Incest idea with Pegging & Crossdressing

[hfernandez1983]

So I have been thinking about an idea about a this awkward nerdy teen guy who has this fetish for crossdressing. He's an only child... maybe dad is not in the picture... Lets say his background has just been trying on his mothers underwear and stockings while she isnt home.

Now I had two ideas:

1. He has an aunt who is open minded and fun. Lets say he's going to be visiting her for a week during his summer vacation where he finally opens up to her about his crossdressing since she is the cool and oepn minded aunt. She encourages him and helps him and tells him he can spend the entire week or his entire holiday en femme. Also to make him feel like a complete girl she introduces pegging sex where she teaches him how to be a true slut.

2. This other idea is about his mum catching him one day when she arrives home early. While she is shocked, she is sympathetic at first. And then she slowly starts buying him stuff he can wear and she slowly encourages his crossdressing in private at home. One night lets say they have movie night and she wants to show her son with its really like to be a full on girl and surprises him with a strapon under her pants and then proceeds to take his virginity.

I don't like the whole sissy humiliation domination themes. Any suggestions to improve upon the idea?

 

[LupusDei]

Dickgirl for the rescue of a trapped princess harem slave

What if there's an overarching plan to train our boy as a dick-girl "lesbian" just for him to get a girl who's otherwise unreachable?

The two scenarios you proposed aren't mutually exclusive. Mom and Aunt are lovers of course (sisters for maximum incest, or not related at all, aunt being called so just by association). At least one of them is royal class pervert and matchmaker. Probably the Aunt, rather.

Perhaps Mom wanted a daughter in the first place? She's long caught on son's tendencies and subtly encourages him (like buying and leaving around items that better suits him than her), but she's afraid to be insistent and it's slow and doesn't seem to hold much promise. She's talking about it with her sister/lover, and it has been decided that Aunt will try to bring that side of the Boy out in the light. So when he goes for the vacation, it's already arranged, unknowingly for him.

There's a Girl exist, at least one of our trio greatly cares about, who's trapped in situation the two older women doesn't approve. She might be Boy's half sister in max incest case, his father's daughter with another woman. Or Aunt's relative or daughter of a close friend of either woman or whatever.

Her situation might be as simple as she's seemingly not interested in manly men, but there's some interest to mate her with our Boy for whatever reason, be it prior interest expressed by the Boy, or material (dowry/inheritance) or purely intrigue or even lust by the women themselves. Or she might be under close supervision by overprotective/abusive parent(s), boyfriend (husband?) or just circumstances/environment, literally or metaphorically in risk of being locked in a harem or marriage with unlovable husband, at least in Mom&Aunt's assessment.

The Boy can both initiate this angle, bring her to the attention of both moms, or be taken by surprise not even knowing about her initially, but definitely needs to be interested in her enough to go along the plot willingly. It may even start by accident, but either way, it is likely eventually the Aunt who takes leadership over the plan.

His femme training may even be presented as just making sure he will understand and treat this delicate and delicious Girl right. The role is also important to gain access to her, in either or, physical, social, emotional or psychological level. The Girl herself isn't kept delusional for long or may even know the game from the start, and the Boy mostly assumes male role when they're alone, but perhaps she's indeed falling exactly for the Boy's femme side, actually. Also, her dominant side may unexpectedly emerge.

Additional difficulties may arise from Boy not knowing is Mom onboard with some, all or any of the shenanigans Aunt and he himself went into. Bringing relationship with Mom to sexual level either directly or in threesome with Aunt or Girl (or foursome, for that matter) could be a great relief if not even resolution, even if in grand scale of things, Boy gets Girl, most probably. Or in more twisted case, Boy brings Girl for Mom. Or maybe, he knocks up all three.

For an open ended finale, unforeseen circumstances may trap Boy in female role for foreseeable future (but not necessarily infinitely) by either social, technical or sexual preferences, at the same time not allowing to finalize the expected marriage with Girl and promising new adventures.