Your best friend, Sam

"So definitely be ready when I get there, cuz I have some surprises for you too!" You wonder why his voice is so high pitched and sing song over the phone but quickly turn to more immediate concerns. How are you going to explain this to Sam? Can you trust him to keep his mouth shut? How big do you think his cock is exactly? You are so twisted into knots by indecision and your thoughts are so sluggish and slippery from drinking that the most you manage to find for additional cover is a silk kimono.

DING DONG

You hurry downstairs hoping your excuse is convincing enough to sweep all this under the carpet. Opening the door, you slur out, "shoooo funney shtorey...Ima made a joke...on you hahaah get it?" Sam looks confused...and also cute? He is wearing a rain jacket despite it being a cloudless sky, his long auburn hair which is usually kept in a ponytail is cascading about his shoulders. And he's wearing...make up?

He steps inside, sloughing off the raincoat to reveal the Dr. Frank-N-Furter cosplay he breaks out every Halloween and at the midnight movies and...a lot of things are starting to suddenly make sense to you. "Oh, I'm so glad we can finally dress up together! I've been trying to drop hints to you for years but you never seemed to pick up on them. Oh well, better late than never..." Sam...Samantha? wraps her arms around you and pulls you into a kiss. It's different from Dirk's softer, but no less hungry.

After you spend what feels like an eternity wrapping your tongues together and sucking on each others plump lips while you grind against each other's silken frames, Samantha finally breaks the kiss. "So are we like girlfriends now? Can I borrow your clothes? Can I finally devour that adorable ass of yours? Oh and I prefer Samantha, what should I call you?"

Your mind reels, and not just because of the booze. You try to take it one question at a time. "Call me......Barbie." You don't know where it came from but it sounds right. "An yoo can absholutelee eat my assss, finger my assss, fugg my assss...it's why I call." You can't believe how honestly horny you are being, but you have been aching for it since you fat fingered your friend. "Alssho we shool totally play dressss up. And we can be gurlfriembs and make fucks and go shteady. Shaaay, do you wanna drinks?"

Samantha giggles and takes the bottle of bourbon you didn't realize you were still holding. She takes a deep swig and her face glows gorgeously. "Sure thing, Barbie. I could use a little extra courage for my first time too. But no more for my sexy sissy girlfriend. I want you to remember tonight." She pulls you into a kiss you will never forget. You feel her sissy cock throb against yours...it's not as big as Dirk's but you are sure you will feel it. She feels your sissy clit throb against her and she kisses you harder, instinctively realizing she will have to be the top in this relationship.

You stumble over to the couch and fall in a tangle of lithe limbs, silk encased supple skin, and wet, wanting mouths. Her hands explore you softly, but insistently. She kneads moans and whimpers and coos out of your doughy ass like a beautiful instrument. You almost sob with joy as she slinks around to bury her face between your cheeks, slipping her surprisingly long, thick tongue up inside you and making you realize beyond a shadow of a doubt that you have a cunt in your ass.

You twist around each other again and again. One moment you're freeing her sissy shaft and swallowing it whole, the next your face deep in her sissy cunt. It's less foreplay and more exquisite **** you inflict on other because you both love the sweet suffering, the pleasure so intense it hurts, the ache begging to be filled, the pressure building until you both are ready to explode. Finally Samantha takes another big gulp of bourbon and says, "Lesh go upshtairs an go make fucks."

You stumble up the stairs, giggling and groping the entire way. You lead her towards Brandi's room, it just feels right for your first time. Suddenly as if a switch has been flipped, she is much more dominant. She wraps her lips around yours, slides her slim fingers between your soft cheeks and up your soft cunt and walks you backwards to then bed. She pins you down with her soft body and lifts your legs up over her shoulders, giving her access to your exposed pussy.

"Pleassse...I wann it to be you Shamansha...pleassh be my firsss!" Your drunken ramblings are sweet poetry to her in the moment, she fights back tears of joy as she plunges in balls deep inside you. Her sissy clit sets off a chorus of angels singing hallelujah inside you, you feel like your body is bursting from being flooded with pure bliss, and perfect love flowing through your veins, melting you from the inside out, exploding your heart in an euphoric eruption that covers every inch of you in sticky sweet sissygasms. You both being sissy virgins, this perfect moment can't last long as Samantha explodes as well, filling your cunt with her sissy seed.

She collapses on top of you, still inside you and still entwined in ecstatic afterglow. You kiss softly and slowly, until you are too spent even for that. Then, rolling over, you fall asleep, side by side, leaving the questions of what happens next for the morning.