Sweet Carolines

Things returned to normal the next day; until evening, that is.

Alice came in with a package in her hand. It looked like she picked up some dry cleaning, but I soon saw that it was not so. "What's the matter," I asked her, "did you get your uniform dirty? It looked OK last night."

"This isn't my uniform. It's yours."

I looked at her blankly.

"Tuesday and Thursday is supposed to be 'girls night out;' no boys allowed. So I thought you ought to look your part."

"And that part is?" I asked.

"Little sister. Each girl at St. Caroline's was a little sister when she first got there, and in her turn became a big sister as she advanced in grade. You are to be our 'little sister' and we will teach you what it's like to be a girl at St. Caroline's."

I shook my head in disbelief.

"Follow me upstairs so I can get this thing altered properly."

Before I knew it, I was standing on a small step stool in my underwear with blazer on my body and skirt around my waist. I looked at Alice and almost laughed. She looked somewhat comical with her mouth bristling with pins. Finally she removed them and said, "There, that should do it. Take care taking off your schoolgirl uniform, dear. I wouldn't want you to get stuck."

She spent the rest of the evening in the sewing room hemming the garments. I was called upstairs for a final fitting. The uniform seemed a little funny. The blazer seemed to have extra short arms, or what for a man's jacket would be short arms. I kept pulling at them. Alice admonished me, "That's the way it's supposed to look. All the girls wear them that way."

However, he blazer wasn't my immediate concern. I felt a lot of draft coming up from under the skirt. It was well up my thigh, and I was sure if I had an erection, it wouldn't cover it.

"I'll help you get dressed tomorrow," Alice promised, "But after that, you are on your own. You will be responsible for cleaning and ironing all the parts of your new uniform."

When we got down to the kitchen, Alice handed me a piece of paper.

"What's this?" I asked.

"Part of it is a list of things you are to pick up on the way home from the store. Another part is a recipe for what to do with those things you pick up. Don't worry; I picked something simple. Even you can't screw it up. The last part is a list of chores for you to do. Tomorrow is Thursday and my friends are coming over. They will come into a clean house, and you will serve them refreshments."

"And where does the uniform fit in?" I asked.

"What do you think you will be wearing as you do your housework and wait on us?" Alice asked back. "Or would you rather go naked?"

Even though I knew that I would be required to take off my clothes (feminine or otherwise) for the spanking and wanking, I opted to keep my clothes on at least part of the time.

The next morning was embarrassing as well as I saw TWO schoolgirl uniforms hanging on the closet door; one noticeably larger than the other. I couldn't believe I agreed to this, or did I? I don't recall agreeing, but then again, it just sort of happened so naturally without my even thinking about disagreeing.

I managed to make it to the office safely, but I couldn't keep my mind on work. It kept drifting back to the events of two nights ago. My secretary noticed and asked if everything was OK. My boss noticed and suggested that maybe I go home and think about some vacation. Even the security guard asked as I left work, "Man, what planet are you on?"

I absolutely detest stopping off on my way home to do errands. Alice does all that stuff for me. So I was really not in a good mood having to drive a quarter mile past my house to the supermarket and then spend another 15 or 20 minutes there hunting for the stuff Alice had on the list. If I were picking up stuff for myself, it would be a hit-and-run raid: beer, chips, express checkout. However now I was required to wander up and down the aisles looking for things like parsley sprigs and nutmeg.

I got home with my treasures and found Alice waiting there. "Let me show you where to put those things," she said. We soon had everything staged for its preparation when she announced, "OK, now lets go down to the bedroom and get you dressed."

As I entered the bedroom, I found everything already laid out on the bed. I was dismayed to see frilly cotton panties and ankle socks. "I couldn't find a pair of loafers to fit properly, but these navy blue Mary Jane sneakers should go well enough with the outfit," she said with shoes in hand. "Also I couldn't find a bra that would fit you properly. You have a big chest, but let's face it; you have no boobs. They don't make a 42 triple-A." She laughed.

Soon I was naked and before I could do anything else, Alice dragged me into the bathroom and worked me over with her electric razor. "Shave your face too. Nobody at St. Catherine's ever had a 5 o'clock shadow. Except maybe for old Mrs. Bonnafucci," she laughed.

I came out and Alice assisted me getting dressed. I had a problem with the blouse since the buttons were on the wrong side. I felt like I had all the grace of a 4-year-old getting dressed all by himself for the first time. The skirt was not much better. The zipper and the button for the skirt were in the back. I was sure that Alice was giggling as much at my antics trying to get into my outfit as how I looked in it.

"Guy clothing is sensible. Zippers are in the front where you can reach them. Why are girl clothes all backwards?" I asked.

"That's because in olden days, women had maids that dressed them. The zippers and the buttons were for the benefit of the chambermaid who dressed the lady."

I finally slipped on the sneakers and was ready to leave. That's when Alice dropped the last surprise on me. "Here's your hairstyle," she said, handing me a blonde wig done up in pigtails. I put it on. "One last touch," she said as she fastened a bow of ribbon on each pigtail.

"Stand back. Let's see how you look?" She sat on the bed as I modeled my new outfit. Alice made a twirling motion with her finger to indicate that I should turn around so she could see me from all angles. "There, now you look like a proper St. Caroline's girl," she said with pride at her project, "Now hands at your sides, back straight, head up!"

She led me back out to the kitchen and got me started on making the refreshments for her friends. "Now, you have a couple of minutes while that's cooking, and you can't start that until about 5 minutes before the company arrives. I want you to pick up the papers in the living room, run a vacuum, and put out the coasters. I'll be in getting myself dressed."

I was quite busy trying to clean up AND cook a meal (albeit a simple small one) all at the same time. I prided myself on being able to multitask in the office, but this was beginning to overwhelm me. I was also glad that I was wearing sneakers, even if they were "girl sneakers" to make it easer to run back and forth.

I was just putting the finishing touches on the refreshments when the doorbell rang. Alice cried out, "That will be the girls. Would you get it please?"

"I can't answer the door like this," I thought. However, I did think better of it and decided to take the risk rather than incur Alice's wrath. I peeked through the peephole and saw that it was Keri. I opened the door, and falling into character did a clumsy courtesy and said, "Good evening, Miss Keri."

Keri just stood on the step and burst out laughing. "Wow, Alice didn't tell us she was going to dress you up!"

Just then another car pulled into the driveway and Brenda and Sam got out. They saw me at the door and started laughing.

By the time we got inside, Alice was coming down the hall. Soon there were 5 "girls" standing in my hallway all wearing St. Caroline's Girl School uniforms.

"Be a dear Caroline and get the girls and me some of those refreshments." I was wondering, "Who the hell is Caroline," when it struck me that Alice was referring to ME.

Turning to her friends she asked, "Do you girls want some tea? Caroline will make it and serve it." To this all the girls agreed even though I had never seen any of them drink tea before.

I spent the better part of a half hour walking back between living room and kitchen fetching little things for the girls. Even more so was the unfetching of used napkins, discarded teas bags, and "dirty" plates.

"She's so cute," Keri remarked, "Where did you ever find her?"

"Oh, she's been under my nose for a long time," Alice purred. Then with an evil grin, she added, "Now she's under my thumb."

"Good help is so hard to find," Brenda remarked, and they all broke up at that old joke.

"Caroline, leave the dishes for later. You can clean up while we are practicing." Alice ordered, "Come in here, we have other things we want you to do."

Soon I had the room arranged pretty much the same as it was several evenings before.

"I think it would work out better if we spanked him first," suggested Alice. "Now who wants to go first?" Once again, three hands shot up, but none faster than Sam's.

"OK, Sam, you take the seat of honor." Alice said. Turning to me she said, "Get over her lap. Lift up your skirt and pull down your panties."

Soon my body was draped over Sam's lap as she paddled me with expert skill. The other women cheered her on, "That's it Sam. Faster, faster. Punish that bad boy. Give it to him good." My rear end was burning by the time Sam finished.

I stood up and rubbed my backside.

"None of that," Sam ordered authoritatively. "Hands on your head, and face in the corner." I stood there with my back to the four girls. With my hands raised over my head the skirt hiked up high enough to see the bottoms of my ass cheeks. I had lost the panties somewhere during the spanking. I do recall doing a couple of leg kicks during the performance.

After an indeterminable time while the girls chatted about things that went on since they last met, I was ordered to turn around. I was greeted by a couple of whistles. The front of the skirt just hung down either side of my penis.

"Get that off," Alice said indicating the skirt. "I don't want you to get it dirty."

Soon I was standing there in wig, blouse, socks and sneakers.

Keri noted, "You know, that doesn't quite look like a girl, and it doesn't quite look like a boy either, but it's cute whatever it is."

"You know what to do," Brenda put in.

Once again I was putting on my show. I was getting better and not only could I hold out longer, I also learned to gyrate seductively and make guttural, grunting animal noises as I approached orgasm culminating in a series of groans synchronized to the squirting of my penis.

I collapsed on my heels. One by one the girls came over and gave me a kiss on my forehead or cheek. Alice was the last. "You were fantastic, tiger," she whispered.

They departed to the den to practice. I didn't need to be told to perform my duties of cleanup. By the time the girls were finished the place was spotless.

The reunion went off great and the Sweet Carolines were a smash hit including the new comedy number featuring the 5th Caroline!

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Although the show was over and they no longer needed to practice, the girls still met at our house at least once a week. They didn't need to wear their uniforms any more, but I was still required to wear mine. Alice still wears hers from time to time, just to remind her to keep fit, and to put her in a mood to mentor her "little sister."

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