You have stated previously Kenny is a lesboy, but how many girlfriends did our little ladies' butch have?
He's been involved with both straight girls and queer girls alike throughout his dating history.
The first time he dated a girl it was when he met Kelly on a school field trip.
At this time Kenny was only 8 years old and believed she was just a little girl pretending to be a boy. There was some cognitive dissonance he had until he learned about transgender people. The moment she picked up a magazine or saw women dancing on TV he knew she liked women.
So when she got a crush on Kelly he didn't know how to explain that she wasn't a cis boy but just a tomboy pretending to be one of the guys. So he just let Kelly believe he was a cis boy. They didn't officially call themselves a couple per say but they did hold hands alot. They where only 8 so it wasn't very official or serious. They just held hands once. Cartman says this doesn't count as a first girlfriend. Kenny doesn't agree and insists it counts.
For most of grade school that's how it went, he was just pretty sweet to most girls he met and if they have her a kiss on the cheek or a hug that was just a bonus.
His first serious relationship was in 6th grade when he dated Tammy Warner. By this time she was comfortable being a dyke. He didn't exactly come out as a lesbian but he wasn't exactly hiding it either. He kinda felt like a straight lesbian in the way he was simultaneously a lesbian and a straight boy.
This time Kenny was honest with her and explained that he's not really a boy but a lesbian. This didn't discourage Tammy though, she didn't really care if he's a lesbian or not, she just likes Kenny. He dated her for a few months but Tammy never wanted to share any kisses because she wanted to save it for marriage. He started to feel like he was pretending to be a straight boy, and she partially was but it felt like he couldn't express his queerness in the relationship. So he eventually broke up with her. He still had complicated feelings for her.
In the meantime he kissed a few other girls including Bebe and Wendy. Kenny claims he's kissed every girl in middle school. Cartman is skeptical and thinks he's exaggerating.
In 7th grade Henrietta Biggle found Kenny a cemetery hole. Henri pulled him out and believed that Kenny was an undead zombie or something. They decided Kenny was adorable and took him home to wash up and fed. Henrietta impulsively claimed this dyke they found was their girlfriend and Kenny wasn't complaining at all. When Henrietta asked if he's a zombie Kenny just told them it was sort of true. Of course Henri thought was hardcore. Pete and Michael had a alot of questions when Henrietta was feeding a random boy a sandwich and snuggling her.
Henrietta was nothing like Tammy. Henrietta was very affectionate and liked to kiss her. Henrietta was a out and proud lesbian. Dating Henrietta felt inherently queer in a way that Kenny had spent years yearning for. Being friends with Pete Thelman made Kenny realize he's transgender. Henrietta didn't seem like it to most people, but Henrietta loves romance and cuddling. They're actually a huge hopeless romantic lesbian.
In 8th grade Henrietta got a crush on Bebe and Kenny wanted Henrietta to go for it. They didn't exactly break up per-say they just kinda had an open relationship they didn't realize they had. Kenny just told Cartman he wanted to keep his options open and didn't want hold Henrietta back. Cartman tells Kenny that lesbians are confusing.
Kenny did flirt with Heidi when she temporarily broke up with Cartman. Kenny asked about and Cartman was so offended he was trying to take his ex-girlfriend so suddenly. Nothing actually happened but it did annoy Cartman.
In 9th grade Kenny kissed Nichole once at a party game of spin the bottle, her girlfriend Leia Black didn't mind it and watched lol.
In 11th grade Kenny sometimes joined Heidi and Cartman to smoke weed and eat junk food. Heidi was a lesbian too so she and Kenny sometimes made out. She liked to shotgun Kenny with weed or share a blunt. Cartman was a little annoyed with them making out in front of him but didn't care enough to complain.
At the same party he kissed Craig Tucker with Tweaks permission because Tweek knew it was playful. It confused the fuck out of everyone there though.
In the 10th grade Wendy broke up with Stan on good terms and finally accepted she was genderfluid. Kenny liked to flirt with him when he felt masc and kissed occasionally just to get a rise out of Cartman.
After highschool I'm exactly sure what my headcannons are but I know Kenny ends up getting Married to Henrietta and have a daughter. Henrietta still dated Wendy and Wendy was the godmother to their daughter.
-long after Henrietta and Kenny got married and Kenny was becoming a successful scientist they decided they wanted to have a kid together. Henrietta is polyamorous and Wendy is his girlfriend.
-Henrietta was happy to carry and they both decided it would be safer than Kenny carrying [he is trans and able to get pregnant]
-with Assisted Reproductive Technology and a few years of attemps, Henrietta became pregnant.
-when Henrietta told his Mom he got pregnant, she thought it was an accident and was asking for help with getting an abortion. Henri quickly corrected her and explained this was a planned pregnancy.
-Kenny was very anxious during the pregnancy and fretted over something going wrong.
-Henrietta gets a ton of weird looks for being pregnant and transmasculine. He went off T during his pregnancy. Henri doesn't give a shit about what other people think and everytime someone complains they grow more facial hair.
They are both in a very stable home and income but it can be dangerous for Henri to be pregnant and visibily trans in public. Kenny doesn't like them to go out alone, so Stan offers to join Henrietta with errands and stuff like that. He also just uses it as an opportunity to catch up with his friend.
-Pete and Michael were very happy about Henrietta having a baby and helped out as much they could. They're honorary uncles of the child.
-Wendy is the godparent of the child
-Henrietta got a C section, there wasn't any complications when he gave birth. Kenny was stressing out in the waiting room but his friends kept him calm as much as they could.
