My name is Sam, I was raised in a fairly well off family, classic middle-class suburbia. We live in a single story, 4-bedroom house. The master bedroom is in the back corner, my sister’s bedroom right next to theirs, my bedroom, which is directly across the hall from Tammy’s, and a spare bedroom, across the hall from my parent’s room, which acts as a guest room/ study room. My parents don’t go away often but when they do trouble usually ensues. I have an older sister named Tammy; she is, at this time, 16. She has long wavy light brown hair, blue eyes a fair B-cup, standing at 5’4″ and slim from doing gymnastics and other activities during middle school. I’m 14, freckled ginger brown hair with the same waves and I wear my hair long (for a guy), blue-hazel eyes, a little chubby, but taller than my sister at 5’9″. My secret from the family is that i cross-dress. I will steal my sister’s thongs, dresses, and other articles of clothing from time to time try them on, jerk off in them, stick them in between my mattress and box spring, and when I’m done having my fun with them, I’ll rinse them off in the sink and shove them at the bottom of her dirty laundry, hoping she won’t suspect a thing.

When our parents are not on a trip, things are generally very calm. My sister, being pretty and flirty, will have boys over every now and again when my parents aren’t home yet, and she will mess around with them. I often will sneak around back and peak in through her window and watch her give her boyfriends blowjobs, I particularly like seeing when they cum on her face or in her mouth and she shows off her swallowing ability. She hasn’t had vaginal sex yet so she can claim to be a virgin, but that’s alright, because she uses this to justify anal and oral sex. I remember one time when she was going down on one of her boyfriends, and she started stroking his cock, then sucking and licking on his nuts. She then proceeded to move more south. The guy jumped a little but she placed her hand on his tummy soothing him and she grabbed behind his knees pushed them up to his chest, where grabbed hold and she started tossing his salad. He seemed to really enjoy that; I then became very curious as to what they hubbub was all about.

So one summer weekend, my parents announced they were going to the next state over to visit Grandma. There was a family reunion and we protested going. My parents, figuring Tammy was old enough to take care of me, placed that condition, and to her dismay and my glee, it was set, and they were off the following morning.

I rose up early the following morning and played videogames and ate my froot loops, and when my sister came around it was mid morning. She was wearing a big t-shirt and some pink cotton brief panties, with a yawn she exchanged good mornings and she proceeded to brew up some coffee. She had herself a cup and then announced to me:
“Hey, I’m planning to throw a party tonight. Don’t tell mom and dad, and I promise it’ll be a good time for you.”
I was super excited, I loved hanging out with my sister, aside having a boner for her; we also had a lot of fun. I gave her my “scouts honor” and she prepared the house, putting away the fragile decorative and expensive items and locking it in my parent’s room. She then started sending out a blanket text telling all her friends to bring booze, weed, and everyone they knew.

By the time the party started things were really getting kind of out of hand. It’s a good thing Tammy put away the breakables, because it was pretty hog wild. I decided, to give myself a little edge, I was going to wear one of the thongs I had pinched from her drawer, and that gave me a pick-me-up for confidence. I got a lot of compliments having never met my sister’s beautiful girlfriends, and the guys were more or less happy to entertain Tammy’s kid brother.
There were probably about 50 in attendance that night and I’d seen Tammy go into the back bedroom with several different guys at a time and I knew she was sucking their cocks and swallowed and got sprayed with their cum, but she cleaned up well enough for the next cock. I had eavesdropped on conversations about Tammy being a blowjob Queen, I had no idea though; and with every cock she sucked and every load she swallowed, with her friends’ help the party dwindled down. I was super horny.
I had a lot of firsts that night… First time drunk, first time high, first time…
“Sam, what’s this?”
“What’s what?” I asked
She came up behind me, holding one of her thongs that she found in between my mattress and box spring… “Shit, I must’ve not stashed it away, didn’t I put it away, and close my door?” I thought.
I shrugged knowing full well I was caught.
“Where’d you find it?” I asked her.
“Well, me and Fred, here, took a peak in your room as my room is occupied and mom and dad’s room is locked, so we were going to have a little fun… I noticed it on my way in. Have you been stealing my panties?”
My sister has a loud voice to begin with so by this time most everyone was staring in our direction with cheesy little grins on their faces.
“I… well… uh…” I stammered looking for words
Then one of her friends came up behind me, and got to the back of my pants revealing one of her thongs and screeched in glee.
“He’s wearing the thong I bought you for your 16th birthday!” Her friend explained giggling.
“Is that so? Well Fred wondered if you might be into guys, being that you want to dress up as a girl.”
I was at a loss, and very confused, being very drunk, high and scared.

She gave a wry grin and gave me a proposal.
“I imagine mom and dad don’t know about this?”
I shook my head ashamed and dumbfounded.
“I’ll make a deal with you. You do whatever we tell you for the rest of the night and this will stay between us, and mom and dad will never know.”
Not having any place to go except into mortification and ridicule, so I took the alternative, and nodded my head in agreement.
I felt a little relieved but at the same time all her friends now knew, and I began scanning the crowd, there were only about 15 people, about 8 girls and 6 guys plus myself, it seemed like a lot more.
She noticed my worry.
“Don’t worry, Samantha, we’ll take good care of you.”
“Samanth…?”
Before I could finish my inquiry all 8 girls rushed me into Tammy’s room which has now since been evacuated from the previous occupants. They tore off my clothes, leaving the panties on and matched me up with the bra to make the set. Stuffed it with some inserts that my sister uses to make her boobs look bigger, and was fed another shot of whiskey for being such a “good girl”. Weed and excited chatter filled the air, I gotta say I was really getting turned on by being touched by so many women at once, most especially when my sister would get her hands on me, that’s another first for me too, never really thought of Tammy that way.

The same friend that exposed my thong really has a knack for stating the unnoticed, because next thing you know I hear,
“She’s gotta boner, Tammy. Whatever shall we do?”
All the girls giggled, and they each took their turn making sure to give it a good feel up before moving on to the next task at hand.
When all was said and done, they had me masterfully in full makeup, eye shadow, mascara, bright red lipstick and lip gloss, blush. They had my hair flat ironed and sultry, they picked out a cute little blue dress that really made my ass look, surprisingly good and stilettos that my sister had worn to last year’s Halloween party, that my parents didn’t know she had.
All the girls circled me and gave approving nods, then shuffled me in front of the full length mirror…
If I didn’t know any better, you would never have known that I was a guy.
“Damn Tammy, why is she prettier than I am?” this comment released a fit of giggles, and I was in awe just looking at myself. Until I was unceremoniously grabbed and shuffled to the “display room” as they were calling it.
All the guys who were there were just as dumbfounded as I was. They must have been expecting some hideous ridiculous outfit with smeared make up and outlandish bright blue eye shadow, expecting a good laugh… not a character that made them question their sexuality. Everything went silent…
“samantha… Samantha… SAMANTHA!”
Tammy riled me out of my stupor.
“Are you ready for your treatment?”
I nodded compliantly.
“Ok, first, go in the middle of the circle and do a couple twirls for us.”
I obliged, and I gotta few cat calls from all in attendance.
“Second, flip up that skirt slowly and show off that ass”
As I flipped up my skirt, with each inch the gasps were more and more audible as my sister’s sweet sixteen black thong was revealed, loud cheers and applause followed.
“Jimmy, come here and sit in this chair.” Jimmy came over and I didn’t know what was going to happen, or did Jimmy.
Smilingly, “Jimmy, here, has never had a blowjob. Tonight, that is going to change. Samantha, initiation into girlhood is sucking a dick and then swallowing their cum—you will do this tonight.”
I began to protest, but she stopped me and reminded me that I agreed to “anything”.
I hesitantly approached Jimmy and slowly got down on my knees in front of him. I gave one last pleading look at Tammy, but her eyes said “there is no getting out of this.”
I began to unbuckle Jimmy’s belt and undo his button and zipper, and then one of the girls came and pushed my dress up exposing my thong. I grabbed jimmy’s pants by the underwear band and he stood up to assist the process. My eyes were down and I when I came back up his heavy dick hit me on the top of the head and then poked my forehead. “They look a lot bigger when it’s someone else’s” I thought.
Jimmy sat back down, and gave me a wry grin. I grabbed hold of his dick at the based and having watched my sister do this so many times before I mimicked what I remember seeing her do. I stuck the cock as far in my mouth as it would go, closed my mouth on it, and sucked it slowly until I got to the head then back down and up again bobbing my head while shifting my shoulders around to get a better angle on it. Rigorously but not quickly I sucked his cock, putting my best effort into it. The crowd cheered me on as I bobbed and licked, sucked and slurped. I was really getting excited and encouraged.
Then I remembered her magic trick, I started sucking on Jimmy’s balls and worked my way south and propped his legs up and started licking his ass, the musky tight hairy ring wasn’t as bad as I thought. I heard Jimmy moaning so I licked with more gusto. With a loud slurp I caught my breath and went back to his cock, playing with his balls with my hand, and Jimmy warned me he was going to cum. Remembering what Tammy said, I just finished strong and swallowed blast after blast of Jimmy’s cum, it didn’t taste as bad as expected and kinda understood why Tammy does this. The look on Jimmy’s face was priceless. It was the look of pure ecstasy.
When I looked up at everyone around me, the crowd was silent and touching themselves, there was a sexual tension in the air that was tangible. Everyone suddenly burst into loud applause and Tammy, after everyone settled down started asking for takers on who is next.
I sucked off four more cocks and the girls too care of the rest… I was spent… and strangely satisfied.
Everyone went home giving me a kiss on the cheek or slapping my ass, and it was just Tammy and I.
Tammy and I just looked at each other for a moment taking in the surreal gravity of what just happened, until Tammy spoke.
“Look, things got a little out of hand, I didn’t mean for it to go that far.”
“It’s ok, Tammy, I really did enjoy myself.”
“You did? But we humiliated you, you still are dressed up as a fuck slut.”
“ I didn’t know I was going to enjoy it that much.”
Tammy looked at me kind of sheepishly…
“Sam,” referring to my actual name, “can I…”
She stopped suddenly.
“can you…yes?”
“Well, everyone else was touching up on you and I got so hot and bothered and frustrated that I couldn’t do anything, I think you look totally sexy and I’m sorry for what I did and I wanted to make it up to you.”
“how do you intend on doing that?”
“well…”
She walked towards me and gave me a little coy grin and began to undress me.
“What are you doing?” I asked
“Shhh… final command…”
She undressed me down to her thong and then told me to undress her down to her thong. And there we were standing in our thongs facing each other.
“Sit!”
And oh how I sat. She got down in front of me, and with as much love, gratitude and lust she could muster she swallowed my cock whole, and didn’t give it back. She was going up and down and slurping and gagging. She took me all the way down her throat, which wasn’t terribly difficult for her being that my cock was smaller than what she was used to, but she didn’t point that out. She gave me all the wonders of the blowjob queen, and even gave me a rimjob for five whole minutes. She went back to work on my dick and got it super wet. And then she turned onto the couch.
“for my final instruction, fuck my ass then cum in my mouth”
I was flabbergasted…
But I complied, it was at this moment when my sensibilities came back and the realization that my sister just pleasured me orally and I’m about to have sex with her ass…
…life is good…
With my dripping wet cock I shoved it in with easy and had a great time, feeling her sphincter rings and ass hairs tickle my cock, feeling her pillow soft ass to cushion my thrusts, it wasn’t going to take me long to cum, and as I was about I pulled out and she turned around got on her needs in front of me and opened her mouth. One, two, three, four large cumshots flew towards her face most going in her mouth but the first one streaking across her right eye into her hair and trailing down her nose. She swallowed my cum, and then wiped the access off with her finger and sucked her fingers clean.
Tammy told me that she knew I watched when she was sucking her boyfriends cock, she’d seen me in the window, she knew I cross-dressed and knew I’d been stealing her panties being the panties would be soaking wet at the bottom of the laundry basket, that’s why she set this up, she wanted to see just what kind of freak her little brother was.
We showered and slept holding each other in the master bedroom. We cleaned up the house and reordered it to its original state as when mom and dad left, and when they got home, they didn’t suspect a thing.

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