(It just occurred to me that I've never noticed any 'Story of O' fan-fiction. Have I just missed it?)
The backstory would have to be somewhat different. I'm imagining O' (or O-prime, which is how I'll distinguish this feminized male character from the original female O) as being a boy, perhaps late teens, but still in puberty. O' is not gay - interested in girls, not a virgin, but not experienced. He does, however, have a hero-worship crush on a young man, Rene, for whom he would do almost anything.
The initial scene, in which O is selectively disrobed in the back seat of a car, would have to change. For one thing, O' and Rene are not lovers, so that dynamic is different. For another, while for O this scene is about becoming more exposed and vulnerable, for O' there should also be the beginning of his feminization. Here's an outline of what I'm imagining:
- Rene asks O' to come along with him on a car ride. They get into the back seat of a car, driven by someone that Rene seems to know. Rene tells O' that he, Rene, is in a bad situation and asks O' to help him by doing him a big favor. O', eager to help Rene, agrees. Rene gives O' a chance to back out - it may be difficult, and that O' will have to do whatever is asked of him. O', because Rene is his hero, wants to continue.
- Rene has O' remove all of his clothing, including his underwear, socks, and shoes, all of which Rene hands forward to the driver. Rene gives O' a silk robe, short enough that O' can't sit on it (which Rene tells him not to do, of course). Rene binds O's hands behind his back and blindfolds him. O' then feels Rene placing a pair of high-heeled sandals on his feet and fastening the buckles around his ankles.
- As the car continues it's journey, O' is aroused by the combination of feelings - the coldness of the car seat against his buttocks and thighs, the texture of the robe against his body, the arch of his feet in the sandals - as well as the idea that he is half-naked, blindfolded, and bound. He gets an erection which he can only assume is obvious under the robe, and that embarrasses him further.
- When the car stops, O's door is opened and Rene tells him to get out. O' is unsure on his feet, but strong hands take hold of his arm and help him from the car, up several steps of stairs, and through a doorway. He hears the door close behind him.
So, what do you think? Would this make a good sissy story?
One thing that I had not noticed before about the Story of O was how emotionally flat the beginning was. Description of what O experiences, but nothing of what she is feeling emotionally. I think that the effect is that the reader can project on O the emotions that the reader imagines. O is sort of a blank canvas. What do you think?
Another thing that I found surprising was the variation in the author's voice. A lot of the first part is in the third person: "Her lover one day takes O for a walk..." But some is in the second person ("The seat is made of some sort of imitation leather, which is slippery and cold: it's quite an extraordinary sensation to feel it sticking to your thighs.") or first person ("I know it was at this point that they freed O's hands, which were still tied behind her back, and told her to get undressed..") I found this a bit weird, but disarming. If I were to rewrite this scene, should I try to be true to the same voice?