This is the second part of my true story of how I started dressing and became Jason's girlfriend. This is just our first shopping trip, but it is also the first time I went out in public as Susan.
Jason and me - part 2
Where Jason and I go shopping for the first time.
The next day I almost didn't go into school as I felt embarrassed, nervous and just a bit weird about what had happened with Jason. However, I summoned up my courage and breezed in as much as normal as I could. I didn't bump into Jason until late morning when we shared a class. He was absolutely normal until we went into the class, he let me go first and gently placed his hand on my ass as we went through the door. I'm sure no one noticed but I blushed bright red, although it was so nice that Jason felt that way about me, I'd been afraid that he'd regret everything in the light of day.
We didn't get a chance to chat alone until later that afternoon when we were pretty much alone in the sixth form common room. I was already there and Jason came in, said hi, and asked me if I wanted a coffee. He brought the coffees over and sat looking at his cup.
"I really enjoyed last night" he whispered
"Me too." I replied, "Although I can't really believe what happened."
"Do you want to go shopping Saturday for some clothes, like we said?"
I was a bit surprised by this suggestion. "Where were you thinking of?"
"Oh" said Jason "I thought we could cruise some of the charity shops, they have loads of stuff in them, clothes, nice dresses, stuff like that, my sister uses them a lot and I think they're quite cheap."
"Yeah, ok, sounds cool." I wasn't quite sure what we'd find at the kind of money we had, probably really drab old stuff that smelled awful, but in principal I liked the idea of shopping with Jason.
Saturday came and we were out in town by mid morning. We stopped in the first shop we found, an Oxfam shop, and started mooching around the rails of dresses. I was surprised that there were some really pretty dresses, skirts and blouses, but also realised that I wasn't quite sure what size I was. I asked Jason what size his sister was, as her stuff fitted me fairly well, and then one of the ladies working there asked if she could help us at all.
I just went dumb, but Jason said he was looking for something for his sister but wasn't sure what size she was.
"She's about 5' 4" and slim without being too skinny" then he added "and sort of flat chested if you know what I mean."
"Mmmm" said the woman, who was quite old "could be a 10 or 12, but might just be an 8. You really ought to check it out first to be certain."
Just at that point two girls from our year at school came in and smiled at Jason, they ignored me. We both realised we were getting out of our depth and I just said "We'll check and come back later" and practically dragged Jason out of the shop.
"They'll guess why we were in there." I blurted out.
"Cool down" said Jason slowly "They have no idea, there's no way they can guess."
"I can't go back in there, I was too nervous we'd get caught."
Then Jason came up with the simplest solution.
"I can borrow my mum's car this afternoon and we'll drive to a shopping area where no one knows us, and before we go I'll check out Claire's dress size. It'll be cool, ok?"
I thought about it and although my knees were still shaking with nerves I was also so excited that nodded my assent. Jason wasn't looking at me at that moment and repeated his question.
"Is that ok? If we go somewhere that we won't be spotted?"
I nodded again and smiled, this time Jason was looking at me and I could see he was thinking about something. Then he came up with the bombshell.
"You could go as my girlfriend" he said confidently, "not in a dress and that, but if you wear some nice jeans, one of Claire's tops and brush your hair like you did the other night, you'd easily pass for my girlfriend. Then it wouldn't look odd if we were shopping together."
"Yeah, that's going to work really well when someone hears my nice soft girl's voice." I mumbled sarcastically, not really taking the idea seriously.
"No, it'll be ok," said Jason "I'll talk for you, tell people that you've got a sore throat, you just have to look pretty - and I know you're good at that."
I smiled at Jason, he was so nice to me, and although I was terrified about the whole idea I was also excited at the prospect of being out with Jason as his girlfriend.
"You need a name though, do you have one you'd like?"
I'd already thought about this and said "Susan, I'd like to be Susan, or even just Su."
"That's a cute name, I like that Susan."
I giggled and Jason bumped me gently on the shoulder laughing at the same time.
"Hi Su" he said and we both laughed again.
We went back to his house where his Mum was about to go out and do some shopping before going to work. She's an agency nurse and works all sorts of shifts.
"Hi mum, is Claire in?" he asked in a breezy tone.
"No dear" his Mum replied "she's gone to Aunt Penny's and won't be back until Wednesday."
"Oh ok. Is it alright if I borrow the car this afternoon, we want to go over to Maidstone and check out some shops there?"
His mum agreed after telling him to drive carefully and added all that stuff that Mums always list every time you go anywhere. We settled into the kitchen and made a coffee while his Mum got ready to leave. She said she'd leave something for supper for him before she went to work.
When she finally went Jason and I went up to Claire's room and found a nice pink T-shirt with little stars all over the front and I just about struggled into a pair of her jeans. They were incredibly tight and there was no chance of me getting an erection, there just wasn't room. Jason said my ass looked great in tight jeans and wiggled it at him.
"If you do that again we'll not be going anywhere." he said, then paused for a moment, "The T-shirt will be fine" he said "we can run an iron over it when we get back and Claire will never know it's been used. But I think you ought to wear a bra too, if that's ok with you?"
It was more than ok but I pointed out that I wasn't going to leave the house like that in case one of his neighbours spotted me as half boy half girl. I hadn't met any of them but it would have felt weird and they'd be bound to tell his mum.
"That's cool" he said "you can change when we get out of the area, we'll just take everything you need in a carrier bag."
It seemed so simple and I didn't think much about what was coming. We borrowed a hairbrush, perfume, lipstick, some eye shadow, Claire's T-shirt and a bra which already had some padding in the cups (Claire was quite small chested). In the drawer with the bra we also found some extra bra pads and took a couple of those. We collected the ear rings I'd had on before and some bangles and rings from his mothers costume jewellery. Then I suddenly realised I needed shoes. I knew I couldn't walk in heels and Claire's shoes were just a little too tight for me. Then I spotted some flat slip on shoes with no backs, they were pink and had little bows on the front. I quickly tried one on, then popped them both in the carrier bag.
Then we were ready to go. While Jason locked up the house I got in the passenger seat waiting for him. I already felt like his girlfriend and couldn't wait to change into Claire's top. We set off and Jason said he knew just the place to stop on route. We could go to the motorway service station as he said only people passing through went there and we wouldn't bump into anyone we knew. It sound like a plan and I agreed.
On the way there we hardly spoke. We had music on the radio I was feeling so good. Then we arrived at the service station, pulled off the road and went into the restaurant area.
Jason said he had an idea. The toilettes had a sort of lobby and he said we could wait until we were pretty sure no one was in the ladies and I could shoot in there and change in a cubicle while he loitered in the lobby area. It was simple and effective, but we hadn't planned for someone coming in while I was there. I'd changed, not using the pads in the bra as they didn't look right, instead i put some tissues in the cups which looked ok. I'd brushed my hair and put on my bangles etc and I was just putting lipstick on in the mirror when a woman came in, she mumbled something to me and dived into a cubicle. I wasn't going to be there when she came out so skipped the eye shadow.
Jason was nervous when I appeared and we quickly made our way back to the car where I checked my look in the car mirror.
I was a bit disappointed, but Jason just said "You look so pretty Susan"
I said I wanted to try some eye shadow but Jason said I looked ok without. I wasn't sure I could get it right anyway so agreed to go with just the lipstick. I settled back in the seat and felt great. The bra made me feel like a real girl, just something about the sensation of the straps over my shoulders and, of course, the sight of my small tits. I could feel I was getting hard but nothing showed through the jeans. I then realised that I still had my trainers on. I quickly dumped them and my socks in back seat and slipped the shoes on we'd borrowed from Claire. They looked really pretty and I felt totally like a girl at that point.
As we drove into town and into the multi storey parking below the mall, Jason turned to me and said "I've just thought of a surprise for you."
"What's that?" I asked, wondering what he'd thought of.
"I'm not telling you, but just come with me and you'll see."
As we left the car park Jason took my hand in his and It felt so good, just like we were a couple. He leant over to me and whispered in my ear.
"Just remember two things." he said "You've lost your voice, and you already look just like a girl."
We wound our way to a large department store and Jason led me to the make-up department and walked me straight up to one of the girls who did demonstrations for people who wanted a cosmetic make-over.
"Hi there" he said confidently "It's my girlfriend's birthday, she's lost her voice and I know she wanted to try some different eye make-up so I wondered if you could advise us, or rather her."
I couldn't believe the nerve of Jason and just stood there terrified. The girl was looking at me carefully but spoke to Jason.
"I'm sure we can help, just leave us to it for 10 or 15 minutes. What's your girlfriend's name then?"
"Um, Susan, but I thought I'd stay and watch if that's ok"
"No I don't think that's necessary, just leave us girls alone and we'll get on fine. Now go and have a coffee in the restaurant and come back in about 20 minutes."
Jason and I looked at each other and he shrugged and smiled at me, then kissed me on the cheek and said "See you in a bit then."
I was sure I was going to get into trouble and that someone was going to call the store manager and have us thrown out, but the girl took my hand and told me to sit on a high stool by the make-up counter. Then she leant forward and spoke quietly so that no one else around would hear.
"I have a brother who you'd like I think. Just as friends of course."
I raised my eyebrows questioningly and as she brushed my hair back from my forehead and put a band around my hair to keep it back from my face. She took a tissue which was slightly moist and started to take off my lipstick. As she was doing this she continued talking quietly.
"My brother likes wearing make-up too."
I stiffened up, and was terrified what she was going to say but she held my hand and smiled, which made me feel a bit safer.
"You're much prettier than him though, we're not going to have to do anywhere near as much for you to make you into an extremely pretty girl. By the way, my name's Julie, and if you want to ask any questions just whisper quietly and no one will know. The quieter you speak and the more you speak at the front of your mouth, rather than from your throat, the more like a girl you'll sound."
I wasn't really surprised that she knew I was a boy, but I couldn't believe that she was ok with it. As she started on my make-up she told me what she was doing and started with a simple foundation because she said I had normal skin which wasn't too dry or too oily. Until then I'd had no idea what kind of skin I had, except that I only got the occasional spot which would always clear up quickly. She spent the next 15 minutes or so going through a whole range of products and advice. I followed it all in series of mirrors on the counter. It was fabulous when she started doing my eyes as I had completely relaxed by this stage. Although she had seemed to be doing a lot, the makeup on my face was very light and it hardly looked much different, just sort of smoother and cleaner, but the eye makeup made an enormous difference, she made them quite dark and explained that it would make dark brown eyes like mine look even bigger. She outlined my lips and painted lipstick on with a brush. All this was new to me and I realised that I would struggle to do as well as her. I said this to her and she just said that if I practiced and made sure not to overdo anything that I'd get there quite quickly enough.
Jason re-appeared just as she was finishing and just stood there almost open mouthed. Julie turned to him and smiled.
"How do think your girlfriend looks now?"
Jason just came up with one word "Wow"
While he stared at me I got off the stool and Julie was putting samples in a small bag for me. She put her arm round my waist and said "Now just remember to keep it all light and come back and see me when you're next in town." Then she kissed me on the cheek and pushed me gently towards Jason.
I took Jason's hand and said quietly "Can we go shopping now Jason."
He gulped and turned towards Julie but was dumbstruck. I smiled at Julie, mouthed a thank you to her again, and led Jason out of the store.
When we got outside he put his arm round my waist and kissed my forehead.
"You look so pretty Susan. I thought you looked good before but any guy would fancy you like mad now"
"Good job you got me first then." I replied.
We walked round the town and I had fantastic fun in the charity shops and bought two dresses, a denim skirt, two very pretty tops and even a pair of high heeled shoes. We also found some pretty beads and bangles which I couldn't resist. After that we went back to the department store as I wanted to get some underwear of my own and Jason said he'd buy it or me. He was quite nervous in the store but by this time I was pretty confident and selected a matching set of white bra and panties with lacy pink trimming and two pairs of hold-ups, one almost white and the other beige.
I was having a fantastic time and Jason was being so sweet. We went and had a coffee and I even caught sight of a guy at another table eyeing me up. I guess it was this that made me realise how nice it was to be a girl and have boys look at you like that, if I hadn't been with Jason I would have been such an easy pick-up.
Jason rang his mum on his mobile and she said she'd left some fresh pasta and that it would be enough for me if I wanted to stay. She was going to be working a late double shift and Jason said that meant she'd be going to work at about 4pm and wouldn't be back until about 9am the next morning. He asked me if I wanted to go back and try on what I'd bought while he cooked the pasta - a rather grand term for boiling it in water.
I wasn't going to say no, I was desperate to try on my purchases and see how I looked. So we headed back for the car arm in arm as girlfriend and boyfriend.
tbc