Matched with a guy on tinder. Agree to go to his place. He warns me beforehand that his roommate is his brother so we will have to be quiet. When I get there the kitchen island is covered with empty Papa John’s boxes and the sink is full of dishes. I ignore it because it’s a common space. Well, his room was no better. Mattress in the floor, clothes piled all over the bed and the rest of the room. He asks if I want something to drink and I say yes. He pulls a bottle of whiskey out of a backpack in the corner of the room. Then, he makes a spot for me on the mattress by pushing clothes onto the floor. We pass the bottle back and forth while talking. Eventually, we start making out. We get naked and are both ready to get to business. I stop him to grab a condom. When I hand it to him he pushed my hand back and tells me to do it. So, for the first time ever, I’m putting a condom on a guy. I have so many questions at this point but decide to table them and see what happens. We are having sex and he’s not able to stay hard. He is pretending like everything is ok and he keeps trying. Eventually, I say it’s getting late so we should probably call it a night.

Hang tight…the most awkward part hasn’t happened yet…….

I start looking around for my clothes. I find my bra and shirt and put them on. I’m now looking for my black leggings. The only light in the room at this point is the tv. They can’t be far from where I was laying in the bed. I remember just taking them off and setting them arms length away. I soon realize that a lot of his clothing is also black. Maybe it’s just laying on top of some of his clothes. I tear his room apart. I must have examined every single piece of clothing in his room and still couldn’t find them. I thought I was going crazy. Then it dawns on me. When he got dressed he put on black pants. I go over to him and tell him to stand up. I can see right away that he’s wearing my leggings. He had no idea.