I woke from what seem to be a fever dream. I dreamed that my roommate John was "Amy's" long time sexting buddy and that he had caught me as Amy. As I opened my I realized that my dream was a reality. My virgin boi-pussy was filled with my roommates hot cum and was winking trying to hold onto as much of it as possible, while my plaid skirt and his shirt had streaks of my cum staining them.
I giggled and pushed John off me. He groaned a little and I took of my heels not wanting to wake him up. As I slipped off my shoes, I couldn't stop looking at his semi erect cock. "My god if that isn't the most amazing cock I have ever seen!" I thought to myself again. I then finally took a good look at him, wearing a loose t-shirt that clearly didn't fit him, smooth face, body, and not at all muscular other than his massive member I found myself thinking "He's like me from two years ago." My brain just switched and a wonderful idea started to brew. But first I couldn't leave the wonderful gift laying in my bed alone. I leaned in and inhaled deeply taking in the aroma of my ass and his cum mixed together. It was intoxicating to say the least and my mouth naturally opened.
After practicing for several months on dildos I had gotten use to a cock in my mouth, but the real thing was so much better. The warmth of his body pulsating with my sucking, growing more in excitement. John started to stir and opened his eyes.
I loved seeing the twinkle in his eye looking down at me hungrily sucking and swirling my tongue around his massive member as I start to slowly massage it with my free hand. Grabbing my hair as a handle he said, "I could get use to waking up like this."
He began pressing him further down his massive shaft and I swallowed making sure to not gag and bring him into my throat.
"No one's been able to get me that deep inside them," he moaned as tears started to fill my eyes. He slowly let go of my hair and I started to take back control of sucking him off. Pumping his massive saliva covered shaft and sucking furiously at his head, I deiced to start my plan and began to massage his massive balls while pressing my middle finger to his ass.
He seemed to leak a little more precum as I finger pressed against his hole along with the tell tail vibration of cock telling me he was at his limit. His body seemed to push against me as if wanting more, happily I pushed my pinky inside him.
"I'm cumming!" he screamed as ropes of his hot cum coated the back of the throat and tongue. I hungrily ate up all that his body gave me and sucked his cock clean of cum as he quivered. Making sure to swallow all but a small amount, I came up to John and pressed my lips against his pushing some of the cum into his mouth. At first he seemed to protest but melted into as I rubbed myself against his body.
After swirling the cum between our mouths I managed to get Jonny to swallow it. His face was a little perplexed at what he did, but he was still sprouting a massive hardon. "That was," he stuttered "different."
"There's more where that came from if you'd like," I say while nibbling on his ear.
Feeling his cock twitch I knew I had him right where I wanted him. "But there is a price my sexy friend."
"Anything," he says grabbing my waist and raising his hips pressing against my waiting ass. Giving him a little kiss and wagging a finger in his face, denying my own release know of the fun I hope to have, I slide of him. "I'll be your ultimate cock slave, make you cum whenever and however you'd like until you've had your way with me on one condition."
"Did I just say thing!" Johnny whined
"I want to do a 'Twin' photo shoot with you."
I could see the wheels turning in his mind, "What do you mean twin?"
"Well you see I've got this rather sexy cosplay outfit I've wanted to pose in as Amy of course, but I've been missing my partner. If you'd be my partner it would make my followers go wild!" I say cheerfully.
"I hope this works my God would it be amazing to see that glorious cock in a little dress" After what seem like ages Johnny gives me a passionate kiss, "Fuck me, but in for a penny in for a pound. If this means you're mine then I think it might be worth it."
I grab his face a kiss him deeply. "Yay!!!!" I practically scream. I pull him off of the bed and grab him by the hand leading him to the bathroom.
"First things first, we have to shave off all that hair. So hop into the shower and make sure you soap up." Looking somewhat confused and still on board Johnny turns on the hot water and heads into clean up a bit. I follow shortly behind him after taking off my rather battered clothes.
For a couple of moments we just enjoy the feeling of warm water running down our bodies before I grab the razor from under the sink. "Now hold still while I make you smooth and soft."
Meticulously I remove all the hair on his body, pay special attention to his amazing cock and balls doing my best to just give them a little kiss and not devour them right there and then. Having a little fun I make a small heart bush above his member.
Turning off the water, I look Johnny up and down "Damn besides his cock, balls, and short hair he looks just like a girl! How didn't I see this until now" I think as the image of my sissy sister starts to form we head out of the shower.
I feel Johnny's cock pressing against me as I bring him back to my room, "Uhh, Amy I think I've been rather good, maybe a little reward is in order." I sit him down in my chair, "Almost" I say bending down flicking his pulsing member with my tongue. "Close your eyes while I get the cloths out, and then we'll get started on our makeup." I could see Johnny start to squirm a little at the word makeup, but eventually settle in.
I quickly grab a blind fold from my dresser and cover Johnny's eyes, "Now no peeking!"
I get into my sissy zone, I start pulling out my twin maid outfits: White thigh high stockings with a red little lace woven into the top, matching white laced garter and panties, thigh length wide black skirt with white lace trim, a white apron, black corset with little white bows for buttons and straps over the shoulder, a white short cut blouse with red lace to match the stockings, white padded push up bra with lace of course, white lace collar, embordered flowing black arm coverings, and finally a blue wig for me and a red wig for Johnny.
My body was just shaking as I laid everything out. After taking a deep breath I headed over to Johnny to start on his makeup.
"Now hold still and we'll finish this quickly," I say giving him a little kiss on the lips. He nodded slightly as he tried to lean over and see the clothes. I quickly grab the chair and turn it towards me not letting him move. I quickly but meticulously go apply the foundation, concealer, blush, eyeliner, eyeshadow, and lipstick to my patient roommate and myself making sure we are matching.
As much as I was enjoying his transformation my body was beginning to ache for his cock, making me go even faster. Finally after half an hour I was done with our make up. "Now for the outfit!" I say.
Johnny still in somewhat shock at what's going on just nods. I gradually dress Jonny and myself in our twin outfits. As I put him in the stockings at panties I hear him let out a small muffled moan, I smile widely. After all the clothes were on and I set our wigs I make the final touch ups to our makeup making sure that it all looked perfect.
Taking a deep breath I give Johnny another little peck on the lips, "Thanks for all your patients darling, this is going to be amazing, and now for our photo shoot!"
"And then you're mine," Johnny says somewhat quietly as he grasps the skirt and feels the fabric against his skin.
"He's just like I was when I started crossdressing" I think to myself as I set up the lights and camera in front of my computer.
As our picture shows up on the screen Johnny gasps as he finally seen himself for the first time, "That's me?!" He practically screams. I takes a step back and turns a little bit evaluating the sexy sissy he sees in front of him.
"I look hot as fuck!" he says as I see him sway in his skirt.
"Good thing I lock his monster cock to his leg with a bit of cloth." I think to myself.
"Like I knew you were sexy Will, I mean Amy, but man I'm sexy too!"
"Of course you are! You're my twin!" I grab his hand and kiss him deeply. "Now why don't we make my fans go crazy!"
I start snapping photos and recording, first having us face the camera with our faces pressed against each other while holding our hands. Then with us lying on the bed me leaning on Johnny. As I get up to move I can feel his member pressing against my body, I run my hand along his stockings, "It feels like someone is getting excited," I say in my most feminine voice.
He reacts almost instantly, and I feel his cock twitch. "Now Ashely," I say stressing the name, "If I didn't know any better I'd say you like this costume."
"Mmhmm" is all he can muster as I finally reach my goal and place my hand on his member. I crawl up to his ear and whisper, "Why don't we make it an extra special photo shoot hmm."
Again he lets out a soft moan as I lift up his skirt and reveal to the camera his cock and panties. Looking at the screen I'm entranced and the scene, "This is always what I dreamed for, another sissy!"
I forget about the camera and start kissing Ashely, pushing my tongue into his mouth enjoying the flavor, all while making sure not to move my hand from his cock. Loosing himself in the feeling of our bodies pressing against each other Ashely, grabs my chest and starts rubbing my nipples between his fingers.
"Ahh, not so hard Ashely."
He relaxes his grip and starts to lift up my skirt grabbing my ass. Knowing how much he and I both want this, I lower myself onto his cock and bring it to my mouth.
"Soon Ashely," I say as he arches his back raising his cock further into my mouth.
"I can't wait any longer!" He screams grabbing my hair and pushing his cock deep into my throat. After seconds I'm greeted with the wonderful sensation of his body shaking, cock pulsating, and warm cum hitting the back of my throat. I nearly cum then and there by I grab myself hard making sure I don't yet release. I let Ashely enjoy the waves of pleasure as he yet again nearly passes out in ecstasy. Making sure to suck every last drop of his cum I swallow deeply.
Slowly rising and feeling the ache that had been growing inside me this whole time I quickly grab my butt plug and place it inside of me. Ashely still in a dream like state, I put a little bit of lube on his winking boi-pussy and my own clitty. Raising his legs, I push my cock against his hole. Without thinking he starts to push against my cock and with a little help I push inside of him.
"Ahhhhh" he moans out, "is that you Amy?"
"Yes Ashely, I'm taking your virginity." I say as I slide my whole cock inside him.
"Be gentle" he says biting down on his finger.
"Don't worry you'll love this!" I start to rock my hips nearly removing myself from him before pushing back in, while having a firm grip on his rock hard cock.
"Oooo that feels sooooooo gooood!" Ashely mummers as his ass tightens around me.
"Don't do that or I'll," is all I can get out before my body convulses and I start impregnating Ashely's boi-pussy with my seed. As I fill him more and more, I feel his cock vibrate and release once more.
We both pant like dogs in heat as I slowly remove myself from inside him, quickly grabbing another plug, this one with a pink stud. "I'm going to fill you up from now on," I say as I turn remembering the camera and hit upload to the video and photos.