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Chapter 27
by grimbous
Do you want to go out dressed like a girl?
Heading out Shopping
"Umm..." You think about this hard. Heading outside while looking like this? What if you ran into someone you knew? What if people noticed? How would they not? Remembering how you looked in the mirror you had to admit that they would actually have to look pretty close to notice, you really looked quite feminine done up like this...but still. Ordering stuff online would be so much safer, though so much less exciting.
El and your mother seems so intent on it. You finally say. "Sure. I'll do it." This cheers the whole household.
While you shower you are straining your memory about any mentions of Aaron's shop. You remember a mention once about a year ago, but the subject was quickly changed. Probably to keep you in the dark. You do yourself up as best you can only to be taken aside once more by your chuckling mother.
"Oh my goodness. No, no, no. Let Mommy do you up again." She goes through the steps from earlier that day. This time she puts you in the final outfit she ordered for you. A plain dark pleated knee length skirt, long dark socks, and a short sleeved white blouse with a neckerchief. It had a heavy resemblance to your classic school girl uniform. The panties were a plain white, you had to change these because you leaked a little in the yellow ones during the excitement with your mother. These new ones didn't fit quite right however, it was noticeably constricting.
Your mother looks concerned. "Oh no. These ones aren't as good." She tries to reposition your package, which only makes the matter worse. "Oh no. It's scrunching your little bean isn't it? Your poor little pussy, I'm so sorry sweetie." She thinks a second. "Maybe Fiona has something that might fit you, or you could go commando."
You knew for a fact Fiona would have nothing that would fit you. You really enjoyed the full support panties gave you. You say. "It's okay Mom. These will do."
"Ohhh..." Your mother bemoans, she really felt bad about this. "We'll find you something at the shop. Sorry about that."
She puts on the finishing touches and you look better than ever. Elsie is waiting outside your mother's room for you. She was in a long green dress and one of her obscure anime t shirts. The simple shirt hugs her curves marvelously. She takes your hand. "You look great!" She beams at you.
"You too El."
The three of you head downstairs, Elsie keeps your hand in hers as you walk together. Again, the memories flood back. You forgot how much the pair of you would hold hands when you were younger. Something about exposing your soul and sharing this secret and newly discovered interest of yours had rekindled something between you and your little sister. Fiona was waiting at the door.
"I call front seat." Fiona winked at you two, even your big sister was feeling the good vibes of the day. Another memory triggers. She always used to say that, even though you and El liked being in the back together and never wanted the front seat. Thinking about it now you couldn't remember the last time all four of you took a car ride together.
The rest of them get ready as you stare at your ratty old sneakers. That wasn't going to work. Your mother says off-handedly. "Wear Fiona's flip flops. They should fit."
Fiona sighs, this flippant disregard of her property souring what had been an improving mood. "Pfft. Sure, why not? Who cares about what Fiona says! Christ!" She snaps. "Maybe Jesse would like my room too?"
Your mother glares at her.
You decide to try to smooth things over. In your softest tone you ask. "Can I borrow your sandals Fiona? Just till I get some shoes of my own?"
She sighs loudly. "Fine. In fact...they're yours. Happy Girl-day faggot."
"FIONA!" Your mother barks, you could feel Elsie tense up beside you.
You stop your mother. "It's okay Mom." You slip them on. "Thank you Fiona." Tensions ease but don't disappear.
Stepping out the front door is quite an experience. The sun was shining, the weather perfect. Old man Frasier was mowing his lawn and some youngsters were playing a few yards down the block. You didn't know what you were expecting. The world to come to a stop, crowds of friends gathered to stare at you, teasing cruel neighbors, something. Instead...nothing. Everything was just going along like any average day. Although, the breeze felt great on your smooth shaved legs beneath your skirt.
El stood with you hand in hand as you had your moment. "Everything okay Jesse?"
You nod as you realize you had just been standing there looking around. Fiona and your mother were already in the SUV. You get into the vehicle and each buckle up. Your mother in the drivers seat, Fiona beside her, Elsie with you in the back. Man this felt like old times! Despite Fiona's little outburst at the doorway all of you were feeling the beauty of this family moment.
All four of you just take a minute to look at each other. It suddenly felt like 5 years ago again. No one says a word but you all acknowledge it silently with each other. The Bailey family bond was strong despite everything. Finally your mom starts the van and heads toward downtown.
El and you were still holding hands. She didn't seem to want to let go, and to be honest neither did you. You figured it was because she really wanted to let you know how supportive she was of you in this delicate moment.
Eventually it is Fiona, always Fiona, to break the mood. "Um guys? We should really talk about this."
"About what dear?" Your mother asks obliviously.
"About what!?" Fiona exclaims. "Your son is sitting in the back seat dressed like a girl and we are all calling him a her. This isn't strange to you?"
"Oh Fiona, why'd you have to say that?" Your mother gripes. "It's just for today, and then maybe from time to time."
Fiona looks at you. "I'm sorry but I really don't think so Mom. I think he thinks he's a girl or something. Probably the shock of knowing what a needle dick he really is."
Both Elsie and your mother were getting angry. You didn't know what to say. Everything was still so confusing for you. Maybe she was right? Maybe this was just some crazy psychological reaction or mental defense mechanism. You were starting to have doubts. You begin looking around nervously, worried people outside the van were looking at you, judging you, laughing at you. El squeezes your hand and whispers. "It's okay Jesse, don't listen to her."
Your mother steams. "What did we talk about earlier Fiona? What did I tell you? Things were going so nicely."
"I know! I know!" Fiona says defensively. "But we can't just pretend this is normal. This is fucked up, even for us."
Elsie suddenly pipes up. "You're...You're just jealous! Jealous that she looks better than you. You..you...fucking...um...ugly...cow! She doesn't have...a...big fucking ugly...thing like yours. Hers is nice, she is nice." You can feel El trembling. "She's a better sister than you'll ever be!"
The rest of you are stunned by Elsie's outburst. She had never spoken to Fiona like this before! Fiona's eyes widen in anger as she turns and fixes her little sister with a furious gaze. Poor Elsie withers under Fiona's powerful **** of personality. Your little sister melts into her seat, shoulders slumped and eyes down. She tries to pull her hand back from you so she could huddle up but you hold it firm, letting her know she wasn't alone.
Fiona snarls. "Why you little..."
"Everyone calm down!" Your mother cries out. "Okay...everyone just please...calm down. This is an adjustment, I understand." She looks at Fiona. "I'll let this slip this time. But no more of this Fiona. Understand?"
Fiona faces forward and lets out a frustrated breath. "Yes Mother. I mean...I don't honestly care that much. He wasn't much of a man anyways. I just thought we should talk about it and not just pretend like it was normal. That's all."
Fiona and your mother continue to talk, you were too concerned for Elsie to really listen. As they continue on in the front seat you guide Elsie's chin upward to look you in the eyes. You whisper. "Thank you. Thank you for defending me."
She gives you a sad little smile and a subtle nod. Something deep inside you stirs as you catch your breath. You couldn't wait for that sleepover tonight! She grips your hand lightly. You sit back up straight and tall, a little more confident than before.
Fiona eventually turns to you. "Listen Jesse...I'm sorry okay. But...it's just..." She sighs. "...anyways...sorry I ruined your big day." You actually think she means it!
By the time you get downtown things had returned to normal among the Bailey clan...as normal as they could be anyways.
What's next?
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Runt of the Litter
You've got the smallest cock in your family...and you're the only man!
You're family has a few BIG secrets. A Futa-SPH- Story.
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Updated on Jun 19, 2025
by grimbous
Created on Apr 20, 2023
by grimbous
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