Long intro this one, my first and I got carried away with the details. But it turns out well I think! Have changed the title as I've found a different story called The Bargain.
Being A Best Friend
I'd lived an average life. Myself, Carl, all of 15, just existing through school. I membered in no clubs, I had few close friends, and the gangs of boys that passed for the popular ones were constantly bewildering me with their distant, yet ever present judgement. Most of the time I just wanted to get back and play video games. I studied hard, I tried hard, and for all my reward I was an averagely liked, anonymous face in the crowd.
My sole parent, my mother Lucy was fairly poor. I never recieved a weekly allowance and managed to eek out a living in a paper round. Truth is, I was bored of life.
Until she walked in to it.
For better or worse, until she walked into it.
I'd been saving my wage for a new video game. My one greatest vice, it certainly passed the time in a dismal day. One day as I was delivering papers I found myself distracted by the most beautiful girl I'd ever seen and my bike careered into a fence. I managed to jump onto the grass as the bike went straight through the fence into the garden. An accident, but by the broken fence and shattered garden ornaments I knew this was bad news for me.
The newsagent was furious. Not only did I have to pay my wages to compensate the family in the house for their losses, I lost my job. I trudged home, defeated. I knew my mother would be understanding but letting her down was always a difficult task. I loved her and couldn't bare her being let down.
I opened the door and entered the kitchen and there, sat at the dining table, I found my mother, what I assumed was a friend of hers, and the angel of my earlier dreams. I nearly fell over at seeing her again. I never did learn my lessons.
My mother introduced us.
"Carl, this is my friend Judy. We met at school, and she has just moved in across town."
"Hi Judy" I muttered. To say I was shy was an understatement. Not usually was I lost for words, but this girl was intoxicating. A slim, pretty, brunette, with long hair, big brown eyes and a lot of style. She was going to be a hit here.
"And this is her daughter Jeanette. She is going to be attending your school. Why don't you show her around here?"
I didn't need to be asked twice. I beckoned her to follow me and what followed was the most bizarre and wonderful relationship I had ever known.
Part 2
We hit it off straight away. I found out that her father had left and in the divorce her mother had obtained a large portion of his wealth and decided to move back home up north. She shared my quirky sense of humour, she enjoyed my obvious nervousness, and was very playful with me. I never understood why she was, but I was grateful.
In school, she picked up friends easily, and we went our seperate ways, but out of it, she would often come around with her Mum, just to talk, do homework, and watch TV. We didn't share much in common, but it didn't matter to her somehow. I did my best to make her laugh, she effortlessly made me smile.
One day, we were talking about my video game collection, and I let her know about my paper round accident. She was very concerned. There were no physical scars but must be emotional ones, she inquired, and they must be deep.
I reassured her that the biggest outcome was "not being able to buy video games". Her concern was nice, even if it seemed over the top.
"If you can't save for them any more, how do you get new ones?" She asked.
"I make do with what I have". I said.
She played with her hair and giggled. "I could buy you one."
"I couldn't let you do that. Honestly, I don't like charity and I really couldn't do that to you. Thanks, but I couldn't!" This was my chance to score brownie points. I was generous and independent! Well, until it led to more time with her!
"No? I can afford it, silly! Well, what if it's not a gift? What if you do something for me next saturday for a job or something?" She was giggling, this felt like a game we often played. God she was pretty.
"Oh? Well, I suppose as a boss you'd be as good as anyone else! What do you have in mind?"
We reeled off one absurd situation after another, laughing wildly. One minute, I was going to keep flies off her the whole day. The next, I was going to torment her brother all day. It was a game. So when she looked into my eyes and turned it all serious, I didn't really have a chance.
"Well, seriously now, what if...I gave you a makeover?"
"What? You're going to turn me into Justin Bieber?" I laughed.
"No, not a boyish makeover...What if I turn you into a girl for the afternoon? I dress you as a girl, and you get a free video game".
I was taken aback. But looking into those eyes, I didn't really consider the full implications as I stuttered, "well, okay..sh-should be fun"...I immediately felt butterflies in my stomach. It would be fun. Strange. Embarrassing. Oh my god I really don't want to do this!
Saturday came slowly that week, but I couldn't say no to her. She was looking forward to it so much and it was true, I wanted a new game. A few hours fooling around would be okay?
Judy showed me to her room. It was large, feminine, and messy. Jeanette had been through all her drawers. Clearly this was important! She smiled and beckoned me in, slamming the door behind her.
"Oh my goddess this is going to be so much fun!" She squealed. I suddenly felt like a deer in the headlights. Then I noticed the camera. And the hair remover. And the outfits folded on the bed, with underwear. I started to look concerned.
"What's up Carl?"
"What's with the camera and the cream and the underwear? And the outfits? I thought I'd just be, like, putting on makeup and maybe a dress or something?"
"Oh?" She looked disappointed. "Well, I just wanted photos of the special occasion. And I wanted you to, sorta, be a girl friend for the day. Not just a boy in a dress. Isn't that what you thought as well?"
"It's a bit....much. It's too much. I'm really sorry, I can't go through with this!" She looked sad, but I knew she would understand.
"Well, okay, I'm really sorry I spooked you. I guess we got our wires crossed! Listen I have to tidy around here. No hard feelings okay? Why don't you call me tomorrow?"
I trudged home, sad. Sad that my day hadn't turned out the fun I imagined. Sad I'd let her down. Sad the video game wasn't mine. Mostly sad she felt bad about me.
Sunday was also a drag. I was bored. I wanted to call her, to make sure she was okay with me, but I couldn't. I was unhappy with hurting her feelings.
Part 3
School that week was spent hanging around the guys, trying to forget about her. I was too ashamed to see her. Of course, as usual I was a peripheral guest. Then on Thursday, I saw her again. Just stood there. Her big brown eyes. She smiled at me. I smiled back. We talked after school, at the lockers, as if nothing happened. I knew she was my friend for life. I knew that she cared about me more than most of her girl friends. I knew that I had to make sacrifices for her. Including my male pride for an afternoon.
I finally called her on Thursday evening. I'd come to a realisation.
"Jeanette? It's me. Look, I shouldn't have come over last saturday and got your hopes up like that, I'm really sorry."
"Carl....really it's okay. It was my fault!"
"No, it wasn't. You just wanted to have fun with me like I do when you're around here. When you come to mine, we talk about games, watch my shows, listen to my music...it's selfish. And you just wanted a bit of fun with your things. I was too proud to be your friend when you needed me. Too embarrassed. I'm sorry."
"Well, there is that...you fool". She giggled.
"Next Saturday, have you still got the game? If you do, I'll come through with my half of the bargain."
"Will you? Carl, I can't put myself through that again, it was so embarrassing for me. Will you be willing to just go with what I have for you? The whole lot? No matter what? You're not going to run?"
"...no...."I said, with some trepidation. This was not what I wanted, and I knew where it was heading.
"Bear in mind, you wont be a boy in a dress. You'll be a girl. You'll be acting like one. My mother will see you, my brother might."
"What?.....okay okay. I'll do it. If you could keep your brother off me it might be appreciated....okay I'll just go along with it, no complaints."
"Oh my goddess this is going to be so so much fun! You are my best friend ever Carl! Listen, tomorrow in school, I'll give you the hair removal cream, you can remove your body hair yourself so we don't waste time on Saturday!"
"My arms? Legs?"
"All of it?....come on don't back out now! No one will ever know! Oh and my Mum has called yours. You're staying over!"
The phone clicked. I was commited. I was shaking. Staying over with her was my idea of heaven, spending it as a girl, hell. But at least I wouldn't be bored.
To my surprise we met over lunch.We hardly ever spoke in school but she pretty much grabbed me. All eyes were on me, sitting with one of the most popular, beautiful girls in the school. We chatted as normal, laughed, cried, and I was, as usual, smitten. She handed me the cream as a parting shot. "See you tomorrow....Amy."
"Amy?" I asked. It was too late. She was gone.
When I returned home, my Mum asked a question which threw another layer of weird onto this. "Did she give you the cream?"
Judy had told her everything. They were both very enthusiastic. They had both agreed that boys should be more like girls apparently. And Judy had promised my Mum would see any photos, "as long as she didn't give them to anyone else". Which is what Jeanette had said to me!
My Mum was buzzing with questions. Every time I changed the subject she changed it back. Will it be a regular thing? Will I learn to act like a girl? What about perfume? Will I style like this, or this, or this.
To every question was a don't know.
She decided to help me with the hair cream. Then she started to teach me how to behave as a girl. How to sit, mannerisms, beauty tips. Her behaviour seemed to change. She was softer to me, more enthusiastic to everything I was doing, even sitting. She called me "sweetie" and "cutie" and switched over later to "Princess" which I hated. She also asked me to call her Mummy. Which again, I hated. But I did it. I loved her too much not to. She was not content tonight to leave me to my own entertainment, she wanted to get involved in my personal life. This was new.
She also sent me to bed. I'd had no bedtime for years. She had left me largely to my own devices unless i needed her, yet all of a sudden, I was treated like every little thing I did was important. I needed my beauty sleep apparently. And when I got to bed, she had changed my sheets to silk lace and insisted on tucking me in. I wanted to put my heavy metal T Shirt on, but she said I simply had to experience the feeling of hairlessness so was tucked in dressed solely in my plain white briefs and kissed on the cheek.
This was wonderous, yet shameful. Horrible, yet so warm. I drifted off to sleep feeling happy and yet very very anxious.
Part 4.
I was awoken by Mum, sorry, Mummy, at 8am. This was a big day I was told. She laid out plain white underwear for me, my skinny white jeans I hated and a T shirt that was too bright and too colourful. I put them on and went downstairs, where she had prepared Mummy's little Princess with some thin crackerbreads for breakfast. This was not turning out well. She seemed to have a daughter. I never knew she wanted one until now, but it was clear. She was making the most of this.
I got to Jeanettes at 9am. My heart pounding, I knocked on the door. It was answered by Judy. "Hello Amy!"
"Mrs Williams...my n-names C-Carl Ma'am." I stuttered out.
"Not today it isn't silly! Go on upstairs she's waiting for you!"
I walked upstairs slowly, my butterflies fluttering wildly, wanting to turn around and run. I knocked. The door was opened and she grabbed my top and pulled me in, giggling,"
"Carl!" She smiled. To my relief, my name. "Now Carl, I don't want you thinking you've been forced here, or that you can't pull out. So I'm going to ask you one last time, are you cool with all this?"
"Y-yes, I am. "
She pulled me towards her angelic figure and hugged me tenderly. "Okay Amy, you go into the bathroom and take a shower with the soaps provided, then put the bathrobe on and send all your clothes downstairs. "
"All of them?"
"You wont be needing them silly!"
I walked out of her room across the landing. Her younger brother Matt was on his video games. He was always friendly and nerdy. He managed a "hey" before returning to the game. He had no idea what was going on. I hoped it would stay that way.
I showered. The soaps, predictably, were very feminine smelling. I thoroughly shampooed my unkempt long hair and conditioned it. I didn't usually bother with either, but this was, according to my Mother, a special occasion. Then I scrubbed myself with the provided pink towel and used the deoderant provided. It was pink. It smelled pink. I smelled pink. Flowery. Girlish. Then I noticed the robe on the back of the door. I'd forgotten about the robe. It was thick, fluffy, pink again. This was not a colour I was used to.
I slipped it on. I caught the mirror image projected opposite. A hairless, girlish boy by now. I must have been exagerating, but that's what it felt like. I was already ashamed.
I darted across the hall and threw my clothes downstairs as I was told. Matt, as it turns out, was downstairs watching television, and the relief I felt was something I'd never felt before. Overwhelming. He wouldn't see me in this robe.
I didn't know whether to just knock or come in to Jeanettes room, but I decided to knock. The time it took for her to open the door felt like an eternity.
"Amy, you look fantastic! You're so smooth! You smell delicious girl!"
I blushed. These were technically compliments. I was technically half naked in front of the prettiest girl in school.
She sat me down and started brushing my hair. She brushed and brushed. "Well, I know one thing that needs doing!" She straighted it and parted it before putting clips in. Then to my worry she took out some scissors and evened it all out.
"We'll have such fun with that!" She started chopping all over the place, I looked distressed, so she turned around and held my hand. "Don't worry sweetie, it will all be okay." She was styling it! She put in curlers!
I fidgeted. "Are you sure this isn't....permanent?"
"Hey you, why do you care, you will look so divine! All the boys will be staring Amy!"
She then whispered, "I'll do my best to reverse don't worry we can shorten it later or something".
Next, she rifled through some bags. "I'm more prepared this time. I've not just gone shopping for games sweetie". She handed me some lingerie. The bottom, a pair of lacey purple briefs with black lace trim and a matching bra.
"Now, we can either be prudish like two strangers playing games or you can just change in front of me."
"What? Jeanette I don't think I can..."
"Honey, girls see each other, and you're a girl, Don't worry, I wont laugh or touch or stare. I promise! My Mum knows, she's cool with it."
Her eyes were intoxicating me again. I was already in over my head. I'd given up. This girl had me. I took the lingerie and opened my robe, slipping them both on. To her credit she never did stare or make a big deal of it. This wasn't a joke. I was her girl friend today. That's when it sunk in finally.
Then my nails were painted. She filed what was there.
I was uncomfortable. Not because it hurt to wear lingerie, or chaffed, or that I was too "big" for the panties. If anything I wasn't big enough for boxer shorts. I just felt out of place, strange.
I was embarrassed yet enjoying the time spent with Jeanette. I was deeply in love. Sat there in my tiny briefs which seemed to be designed to expose my lower buttocks and my totally unnecessary bra, all of a sudden I felt exposed. But she wasn't ready to dress me. So I sat there, getting my nails painted.
Jeanette seemed to notice my fidgeting and seemed downcast. This wasn't the way she wanted it. Again, I felt ashamed. She was wanting to enjoy this so much but I was spoiling it.
She stopped and perched herself on the bed. My heart sank. "Carl, I'm sorry, I shouldnt be doing this to you. Please, forgive me, we can go back to how it was".
I paused. This was again my fault. And there was no way I was letting her down twice. I looked at her face, plucked up the courage, and knew what I had to do. I thought about the lessons Mummy had taught me and put aside my reservations. This was going to be a blow to my manhood.
"Jeanette sweetie? What's up? Oh my Goddess don't cry" I crossed my legs and placed my hands onto my breasts, wrists out, I was clearly broadcasting concern. "I'm having the time of my life! I'm just nervous that I'll screw it all up!"
She looked up, suspicious, but grinning. "Are you sure, AMY? I'll give you the video game anyway you know!"
I stood, catwalked over to the bed, and perched myself next to her. I'm sure I needed a lot of work at this, but I knew she'd appreciate the effort. "I don't care about silly video games! I just want to be with you!"
That part, at this moment, was right. I just wanted to be around her. To see her happy. For her to be happy with me.
I toned it down. I got serious. "Jeanette. You are the best friend I've ever had. You've given me so much joy. I don't care what's normal, and I don't care how embarrassed I get. This is something you love, and I've promised. Let's get to it. No Limits from me like you said."
I picked up the girlishness and ventured on, as if to dismiss any such talk of going back. I was in this high, might as well go the full way. Can't get more ashamed than I already feel.
"You know Jeanette, being a new girl like this, I don't think I've ever worn a skirt in my life! Isn't that a shame?"
"Oh no sis, you don't escape that easy. You know it's time for your eyebrows!"
I gulped. This sounded painful and permanent. But I swallowed my pride. "Ooookay sweetie keep them neat!"
The plucking hurt. She giggled. I felt everything, and I didn't care. Her
eyes were so close to mine, Her hands exploring my face, her lips so close to mine I could almost feel them.
When she'd finished they were thin, angular, and I was shellshocked. The best and worst day of my life. I couldn't ever trade it.
Next came the makeup. Again, she was so close to me I could almost kiss her. She giggled. She stared into my eyes. She reassured me "This colour is in this year" and "All the boys love big red sparkly lips". Some reassurance! My lips were painted and puckered. My eyes in mascara, I could feel it there even when I was resting. Another constant reminder. I couldn't ignore this.
When she was finished I peeked into the mirror. Here I was, a boy of 15, with a slim, small, figure, in lingerie, with makeup and girlish hair. I looked like a girl. Now I looked so far from being masculine I couldn't imagine what it felt like. I was surrounded in femininity. The girls room, the flowery smells, the clothing. I felt trapped. But if I'm being trapped there's no one I'd rather be trapped with.
To be continued
Betty Pearl's Sissy Stories 20.1
Topic: Being a Best Friend (Read 18423 times)
