Search Results: condom came off

So there's this "friend".. I do want to have sex with him and he knows since I've told him a handfull amount of times. But with condoms or at least be on the pill... Which i am not but was planning to be.
Im from a good neighborhood but he's street grown.. Therefore he's used to easy girls only. he's 19 and im 23.. I dont do one nights and had only 2 partners before.. He slept with over 20 girls.. Just giving you guys our personality's background. Yesturday he invited me over, and when i entered his place the lights were off.. i asked why? He said "my curtains are see tru" :/.. And took me RIGHT AWAY to his bed.. Lol.. To cuddle and ground on me.. Which i love.. BUT it went down later on.. He tried to put it in and i said, for the 15th time, we need protection (i prefer condoms givong his past) and refused.. Again we spoke of that already.
Then he was fingering me and went down on me and kept fighting for the same thing, but i kept saying no (giving his past, i didn't tell him that his past was the reason.. Worried to insult him.. I just said it for pregnancy). He then turned me over and i had to put my hand over my vagina since i couldnt see anymore what he was doing and got supposedly super insulted. He said "i feel like im rapping you if you're putting your hand there" he burried his face in his pillow. i guess he felt rejected and embarassed so i spent the next 10 minutes boosting his ego because i felt bad for making him feel bad. I told him how much he turns me on and i really like him etc etc.. He decided to come back to me again but only to do the same thing. his dick was out going towards my vagina so i had to out my hand again. he then said that all of that was really weird and wack and he wanted to go to sleep. He gave a weird vibe.. He was covering his face again.. I kept explaining to him that its not him, its pregnancy that scares me.. He is a very insecured guy i think, he didn't want to show me his penis (its good size and nice, i saw for 3 seconds)

I've been dating the same guy for over a year and a half. It's an on and off extremely long distance relationship. It came to me a few weeks ago that our relationship worked out fine in the beginning but it took a toll on my health since I was making my education and my boyfriend my priority. According to my friends and family, I was looking more and more like a zombie.

So, I talked to him about it and we agreed to video/voice call each other whenever both parties were available (aka no school, no work, no projects). It was great for a few months until we started less and less. It has gotten to the point that we talk a few times a month.

I have lost time and love for him. I can no longer imagine a future with him. I am positive that we do have to break up but there are a few issues.

His mother wants us to marry the next year (which is crazy because I would be barely 18, and I want to continue and prioritize my education in order to provide a better life for my mother and my future family) (Don't get me wrong. I do want to get married but not this early. It's risky for my health and my career)

His stepdad has cancer and is at the edge of life. He has also given his blessing and wants me to move to Canada with them. He is working a full time job to support his mother in the event that his stepfather passes. He will be attending college in addition to his job.

He has possible gotten a girl pregnant during our last break up (around February). He claims they (including himself) were all drunk and they forced themselves on him. No condoms whatsoever.

He has cheated on me on the past.

Should I break up now or wait for a better time when it's less hard for him?