Sissy Story Chapter 02 by A.+N.+Pervert

Rating: 88%, Read 12479 times, Posted Jun 02, 2017

Fiction | Authoritarian, Transsexual

Mother and Sissy

Mom and I had obviously taken things to a different level. Just like when I had first worn pigtails and hair ribbons, our relationship, and understanding of that relationship became even more intense and our connection became even deeper. I was happy and Mom was obviously pleased coming out of the mall, me wearing clothes bought that day; a light t-shirt, some shorts, sandals that showed my toenails polished, panties and a training bra. She pushed a cart full of things for my new wardrobe. She chatted constantly about her Sissy and the things we could do and how much she was enjoying life.

On the way to the kiosk to get my ears she had leaned over and kissed me on the head and emphasized how proud of me she was. It was really intoxicating. We picked out the starter earrings together with the teenaged girl doing the piercing. Seemingly not paying attention at all, Mom put the big white purse we had bought in my lap to hide my beginning erection. Though it hurt just a little, I was giddy as the girl pierced my ears and put in the little gold hearts. I kept the purse in front of me the whole time and left the kiosk and walked to the car with Mom pushing the cart. It was both embarrassing and very intense. Mom and I hardly talked until we got to the car and she had returned the cart, without saying a word. It had been an exhausting day.

We put away my new wardrobe, in my new room. I had an erection the whole time. Mom must have noticed, but she still didn’t say anything about it at all. She did decide to call a professional moving company to pack up my old room, so we got out the very few things I wanted, school assignments, a couple of books, some photographs and moved them to my new room. I left the heart shaped frame with the picture of Mom and me in its pride of place on my nightstand. All this took a couple of hours and, when we’d finished we went downstairs for supper; cold cuts, chips and soda at the kitchen table.

We talked about making an appointment for me at the beauty shop, where I could get my hair professionally styled. I didn’t want to go to the same shop Mom did, it would make for some embarrassing questions I really didn’t want to answer. It was sort of like our normal conversation, Mom coaxing me to go further, me playing coy, the difference was I had no intention of going to the beauty shop Mom went to and facing those women, and something absolutely had to be done with my hair.

During our conversation about my hair, I had something else in the back of my mind. Everything had changed with Mom and I and so it felt like the time to drop my bombshell and asked her point blank about my penis. I’d missed sex education in the Public School and I asked her why it got bigger, and stiff, and what I could do about it. I told her it made it embarrassing in public. For one of the few times in our lives together, she was speechless for a moment. Then, she explained why things worked the way they did and then promised to get an online sex education course for me. She said doing something about the erections is trickier. She told me the vitamins we took every day ought to help, since they had female hormones, but they don’t work the same way for everyone. She told me about a ‘gaff’, which is an article of clothing, but she said they sort of took the place of panties, and she liked the idea of me wearing panties. She asked me if I liked the idea of wearing panties and I admitted I did, but that just made things worse. Even sitting there talking about it was exciting me. She smiled and said, “It’s so cute sticking out like that in your girl’s clothes. It won’t necessarily be so cute going out in public, but we can manage that as things happen. Besides, it’s instant feedback, it tells me what you like.”

I thought about this and asked her if she was really happy I was a boy. She smiled and said, “Definitely! It makes everything more fun, maybe a little bit more of a challenge, but definitely more fun. You acting in ways that please me, and learning to really enjoy acting like that, gives me real pleasure. The enjoyment I’ve had the last couple of years, doing your hair, convincing you to go out with me, watching you get erections as I coaxed you to go further and just showing you off has made my life a joy, instead of what it was before. I don’t know how I would have made the last few years without you, and your great attitude and willingness to take a chance. We have a special relationship. You’re a momma’s boy. I love that. It makes me feel especially good. I love coaxing you into doing more.”

I thought about it. "I’m afraid everyone at the beauty shop will find out I’m a boy and embarrass me.”

She looked at me with that sly look and leaned over and whispered, “What, are you afraid Mommy is going to talk you into going to the beauty shop to dye your hair platinum blonde and put it in curls or are you afraid I won't?”

I almost had an orgasm right there. She smiled, “You’d have to go back regularly to keep it up. But it does sound like fun, doesn’t it?” and she lifted her glass to her lips and looked me in the eye.

“Mom, please!”

“Well, let me see what Mommy can do for her little boy. Maybe I could find someone who will come to the house and do it. You know, dye it blonde and put it in a bunch of barrel curls? Does that sound OK? But I promise you, and do I ever steer you wrong? You’ll enjoy going to the beauty shop. You’ll have fun going for a regular appointment just like all the other girls. You can have your nails done at the same visit, like I do. Only the girls working on you will be in contact with you, and they’ll love you. Just be sure and tip well. And it will give you someplace else to wear your cute outfits. Nobody is going to think anybody as cute as you is a boy.” She smiled.

My erection strained against my panties and shorts. I thought I was going to keel over but with all my will power I managed to stay in my chair. I swallowed and looked at Mom.

“There’s no use trying to deny it, you know,” she gestured toward my crotch. “We both know you really like the idea of dressing up and going to a beauty shop, and getting that hair platinum blonde hair in curls,” she said, smugly, fingering my hair and grinning and looking at me. “Well, you don’t worry, pretty little boy, Mommy will help you get that hair all golden and curly just like you want it, so her little Sissy can look cute, OK?” She stopped and looked at me for a second. “Just think, Sissy, in another few days, maybe a couple of weeks total, you will have gone dressing like a boy, albeit with your hair in pigtails and ribbons and just a touch of makeup, and living in a boy’s room, to dressing in nothing but girl’s clothes with dyed, curled hair and wearing nail polish and makeup all the time outside the house and sleeping in a room, by your comment, fit for Katy Perry. You’ll have become a real girly girl!” She pinched my cheek grinned. “And the best part is, while you love it, you are doing it just for me, Mommy.” She hugged me again. I swear I almost came, right there, when I was in her arms.

That conversation capped off our wonderful day. I then went up to my new room while Mom went on the computer. I masturbated several times that night, into one of the pink towels. Life was good for the right kind of boy!

In a couple of days she announced, “You’ve got an appointment at Babe’s Beauty Shop on Wednesday afternoon at one. She’ll do your hair and have a tech do your toenails and fingernails. Don’t worry, I have confidential information that you are not the only boy they have for a customer, they’re used to it so nobody will think a thing of it. And I will be right there, watching over you.”

Wednesday both seemed impossibly far in the future and too quick for me to be ready for it. When it finally came, I spent all Wednesday morning working out what to wear, trying on outfits, rejecting them, selecting shoes to go with them, constantly asking Mom’s advice. I was mentally exhausted by the time we left for Babe’s. It only took a few minutes to get there and I was totally quiet for the entire trip. Mom kept up the chatter, telling me how pretty I was going to look, how much I’d enjoy it and advising me to stick close to her in the shop. “Don’t go wandering off, now, we don’t want you in the line for red hair!” “MOM”, was my first word on the trip.

Babe’s was in a new mall, fairly close to our house, in a very exclusive part of town with all sorts of high fashion shops with beautiful clothes and jewelry. I noticed this even in my fog. Mom and I walked into the shop up to the receptionist, “Ann Marie Quinn and Sissy, here for her one o’clock.”

“Just a minute” and she pushed a button. “Ann Marie Quinn is here with Sissy.”

An older blonde woman with a big smile came out and introduced herself as Babe. “Let’s look at you”, and she fingered my hair and looked at my nails, which I had done myself. Pink.

“Good. Follow me. I’m going to do your hair. I’m going to give you a book with several pictures for you and your mother to look at and decide which look you want. After your cut and dye, I’ll have Alice come by and you all can pick nail colors. This is going to take about three hours, so be prepared. Is Mom going to stay here that entire time?”

“Yes”, I blurted out.

Mom laughed politely. “It’s Sissy’s first time and I think a little company is needed.”

“We won’t bite”, as she walked through some swinging doors into a long hallway with several people in chairs with mostly women but a couple of men in pink aprons hovering around them, and she said back over her shoulder, “no matter how cute our customers are.” I was horrified, but I was the only one who reacted at all. All the racket and noise of the beauty shop continued, and there was plenty of noise as several conversations were going on. The world did not stop when the three of us entered the room and it didn’t stop when we talked. I actually relaxed a little. Babe led us to an empty chair in the middle of the aisle.

“This is George, he’ll shampoo your hair while your Mom and I watch and talk.” A short efficient looking slender man with glasses came up and began putting a gown on me. He took my sunglasses and handed them to me with a disapproving stare. I gave them to Mom, who put them in my purse.

Mom and Babe kept talking. George kept walking around and finally turned my chair around and bent my head down, over a sink, and started washing. I was too startled to say anything and, after rubbing and rinsing and squirting he said, “Up” and began drying with a towel. “Your hair is perfect. Maybe it could use a little color, because there’s nothing that can’t be improved, right?”

I tried to nod but he was vigorously drying my head so I cleared my throat and said, “Yes.”

He finished with an “All done”, and walked away.

I said, “Thank you” and looked at myself in the mirror. My makeup was still mostly intact, but my hair was wet and stringy. My gold heart earrings seemed out of place. My bare legs stuck out of the bottom of the gown with my rhinestone flip-flops and pink toenails. I kept my hands under the gown. I didn’t think I looked very pretty, I’ll tell you.

Babe handed me a book and pulled Mom up a chair. “You all decide while I get a couple of things done, and we’ll get started when I get back.”

There were approximately one million different hairstyles and color combinations in her book. Mom seemed undaunted as she stopped on a page with curls that had “barrel curls” at the top. I looked at them and felt myself getting a hard on. Without looking closely at me, Mom casually put my purse in my lap covering it. I can’t believe how she was able to do it without calling attention to it, or what she was really doing, at all. Mom had gone to the right page and we picked out a style and Mom wrote the page number and letter on a notepad. Then we started looking at colors. She turned right to the blondest blonde in the book. I thought I was going to cum right there in the beauty shop. We chose the ‘Harlow’ and we were ready for Babe.

Mom chattered, trying to calm me down, and smiling that secret smile the whole time. Babe was coming back when Mom leaned over and whispered, “My Sissy is going to look so cute.” I blushed.

Babe looked at the style, cut and color and said, “OK, we’ll fix this one for you. Are you going to keep your purse in your lap? OK. Good. You are probably going to want to get a curling iron to maintain it yourself, unless you want to come in every day?” Her chatter was constant and so was her smile. I liked her.

I replied, “Yes, I’ll keep my purse and OK.”

She threw a covering over my purse. I noticed several of the ladies had them.

“Don’t worry about keeping your curls up, we’ll show you how, and there are a million videos on Youtube to refresh your memory. Just find the one you like that looks like your style and watch it until you feel comfortable with all the steps. Every Wednesday, we’ll refresh it and check to make sure you are doing the right thing, retouch the color when it’s needed and do your nails really cute. OK?”

I nodded.

She started walking around the chair, first looking at my hair, then cutting, standing away, looking and cutting. Hair was falling all over the floor. I almost panicked before she stopped. When she turned me around to see myself, my hair was above my shoulders and shorter in front than on the sides. I looked a lot different after that first cut, I can tell you. In fact, that first afternoon was some experience.

When we finally got around to it I found out the dye burned. Nobody told me it would really hurt. It hurt a lot more than the ear piercing. I hung on to my purse in my lap for dear life the whole time. I only released it when the nail technicians came and my head was burning. Thankfully Mom selected some very red nail polish for my toes and darker red for my fingers. They put rhinestones in my big toenails. I have to admit it did look cute. My balls started to hurt I had had an erection for so long by this time. Like so much this experience was both embarrassing and exciting. I was constantly on edge worried about being caught and constantly delighted when I examined the results of their work. When they finally had finished, I was calmer.

Mom stood in front of me as we took the gown off, and gave me back my purse to hold in front. I looked unbelievably cute. I mean before I’d come to the beauty shop I don’t mean I didn’t look cute, because I did, but now I had bleached hair and a professional manicure and pedicure and, in addition to looking older, I looked better. I was very happy with the results.

On the way out, Mom and Babe stood with me as I made an appointment for the next Wednesday. By the time we were in the car, the daze was beginning to wear off. I couldn’t keep my eyes off the mirror app on my phone, wherein a pretty girl stared back at me. I turned this way and that, smiled, fingered my hair and watched the pretty girl do the same. My hair was wild, like a movie star’s, and my sunglasses were the wrong color. God, pink was awful with the nails. I needed some red ones with red frames. And maybe, if it wasn’t too much, white scarf with red polka dots or hearts. I didn’t cum in my cute clothes, but I wanted to.

Mom said, “You’d better calm down, we have to stop at the drug store and get you that curling iron, or did you forget”? She couldn’t quit smiling.

“No ma’am”.

She laughed, “I was wondering if you thought you were too pretty to talk to anyone”.

“No ma’am”.

“Well, do you like it”?

“I love it”. I looked down at my pretty toes with the rhinestones and wondered how they’d look in high heels.

“I can see, actually”, she nodded toward my lap. “We’ve got to do something about that. When you get home, I want you to Google ‘stopping an erection’ and that sort of thing. Find out what your options are, and we’ll talk. You need to do this, not me”.

We stopped at the drugstore, I got the curling iron and some red sunglasses and we went home. It had been a long afternoon, but I made it home without an orgasm and I loved the way I looked.

I spent hours on the Internet looking at information about erections. I didn’t want to take drugs and I didn’t really find anything. Some of the “Old-fashioned” ways looked promising, but nothing modern. I talked to Mom about it. She asked, “Old-fashioned”?

I showed her a page with patents for devices for hiding erections. She said. “I see. Maybe looking here might help. Tell me what you think”.

She typed in ‘male chastity devices’ in Google and went away while I explored.

I couldn’t believe it. Even Amazon had them. This must be a common problem. I looked them over. They had locks, but why would I want a lock? As usual, I went and asked Mom. “Well, you won’t get an erection and, if someone else has the key, you have to ask them before you can”.

“But why would I want to ask someone else”?

She smiled and brushed my hair, “That way, the other person can control your erections. For instance, if, today, I had your key, I wouldn’t have given it to you in the beauty shop, so you wouldn’t have had an erection”.

“But Mom, why couldn’t I just put the device on and leave the key home”?

She grinned, “Is that all the fun you want to have? Would you keep yourself locked up for a week for instance”?

My eyes got big. “But what if I wanted to cum”?

“How could you? That’s assuming, of course, you couldn’t convince them to agree it was time for you to cum”. She looked in my eyes.

“But, they’d agree wouldn’t they”, I wailed?

“Not necessarily. Maybe they thought you needed to learn a little discipline. Or maybe they knew better than you what you wanted in spite of what you said and wanted you to do that thing before unlocking you”, she gestured at my erection which was fully sticking out.

“It’s just another way to have fun. There’s no right way. Maybe they’d leave you locked up forever”! She smiled and kept adjusting my blouse and stepping back and looking at it and patting my shoulders. I didn’t know what to think. Mom wouldn’t do that to me, would she?

She finished fiddling with my clothes, “Now, where were we? Which device is it you wanted?” She gestured back toward my erection, as if getting it were already decided.

I took her to the computer and showed her one that had a belt and a smooth front with a pocket inside it for the penis and a couple of straps going up the back.

“That one does look secure. You have to be sure, though. I mean changing your mind after that lock snaps shut wouldn’t be possible, what would the point be? Of course, when that lock snapped you wouldn’t really have to make any choices at all. You’d just have to do what I say. You’d probably be doing all those things you really want to do, but are afraid to ask for. Mommy knows what you want and, more importantly, what you need. It has to be your choice though. You understand that, don’t you? Right now, we only do what you want, if I had you all locked up, we’d only do what I want. Now, do you want me to order it, it’s a choice you get to make before the last one, to close that lock and give me the key”. She smiled and brushed my cheek with her hand. “Sissy is so pretty. I’d like to boss her around all the time, just as much as she’d like me to boss her around”. Mom shook her head up and down. “I’ll bet I could dress Sissy up as a maid, a pretty French Maid, and invite some friends over for her to wait on. Or anything, maybe put on fashion shows for my friends, anything, anything at all”. She just kept nodding her head up and down.

I had an orgasm right there. Mom noticed and waited. I finally asked, “If we ordered it, so I could see it, I wouldn’t have to put it on, would I? Or if I put it on, I wouldn’t have to lock it?"

“Nope. You could look at it just like you looked at those clothes in the closet in your old room for so long. You could even put it on and wear it around while it was unlocked, or even lock it and keep the key yourself. When or if you want to bring me the key, you will”. She brushed my hair. “Come on." She took me by the hand and walked me to what was now my closet and stood with me in front of the mirror. I looked good, certainly. My hair was platinum blonde, and in a million curls. I was made up, and I could see my heart earrings, as I looked at myself, all the way up and down, sleeveless blouse, shorts, bare legs and flip-flops with rhinestones and rhinestones on my toes. I looked really good, really good. And I had an appointment the next week at the beauty shop so I’d keep on looking this good. How much further could I go?

I frankly didn’t know. At that time, I hadn’t had any experience. I didn’t know what people were like, or even what I was like.

“Put on some high heels and practice walking in them”, Mom said.

I looked at her and did as she said. I got some red patent leather open-toed sandals with a four-inch heel off the shoe rack in my closet and sat on my bed and watched myself in the mirror put the heels on. “It’s fun watching yourself, isn’t it”? Mom laughed. I looked at her and lay back on the bed and extended my leg in the air and looked at it, and looked back at the mirror.

“Now, we should get that ordered if we want it here tomorrow."

I followed her back to the computer and watched her order it, specifying next day delivery. I hugged her from behind and watched. I wore the high heels all evening, practicing walking too, but mostly watching myself every chance I got. 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.

Rating: 88%, Read 12479 times, Posted Jun 02, 2017

Fiction | Authoritarian, Transsexual


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