up' big_smile Btw. We are meeting soon to repeat the experience smile


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#20 02-06-2012 13:28

Marsychan
Baby Bimbo
marsychan
Registered: 06-06-2009
Posts: 80

Re: Funny/awkward stories about your first time :)

My first time I was quite drunk, but I still remember it. My friend walked in on us so we decided to move down to the beach, but then the tide came in. It was actual a really funny experience and when we finally found a place to do it, it was pretty damn good.

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#21 02-06-2012 22:30

LoveYa1
Acne Bimbo
LoveYa1
From: My comfy bed :)
Registered: 03-25-2008
Posts: 5808

Re: Funny/awkward stories about your first time :)

Me and my boyfriend were once in my mums car, we were just driving around before I dropped him off at the train station. We were bored so we went and parked in a huge car park by my local cinema. We both started to get rather horny but I didn't want to have sex as it's quite a public car park instead I start wanking him off. I saw car headlights next to the car but didn't think anymore of it and carried on. After he had finished I gave him some wipes my mum keeps in the car to clean himself up when he started messing around with it. We heard some laughing and then the next thing you know a car drove past us and they beeped and waved. I didn't know this people when it dawned on me that they had seen the whole thing in the wing mirror of the car. My boyfriend then said "I feel uncomfortable can we move space" baring in mind what we had just done.... in my mother's car.

Looking back on it it was rather funny but at the time we were both so embarrassed. My mum still doesn't know about this.


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#22 03-05-2012 19:40

IvyJane
Old Hag Bimbo
IvyJane
Registered: 10-19-2008
Posts: 610

Re: Funny/awkward stories about your first time :)

Heres an embarrassing one, I would say this is in the top 3 for sure.
A few months ago I was at a party on campus at my unversity. Everyone was pretty drunk and I ended up spotting this really hot guy. So after flirting with him the whole night we end up back in his room. Alot of the details are pretty hazy from here on out, but unfortunately I remember this.. We started having sex, and I ended up queefing. I was absolutely mortified, and I wasnt sure if he thought I had farted. So I was like OMG I am soo sorry D: Thankfully he was cool enough and just said oh, its okay, dont worry about it. I was drunk enough at the time that I didnt let it ruin my night, so we kept going at it. I woke up the next morning completely embarrassed again, and then some. Unfortunately I still run into him in the halls once in a while, we havent talked since that night, but every time I see him I cringe.. lol

PS. I know drunk hookups are wrong, I learned my lesson. Please dont lecture me!


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#23 03-05-2012 19:53

IvyJane
Old Hag Bimbo
IvyJane
Registered: 10-19-2008
Posts: 610

Re: Funny/awkward stories about your first time :)

Heres another kind of funny one while Im at it..
I was at another party at my boyfriend at the times house, everyone was pretty drunk, once again. (Im not completely sure if this is what happened, but this makes the most sense to me as to how I ended up in this situation) I was feeling kind of tired, so I went in my boyfriends room to lay down, however one of my boyfriends close (and hot) friends was already laying down in the bed. I didnt really think anything of it since I was pretty good friends with him too, so I went and layed down on the bed too. About 10 minutes later my boyfriend comes in (note, he doesnt care that we're both laying on the bed) and he lays next to me. So I half jokingly/half honestly say, we should have a threesome! So then to my shock my boyfriend reaches over and starts taking off his friends jeans. I then realized holy $@*% this might actually happen! It kinda freaked me out and I suddenly realized that maybe I didnt want to be part of a threesome, so I ran back out to the party lol With the guys close behind of course!


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#24 03-05-2012 22:16

LadiiEva
Fugly Bimbo
LadiiEva
From: FabuloSity
Registered: 05-18-2008
Posts: 6366

Re: Funny/awkward stories about your first time :)

Why did I read this thread title as, Funny/awkward stories about your first NAME??


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#25 03-05-2012 22:56

SummerDawn12
Bad Breath Bimbo
SummerDawn12
From: Hello Kitty Heaven
Registered: 07-19-2010
Posts: 2568

Re: Funny/awkward stories about your first time :)

Haha. Wow, all of these are just so hilarious. Seems like most of the awkward stories are either dealing with all the pain or their boyfriends small d*ck. lol But I don't really have an awkward or funny story.
My first time was pretty awkward, I mean whos isn't? Most of everyone I know had a weird first time. It wasn't because he had a small d*ck or anything, it was mainly just facing the fact that we were doing it for the first time. tongue


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