Why fight it any longer? The need, the desire, the unexplainable itch in the middle of your back which you can never reach. Just give in and taste what it's like on The Femme Side.
Ouch, yeah, then she’s definitely thought about it. Good luck. I’ll loving hearing about how it works out for you.
This is a question I wished I had more information on, so I’ll give you some general answers instead.
You have a good starting point: You two role play and she pegs you.
If you are at all feminine in the slightest bit then she has probably thought about it. A good way in finding out would be to clean up your body. I’m talking about shaping your eyebrows (it doesn’t have to be feminine, but straightening them out and cleaning them up, thinning them just a little). If you aren’t overly hairy then perhaps shaving your chest and/or trimming up the pubic area, etc.
She’ll take notice and if she has thought about it, she might suggest you shaving more, like your legs.
Take an avid interest in stereotypically feminine things like shopping with her, asking her opinion on color coordinating your clothes, watching her do her makeup. Hell, ask to shave her legs in the tub. Maybe she’ll offer to shave yours at the same time. Painting her toes.
Do her laundry and comment on how nice her silky panties feel.
There are dozens of things you can do like this. The thing to remember is never ever act like something is unmanly. Since you take her cock up your ass odds are that you don’t do this anyway, but still I think it bears reminding.
If she asks you to do something and you feel that fight or flight response kick in, just shrug it away and say, “Sure, why not? It might be fun.” No matter what it is. If you act in the least bit sheepish it’s only going to delay her asking you to wear your own lingerie to bed the next time.
Could be any number of reasons. A few that come to mind would be:
For the adventure. A lot of us like pushing our boundaries, seeing what there is to see and… fucking it whether it be a girl, boy or somewhere in between.
Another reason could be because you want to be with someone that is decidedly feminine even if they have a penis. The majority of girls these days just aren’t feminine anymore.
And yet another might be because of the uniqueness of a beautiful femme-boi, someone that possesses everything that a person could look for in a partner, sex-wise. Think about this one. She can be the top or the bottom, the dominant or submissive, the receiver or the giver, and none of it would be artificial. Being pegged by a genetic girl, while fun, isn’t the same as having a warm hard cock inside you, spurting its juices while maintaining a perfect level of femininity as well.
When you have the chance to experience this nirvana, do be sure to leave your inhibitions packed firmly away and experience what it means to give and receive in every way. I’d also suggest some Viagra to make sure that you are able… that is unless you’re eighteen or something.
I would suppose it might depend on what you consider “dressed up” as. If you’re wearing a chastity cage and a pair of panties then you can still be a sissy, just not much of one. It would be more of a humiliating derogatory term than a descriptive term.
However, if you are totally dressed en femme you can still be a Femme-boi, which is more like your traditional “trap” (feminine looking, but acting more in line with a traditional girl.)
Honey, it’s natural for underdeveloped sissy-bois like yourself to feel submissive, because you’ve grown up being laughed at by normal and above normal men. It’s enough to make any boi feel like a sissy. Now that you’ve realized this it’s only right that you put all those years of being submissive to proper use serving those that are dominant to you.
Your little boobies are sensitive? Uh-oh. Honey, has someone been slipping you some “vitamins” or mysterious “supplements”? If so, then I’ve got some good news or bad news, according to your prospective. They were actually feminine hormones, and from the sound of the size of your sissy clit it’s too late to stop.
So go ahead and enjoy the rest of your soon-to-be-very-feminine life. You’ve earned it!
Caption Creation: I usually find most of the pics at ImageFap, but yes all the captions I have posted came from my brain. Disturbing, isn’t it?
I’ve reblogged a few, but those are pretty obvious, since it says “rebog” on the post in question.
Lastly: Thank you! I try to be impressive. ;)