I showered, Underwear on, the new bra that Beth had bought for me would be tested out well today, put tights on but wore trousers instead of a skirt. I was scared, what it someone saw me last night looking like a total slut? I chucked on some makeup, a little bit more eye liner than normal, but hey, I figured why the heck not. I didn’t bother with a vest top under my shirt, it was too warm for that. Besides, the new bra was white so it wouldn’t show through my tight white shirt, which was tighter than normal since the new bra made my boobs bigger than before.
I put the wig on last, as normal, and put it into a plaited it. It didn’t feel right. So I took the the plaits out and and sat there. What on earth could I do with it today. Time was running out so I grabbed a blue headband that my Mum had bought for me because it ‘works well with your eyes, and it’s cute’. That worked well. It had small pink flowers on, so I wiped the light blue eye shadow I had applied and replaced it with a really light shade of pink, you couldn’t notice that it was there unless you knew it was there, which was pretty cool. I grabbed a baby blue hair tie and put my hair into a loose ponytail.
I grabbed my rucksack, grabbed the small makeup bag, put the pink eye shadow in it and then chucked it into my school bag. I didn’t know whether I should take a skirt with me just in case I changed my mind about wearing trousers. And then which one? The one that Lucy bought me was simple, it folded down quite small, but then so did the other ones. It was either the same one from the day before or the tube skirt. I was going to miss the bus if I didn’t get my ass in gear, so I chucked the tube skirt in my school bag and left for school. Grabbing the pink phone case, I’d swap the black one for it when I got on the bus.
The day went by fairly quickly, up until lunch. Charlie linked arms with me and dragged me to the loos after leaving Maths.
“So, what are you going to wear?”, she asked. “Effy said you were going to buy some new clothes for your date with Matt tomorrow. Go on, what you chosen?”
“Come with me after school, you can see the outfit in full”, I said, grabbing the skirt out of my bag. “I brought this one with me so I could get a feel for exactly what it would look like”
“You should so wear that this afternoon! We have English with Matt this afternoon, you should give him a preview”, Charlie rushed to get the words out, I think she was more excited that I was.
I got changed into the skirt, as I put my trousers in my bag my phone vibrated.
“Beth told me about your date on Wednesday with that Rugby boy...”, It read, it was from Lucy.
I replied with “And?” and chucked the phone in my bag. Charlie and I went to grab some food, I wasn’t hungry so just bought a small orange juice carton. We were walking to meet the rest of the girls who were in a different Maths group to us when I heard someone shouting “JESS!”, it was Lucy. She made some stuff up about talking to her about the issue I had with Biology, I had no idea what she was talking about, but agreed to find her before next lesson.
Me and the girls chatted like me normally did, giggling at stupid things and talking about what we were going to do this summer. I told them how a friend from back home had found me a job in a pub as a waitress. Time flew, and it was time to find Lucy.
“You need to sort your hair out”, she said, “It hasn’t changed, grown or anything in the past couple of weeks. I’ve spoken to Tammy, she said she will cut it and whatever tonight after she has closed.”
Tammy was an old friend of Lucy’s who had started working in a salon a few months back, she did Lucy’s hair and always did a good job of it.
“What do you mean? Sort it out? It’s a wig, surely it’s fine?”, I asked, not quite getting what she wanted me to do.
“Look, I think you should get it dyed, layered and just improved. Most girls your age are doing it, and your hair just looks too natural. Here”, she passed me a torn out page of a magazine, it had a woman with a hairstyle very similar to mine.
“That’s the same as mine you muppet. There isn’t any difference.” I said.
“Turn it over, look at what the stylist did.” Lucy responded.
The other side of the page had the same woman, but she looked much more sophisticated. Her hair was just a little shorter than before, but layered, it had been died a dark brown apart from the top few layers. It looked pretty cool. The large photo was inset with the hair in different styles, in a high pony tail, in two plaits - one each side of her head. It looked good, I could easily pull it off.
“Will the wig stand being died, cut, tugged and what ever else?” I asked. Lucy didn’t even bother talking, she just nodded. As the bell rang for the next lesson to start I agreed to go get my hair cut.
English wasn’t anything special, Matt wasn’t there so wearing the little skirt just got me in trouble with the teacher. Never mind.
I went shopping with Charlie and Effy after school, grabbed the clothes that I had seen the previous day and went for a coffee before catching the bus home.
Lucy took me to Tammy’s salon, and showed her the magazine page she had shown me. A couple of hours later and we left the salon. My new hair made me look a lot older, more like I was 20 rather than the just 16 year old that I was pretending to be. I loved the pampering, even if it wasn’t my own hair.
Wednesday flew by, before I knew it I was at home, getting changed ready to meet Matt at the cinema. Lucy was going to drop be in and then pick me up again. As we got into her car she passed me a small pink box with a purple heart on the front of it. It read ‘Vera Wang Princess’.
“You are a princess, so no reason why you should not smell like one”, Lucy said.
“Thank you so much Luce”, I said, as I hugged my big sister. I took the purple heart shaped bottle out of the box and sprayed a little on my neck and arms.
Lucy dropped me off a little way away from the cinema so she didn’t embarrass me, and I walked to the cinema. Matt was waiting outside for me, he saw me coming which was helpful. I had been trying to think of what I would say to him to start a conversation and couldn’t come up with anything.
Matt complimented my new hair, that was the first things he said after “Hey”, we went into the screen and sat just down from the back row. About 10 minutes in he tried the stereotypical arm stretch. I didn’t budge. I ignored it. He gave up. I got really comfortable in his presence though. I hadn’t noticed my own body language, I was leaning towards him by the time we were halfway through the film. He tried the arm stretch again. I turn around and whispered “if you want to cuddle then just ask me! I wouldn’t have agreed to come on this date if I didn’t like you Matt”. I don’t know why I said what I said. Or where it even came from. I don’t think he quite knew how to react. So I lifted the arm rest that was in between us, and leaned into him, he wrapped his arm around my waist and tickled me side. I squirmed and sat around, looking at him. He smiled. He looked so damn cute with a cheeky grin on this face.
I couldn’t resist, I had to see what it was like. I looked down and back up, I wasn’t checking him out, I wanted him to attempt to kiss me. I wasn’t going to give in this time around, I wanted him to have the idea in his head, see how he did after sitting there with his arm around me for a little bit. A further 10 minutes or so into the film I put my hand in his knee. I was running with things that Beth had done on a date with James once. I snapped out of being Jess for a bit, I hope he didn’t notice me pulling my hand off his knee so quickly. I made up for it by linking my fingers with his. That’s when I lent back a little and looked up at him. I was letting instinct take over, the fluttering of my eyelashes worked. He leaned in and kissed me. I went squidgy all over. Matt kissed me. The Matt kissed me! He didn’t know my secret. He couldn’t work it out. I kissed him back and sat up, put my arms around his neck and kissed him a bit more. His hand was on my thigh, I hadn’t noticed to start with, but when it reached my crotch I noticed big time. I pushed him away gently. “Too soon Matt. I’m sorry hun. Just too soon”
It most certainly was not too soon. I would have let him play with every part of me there and then, I was loving it so much. I decided I would try playing with him a little. I moved my left hand from his knee to his groin. I didn’t move my hand, I left it there. I could feel him grow in my palm. I rubbed him a little, not to hard, just a bit of a tease. The film was soon over. He asked if he could walk me home. I said that was fine, but his house was on the way to mine, so we went for a walk around the local park, took a seat and looked up at the stars together.
We kissed a few times, he never tried touching my groin, he didn’t force me to go anywhere near his, but I did anyway. I played more this time, we had nobody near us. It was deadly silent out and I wanted to see what it was like. His cock was so hard by this point I asked him if he knew anywhere more private. I don’t know why. Something was making me want so much more. We walked for about 5 minutes, he jumped over a wall and opened a gate from the inside. He had obviously been here before. I didn’t care. I closed the gate and threw my arms around him, he picked me up and carried me across the private garden and gently put me down. He rolled off of me and held my hand, I rolled over, my hand on his chest, I looked into his eyes and just got lost.
Before I knew it my fingers with pretty painted nails were wrapped around his hard member. I was on auto pilot. I didn’t want things to end anytime soon. He didn’t force me. He didn’t act weird. He just let me go. I let go of his cock, I kissed him again and said “I’ve never done this before” in the softest voice I could manage. He smiled, “you are doing just fine, by all means keep going, I’m enjoying your touch. Stop when ever you want. No pressure at all.”
I stopped for a bit. “People have you wrong, you’re one of the nicest guys I have ever met Matt. You really are a true gent.” I kissed him on the cheek, moved my hand from his chest down to cock again, and started slow again. I’d got the pre-cum on my hand, and I have no idea why, but I couldn’t stop myself from licking it off my hand. I was acting like a total slut. It was if I was personifying what I had wanted Beth to be like, what I saw porn stars being. It didn’t matter, I was in the moment. The taste was different. I’d never tasted anything like it, so I just kept going. I stood up and faced him. At that point I didn’t know if I should pull him up and get him on his feet and go down on my knees or kneel down straddling his legs and go from there. I went for the latter.
I was on my knees, straddling his legs, I put my left hand around his cock, and I moved my head down. As his hard cock touched my lips I opened my mouth just a little and moved my tongue over the head of it. I looked up at him and he was just looking at the stars. I felt so horny at that point.
It wasn't long before Matt came. I got a little on my chin as I pulled off of his now limping penis, but that was fine, I didn't care. I contemplated spitting it out, but decided i’d swallow his load. I lay next to him, we cuddled for a bit before my phone went off. Lucy wanted to know where I was. We made a quick escape, not before making out one last time. He walked me to Lucy’s car, gave me a hug and then kissed me on the cheek before I climb in and left.
“Did he actually kiss you then?”, Lucy gasped.
“Yea. And we made out in the cinema. And...”, I told her.
“I don’t want to know, what happened on your date stays between you and him. He’s cute by the way”, Lucy said, a little smirk on her face.
“I know right? He’s not as much of a jock as he looks. He didn’t ask me to be his girlfriend though”, I said, not realising what I just said.
“James, I love how you are taking this all so seriously and taking lots of steps to make this real for everyone around you, but you do realise that this is just an experiment. It’s going to be over by the end of next week.”, Lucy stopped, her smirk had vanished, she looked serious.
“Who’s James?”, I said, with a confused look on my face. I was just pretending. I knew what I was doing. I did want to see Matt, as Jess, for a bit though. Up until the end of school or maybe the end of the summer. After all, I would be attending sixth form as James, Jess wouldn’t exist then.
“I love you James. Can we spend some time together this weekend”, my phone read, it was a text from Beth. She knew about the date, she was fine with it, I promised that I would do no more than kiss Matt, she was cool with it. The rest of the date would remain secret. I agreed to meet her and told her that I was going to get an early night.
“I would love to see you again Jess. See you in English tomorrow? Matt xx”, a second text came through soon after I had replied to Beth’s message, I didn’t reply to it until I got home. Once home I replied and we ended up texting for quite a while, it was almost 1am by the time I fell asleep.
When I woke up at 7:30am the next morning I had a spring in my step. I was still on cloud nine from the date that I had the previous night. I had a shower, got dressed, chose to stick with the skirt I wore on Monday. In fact, I was pretty much wearing exactly the same as I was on Monday, normal black tights, no pattern and no vest top because I had proper cleavage.
Beth called me when I was on the bus into school, her boss wanted to know if I wanted to have a tryout this weekend. Bang went the time with Beth as James. She gave me his number so I knew who it was when he text me.
English was interesting that day. Matt wasn’t off with me, but he most certainly wasn’t on. For the whole lesson he didn’t really make any form of eye contact. I was devistated. What had I done wrong? Was I too soon with my actions? My mind filled with all sorts. The lesson was over and I left the room alone, ignoring Effy & Charlie. I was quiet for most of the morning.
At lunch Matt turned up to where me and my girls hung out, he hugged me from behind and asked if we could talk. I melted. What was he going to talk about? I agreed and went for a walk with him, we walked to one of the quietest parts of the school, it was so rare to see anyone outside of lessons here.
“I really like you Jess”, Matt said, as he took hold of both of my hands.
We talked for a while, within 5 minutes I had my first boyfriend. We kissed and then walked back to my friends, holding hands. Bex saw me first, I saw her nudge Effy, who was sat next to her and then saw Effy kick Charlie who was opposite her. They all looked at the same time, jaw dropped and then massive smiles.
The rest of the day went by, I had a text from Beth’s boss, his name was Tom by the way. I had agreed to go and say “hello” after school. But Matt wanted to hang out. Naturally I stuck around with Matt for longer than I should have, I caught a bus back home and dropped into the pub when Beth was working. I was still in my school uniform and Tom seemed to take a shine to me sooner than I was expecting. He offered me the job there and then, I asked how much I would be paid and how often pay day came around. I was asked to start on Saturday lunch.
“Wear either black trousers or a skirt and tights on Saturday. Wear a black top, You can grab a work shirt when you get here.” He told me, before I left.
I was about to embark on a whole summer of being Jess. Something that I wasn’t planning, but getting a job as Jess was a hell of a lot easier than it was when I was James. I had tried, nobody wanted a geeky waiter.
Matt text me all night, I was gutted about not being in the same town as him. We sexted a little, but I fell asleep early that night.
Thursday was a boring day in school, nothing much happened, Matt hung around with me and the girls at lunch, but that was about it. I had arranged to have Lucy pick me up from Matt’s house after school so I could spend more time with him.
Matt and I had the house to ourselves. I’m not going to go into too much detail, but he found out my secret. It was a mistake. He didn’t over react at all really. He wasn’t upset, or angry.
"I asked you out on a date because of the way you make me feel. Because of the way you are. You are the girl that every guy wants to be with and every girl wants to be like. I was never in a million years expecting you to not be 100% female. You had me fooled. But I wasn't going to stop you, I wanted to see what you were like. What you wanted to do. Your touch has made me feel happier than I ever have before. And that's all after I found out about your secret.", he said, blushing.
“You’re cool with this?”, I asked him, my hand on his chest.
“Yea, totally”, he hesitated, “I can’t say that I will be playing with your cock. But I enjoy your company as my girlfriend. I’m going to find it difficult to adjust, I think. But yea, I’m cool with it”. He smiled, we kissed, and lay on his bed watching TV.
Over the next half hour we messed around. We kissed. But that was all.
Lucy picked me up, and I told her about his reaction to finding out my secret. She didn’t respond, she changed the subject.
Friday was mostly good. Matt was a nice guy, he didn’t tell anyone my secret. He did ask to go out on Saturday night, I agreed, forgetting about my promise to Beth. I was on the phone to Beth about Matt asking to spend time with me on Saturday that even, she suggested that all 3 of us went out together. I was hesitant. I called Matt and explained to him, he got angry and hung up the phone. I left him alone and called Beth back. She laughed and reassured that I would get a text from him in no time at all.
She was right, about 30 minutes later I got a text from him, “I’m sorry Jess, I’m just confused. wouldn’t it be weird?”, it read. I called him, reassured him that it wouldn’t be a problem. We made plans for all 3 of us to spend some time together. I would be Jess, James would not make an appearance.