Theo would probably have bought them for you, but if you suggested it he would take a long look at them thinking he will get made fun of by the other Slytherins but then after some convincing he would give in and wear them.
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Tom Riddle
You would literally have to spend a whole week convincing him to wear them he was kinda of against it but when he saw Mattheo and his girlfriend wearing them he decided he would fuck you then you guys could wear them.
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Regulus Black
He loved the idea and he picked them out he, wanted to see you happy. He wouldn't really want to wear them in front of the slytherins just incase they do say something but he wouldn't let go of you while wearing them.
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Mattheo Riddle
He was probably drunk and suggested the idea and you loved it, when you came into his dorm with them his face lit up and you two smoked and cuddled together in them all night.
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Draco Malfoy
For christmas you always went to his parents house and his mum suprised you both with them. You loved the idea and it took draco some talking to get him into them but he wouldn't take his off.
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Blaise Zabini
Blaise saw you had liked a lot of pictures with couples wearing matching pjs and decided to suprise you with them, he wasn't scared at all to show the slytherin boys and they all called you two cute.
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Lorenzo Berkshire
He definitely had the idea and kept talking to you about it until you finally ordered some and he opened the parcel so fast the skin on his fingers could have come off. Never see him without them.
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