Background: I’m a 19 male, I have a female best friend, let’s call her A, I’ve known her for 4 years. She’s one of the first people I came out to as gay,and was fully accepting of it. We still keep in touch although school ended. I’ve told her almost everything about me, sharing my cross dressing fantasties,as well as my bedwetting and that I wear a diaper to bed. She was accepting and told me she’d love to dress me up and that I probably look cute in diapers. I’ve never been interested in her and neither she in me.
Actual Dream: Me and a few friends basically went to see her at her house for her bday. Slowly everyone left and it was just us,as I was about to leave she asked if I still wanted to cross dress. I said Yeah sure but now? She said her parents weren’t home and her sisters were off in another state. I said ok. So she leads me to her room and starts putting together an outfit or me. When she takes out a pair of panties I ask her whether it’s for me and she says Yeah if you’re doing this do the whole thing. So I agree and then she asks me to strip. I’m shy at first but she says she’s practically my big sister it’s no big deal and so I strip naked in front of her. She smiles at my hard on and says we’ll get that out of the way. I thought she was gonna ask me to masturbate or do it herself but instead she pushes down my dick and duct tapes it away. Then she helps me wear the panties and comments that I’m nice and smooth with no bulge there. Then I wear her short skirt and bra,with a crop top. All of it is pink, including the lingerie. She says I look really cute and does my makeup so I look as girly as possible. Then we basically play video games together a while,and gossip about guys.
I try and get a glass of water,but I break the glass. She gets mad and asks what she’s gonna tell her mom who told her to be especially careful nothing breaks. I apologize but she says that’s not enough,and that as my elder sister she’s gonna punish me. She sits in a chair,makes me lie over her lap and pulls up my skirt,pulls down my panties and starts spanking my ass hard, till it’s red. I end up crying and saying sorry, reaching back to cover my ass,but she says if I reach back I get spanked more so I stop. When my ass is red she starts giving me a wedgie, pulling the panties elastic all they way upto my head and hooking it there. The panties tear in the process but she says it’s ok and she was gonna give em to me anyway. The panties tear completely,so she takes them off,pulls down my skirt,and gives me a corner timeout until she’s done cleaning up the glass. Then she pulls up my skirt,gives me the panties and apologizes and says she was mad and maybe she went overboard,but I tell her she’s my big sister so she can do whatever she wants it’s fine. I stand in front of a mirror and check how red my ass is pulling up the skirt,and I see handprints left there, and I laugh and say it looks like tomatoes,and she also laughs. Then I sit,but it hurts to sit so I jump up and I wake up
Source: reddit.com/r/gonewildstories/comments/nk658v/had_a_dream_my_m_straight_best_friend_f_that_i