Please take your caps lock off, and decrease your letter size, thanks

It's Not The Caps Lock--Rather That She Is Capitalizing Every Word In The Sentence which makes reading her letter very annoying and cumbersome. Please capitalize just the first word, please. Oh, and the "WTF" abbreviated or spelled out is not cool. :(

Anyway, welcome to the SI101 Board and its Forums. I hope you enjoy participating.

> There Was Alot Of Forplay

This is a good thing. Kudos to your boyfriend! It usually takes half an hour to forty-five minutes of making out and fooling around before a woman's "engine" is warmed up and arousal peaked. The time also helps the man!

> And He Starts To Penatrate. This Is When The Problems Started To Occur. He Would Get It In But It Wouldnt Stay. It Was Like I Was Too Tight Or Something. I Felt So Bad.

How far was he able to get? The full length of his penis? Part way? What part?

This is not at all unusual and you must not feel bad that your first experience did not go as planned. It often does not and for a variety of reasons, the most common being that the man is unable to penetrate at all either because of her discomfort or not being able to slide beside the Hymen. If he was able to fully penetrate then my guess is that he "fell out" because of the stroking and not being able to judge when he should reverse his stroking. If this happens to be the case, the problem is with him, not you.

If he was able to only penetrate a little, like the head of the penis perhaps up to the Corona Rim where the head joins the shaft, then most likely he was unable to get past the Hymen. Do you know if your Hymen is (partially) intact or has it eroded away over the years? Question: can you insert a finger?

Were you turned on and wet? Even if you were, it helps to have a lube available for the penis. Was he waring a condom?

Without knowing more, it is impossible to provide specific answers. All we can do with what we know so far is to offer conjecture. I'd not hesitate to try, again, and yet again. Practice is important and it takes a few tries before any couple becomes comfortable with each other and gets a "groove" so to speak. Here is an article to read:

HELP! S/He is more EXPERIENCED! To which I say:

To learn more about the art of Eros, please consult the Index:

--BEGIN HERE--w/a Partial INDEX of Sex Info 101 Sex Ed. Topics

I hope this is of help. Got questions?

Tightness would not be abnormal for a first time. In fact, none of what you're describing is abnormal for a first time. DON'T feel bad. You did NOTHING wrong. Believe him when he says it's alright, because it is.

One suggestion I would float: as many times as you indicate that he repeated 'are you sure?', he may have been a little uneasy. If he was, this could have contributed to the challenges. This, too, is alright. Everything you describe is normal for a first time between any two people. Just because he's done this before, that's not the same as having done it before with YOU. Everyone's different and part of the whole thing is learning each other-what works and what doesn't.

Don't take it so hard, it will be fine. Again, all this is normal, so relax and try to go with it and enjoy.

Hey Doc, the first time I read it it was all caps and used large lettering, which is why I asked her to edit.

Understood. I hope she replies and supplies additional information.

As I do, as well.
Being a woman, 5'2" I have found it helpful to put one of my bed pillows under my tushie (bum). It is hard to explain, but it tilts me up. Intercourse is learned, the desire we are born with yet the technique is each to their own.
That's the good part, practice. Always use a condom, make sure it is the right one for him and that it is on correctly. Also go slow once he is inside you, get the feel for how deep he is able to go and how far he can back out without actually losing penetration.

Yes, I understand you feel bad for not being superb at sex right out of the starting gate when you know nothing about it. Sounds silly, doesn't it. No one expects their first time, and subsequently their first time with a new lover, to be good. Never, ever apologise for what is not your fault. No one expects a virgin to know anything.

This is not your fault. There is nothing wrong with you.

You more than most likely still retain your hymen; a piece of flesh that more or less seals off the vagina. Your "not a virgin" boyfriend didn't penetrate it with the results as you experienced. If anything, he should be apologising to you. The more experienced partner has the responsibility.

Please get with your gynecologist for a check-up and exam; get on birth control; make sure he uses condoms; study this forum and the various sticky posts in all categories - then try it again. Practice, practice, practice!!