I wasn’t exactly what you’d call the most popular kid in school but I got through the day. I hung around with a couple of friends at lunch, all girls but this one boy called Josh, he liked hanging with the girls cus he loved fashion. He bordered on being emo, with his black straightened hair finishing a little above his shoulders; he was thin, slightly muscular, 5ft 12 inches and the same age as me 15. We were best friends and I’d regularly go round his house for sleepovers, play computer games and all that kind of stuff. I liked him but would never admit it. Me, I was blonde haired, 5ft 11, normal sized and 15.
My fashion sense was terrible, id wear my uniform at school and then when i got home just shorts and a t-shirt, I’d go out wearing the same.
This led to on one Friday me and Josh were in Maths, sitting next to each other as usual, he asked me if I’d like to go into town on Saturday where he could give me some fashion advice and I could buy some clothes that were actually socially acceptable.
So Saturday came around and I put on my usual, long shorts and a what I thought was a smart t-shirt, picked up my money that I’d got out of the bank the previous day, I reckoned £180 would be plenty to get a some new stuff. I walked round to Josh’s house at about 11am because his mom was giving us a lift into the town centre. He was his usual self, smartly dressed in nearly skinny jeans hanging so you could just see his underwear – I loved this - t shirt and a loose red and black striped/chequered shirt over the top.
We arrived in town, Next to be precise, that’s where he said it was best to go for all the stuff that I needed. We walked in and followed the signs up the escalators to the boys/mens section of the shop, I had never been in here before and there were so many racks I didn’t know where to start but Josh helped me. Like he knew where everything was he walked around picking up jeans, polo shirts, shirts and smart t shirts for me. I was shocked at how quickly he had got all this and as soon as i knew it he was leading me to the changing rooms on the other side of the store. He walked in, briefly saying hello to the attendant that was standing in front of the changing rooms – presumably to stop anyone wearing stuff that they’d taken in. In this area where about 7 or 8 little rooms with proper wooden doors on each with a small lock saying either occupied or vacant, the room at the end of the small corridor was open so I went inside and strangely Josh followed me in. He suggested it would be easier for him to see if I looked okay in the clothes if he was in with me, there was plenty of room so I didn’t mind, seeing as we changed together for gym at school anyway.
He sat on the little chair in the corner and told me what combination of clothes to try on first so I did, took my current clothes off and just as I was about to put my new jeans on, he stopped me, I was standing there in my boxers looking at him and he had a confused look on his face and asked; “You wear those boxers?”
“Yeah” I replied awkwardly.
“Hmm, you really need some new underwear, when we go out after trying these on we’ll pick up some boxer briefs, there much better and maybe some y-fronts as well”.
“Okay then”, now with a smile on my face.
I tried on the rest of the clothes and Josh picked out the ones that I should buy.
As we walked out of the changing rooms Josh handed the assistant the clothes we didn’t want and he walked – quite sexily may I say – towards the underwear rack which wasn’t so far away.
He picked out some age 14 boxer briefs and showed me them, “They’re not my size” I said. n
“They’re better tighter, I wear them this size as well”.
I wasn’t going to argue with him as clearly he knew his stuff.
He gathered some brightly coloured and patterned ones and put them into the shopping basket. Like he was slightly embarrassed he also put some same sized y-fronts into the basket quickly.
We got home about and an hour later and it was now about 5pm, he asked if I wanted to stay over the night, so of course I didn’t say no.
We did the usual, watch television and play on the computer until about 11pm and we went up to his room. Just like the previous times I’d slept over his double bed was made, two separate covers one for each of us already set up.
He suggested that I should try on the underwear we’d brought earlier just to make sure that they fit and we didn’t have to take them back to the shop, so I got them out of my bag and headed towards the door to go to the bathroom.
“Where you going?” he asked.
“To the bathroom to try these on”, I replied quickly.
“Whats the point, just try them on in here, less hassle that way. Oh and lock my door so that no one walks in.”
Nervously I took off my trousers and my current boxers and tried on one pair of the boxer briefs, hey fitted well, much more comfortable than I had thought, I really liked them. I took them off and put on the new y-fronts.
“Wow, you look sexy in them” Josh said as soon as I had them on.
“Erm, thanks” I replied nervously.
“Why don’t you come over here so I can check they aren’t too tight on you.”
Without hesitating I walked towards him and as soon as I was close enough he pulled me in and he kissed me, he wouldn’t stop but I enjoyed it, I enjoyed it a lot. We started kissing passionately, throwing our tongues in and out of each other mouths, touching every corner of our mouths.
He stopped and moved away from me, “What are you doing?” I asked curiously.
He slowly took off his shirt and jeans, so sexily that my cock was rock hard at its full 8 inches now. Wow, he was wearing y-fronts too; he looked incredible in them, shaping him so perfectly.
He noticed my raging hard on underneath my underwear and he gestured for me to take them off. At the same time he whipped off his and we were both standing naked in front of each other. This was something I had only dreamed off, it was happening!
We read each other’s minds and again started to make out, it wasn’t my first but it as most defiantly my best kiss ever. I reached my hand down to his cock, 7.5 inches I’d say, smaller than mine but i didn’t care, it was his cock!!
He stopped us again and began making his way down my chest, stopping at my nipples to suck on them briefly before continuing down. As he reached my cock I shuddered as he placed his hand over my cock and began jerking me off, wow it felt amazing, doing it myself was great but this, it had no limits. As if nothing could be better he wrapped his mouth around my head and started to like m cum hole. I groaned and moaned until I burst 6 shots of cum into his mouth, he obviously wasn’t experienced as he struggled to swallow it all and some seeped from the edges of his mouth back onto my cock.
It was my turn now; I wanted his cock so I immediately sprang down and engulfed his manhood into my willing mouth, it was so warm and soft! Before i knew it he shot 6 maybe 7 loads down my throat, I’d tried my hardest to swallow as much as possible but I wasn’t great at it and some spilled onto the carpet.
Without a word Josh lay down on the double bed lifted his legs and pointed briefly to his hole, I knew what he wanted me to do.
This was turning out to be one of the best nights of my life and it was about to get even better......