so my girlfriend spent the night at my place last night (not the first time she's done it ) - last time we didn't have sex since I didnt have a condum (stupid but whatever), i slipped in the fingers and she gave me a handjob .
now (like 3 weeks later) she spends the night at my place again , this time I did have condums - we did a lot of foreplay, kissing/body rubbing etc. for probably 15- 20 minutes.. i noticed her pussy was really really really tight (my fingers barely fit - no lie ) , she's 20 years old and she's probably around 5'8 and is VERY VERY skinny, she's size 00 . so it was awkward because when I got the condum and everything and tried putting it in , my dick WOULD NOT FIT IN. I had already tried a good amount to get her wet and loosen up but maaan she is tight as fuck it was a little emberassing .. she even tried putting it in and she couldn't either ... I don't t

we stopped trying after a little and kept on just kissing and all that stuff .. I got to say I was pretty let down - she didn't really care .

Has this ever happened to anyone and do you have any tips for next time? don't want this to happen again
dont even know if this is in the right section but it has to do with relationships so yeah.

LOL yes dude...

Losen her up with your fingers a little bit more. Depending on what position you were starting in also makes a huge difference in how easy it is to get it in....

You shouldn't have said you were let down. Firstly, it is obvious and therefore unnecessary. Secondly, it hurts her feelings. Realize that she's probably quite embarrassed, and possibly scared (I'm assuming she has no or very little experience, correct me if I'm wrong). Next time, ask her how you can make her comfortable, and do it. Focus on her, go down on her, whatever she likes. A good lover puts the sexual needs of his partner before his own. If you do this well, she will get to a stage of excitement where not fitting should no longer be a problem (unless she has a medical condition, which is highly unlikely).

Also, don't try to 'loosen up' with your fingers. Her pussy doesn't need stretching, her pussy needs pleasure.

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One of the most useful things you will ever learn about body language.

I didn't tell her I was let down ( i just was, mentally) , the only thing I told her was "wow you're really tight" hahaha. but yes I'm pretty sure you're right in the "possibly scared" factor - last time she slept over she had actually mentioned to me that she wants to wait till we're together for a lot longer (gay i know, but I went along with what she said - i knew we would be having sex sooner than later) . Then last night I told her "i have a condum" and she said to put it on but she didn't sound so sure , i even asked her twice "are you SURE?" and she said she's sure , so I tried putting it in and NOPE. i'm pretty sure it was a mental thing , after a couple tries I think the tip went in a little and she said it was gonna hurt a lot .
So you think I should just go all out on her? not used to doing that but it may be the trick . I remember last time she was not this tight idk why last night all of a sudden even my fingers barely fit..

Dude literally this same exact thing happened to me in high school....twice to the same girl...and then we never ended up having sex, it was awkward as fuck and it sucked.

Get some lube, keep it next to wherever you're banging her and then just rub it on your dick after putting your condom on and slide it in, you should be good.

Sorry that this happened to you, I know exactly how you feel!

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My Journal (from AFC to MPUA, still a work in progress)

Put her on her back and keep her legs in the air. It's said that missionary penetrates the deepest so try that. Is she a virgin or something ?

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she might think you're just teasing her with your moves well if there would be sessions in the future. make it happen!. DOnt think of yourself as a let down. It is a normal thing for first time sex in a fresh relationship.

any tips for making her loose up for next time? or are there good techniques for cases like these..

Go down on her. My tongue is a weapon of mass destruction lol get good with yours and she will be BEGGING for it.

Hey,

I exactly had the same situation like you had with my girlfriend ( she was virgin when we first tried to have sex. ).

At first I was really disappointed because I really wanted to have sex with her, not just because she was real hot, because I am in love with her.

After 1 hour of foreplay, I went into missionary which is the easiest way to get in , in my opinion and i tried loosening it up for like 20 minutes, only got one finger in, you could describe it as "butthole-tight". We ended up kissing and cuddling.

Second time , I slipped two fingers in, foreplay was longer than the last time , still it couldn't fit.

Third time , after 2 hours of solid foreplay, i got her wet as fuck, managed to get 2 fingers in, started loosening it up, for like 15 minutes, I could almost slip 3 fingers in without too much effort.

The moment started to happen, I managed to get 1/3 of my dick in, slowly started penetrating her, real slow ( it is possible that it may hurt for the girl a bit, but she'll let you know, then just take it slower.


After 5 minutes of slow penetration I told her to just relax , and slowly kiss her. She started to relax, and I managed to get my dick in 2/3 , i started to penetrate her a little faster, and thrusting a little deeper, and bam, we were having sex.

Don't get frustrated,
talk about it with your girlfriend.

It needs time, so just give it the time it needs. ( this all happened in 3 weeks. ) so it definitely needs TIME.

Goodluck, and a loving relationship.

-Will.
Communication is key.