>just started going out in girlmode for the first time >starting

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This is the future you chose.

>>8553440
You know you're going to call her.

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>>8553440
You gotta stop buyin groceries i guess...

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>>8553440
Wait wait wait! So you KEPT her number then?

>>8553522
>>8553528
>khv

Don't do this to me anons, I already hate myself enough right now

>>8553523
Lmao.

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>>8553440
...excuse me while I throw up for the next six months.

>>8553440
Could be an opportunity to get trained. Maybe go for it?

>>8553639
>trained
I legitimately don't know what this means

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>>8553440
sissy boy

Hypothetically, if I was going to call this number how long should I wait before doing so

>>8554090
Now.
Report back please.

>>8554098
I don't even know what to say

>>8553440
If a guy did that he'd be creepy.

>>8554119
"Please wreck my boipussy mommy."

>>8554119
Just call and open with mentioning she gave you her number at the store, let the conversation go from there..

or this i guess >>8554186

>>8554119
Open with "Hi mommy."

Drop "sissy boy" too if you're feeling brave.

Let it go from there.

>>8554214
>>8554193
Should I text her instead? What if I don't exactly want her to call me sissy boy?

>>8554226
No, do not text. Don't worry, she'll do the talking.

Then just use the mommy line. Maybe drop an alternative name for yourself if you want her to pick up on it instead of sissy boy.

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>>8553440
You're living the dream, anon!

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>>8553440
And THIS is why I'll never exit boymode. Ever.

You say older woman op. I don't know if I should start shopping in girl mode or be disgusted with you. What does she look like. Describe her and maybe try to find photos of people that kinda look like her.

Also record the phonecall. I'm way to early in my transition to be able to even kinda pass in girlmode, I need to live vicariously through you op.

And don't worry about your voice, everyone will be far to engrossed imagining the woman talking to them to hear you.

>>8554277
>older woman
She's probably 27

>>8554299
I'm literally going shopping for dresses tomorrow if that's the case.
She's probably gonna be 35+, which is the cutoff point of when it's no longer hot. I'm 18 btw.

we need a greentext of the phone conversation anon

>>8553687
gross

>>8554316
I haven't done it yet and I don't think I want to. Do I really want this to be my first sexual experience? Assuming it would become that.

>>8554306
She was at least in her 40s

>>8554385
Could be a good learning experience. She could have a lot to teach you.

>>8554385
Were you attracted to her?

>>8553440
Maybe she was the ultimate stealth trans and she called you out for looking like a hon and wants to give you her wisdom
Or she's just an old woman who went full on fetish fantasy when she saw you.

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>>8553528

>>8554392
I just feel like if I ever do find someone who loves me and wants to be with me I'll regret that my first time wasn't with them and was instead a hook up with someone possibly twice my age. It just goes against everything for me

>>8554412
Yes. No one has ever shown me the slightest sexual attention and seemed so turned on just by my mere presence, I can't even describe how it felt.

>>8554477
>I just feel like if I ever do find someone who loves me and wants to be with me I'll regret that my first time wasn't with them and was instead a hook up with someone possibly twice my age. It just goes against everything for me
It doesn't have to be just a hookup, anon. Tell her that you don't want to cheapen your first time, and that it has to be with someone who means something to you. In the meantime, you two spend time getting to know each other, and one day it will be special with her.

>>8554489
I don't even know if she's single

>>8554496
Sounds pretty single if she gave you her number. You can always ask her too, you know.

>>8554496
Think about it. She probably always wanted a daughter, and you always wanted to be a girl. The two of you can live out something you never thought you'd have.

>>8554505
I don't think sissy boy equates to daughter

>>8554511
i dont think not trying will let u know her intentions

low quality bait, call and send proof or gtfo

>>8553440
>things that never happened.

>>8554477
It might not be sex. Either way what's the harm in calling. Block your number if you want. You might regret not doing this. Also first times are overrated.

>>8554511
well op, the fact of the matter is - she knows what you want and feels like she can help you. It sucks you don't pass, but this sounds like an important moment of your life for your to explore your desires and to help you grow up.

You have someone who can help you grow, even if she is some form of pervert (or maybe she's shopping for her husband).

Anyways op, you need to take this up. This seems like an amazing opportunity to explore your sexuality. Also, pics please! i want to see how well you dont pass.

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>>8554599
This. You should take it. Live the dream.

OP, just call/text her and see where it goes. there's a vast chasm between responding to someone in this context and then it becoming full blown sex, and you'll be able to veto at any time between those two points. I definitely get not wanting your first sexual experience to be something fucked up and wrong, but right now there's only potential for harmless fun. obviously a part of you is curious because you kept her number and made this thread, so indulge in that curiosity.

however, mark my words: if it starts to feel wrong, bail the fuck out immediately. with matters regarding intimacy; your inherent, animal instincts can save your life. good luck!

>>8553440
Honestly I'd go for it, people like that tend to find it hot to spend $$ on you, so easy money or free clothes, plus if she's hot, sex is sex anon, age is just a number desu.

>>8554544
>Also first times are overrated.
Agreed, OP >>8554477 don't you want to be experienced when you actually meet someone who wants to be in a relationship? Plus relationships that revolve around just sex tend to be pretty weak.

Now go find something cute to wear for mommy so she can fuck your little boipussy.

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>>8554239
>she'll do the talking

>>8554444
Quads confirm.
>tfw no older passable trans woman to take you as her apprentice

>>8553440
post her number

>>8556507
Older passable transwomen who transitioned ages ago are out there but we're stealthy and hard to find.

bump for updates

shit fake thread that probably doesn't even real. worthless without pics, worthless without updates. fuck whiny op and his passive hon shoulders.

>>8553440
That was actually me OP. I just wanted to slam my big strapon into your sissy puss