Day 2 – Jenny Goes Shopping

This is a sequel to Ditzy Jenny gets a boyfriend

The next day was Sunday; I woke up feeling really excited thinking about what had happened on my date yesterday with Jonny. I was hoping that he was going to ring me or text me and say he wanted to take me out again tonight but I was worrying about what I could wear.

Stephen my twin brother knocked on my bedroom door and came in my room, I was still lying in bed but luckily I’d got some pyjama’s on. They were silky ones, sort of blouse and shorts although now I was starting to grow, I’m 14 now, both the top and shorts were way too tight.

“Hey Jenny, how did your date go last night?”

“It was great Stephen”, I was sitting up smiling at him.

“I bet he had a great time sucking on those nipples Jenny”, I looked down, my nipples were really sticking out through my pyjama top, I tried squashing them back down a bit but that only seemed to make it worse.

“Well, did he fuck you Jenny?”, Stephen said laughing as he bounced onto the bed

I shook my head, “He said he’s going to call me and take me out again” I said all excited “But what am I going to wear, I can’t wear Grace’s dress again.

“Why don’t you ask dad to give you some money to buy some new clothes, you really need something sexy if you’re going to impress him?”

“Do you think he will, what should I buy Stephen?”

“Hang on Jenny, I’ll go and ask dad for you”, I stayed in bed wondering what dad would say while I waited for Stephen to come back. I thought about buying something with my own money but I never had any of my own money left as I always just spent it if anyone gave me any.

Stephen came back in my room after a couple of minutes; he had brought my dad upstairs with him. They both came over and sat on the edge of my bed.

“Morning Jenny, Stephen tells me you need to buy some new clothes to impress this new boyfriend of yours. You are getting a big girl these days, that top you’re wearing looks like it’s getting way to small for you”. They both seemed to be starting at my boobs, I guess they couldn’t help it the way my nipples were poking out through the tight material. They always seemed to do that when I was wearing a silky top, but I really liked the feel of it against my skin. “OK but you better take Stephen shopping with you” my dad said “he’s a lot more sensible with money than you are Jenny”

“Thanks dad”, I was really pleased to have Stephen with me anyway, he would know what clothes I should buy and I was no good at counting the money.

When they’d gone out of my room I got up and got dressed, I put the t-shirt and jeans I’d been wearing earlier yesterday back on again. They were both too tight for me now, especially the jeans. I looked at my bum in them, the seam went right up my arse, you could even see were it went up my pussy they were so tight, I hoped Stephen didn’t mind going out with me looking like this. You could see the line where my knickers were on my bum cheeks so I thought I’d better leave my knickers off again.

I went on the bus into town with Stephen, he was telling me what he thought I should buy, my dad had given him £100 to spend on me. “If we go somewhere fairly cheap Jenny, we can get quite a lot of stuff with this”

“OK Stephen”, I just wanted to look good for Jonny

He said I should try and get a couple of short skirts and maybe some stretchy leggings or tight jeans and a couple of t-shirts”

“You’ve got a really nice arse Jenny” he said “so you should try and make the most of it, you look really good in those jeans”. I just blushed; Stephen is so nice to me.

When we got off the bus I followed Stephen towards the shops, “First we better get you some new underwear, what size are you?”

“I’m not sure Stephen” my mum usually bought that sort of thing for me.

“OK, if we go to a department store first they will measure you up. Then we can go somewhere cheaper and get something a bit sexier”

Stephen took me into an expensive looking department store; he said we needed the lingerie department. He found a shop assistant and asked her if she would measure me up as I needed some new underwear. The lady smiled at my brother and at me. “Sure thing” she said. She seemed very nice and very pretty, I was sure my bother would fancy her. She was about 18 or 19, she had lovely shoulder length light blonde hair, not like my brown hair. And she had quite big boobs, bigger than mine; they really looked good in her cream blouse. You could see her bra a bit; I bet they get to chose really nice underwear working here.

“Come with me love” she said, “your boyfriend can come as well, then he can tell me what sort of underwear he likes”, she was grinning at him but he never said he was my brother not my boyfriend so we all ended up in the small changing cubicle together.

“Put your arms up” she said to me “and I’ll take that top off for you”. I put my arms up and she lifted it over my head so I was standing there in a bra and jeans. Stephen was stood watching my boobs, it was so small in there we were all stood really close together. “This old bra looks a bit small for you, let me take it off” she quickly spun me round and unclipped my bra taking is off me. Then she spun me back round again to face her and Stephen.

“See it is too small for you, it’s left all these red marks, let me try and get rid off these for you”. She put some cream onto her hands and started massaging it into my boobs quite firmly, it felt really nice and the red lines started to disappear, she was really kind telling me they were lovely and soft.

She took out her tape measure and started measuring me up, she measured me round my chest, and then she measured each boob on its own. The she tweaked each of my nipples and measured how big they were, I don’t know why she bothered tweaking them as they were already really sticking out but it felt really nice.

“34 C she said, I thought that other bra you had on was too small”, then she looked at Stephen, “what sort of bra do you like?”

“Something sexy” he said grinning

“I would go for something quite thin, not too padded as she has quite big breasts for her body shape and she has lovely big nipples. If you get her to wear tight t-shirts with a nice silky bra her nipples will really stand out, she’d look great” She said she would get a couple for me to try on, before she disappeared she said to Stephen. “Hold out your hands”, she squeezed some more cream into the palms of his hands. “Keep rubbing that into her boobs while I’m gone to make those red marks disappear”. When she’d gone out of the cubicle Stephen told me to stand back against the wall and put my hands behind my back so that it would push my boobs out and make it easier for him. I did what he said and that really seemed to work. He did a really good job rubbing the cream in and he kept going until the lady came back. I don’t think he had any cream left on his hands by then but it felt really nice with my brother rubbing my boobs I didn’t say anything so that he wouldn’t stop.

When she came back in she got me to try on a bra, she adjusted it for me so it fitted right then helped me put my t-shirt back on. She showed Stephen how my nipples stood out. He seemed to like it as I could see a big bulge in his jeans but maybe it was the shop lady he fancied.

“Do you want her to try some matching knickers on?” she said to Stephen.

“Sure” he said. She took her tape measure and measured my waist and hips, then she measured my inside leg. I don’t know why she needed to know that but it felt really nice when she pressed her thumb right up against me. She measured both legs, she said she would check they were both the same length. After that she disappeared again and came back with some matching white knickers.

“I think these would look best on her” she said showing Stephen a tiny white silky thong “shall we try them on?” Stephen nodded.

“OK, do you need a hand getting these jeans off?” she didn’t wait for a reply, she just started unzipping the jeans then she squatted down in front of me and pulled them down. It was then I remembered I wasn’t wearing any knickers.

“Oops sorry, I’ve pulled you knickers down” she said

“No, it’s ok I didn’t have any on” I blushed

“You’re getting quire hairy down there” she said to me, you might need to get your boyfriend to give you a tidy up. I didn’t know what she meant but she helped me out of the jeans and into the tiny white thong. She pulled them up tight; they were nice and silky and felt nice on my skin. They fit really good she said to Stephen, she spun me round so they could see my bum then spun me round again so I was facing them. Looking at Stephen she said “These are real silk, see how soft if feels” she stroked the front of my knickers. Then Stephen felt how soft they were as well, he ran his fingers right down the front of the knickers and kept going over my pussy and practically to my bum hole. He stroked them backwards and forwards a few times saying they felt really nice and soft. It was feeling really nice for me as well, I was sorry when I had to take them off and put my jeans back on.

The lady gave the underwear to Stephen and told him to pay at the till. “Fuck that” he said, to me as we came out of the changing room “this shit is way too expensive in here, we know your size now so we can go and buy you some cheap stuff”. Stephen was so clever I would never have thought of doing that.

We left the department store and when into another shop that was a lot cheaper, there were clothes all over the place.

“OK Jenny lets try and find you some skirts and leggings first”. He picked out some clothes for me and we went over to the changing rooms.

“Do you mind coming in with me Stephen, I’m rubbish at getting stuff back on the hanger?”

“OK Jenny, as long as you tell me what happened on your date last night.”

We went into the changing room cubicle together, it was even smaller in this shop, Stephen sat down on the little bench while I tried to get my jeans off, it was hard because they were so tight and there wasn’t much room.

“Just stand there facing the wall Jenny, and I’ll pull then down”, Stephen was still sat on the bench while he pulled down my tight jeans, I remembered again I didn’t have and knickers on. My bum was level with his face as he pulled them down, I couldn’t help pressing my bum against him as he yanked them down. He accidently pushed his nose right up against my bum hole, I hope it wasn’t too smelly!

Whilst I was getting the clothes on and off I told Stephen about giving Jonny a blow job in the car on my way home last night. I said how I’d sucked and licked Jonny’s cock for him.

“Do you think I was doing it OK Stephen?”, I was worried in case I was doing it all wrong

“I’m not sure Jenny, maybe you should show me how you did it”.

“Are you sure you wouldn’t mind Stephen” He said it was OK which was really kind because he wouldn’t really want his sister doing that to him. It was a really tight squeeze in the cubicle but he opened up his jeans and I managed to squat down in front of him and get his cock in my mouth. It wasn’t quite as big as Jonny’s but it still seemed pretty big. I had one of the mini skirts on at the time, Stephen said I should take it off so I didn’t get any cum on it. He must have been able to see my big bum in the changing room mirror as I practised sucking his cock for him. I hope he didn’t mind too much.

I sucked hard on his cock going up and down, he helped me by holding my head and guiding me back and forwards showing me how fast I should go. After a few minutes he started pushing back and forward really hard in my mouth, his stuff exploded into me and seemed to go straight down my throat. I was getting good at keeping all the cum in my mouth now. After I’d cleaned him up I asked him how I had done.

“That was pretty good Jenny, but you need to learn how to deep throat”, I didn’t know what he meant but he said he’d maybe show me later. “You can use me to practice on if you want Jenny, and maybe Billy too”. Billy was our pet Labrador, I wasn’t sure about practising on him but I just smiled because Stephen was taking such good care of me.

When we got back home mum was making diner for us. So I took my new clothes upstairs to my room. I laid them on my bed looking at them. My dad came in my room

“Hi Jenny, how did you get on today, did you spend all my money?” he was smiling at me

“I’m not sure dad”, I had no idea how much we had spent, I’d just left all that to Stephen.

“Are you going to try on your new clothes for me?”

“Sure dad” I was pleased he wanted to see me wearing my new outfits, for once I remembered I didn’t have any knickers on. “Shall I try on my new undies first?”

Dad seemed to like this idea, OK I’ll turn around whilst you put them on.

I quickly slipped out of my jeans and t-shirt and put on a bra and panties that we’d bought in the cheap clothes shop.

“You can turn round now dad”, I stood there proudly in my new underwear.

“Wow Jenny you look amazing”, the underwear I’d put on was similar to the ones I’d tried on in the department store only miles cheaper. The bra was silky white and felt really good, they didn’t quite cover all of my nipples but nearly did. I guessed they were saving money on the material. The panties were a matching white silky thong. They were a little bit see through, I could just make out my dark pubes a bit when I looked at myself in my mirror.

“Turn round Jenny, lets have a look form behind”, I turned around so he could see me from behind.

The thong disappeared up my bum crack, I was really enjoying the feeling while my dad was standing there looking at me. My dad had me try on all my different outfits, I loved putting them on and taking them off in front of him, especially when I could see the big bulge in the front of his trousers, that made me feel really good. I just wished I could see him without his trousers on.

Then my mobile bleeped, it was a text of Jonny. He said he really liked me but he really preferred blondes. I was really upset, but my dad said I shouldn’t worry “You could easily die your hair blonde Jenny, you’d look even more amazing, you could even be a model”

This cheered me up a little, “do you really think so dad?”

“Sure Jenny, I’ll help you bleach your hair tomorrow, and if you’d like I could even take some pictures of you with your new hair and your new outfits, would you like that”

“Yes dad I really would, could we do that tomorrow?”

“