Sissy/feminisation story guide

Hi there, I’ve written mostly incest stories in the past but am keen to write a sissy story (not necessarily incest unless that floats your boat) but being a straight male, I’d really appreciate some help with ideas and realism from someone with more experience who can help guide me so that it turns out both fun and realistic within the bounds of that genre of erotica. If anybody would like to help, please drop me a PM or reply here with ideas. Many thanks. Tom

Where does the story take place? At a younger age when our hero is still living at home or in his own apartment?

Is is a voluntary feminization? Something he wants or something someone force him into?
I would say the voluntary or the forced are two different audiences and focus on different elements.

Would love to hear more of your thoughts.

ThoughtfulTom said:

I’d really appreciate some help with ideas and realism from someone with more experience who can help guide me so that it turns out both fun and realistic within the bounds of that genre of erotica.

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I've not read nor written sissification pieces but I'll guess that, as with Incest, too much 'realism' should be avoided. Incest reality is mostly horrible. Sissification... I dunno, is there any reality there? Try searching LIT stories for #sissy tags and note winners in the genre -- use that as your writer's guide. Sorry I can't help more.

Musing: I'm considering writing some 'vore', a genre I've not read. I'd face the same hurdle if I wrote #sissification, and similar to breaking the Incest taboo: How do I make it coherent and plausible? Lou Reed glossed it over in Walk On The Wild Side -- it just happens. I suspect #sissy readers want more details, as of a long persuasive campaign to blur gender identity and display.

Lace's points are right on. Think of various setups and possible consequences. Setup factors: the MC's age, race, and social status; where and how they live; family and friends. Then, what forces drive feminization: internal or external? Do they resist, and if so, how hard and how long?

Try this: Visualize a final scene. Then build the story to get there.

The best homework for writing sissy fiction would be reading a few stories by Vickie Tern.

https://www.literotica.com/stories/memberpage.php?uid=1192141

One husband after another ends up in panties, and most of the machinations are vaguely credible.

I cant find any stories connected to the Vickie profile.

ThoughtfulTom said:

Hi there, I’ve written mostly incest stories in the past but am keen to write a sissy story (not necessarily incest unless that floats your boat) but being a straight male, I’d really appreciate some help with ideas and realism from someone with more experience who can help guide me so that it turns out both fun and realistic within the bounds of that genre of erotica. If anybody would like to help, please drop me a PM or reply here with ideas. Many thanks. Tom

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In my opinion, you need to narrow the focus of this idea down for us. There's any number of scenarios that such a story could go—each one requiring a different template. Surely you have a basic story idea in mind? It could be wife and her new boyfriend helps hubby find his true place...a desperate young feminine male who calls on his best female friend to help him...it could be a forced (blackmailed) requirement by a co-worker, etc.

Each of the basic ideas above would have a different "formula" for the process (story) of turning the protagonist into a sissy. Yourself being more comfortable in a heterosexual situation might prefer the wife and her boyfriend turning hubby? (Although that also gets you into the cuckold thing ) There's also the non-consent aspect to keep in mind in order to comply with Literotica's story rules (i.e. sissy has to eventually like it, etc.)

I would think long and hard about combining the sissy aspect with any incest aspect. Not because it wouldn't be an interesting twist, but more so because it might be hard to figure out which category to post it to. My guess is that the Incest readers might not appreciate the Sissy aspects...and some who read the Sissy/CD stuff might not appreciate the Incest aspects. The category choice depends a lot on how much (if any) male homosexuality is included. If it is a male on sissy-male story, then Trans/CD would be my suggestion on category.

The best way to start out considering what you posted is to explore a twin sister/brother aspect. Same ages, same sizes, always did everything together. Parents bought them matching types of outfits (we've all seen that).

At some point they she decides they should wear outfits that match even more closely. Maybe she wants to do a switch for a costume party and decides she wants to pursue that further.

Triplets is possible too, two sisters and a brother. The sisters team up to force the brother into it.

One sister or two, they could be at college and this is a Sorority initiation prank.


Whether or not you have them do the Funky Monkey is up to you.

Cock cages are used to shrink peni, dressing men up in female clothing and wearing make up. It doesn't matter if they pass. I have had a lot of men hit on me who want me to be my "girl". Are you wanting to do this from a hetero aspect or a homo/bisexual aspect?

Thank you all for your responses, I haven't checked in for a few days due to work commitments and because I thought the idea didn't have any takers, so apologies for not responding sooner. I'm not wedded to the idea of incest with it and, in fact, the idea I've been kicking around doesn't involve incest. I do like the idea of the twins, though, and I might think about that for the future. I appreciate the points, though, about the different audiences for incest and for sissy/TG stories and will probably stick to trying to work with the latter audience exclusiveely for the first venture into the genre.

The idea I've had is of a young, delicate guy just leaving school. He's been horribly bullied by his father for being weak his whole life and his mother has never been strong enough to stand up for him. A friend/neighbour/possibly even a teacher from his school, around the same age as his mother, has seen this for years and takes pity on him. One day she helps cover up his bruises with makeup and that is how his descent into sissification begins. I tend to see it as a mutual thing, not forced but encouraged. There may be a daughter in the household who takes on the more forceful parts whereas the mother is much more encouraging and gentle. I see the boy as bi-sexual, though not yet aware of that element of himself. The break will come with his own mother when she sees what is happening to him but can't stop him. What do people think?

I have sort of an accidental/self-sissification story called "His Better Half." It's about a man who impersonates his cheating wife in order to exact revenge on the wife and her lover. It ends up not going according to his plan. You might want to read it for some pointers of all the things NOT to do if you are looking for realism.

Carnevil9 said:

I have sort of an accidental/self-sissification story called "His Better Half." It's about a man who impersonates his cheating wife in order to exact revenge on the wife and her lover. It ends up not going according to his plan. You might want to read it for some pointers of all the things NOT to do if you are looking for realism.

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Thank you! It certainly generated some heat among the comments! I enjoyed it though, as you say somewhat lacking in realism!

Over the top revenge/sissification story

https://www.literotica.com/s/a-revenge-fuck