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How do I "break myself in"

Tagged as: Sex, Virginity<< Previous question   Next question >>
Question - (15 June 2010) 2 Answers - (Newest, 15 June 2010)
A female United Kingdom age 30-35, anonymous writes:

I'm just about 19 years old and I'm very confused as to whether I'm a virgin or not.

I have have two boyfriends, and I've been seeing quite a few guys on different occasions and we've fooled around....so it's not like I've had no sexual experience.

I'm ashamed to say that I gave in to peer pressure in year 10, and since that day everyone I know has thought I wasn't a virgin. But I think I still am.

I went to university and felt I had to keep the lie up because no-one I knew was going as a virgin, so I did. And I met this guy, who I became best friends with - and he's very popular with the ladies....

My problem is - In France on holiday, I got drunk and carried away with a guy I met called Stephen. Mainly because I wanted the burden of my virginity to be taken away from a stranger (Although you'll think bad of me for admitting it, I had to be honest). He was very considerate and soft with me because he knew I was a virgin and kept asking me if it was what I wanted just incase I'd changed my mind, so it was completely my choice.

Basically, he penetrated me a little because it was almost agonizing pain. I was biting him to keep quiet as we were in a hotel with people we knew (obviously they didn't share his room but they were around so I was conscious of that). So the deeper he went, the more it hurt. And we were trying for hours but it hurt so much and I don't think he went fully in.

Anyway I was expecting blood to show when I woke up the next morning, but it just so happens that I came on my period the next day (it lasted a week) and I know it was my period because of the amount of blood.

So naturally, I thought I'd lost my virginity as he was inside me, but many months later I'd been in contact with the boy I like from university... and we were in bed fooling around. His penis is quite wide and long. He tried to go inside me when we were a little horny... and it wouldn't go in. I was so embarrassed because he doesn't know I'm a virgin, and I don't know if I still am.

But I don't understand how this happened, why wouldn't he go inside? Was he not pushing hard enough? I was very wet at the time! How do I break myself in? :(

View related questions: best friend, drunk, horny, lost my virginity, on holiday, period, university

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A reader, anonymous, writes (15 June 2010):

This is verified as being by the original poster of the question

Ohhh my :) Thank you for that! I'll do that exactly, along with what the other writer said, like abit of lube haha. I'm just scared it'll happen again I really don't want it to, because I want our first time to be good sex.

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A reader, anonymous, writes (15 June 2010):

This is verified as being by the original poster of the question

Thank you for clearing the first thing up! It was so painful but I just wanted to get it out of the way...However, I don't regret it at all.

Yeah I felt very tight. The only thing is- I've lied not to him but to the friends that we both know while playing drinking games, because he thinks I'm a "sexy girl" and I teased him abit...only in a joking way though. But yeah, he thinks I'm not a virgin. Well I guess I'm not but I'm totally inexperienced :(

Ahh thank you, I'll suggest foreplay first if it doesn't happen when I see him. The wine sounds like a very good idea to relax too hehe! Ahh yeah, I should look into lube products too.

Thank you so much!!

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