Here is a true account of a weekend that my wonderful wife and I shared a couple years back. She is not outwardly kinky nor does she participate in all of my sessions, but in this case she was a more than willing participant.
Once my wife packed a suitcase with some girly clothes, shoes, a wig, purse, and makeup, she told me we were going on an overnight trip and did not tell me she had packed anything other than my vanilla clothes. She told me as well to plan to have some fun, which clued me in to the fact that she was planning something kink-oriented. When we arrived at our hotel, I noticed the suitcase and began to wonder what she was up to. Once inside our room, she had me strip, giving her all my vanilla clothes, shower and shave my face and legs, then return to her. Once outside the bathroom I see the suitcase on the floor, with a padlock hanging from the zipper, effectively sealing it closed with my vanilla clothes inside. All the girly things she packed are lying on the bed, to which she instructs me to get dressed therein. Once dressed she helps me with my makeup and wig, helps me paint my fingernails (my toenails stay a shade of pink anyway
), thereby making me as close to passable as I can be. My outfit consists of a knee-length polyester fuchsia skirt and white long sleeve top with a faux breast bra, black 4" heels, suntan opaque pantyhose, and a pink makeup palette.
My wife tells me I look about as much a woman as I can get, and that I have two paths to return to masculinity. One, she has 4 padlock keys in one of her hands, and a chastity cage in the other. I may choose this path with the cost that she will lock the chastity device on me, the key to which is already in the suitcase. I may after the device is locked choose one key from her hand, the others will get placed into the suitcase through the small hole the zippers make where they are locked together, effectively sealing them inside until the padlock is opened. So there are 2 possible outcomes for this path, if I choose the correct key I will be able to open the suitcase, retrieve my chastity device key, and be able to return to my vanilla clothes, not to mention having fun with my wife since I would be free of my chastity. However if I choose the wrong key, I am stuck in chastity and girly clothing until we return home to the spare keys the next day, this outcome also carries the cost of bringing my wife pleasure without using the equipment she had previously locked into chastity. The hotel we are staying has only one exit that won't trigger alarms, right through the lobby, which has been filled with people every time we have walked through there. This means I would have to walk through that area the next morning in full view of anyone who happens to look.
The second option is that she and I go out to eat at a restaurant right then and there, the choice of restaurant being at her whim. The only detail she gives me is that I will not be required to speak in the restaurant if I choose this option since my voice range is far too low in pitch to possibly pass as feminine. If I choose this option, my wife will open the padlock sealing the suitcase on our return to the hotel and I may then change clothes and return to masculinity. Ordinarily this option would be the easiest to complete, except I have no idea where we would go, what if she wants to go to a bar restaurant? What if it's a walk-up? Still I would give this option a great deal of thought, but it is also a holiday weekend so every conceivable restaurant is packed.
Admittedly, I love being dressed as a woman, and I love being in situations where I have no control, but now being faced with those 2 things exactly, I freeze, almost unable to move. I, being almost paralyzed with nervous energy, choose the first option. I choose a key, she places the other 3 in the case, and applies and locks my chastity cage, I then put my key in the suitcase lock and attempt to turn it. I am immediately both incredibly excited and terrified when it doesn't turn.
I resign myself to my fate, unable to sleep, and too excited for the day ahead to even rest. The next morning does come however, and my wife surprises me with a long black hooded cardigan sweater, a perfect concealment garment. We spend the day driving around, stopping at a few stores where I remain in the car, and even stopping at a fast food restaurant with an outdoor seating area away from the majority of the other customers, so I actually ate in public, in reasonably close proximity to the vanilla public, whilst fully dressed, which was incredibly exhilarating!!!
I like to think this is one of those scenarios that ended up being a wonderful experience! I learned a lot about how to present myself in a feminine manner even though I think my pass-ability is lacking. My wife and I have not been able to plan a scenario this in-depth in quite some time but I continually look forward to the next one
This is a true account of a session I actually participated in, though I always welcome any input as to the writing style and to some degree content. I make no claim to be a professional writer. I am also new to the forum so if this is posted in the wrong topic space, please let me know. I hope you enjoyed my account and I hope it inspires fellow kinksters!