Stepbrothers To Sissy Sisters

The two step-brothers weren't sure if they'd get along at first. They were both 19 and living with their parents while they went to community college. After the wedding they would have to share a room and they were not happy about that. But both their parents told them they could either deal with it or move out, so they grudgingly accepted it. They didn't know it but they shared a secret and they were both worried about how they would keep from being found out. The first few weeks were awkward. Tiptoeing around each other and hiding their secret fetish from each other was taxing.

Then, one night a few weeks after they moved in together, their parents were out at a party. The boys got in to the liquor cabinet and were getting pretty drunk. There was an erotic movie on one of the premium cable channels and that led the discussion to porn.

"That chick is hot but these skinamax sex scenes are so weak."

"Tell me about it. I like to see some real shit. I want my porno to be graphic and kinky."

"Hell yeah, I'm all about kinky. Do you have any good vids on your laptop? I got some fucking hot ones."

"Sure, but they are really kinky. I don't think you could handle them."

"What, are they like donkey shows or something?" they laughed and took another shot of vodka.

"No, nothing like that. But still... I don't know if you like the stuff I like."

"So it's like gay porn or something?"

"No, not really... I guess you'd call it bi."

"Fuck yeah? That's cool. I mean, I don't even mind gay porn if it's really hot, but I could really get in to some bisexual stuff. Don't freak out or anything, but I'm like super in to strap-on type stuff."

"Holy shit! Me too. Some of my favs are like sissification or sexy passable tgirls."

"No way, that is too crazy. I can't believe I've been hiding my stuff for weeks now. I'm about to burst with all the backed up cum from not being able to do what I normally do."

"What do you mean? What stuff do you have?"

"Well... this is just between us, right?"

"Totally! I won't say anything and I don't want anyone to know that I like chicks with dicks or whatever."

"How about we give each other a little insurance that we won't blab?"

"What do you mean?"

"Come upstairs and see."

In a trunk hidden in the back of the closet there was a treasure trove of sex toys, make-up, several wigs, and sexy girls clothes, including a bunch of lingerie that looked like a porn stars collection.

"So you like to watch sissy boys be feminized, but have you ever done it yourself?"

"Sort of, but not really. I stole a bikini top from the locker room of our community pool a few years ago and wore that a lot in private. And I once bought some chapstick that was more like lipstick and used to love putting that on when I was alone. But I never got to actually go for it."

"Now is your chance. You can go for it and become a sexy gurl with me if you can keep it just our secret."

"I can keep it a secret! This is like a wet dream come true. I'll do whatever you want."

"Good. I have an idea. We should both dress up and we can take some pictures of each other. Since we both will have compromising pics of each other we know that neither will talk."

"Wow, you're dark! But I'm in. Totally."

The boys sorted through the stash and selected their outfits. They couldn't help but notice each other's stiff cocks as they got dolled up in slutty girly clothes. Since their parents could be back at any time they had to hurry so there was no time for make-up and wigs but they both picked out a couple dildos to suck on so that the pictures were extra naughty and potentially embarrassing.

"I can't believe you have such a great collection. How did you get it all?"

"I've been collecting since before I could drive. Most came from the internet, but there are a couple of stores in the city that I like to go to. We should go together."

That was when they heard a car pull up the driveway. They hurriedly changed and put everything away. Pretending to be asleep, they both had to lay on their sides to hide the throbbing boners they both had. What started as an awkward situation had suddenly become the best thing either 19 year old crossdresser could dream of. They couldn't wait to explore their fetish together some more. And they wouldn't have to wait long.

The honeymoon was going to mean the boys had the house to themselves for over two weeks. As their parents headed off to the airport the boys were giddy to begin their 'transformation'. They toasted the start of their girly vacation with double shots of tequila and got out the supplies they had prepared.

"You ready? We're really going to do this, right?"

"Oh yes, honey. I am so ready. I've been practicing my girly voice and walk every chance I got."

"Me too. I think after we get 'changed' it'll be easier to slip in to character, too."

"So we are really going to stay in character for the whole two weeks, right?"

"You got it girl. You can only break character if my mom or your dad calls, but right back to it after the call ends."

"Right. So let's get started!"

Neither boy had much facial hair to begin with, but they had been secretly using their mom's laser hair remover on their cheeks and necks for weeks. The results were good and there wasn't any hint of beard shadow on either of them. The first step now was to take care of any body hair. Stripping nude in the master bathroom they helped each other smear hair removal cream in a thick layer all over their bodies. From the neck down, every inch of them was coated in the powerful cream. They got in the shower together and watched as all the hair just rinsed off their bodies. Suddenly they were completely smooth all over and already starting to feel very feminine. They giggled like schoolgirls and began using their higher pitched fem voices.

"It's time, sweetie. We gotta make up our minds on our fem names."

"Ok, yay! Well, I was really thinking of going with Chloe but now that we started our transformation I feel more like a Heather. So, yeah, I'm sure, my name is Heather now."

"Oh I love it! You are totally a Heather."

"Oh yay, thanks honey. You're nailing that girly voice btw. You sound so cute and natural."

"Shut up sweetie! You sound way more natural than me!"

The boys were really beginning to change into their girly personas. They playfully splashed water at each other from the showerhead and even gave each other flirty little kisses while they giggled and bounced around.

"For real though, your turn to pick your name."

"All right, all right. But I don't know anymore. You're totally a Heather but I don't know what name fits me. What do you think?"

Looking at her brother-turned-sister Heather tried to size up what she saw. A wispy frame at 5'8 and only 120 lbs. A thin build that made her look long and lanky. And, now that she was totally hairless and beginning to look much more feminine, Heather noticed that her sister had dainty features.

"I think you look like a Emily."

"I love it! Yes, call me Emily."

Out of the shower they dried off and moisturized their new smooth bodies. Heather really enjoyed the feeling spreading lotion over her silky skin. She spent a little extra time feeling her legs and found that her nipples were suddenly sensitive. Emily couldn't help admiring her sister's naked body. Where she was lithe and lean, Heather had a little bit of plumpness that made her look curvy and a little voluptuous.

"Hey honey, can I help you lotion your butt?"

"Sure Emily, if you want to touch me then just go ahead and do it."

"I really do. You just have such a juicy round backside and I'm so jealous I want to rub all over it."

Heather put her elbows on the sink and poked out her butt. Emily poured a liberal amount of lotion into her hands and stepped up behind her sister and began massaging and caressing that firm round butt. Both girls savored the feeling and let out little pleasant moans. Hands moved from making circles around the hips and cheeks to slipping in between the crack.

Emily's fingers brushed against Heather's asshole and Heather let out a louder moan. Her fingertips found the tight rosebud and began massaging it. Heather rocked back bit by bit until Emily's fingertips slipped just inside.

"Oh fuck sis, I have never had anyone play with my pussy before. It feels soooooo good."

"Have you ever had a toy inside you?"

"No, I'm a total virgin." Heather looked back over her shoulder "Will you pop my cherry, Emily? Please, I want to be your little whore."

Emily had a small, thin cock that wouldn't hurt her tight butthole but at that moment Heather would have begged to be fucked no matter how big and thick her sister's cock was. So after working her hole open a little bit more, Emily pulled her fingers out and Heather whined at being empty.

"Oh sexy girl, I want you back inside me. I'm your sissy slut. I need my pussy filled."

Heather poked her plump ass out and spread her cheeks while she moaned and begged. Emily rubbed a little lotion on her skinny 5 inch clitty as pre-cum dripped from the tip. She grabbed on to her sister's bouncy ass with one dainty hand and with the other hand she guided her girl-dick to Heather's eager fuck hole. As soon as Heather felt the press of a hard penis on her asshole she pushed back on to it, burying Emily's cock inside of her slutty boy-pussy until she felt balls pressing against her.

"Oh fuck yes slut," Emily managed to stay in character and her voice was passionate but high and feminine "You have a tight little pussy, don't you sissy bitch? You like pushing my girl-dick up your tight hole, don't you slut?"

"Yes, oh yes, oh yes, fuck yes!" Heather bounced her ass back and forth the full length of her sister's cock hard and fast. "I am such a little slut bitch for you Emily. Say I'm a whore. Tell me you like my virgin ass-pussy. I'm your sissy slut."

Emily could feel Heather's ass contracting on her dick and knew Heather was about to cum. She pumped her sister's asshole harder and reached around to stroke her thick cock.

"You are my filthy little whore, Heather. Look how hard your big sissy dick gets when you have my cock up your slutty asshole. You are a nasty little bitch who likes being fucked up the ass by your sister."

"Oh my god, yes! I love it so much!"

"I'm going to cum inside you baby. Cum with me. Let me see you shoot your sweet cum while I fill up your little pussy. Cum for me slut, be a good girl."

Emily's hand slid up and down Heather's long thick cock, milking ropes of thick white jizz all over the bathroom floor. The feeling of Heather's orgasm sent Emily over the edge and her pretty girly dick exploded, shooting spurt after spurt of cum up the ass of her tgirl step-sister. They screamed out in ecstasy, and even their moans stayed in character making them sound like two real girls having amazing orgasms. The characters were taking over and they knew that they were going to feel very comfortable as Heather and Emily.

"Oh fuck Emily" Heather purred while leaned over the sink and enjoying the feeling of her ass still filled with her sister's cock "That was the best cum I ever had."

"Me too sweetie. And we're just getting started!"