When I took my 22-year-old girlfriend's virginity, I laid face up and allowed her to squat over me and lower herself onto me at her own pace.
She was a shy girl till we met, which I guess explains why she waited so long. She was a little better than average size, but she had a small vagina. I knew she was scared it was going to hurt because of this, and that's why I let her go at her own pace on top of me. I also tried to relax her by fingering her externally. She wouldn't let me put a finger inside her because she wanted to lose her hymen on my penis.
She took my penis and positioned it at her entrance and started pressing down....and winced. I kept telling her to take her time and go slow. I was hoping she'd go slow enough for her hymen to stretch instead of tear apart, because that really hurts something terrible. She kept pressing till she had me in just past the glans, then she just took a deep breath and forced herself all the way down.
I felt her rip inside, and she yelped and cried out. I didn't dare try to move inside her because she was feeling some intense pain down there. All I could do was hold her and try to comfort her because it scared me as much as it hurt her. We waited a few minutes and she slowly tried moving up and down. I knew she was still hurting, but she kept picking up the pace until I guess the pain became dull.
She felt so good, I guess because she had muscles from running so much. And she made a mess on both of us and the bed (blood and vaginal secretions). It was everywhere, but we didn't care.
I was so glad she was able to orgasm, because that was a difficult and painful experience for her.
But I recommend if your female partner is nervous about the pain of losing her virginity, let her be on top first so she can go at her own pace. You're less likely to hurt her as much this way, especially if she's got a thick hymen. If she's absolutely too tough to "break in," she might need to go to her OB-GYN to see if something's wrong down there. Some girls are born with an imperforate hymen, or a very tough hymen that requires a minor procedure to make intercourse less traumatic. Some of the luckier girls can lose their virginity with little or no pain, usually because they've injured their hymen at a younger age or the hymen itself is pliable or thin.