Chapter 1

My name is Simon. I guess it all started when I was 13. That's when I met a sixteen year old boy named Kevin. We hit it off good and soon became good friends, and then best friends. We even call each other "Bro" affectionatly. He was already a good looking guy when I met him, but as he grew he became muscular and handsome. Meanwhile, I ended up being fairly androgynous, with a slender body and a pretty face that belonged to a girl. The fact I like to wear my hair long doesn't help.

It is a few days day after I turn 18 when something happens that changes the course of our relationship.

I stay late to do some soccer pratice and am just finishing up in the shower. While in the middle of toweling off, two boys come in. They call themselves Butch and the Skeleton, a couple of thuggish bullies who've been held back at two or three times. It looked like they'd been drinking and doing drugs again.

"What do you two want?" I ask them in annoyance, having suffered at their hands before.

They exchange a sneer.

"Look, Skelly," Butch says. "We looked out and found cute girl fresh out the shower."

"HUH?!?"

My heart skips a beat as I realize what is happening. I open my mouth to scream, but Butch tackles me and covers my mouth with his hand. Skeleton gets some towels to bind my arms and gag me. The towel I have wrapped around my waist is removed and I'm completely exposed to these drunk perverts. I shout through the towel in my mouth as loud as I can. Butch slaps me.

"Shut up, bitch," he growls.

"Hey Butch," Skeleton says with a frown. "This girl's got man bits and no boobs!"

"So? Just look at that ass? You think a guy would have one this good?"

He rubs my buttocks and whacks it a couple of times, making me whimper.

"And just feel that skin. Ain't no boy with skin this soft. Rub her chest."

"But it's flat!"

"So? Don't mean it ain't good to touch. And girls with flat chests are supposed to have more sensitive nips!"

He proves his point by pinching and twisting my nipple, making me cry out.

"I guess you have a point," Skeleton says. "But where are we supposed to fuck her without a vagina?"

"That cute school girl ass, dummy. Plus, just picture your dick in that pretty mouth."

Butch hands me to Skeleton so he can drop his pants. But before I can be ass raped, someone come into the locker room.

"Hey bro, what's taking so lo—"

His eyes bulge at the sight of me naked and bound & gagged with towels and Butch with his pants on the floor. The bully opens his mouth to explain, but doesn't get the first word out when Kevin sails into him with a punch. Between his one physical skills and taking them by surprise, he has the bullies knocked out in less than a minute. He unties me and gives me my clothes back.

"Thanks Bro," I tell him with a grateful smile. "I-If you hadn't shown up..."

"Don't think about it," he tells me. "All that matters is that you're okay." He turns to the two bullies. "I think we need to teach these dipshits a lesson..."

We take them to the girls' locker room, strip them naked, bind, gag and blindfold them using towels, tape and even strips of cloth from their own clothes and leave a note saying "We've been very bad. Punish us!". We leave as they come to and start to struggle and "MUPH!". They would never bother anyone again, but that's another story.

Kevin takes me home.

"Listen, li'l bro," he tells me in a concerned voice. "If you need to talk or do something to cheer up with, just call me, okay?"

I nod with a smile. "Okay. But I'm fine. Really. Everything turned out all right in the end."

He looks at me in relief. "That's good to hear. But if you need someone to talk to or a shoulder to cry on, I'm here."

"Thanks."

It's later that night I have a dream. I'm once again being attacked by Butch and Skeleton. But this time they use ropes on my arms and my mouth is covered with tape. And...I...I'm a woman. I'm the same from the neck up and even have the same body type, but I have vagina and mid-sized breasts. Once again I scream through my gag, but this time I am fondled and fingered. And as before, Kevin comes to my rescue. I thank him by...kissing him. After the bullies have been restrained, I thank him even more...

It's at this point I wake up, gasping. I am covered in sweat and...my dick is rock hard. It feels like I've avoided a wet dream. With my parents, who are sound sleepers, in bed, I go into the bathroom. Before I can stop myself, I plop a washcloth into my mouth and masturbate as I images of buff, handsome Kevin and the feel of being restrained run through my mind.

I come and clean up the mess. When I'm done I look at myself in the mirror. I've often hated that I turned out androgynous, but for the first time I think about good I could look in women's clothing...and wonder about how it would feel to be tied up...

Over the next few weeks I find myself drawn to the world of bondage. I look it up on the internet and am fascinated (and at times disgusted) by what I see. I also start picturing myself in the clothes worn by women I see on TV or by women I encounter. The good news is that I'm still attracted to women.

It's Kevin, who is the big brother I've never had who I have new sexual attraction for. I had always admired and respected him and found him attractive (as did everyone who saw him, so it's not just me). I'm not sure if it's love or sexual infatuation, but my feelings for him change and strengthen. I start imagining myself tied up for him to do with what he will. I fell guilty and a little disgusted with myself, but I can't stop thinking about.

Kevin notices something is on my mind and after about a week finally confronts me.

"Simon," he tells me, "you've been acting funny lately. Is it about what happened?"

I squirm some. I'm not a very good liar and I've never been able to pull one on Kevin. I sigh.

"Kinda. Ya see, it's like this..."

I tell about the new, strange things that have been going through my head recently. I'm worried this will creep him out or drive him away. But he listens quietly and when I'm done he seems to study.

"I'm really sorry," I tell him. "I've been trying my best not to think about it, but it keeps coming back to me. I guess you think I'm some kind of perverted freak, huh?"

He puts his hand on my head to pat and smiles. "Nope. I get it. I'll even let you in a little secret: I play bondage games from time to time."

"Really?" I look him over. "But...you don't seem like someone who's into bondage."

"Thanks. I'd say I use it moderately. It's good for a thrill and really livens things up."

"Would you...tie me up and do things to me?"

"Yep! And I mean that as a compliment. When we first met you were so cute. And now you're downright pretty. I've even thought about me and you, but didn't wanna risk our friendship."

"Wait...you've thought about...us?"

He nods. "It's crossed my mind. And in case you're wondering, I'm bi. Though I have standards for men that a lot of guys don't meet very often."

My face flushes, but I smile. To think someone I care about so much feels the same as I do. The fact I meet his standards also sounds nice.

"W-When should we..."

"How about this weekend? Remember how you've been talking about seeing that band you like that'c coming to the city? Well, we can go see them and have some fun at the hotel. May even take in a movie while we're at it and eat somewhere special."

I nod. "T-That sounds just fine."

"Would it be okay if I bought someone else along?"

"I think so, if you have it under control."

"Oh, I do. You let me handle everything."

We exchange goodbyes. I check the calendar and my heart is already racing. Too lose my virginity (well, my anal one) to someone I like Kevin sounds like a dream come true. And the idea of him tying me up gets me even more excited. I can't wait until Friday night…


Chapter 2 (added: 06/17/2011)

The weekend soon arrives. Kevin brings along his latest girlfriend, a hot blonde named Jenny. We drove for a few hours and checked into the hotel.

"Okay, Li'l bro," Kevin says to me. "Bondage or supper?"

"I guess get something to eat first," I answer. "And what about—"

"I'm Master Kevin's slave as well," Jenny says with a big smile.

"I told you," he frowns at her. "Don't call me 'Master'. There are way too many men who'd rather be called a title than their name out there. And I'd rather have a girlfriend than a slave."

"But I meant it loosely," she says. "and you're the best master I've ever had."

"Best?" I ask.

"I had some boyfriends who liked to tie me up," she explains. "But they didn't satisfy me the way your Bro does. A couple of them even hurt me." She snuggles up to him. "His interest in BDSM is moderate, but he has a lot of skill both as a master and as a lover!"

"I try to please," he smiles.

We get a quick bite and go back to our room.

"Okay," Kevin announces. "Time to stip!"

He and Jenny practically leap out of their clothes at an astonishing rate. It's like standing before a pair of naked gods. I strip hesitantly with a face red. And even when I'm in the nude I cover my my privates with my hands and shake.

"It's okay, Simon," Kevin tells me in a soothing voice. "If you don't want to, that's fine."

"I-I-I want too," I tell him. "It's just that I'm a little nervous. And my body isn't as good as either of you. You both have bodies that are the apex of your genders...and I have a body like an ugly cross between a plain man and woman!"

I feel like I'm about to cry when Kevin approaches, emrabces me and gives me a big kiss. A wonderful sensation travels from my lips to throughout my body and I relax in his muscular arms. Our mouths, momemtarily connected by a string of drool.

"Feel better?" he asks.

I nod.

"Good. You shouldn't feel ashamed of how God made your body. The way I see it, you're an interesting cross between male and female. I can enjoy you as either depending on my mind set."

"Thanks, I think."

"Welcome. Now how about we get started?"

"Okay!"

I am made to lie on my back on the big bed and am tied spread eagle with my limbs tied to each corner of bed by soft rope. A red ballgag goes into my mouth. Kevin asks if I want to be blindfolded and I shake my head. I want to see this.

"First," Kevin tells me. "A real treat. Jenny, get him hard for me please."

Now wearing a nice looking collar, Jenny crawls into the bed and takes my cock in her hand stroke it. The next thing I know I'm the hardest I've ever been.

"Wow," Jenny comments to Kevin. "He's almost as big as you, Master. And he's already so hard!"

"Continue. Let him experience pleasures he's never known before."

She masturbates me and fondles my balls, performs wonderful fellatio, puts my member between her big, soft boobs to titty fuck me. It feels so great! I moan loudly and shout through my gag and struggle in my bounds at the new sensations in my most sensitive place.

"Nice," Kevin says, playing with himself as he watches. "Your skills never cease to impress me."

"Thank you, Master!" she chirps.

"MMAGH!"

"Sounds like Simon likes it too," he chuckles.

"How long should I do this?"

"Until it looks like he's ready to come. Then I take over."

So she pleasures me in various ways for about half an hour before I feel like I'm about to pop. Kevin notices and has her stop to take her place.

"Hold it in for as long as you can," he instructs me. "But when you can't take it anymore, climax."

He puts his mouth on my dick and starts sucking and licking. It...it feels great! I'd never thought much about being sucked on by a guy, but it feels as good as when Jenny did this. I scream through my gag and thrash as I try to keep from spurting. But when I can't take anymore I erupt, coming harder than I have in my whole life. Kevin swallows every drop of my semen and even licks me clean. I go limp, half conscious and seeing spots.

"Not bad," Kevin comments as he smacks his lips. "You taste pretty good, Li'l Bro. You okay?"

I nod.

He unties me from the bed only to put the rope on my wrists, elbows, ankles and knees and putting a little plug in my anus. He gives me a little peck on the cheek before turning to Jenny. "I believe you deserve a reward..."

She is soon bound, gagged and blindfolded, moaning through her gag as Kevin gropes, fondles, rubs, pinches, licks, sucks, nips, and kisses her all over before fucking her in several positions, sometimes gentle and sometimes rough, to make her give muffled yells that sounds surprisingly good to my ears. I even get hard again watching these two beautiful people go at it. Jenny even fainted when she came, going limp as some of Kevin's sperm oozing out of her cunt.

Kevin pulls out of her and removes the blindfold, kissing her on the forehead. He picks me up to carry me to the bed. He sleeps with his arms around us, my head on one big pectoral and Jenny's on the other. He rubs our hair.

"This trip is off to a great start," he says with smile. "And tomorrow I have some big plans for us, my angels."

I moan and nuzzle him, drifting off into a deep, peaceful sleep as I think about what lies ahead.


Chapter 3 (added: 06/17/2011)

I sleep surprisingly well for being bound and gagged. Kevin already up and even dressed by the time I awake with Jenny untied and in the shower. He unties me.

"Today we're going to try something special," he tells me. "I want to try something out."

"What?" I ask, both intrigued and nervous.

"Well...you've been thinking about dressing like a girl. So I thought we could try it out."

I gasp and stiffen.

"If you don't want to—"

"I-It's okay," I tell him. "It just startled me...you really think I should?"

"Won't hurt to try. You can see how much you like it or not. At the very least we'll get it out of your system."

I nod in agreement. After Jenny gets out of the shower I take one. When I come out I see a lovely dress laying out before me. But before I can put it on, they put a little tube thing on my dick to keep it small and flaccid and take the butt plug out for a bigger one. They also smooth down my balls with duct tape. I have to wonder how transvestites put with this and have some new respect for them. But I like the feel of the panties on my thighs and butt. They even put me in a bra and pad it with tissue paper. I put on the dress and Jenny puts some make up on my face, applies some hair care products, and even ties my hair into a short ponytail. When she is done I see a gorgeous young woman looking back at me in the mirror.

"I-Is that really me?" I ask in astonishment.

Kevin and Jenny nod. "You've always been kind of girly," Kevin says. "Though some good make up helps too."

I stare at my reflection, unable to believe how...good I look.

"How long should I stay like this?" I ask.

"As long as you want," Kevin replies.

"But we shouldn't stay cooped up in this room all day."

"And what's wrong with you going out like that? I think it would be fun to see how many could tell if you're a guy or not. You could be the quiet, innocent one while Jenny would the sultry temptress. It would be the best of both worlds!"

I look back into my reflection. Trying to pass myself off as a woman and fooling people sounds exciting.

I lick my lips in excitement.

"Okay...but what about when I have to go to the bathroom?"

"We'll look out for porta-potties and places that aren't too busy."

"What about when I need to talk?"

"Throw your voice. I think you could have a good girl's voice with enough practice. Maybe some gargling to help your throat and vocal cords..."

He and Jenny gets dressed and we go out.

It's so exciting. Most people actually think I'm female without a second thought. A few people even compliment my appearance, using words like "cute" and "pretty". One guy even tells Kevin he's "one lucky bastard" seeing his arms around me and Jenny.

We have lunch, go to a movie, do some sightseeing and shopping, go back to the hotel room to freshen up, rest and for me to use the bathroom and get an even bigger butt plug, then go to the concert. A good time is had by all. And the entire time no one realizes that I'm a pretty boy in women's clothing...

When we get back to the room that night, Kevin asks if I want to play some more.

"You bet!" I say as I bob my head. I blush as I add. "And this time could we...do it?"

"I guess so. I kinda wondered if we could deflower you on this trip. If you want to, of course."

"Of course I want to!"

"That's the spirit!" Jenny cheers me.

We all strip (and the plug removed from my anus) and my arms are tied behind my back while Jenny's hands are cuffed in front of her. We kneels in front of Kevin to give a "double" blow job. I kiss his "little head" a few times before tentavively licking his shaft. I hesitate before taking him into my mouth and carefully sucking him.

"How am I, Bro?" I ask after minute or two. "I'm not doing it wrong am I?"

He shakes his head and smile kindly. He rubs my head. "You're doing just fine. Just go with what feels right to you. And don't worry; bad beejays are very rare. So just do it how you want and I'll enjoy it."

Felling better, I continue and suck and lick with more confidence. He tastes so good...Jenny joins me, licking one side of his dick while I do the other, or sucking the shaft while I work on his balls and vice versa. We exchanged several pecks and licks on the cheek and forehead After a while he tells us to stop.

"What?" Jenny asks, "You don't want to come in out mouths and on our faces?"

"Not this time," he says. "I want us all to come at once. Here's how we're going to do it..."

Jenny is gagged, blinfolded and tied spread eagled on a bed. My arms are untied and repositioned with long cuffs on my wrists. I quickly realize what's happening. I take her big, beautiful breasts in my hands and play with them. They're so soft and jiggly. I lean over to suck and lick her nipples and she moans in pleasure.

"That's it," Kevin cheers me as he rubs himself. "Enjoy that wonderful body."

I play with those wonderful boobs for a while before turning my attention to her pussy. It's already so wet. I run two fingers over it and hold them to my nose. It's the greatest thing I've ever smelled. I start licking it and it's one the best things I've ever tasted too! I lick and finger vagina and kiss and suck on her clit. She squirms and groans beautifully in ways that signals she likes it.

"That's my little bro," Kevin says proudly. "When she gets nice and lubricated, give her a good hard fucking. She likes that."

When we're both ready, I put my hands on her waist and start to ease myself into her. It feels so good as my penis slids into her warm, wet pussy. It even feels...great, when my cheery pops. I start out slow and careful, but build up force as I get more into it (both ways).

"Can I come in her, Bro?" I ask. "Please?"

"When I'm ready for you to. Which won't be long. Now get ready, because here I come!"

He makes me temporarily stop fucking Jenny and rearranges us. I'm gagged, my hands are cuffed behind my back and I'm made to sit on the bed. Likewise, Jenny's arms arr bound behind her back to. He tells her to spread her legs and picks her up to reinsert me into her. She wraps her legs around me as I pick up where we left off. Kevin removes the butt plug and sits down behind me. He puts his hands around my waist and picks me up.

"I used those plugs to widen you for my entrance," he tells me. "But this will still hurt. I'm sorry about that."

I gasp at the feel of his dickhead going into my spincter. But as more of his cock goes in, it doesn't hurt as much as I thought it would. Though I can't help but yelp through my gag, tense up and shudder when he deflowers my ass. He makes me feel better by rubbing my chest and playing with my nipples. I had felt guilty about having the flat, useless chest of a male, but Kevin is shows me that you can do things with it too. I moan at the sensations in my pecs as he kisses me on the back of the neck.

"Is it good, Simone?"

"YEGH! UGH GAGH YEFH!"

"Glad to hear that?"

He fucks me from behind while I fuck Jenny. We're in a beautiful rhythm as our bodies move to to match our passion.

"CUGH I CGMM?" Jenny moans throw her gag. "PLEEGH!"

"MUGH TGH" I mumble.

"Not just yet," he tells us. "Wait for me. I'll come very, very soon."

A few minutes later he says "Now! NOW-WWWUUUGAGHHH!"

"MMUURRGGHH!"

"MMAAAAUUGGGHHH!!"

Kevin's jism goes up my ass while mine fills Jenny's pussy. He falls backwards and I am sandwhiched between his hard pecs & abs and Jenny's big soft tits pressing my chest. I feel light headed and weak, but with a funny tingling sensation that feels good. Kevin ungags us to let us catch our breath.

"How was it?" Kevin asks me.

"That...that was perfect, Bro! I never thought my first time would possibly feel so great." I start crying a little. "Thank you. Thank you both so much!"

Jenny kisses me and lick the tears away. "Welcome, sister-brother slave."

"And how would you like to experience this kind of thing all the time?" Kevin asks me.

"I'd like that."

"Good. I was thinking you could move in with me and be my live in slave. It would be nice to have a sidekick and you're already pretty helpful."

I nod with a smile. "Yes. I promise to be the best slave I can be. I'll do whatever you want me to."

He chuckles. "You don't have to go that far. I told you, I use the term 'slave' loosely. You can do what you want. You don't even have to meet any condition to be tied up. Just say so. Heck, vanilla sex works good for me."

"Okay, Bro," I sigh happily. "You know me. I'm not hard to please either."

"Good. And just wait 'til you meet my other 'slaves'."

"How many do you have?"

"You'll find out. I have a whole secret life you didn't know about but are about to be a part of. Glad to have you!"

I smile as relax my body and start to drift to sleep, dreaming of my new life with Kevin and my fellow slaves...