Truth or Dare Takes a Turn Pt. 01

I'm sitting at home on summer break, just a few weeks after graduating high school. I hear my phone buzz and glance over to take a look. I can't believe what I'm reading! "Luke Elwood has invited you to his event: graduation celebration party tonight at 8pm."

You see I was never really one of the cool kids in high school - I never really had any friends but I was never one to be bullied, just not really acknowledged. I flew under the radar - worked hard, got good grades, that kind of thing - not the kind of guy that was invited to any parties really, especially not Luke Elwoods parties - the coolest kid in school! So this message came as quite a shock to me, I guess he must have just invited all the grad students.

My name's Riley, I live in Sydney Australia and I'm just an average guy who's just finished high school, there's really nothing that impressive about me - I'm 18, about 5'8, slim but not really athletic, I work out to stay healthy but don't really spend much time at the gym. I have a good work ethic but never really rose to the top at anything I do - I've just kind of sat in the middle of the pack my whole life.

It gets to about 7:30 and I take a shower and start to prepare myself for the party of the year, agonising over every decision and detail to make myself look just right. I settle on wearing a pair of ripped black skinny jeans and a light blue tie dye v neck t shirt, I comb over my hair that's getting a touch thicker and longer than I like but is still manageable and I tame it back into a sleek looking style. I shave and trim and perfect the look before jumping in my car and driving myself to the party. I arrive at about 8:30 and the place is already packed with people. I plan on checking the place out, seeing if there was anyone I knew that I could chat to and then leaving after an hour or two.

A few minutes after I arrive, a couple of really hot chicks who are clearly already in college come over and start chatting to me, asking me about myself and offering me free drinks - how can I resist! So I start downing drinks and chatting with them, after that there are more chicks that want to get to know me. This party rules!! The next time I look down at my watch it's already 1:30am - I stand up to leave but realise that I had drunk a lot more than I planned on and probably shouldn't drive as everything started looking super blurry - I had never been drunk like this before. I head inside and flop down on a couch in the living room to pass out and sober up.

Just a few minutes after, as I'm ready to pass out, the door from outside busts open and the room is filled with a sea of drunken laughing and screaming. I look over and see 5 guys sitting on the floor in a circle. I can't make out who they all are but I can definitely tell that one of them is Luke Elwood. I must have been staring a bit long because Luke spotted me and yells out "Hey Riley - crashing so soon? We're just about to get into a game of truth or dare - want to join us?"

My head is scrambling - I am feeling more drunk than ever before but Luke Elwood has asked me to join a game of truth or dare - this could be fun, getting to hang with the cool kids for once. I decide to join their game. As I go and join the circle I see that the others in the circle are Brent, Leroy, Sammy and Tony. The other 4 coolest kids in school.

The game starts pretty innocently with a lot of truths being shared and slowly progresses to more body parts being displayed, some kissing and groping, and a few lap dances, stuff that usually would seem weird and off limits if we weren't so drunk but seemed a lot more acceptable in our current states.

Then it happened - the question that changed everything for me.

Tony asks me if I have ever wanted to try on girls clothes and try living as a girl, even just for a few days? Without thinking I blurted an answer "Sure I have - I mean it'd be pretty hot right" I would never have answered that way another time but my inhibitions are way down and it just came out. Clearly this wasn't the answer the guys were expecting as their faces were a combination of shock and a smug sort of smirking at my response.

The game continues for another couple of rounds and no one really mentions my earlier response, until Luke asks me for a truth or dare. I choose a dare - not wanting my brain to betray me again on a trick question. Luke has clearly seen an opportunity in my earlier answer to have some fun as he dares me to go into his sister's room, who is a year older than him (19) and away at college, and swap my underwear I'm wearing with the pair of her underwear that I think is the sexiest.

I wasn't expecting this kind of dare and drunkenly protest for a few minutes before finally giving in and going to do it. I walk in to Luke's sisters room and over to the drawer Luke had told me contained all of her underwear and started rifling through it, picking up plain panties, patterned panties, the odd thong until I get to the bottom section of the drawer and find an array of super sexy lace and satin panties and thongs.

I wade my way through the seemingly forbidden garments until I find a little pair of black lace panties with a pink lace waistband and a little pink satin bow at the front. These are the pair, I decide as I'm peeling off my skinny jeans to replace my comfortable boxer briefs with these sexy little panties from Luke's sisters wardrobe. I quickly put them on, put my jeans back on and head back out to rejoin the game.

As I rejoin the game, no one says anything about my dare, we just continue on playing, until a couple of rounds later, Brent dares me to go back into the room and put on the bra that matches the panties I chose along with a pair of pantyhose I think look sexy with my underwear selection. I go into her room and find the matching bra and a pair of pink fishnet pantyhose, before again returning to the group. Once I return I notice a different feeling in the room, something had changed.

I soon found out what, as every turn the other guys took, they used to dare me to wear more of Luke's sisters things and make me continue to dress up. First it was adding oranges to my bra then it was adding lipstick, then painting my nails, then more makeup and shaving off all my body hair, they then dared me to remove my pants and t shirt so they could see what I chose to wear. This was super embarrassing because the panties I had chosen were very revealing and all of this playing dress up had me rocking a massive boner, which my panties could barely contain.

When I remove my clothes the guys start cheering and wolf whistling and at that moment Luke, who no one noticed had been missing, re-entered the room. We went back to the game and I dared one of them to strip to their underwear and do a sexy dance, thinking it would be funny but it didn't compare to the things they make me do.

Luke then gave me a dare and pulled a few things out from behind his back. The first of which was a pair of pink stilettos with a 5" heel that he makes me slide onto my feet. Then he adds a reasonably thick petticoat, which I had no idea of what it was until Luke told me, and then finally he hands me a frilly pink french maids dress which he says his sister wore one year for a school play. I put the dress and petticoat on and think things can't get any worse, when Luke pulls one last thing from behind his back and says "ok guys let's get to work." Before I know it the 5 guys are all coming at me, and all I can see is hair in my face everywhere and a stabbing pain running through my entire body.

A couple of minutes later they step away and I realise they've given me hair extensions which actually match the natural colour of my hair quite well and with me not having had a haircut recently it also blends into my hair quite well - making it look very real. As I run my fingers through the hair they've added to my head, I brush past my ear and feel something hard dangling off it.

The sharp pain I felt was the guys piercing my ears. I also notice something straining on my neck as I turn my head, so I stand up and stumble over to a mirror, not quite used to the heels I'm wearing and falling over a couple of times on the way there, the third time I fall I tried to pull the heels off my feet but I couldn't get them off. That's when I noticed the little silver lock dangling off each of the buckles which I hadn't fastened, but were now fastened and locked onto my ankles.

I can't believe what I'm seeing, still feeling the strain on my neck I forget the locks on my heels and continue stumbling to the mirror, all while the guys are bursting with laughter back over the other side of the living room.

When I finally get to the mirror I can't believe my eyes, for 2 reasons, the first was I actually looked ok and almost could pass for a woman, something I never thought could be true. The second was my neck, I look at my neck and see a 1.5" wide piece of pink leather with diamantes all around it, and at the back, another little silver lock fastening it. They had locked a collar on me - What on earth had I gotten myself into...

Before I get a chance to think on that and make a plan for escape, the guys have joined me over the other side of the room at the mirror where I was standing. They start teasing at my hair and whispering in my ear about how cute I look and what a sexy little sissy boy I am. I'm disturbed by the things they are saying but the thing that gets me the most is they have changed my name from Riley to Ruby, continuously calling me their ruby little sissy boy.

As much as I can't stand the way they're treating me I go along with it and don't protest so as not to make things worse for myself. My lack of protest doesn't change anything though as things get worse for me all on their own when Luke lifts up my skirt to tease me but at the same time notices that my cock is a fully erect 6" inside my panties. He stands up and fishes around in his pocket while telling me that he thinks it's cute that a little sissy like me gets a hard little sissy cock when being aroused by real men.

He follows this sentiment though, as his hand finally makes its way out of his pocket, by saying that he thinks little sissy boys don't deserve to have access to their little sissy cocks. And with that he kneels back down and lifts my skirt and pulls down the front of my panties. I try to resist, having no idea what he is going to do but am held back by the other guys. While I am restrained this way I feel Luke squeezing at my cock and playing with it, whatever he is doing really hurts me and I try to scream out. As I do I hear a little click and feel Luke release his grip.

Still not knowing what he has done, Luke stands up and tells me that my little problem is all locked away nice and tight, just the way a little sissy should be. The bastard locked my cock in a chastity device. I lift my skirt in front of the mirror to confirm my suspicions and see that my cock, now no longer than 2" long is all curled up inside a little pink chastity cage with a little bow on top and locked with a little silver heart shaped lock.

I can't believe what I'm seeing and demand that they release me and let me put my guy clothes back on, pleading that they've had their fun and to let me go.

Tony pipes up this time and says "oh we haven't had our fun yet... we couldn't let the opportunity to enjoy a little sissy boy like you go to waste... could we boys?" The boys all shake their heads in agreement with Tony's statement.

Brent steps in and looks me in the eye and says "ok slut it's time to show what a good little sissy boy you are. We want you to give each of us guys the most amazing blowjob you can and it doesn't end until you can make us each cum with just your sissy little mouth and we each get to decide where we want to dump our cum, got it? Do this for us and we'll let you go." I consider their proposal, something I never thought I would be doing in my lifetime, but if it's a ways out of this mess I wanted to weigh my options.

Before I get a chance to think I am pushed down to my knees and all I can see is Luke's rock hard thick 9" dick staring right at my face, followed by Luke telling me to "Get to work pretty boy, make it sloppy and deep for me babe." I hesitate before I take it into my mouth but Luke notices and grabs my face and forces his giant cock into my mouth. I'm trying to scream and resist but can't make more than a grumble as his cock repetitively slams into the back of my mouth, edging closer each time to the entrance of my throat.

This goes on for a few minutes with Luke force fucking my face, before I notice a strange shift and Luke's hand is gone and I am actually sucking his cock, on my own, trying to let it in deeper down my throat with each thrust, my hands clinging to his perfect ass cheeks as I bob up and down on his giant tool.

Eventually after a few more minutes, his cock is gliding up and down my throat easily and with each thrust my nose is smooshing up into Luke's perfectly trimmed pubes. Just as I start to get used to the feeling of sucking cock, Luke grabs my face and pulls out of my mouth. He pulls my hair with one hand to hold my head where he wants it and with the other hand, strokes his cock a couple of times before unleashing jet after jet of his hot sticky cum all over my face.

I am covered in his man juice and go to wipe it out of my eyes but Luke slaps my hand away and says to leave it there as he shoves his cock back into my throat and tells me to clean his cock. I can taste his salty sweet sperm as I lick and suck his remaining seed and wish that I could cum too right now even though I'm totally disgusted by what I have just done.

Once Luke has slipped his cock back into his pants, Sammy steps up and I service his cock the same way, he is slightly smaller than Luke so his cock slides down my throat a lot more easily. A few minutes in Sammy grabs hold of my head and shoots his seed down my throat, pulling up a bit towards the end so he could coat my mouth with his sticky cum and make me swallow his load. Sammy is followed by Brent who is around the same length as Sammy but much thicker, causing me to gag more as I suck him. Brent decides to let his cum spray onto his feet and he makes me lick it and suck it off his toes and foot which I don't think had been cleaned for a week.

Once I was done with Brents disgusting sperm I moved on to servicing Leroy who is the quietest guy of the group, it turns out has the biggest cock at more than 10.5". I suck him off and when he is ready to cum he pulls out and bends me over pulling down the back of my panties and cumming all over my ass and filling my crack, he also scoops up some of his cum and rubs it all over my caged little cock and makes me suck his fingers and cock clean after.

Finally it's Tony's turn I take his thick 8.5" into my mouth, moving my mouth along his shaft, working it the same as I did for the others but with no sign of him even getting close to cumming as quickly as the others did. After another few minutes he pulls his cock out of my mouth, I get ready for him to shoot his load but instead he tells me to work his large balls. I move my mouth down to his sack and start licking, biting and kissing at his beautiful balls, eventually deciding to take them into my mouth, only to realise I can only fit one of them in at a time. A few more minutes of worshipping Tony's balls and I move back to his cock. This time it only takes me another few minutes before he pulls out ready to blast his load.

Tony also bends my over and pulls down my panties but instead of just shooting on my cheeks and crack like Leroy, Tony grabs my hips and in one swift motion, plunged his massive tool straight into my virgin hole, my ass engulfing his entire cock and becoming filled with what seemed like a never ending stream of his hot, slimy sperm. He pulls out and I'm ready to crash but before I do, Tony slips what feels like a butt plug I to my ass, keeping my ass full of his seed.

I collapse onto the ground and after a few minutes to recover from the whole ordeal which just ended I speak up and tell the guys that I did everything they asked and serviced them as well as I could, and let them cum wherever they want and that it was time to let me go. The guys start laughing at me as I demand my freedom from them. Brent steps up once again "oh we're not done with you yet sissy - this was just the beginning. And you're such a good little cock slut we may never want to let you go."

Luke follows on "you've just given us all the ammunition we need to keep you like this, sissy boy, you just sucked us all of, took our cum every way possible and enjoyed it. And we have loads of photos of you doing it. So unless you want us to expose you for the little sissy you are to everyone you know, you'll do as we tell you ok?"

I defeatedly nod, knowing that they completely had me and there was no way out other than to comply with what they wanted. There was no way I could let anyone else see me like this.

"Go and sleep out on the porch, there's an empty dog kennel with a blanket there if you want it. We'll see you in the morning so you can clean up from the party our little sissy maid, oh and don't think of leaving or trying to escape, and we'll be checking that you're plug and cage haven't been tampered with in the morning too." Luke remarked before they pushed me out the door all left me alone. I sobbed as I heard the click of the latch as the door was locked and I was alone, cold, drunk and dressed as a sissy covered in 5 other guys cum.

To be continued...