Introduction:
The weekend before Kelly and I were due to return to school she announced she needed some new clothes. Kelly had grown over the summer and most of her school uniform didn’t fit her anymore (well not decently, anyway!). So, on Saturday morning Mum packed us both into the car for the trip into town. I needed some new things as well so it wasn’t too bad.
As we were walking around the shops Mum mentioned she too needed to pick up one or two things, in the underwear department. I was alittle embarrassed wandering around the racks of thongs, suspender belts and panties. I don’t know why I was nervious, after all I’d seen Mum with a whole lot less on than these skimpy clothes. But then it struck me, I was getting turned on! I felt a tingle in the base of my cock and the unmistakable wetness oozing from the tip of my dick confirmed my suspicions.
Kelly was sat by the changing room door, waiting for Mum,who was trying on a range of provocative undies. I’m not quite sure why as she hardly ever wore clothes at home, but I suppose she needed them for when she and Dad went out. The feeling in my cock intensified and I had to move. I walked around a display stand of thongs so that I was hidden from view, or so I thought! Quickly, I grapped my cock through my trousers and began rubbing the amterial up and down the shaft.
“What you doing?” asked Kelly. She’d seem me move and had followed me.
“Er…Kelly, don’t tell Mum will you”
“Why? It’s not as if she doesn’t know you wank off, she even helps you!”
“I know, but in public is different, you know what she’s said”
“Anyway, why do you need a wank right now?”
“All these clothes, the thought of Mum or you in them, just got me excited, that’s all”
A mischevious grin spread across Kelly’s face.
“Or you”
“What?”
“I bet you’d love to feel the soft silkiness of these panties pressing hard around your cock. Holding your balls in place. These sheer thrill of pulling silk stockings over your freshly shaved legs and the feel of a thongs pulled up tight under your arse!”
“Stop it Kelly, you’ll make me come…ah too late!”
And I shot a wad of cum into my boxers. Quickly I felt the warm wetness spread and begin to trickle down my right leg.
Just then, Mum pulled back the curtain of the changing room, a slightly flushed expression on her face.
“Are you okay Mum”, asked Kelly
“Yes, fine, just a little warm, that’s all”.
Mum paid for her purchases and just as we were leaving, she said she’d forgotten to look at something.
“Kelly, will you come back in with me, I want your opinion. Steve, you wait here we won’t be long”.
I had to turn my back to the street and look in the window as my jeans were showing a radiply expanding wet patch. Sure enough Kelly and Mum weren’t long and we were soon on our way home.
Later that afternoon, Kelly and I were out in the garden, when Mum called to me.
“Steve, can you come inside a few minutes, I’ve got something for you”
“Mum, where are you?” I called as I entered the house.
“Upstairs”
As I climbed the stairs I could see she was in my room. Pushing the door open I got a huge surprise! There, laid out on the bed, was a sheer black thong, silk stockings and a suspender belt. All topped off with a lacy bra.
“Steve, I overheard you this morning in the shop. That’s why I was a little flushed, I’d had a quick wank too at the thought of you wearing these! Kelly, told me, when we went back in, which set she thought you’d like. I hope she got it right?”
“Ye, she did” I didn’t know what else to say. “Isn’t is a little weird, a boy dressing in womens underwear?”
“Why? It’s no more weird than a brother and sister fucking eachother and the rest of the family too”
“I suppose not”. My mouth was dry with anticipation but my cock was making up for the moisture.
“Look,” Mum said “I’ll leave you to it. Try them on and let’s have a look at you. Call us when you’re ready”.
Oh my God! Kelly was absolutely right the feeling of silk against my shaven legs and cock was out of this world. First, I slipped my right foot into a stocking and slowly rolled it up, revelling in ever seconds worth of sensation. I repeated the process with my left leg, before wrapping the suspender belt around my waist and attaching the fasteners.
Next it was the thong, and as the material stretched across my cock, it spasmed and sent out a squirt of pre-cum juice soaking the silk. It all felt so natural and right. At last I felt a completeness I didn’t know I was missing.
I just stood there looking the mirror, admiring how I looked. I was slender and the lingerie fitted me perfectly. My shaved state helped my look like a teenage girl and I felt fantastic. After a few moments I called Mum and Kelly, for them to come and see how I looked. When Mum saw me, her hand shot between her legs and she began playing with her clit.
“Wow, Steve, you look great! Kelly, you were right, the outfit is perfect! How does it feel?”
“It feels right somehow. It’s like a dream come true…”
“Oh wait until Dad gets home. He’s going to love this. You know, he dresses in my underwear all the time. Every day, when he goes out, he’ll be wearing one of my thongs. That’s why I buy so many! We have to specially adapt them because of the size of his cock, but that’s part of the pleasure!”
“Can I wear these all the time?”
“Of course, but just remember, when you’re back at school, only wear them on days you don’t have sport, other wise, the other boys will find out!”
“Okay Mum, thank you”.
The holidays soon came to an end and it was time for Kelly and I to return to school. After the excitement of the Summer, the prospect of a boring routine didn’y inspire either of us. I was excited however, as I was wearing under my uniform a brand new pair of lacy high leg panties.
Living in the small rural village like ours meant that we were the first stop for the school bus, which gave us about 15 minutes alone before any one else got on.
“How do they feel?” asked Kelly as we took our seats on the bus.
“Great. What are you wearing?”
“I’m not!” she replied. And with that she lifted up her skirt to reveal her hairless cunt.
“Kelly! What if some one sees?”
“Then they’ll be the lucky one won’t they? Anyway, I’ve decided I’m not wearing underwear again. Why hide this?” she said glancing down at her pussy. And I had to agree with her, why indeed.
I sat in silence, just imaging the comments from my school friend if they knew that Kelly had decided to go without underwear and instead I was wearing it!
Our next major sexual adventure didn’t take place until the following Easter holiday, when Grandma and Grandad, took the whole family on holiday to France. It was a holiday that neither Kelly or I would ever forget!

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