tagTransgender & CrossdressersSissy Maid Son Pt. 01

Sissy Maid Son Pt. 01


Editor's note: this story contains scenes of incest or incest content.


Note: This story is entirely a work of fiction, and should only be viewed as a fantasy. Any similarities to actual events or people are entirely coincidental. All characters are over 18.


Peter walked into his house, feeling excitement clenching in his stomach. He's been patient, but the time has finally come to wear them. He took them from the laundry hamper and stripped of his regular clothes. Ever since he glanced at them from his way to school, he felt the unstoppable urge to wear them.

Since Peter's mother started dating again, she's been buying sexy lingerie from high-end stores for her potential suitors. Peter saw them lying on the floor of his mother's room after one of her dates stayed the night. He saw them still on the floor when he left for high school.

He clipped on the black bra and slipped on matching panties and the garter belt. He picked out black stockings from his mother's drawers and clipped them to the belt. The material hugged his skin and was the softest he'd ever worn from his mother's collection. He admired himself in the mirror, He looked upon himself from different positions. Feeling graceful and feminine. He saw why his mother would wear this for the men who would visit.

His penis became erect and tented itself in the black panties. The tip pushed itself against the soft fabric, which made him want to masturbate even more. He sat on the bed and slid the panties to his ankles. His dick stood hard and ready.

He clasped his cock and was anxious to release.

"Okay, that's enough for now."

Peter's mother walked in. Peter squealed and threw in hand on the bed. He realized the panties were still resting on his ankles.

"I'm fine with you jerking off, sweetie. But I only just got that."

She pointed to the lingerie still on Peter. Peter's dick was soft and shriveled now, while his face telegraphed petrifying shock.

"Now, now. It's okay, sweetie. I'm not mad. I've known you've been wearing my clothes for ages now. But jerking off in them is something I can't have. You should really learn how to clean up your mess, there are stains all over the carpet and half of them are yours."

Peter looked down to his feet, feeling the shame overwhelm him. He noticed his penis was still exposed and rushed to cover it with his hand.

She had a day off work today, the first in a while, not that she told Peter. She's been planning this for a while, and she's enjoying every second.

"Sweetie," his mother said softly as she bent over and slid the panties up to his thighs. Peter rushed to pull them all the way. He felt it was more shameful to expose his penis than to cover it with his mother's lingerie.

"Please... Please don't tell..."

"Anyone? Well, I tell every guy I bring here that my son wears my clothes, plus some friends. But don't fret, I haven't told anyone you know. Although my friends are coming over in about 3 hours, you should start preparing."

Peter looked up, his face more-so confused now. His mother wore a smirk on her face.

"Oh, haven't I told you? For the past few weeks, I've had cameras record you in my room jacking off wearing my lingerie. So, not only are you going to keep everything you've jacked off in, to pay me back you're going to work as my sissy maid. Serving me and any guest that comes into this house."

She went into the bathroom and came out with a box holding everything she saw him masturbate in.

"There are about 15 lingerie sets in here, and I got you new stockings for each of them. So let's say you owe me $530."

She handed him the box knowing that Peter was shocked.


"Five hundred and thirty dollars. I'll pay you as a sissy maid at the end of each week and I'll expect to pay me back in full via your wage."

Peter has had a part-time job working at his brother's restaurant for a year now. He thought he can pay her back using the money he saved from there.

"M...mum," he said looking to the floor, "I have the money I can p-pay you back no..."

"No," she kicked the bed between Peter's legs, narrowly missing his crotch.

"You will pay my back using the money you make being a sissy maid. Oh, and I called Bobby and told him you quit your job. I can't have my sissy maid wasting her time not paying me back."

Peter noticed his mother said "her."

Peter tried to hold back crying. The last thing he wanted to do was cry wearing lingerie.

"Oh, I almost forgot the most important part." She said opening the box Peter was holding.

She took this piece of black material out. Peter looked down and saw all the lingerie he remembers wearing. He looked back to his mother. She was holding a french maid dress. Is was short and frilly and Peter was shocked that his mother wanted him to wear that in front of other people much less herself.

"I expect you to wear this at all times when you're on duty. I don't care what pathetic excuse you give, if you're on the clock you're in this. And feel free to wear any of your new lingerie with this."

Peter was about to cry. His life was seemingly trying to change in any way it can to spite him. He didn't even like wearing feminine clothes that much, all he wanted was to masturbate in them in front of a mirror. Apart from that, he didn't think about them at all. And now, he has to work in a french maid uniform to pay for lingerie and do it in front of god-knows-who.

"Oh, and I almost forgot the most important part," she leaned in she started to sound serious and angry. She grabbed his penis over the panties and started to squeeze it.

"If you don't do this, I will post every video I have of you jerking off in my lingerie to every website I can think of, along with your name and every other fucking personal detail I can think of, and I will not only enjoy every piece of harassment you get, it will be what I think about when I rub my pussy."

She let her grasp go and stood back up.

"Well? Let's get ready." she said with enthusiasm while Peter sobbed into his hands.

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byRobyn228© 4 comments/ 38652 views/ 23 favorites

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by Anonymous

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by Anonymous07/13/18

great start

thanks mom
waiting on 2nd

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by Anonymous07/11/18

she is being really nasty ,she should help him with his fetish, she is being a bitch

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by 300bowler30007/10/18



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by Anonymous07/10/18


Loved it, I can't wait to read whats next !

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