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Being gentle/third time is the charm.

Age when it happend: 18
Where it happened: My dorm room
Langauge: English
Sex: Male
Rating: 5
Category: Straight

Well since I have read enough of these stories, I think I should finally share my first time or my first three times depending on how you look at it.
I went to college and met a young woman in my class the first weekend at school and started dating her. We started kissing and cuddling and feeling each other. Over the next few weeks we become more and more intimate. Both of us are virgins.
One Saturday morning, she invites me over to her dorm room. We laid down on her bed and cuddle a little. She tells me that her roommate which I can not stand will be gone until that evening so we have the room to ourselves. After a half an hour, we begin to talk about sex. I tell her that I would like to have sex with her if she wants to have sex with me. She tells me that she wants to have sex with me if I want to have sex with her. Since we cleared that up, it is time to have sex.
I remove the last few pieces of clothing she is wearing and she pulls down my shorts. I move to mount her missionary style and place my penis on her hymen. I push myself into her tender hole and she tenses up and pushes me away with her legs. She is in serious pain so I stop before I even mount her. For the next hour we lay in each others arms talking about how bad we are at sex and how we are total losers.
A couple days later, we decided to try again. Again, I am trying to mount her missionary style and again I stop because I am putting her in serious pain. Another failed attempt to make love ended in disappointment.
A week later, we tried again. This time, I am going to mount her in the spooning position. Fortunately, this did not hurt as much and I was able to mount her. Still it was a little painful. I will never forget her saying, “Ow, ow, ow, ow… Oh, Baaaaaaby!” At that moment, I was inside of her vagina finally. It was heaven. Pure heaven.
I lasted about thirty seconds before I ejaculated inside her vagina. For the record, she had a very big happy ending as well. I am sure all the ladies will be happy to hear that. I pulled my penis out of her and she turned around and planted a giant, deep, wet kiss on me. For the next hour we talked about how we finally got it right, how wonderful it was and how much fun it was. We spent that night in each other’s arms.
The next morning I had to wash the sheets as there was her blood on them from the previous night. She bled the next three times we made love as well. Somehow, I did not mind washing those sheets afterward, though.
Eventually, we broke up. Even though she was a few months older than me, she needed to grow up. She was not an adult at age eighteen, I was. At that age, I did not know that I was going to feel so incredibly good or make a memory that I will carry around with me for the rest of my life.
I was gentle with her and did not rush her and caused her as little pain as I could have. I made her very, very, very happy in the end. My advice to anyone reading this will to be take your time and be gentle to that special woman. I would even say that at first it would be better to let the woman take control so she can make herself comfortable because she has the tough part to handle.

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