tagTransgender & CrossdressersSissy Maid Son Pt. 02

Sissy Maid Son Pt. 02

byRobyn228©

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 wept on his mother's bed feeling violated and abused. The maid uniform still on his lap, crumbled into a ball and pressed gently on his penis. His mother squeezed it earlier and, even after time passed, the pain still persisted.

Peter has been crying on the bed for about 30 minutes now. His mother left him in the bedroom, she told him she wanted him to process his new life as her maid.

Peter's mother, Rachel, was sitting in the kitchen drinking tea and thinking to herself. She smiled while taking sips, thinking of all the things she can do with her maid/son.

Rachel's phone vibrated on the table. She saw it was a text from one of her friends asking if they were still on for dinner.

"Yes. Tell the girls dinner is still up. Peter is just dying to meet you all." Rachel replied.

Rachel wondered if Peter would actually submit to her, his own mother, this quickly. She knew there was still a chance he could rebel before her friends arrive, but she raised him to be obedient to authority. Though the circumstances are extreme in this case, she hopes it won't be too hard to get him complying with her demands.

She put her phone in her pocket and made her way back upstairs to check on Peter. She wanted him to prepare himself for her guests arriving in a few hours. She walked into her room and saw Peter was in the same positioned as he was when she walked out.

"Are you done yet?" she said in a firm voice with her arms crossed.

Peter was still crying with the dress and his arms bunched up, he looked up at her with his face red and tears rolling down his cheeks. His eyes felt sore after his half-an-hour of crying and his arms wet with all the tears they collected. His feels even smaller with his mother's demanding tone and stance, it only reminds him that he's wearing black lingerie that he knows was given to him out of spite. But even still, he feels obliged to answer her.

"I...I... don't want to do this." Peter mustered up the courage to say. Rachel was pleased that this was apparently the best resistance he could manage.

She walked over to him and bent over to their faces were at the same level and only inches apart. She saw Peter flinch when she bent over, this made Rachel certain that Peter would be easy to train and it made her stomach tingle watching him barely make eye contact with her.

"Sweetie," she said softly and with a smile, "remember earlier when I squeezed your cock and told you that I could upload you jerking off in about fifteen sets of my lingerie," she still had a comforting tone in her voice. He could swear that this was arousing her, to see him cry in her lingerie. Peter was confused as to why his mother would do this to him. The blackmail and the physical punishment, he didn't even think this was possible from her.

"Yes. I remember," Peter meekly mumbled through his tears. Rachel noticed his crying started to settle down.

"Well, you must want me to text them to every one of your friends as well."

Peter looked back at her petrified.

"That must be what you want. Because that's what will happen if you ever even think about disobeying me again," she said in a more commanding tone, holding up his phone. She stole it from his bag that he left at the front door.

"So, are you going to be my maid or the little bitch to your friends?" she smirked, and she knew Peter could see it.

"The...maid," Peter said with a sniffle.

Rachel knew this would the part that would break him. She knew he never had a lot of willpower. After all, all she had to do was lie the lingerie on her floor.

"Excellent," Rachel said as she put the phone back in her pocket, "now head to my bathroom and get rid of all that disgusting body hair. My maid will always be well-shaven and presentable."

Peter walked meekly to the bathroom in his mother's bedroom, Rachel walked in front of his and drew a bath and set our shaving supplies for him.

"I'll add those to your debt," Rachel said, reminding Peter how much he owes her.

Peter looked down at the tiles, his crying settled down now, with his new maid uniform still crumpled around his crotch. The bath was almost full when Rachel turned the taps off.

"There you are. The bath is nice and hot and ready for you. You should start shaving now if you want any time left to prepare for my dinner." Rachel stood up and took the maid uniform from Peter and laid it over a chair.

"I said start shaving now," Rachel said in a firm manner after which Peter immediately began trying to unhook his bra. It took him some time as his hands where shaking but he eventually got it off and laid in on the chair. He then slipped his panties off and put them on the same chair, during which Rachel left the room and returned with the box of all Peter' new lingerie.

"Given the cut of the dress, I don't mind if you don't wear a bra with it. However, I do insist on panties, stockings and a garter belt or there will be hell to pay. Understood?"

"Yes," Peter said as he unclips his stockings.

"Yes, what?" Rachel said sternly.

"Yes...mother." Peter internally hoped he said the thing that would please her and escape punishment.

"Very good, my sissy maid." Rachel said to Peter's relief.

Peter stepped into the warm bath and sat to begin shaving. Rachel went back to her room and closed the bathroom door. She stripped to her underwear, a pale blue bra, and panties set with a black garter belt and stockings, and open her closet to find something suitable for her small dinner party. She settles on a simple black cocktail dress with a lace trim along with five-inch black heels.

Meanwhile, Peter was finding it easy shaving his body, though a little time-consuming. He didn't want to cut himself, but he didn't want to keep him mother waiting. He had just finished his legs when his mother barged in for an inspection on her new maid.

"Are you almost done yet," she said sternly, looking at Peter's naked body seeing the progress he made.

"Yes, mother," Peter said meekly as he was startled by his mother's entrance and felt exposed to her.

"This'll have to do, you can finish later. Now get dressed, maid. You still have to prepare for my dinner," Rachel said in a commanding buy noticeable satisfied tone.

Peter stepped out of the tub and began to dry himself, his mother enjoyed watching him but couldn't wait to see him get dressed. Once he finished drying, he removed the plug from the tub and proceeded to pick up the black panties on the chair, but a smack on his ass froze him.

"Hey," Rachel said quickly with her slap, "wear fresh panties for my guests."

Peter didn't want to think about what that implied right now. He was just thankful the slap wasn't very hard. He put the panties back and walked to the box that was near the door. Looking inside he's reminded that the entire selection is lingerie, so no matter what he picks, it's going to be very revealing. His mother felt exhilarated at what her son became to quickly.

"He's a shaven maid, kneeling into a box of lingerie my old lingerie. And he's all mine," She thought to herself. her nether regions shaking at the idea.

Peter eventually choose a pair of green lace panties and proceeded to slip them on. His mother noticed that his penis was barely contained in the panties while Peter was searching for the matching garter belt.

"I'll be downstairs, came down immediately when you're dressed," Rachel demanded.

"Yes, mother."

Rachel walked downstairs and made her way into the kitchen. She couldn't contain herself anymore. The sight of her son acting completely submissive in her old panties was too much. She reached under her and into her panties and began gently rubbing her pussy, she immediately felt ecstasy thinking of what her son is doing upstairs. She began rubbing faster and harder, then faster and faster. Her body was clenching up against the wall with her knees bent and arching forward. She felt it in her chest, moaning wanting to escape the harder she suppressed it. Her left hand pressed against the wall for balances, quickly clenched her breast as she felt her orgasm rush over her and she let out a soft moan out of an ocean washing over her. Her hand slowing its pace over her pussy as her other hand relaxes, feeling the familiar moisture on her hands and it her panties.

She removes her hand from under her dress when she hears footsteps from the stairs. She walks to where she can appreciate the view of her new maid's descent. Peter's new uniform was a short maid dress, ending just at the bottom of the thighs, making it easy to see when he walking on the stairs. She also saw the black stockings clipped to the matching garter belt, it satisfied her that her new maid properly feared her. The dress had a little apron and it appeared that Peter tied it correctly. The uniform's petticoat helps flair the dress out, Rachel immediately fell in love with her new maid's look.

"You look wonderful," She said caringly as she caressed Peter's face with her right hand. Peter looked at the floor, embarrassed in his situation.

Rachel left and came back holding a shoe box.

"Here," she said gesturing the box towards him. "It used to be your brother's. Don't worry, It's already paid for."

Peter grabbed the box. His skin crawled with the prospect of another surprise. The box didn't feel too heavy, the curiously peaking. He opened to discover a pair of black stilettos. About 4 inches tall.

Report Story

byRobyn228© 6 comments/ 26285 views/ 15 favorites

Share the love

Also in this series

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartJermBugg, Paddles and 13 other people favorited this story! 

Recent
Comments
by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous08/25/18

Love this. Please keep writing more!

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous08/16/18

Very Nice!

Very nice story! This is similar to the fantasy I have involving me and my Aunt. She catches me going through her lingerie drawer and forces me to wear her garter belt, stockings, panties, and bra undermore...

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous07/15/18

I also like where this is going

I really like this series, it's got real potential and I'm looking forward to what is in store for this gurl, maybe some cock sucking and or anal, it's horny but you do need to check out the story formore...

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by lexie5507/15/18

Nice little twist

Did she do the same thing to the brother as well?

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous07/14/18

Sounds like fun

We may need some history on the shoes

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All 6 User Comments  or
Click here to leave your own comment on this submission!

Add a
Comment

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

Refresh ImageYou may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel