We were heading out of the coffee shop, she wanted to show me what she was going to buy her older sister’s baby for his 2nd birthday so it was off to the toy shop, when Matt walked in. When I say he walked in, what he actually did was incredibly goofy. Effy opened the door as he was walking in, he put his arm out to hold the door open but put it in front of her. To start with I thought he wanted to stop us from leaving, but no, he was just being a goon! He stumbled about for a couple of seconds, but it probably felt like an age to him, before he moved out of the way and held the door open for us. I put on the cutest voice I could manage and just said “Hey you! Thank you for holding the door open, you gentleman you!”, I did a sort of twirl as I walked passed him, Effy was watching him as I walked away.
“You minx. He watched you walk away! He checked you out big time! He so wants you”, she said, as we walked around the corner from the coffee shop and she linked arms with me. I blushed a little and could feel a stir in my groin. I was glad I was wearing a gaff, without it the front of my skirt would have lifted up for sure.
Myself and Effy went window shopping after the toy shop, mainly killing time, my bus was due to leave 20 minutes before hers, so we looked around in most of the clothes shops. She bought a couple of tops in Primark. She was trying to get me to buy something to wear for my date with Matt, but I had no money, and I didn’t want to use my card, or should I say James’ card, in New Look or River Island. I pretty much made my mind up about what I was going to wear, with Effy’s help. We found the tights first, they were an electric blue colour. I found a dark blue top with flowers on, it had an almost exact electric blue in the flowers too, so I figured it would work quite well with the tights. After ages looking around at skirts, I turned to Effy with a fed up look on my face.
“I might as well just wear that black tube skirt I bought on Saturday, the one that would be ALMOST too short for school, but could get away with it with tights”, I said, surprised that the choosing of an outfit was going so well. Effy agreed.
“Yea, and you could get away with wearing it shorter than you would to school too, pull it up a bit, it’ll pull in your waist even more and the top will sit over it. Nicely. Put the top on now, you’ll get a good idea of how you will look.”, She wasn’t condescending, as much is it sounds it now, looking back, she really wasn’t. It was sound advice, which I really appreciated. We went back to where we found the top, I took my cardigan, tie and shirt off without even thinking about what you could see! The black top I wore under my shirt that day covered me enough to not see the breast forms. I pulled the top over my head and flicked my hair out.
“How does it look?”, I said to Effy, who put her hands on the waist band of my skirt and pulled it up. I jumped a little, “Right, look in the mirror. I think that should be how long the skirt should be. Imagine your black tights are blue. What do you think?”
“I think this is perfect”, I said, smiling at my reflection. It looked perfect. The skirt wasn’t ‘right’ as such, but I could see the length that would work well with the tube skirt. I put the top back on the rail and put my shirt back on, not buttoning it up as much as normal, and I just pulled the tie up until it sat just about where my cleavage should start. We headed off to the bus station after that, I had about 10 minutes before my bus left, so I didn’t want to see anything else that I may or may not end up buying.
I got home, Beth was still going to be working for about half an hour, so I decided to get changed back into James before meeting up with her. I hadn’t seen her without wearing my new school uniform in just over a week. So I wanted a change as much as anything.
“JESS!”, Lucy shouted. She stood mid-walk just staring at me.
“What?”, I asked in a brattish tone. I had no idea where it came from.
“You look like a tramp! Have you warn your uniform like that all day? You looked cute when you left this morning, and now you look like a slut!”, she never complained about anything I had worn before, I wasn’t sure what she was going on about.
“It’s just one button more undone than normal, that’s all”, I said, thinking that is what she was talking about.
“And what about the fact that your skirt barely covers your arse?”, she sounded angry still.
I went to grab where the hem would normally be. “Shit” was the only word that came into my head. The hem was at least 2 inches higher than it was before Effy pulled it up. It would have been fine if the skirt wasn’t pleated, but the skirt lifted slightly as I walked anyway, so who knows what people saw in between me leaving Top Shop and getting home. I explained everything to Lucy and she just shook her head.
I had a shower, removed the smell of girl and covered myself in body spray. I don’t think I had smelt like a boy for 2 weeks to be honest. It felt unusual. And I was lucky to find the deodorant that I sprayed on me every day up until a couple of weeks ago! I got dressed and sat down at my desk, and put the headwrap on to keep my hair out of my face. I put on a layer of foundation and was about to start to apply some blusher when I realised what I was doing. I was on auto-pilot, it was my standard routine after putting clothes now. It wasn’t the first time I had made the same mistake.
After washing the makeup off, I decided I would take Jess with me. Just in case Beth wanted her to come. I packed the tube skirt I was intending to wear on my date with Matt, a tee from Primark that Lucy had bought for me on day 1, and the superdry hoody that I bought on my shopping trip with the girls. I didn’t have space to put Lucy’s ugg boots that I had now claimed as my own, temporarily, so I went with the pink flats that I bought to go with the hoody. Underwear, wig and breast forms in and my bag was pretty much full. I just managed to fit my small makeup bag that I take to school with me, just in case I need to touch up my makeup during the day, in my rucksack.
“Just about to finish work babes, looking forward to seeing you! I’ve found a job you may be interested in. Meet you in 10? xxxx” read the text that Beth sent to me. A job... Ok, I knew I should get a summer job, but where had Beth found? I guess I would find out soon enough.
I rushed down stairs.
“JAMES!!”, Lucy shouted as I opened the front door.
“WHAT?!”, I shouted at her, pissed off that she stopped me once more.
“James, seriously. What are you doing?”, she said, “I can only assume you want to get caught out.”
I had no idea what she was going on about. I just stood there, my left hand on my hip, my right hand holding onto the strap of my rucksack. I quickly adjusted my posture to more of a manly stance.
“James, I know you have spent the past week or so as Jess, but if you’re going to go out with no makeup and no wig, you could at least make sure that you were wearing boys jeans.”, She said. Her voice was calm, and sympathetic.
“What do you...”, I then realised, I felt the draft. I hadn’t put on my jeans! I had my boxers on, I didn’t have a bra on, I was wearing a green t-shirt and a baggy black zip up hoody. But instead of me putting on my jeans, I had involuntarily put my school skirt back on, and I was wearing Lucy’s uggs. I must have just put the uggs on because I was thinking about taking them with me. “Oh shit it.”, I said in a hushed voice as I dropped my bag to the floor and rushed back up to my room.
10 minutes later I had my arms around my gorgeous girlfriend. I kissed her as if I hadn’t seen her for an age. She was in her work uniform so she wanted to drop home and get changed. She worked in a pub as a waitress, so she wore a black top and either a skirt or trousers. Today, she was wearing a black shirt and a shortish tube skirt with what looked like 50 denier tights. She was wearing a black strappy top under he shirt to cover more of her cleavage. The work shirts she wore were really tight around the bust. It wasn’t lust that made me attracted to her today, it was the fact that I wanted to be wearing what she was, she looked pretty and sexy. I think the spending time chatting to girls was changing the way I thought more and more. The lines between James and Jess were being rubbed out.
“You’re mincing”, Beth stated as she stopped in front of me, her hands on my chest, “If you are going to keep walking like a girl and checking out men’s bulges I am going to get annoyed. Snap out of it will you. Please.”
She sounded annoyed, she looked upset. Was it jealousy or was she scared that I was becoming attracted to men, not that I was, I was just comparing other guys to Matt. Wait. What was I thinking? The fact that she mentioned the men’s bulges frightened me a little, was it that obvious?
“I’m sorry. I really am. I’ve just been so used to having to be able to comment with the rest of the girls and be quick. It’s so tough. I won’t do it again.”, I said, kissing her on the forehead. She put her arms around me and squeezed me tightly, then grabbed my hand and dragged me into the charity shop we were stood outside.
“Look at that outfit!” She said, excited, pointing at this dress, it had white tights and a blue headband on the hanger with it, “You would look so cute in...”. I was so glad there was nobody else in earshot!
“Are you actually serious Beth? You’re going to have a go at me and then this?” I asked, confused.
“Come on baby, I want my Jessy Wessy to jump through the rabit hole and be my Alice”, She whispered into my ear. I felt a stir in my pants. I was excited, wouldn’t anyone be?
“I’m not sure Beth, I said. Will it fit well?”, I said, knowing that it would fit me if it fit her, her waist was just a little smaller than mine and she was about an inch shorter than me. She knew what I meant.
“Tried it on whilst I was waiting for you, I finished work early, I saw it here on my way to work this morning and wanted to see if it was still here. I told them that I wanted you to say if you liked it or not before I did. They put the sold, awaiting collection tag on it for me so it would still be here. “, Beth explained, I didn’t know what to think. I didn’t have a suitable bra to wear with it, and Beth’s bras were all bigger than mine. Why I worried about having a matching bra I do not know, but clearly it was important.
“I need to get a strapless bra for this, you wanna come with or are you gonna wait somewhere for me?”, she asked, I opted for the waiting somewhere for her, I just sat on a bench just up the road. Everywhere was just about to close so I couldn’t be bothered to go anywhere.
We got back to Beth’s just as her parents were leaving for a dinner party. “I haven’t prepared anything for you to eat guys”, her mum said as she walked past, “Is that an Alice dress?”, she said, looking at the bag in Beth’s hand.
“Yea, it was a tenner, it fits, so I figured, why the hell not?”, Beth said, her mum looked at me.
“This your Halloween costume for this year is it James?”, Tracy, that’s Beth’s mum, said to me with a grin on her face.
“Nah, I’ve decided I would probably suit a St. Trinians to be honest”, I said, not realising I was talking in Jess’ voice.
“Well you sertainly have the, erm, frame to pull it off”, Tracy replied, you could tell she wanted to comment on the voice she had just heard. She left us, Beth looking at me with an expression of “Why on earth would you do that infront of my mum?” on her face.
So here we were, home alone, Beth went to her room, I followed her as per the norm. I sat on her bed whilst she took her hair out of the tight ponytail she had it up in.
She turned around and pushed me back on her bed. She was fairly spoilt, so her king size bed was enough to make anyone feel small. She straddled me, her crotch touching mine. Her hands on my stomach. I felt like the petite little girl again.
“So, this job. Theres a waiting staff job going at work. We can spend more time together over the summer if you take the job”, she said, as she rolled off me, snuggling up next to me.
“Oh cool, that sounds like a good idea. Just waiting? Or do they expect me to be a dish pig as well?”, I asked, knowing for well that they made her do the washing up sometimes, purely because she never made a fuss, she just got on with it.
“They’ll make James do the washing up”, she said looking straight up to the ceiling. She didn’t say anything else.
It sunk in.
“You told them you have a friend called Jess who has just moved into the area and want’s a job didn’t you?” I asked, she jumped off her bed and went to her wardrobe.
“Strip. Get your underwear out of your bag Jess.”, Beth ordered, as she got opened both the doors to her huge wardrobe. She chucked a black tank top at me. I pulled on the gaff and knickers at the same time, I’d gotten the tucking perfect now, so on went the bra and breast forms. I put the tank top on and grabbed my wig. By the time the wig was on Beth had gotten a shirt and some tights out for me. She also got a pair of her old school trousers.
I say old school trousers, because these were particularly tight, they were boot-cut, but they hugged the skin from waist to knee, they accented the arse, hips and yea, you get the picture. Beth wore baggy trousers to work now.
I grabbed the trousers and put my feet in them. “Wait.”, Beth interupted. She chucked a skirt at me, it looked way too long for anyone that worked with her to wear. I chucked it back at her.
“No way am I putting that on! I’d look like a twat.”, I said calmy. I grabbed my long blonde hair and put it over my left shoulder as I bent down to grab my little tube skirt out of my bag.
“Here we go. This will do won’t it?” I said as I pulled the tights over my knees. Beth walked out of the room and so I adjusted myself and started putting makeup on. I was just guessing that she wanted me to go the whole hog.
A couple of minutes later and she came back, she had a pair of shoes in each hand. She got down on her knees and spun the computer chair that I was sat on, she put the first pair on my feet. They were black with a small heal, probably about 3 inches. This was the first time I had worn heels since this whole thing started. She told me to stand up and look in the mirror. My legs looked so long, way longer than ever before. I had put a hair band around my wrist whilst doing my makeup, so I quickly worked my hair into a low pony tail just to see how I would look like if I did embark on a summer as Waitress Jess.
Beth came and put her arms around my waist from behind, leaning out to the side and looking at me through the mirror. She smiled, and I copied.
“I love you so much Jess, I’ve missed you baby.” She said in a really soft voice, she had never looked at me like this before, it was lustful and guilty all at the same time. She went on tip toes and kissed me on my neck. I turned around and looked at her, I knew that I looked like a girl who was about to embark on her first contact with another girl. Ok, so about a month ago I had a night of fun with her, but that was before I felt like a girl. Yea, that’s right, I felt like a real girl now.
We fondled a little bit, we played with each other, she never touched my crotch, it was is if she was avoiding my cock, as if she was imagining that it didn’t even exist. She opened her bedside cabinet’s top drawer. I knew exactly what it was in her hand without even looking. She put it in front of my face and looked at me with eyes that told me exactly what to do. I opened my mouth slightly and push my head towards it, I poked my tongue out a little, it made contact first with the silky soft texture of the fake pink phallus that had been presented to me.
Beth didn’t force it on me, she just held it in the same place. I pushed my mouth over it, my lips holding it tightly, I pulled my head back and forth for a little. Then, I pulled away, the slurp noise I made was familiar from the porn movies I had seen in the past, and from the couple of occasions that Beth had given me head. I blushed as Beth giggled.
She put the dildo back in her drawer, I never saw it again. She was just teasing me, testing me. We kissed a bit but nothing more, I hadn’t made plans to do anything or go anywhere but Beth had. We went to the cinema, after I changed out of the potential future work wear and back into my male clothes. The film was average, I walked Beth home and went back to mine. It was fairly late, nobody else was still up, so I went to bed.