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Chapter 15
by
kerchek
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15: First day out
Soon after Kate left, Sarah started helping Mark get ready. With no clothes of his own, he was **** to borrow from her.
"How am I supposed to wear that?" Mark weakly asked, seeing the white sleeveless sundress held out by Sarah. With a V neck spaghetti strap top followed by a waist line right beneath where the breasts were supposed to be and a open skirt with floral pattern knitted across, it looked like a dress designed to catch everyone's attention.
"Just try it on.. Or otherwise do you want to go outside in your bath towel?" Sarah teased.
Grabbing the white sundress, Mark carefully put it over his head, fastening the waist. As they were similar in height, the dress hung from his shoulders with the hem hovering a little above his knees. The problem was the difference in chest sizes.
As Sarah had a larger cup size, the dress hung loose in the chest, with his chest and nipples sticking out from the sides.
"Don't worry, your breasts are still growing," Sarah giggled.
"..."
"hmm... Let me see," Sarah carefully examined Mark from side to side before standing right behind him. Grabbing the straps from his shoulders, she raised it back and tied it into a knot behind his neck. "Unfortunately the strap isn't adjustable but this should do."
Standing in front of the mirror, Mark was left speechless. With the strap tied, the hem of the skirt was now more raised in the front, only covering halfway across his thighs now. Tightly holding down the skirt, Mark silently glared at Sarah wanting to talk back.
"What? I think it actually looks much cuter now."
".. just give me some underwear." Mark grumbled.
"What underwear? I threw that out as well. I am not gonna lend you mine either. If you want, we'll buy underwear first then."
"..."
"Why are you still grumbling as if you've never gone commando before? Anyway, sit in front of the mirror, let me do your makeup."
"Why do I need makeup? Let's just go."
"If you are going out wearing a dress, it's better to wear makeup. Else, do you want others to know you are crossdressing? By the way, I threw out all of your shoes as well. You can borrow one of mine for today but we'll buy new ones anyway. "Sarah pushed Mark towards the bedroom mirror, making him sit down in a stool. "Maybe we should do a small makeover for this room as well. Set up a proper vanity table, full makeup set, hmm, what do you think?"
"...Why?"
"Because you are cute. Now, turn around. Let's get you ready." Sarah started combing his hair. "Oh and you might want to fold your skirt before you sit next time, unless you want to sit on your bare ass."
After what felt like an eternity for Mark, Sarah was finally done. His long blonde hair was again tied into pigtails, his face powdered and layer of glitterring pink lipstick applied, he felt he was looking at another hot girl instead of his own reflection.
Borrowing Sarah's 3 inch white stilettos, they finally left the apartment. As they started walking outside, Mark soon realised there was another major concern besides avoiding eyes of anyone he knows. Unlike Sarah who wore black tanktop, jeans and running shoes, Mark's tall heels and A line skirt made walking feel like a nightmare. Mark could barely match Sarah's pace as they started walking towards the subway.
"Can you atleast give me your shoes? How am I supposed to walk in this? "
"hmm.. don't worry, you'll pick up quickly. Otherwise there will be more punishments."
"What punishment?"
"For talking back to me. I thought you understood. As long as you don't want your little secret to go public, you will do as I say. But since you keep forgetting that every now and then, I am getting you a gift."
"..what gift?" Mark nervously asked.
"You will soon find out."
With nervous steps, they finally reached the mall. While there were a few catcalls, it didn't seem like anyone found out. Breathing a sigh of relief, Mark started to walk confidently towards one of the popular Men's clothing stores only to be stopped by Sarah, who forcefully dragged him to the women's restroom.
Only on seeing his reflection in the large mirror, did he realise the problem. His body, now covered in sweat made the white sundress stick to his skin making his already erect nipples poke through the soft frabic. Looking down, he found that his nipples weren't the only thing that was erect. His dick started poking through as well.
During the entire trip to the mall, Mark's full focus was on trying to be invisible and not draw any attention. The last thing he wanted was to be seen like this by someone he knows. But contrary to his wish, the heels didn't give him much of a chance. Walking on a tightrope, he felt he was being stared at by multiple strangers and onlookers, unknowingly making him feel more and more aroused.
"Come with me, you little slut." Sarah dragged him inside an empty stall. "I think it's better if you release your load before we enter the store."
"... are you gonna give me a blowjob? " Mark asked excitedly picturing it. While sleeping with Sarah everyday, Mark couldn't help but imagine Sarah blowing him while giving a titjob with her large breasts amongst many other things.
Closing her open palm tightly, Sarah gestured moving her hand towards his crotch."Do you need my help?"
"NO! I mean no, it's okay, " he quickly shook his head from side to side. Sitting on the toilet lid, Mark raised his skirt and started stroking his dick.
With his penis now standing only 3 inches tall, he couldn't even wrap his entire hand around it. **** to only use his fingers, Mark tried to get off fast imagining the big breasted woman standing before him was playfully sucking it.
"OMG, are you pinching it? this is priceless." Taking out her phone, Sarah started recording.
"stop! " Mark hissed.
"Why? Shouldn't a girlfriend have a few dick pics of her boyfriend?" Sarah teased lifting the hem of the skirt to his mouth. "Bite it. I don't want any cum stains on it."
Accepting it, Mark tightly bit on the skirt, lifting it completly and revealing his heart shapped pubic hair and naval piercing to the camera.
A minute later he soon got off, letting out a muffled moan unknowingly while lifting his hips up. After sitting in a trance for a few moments, Mark soon got up and cleaned himself with some water and tissue. But unlike his dick, his nipples showed no signs of going down. In fact, he felt even more sensitive than before.
Trying to wipe his chest with water soon felt like a bad idea. If his chest was only partially visible earlier because of the sweat, it was more or less completely see through now. Wiping with tissues afterwards didn't seem to help much either. As each woman entered the restroom, they couldn't help but see Mark as a naughty girl playing with her nipples in public.
"You can play with your nipples once we are back home." Sarah chuckled dragging him out, with his chest still showing through the dress. "Let's go now, we have lot of shopping to do."
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Bully in Skirts
A bully bullied into wearing skirts
Mark, a former bully and freshman at Lakewood university, gets trapped and blackmailed into wearing skirts by sister of a former victim. Things start to get worse as more victims come forward for .
Updated on Apr 7, 2025
by kerchek
Created on Aug 24, 2023
by kerchek
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