I let out a sigh of relief as we return to the hotel room. We both knew this business trip was little more than an excuse for the two of us to have a weekend away. The others at the office were definitely jealous. The one meeting we needed to have was just taken care of and now we have until Monday morning see the sights of the city. The perfect boys weekend was inevitable.

I was relieved for other reasons. Things with my fiance haven’t been great for the past two weeks or so. Ever since she caught me dressed in lingerie.

It’d been a kink of mine ever since I was eighteen. I’m not gay or trans or anything like that. There’s simply something about the sensation of the soft fabric on my freshly shaven body that really does it for me. My wife viewed things differently. Something about not being able to see me as a man anymore.

It’s not like I didn’t have those insecurities either. I had this habit of building up a collection of lingerie over months, feeling awful about my secret, and then purging everything. The cycle never stopped.

What didn’t help is that I know you and my fiance are close. You introduced the two of us in the first place and, while I doubt she would ever talk to you about us, it feels like something’s different.

The hotel room we’re staying in isn’t anything fancy. Two beds, a bathroom, and a nice view of the city. I loosen my tie and step towards the window. The night is laid out before us.

“So,” I ask, “What’s the plan? Grab a bite, hit the casino, finish up at a strip club?”

~~~

I’m looking for something long-term. No chats.

What I excluded from this prompt is that my character’s fiance told you everything. She asked you to try and make a man of my character during this weekend. You have no such intention. You want to show my character what their life could be like if they embraced their femininity.

The character you play is up to you. You could be my character’s long-time best friend. We could be workplace rivals. Are your feelings for my character platonic or do you harbour a crush? What about his fiance?

The kinks I’d like to include are feminization, outfit control, exhibitionism, humiliation, chastity, dub-con, forced bi, and orgasm control among others. I’m more than willing to negotiate on any of these.

If any of this sounds interesting to you then hit me up and check out my DPP Profile.