I haven't had any classmates pregnant whilst at school (other than one who dropped out and I didn't see whilst they were pregnant). I've been out for a few years now and a few have been/are pregnant. It sounds pretty unbelievable but the girl who was pregnant whilst I was at school and dropped out is one of three triplets, the other two being identical but her being different, and one of the two identical ones only recently popped a few weeks back. Unfortunately I didn't see any of the first ones pregnancy or much of the seconds, not that I find either of them particularly attractive but something about seeing pregnancy on someone you actually know kind of makes them hotter in a way, at least for me. Another one of my ex-classmates is currently pregnant, and I've seen her a few times (we aren't friends or anything so we haven't really engaged) but she's looking pretty big! Again, not the hottest girl ever but the fact she's pregnant has definitely given me a soft spot for her.

I don't know if this counts, but I once saw a woman who posted pregnancy vlogs on YouTube. She was pretty cute, but then I looked closer and realized that she was a classmate of mine from elementary school. That made it awkward.

Sadly I have no tales to tell from my school days unfortunately. 

I vaguely remember a 'close call' where one of them claimed to have taken a pregnancy test without her parents knowing (and she was known to hang around with the boys...and was quite attractive) but how true that was is anyone's guess. 

I do know one of the prettiest girls in our class ended up getting pregnant pretty much immediately after we left school. I had a feeling it wouldn't be too long but with word going around that she was pregnant barely a month after we left, if that, is something I didn't expect.

Another from a different class (who I 'kind-of' knew and shared some lessons with) left at 16 and was pregnant within twelve months. This one I was very surprised about as until the final year or so of high school, she was rather quiet. It was only in that final year did she start coming out of her shell. I did find her very attractive actually (long dark hair, often in a ponytail) but unfortunately as I'm also quite a quiet individual, we never did more than have a passing chat now and again. I did actually bump into her again, purely by chance, at the local pub about five years ago when I was with an old school friend of mine. She remembered me to my surprise, was lovely to talk to for the ten minutes or so the three of us talked and considering some 15 years or so had passed since I'd last saw her face-to-face, had barely changed. Do I regret not 'making a move' or admitting to her that I liked her whilst we were at school... I can't lie. The thought did cross my mind that particular evening. Oh well...

Not really classmates, but I work in a doctors office and 4 of the nurses are pregnant (one with triplets!) Today the two biggest were complaining about their size, and then I was asked to take a group photo of them all.

I actually accidentally outed one of my classmates as pregnant purely by chance. It was spring semester and hot as balls outside. I saw that she was wearing an oversized sweater and I said how are you not fucking roasting right now? I'm skinny as shit wearing a t-shirt and even I'm dying. And then it more/less came out from that and she stopped wearing the sweater. Felt like a dick, but seriously She must have been cooking inside that thing.

Not really my classmate but she was infamous for being pregnant during my freshman year of high school, This chick was a senior, 5’5, big ass and giant belly. The best part of her pregnancy was that she was having twins. I never had classes with her but I’d always pushed being late to class just to watch her waddle and struggle and near the mid to late point in her pregnancy her belly outgrew her uniform and the school let it slide. It was amazing seeing this short Latina chick carry her giant belly and ass to class letting everyone see it and touch it.
After her in my senior year two other girls got knocked up, both were at the end of the school year and that was just when they started to show.