VANILLA.
***This is my first real story. It takes a little time to get underway, but I hope it's still a story that will get you going. I'm sure that by reading it all you'll get a lot more out of it. Vanilla *is* based on a girl I knew at school, and she was really hot! Please email me comments.
Oh, if you don't like incest stories then this is probably okay for you to read. It'll get a bit more incestuous in later chapters. If you're incest curious, this story'll introduce you to it gently! If you like incest stories, then this is for you!
Note: contains no pedophilia! I hate pedophilia!
Email comments to: maskedguy@email.com
If I get no comments I won't write any more :(***
Book I. Part I.
Vanilla is a member of the school "dream team". 5 feet 8 inches tall, she wears skirts which ended two inches above her knees. Her legs are tanned and taut in the manner that Playboy models strive for but only schoolgirl netball players can achieve. She generally wore small black shoes over white socks which rolled up to just below her knees. The socks always had a pattern, five different patterns for the five days of the school week. Her blouse is the school white, and barely seethru - just thin enough to see the white lacy pattern of her bra if you stand and look close enough. The material is always tight, showing the swell of her youthful breasts. Over this she wears the black school tie with red banding indicating her House.
Her face only adds to her status. The large brown eyes are the first things which grab you, liquid and soft. The whites of her eyes are always clear, with never a vein to be seen. Her pupils dilate easily. Her nose is a gentle outward curve, the ending a tight little nob. Neither Nazi thin nor Jewish thick, her lips are always painted with pure maroon colouring. The whole shape of her face is a flowing curve, with high cheekbones and a strong jawline, topped with a sprinkling of chocolate freckles. Framed by the long, dark hair with a natural curl which ended halfway down her back, she is a dream.
Vanilla has always behaved very unusually. She scored top marks in every class, and is known to have been a virgin until she hit sixteen. Even the guys in the school (and guys are known to brag about such things if a nice girl even looks at them) did not brag about having slept with her. There weren't even any rumours about other things sexual. Her boyfriend kissing her was the height of gossip that we could find about Vanilla.
Now, it isn't due to her parents being particularly harsh - they left her alone in the house for the occasional end-of-term party. It isn't for the lack of offers or boyfriends - she had plenty of those.Rather it seemed simply because she wanted to be a virgin. Her boyfriends usually lasted a term, and she had one for five out of ever six terms in the year. The other term, the exam term, she studied hard and I didn't ever even see her at the shops.
Vanilla was never a jailbait girl.
On her sixteenth birthday in Math, a couple of the guys got together and made a card. They wrote down ever guys' (and a couple of girls') names on it, along with times and places. It was the middle of summer and the last lesson of the day when they handed over the card, tiredness pushing aside the usual respect for the lovely Vanilla. Vanilla took one look at the card, smiled and laughed her soft laugh, and then placed it in her bag. We found out two weeks later that she had picked a name from the card and gone to the location. One of the guys had turned up there, shaking with anticipation (I think we had all gone, just in case). She slept with him.
Vanilla had no longer been a virgin, and it made her even hotter in most peoples' eyes. Even the teachers seemed to have been talking about the incident. Vanilla has told me she knows the teachers look at her - both the male and female - in that hungry way. She doesn't use it against them, not in a big way. Instead she weasles out of the occasional late mark or missed piece of homework, but only when she had a genuine reason. It is a particular skill of hers.
I loved looking at Vanilla. There are plenty of chances to look at her. The school stairs have wooden handrails with metal bars to hold them. They also wound downwards, straight for 15 steps, around a corner, and then down another 15 steps. They're open, and airy. Standing halfway down the lower set of stairs, you can see almost all the way up the skirts of the girls coming down. Most of the pretty girls had good thighs, but Vanillas are perfect. Strong and long, perfectly proportioned. Guys would escape classes early and wait on the steps below where she is, just hoping to catch a look. Not that Vanilla seemed to care - it didn't stop her wearing the short skirt or the white panties which occasionally (on really lucky days) I've managed to catch a glimpse of.
Vanilla teased everyone. She would drop books and bend over showing us her strong buns more often than could have accounted for being clumsy. She would hug her arms so that her breasts stood out underneath the shirt. She sat cross legged and showed her favourite teachers a glimpse of those wonderful thighs. She is always up and down on stools for the older teachers, fetching things from the high shelves in maths or the science labs.
Swimming is an almost compulsary event amongst the boys of her year, and the year below. To see Vanilla in her plain, sport cut purple costume is an experience to miss football for. She ties her hair into a ponytail and practices backflips from the side of the pool. When it gets wet the costume is tight - tight within the boundaries of convention but still delicious. I love Fridays.
Netball is another big event in the school, all down to Vanilla. The school sport uniform is a short purple skirt, and a white t-shirt. Vanilla wears tight cutoff cycling shorts underneath, and a dark blue sports bra. Seeing her jump around the court, her breasts shuddering slightly as she lands, has boosted crowds from maybe twenty bored parents to a squad of cheering schoolkids from all of the years. Many of our dads have taken up an interest in the sport too since Vanilla turned fourteen and started to develop.
That's not all there is about her though. I was in the same class as Vanilla when we started highschool, and our friendship has continued since then. We often study and play outside together. I've even been to a few of her parties - the ones that aren't sleepovers. Vanilla has the BEST personality. She's a dream to talk to. She jokes, she smiles, and she can discuss anything from any of the classes. We're both interested in the same TV programmes - documentaries about wildlife and space. We get along so well. Her eyes flash when she's interested in something, and she's always interested in you. It's a sure way to keep bullies off my back, because they all respect her.
There's one thing I don't understand about Vanilla though. She's a flirt, a tease, and fancied by all of the guys in the school. The thing is, she flirts with and teases all of the good looking guys, the popular and the brave. She's been moral support for the football and rugby teams since she hit the school, and has major followings amongst both of them. But she only sleeps with geeks. All of her boyfriends have been geeks; her favourite teachers are geeks; even her true heroes are geeks. She's given blowjobs to half of the maths club, but none of the football team. She's slept with the top of almost all the classes within our year - but not the P.E. class. None of the guys she's slept with have been good looking - mostly ordinary, and some have been spotty and totally oily. I've become friends with the majority of them because Vanilla likes to get to know guys before she sleeps with them.
So that's Vanilla. Gorgeous, intelligent, the most fancied girl in school. She only sleeps with geeks, and I'm a geek. She hasn't slept with me. Yet.
Part II.
"Vanilla!"
There she is, ahead up the street. She's wearing her school uniform. I run up to her, panting under the summer heat and the weight of my backpack. The bell went ten minutes ago, but Vanilla left early and I've run all the way to catch up with her.
"Hi Charlie!" She smiles, her dark brown eyes lighting up on seeing me.
"I missed you outside class."
"Yeah, I know. My parents are away until late tonight, and I want to get home to do some study and sunbathing." Vanilla loves to study and sunbathe. She says it lets her look after her body and her mind at the same time. I was stumped for words, as I always was when I first met her.
"So... what do you think of the maths homework then?" She broke the silence.
"Wow. Difficult. I'm never going to get symultaneous equations into my head. Mr Young is a shit too, setting them on the weekend. I wanted to get out and walk down the Wirral Way, but I'm not going to get the chance now."
"Ahhhhh. Young's not that bad. He's just got our best interests at heart. I wanna know this stuff if I'm going to Uni." Her lips were painted maroon, like usual. The only makeup that I had ever seen Vanilla wear to school was her lipstick. It was banned even then, but none of the teachers told her to take it off.
I kicked at a stone. "I'm not going to get it though. I like Science better. That's fun."
She seems to think for a moment, and I watch her long legged stride as best I can. Her legs are smooth, and shining slightly in the sunlight. "Say, you don't want to come to my house and work on it with me do you? I can have someone around. It's okay with mum and dad, so long as you don't want to stay to late."
"Sure." I answer before I realise the word is out of my mouth. "I'll have to call my parents though."
Her eyes flash. "That's fine."
We spend most of the rest of the walk home talking about the school day, and a documentary we saw about Venus in science. Most of the other guys had been messing about, but I paid attention. Venus is so beautiful in the night sky. The weather is burningly warm, and I'm embarrased about how much I'm sweating. I should excersize more, but nothing I seem to do puts weight on my coathanger-thin frame. Besides, I enjoy walking more than running, because then I can look at the scenery. My glasses slip down my slick nose a couple of times, and I push them up with my forefinger.
"You should get contacts." Says Vanilla. "You'd be so handsome with contacts."
"My parents won't pay for them."
"Shame."
We get to Vanilla's house, and walk up the path between the flowering plants. I try not to sneeze, but my pollen allergies are high. Vanilla grins and hands me a tissue.
"Thank you."
"You're so sweet."
Entering her house, we dump our bookbags in the hall. Vanilla shows me through to the kitchen and gets me a Coke from the fridge before disappearing upstairs. I'm so nervous, but I sit down at the table and sip my drink. It's cold and fizzy, giving me a little gas.
My imagination is running riot. What is Vanilla doing upstairs? I can hear her bumping about, and think about the red bikini I know she owns. I've seen it before on their washing line, and I hope that she's going to wear it. More likely she'll wear the purple one though, which is nice but a little more modestly cut.
The clock is ticking. It seems to be taking her ages to get ready. She goes into the bathroom, I hear the chain pull and then her feet thump across the floor. There's a sudden thud, and then silence. I wonder if she's just done a handspring onto the bed? I hope so.
What was that?
"Charlie! Charlie? Will you come upstairs a minute? I've got something to show you."
My imagination runs wild. I set down my coke on the table and head to the stairs. "Vanilla?"
"Yes Charlie. Come up here will you?"
I run up the first couple of stairs, then slow to a walk. One, I'm not fit enough to run stairs in this kind of heat and two, my imagination is going to be better than what actually happens. I bet she's going to show me a new magazine or something. Science is fun... but I can't keep my mind on it. I'm imagining Vanilla laying naked on the bed waiting for me, masterbating like a girl in a cheap porn magazing. But I can't imagine it all. I haven't seen that many breasts outside of clothing, and I have definately never seen between a girl's legs. The closest I've come is looking through the Kays catalogue at underwear. None of the models look as good as Vanilla.
I've reached the top of the stairs, and head for Vanilla's bedroom. It's second on the left. The door is shut. I knock.
"Come in Charlie."
I turn the handle and push open the door. I imagine her standing there naked, waiting for me with that warm eyelit smile. I imagine her with a magazine in hand, pouring over it interestedly, wanting to show me an article. Maybe I'll get a look at her panties...
But as I look, she isn't wearing panties...
Part III
In fact, that's all she isn't wearing. She's laying on the bed in her full school uniform. She's pulled back her hair again neatly, taming some stray locks. It cascades over one shoulder. Her school shirt is neatly tucked in. Her socks are pulled high, returned up her calves which were naked for the walk home. Her little black shoes are held on her feet by neat laces. The only thing out of place is her skirt, which is hiked slightly on her thighs. She's laying back with her legs bent up, and I can just see her naked bottom peeking out.
I'm gasping, and I know it. For a moment, I wish it had been the magazine. At least then I would have known how to act.
"Come in Charlie. Leave the door open. It's so hot in here!"
The window is open, and there's a nice breeze blowing through the room. Not that I'm noticing that much. My face must be beet red, because I can't stop looking at Vanilla's peeking naked bottom.
She giggles. "Here Charlie, take a better look." Now she's lifting up her skirt, and I can see a patch of hair between her closed legs. She's rolling over, and the globes of her taut little bottom stand up in the daylight. She's a dream in school uniform. I've beaten off over this thought so many times.
"Like what you see, Charlie?"
"Ye... yeah."
"Good!" That big, warm, maroon smile over her shoulder. "Do you want to fuck me?"
I jump. Hearing that kind of language coming out of Vanilla's mouth is a shock! She hardly ever swears. It just makes me harder though, and more excited. I can hardly think straight. I can hardly focus on what she's asked me.
"I'm hoping you want to. I mean... most of the guys in school do. Some of the girls too. And the teachers! Geeze. I get so hot with their eyes on me all the time. I like to flirt with them though." Another giggle.
I can't find any words. I feel stupid. I think I can manage a "Ye... yeah."
Vanilla smiles with her soft lips. "I was hoping so. I'm so hot. You sound dead nervous, but I'll look after you Charlie. You don't have to worry. I've done this before. Just go with me, hey?" She's rolled over again, and is now offering me her hands. Her skirt is hiked up around her waist, and her legs are slight apart. I can see the lips of her soft, pink genitals. I want to explore them. They're the best pleasant shock I've ever had.
I take her hands. She's having me sit down on the bed next to her. I can feel my penis tented in my trousers, and her eyes are looking at it. Then they look back up at me again. She's leaning forwards, and I can't get my eyes off hers. "But you have to do something for me. Two things, really. First, we have to talk. You have to tell me a secret about yourself."
"A secret?" I look between her eyes and breasts, breasts and eyes.
"Well, not just any kind of secret, Charlie. A deep, personal, naughty, dirty secret."
I'm quiet for too long.
"If you can't, that's okay, but it means we can't fuck. It's a promise I've made to myself Charlie. I know you so well, like I do all of the guys I've fucked, but I need to know something deep. Besides, it really turns me on!" The last part she says warmly, and I know it would be good to 'turn her on'. I'm thinking about the way she says 'fuck', too, like it's a delicious but dirty word. She always slightly whispers. I don't want to be quiet for too long though, because then she might think that I don't want to have sex with her. Or see her pretty bottom again. What can I say? I suppose it is the right time...
"I beat off thinking about you."
Vanilla is smiling. "That's okay. But it's not really a secret. I already knew it. I already know that most of the guys do. I like it. It's a good thing Charlie, but I need to hear something more, okay? Something deep and dirty."
What do I say?
"Have you ever fucked with anyone else, Charlie? I mean, you once said there was but I don't know of any girls from school who've said. Is it one of them?"
I'm blushing deeper. I remember the girl I was thinking about at the time, and it wasn't a girl from school. I feel my face fall. It wasn't true but...
"Oh, you can tell me! It's okay. It doesn't go any further than the walls of this room. It must be really dirty!"
I can feel her hopping slightly on the bed, and she's wiggling her bottom around. Geeez. I really hope this doesn't go further, because it isn't true...
"My sister. I've slept with my sister..."
Her mouth is open. I'm scared! Incest, of all things! Charlie! I'm an IDIOT FUCKER!
Part IV.
No... wait... she's smiling again. She's grinding her bottom against the rough wool of this cover even quicker now. What...?
"THAT IS SO INCREDIBLY COOL, CHARLIE! IT MAKES ME SO FUCKING HORNY! YOUR SISTER IS A BABE!"
Now she's pushing me back on the bed. I'm going with it, not quite sure, but feeling relieved. She's unzipping my keks, and taking my penis out of my y-fronts. Now her mouth is on it. Oh, that feels so good! It feels like shimmers of hot spikes rushing through me! It's way better than giving myself a handjob! I can feel her lips through the skin of my hardon, which is raging bigger than I've ever known it. She's moving up and down, leaving streaks of maroon! Oh Jesus! This is so hot, so incredible, more than I've ever dreamed of. Vanilla is giving me a blowjob! Look at her dark hair, it's obscuring my penis and hips. Look at the way her skirt is hiked up so I can see her bottom. It's moving in the light from the window, pink and wonderful. I don't know what to do. I'm too excited! I can feel the cum rushing up my vein!
She's stopped. Phew. I didn't want to look inexperienced. She's stading up, her skirt falling down to two inches above her kneecaps again. My memory of her naked bottom and pink slit is so vivid though. What's she doing now? Crossing to her dresser... taking out a packet... OF CONDOMS. Oh Christ!
She's taking one out with her teeth. Now she's reaching down between her legs. Putting her hand under the waistband of her skirt and staring at me really fixed.
Around the condom, she's saying, "Charlie, you've gotten me so hot! You like this? Like watching my rub my genitals. I'm touching my clitoris. Doing it all for you. You get me hot."
Now she's stopped. She's licking her hand, TASTING HERSELF. Jesus. This is so incredible. My cock is jumping. How good must she be able to make herself feel with her hand? I want to rub her just like she was rubbing herself. Her moist, pink genitals. Get my hand up that skirt I've spent so long looking under. Run my fingers through her pubic hair, and that slit. Finally know what it's like. Heck, I'd settle for seeing her bottom again.
She's over by me on the bed now. Opening the condom... popping it into her mouth... what? Now she's going down again, like to give me a blowjob... her mouth is over my jumping, twitching penis. I can feel her tongue, the moistness of her mouth, the rubber of the condom... It's slipping over my penis! She's sheathing me with her mouth! It's gone all the way on!
"Wow!"
Vanilla looks up, and grins. She holds still a moment. She knows I want to look at her. There she is on her hands and knees on the bed. She still has most of her uniform on, and it's all impossibly neat. Her tie is tucked in. Her hair is tumbling over her back and shoulders, some strands brushing my aching penis head. Her tiny shoes, the long socks pulled up, the short skirt rucked up around her hips again, the way her breasts fall in the white lacy bra inside her tight shirt...
A vision in a school uniform. I want her!
She knows. She sits up, pushes me back to laying full out again. Now she's climbing onto me, and I get a good view of that pink slit with the patch of dark pubic hair at the top. She's rubbing it. Oh, now she's stopped and she's taken hold of my condom-sheathed penis. She's lowering herself onto me! The body that I've dreamt of for so long. Those heavy breasts, that thin waist, those wide hips, all of which must be tan and muscular...
She's on me! "OH FUCK!" That smile. Her pupils have dilated wider than I've ever seen. Her freckled face is warmed in lust.
It's so tight around me. Pulling at me. Drawing me in wetly. I feel as though I'm going to hurt her or be hurt, but she's got me all in now. I can feel my balls against her. I can't see her though. The skirt has fallen down again, and she's started to draw herself up and down on my penis. My uniform is crumpled, and she's holding onto the front of my shirt. Pinching at my nipples through it. That feels amazing! I never knew. How did she...?
ARGH! Now she's really going at me! I can't hold still! My penis feels like it's going to explode brutally but there's nowhere for the pieces to go. All I can feel around it is a brutal, rippling mass of suction. She's trying to draw my sperm out and make me come! Her eyes are closed and her face screwed up. She's moving faster! Jesus oh shit! My body is alive with energy, sparkling and rippling. I can feel myself twisting, driving myself backwards into the bed. It's so incredibly incredible!
"Oh Charlie..." She's gasping. She's mixing my name with God's. I feel so powerful.
Now a lock! Her muscles have locked around me! They're squeezing! I can't see anything! Rainbows of colour and nothingness! I can't...
I'm COMING! It's lashing into her, and I can vaguely hear her screaming and feel her nails ripping my shirt. I feel like I have her fixed above me on a huge spike, my beautiful bestfriend girl. My sperm is pumping into her, filling her tight little body and vagina. She's writhing. So am I...
It's over. The most amazing moment has passed. My minds coming back, and it seems like the rest of my life will be an anticlimax. That was so intense...
"That was so intense, Charlie... Urgh... Oh God..."
She's collapsed on top of me. My penis is still inside her, and I can't feel it softening. Vanilla is keeping me alive. She knows so much for being my age, sixteen. She knows how to use her tight little body...
"Charlie?"
"Yes." I don't know how I managed to say that.
"Charlie... I want to see you fuck your sister..."
The memory of that comes back, and suddenly I'm afraid...
Part V
I refused. What else could I do? Fuck, as Vanilla would put it, my sister? There was no way. I rang her on the Sunday (after little sleep and feverish dreams of my sister and Vanilla). She didn't speak to me for weeks after that. It was halfway through the summer holidays before we bumped into each other, and started talking. Which rapidly led to an argument.
"I trusted you. I let you sleep with me. You lied to me, and I asked for one little thing back, and you wouldn't do it for me. What kind of friend are you?"
I didn't see sleeping with my sister as "a little thing", and told her so. She gave a grin. "Okay. Maybe it's not that little. I didn't mean to say it like that, to make it seem like a small idea. I'm sorry for saying that. But still, it would be great to see you with her. It got me *so* hot, Charlie. You could have me for life if I could just see you with your sister. I'd be wet *forever*."
"There's no way I could do it, Charlie. No way. I mean, how would I even start?"
"But you want to?"
"Well..." I blushed deep. "It gets me hot too, but it seems so naughty! There's no way she would go along with it."
"You don't see anything wrong with sleeping with her?"
"I do! That's the problem. She is hot, Vanilla..."
"You can say that again..."
"But let's just forget it."
"So if you're against that, where would your lines be, Charlie?" She was holding my hand now as we walked along the highstreet. It must have seen very unusual to the people around us, but I had come to the city to buy some stuff you could never get at our local newsagents. It was eight miles from home, and there were so many people on this hot sunny day that I didn't think anyone would overhear us enough to cause problems. Besides, it had started out as an argument.
I shrugged to answer her.
"What do you think of gay sex, Charlie? Homosexual, I mean?"
This stopped me. "I..." I couldn't quite make up my mind. "I don't see anything wrong with it if two parties enjoy it. And they're old enough to make the decision."
"C'mon. Tell me. We're friends. What does the thought of me with another girl do for you, Charlie? Have you ever thought about it? Fantasized?"
I blushed, but the memory of a fortnight ago was very strong. I was feeling very relxed in the sunlight, surrounded by the excitement of shopping. I had planned to buy my first porn magazine today. I had missed sex so much since my first time with Vanilla. My hand just didn't seem the same anymore. To put it shortly, I was horny.
"Yeah. Of course I have. You're beautiful Vanilla. You and another girl... I'd love to see it."
"What would you say if you could?"
I gulped and stood still in my tracks. The crowd seemed to flow away, leaving just me and Vanilla there. And a tantalising thought of her naked with another girl. Vanilla was wearing some very casual stuff today - a pair of tightish jeans and a white top which showed her arms and tummy. She had on her cowgirl boots too, but they were mostly hidden under the bellbottoms of her pants. Her hair was tied in her usual ponytail, and her only makeup was the maroon lipstick. Like me, she wore a pair of shades with plastic rims. She looked older than her 16 years - 18 or 19 maybe. I probably looked about 16. Like her brother... but I had to stop thinking of that.
"I'd say... It'd blow me away." I wasn't about to pass up this offer, if it was an offer.
She grinned, and then tilted down her shades so I could see her eyes. "I can do it Charlie. Jenna Jameson. The girl from 1b? I'm pretty sure she's interested in me. She sure looks a lot. And she has a great body. I'd like to try it with her."
I gulped again, feeling dry. She must be teasing me.
I stopped to lean on the Rows for support, and she rested her arm on mine, standing close to whisper in my ear. "I would do it, Charlie. But you'd have to do something for me in return."
That was it. But was it too much? I mean, do something for Vanilla to see her with JJ, one of the top brains in the school, and not a bad body to boot?
"What?"
"I want you to fuck with my brother."
Part VI
Vanilla had set the diningroom up perfectly. The whole place was candlelit, soft and yet quite bright. The curtains were drawn for modesty (much to my relief). There was a thick blanket on the table, covered by a soft white linen sheet. Any mirrors had been covered up, and all breakable objects removed from the room. The walls were hung with some red sheets with slightly frayed edges, obviously left over from the 70s. Even the TV had been covered up. There was soft music touching the air.
When she had said "fuck her brother", Vanilla had meant more than that. She had explained her plan to me as we sat in privacy by the river. She wanted to watch me have sex with him, just as I wanted to watch her go with JJ. I would have to do it first, because it was more of a risk for her to try to proposition the other girl than it was for her to get her willing brother with me. Also, she said I owed her.
Vanilla had a very strange, but always right seeming, sense of debt. If she ever got into debt, she wanted to pay it off straight away.
She expected others to do the same. In that way, she was very trusting. Overly so.
So Vanilla had set herself up a soft lounge chair in one of the corners. It was filled with pumped cushions, and had a little table beside it with a drink for each of us, a tub of vaseline and a packet of condoms.
When we had first been discussing it, I had been afraid that she wanted to take photos or video. Not so. Vanilla wasn't like that. She just wanted to watch us. I was very relieved at that. Doing this was something which had taken a lot of encouragement from her. She had taken me home and stroken my penis until I came. Then she had stood up and, right there in front of me, taken off her knickers and masturbated with them. She finished the deal by giving me the white cotton underwear to take home with me. As I wanked that night with them wrapped around my penis, I decided to go along with her. How could I not?
As I sat down in the chair and nevrsouly explored the room with my eyes, Vanilla came in along with her brother. There are two things to understand about him.
First, he is exactly ten months older than her, in other words a year above us at school. In every other respect he is her male double. He has the same large brown eyes; the same brown coloured hair (although his was cut short and parted down the middle); a similar pair of middle thick (or thin) lips; and a smiliar body shape (without the obvious parts, but with the same girlishly wide hips.) He has soft skin which makes him very special amongst the girls.
Mike is also a member of the school cricket team, which makes him very fit. He's clean cut to the point of moviedom, and one of the most fancied boys in the school.
Secondly, Mike is gay. Not many people know about it, and as far as I know I'm the only guy in that circle. Vanilla quietly told me about it when she found out, because she believed that I could be trusted and me and Mike were good friends. We still are good friends.We hang out a lot, and I like to watch the cricket team play. I've even been part of a few games myself even though I'm a little small and useless with the bat.
So when he entered, I gave him a shy smile. He winked and gave me a "Hi mate!"
It mustn't be easy being gay in school. Mike is confident enough to carry it off without any hassles. He's just never had gay sex. Like Vanilla he's been very careful (the gay scene in school is hellish). Getting a date has been impossible for him.
I noticed that tonight he looked very feverish. His face was glowing. I wondered how Vanilla had broken it to him - and also how she'd told him about her wanting to watch. Or had they set it up before she even asked me?
I stood, giving Vanilla the chair. She smiled, kissed my cheek, assurred me everything would be okay, and then sat down. She looked a vision. Her face was also feverish. Her body was covered by something very like her school uniform, but different. She wore a greenish, tightish shirt which showed off her breasts. It had been tied in a knot to reveal the lower part of her ribcage and her bellybutton. Her normal school skirt was in place, although she had replaced the usual kneehigh socks with her cowgirl boots. They were laceups and had tassles at the top. She had even put on a white cowgirl hat and her shades. She looked beautiful, enigmatic and in no way anonymous. Vanilla had not tried to hide who she was. I wondered if she had dressed this way to get me excited. It was working.
Mike was dressed less showishly. He had on a pair of bluejeans, a loose white t-shirt and his school shoes. He was chewing a sweet (as always).
We guys both stood there and looked at one another for what must have been two whole minutes. Then Mike (being the much more confident one of the two of us) took the initiative. Although he'd never done this before, he obviously knew what he wanted and was excited about it. I could see his cock already hard in his pants.
"Okay, Charlie. We both know this isn't going to go anywhere long term, but I just couldn't wait any longer. When sis told me you were okay with the idea, I really just jumped at it. Now I'm so nervous mate I can hardly stand. So let's get it through and enjoy it, okay? I know more than you, because I know you've not been into gay stuff. I've at least seen some videos, and I know what I want. I guess since sis is giving you something in return for fulfilling one of my fantasies and one of hers, I get to take control."
I nodded. Mike was jabbering quickly, but he obviously knew I was even more nervous. Him taking control helped amazingly. I felt safer, both because he was a friend and because he knew what he was doing.
Vanilla just sat there and watched, a warm expression on her face.
"Can you take your clothes off for me, Charlie?" Mike said.
I looked down at myself and, fumbling with my buttons at first, removed my shirt and then pants. I'd taken my shoes off earlier, and so all I stood there in were my cotton y-fronts and socks. The room was at least warm, though my nipples stood up anyway. My penis didn't know what to do. Vanilla had gotten me worked up enough with her outfit and promise that I had a semi-erection, but I was too nervous to get completely hard.
As I watched, Mike removed his clothes until he too was only in his boxers. I would have worn some, but mum only ever bought my y-fronts. His body was strong, far more muscular than mine, and he had a gentle tan. He even had slight ripples on his arms - a very advanced body for our age. No hair though - just like me. His was probably thorough shaving - mine was because I hadn't grown any there yet.
I took a quick look at Vanilla, and noticed that her wearing of the shades had been to cover up her eyes. I couldn't see where she was looking, although I suspected my white briefs would feature in it. At least I hoped so. I could almost feel her eyes on my penis, and that made it stand a little more erect.
"Now Charlie, move over to the table and face away from me. Place your hands on it, and bend over."
I did as he said. It was very easy listening to my friend telling me what to do. I felt his hands on my bottom, stroking it gently through the material of my underwear. He started on the outsides of my cheeks, and then worked his way to the crack. He seemed to spend a lot of time there, and because my bum was so sensitive (especially the hole) I got fully erect. Although he was a guy, it felt so good to be touched there. I had always wondered if I could be gay. I often admired my bottom in the bathroom mirror and touched myself back there.
As I stood there with my feet increasingly wide apart, Mike slid down my y-fronts and had me step out of them. He kept running his finger up and down my crack, lingering at the bottom.
So quickly that it choked me with pleasure, he ran his finger over my bottom hole. I literally jumped, and heard an "ummmm" in Mike's deep voice. He slapped my cheek, and then ran his finger down between my parted cheeks. At my hole he stopped the movement and started to tickle. I didn't know whether to gasp or giggle. It tickled in such a good way. I had forgotten my apprehension that Mike was a guy and concentrated on his finger. I heard him kneel, and felt him kiss each of my cheeks. Then I could feel his breath as he inspected my hole up close. He kept tickling, and I was whispering a groaning. Vanilla hadn't done this to me, and it was driving me wild having my bottom explored for the first time. I wondered briefly what she was doing in the chair, and then stopped as Mike moved on. He changed his fingering to a slight pressure, and his finger popped slightly into my rear. I could feel myself involuntarily try and drag his finger into me, but he kept it where it was, wriggling the tip slightly.
Just as I thought that I was going to come without even any touch on my penis, Mike stopped. My erection was raging, almost touching my stomach as I bent over, hips thrust back, bottom exposed. I was his, and he must have known that by now. He reached between my legs, gave my balls a quick squeeze and then stepped away. I looked back over my shoulder, seeing the identical blushes on the sibling's faces and Mike picking up the jar of Vaseline. He saw I was watching and smiled, dropping his boxer shorts and kicking them away. The action made his penis - which was about an inch bigger than mine and the same circumference - leap. He was so erect the skin on his shaft was gleaming in the candlelight. The foreskin was pulled back tight, exposing his purple and red head.
Mike grinned after seeing me look at his manhood. "Like what you see, Charlie?"
"Oh yeah." I gasped. I wondered if I was gay. I knew then that I was at least bisexual. I'd looked at other guys in the showers before, just like any developing man, but had never seen another erection.
Vanilla smiled happily, picking up the box of condoms and starting to open it.
Mike took the Vaseline, pushed his finger into it, and then came up behind me. I turned back to face forwards, knowing what he was about to do, and he inched his finger up my rear. My muscles grasped at it. It felt amazing as I clawed his finger up my bottom. This is how Vanilla must feel. Awesome. I squeezed his finger tightly, and he added a second. I screamed at the pain, and he smacked my cheeks. He seemed to be getting into the role, and I wasn't exactly afraid. I was standing there, bent over with the first two fingers up my bum of the brother of the woman who had taken my virginity. And she was watching us, removing a condom so he could push his penis up where his fingers were. I groaned and wiggled backwards onto them. I felt his penis brush the back of my leg, and shivered. I wanted to reach back and take it, but then his digits left me and I felt empty.
"He's ready. Give me the johnny." Mike said. He was obviously in a rush now. He must have taken the condom from his sister, because I heard it slipping on, stickily unrolling. I recognised the sound from when Vanilla had put one onto me. At least he was being careful.
Mike came up behind me and put one hand on my shoulder. I looked backwards and down, and saw the other held his penis ready at my bottom hole. "You okay, Charlie?" He asked, suddenly seeming sheepish.
"Yeah..." I thought how good his fingers had felt, and about Vanilla and JJ... "...go on."
His head felt huge as it pressed against my hole. He guided it forwards, and it started to inch inside me. GOD IT FELT GOOD! My own penis was aching, needing some stimulation to bring me off. I was shaking too much from his entry to touch it though. Instead I concentrated on the tight clinginess of my hole and trying to draw Mike up and up into it. Eventually he bottomed, sliding in the last two inches in one go, and I gronaed with passion. Then he began to move, and I was surprised how easy and natural the whole thing was.
"God Charlie, you're so tight! So slick! I never knew it would feel like this!"
All I could say was "Go on!"
He started to fuck me faster, violating my back passage with forceful and yet well guided strokes. He shagged me like I wanted to shag his sister, with control. I could feel him tickling my prostate, and knew that I couldn't hold back for long. It was a wave of pleasure rippling through me, making me jerk on the table. I collapsed downwards onto my arms, and each stroke of his made the table shake. I felt one of his hands smacking my cheek hard, but it only seemed to expand the pleasure spot.
His groaning got louder, as did mine, until I felt his penis tense. Then he seemed to expand inside me, and he tensed and stopped. The feeling of him coming inside me with his sister watching was so hot that I exploded too. I spurted clear across onto the carpet with my first shot, then all over the sheet on the table. My body felt like someone was draining all of the energy from it through my feet and into the floor. I heard an exclamation from a soft female voice, and knew it was Vanilla.
"Fuck!" Shouted Mike.
"Geeze." I replied.
He was leaning forwards onto me with all his weight. I asked him to move, and he took his penis out of me slowly. I felt empty again after it had left. It was a lonely feeling. I lay panting after my orgasm, and heard Mike fall to the floor.
After the feeling had passed and I could feel the stickiness of cum on my chest and the slight sheepishness which had followed all my sexual encounters, I stood up. My bumhole felt sore, but I was glad Mike had taken my anal virginity. Vanilla was standing there looking flushed and very excited. I could smell that she was wet. She kissed me on the lips, reaching back to pat my bruised bottom.
"That was fantastic, Charlie. Amazing. That's gotten me so hot. Thank you. Now you'll get your reward. I'll seduce JJ. Even if I get caught, it's been worth it..."