Erin Comes Home Early

It was early Friday night in the Anderson home and the place was nearly deserted. This evening found the man and woman of the house off on a mini vacation. The couple left for a night out on the town that would end in an upscale hotel suite. Erin, the daughter of Steve Anderson, was still at college, a freshman this year, and due to arrive home tomorrow afternoon for the start of spring break. That left Gary home alone. And Gary intended to make the best of his time. For the majority of his life he'd been an only child. His parents broke up somewhere around a decade ago when his mother discovered his father in bed with the secretary. That was about the fastest divorce on record and Gary and his mother had enjoyed a life of relaxed comfort for many years after due to his father being very high up in a local finance firm. Neither of them had wanted for anything and for his mother that included a replacement for her ex. She'd remained single and happy till just about two years ago when she met her new husband. They fell headlong in love with each other and were married within the year.

And that's where Erin fit in. Being Steve's daughter she became Gary's stepsister and the two each gained a first time sibling, Erin being big sister by about a year. The adjustment wasn't seamless, but it wasn't particularly difficult, either. A large part of that tidy transition was due to Gary's secret hobby. Since about age ten or so Gary had taken a keen interest in women's clothes, particularly in wearing them every chance he got. The most handy source of those clothes was his mother's closet, but not only did wearing his mom's clothes feel weird to him, he just didn't care for her fashion. This left Gary sneaking odds and ends from his friend's sisters or stealing this or that from stores, an act which caused feelings of anxiety to this day. Upon learning he was gaining a sister Gary just about jumped for joy at the prospect of having a closet right in his house from which he could pilfer soft slinky nothings. And what luck was it that Gary and Erin not only shared similar dispositions, but also similar stature. This was due in no small part to Gary keeping trim, exercising and watching what he ate while it simply came naturally to Erin.

Regardless, all of that leads us to where we are tonight. The moment his parents left the house Gary hopped into the shower and gave himself a deep cleaning. He even did so using his stepsister's toiletries, so when he finally emerged from the shower stall he was smelling of lavender and his skin was soft to the touch. Unconcerned about the possibility of his family members, who were tens, if not a hundred miles away finding him, Gary dried himself off, tossed the towel into the hamper and exited the bathroom. He confidently strode into his stepsister's room and took a deep breath as he looked around. Erin had been gone for months, but the room still smelled of her. It didn't occur to him, but it might have done so in part due to the scented showers he took evey time before entering.

After taking it all in, Gary walked up to the dresser and pulled the top drawer open. He knew exactly what he was looking for and in just a moment he had gathered it all. He took his plunder and laid it out on Erin's bed. Then he pulled from the collection the hot pink bustier. He was glad it closed in front because it had about a million little hooks and it took him a few minutes to get them all closed as is. Had it been a standard rear closure it probably would have taken ten minutes or more. No matter, it was on and he shimmied it into place. Erin was a fairly small breasted woman, so the cups were only slightly too big for Gary's pecs, but he'd fix that soon enough. For now he grabbed the matching garter belt and fastened that around his waist.

Taking a seat, Gary drew equally hot pink stocking up each of his legs, the sensual feel of the scratchy fabric running a shiver up his spine. He then carefully attached the four garter clips to the stocking tops, ensuring they were straight and even. Lastly, Gary stepped into the lacy thong, pulling it up and into place, the string bisecting his ass. Once it was finally situated Gary let out a deep sigh. He loved the feel of wearing a thong and this one was his favorite. The strip of fabric buried between his cheeks was rather wide compared to Erin's other thongs, so Gary was simply unable to forget it was there and that feeling really cemented in his mind that he was taking on the role of a girl. And a sexy one, at that.

With his under things situated it was time for Gary to consider what to wear over it. He walked to his stepsister's closet, loving how the thong rubbed his most sensitive places as he did. He took a look from left to right and considered a few different options before pulling out a short sleeveless blue dress with a conservative neckline. The neckline reminded him though, so Gary laid the dress on Erin's bed before going back to her dresser and pulling the bottom drawer open. At the far rear of the drawer he grabbed a pair of plain white boxes and placed them on top of the dresser. After closing the drawer he opened one of the boxes and pulled the flesh colored bit of silicon from within. He slipped it into the left cup of the hot pink bustier, then did the same with the contents of the other box and the right cup. He gave his chest a quick wiggle with both hands, working the small breast forms into place then made his way back to the bed and the blue dress.

---

There was something Gary was not aware of, however. His stepsister had a suspicion that Gary was getting into her things, so while she told everyone that she was coming home Saturday she was, in fact, already back in town. She didn't want to alert Gary to her presence so she pulled into the lot reserved for park goers and walked the hundred or so yards to their house. She eased the door open silently and stepped inside, removing her shoes as she crossed the threshold. She placed her shoes next to the door and quietly crept towards the staircase. The house was relatively new and most floors were carpeted so Erin needn't worry about noise as she climbed the stairs. On the second floor now she looked down the hall and was able to see right into Gary's room. It did not appear as though he was in there. I fucking got you, she thought as she tiptoed towards her bedroom. She was only a couple of steps from her door now and upon stopping and listening she could clearly hear her stepbrother inside. She was all but positive she knew what he was doing.

Now or never she thought as she peeked around the doorjamb and looked inside. She saw her stepbrother just as she expected to find him, facing away from her wearing one of her blue dresses and bright pink stockings. At least the boy could coordinate, she mused before stepping into the room and giving him the shock of his life. "What the fuck, Garand!" Erin shouted, using his full first name. How military obsessed does a father have to be to give a kid a name like that? His nickname Gary was definitely an improvement.

"What the f-" Gary shouted as he turned, practically falling into a heap as he spun to see his stepsister staring at him, apparently fuming. He caught himself on Erin's bed frame, otherwise he'd have gone sprawling.

"That's what I want to know," Erin countered, still giving Gary the stink eye. She struck quite the figure as she did. She was naturally five and a half feet tall, but with her heels she was approaching a full six feet. She wore a sharp white button down blouse and a loose black skirt. Her long legs were bare, it being too nice a day for stockings, she thought. She wore a scowl at the moment, but her face was obviously very pretty and her long blonde tresses complimented her bright red painted lips nicely.

"Uhh... umm," Gary started, "It's not what it-"

"Oh come the fuck on, Gary, what else could it be?" Erin cut him and his bullshit off sharply.

"Ummmm, I... I can explain," Gary insisted.

"Alright then, explain."

"Well," Erin had him dead to rights. She owned his ass and he knew it, so he decided on a bold move and just owned it. "You see, Erin. I, ahh, I'm a crossdresser."

"Well, no shit," his stepsister laughed.

"And?"

"And why are you doing it in my clothes, ya nimrod?" Erin was letting him have it, if a little softly. Perhaps she was impressed with Gary's choice to bite the bullet.

"Beeee... cause they're here?" Gary asked as much as answered.

"Jesus Christ dude, this is hilarious," Erin chuckled before continuing, "I gotta admit though, you almost make cute girl. Why don't you grab a wig?"

"Uhh, what? Really?"

"May as well, you're a crossdresser, aren't you?"

"That I am!" Gary proclaimed, clearly relieved. This was going far better than he expected when he first saw his stepsister appear out of nowhere. He walked over to Erin's closet, unconsciously still swaying his hips in a feminine motion as he fetched a medium length curly red wig.

"Damn, bro, nice ass," Erin catcalled as Gary grabbed the wig.

"Um, thanks," Gary whispered.

"Alright, lets how girly you can get, Gary. Or should I call you Gerry?" Erin joked.

"Ha, ha, Erin," Gary replied as he donned the wig. He flicked a few curls of red hair out of his face and turned towards his stepsister, meeting her gaze as he blew her a kiss.

"Wow, Gary," Erin breathed, "no lie. I'm impressed."

"Th- thanks again, Erin," Gary squeaked, feeling very out of sorts. He was clearly being evaluated as a girl rather than a boy and he was scared at how much he liked it.

"Seriously, dude," Erin continued, getting bolder. "If I had a dick I think I might want a piece of a girl as cute as you." She studied Gary's face carefully as she delivered the lecherous line, noting a slight redness creeping into the bridge of his nose. She was shocked at how well her manipulation was working.

"Well, uhh," Gary coughed briefly, struggling for words, "lets be glad you don't have one of those, Erin."

Hook, line and sinker, Erin mused. "But what if I do, dear brother? What then?" she prodded, feeling a rush of power as she began the process of exerting her will over her stepbrother.

Gary chuckled nervously as he attempted to stare down his stepsister. She wore a wicked grin and seemed more sure of herself than Gary had ever known her to be. He gulped hard.

"What do you suppose I have under here?" Erin seemed to ask the room itself, her voice a song as she reached her right hand under her skirt. A moment later her hand reemerged as she lifted the hem of her skirt away with her left hand. Given her extreme confidence Gary was unsurprised at the cock Erin was now clutching with her right hand, but at the same time he was downright shocked at its size. It utterly dwarfed the six inches Gary had in his panties and appeared to be twice as thick or more. How could a girl not too far north of a hundred pounds possibly sprout something so massive? Her freakish member now out in the open, Erin blew Gary a kiss of her own before reverting to her mischievous smile.

"Y- you're one of those?" Gary asked, his tone nonjudgmental, although the answer was painfully obvious.

"A dickgirl? All my life."

"And I, uh," Gary started, clearly shaken to the core, "I suppose you-"

"Wanna get this dick wet? You can bet your ass, little brother," Erin laughed at her crude joke, "or your mouth, whatever."

Gary's jaw about hit the floor at the straightforwardness with which Erin declared her intentions. "I umm..." Gary stumbled, "I've never. I mean, umm..."

"My little brothersister's a virgin?" Erin asked, in an only slightly teasing tone. "It's alright, I can show you all you need to know. I'll even let you choose how."

"Well there's no way I'm fitting that thing in my ass," Gary blurted out before slapping his hands over his mouth, a bright blush once again invading his features.

"Is that the voice of experience, Gary?"

To his credit, Gary forced a poker face and it left his sister in the dark. Regardless, his rear end was off the menu, at least for now.

"Well, you pretty little thing," Erin breathed in a suddenly very seductive voice, "why don't you come on over here and have a taste, then?" she gave her inhumanely large cock a shake, punctuating the request.

"I don't really have a choice, do I?" Gary asked as he took a tentative step towards his stepsister.

"Oh of course you do, baby," Erin practically purred, obviously very aroused at this point, "but I can see the hunger in your eyes. You want this thing and you can't deny it, can you?"

"I, um, I... no. No I can't" Gary admitted as he lowered himself to his knees, his stepsister suddenly looking very imposing as he looked up at her. He reached out and grabbed her huge veiny cock in his hand, taking back some semblance of control with it, and pulled it down level with his mouth. He immediately started laying kisses all over the head of Erin's beautiful beast, not allowing his brain even an instant to reconsider. After a few moments he took that cockhead into his mouth and gave it a few wet sucks, drawing a short moan from his big sister. Having the tip of her penis in his mouth really excited Gary and he drove forward taking a few more inches into his mouth before retreating back and trying to set up a rhythm.

"Ooh, oww," Erin groaned as she pushed Gary off of her stiff member. He looked up at her, his brow furrowed in concern. "Teeth!" she hissed.

"S-sorry,"

"S'OK, you're new at this," Erin soothed. "Maybe try not to get so excited.

Gary nodded before carefully taking Erin's enormous tool back into his mouth. Taking his time he worked nearly half of Erin's penis into his mouth before hitting his gag reflex and hitting it hard. He violently pulled off of her as a fit of coughing wracked his body.

"Damn, dude, you OK?" Erin asked, her voice full of concern.

Gary nodded as he straightened back up before he grabbed Erin's cock and again drew it into his mouth. He fought his eagerness and after a minute or two finally felt comfortable enough to again take in more of his stepsister's cock, which barely seemed to fit in his mouth as it was. And just as before the head of her cock brushed something and the urge to unload the contents of his stomach became unbearable. Gary pulled away and loudly emptied a mouthful of saliva and bile onto Erin's carpet.

"Alright, buddy, I'm calling it," Erin announced. "Don't be ashamed though, yours is not the first mouth that couldn't handle me, or the tenth, in fact."

It took Gary a moment to compose himself, but he finally looked up at his stepsister. "But I, you, we..." Gary again grasped for words. "I wanted so bad to make you feel good, Erin."

"Don't worry about it, it happens."

"But, I mean..." Gary again started forming his thoughts. "It's such a nice fucking cock, Erin." She grinned at his praise. "I mean... fuck, I really wanted to make it nice."

"Well..." Erin began, letting the word hang for a moment before continuing. "There is that other thing we could try..."

"Erin I don't think..."

"Maybe you don't think, but that doesn't mean we can't at least try, right?" A crooked smile crept onto Erin's face as she floated the idea. "Only thing is I don't have any lube."

"Oh, I-" Gary started before again catching himself and slapping his hands over his mouth.

"I knew it!" Erin roared.

"Busted," Gary sighed.

"Well, what are you waiting for?"

At his sister's insistence Gary hopped off the floor and practically ran for his room. A moment later he returned with a plastic container.

"Really, dude?" Erin inquired as she eyed the jar of petroleum jelly skeptically. "Do you even know that this stuff is actually rather substandard butt lube?"

"Been working fine for me," Gary admitted with a blush.

"Alright" Erin responded as she pulled the cap off "Jesus, I guess it has, wow!" she chuckled as she looked inside to see the jar nearly empty. "At least you're experienced."

"Um, yes," was all Gary could force himself to say in acknowledgment.

"Well, you wanna lose that?" Erin asked, waving at Gary's dress in general as she scooped a couple fingers of petroleum jelly out of the jar.

Gary got to work disrobing as Erin massaged the improvised lube into her freakish cock. He tossed the dress off to some corner of the room, revealing the full set of bright pink lingerie and stopped to watch as his stepsister applied the jelly. She was only lubing up the top half of her cock at the moment, but even so she had to stroke her hand up and down the rigid flesh as she did. Gary watched with a combination of awe and envy, doing some math and estimation in his head he guessed Erin's cock to be twelve, maybe fourteen inches long and approaching three inches in diameter. He suddenly didn't feel so bad about being unable to adequately perform fellatio on her. Then the realization really struck home. She was going to try to fit that monster in his butt. Intimidation reared its head, but as he stopped to think about some of his bigger toys that intimidation was tempered with anticipation. Gary found himself downright excited at the prospect of being impaled on his stepsister's huge cock.

"Alright, your turn, dude," Erin announced. "Do you want to or should I?"

"I've never had someone else prep me. Sounds kinda fun," Gary chuckled.

"As you wish, turn around," Erin instructed.

Gary did as asked and turned, tugging the hot pink thong down as he did. The wide string clung tenaciously inside the crack of his ass for a moment before snapping down with the rest of the thong and falling to the floor. He stepped out of it and stood, his feet wide apart. Erin took the opportunity to wipe a huge gob of jelly square on his anus, wiping back and forth to center the mass, then she slowly began sinking her index finger into her stepbrother's asshole. Gary cooed as Erin worked her finger into his backside. It was clear to her that this was a piece of cake for him so she quickly added a second finger to the task, twisting as she went. She took her time, smearing as much jelly into Gary's insides as she could. A few minutes later the gob of jelly was all but gone. Wanting to ensure a smooth entry she slapped another dollop of petroleum jelly onto her stepbrother's anus and worked that one in as well.

"Alright, I think you're ready," Erin purred.

"Um, sis, this might sound kinda gay, but think we can go missionary?" Gary asked. "I kinda wanna watch you fuck me."

"As unbelievably hot as that sounds, Gary, I think you'll have a better time, at least to start, if I go at you from behind."

"That the voice of experience?"

"Uh huh."

"OK, then."

"Just relax, OK?" Erin instructed as she placed her left hand on Gary's hip and grabbed her cock at about the halfway point with her right. To her relief she felt her stepbrother loosen up in her grasp. With that she lined herself up with Gary's anus and pushed against him. Nothing happened at first. In fact, very little happened for about a minute, but Erin kept firm pressure against Gary's asshole the whole time. "Try to push out a little," She told him as she continued pushing towards him. A moment later she felt Gary's pucker slowly start to give way. The head of her cock wasn't entering him just yet, but it was easing the sphincter open. It wouldn't be much longer. "That's it, baby," Erin encouraged as she felt the inevitable start to happen.

"Holy shit, Erin," Gary groaned," You're fucking enormous." For just a moment his relaxation waned and his rear began to close again.

"Easy, easy," Erin called, "you've got to loosen back up, baby. We're so close." Erin kept firm pressure, but progress was at a standstill. A moment later her stepbrother took a few deep breaths then she felt him relax and again she was making headway. Gary's anus opened up like a flower and before the step siblings knew it the head of Erin's massive penis was firmly lodged inside of Gary's ass. 'Ohh fuck yeah, baby! There it is," Erin shouted excitedly.