I (M, 22) was bored after getting home from a quick weekend trip, so I decided to browse Grindr.
Started talking to a pretty hot 22 year old dude, with a really nice BBC. We wanted to hook up, but he is only bi-curious and not out to his parents (neither am I actually).
The solution was for me to crossdress and walk in without saying anything to his folks. I stole a shirt and a bra from my sister, bought panties, leggings, and sunglasses at CVS as well as some bra push-up things.
I drove over to his house, parked a block away and changed my clothes in my car. It made me really nervous to change, and then to walk to his door in women’s clothes. I didn’t pass too well, I need a wig. I was relying on the glasses and a hat.
Funniest part was, his parents weren’t even there they left.
I came in, made some small talk, and got to blowing him. It was not my best work or my most exciting blowjob but it was exhilarating, being in panties, leggings, a stuffed bra, and a tight pink t-shirt. As well as the hat and sunglasses but I took the glasses off. They got in the way.
I got to my knees and massaged his package before pulling down his sweat pants. He was already pretty hard. I sucked him with him standing and me on my knees until I told him to sit down in his computer chair. Went at that a bit before getting up on his bed, on my elbows sucking down while he was in the chair.
Eventually I had one leg in between his, sitting of the couch and going down on his dick. I had more trouble than usual, he was long and thick and I gagged a lot. In the end he stood up, facefucking me a bit. He began to cum in my mouth but I didn’t realize, so same came out and got on my shirt.
Fortunately since his parents were not there I as able to change into my normal clothes and leave after. He told me to hit him up next time I can.
Source: reddit.com/r/gonewildstories/comments/cywaks/mm_crossdressed_to_sneak_into_his_house