The Envelope Series

[JeanPanty]

If you havent read them here are parts 1 and 2 of The Envelope. Long story short he starts getting mail from an unknown woman and feels compelled to follow the instructions given in them. The first envelope contained panties for him to wear but besides continuing the crossdressing theme what are some other good ideas for things she could make him do. I'll probably throw in a good jack off instruction chapter like I wrote in my online chat story, but any ideas are welcome.

https://www.literotica.com/s/the-envelope-pt-01

https://www.literotica.com/s/the-envelope-pt-02

 

[Rob_Royale]

Hmm ... crossdressing isn't my bag, but the whole envelope idea is interesting.

 

[BiteMyLip]

Make him buy a sex toy and use it - send her Polaroid pics or record a video of himself doing so.

Make him go to a sex worker and discretely have a phone call playing so she can hear, or a video so she can see.

Make him do something in public, like masturbate on a sign in a park at night, so she can see his cum when she walks past the next day.

Call him at work in the office and make him listen to her masturbating on the phone while he stays at his desk. Old school desk phone / land line perhaps?

Make him watch porn on a public bus, train or ferry. She sends the link when she knows he is commuting to work and he must tell her plot updates every two minutes for the next 20 minutes.

Fuck me I have such a deviant mind.

 

[JeanPanty]

Ooh very good ideas, will definitely work one or more of these into the story.

 

[TheWritingGroup]

Become a cammer and send her the money. At least at first, she doesn't make him show his face, but she describes in detail how he has to pleasure and edge himself with toys.

-Rocco