Confessions of a Private School Girl Entering the Real World

A diary of a private school girl's first year in the real world with real people. It's a wreck, let me just say that now, a complete and utter mess.

Contains sex, love, drugs and all things in between. Warning some people may get triggered.


4. 5th June 2018

So I have decided to release the daily updates I have been making rather than waiting until all the monthly updates have been done, so you can go back and read them as I go so things make more sense. I know the names are silly but it makes it easier to be entirely open about everything and not hold things back.



Today I had sex with him. My second time and it still hurt so much. I bled again but not as much as the first time. He still couldn't fit properly and we had to try about 4 different positions for it to work out. We ended up having to put my legs over his shoulders because he just kept slipping out otherwise. It actually felt so good and even though we didn't have that much time, he actually finished this time and it drove me insane how he choked me the whole time.  It was so awkward because we had to stop half way through as I had to answer the phone and make sure my dad wasn't coming home early. I kinda wish I could talk to my mom about it since I am concerned about the bleeding and how much it hurts but we don't have that kind of relationship. I am really glad that B is safe, he always insists on using a condom, as do I and I am on the pill but at the same time, that concerns me about how many other girls he could be sleeping with and that hurts. I like kissing him, I like when he kisses me all over and the way our tongues are in sync. Its so intense but I can't tell if that's because we hate each other or love each other. I know I love him but he's just using me. It's so toxic, he's the cigarette and I'm the smoker.


He didn't message me later but he did kiss me gently goodbye as he left. I then messaged his best friend back on tinder. His best friend Justin is so much nicer than him and we've actually had some really great conversations unlike I have had with B. He already knows more, however I feel like its going to be a shit storm when he finds out who I really am. It's weird he doesn't remember me but I remember him, I think that shows a lot, it shows how much B lied to me and pretended to be interested in me. I am snap chatting his friend now, he sent me hearts and X's and called me cute, hes nicer than B ever was. The only reason I am doing this is to fuck with B, I want him to realize what he gave up to be a hoe. I need to give B up but I am attached and I think it's partly because of this sexual awakening with him. I am only sexually attracted to him and that scares me since for so long I thought I was asexual and well clearly I'm not but I don't have the desire to have sex or be sexually involved with anyone other than B, and that frightens me and it frightens me that I am going to lose him soon.


Hunter asked me to go to the movies with him tonight but that was just too weird for me and I feel so bad. Shit is so complicated and I don't know what to do. I am so confused. I feel like that would be fucked if I did that after having sex with my on-again-off-again boy. Shit is fucked up. I was with Hunter yesterday, we went to a music festival and it was cute but the whole time I was just wishing that it was B who was holding my hand and cuddling me. I had tears in my eyes. Ashley pissed me off too, she came 5 hours later and didn't bother to text that she was in the crowd but left us waiting another hour and a half in the cold and the rain for her. She didn't even apologize. She then had the audacity to comment on my situation with Hunter. I am so sick of her. I do think I have some feelings for him but I am so unsure of what those are because of B. I just want him but I know that it will never be. 

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