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Ok. I am a 20 yr old female college student and I have been dating this amazing guy. For our 6th month anniversary he is planning a big date and I am driving up to his apt for a few days after my finals (which is when our anniversary is) and I want to ‘surprise’ him by finally taking the next step.  I feel completely comfortable with him, with and without clothes on. He is amazing and although he has confessed that he wants to have sex (of course) he doesn’t want me doing it till I am ready and told me if I say we can only cuddle for a yr then that’s what we will do.  We met at our summer job, but during the school year we only get to see each other 1-4 times a month because our universities are 2 and a half hrs away. I am soon to move even farther away (20hrs) for a six month internship and will likely only get to see him once or twice in the 6mns (I’ll be missing both our 21st birthdays and our 1yr anniversary  :/ ). He is the first guy I have gotten to the point where I felt even remotely willing to remove clothing for and is my first really serious boyfriend, while I’m his first really serious girlfriend.  I don’t feel pressured to have sex with him and I want to do this before I leave. We have done Oral often now, and that is no problem, it has been great! But there are two problems with taking the next step-

Problem One- we are both virgins--- Honestly we don’t really know what to do. Yes of course we know the basic mechanics but the other things you learn with practice… well neither of us have a clue. I’ve done research but he doesn’t understand the need to buy lube (although we both agree we aren’t doing it till I am on birth control and then only with a condom also). What kind of Lubes are the best and such? What are your recommendations for taking this big step?

Problem Two- I am very very tight and he is pretty big--- If he puts more than two fingers in me the pain is bad, three it’s excruciating. We tried to just put it in (we were using protection) last time he was in town and when his head started to push into me I near screamed in pain. I know the biology behind it, but is there any way to make it hurt less? It doesn’t help that he is a bit gifted in that department. He is a smiggen longer than average, but a lot thicker than average. I’ve been told that’s a great thing when you are having sex, but right now it’s just a problem…. He has fingered me a lot, but he gets turned off when I am in pain and feels terrible so any ‘stretching’ sessions haven’t gone so well. 

My family and friends are pretty conservative so I don’t really have anyone close that I trust to ask for such intimate advice. I am hoping someone here will have some amazing advice. And ideas?

 

-Sammy

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I think it is so awesome that you're still a virgin at that age! Hmm, I don't know of any ways you could dramatically make the pain subside BUT you could try just using a lot of lubricant. I don't know where you live so I can't suggest brands but yeah I'd say to try that. Yes, it does hurt for the first time but after that you'll be as good as gold.  I know it is scary but as long as you two love each other very much and are 100% sure you really want to give yourselves to each other then I say go for it. Experience this big moment together. When he 'fingers' you, you could also try using some/more lubricant?  I'm 17 and I wish I still had my V-card. I don't know if what I've said will really help you but I hope it can spark a few ideas.
Best of luck!'
'
~Allora
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one answer... may not totally eliminate the problem but LOTS OF LUBE... 
i have been having sex for 3 years now regularly....and if there's no lube and i'm not quite wet enough it still hurts!. the good thing is its usually just that first time he goes in, then its a little easier every time after that.. i would definitely try fingering with lube and work your way up. and since you did mention he has more length than average, try a position that doesn't give you very deep penetration... i find even after 3 years sometimes when he goes in all the way (bcus he does also have some extra length) the tip of the penis will hit the cervix and boy does that ever hurt!!! 
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What she said!!!



If you are small or tight it will just take time and a lot of love and care from your partner on the way to getting comfortable, and lots of lube.



And hitting the cervix is quite painful, so my wife says. I was NOT super sized but in some positions I did hit her cervix. I say did because that's no longer a problem. I'm 71 and all those jokes about old guys really are true. In the coffee shop when an old guy gets up to go to the mens room and you hear his buddy ask if needs to borrow his magnifying glass ---- he ain't kidding.



It sounds like he really cares and the two of you have a good working relationship with your sexuality so you will be OK. We were all virgins once and we got over it. It amazes me now when I think about how little I/we knew when we got married but I figured out how to give her some good loving and eventually we had some great sex.



We also had no one to ask so we had to figure it on our own and as much as my wife dislikes magazines like Playboy, that's where I got a lot of good information. I am turned on by tiny breasts like my wife has so the pictures of girls with huge boobs and no vulvas didn't do much for me. Therefor I actually read the articles.
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i think its really cool that you were a virgin that long i was with my boyfriend for a year and a half and in the beginning it did hurt since he was pretty big in the department. and im pretty small for his size. it did hurt in the beginning and we had to do it several times for me to have it all the way in i dont know if you should just keep trying to slowly or try to use alot of lube hope this helped
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