Sissy Story Chapter 02

God I was cute. There was no use denying it.

The device came the next day and Mom gave it to me without comment. I took it up to my new room and tried it on. It was very uncomfortable. I decided I couldn’t wear it even to the beauty shop. I put it up on my closet shelf where I could see it from the bed and it, honestly, triggered an erection every time I noticed it for a while.

I took the instructions that came with it to the bed and read them. There were all sorts of information about hygiene and adjusting it, which looked a little more promising. But, all in all, it looked pretty complicated and I wasn’t sure it was all worth the effort. I wasn’t sure of anything having to do with it. In fact, I was struggling with the idea anyone would find it erotic. Eventually I got used to it being in the room where it became less relevant because I gradually learned to control myself. I still masturbated every night though mostly I quit fantasizing about the device. I got more into myself and how I looked and fashion. I did wear it a couple of times, to get used to it, like you do high heels. I couldn’t get it adjusted right so, unlike high heels, it was always uncomfortable on me, so I lost interest. It just wasn’t for me.

Another problem was my voice. It could be embarrassing from time to time, and, as usual, Mom had a solution. She had me find videos on Youtube which discussed this very issue with solutions, which mainly just involved recording your own voice and playing it back over and over until you got the tone and timbre you liked then practicing, practicing, practicing. It really didn’t take all that long until I had the voice I wanted and sounded authentic all the time. It turned out to be one of those problems that practice solved, no talent whatever was involved. I quit using my boisterous and loud male voice at any time, for anything. Mom approved of the change, and I did too.

What she didn’t approve of so much was the attention one of the pool boys started paying me. I noticed him noticing me, and so I thought it was fun sending him to the kitchen to get me sodas and my purse and run little errands. When Mom found out she was furious. She gave me a talking to and then called up the maintenance company and gave them real hell. That fellow never showed up at the house again. I realized I had probably caused the guy to lose his job and I felt bad about it. Not bad enough, however to quit dressing very cute when there were workers on the property, though.

I even went so far to check if I could wear the chastity device in my bikini to preclude any erection, but I looked at myself in the mirror and it was too obvious. I was beginning to believe that it was absolutely useless. I put it back up though, but forgot about it, mostly. I thought about the gaffe, but ended up just tucking my penis up between my legs and securing it with tape. It was a little uncomfortable at first, but nothing like the chastity device and it looked better. Learning to control myself was the best thing I did, both for looks and attitude. Watching how people reacted to me and then trying to figure out what they were thinking was effective, too. Honestly it gave me something to think about besides sex.

Mom and I fell into a new routine, me taking my lessons pretty much alone with Mom helping with any questions I had. We shopped at the mall more and more, we both loved it and I needed plenty of things all the time. School really started encouraging me to choose some of my own subjects, and I emphasized art and design. That had been Mom’s major in college and she’d turned out pretty well. Mom and I took trips to museums, and other trips to see things I learned about in school. We visited Chicago where I went to Apparel and Accessories at the Mart. And every Wednesday, I went to my appointment at Babe’s. It hardly ever took much over an hour or so after the first visit. I maintained the same hairstyle and color, and we did maintenance and my nails.

Mom didn’t stay with me in the beauty shop for my whole appointment after the first couple of weeks. We’d park the car, she’d drop me at the salon and go shopping in the wonderful shops in the area and I’d call her when I was finished. I wore my new clothes all the time. I didn’t even own any boy clothes anymore anyway. The major recurring problem I had was my breasts, or lack thereof. Mom showed me little tricks to enhance my breasts, but, all in all, I was totally dissatisfied with them. It was the one thing about my life that was not ideal it seemed.

At home, shopping, going out to eat, Mom and I loved spending hours together almost every day, and she constantly taught me how to walk, how to sit, how to cross my legs, how to twist in the chair to emphasize various parts of my body, especially my legs and ass. I spent hours in front of a mirror smiling, learning how to give certain messages with different smiles, how to elicit admiring looks from people. Mom talked to me all during these lessons about being pretty, how much of it is how things are done and attitude. She took more videos of me walking and sitting and doing little things and together we’d critique my actions afterward. It was an education, an education every girl needed but not many got. I still have the dozens of videos Mom and I made that I enjoy watching every now and again.

I still loved to watch Mom put on her makeup and gradually appreciated what a master of it she was. She told me putting on makeup was simply drawing a pretty face on my face so I learned to watch details.

She still sprayed me with perfume at the end, only a little more and told me how pretty I was. When we dressed for dinner a couple of times a week, I generally wore a dress and high heels and did my own makeup. She’d take pictures of me and the talk about the mistakes I’d made, and what I’d done right as we sat on the sofa after returning home. I loved getting dressed up, and I loved the appreciative looks I got from the boys. It was a new life, reflecting I think, the fact that I was growing up and changing. Somehow, with everything going on, I managed to skip teenage angst. In fact, my teen years were a wonderful. I learned a lot and had fun doing it. I couldn’t have loved my life more.

I’d fallen into the habit of going to an ice cream shop by myself every
Wednesday after my appointment. I generally got a small drink or cone while I waited for Mom to come pick me up and we’d look at her treasures while we had some treat or another together. I had even gotten my own credit card, with my picture, as I was now, on it. I was a young adult, responsible and confident, like a hundred other girls who came to the upscale shops in the area.

One Wednesday, dressed in pink sandals, a pink hair band, and white shirt and very short shorts, with pink lipstick and pink nail polish and faux pearl swirls on my toes, waiting for Mom, my reverie was interrupted. A boy came up to the table and said, "Hi". He surprised me, coming from the side, and I blurted out "Hi" without thinking. I’d practiced enough so that it was in my girl’s voice, thank God. I turned to look at him and he just stood there. I instantly noted that he was nervous so I asked haughtily, "Can I help you?" He looked at me and asked if he could sit down. I hesitated and then moved my purse leaving him the place open across from me at the four-chair table. "I guess so", trying to sound unenthusiastic. I wasn’t sure of any of this, but Mom was on the way. He was quiet when he sat down and I examined him from behind my sunglasses. The first, and most obvious thing I noticed about him was he was the way he ogled my crossed legs, through the glass tabletop. He looked like a cartoon wolf ogling cartoon babes and it was so obvious it was funny. To finish off the picture he seemed to be trying to be nonchalant but he was failing badly. I couldn’t help but smile. I re-crossed my legs, putting the other one on top, which Mom had taught me, to keep his attention on them. Sometimes Mom dawdled, but she was coming, so the worst this little incident could be was a minor annoyance. It was definitely new, but I was confident I could handle everything the poor boy was so pathetic. Besides, we were in public, outside at an ice cream shop with dozens of people around in the afternoon. He was a lot more nervous than I was, so I put my elbow on the table, rested my head on my fist and looked at him and gave him my most dazzling smile, from behind my mirrored sunglasses, of course. It was easy. I didn’t say anything. I loved watching him squirm. I understood I was totally in control. I re-crossed my legs. I said nothing.

His opening was, "I don’t know you. You don’t live around here and you don’t go to Park Haven High". He said this totally focused on my legs and feet. I loved it.

"No I live in a different area. I go to private school. Mom and I like to come here to shop, though". I didn’t help him any more than that. It was fun watching him struggle, watching him look at my legs. I shifted every couple of seconds to give him the best possible show. It was like a drug, watching him and realizing the control I had. To be fair, he was game though. To give him credit he kept looking and kept trying to think of something to say.

I looked him up and down. He wasn’t ugly. To be honest though, he wasn’t beautiful, like me. I just kept smiling, saying nothing.

"Do you guys play football?"

I must have looked startled, "Football"? I leaned back and took a sip of my soda through a straw.

"Yeah, do you go to St. Olaf’s or Hollycroft, you know, the private schools."

"No, no football, at all. I don’t like football much". I leaned forward on my hand again, "I like fashion", and gave him the smile again. I noticed, through the table, he had an erection. God, it was so obvious. Did I look that obvious when I had an erection?

He was still really struggling when Mom came up with a cheerful, "Oh, Sissy, who’s your friend?"

I smiled at Mom and moved my purse to give her a place between us. "I don’t know. He asked if he could sit down here but he didn’t tell me his name, and he didn’t ask mine." I smiled. He turned red.

"I’m Tommy."

"Glad to meet you Tommy, I’m Sissy, and this is my Mom," I extended my hand across the table and he took it for a second.

"Glad to meet you, too. I can’t call you Mom, ma’am."

Mom considered him and gave him a smile and a "Mrs. Quinn ought to do it. What have you two been talking about?"

Normal Mom questions, I could handle this. I volunteered, "Football and fashion."

Mom questioned me, "Football?" And looked at Tommy.

"Yeah, I play football at Park Haven and I thought her school might have played us sometime."

I chimed in, "I told him my school doesn’t play football. I didn’t tell him I’m home-schooled. I was teasing him. Neither Mom nor I know much about football, I don’t think." I kept smiling and he kept watching my legs and feet.

"Oh." He colored again. I liked embarrassing him. I shifted and smiled.

"So, Tommy, what’s your last name," Mom asked, like Moms do.


"Do you live around here?"

"On Haven Hill."

"Well, it was nice to meet you, Tommy, but Sissy and I have to go home now."

"Wait, Mrs. Quinn, when can I see Sissy again?"

Mom considered him, "Most Wednesdays she comes here after her beauty shop appointment and waits for me. Bye."

I chimed in "Bye" with a little wave, and Mom and I walked to the car arm in arm.

"He is cute," Mom said, eyeing me.

"He was awfully nervous and he couldn’t quit staring." I laughed.

"You’re awfully good looking," she said, emphasizing ‘awfully’ in the same tone I did.

I giggled. "Well, staring is rude."

The week dragged a little bit, it seemed. I went to driving school a couple of days with the idea of getting my license soon. We went to look at an art exhibit, which I didn’t like. To be truthful my mind was on what I was going to wear on Wednesday. Mom looked up Tolan on Haven Hill and found out his father was some sort of financier and in the news from time to time. Tommy himself was mentioned a couple of times in football games.

I chose my outfit carefully the next Wednesday. Red was the color. I had some new wedges with a three-inch cork heel and red lacings and red bows right behind my toes. I picked a cute red skirt that was very short. My panties were red lace, and I chose a white blouse and a white lace bra that sort of disguised my lack of breasts. That was becoming very annoying, by the way. I knew I’d have to talk to Mom about it, but I put it off again. I had very small breasts, not adequate for even an A cup bra. I put a red ribbon in my hair to show off the platinum blonde color and curls and carried a large red leather purse and had red hearts dangling from a few pearls as earrings. I had some red sunglasses that covered half my face that I could hide behind. I didn’t wear a lot of makeup, but I was very careful putting on what I wore. I looked young and wholesome, and very sexy. It seemed to take me a long time to get ready. So long, in fact, Mom commented on it with raised eyebrows. But I didn’t respond to her, I just looked dignified and we were on our way. The trip was normal and I had a normal appointment, except I got hearts in little tiny rhinestones on my toes. I looked sensational when I went into the beauty shop and looked better for the short walk up the street to the ice cream parlor.

Tommy was there, sitting at a table. He waved me over. I saw him, hesitated, thinking there was no need to appear too eager, and then smiled and went over to his table. He had some stuff arranged on the table so the empty area was in front of a chair next to him. I put my purse in that spot and moved some of his stuff and sat down across from him with a "Hi. It’s nice to see you again."

"Thanks. You too. I was afraid you weren’t coming."

I looked at my phone. It was a little after two. "The beauty shop generally takes an hour or so. These nails don’t just happen". I pointed through the table to the area where my legs were crossed to call his attention to them and my pretty toes. I wiggled them, and then lifted my foot up to the table, and innocently said, "See?"

He sputtered and choked on his coke, something ran out his nose. I took my leg down as I noticed the waiter starting to panic. I smiled and crossed my leg, letting my skirt ride up just a little before pulling it down and handing him a napkin with a smile. "They don’t grow like that, you know." He got my most dazzling smile that I’d practiced over and over.

He wiped his chin and considered my legs through the table. He couldn’t keep his eyes off them. I shifted. We flirted like this for a while, waiting for Mom, who managed to sneak up on us again while we were talking about Tommy’s ambition to be a lawyer.

"Hi, you two. Good to see you again, Tommy."

"Hello, Mrs. Quinn, we were talking about school," he volunteered.

Him volunteering that wasn’t as truly brilliant as it first seemed, since Mom immediately began questioning him about school, about his family, everything. I smiled and looked adorable. I glanced at my reflection in the tabletop while they talked. Every now and again, I looked at myself on the mirror app on my phone. He couldn’t really see my eyes so I looked at him to make sure he was looking at me while he talked with Mom. I was the real center of attention. It was exhilarating. Mom was finally satisfied with her third degree and we excused ourselves to go home.

Out of earshot, Mom asked, "Do you like him?"

I looked at her, "He’s OK, a little self-centered, but OK."

She smiled and said, "You’d know if anyone would."

I didn’t reply to that, it would have been undignified but I did decide Mom was taking a second shot. I did take pride in the way I looked, but wouldn’t anyone who looked so good? We did talk about Tommy a little on the way home, but that wasn’t what was really on my mind, I brought up my lack of breasts. Mom looked at me and said, "Is it that important to you?"

I looked at her in surprise, "YES, it is. It’s annoying and clothes don’t fit me right>"

Mom said, "I guess if you really want, I can look into it, but if we do it, it’s not going to be like your device. You’ll have to have an operation."

I got serious, mostly because Mom was so serious. "I want it."

"No changing your mind, afterward."

"Yes, I want tits," I was adamant.

The next day true to her word, she looked into it. I thought about it, was looking forward to and so was excited, but I’d never had an operation before and I wondered what it would be like.

Mom and I talked about it that afternoon. "We can go to Europe for a couple of months, get your implants, take a tour of museums and get you credit for your school. I was looking at it, and it’s all you have left to complete High School. When we come back, you’ll have breasts and enough credits so you will be a simple application away from getting a diploma from High School."

"Wow, Mom, that sounds great!" I hadn’t considered High School that important, not nearly as important as how I looked, but this would make an epic trip, a trip which could have a huge effect on my life.

"OK, I’ll make the arrangements." She cautioned, "It’s a big step."

"I’m ready, I’ve been ready for a couple of years."

Mom looked thoughtful. "It seems like you do everything on the spur of the moment, Sissy, without truly considering the ramifications. This isn’t a lark that can be easily fixed or ignored you’ll be taking a big step. This is an adult decision."

"I’m really ready for it, Mom." I really was.

"OK. Let’s agree that we aren’t going to get stripper boobs. Some augmentation to solid A cups will be the most natural. It won’t be a huge change from your present appearance. If life changes and you want to change, it will still be possible later. With all that in mind, I’ll let you know our plans as they are made. In the meantime, keep thinking about this while there’s time to change your mind, like you thought about the chastity device."

I thought about it all night. I even thought about Tommy and everything in my life. I did notice the device on the closet shelf and thought about wearing it around the house for a few days, but decided it could wait until I came back from Europe. I was resolved to finish this. Amazingly, I didn’t masturbate, there was too much on my mind. I was looking forward to my solid A cup tits. It was going to make clothes shopping much easier went through my mind more than anything else.

Getting luggage together, making travel plans, building a museum travel itinerary with the school, plus finishing my driver school and passing my drivers test (yay!) occupied all my time in a hectic week. Mom and I talked about the trip incessantly. On Wednesday, I kept my usual appointment, but told Babe I would be in Europe for the next eight weeks. I made an appointment for the Wednesday after I was due to get back.

I told Tommy about my trip that afternoon, and we exchanged phone numbers. I promised to keep in touch, but you could tell he was upset. It’s not like I was his girlfriend or anything, we only had a coke together once a week for a couple of weeks, and even if I had been his girlfriend, he needed to get over himself and start thinking about me. To make matters worse, he finally screwed up his courage and asked me out on a date, but I had to turn him down, telling him I was way too busy before I left. He was even less talkative after that than usual and he hardly looked at me. He left as Mom was coming up. Mom, for her part, was pretty philosophical, when I told her about things. She told me that if the boy wanted to see me again, he’d be in touch. But it was a character defect as far as she was concerned. "Going to Europe is an opportunity he should be glad you are getting, and don’t be too sure you’ve seen the last of him, right now he’s just disappointed his hopes were dashed."

The operation was in Belgium, two days after we arrived in Europe and four days later. Everything was wonderful, though I hurt for a week or so. Mom was very stingy with the pain pills, but they just made me sleep anyway, and I couldn’t wait to be back on my feet and running around Brussels in a week. We spent a huge amount of time in the Royal Museums of Royal Art. We engaged a live guide and I took notes for my classes.

The best part was I looked sensational, like a real American Princess. Boys admired me everywhere. We went from there to Paris and then Madrid and Rome and Prague and Berlin, visiting the museums Mom had visited when she was in college and staying at youth hostels. We, of course, stayed in four and five star hotels and shopped, shopped, shopped. I bought shoes and purses and dozens of dresses and coats and hats, as did Mom. We had the stores ship them home so we wouldn’t be weighted down with too much luggage. We wore a lot of jeans and tennis shoes in Europe though I did have a little black dress and a pair of heels for anything that required them. My dress, in fact everything, fit better with my new tits. For the first time in my life, I looked good in crop tops and t-shirts with my braless breasts. I was in heaven.

When we got home, Mom and I had champagne to celebrate my diploma and I confirmed my appointment at Babe’s. It had been quite a couple of months, but I was ready to get into my new, adult, life. I fleetingly thought of the device, but decided to put off anything with it for a few days.

Sissy Story Chapter 02