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Chapter 5
by madmax777
Do you go to bed?
Go to bed - fem day tomorrow (still resisting)
(finally some naughty fun for those waiting. I intend this route to be a slow buildup full of struggles. Feel free to branch off and go wild)
You keep staring at your pantie-clad ass for a couple of minutes before you realize what you're doing. Struggling to look away, you head towards your new bed. Sarah's bed. Her king size bed is very soft, and as you slider under the sheets, you can smell her perfume all over them. Feeling as if she was there to reassure you, you manage to calm down and forget the panties.
You wake up the next day to your mom barging into the room. "Come on sweetie, we have work to do!"
She grabs the bed sheets and pull them away, revealing your nearly naked body. "You should have chosen the lace ones." She comments.
Not giving you much time to think, your mom ushers you out of bed and towards the makeup dresser. "You have an appointment in two hours for hair extensions, so let me show you how to do makeup. Try to remember as much of it as you can, as soon you'll have to do this on your own. We only have 2 months before the wedding, and Tim will want to see you soon."
Still half asleep, you follow along with your mom's agenda, hoping all of this will come to an end soon.
Four hours later, you're finally grabbing your first bite of the day. You were starving.
You're currently in a café with your mom. You're still wearing your sister's panties, though on top of them you're wearing her jeans. As none of her bra or shirt would fit you, you are currently wearing one of your own shirt, though your mom picked a pretty neutral black shirt. The biggest difference is your face, as you now have some mascara, fake eyelashes, lipstick and foundation. In addition to that, your blond hair are now reaching down halfway to your ass.
You've noticed people seem to be acting a lot nicer to you. As you are with your mom, you are forbidden from using your guy voice or correcting anyone that is calling you "Miss" or "Lady", so you barely answer out loud, giving an impression that you're a cute, shy girl.
As your mom and you are pulling out of the café, you notice the car isn't taking the way back home. "Mom?" you ask, suddenly overran by a bad feeling.
"We're going to your Salon appointment. We'll get you rid of all those body hair. You know, in case you get lucky this week." Your mom winks at you. You feel your sweat pouring out. Oh god. You already don't have much body hair, you don't want to lose them. And as if this wasn't bad enough, you suddenly have the image of Tim kissing you on a couch, as his strong arms are holding you against him. One hand behind your back, the other running your leg, feeling your now smooth, post shaved leg.
You shivers at that weird image. "We'll have to teach you how to tuck it seems." you hear your mom say, which makes you realize you're once again hard. You start to panic.
"It's.. it's from the fabric mom. I'm not used to panties!" You try to defend yourself. While your mom say she understands, you're not too sure she believed you.
The waxing is as painful as expected. Throughout the appointment, you often have to bite your lips and struggle to not let out moan of pain. Near the end, Vicky, the employee, asks you to remove everything so she can do your Brazilian wax. After thanking her, your mom leaves the two of you with a giggle, saying she doesn't want to see her daughter naked.
Vicky is looking at you as she's waiting for you to remove your underwear, making you flush. Vicky is a gorgeous woman, with long brown hair, big round eyes and a very sweet smile. She's a bit on the plus side, giving her a nice large ass which you would love to sink your hands into along with some big and heavy breasts. As you try to find a way to stop her, you hear your mom from outside the room "Come on, I know what you're thinking. Just undress and be done with it."
You strip naked. While you try to hide your erection, Vicky gives you a playful look as she motions you'll need to remove your hands. She is, however, not as playful when you reveal your cock. While not massive, it is a decent size. She quickly apologizes "Oh, my bad. I didn't realize. Don't worry, I don't discriminate toward trans people."
"No, it's not like that." You whisper, so your mom can't hear you from outside. "I'm a man, I'm just being blackmailed-" Vicky interrupts you by covering your mouth. Her other hand starts caressing your penis.
"Oh so you're a little sissy then? Cute little boy like you, dressing up in panties and wearing makeup.
Blackmailed you say? Are you sure you don't like it? Feeling the girly underwear snugly hugging your ass, wearing cute skirts and having men look at you with desire. If you're not into that, then why are you hard right now?"
You try to defend yourself, but Vicky interrupts you by telling you to flip on your front. For some reason, her firm, unyielding tone makes you compel. You flip on your front, now exposing your ass to her. You quickly feel one of Vicky's hand go back for your penis, gently massaging it. While you were flipping, she had applied some lotion to it, making her hand feel much better as she jerks you off.
Her other hand is caressing your ass, caressing it and grabbing it. As her jerking off intensifies, you feel her hand caress your butthole, gently massaging it before sliding a finger inside, making gasp out loud.
"There we go, girl" Vicky says. "Imagine there's some big, strong man playing with your asshole. His firm arms pinning you down as he plays with your girly ass, prepping you up for his steel rod. Moan for him. Moan like the girl you want to be."
You keep moaning, not too sure if it's from the jerking off or her fingers on your asshole. Eventually, you orgasm and shoot ropes of cum on the chair. As you lie there, panting, trying to recover, you hear Vicky laughs a bit as she scoots some of your cum and taste it.
"Have you ever kissed a real woman before?" She asks. Looking down in shame, you slightly shake your head. You've never had any woman interested in you before. Vicky grabs your face and kiss you. Your first kiss. And it's with a hot woman too. If only her mouth didn't taste like your cum...
More fun or finish the waxing?
Replacing your sister at her wedding
A crossdressing story
Story of an effeminate man who has to replace his sister at her wedding since she disappeared. Will everything go as planned? Will she come back in time and save you? Will you be to transition? Will be happy to have people branch off and write chapters, or even DM me ideas. Keeping mode to "Moderated" while I get used to this website.
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- butt plug, anal, blowjob, invest, father son moment, humiliation, crossdressing, crossdresser, wedding, gay, sissy, feminization, pegging, cum eating
Updated on Nov 22, 2023
by madmax777
Created on Jun 28, 2023
by madmax777
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