Rose and Jackie pt 2

This piece is a continuation of my last contribution and could fit into the storyline  before Bea's last piece.  If enough readers are interested there is scope for this part of the storyline to continue independently of how Bea or Bleinda wish to proceed.




 

A few days had passed since his encounter with Rose and he was fearful that she may have spoken to Miss Savage or some of the pupils about him helping her carry out her duties while dressed in an apron and cap but there wasn’t a mention by anyone, much to his relief. It wasn’t something he wished to dwell on but he did enjoy being in Rose’s company as she was one of the few females in this place he felt some way comfortable with despite her having  insisted on him wearing the apron and cap while helping her. There was no doubt he was embarrassed at first but apart making adjustments here and there to the garments Rose made no remark apart for expressing her gratitude for his help and her easy going manner soon  made him almost forget his new attire.

This was the first Saturday that he didn’t have to accompany his mother on one of her interminable shopping expeditions. As luck would have it his mother and his current tormentor in chief Miss Savage had left early for some course or other and thankfully would not be back until late. He had the whole day to himself and just had to make sure to avoid his other persecutors Pamela and her gang.

Lying in bed he began thinking about Rose and remembered that for some reason she had left some of her things in the guest bedroom. Driven by this he went to the guest bedroom and found the cap she was wore on her previous visit and holding it to his nose he inhaled her scent and getting aroused he lay on the bed closing his eyes and holding the cap to his face started to pleasure himself with his other hand.

“Enjoying yourself?”

He shot bolt upright to find Rose in the doorway gazing down at him with a mixture of shock and contempt.

“You horrible little boy, I thought you were different” she spat

“I’m sorry Rose I didn’t know you were coming today” he said feebly, hurriedly covering himself with a sheet and discarding the cap.

“Obviously I’m not the only one coming today” she sneered “I’m sure your mother would like to hear about this.”

“Please Rose, not that. Please don’t tell her” he pleaded. “I’ll do anything, just don’t tell her.”

“Well as the school hasn’t employed another maid I could do with some help.” she said.

“Sure, no problem, I’ll just go to my room and get dressed” he replied.

“That won’t be necessary, I have all you need right here” she announced as she patted the sizeable bag on her shoulder, “As you will be doing the work of a maid it’s only right that you be dressed accordingly.”

He had worn the apron and cap on the previous occasion so he felt it was a small price to pay for her silence.

“That’s fine Rose I’ll wear the apron” he said.

“Of course you will, and also that cap that you seem so fond of, but a maid can’t just wear an apron and cap, now can she?”

“What do you mean?” he answered unsure of where this was going.

“Just as well I collected these from the drycleaners, I was going to drop them off in the maid’s quarters later but I guess we will need them here” she said as she walked slowly to the bed and put down the bag. Opening it she took out a similar uniform to the one she was wearing. He felt a queasiness in his stomach.

 “I think this should fit you, it’s the one the previous maid wore it might be a bit tight but we can fix that. ”

“You can’t expect me to wear that” he gasped.

“Not only do I expect you to wear it you will also wear suitable underwear. Stay here and don’t move” she ordered.

She left the room and he stood rooted to the spot, the sheet covering his naked body, still in shock from Rose discovering him in such a comprising position, wondering did he hear her correctly, she wanted him to wear a maid’s uniform and something about underwear. He was still pondering this when she returned with some items in her hands.

“Right let’s get started” she said brusquely, laying out what he now saw to be items of female underwear. She couldn’t be serious he thought there was no way he would wear female underwear nor a maid’s uniform. He began to come to his senses.

“No way, Rose I’m not wearing those” he said trying to sound confident.

“Now listen here you horrible little excuse for a boy. If you don’t get into these and your uniform pronto I will go straight to Miss Strang the principle and tell her you masturbated onto an item of my uniform. I really don’t think she will allow a pervert to remain in such a prestigious school. It’s quite probable that your mother will lose her job. They are very strict here, ask the maid that just lost her job for a minor infraction of the rules”

He was dumbfounded by her outburst and knew that while that’s not exactly what happened Miss Strang would probably take Rose’s word over a newcomer like him. He couldn’t risk his mother’s job, she’d be devastated. Rose looked at him impassively arms folded.

“Well, what’s it to be” she said

“All right Rose” he said “I’ll do what you want.”

“I thought so” she crowed and there will be a few rules. First one is you will address me as Miss Rose as I will be your tutor and you will curtsy when you address me. Is that clear?”

“Yes, Miss Rose” he meekly replied, resigned to his fate.

“Very well now let’s get you into your new underwear.  I wasn’t expecting this so I borrowed some of your mother’s things there’s not much of a size difference. This girdle will keep that thing between your legs out of harm’s way. She has good taste just look at these satin panels front and back.”

He was horrified. Not only had he to endure the shame of being forced into dressing as a girl he was being humiliated even further by having to wear his mother’s underwear. He had no time to dwell on this as Rose  took the sheet from him and handed him the girdle. He tried to hide his now very flaccid penis but to no avail, he quickly stepped into the girdle as he began to draw it up his legs Rose went behind him and told him to widen his legs. As he did so she drew his cock back between his legs and told him to resume pulling up the girdle. When he was finished she stood back and pulled the high waisted girdle further up his torso until she was satisfied. She then rubbed her hand between his legs and smiled.

“Perfect not only will your girdle keep your little clitty firmly in check it will also give you a more feminine look  down there, not that anyone will see it I suppose”

She handed him a pair of black pantyhose and instructed him how to carefully put them on. Then she held out a pink satin bra and told him to put his arms through it and then she moved behind him to fasten it. She turned him around and adjusted the straps and place rolled up panties into the cups.

“Can’t have a girl without boobs” she chuckled as he grew redder. “Now hold up your arms” Doing as he was told she placed a matching pink satin slip over his head and also adjusted the bra part around his now small jutting boobs. She quickly brushed his hair into a ponytail like she had done on the previous occasion and taking the grey uniform dress from the bed slipped it over his head and told him to placed his arms in the sleeves. As he did so she zipped up the back of the dress. As she held out the apron he knew what was required of him and meekly held out his arms as she wrapped it around him tying it in place. Pointing to a pair of black two inch heels she motioned for him to put them on. Much to his surprise they fitted him.

“Not bad, just a little something else I think” she said standing back to admire her handiwork. He was horror struck as she rubbed liquid foundation to his face and then began applying a pale pink lipstick to his lips.

“Much better, but there’s something missing I wonder what is it? Oh yes your cap” she said as she held out the article that had got him into this mess in the first place.

“Now put it on….. GIRL” she sneered.

Silently he took the cap from her and placed it on his head and fixed it into place with the hair pins attached to it like she had shown him previously.

“Excellent. Now come have a look at yourself” she said as she motioned him to the full length mirror.

Any small trace of masculinity that he may have previously shown was all but obliterated for all intents and purposes he now looked like a young servant girl.

“I think your mother would approve, I believe the vast majority of single mothers prefer to have a daughter rather than a son. I’m sure she would be happy to know you are wearing her lingerie. Now time to put you to work my girl. Oh by the way I don’t think Jackie is an appropriate  name for a maid, I can’t think of a suitable one at the moment so I will just call you  Girl. Ok with you Girl?” she asked rhetorically

Knowing he had no choice regarding this further humiliation he nodded.

“Yes Rose”

“What did you say” she snapped.

“Sorry Miss Rose I forgot” he apologised making a crude attempt at a curtsy.

“Well, I’ll let it pass this time. And we’ll have to work on your curtsy.”

“Yes Miss Rose” he said almost gratefully.

“Now the last time I was here I showed you the duties of a maid and you were quite a good pupil so let me see what you have remembered. Start with your own room, I will give you fifteen minutes and then check on your progress. I expect everything to be spick and span when I make my inspection. Or else there will be consequences” she ordered as she pointed to his room.

He turned and left and for the first time felt the sensations of the feminine clothes he was now forced to wear. He wobbled slightly at first in the heels but after a few steps got the hang of it. He now felt the girdle constrain his stomach and the odd feeling of his cock tucked between his legs  unable to move because of the girdle holding it firmly in place. The bra straps gently biting into his shoulders and across his back, the satin slip rubbing against the material of the uniform dress making a faint rustling sound. He heard the whisper of the pantyhose as his thighs rubbed together as he walked in the unfamiliar shoes.

He entered his room and again saw his reflection in the mirror. He had to look very hard to see any semblance of the boy who left this room an hour ago. A somewhat downcast young  uniformed maid stared back from the mirror. His thoughts were interrupted by a now familiar voice at the door addressing him by his new name.

“GIRL… stop admiring yourself and get on with your work.

“Yes Miss Rose” he said respectfully and gave a much improved curtsy.

Rose left her new charge to get on with her work and thought to herself this could be the start of a wonderful arrangement.

Carrie