Riley Takes a Year Out Pt. 01

Tomboy decided to take a year out from her education and spend it in Ibiza

Part 01

Hi, my name is Riley and I'm eighteen years old. I grew up in a village on the outskirts of a large city in the south of England. There weren't any other girls my age in the village, only four boys so I used to hang around with them and it's fair to say that I grew up as a tomboy doing everything that the boys did and that included football and karate.

Although my periods started when I was thirteen my body never really started developing until this last year and I now have a 32A 26 32 body. Yes I'm quite skinny but I'm healthy and fit. I used to have quite short, dirty blonde hair but I stopped getting it cut about a year ago so it's now shoulder length.

As for my other hair, it only really started growing about a year ago and when it did I borrowed my mother's laser hair remover and got rid of any new hairs below my neck. Since then I've used it about once per month to get rid of and new hairs that decided to grow.

Although I'm still a virgin I had decided that I would loose my virginity sometime during my year out (that didn't work out) so when I decided that I was definitely going to Ibiza I went to see my doctor and got a contraceptive implant put in my arm. Since then I haven't had a period. The doctor warned me that this might happen and I certainly wasn't complaining.

My parents knew about my year out plan a good year ago and although I knew that they weren't really happy about it they said that I would be eighteen and it would be my decision. My dad did give me some advise and some money to tide me over until I could get a job over there.

I booked a flight for a couple of days after school finished and was really looking forward to it. But before that it was the school's Leaver's Ball which would be my last chance to see my friends for at least a year, some maybe never again. I decided to go all out and my dad bought me a nice summer dress which would feel strange to me because I hadn't worn a dress or skirt since I started at that school at over five years ago.

I tried the dress on but it didn't look right with a bra under it and my mother suggested that I skip the bra for the night. The bra was the opposite to trousers that I'd worn every day since I started that school even though I had nothing to put in a bra until a few months ago, another silly school rule.

Another new experience for me was a G-string. When I'd tried the dress on and smoothed my hand down the back the line of my full knickers was showing so mum bought me a pack of five G-strings for me to wear one for the Leaver's Ball.

As I was getting ready to go to the Leaver's Ball I had some very unexpected feelings. Not only did I feel like I had almost nothing on, which I hadn't, I got those tingling feelings in my pussy and my nipples which were making little tents in the front of my thin dress.

Previously I'd only got those feeling when my hands had explored my body in bed on a night or morning.

Daddy was taking me and my four mates to the Ball in his people carrier and the boys were waiting outside when I stepped out of the front door.

"Who are you and what have you done with our friend Riley?" Matt said when he saw me.

"Cut it out Matt, I feel weird enough as it is. I feel like I'm naked."

I could see that Harry and Mike wanted to say something but they both looked at my dad and decided against it.

"No seriously Riley," Matt said, "you look amazing, I'd forgotten that you had legs under those jeans."

I thumped his arm.

Dad dropped us off at the school gates and we walked the last one hundred metres. It was one of those rare warm, still sunny evenings and as we walked I said,

"This dress is going to take some getting used to." I said, "I feel naked."

"You look naked Riley," Harry said, "the material is so thin that I can see that you are naked under it."

"No I'm not, I'm wearing a G-string."

"I can't see that, only your butt crack and you've got nipples."

"Of course I've got nipples idiot, are they really that obvious?"

"We can see the darker circle of skin around your nipples." Tom said.

"Those are areolae and we've all got them."

"Not like those we haven't and those nipples. I could hang my coat on them."

"Stop it guys, I'm a girl and girls dress like this."

"You didn't used to Riley." Mike said.

"Well get used to it guys, besides, next week when I'm in Ibiza I'll won't be wearing much more than a bikini all the time."

"You're really going to do it then Riley?" Matt asked.

"Yes I am. My brain has been working overtime for the past year with all that damned school work and I need a break."

"I'm jealous." Harry said.

"We're going to miss you Riley." Tom said.

"And I'm going to miss you guys as well." I replied as I linked my arm with Matt's who was next to me.

"Ouch!" Matt said, "you just stabbed my arm with your nipple."

"Very funny Matt." I said.

But that pressing of my nipple against his arm, even though there was my thin dress, his jacket and his shirt between my nipple and his arm, had stirred up those tingling feelings again and my nipples did feel like they could have hurt Matt's arm. What's more, my clit was making its presence known and the G-string was getting wet. Something that hadn't happened outside my explorations in my bed.

We were greeted by the school principal who said that I looked beautiful, a compliment that I got quite a lot during the next ten minutes and I was starting to think that maybe I was. Although I could hear that most of the girls were getting similar compliments.

Thankfully, it wasn't bright sunlight in the school hall and no one else told me that they could see my areolae or my butt crack and I had almost forgotten about it until the dancing started. Now I was never that keen on dancing and neither were my mates but they all wanted to dance with me, especially the slow dances where they put their hands on me.

At first it was just round my neck or my waist but as the night went on their hands wandered both down to my butt and up to my tits. When it first happened and Tom's hands squeezed my butt I told him to stop being so silly, but he did it again and I realised that I actually liked his hand on my butt, the dress being so thin that it felt like his hands were on my bare butt. I could feel that tingling starting again.

Then when the tempo sped up a bit Tom's hands managed to find my tits and gave them a quick squeeze.

"Oh my gawd," I thought, "that was nice."

After Tom did it again I said that I had to sit down for a while and we went back to the others where I finished off my glass of the punch that one of the teachers had made. As

I put the glass down I said,

"Did Mr. Johnson sneak some vodka into that punch, I'm feeling a bit hot."

All three guys denied knowing anything about the punch and they said that they felt okay. I told them that I was going to the Ladies and when I got into a stall and pulled my dress up I discovered that the G-string was sodden.

"Bloody hell," I thought, "if wearing a dress and only a G-string does this to me I'm never going to wear jeans again."

I had a pee and dried the G-string as much as I could with the tissue in there then went back to the guys.

"You okay Riley?" Harry asked.

"Yeah, I guess that it's because of a few things but I feel 'different'."

"Like what?" Tom asked me.

"It's the end of an era, I'll never come back to this school again, I may never see any of you guys again, and this dress, I really do feel like I'm naked. Hey, guys, I want to thank you for being the best mates that a girl could every wish for."

"Cut out the sloppy stuff Riley." Mike said.

"No seriously guys, I want to thank you, thank you in a way that I can't in here, can we go outside, round the back of the gym?"

"Why?" Tom asked.

"Because I want you all to fuck me."

"What!" All four guys said almost at the same time.

"I want you to fuck me, my way of thanking you for being such great mates."

"But you're a virgin Riley."

"So are you, all of you, unless you've fucked some girl without telling the rest of us."

"No." All four guys said almost at the same time.

"Come on guys, I'll go first then the rest of you sneak out at five minute intervals."

All four guys looked a bit stunned but that tingling had made up my mind and I got up and walked out. As I walked I thought how happy I was, what better way to loose my virginity than my four best friends. I could have ended up loosing it to some drunken slob down a back alley in Ibiza.

Round the back of the gym I stood there. Apart from the music in the background it was deadly quiet. After a couple of minutes I decided that I was going to do the job properly and took off my dress and the G-string. I fought the desire to cover my pussy and little tits and nearly had a heart attack when I saw someone coming round the corner.

"Jeez, it's you Matt."

"Who were you expecting, the principle? You look awesome Riley, if I'd know that you looked that good under your clothes I'd have jumped you months ago."

"Thanks, how do you want to do this?"

"I don't know, I've never done it before."

"Neither have I. One of the girls said that it's best if the girl is on top when she first does it."

"Then that is what we shall do." Matt said as he unfastened his trousers.

"You shaved your pussy Riley."

"No, I thought that I told you guys, I borrowed my mum's laser hair remover."

"Oh yeah, for some strange reason I'm not thinking too straight at the moment. I like bald pussies."

"So do I." I replied.

As his pants went down I saw his cock for the first time and I was a little surprised.

"It's so big Matt, please don't hurt me."

"Have you still got your hymen thing."

"No, that went years ago when I fell off my bike."

"Good." Matt said as he lay on the grass.

"Face me." Matt said, "then I can grab your tits."

I put my feet either side of Matt's hips, started to squat then said,

"I'm nervous."

"So am I Riley, take your time."

I did and I gasped as I felt his cock start to enter me.

"You cock is much bigger than my finger Matt." I said as I gasped again.

"Oh that's nice I said as I went further down."

"Yeah, fucking awesome." Matt replied as I bottomed out.

I stayed still for a good minute savouring the new feeling and deciding that I wanted that feeling millions of times before I slowly used my leg muscles to lift me up. Then I started fucking him.

It only took a minute or so for us both to cum and it's fair to say that I was disappointed. I'd read that the first time, particularly for men, doesn't take long for them to cum, and the book was right. At least we'd both cum. As I felt Matt's cock start to soften I saw something in my peripheral vision and while I had my second heart attack of the evening I realised that it was Harry.

"Shit, you guys are really doing it, I thought that........" Harry said.

"Drop your pants Harry, your turn next." I said.

He did, and we did it. Matt had forgotten to play with my tits but Harry didn't forget and he played with my nipples causing me to moan quite a lot. Harry came just as quickly as Matt had done but I didn't cum at all.

Neither did I cum when it was Mike's turn but I had a really intense orgasm when Tom started squirting inside me. When it was all over I stood up, still totally naked and surrounded by my four best mates. It may have been late at night but it was a full moon and the gym had some outside lights that were on. For some reason that I didn't understand I was still feeling incredibly horny and sort of proud to be naked in front of them and not feel at all embarrassed.

I'd been naked in front of all of them before but this was different and I couldn't understand why, but I didn't really care, I was happy. Four boys that had all just fucked me were staring at me and I was getting more and more horny.

"I'm glad that you told us you have that implant in your arm Riley." Tom said.

"So am I." I replied.

"I brought some tissues Riley, I thought that you might be leaking." Mike said.

"Thanks, I am leaking quite a bit." I said as I started wiping my inner thighs and pussy.

Then I did something that I never do and threw the tissues on the ground.

"We should get back." Mike said.

We all agreed and, at intervals, we all headed back but I waited until last and what's more, I didn't put my G-string and dress back on until it was my turn to go. As I walked I realised that I'd liked being naked outside, and I'd liked it even more when my four male mates had been looking at me. I wondered if I'd feel the same if I didn't know the guys.

Anyway, we all got back inside without anyone asking us where we had been and soon the Ball was ending. As we left there was lots of hugs and some tears but we finally started walking to the road to meet my dad. I wondered if he would be able to tell that I was no longer a virgin. What's more I still felt as if I was naked but by then the feeling was a tingling in my nipples and pussy.

We arrived home and the guys went off to their homes with no hugging because I would be seeing them again the next day.

When I got ready for bed I didn't bother with my pyjamas and climbed in totally naked, the fingers on my right hand going straight to my clit.

*****

My fingers go busy again just as soon as I woke up even though my pussy felt a little sore.

During the afterglow of me cumming I thought about what I was going to take with me to Ibiza and I decided to re-pack my case. In fact I started to wonder if I needed a case and if just the sports bag that I used for my school gym kit would be big enough. The feelings that I'd had wearing just the thin dress and the G-string had just about made me decide that I didn't really need to take many clothes with me, that I would have more fun if I didn't wear much at all.

"Anyway, it's hot in Ibiza and I don't want to overheat." I thought as I tried to justify a decision to take very few clothes.

When I got dressed to go to meet my mates I decided to wear a skirt instead of jeans. The problem was that, apart from the dress I wore the night before, the only skirts that I had I hadn't worn for over six years. Amazingly, I could actually still get them all on, and fastened, but I had grown quite a bit and the skirts were all quite short on me.

Two of them looked quite childish so I put them back in the drawer and decided that I was going to take the others to Ibiza. I took the jeans that I had packed out of my case and replaced them with all but one of the skirts, the one that I was going to wear that day and to travel in the next day. I put on just that skirt and an old halter top then looked at myself in the mirror.

"Hmm," I thought, "look at those nipples making little tents, never noticed that before, but there again I always wore a bra before. Sod it, I didn't wear a bra last night and I felt good, I haven't really got much to put in a bra anyway so why wear one? It's going to be hot in Ibiza and a bra will be uncomfortable."

I went to my suitcase and out came all my bras.

Next I looked at the skirt that I was wearing, yes it was short. I turned my back to the mirror and bent at the waist then giggled as I saw my bare butt cheeks in the mirror. Standing up I thought,

"I only wore that G-string last night and my pussy was tingling and leaking all night, did mum know that wearing one would get me all aroused? Whatever, it was nice."

My, by comparison, big knickers came out of the suitcase and four G-strings went in. Then I thought about what I was going to wear to travel. I'd just decided that 'big' knickers were out so I'd have to wash the G-string that I wore the night before, but that meant that I didn't have a G-string to wear that day and I didn't want to go back to wearing 'big' knickers, besides I was going to meet my mates and I wanted to fuck them again hoping that we'd all last a bit longer the second time. Knickers would just get in the way so I decided to go commando all day.

I went over to my suitcase and went through the clothes that were in there -- again, but this time I was thinking about how nice I had felt with just the thin dress on. Out came a few thick tops, jeans and shorts,

"Way too thick," I thought, "they wont make me feel nice."

Looking at my nearly empty suitcase I decided to see if I could still get into any of my old sun dresses and see if any of them still looked okay on me. I quickly took off the skirt and halter top and got out the four old summer dresses. I quickly discarded one because it looked too 'little girl' the tried the others on. Amazingly I could still get in to all three of them. Okay one was a bit tight but it was on.

"Did I really wear summer dresses that were that short all those years ago?"

I thought then kicked myself as I remembered that I'd grown a lot since then but wow, all three were really short. I did the turning my back to the mirror and bending over thing again and smiled three times as I saw my bare butt three times.

"Hmm," I thought, "have to be careful wearing these in Ibiza. Or not," and I giggled.

Being summer dresses they were all light weight and thin, and because I'd worn them a lot when I was little they were worn even thinner. As I folded them and put then in the suitcase I realised that they hardly increased the volume of the things in there.

Satisfied that I now had the right clothes to take with me I again looked at the suitcase and decided that everything would fit in my sports bag so I swapped them over.

"That's better, less to carry around until I find somewhere to live." I thought, "and dad will be pleased that I'm not taking one of the set of luggage cases."

Happy that I was organised I picked up the G-string that I'd worn the night before and went to the bathroom to wash it and to have a shower.

Back in my room I hung up the G-string to dry then put the skirt, halter and my school trainers on and went downstairs. As expected I was alone in the house because mum and dad would be at work so I got myself some breakfast then went out to meet my mates.

As soon as the sun hit my exposed skin and the warm air tickled my pussy I felt naked again. I even looked down to make sure that I had put the skirt and halter on. I felt my nipples and pussy start to tingle but I kept walking to our regular meeting place, the kids playground at the edge of the village.

Matt was the only one of my mates already there and as I walked up to him he said,

"Looking good Riley."

"Thanks, I'm still getting used to wearing a skirt, and this one is so short."

I sat on the little roundabout opposite Matt and he said,

"Going commando as well Riley, you are feeling brave today."

I bent right over and looked up my skirt. I could see the front of my slit and my clit sticking out.

"Yeah," I said as I straightened up, "I liked the G-string last night and my mum bought me a pack of five. I've put four in my bag to take with me and washed the other one for me to wear tomorrow."

We made some small talk until the others arrived, each of them commenting on my choice of clothing. Then Matt announced that I was going commando for the day and of course the other three wanted me to prove it so I stood up and pulled my skirt up to my waist.

"There, satisfied."

"You look good Riley." Harry said and Tom and Mike agreed.

I dropped my skirt ending the show as Matt said,

"You looked good last night as well, both with the dress on and without it on."

"If your trying to make me blush forget it."

"But are we making you tingle Riley?" Mike asked.

"My pussy and nipples have been tingling since I walked out of our front door, look at my nipples, rock hard and throbbing a bit."