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Introduction:

Kimmy wanted a dress up doll. She got one, and a pinch more
this is my first story... I hope it works well thank you in advance for your comments, critiques, and encouragements

Kimmy was your reasonably normal 16 year old girl, maybe a little odd at times, but it was normal to her. Her family was comfortable, not wealthy but not poor. she lived in a fairly large house with a decent sized yard with both her mom, who was not home very often as she spent a lot of time travelling on the job, but was home enough to be a fixture and dad who was worked a lot of hours at the school she attended. Her little brother, Johnny, on the other hand was 14, and went to the middle school in the allocated area.

the popular toy at the time were these plush dress up dolls, this is a strange phenomenon as the doll phase usually phases out at a young age, but this one seemed to have attracted the older kids. Perhaps because of its suggestiveness and anatomical correctness, who knows really, it just seemed to have caught on.

Now Kimmy asked her parents for this doll, but they refused saying that she shouldn't just follow the fad that everyone else is following. So she would pout and moan but to no avail. Eventually she gave up the idea, and simply satisfied herself with enjoying her friends’ dolls.

Kimmy had flings, she was a good looking girl, bust of a healthy B, medium sized panties, which she typically wore thongs, and height of 5'5" weighing in at 110 lbs. long slightly wavy freckled brown hair that rested gently on her shoulders, and she would straighten her bangs to cover one of her eyes at an angle. Her dress varied depending on her mood, sometimes it was pajama bottoms with a cute form fitting top, other times it was spandex that hugged her shapely booty that gave the Latina girls at school a run for their money; and other days all out slutty-classy. She had large blue eyes with a hazel ring around the pupil, the cutest nose, soft rounded face with a hint of freckle. Medium lips which served as a gate way to a deep throat [more on that later].

she had boyfriends and flings nothing ever too serious as her parents wanted her to focus on school work, but they knew the inevitable was to happen; so they gave her a comprehensive safe sex talk and let her make her own decisions and trusted her, and she took the knowledge and used it well--wanting to avoid pregnancy first and foremost anal and oral were her go to's.

One day, when she decided to startle her current fling with a surprise blowjob in the girls’ bathroom she discovered something interesting. She grabbed him by the hand, and dragged him in there. He was apprehensive and resistant at first but with a nibble on his ear lobe and cop of a feel up her skirt to feel her g-string, he melted and followed. They made out for a bit, felt each other up, and she never told him why they were there, when she got to undo his belt and jeans he withdrew rather sharply. She was obviously startle, "what gives? I’ve sucked your dick before."

"I know, but today is a little bit different!" he responded

"how different can it be? I let you cum on my face? You know I only let you do that when we can clean up in our luxury."

"Well... er..."

"Oh shut up and let me suck your cock!"

He relinquished a reigns and let what would happen, and when what happened in a sharp inhale, and a gasp.

"What is this?"

She found out that her recent fling was wearing a satiny meshy light blue thong with "love pink" written across it. She made him take off all his clothes and spin for her. His cheeks flushed the bright color of rose and conceded and thought to himself, "I’ve come this far, what's another little bit of humiliation..."

but the humiliation never came. In fact there seemed to be intrigue, ingenuity and lust written all over her face, she was just as flush as he was, but when he looked down he noticed she was gently yet briskly rubbing her clit, almost absent-mindedly.

"Kimmy?"

She snapped out of her daze with a start and when she collected herself a couple seconds later responded, "How long have you been dressing in girl’s panties?"

"I’ve been doing this since I was three."

"Have you told anyone about this?"

"You’re the first."

"that's awesome, I’m surprised how much I enjoy it, now come here and let me suck that thonged up cock of yours"

and she did, quickly dropping to her knees and gave one of the most vigorous cock sucking sessions she'd ever given, lots of noise but not sloppy, taking him deep in her throat until he came and lost all senses. When she finished swallowing down his seed, he was spent and could barely stand if at all. She quite simply got up from her knees adjusted her outfit and walked out without saying a word, but only a simply kiss on the cheek.

She made it home later that same day still thinking about seeing her boytoy in a thong and got a brilliant idea of how she could get her own dress up doll that was even better than those of her girlfriends’. "But how to work it out?" she thought to herself... Johnny will be very confused.

A couple days later, filled with thoughts and planning, she waited for an opportune moment, when mom and dad would be gone for a day or two, and Johnny would be home. She didn’t have long to wait as dad was often out of town for this conference or that and mom as well. So she picked up a couple cute outfits for dear little Johnny, and make up to match and played the waiting game. Before hand she had picked up a fifth of rum, just in case he was hard to persuade. When mom and dad left leaving the usual "no parties, no drinking, no drugs" warning that they usually give before their departure, Johnny invited some friends over to play videogames and smoke weed.

Kimmy didn't particularly like this, but she could bide her time, and after they've had their fun she'd kick them out. After the pipe had been passed, and the games played they were looking sleepy, all but Johnny, as he was typically a hoot owl anyways. So Kimmy took the initiative.

"Alright, closing time, you don't have to go home, but you can't stay here."

Johnny protested, but Kimmy shot him down with a few logical points about keeping things clean, allowing them to smoke up and no fouls. Johnny conceded, albeit reluctantly but slapped hands and his friends left. She sat snug on the couch and he plopped down next to her.

She finally got a good look at her little brother. for the most part he had always been just that, little Johnny, but for some reason she now noticed that he had a very slender body, "swimmer’s body" she thought she had heard the type called, she had the same hair as her except it was medium length, kind of shaggy but not too long, same kind of eyes, a little bit more pointy of a facial structure, but otherwise... pretty, she was already moist.

Johnny looked at here, "what's with the daze in your eyes, sis?"

She shook her head and responded, "oh nothing. Hey I was wondering I have this bottle of rum, wanna get down with me?"

"Why couldn't the guys stay for this? now it's turning into a party"

"Well we rarely see each other and I wanted to get to know you a bit more, thinking we could just share it ourselves?"

Johnny considered her point and conceded. He was actually really happy to do so he had always had a kind of crush on his sister, but pushed them a side as being perverted. He would often catch himself trying to sneak peeks up her skirt when following her up the stairs; knowing that she pretties much only wore thongs. He was more than happy to hangout with her

"why aren't you hanging out with one of your boyfriends tonight?" Johnny asked

"like I said, I wanted to spend time with you tonight."

Happily Johnny got up and grabbed with 2 liter of cola and some glasses. Kimmy mixed them some drinks and they drank in silence for longer than was comfortable. Kimmy broke the silence...

"Seeing anyone?"

"Yeah, kinda, there's this one girl I like, but she hardly notices me."

"Why not? You’re a good looking guy!"

"I don't know, she always goes for the bulky guys" and looking down at himself to make the point, "I’m just not that."

Kimmy rather daringly and with a wink and smile said, "you know, sometime big gifts come in small packages"

"What do you mean by that?" he asked laughingly

"Well, imagine a slightly slender frame like yours but with a nice big cock." she responded placing emphasis on the last three words. Johnny blushed at this and started to involuntarily squirm.

"Have you stuck your dick in any girls yet?" Kimmy asked

Johnny turned three shades of red, but said, "no, no I have not, but I did almost get a handjob and blowjob before, but she got scared when she thought she heard something and the other her dad got home just as my pants were down to get in her mouth."

"Oh my, that's a shame; I bet it would've been grand." what Johnny didn't know was that she was talking about engulfing him, not being engulfed.

"Yeah, so close!" he exclaimed with a little bit too much dynamics

"The booze must be kicking in," she thought to herself, "game time"

"So, Johnny, what do you think of thongs and women's panties?"

"I love them; I love the silkiness and seeing when the thong disappears into the ass."

"Wow, easier than expected" she thought

"Have you ever tried them on?" she asked timidly

"Me? No, that's gay, dude!"

"No it isn't lots of guys do It." she didn't know if that was true or not but she had to coerce him somehow.

"Really? Well I have been kind of curious what it feels like."

"Perfect," she thought to herself

"Come on, grab the soda" grabbing the bottle and his hand, she led him up to her private domain: her room. When he entered her room, she closed the door behind him and he laid down on her bed unceremoniously. Kimmy stood the bottles on her dressed and sat down next to her doll. Johnny smiled sheepishly and looked mold-able.

Kimmy, then said kind of imperatively, "strip!"

"What?"

"You heard me, I want you to get naked for me!" she hadn't quite thought this part out yet, she was thinking it would take a lot more convincing to get this far so no plan had been made thus far.

"No"

"C'mon, I wanna see you in my panties."

"You what? I’m outta here" as he headed toward the door she said

"I’ll make it worth it to you"

"And how do you plan on doing so?"

She thought hastily, money wasn't what he wanted; he had connections for drugs...

"I’ll suck your dick!" she was surprised by her suddenness--but it stopped him

Johnny was not expecting this, not expecting this one bit... but he had to admit he was intrigued and kind of liked where this was going...

"You’ll suck my dick... if I what now?"

She gave a great heave of breath and was about to abandon ship when a wave of arousal coursed through her like a tsunami that had moments before disappeared from the beach

"If you let me dress you in an outfit of my choosing and do your make up, I’ll suck your dick" Johnny thought about this for a minute.

"Only if I can take a picture"

"What?!" she was surprised by this sudden blackmail move "absolutely not!"

"Then no dress up." She was about to lose her prospect

"Fine..." she responded quietly "but I get to take pictures of you too"

Johnny was drunk enough to not be thinking of blackmail, he just wanted more jerk off material that was more substantial than the typical internet porn you find on xnxx.com or the like "Good, oh and I want you to be in only your thong too"

Kimmy had already traveled thus far "deal" and Kimmy proceeded to ceremoniously strip down to her thong, while Johnny got completely naked. with every article Kimmy shed Johnny’s mast became that much more full until he was nude and she was in her normal bikini panties, when Johnny saw this "I said a thong"

"I know. I was just getting there" Kimmy turned around lowered her under wear pulled two thongs from her drawer and slipped into one. Turning around, she was not expecting what she saw. It wasn't huge by any means but it was still an impressive size. For the frame that Johnny had his cock was not proportionate it LOOKED huge. She began to wonder how it was going to fit in one of her tiny thongs.

Johnny was kind of dazed at finally seeing his sister in all her glory, she seemed so comfortable naked and in a thong, he had forgotten what was happening until she handed him one of her thongs, and a tiny groan/moan escaped his lips "So you just want me to dress up in what you tell me, and do as you say, and you'll suck my dick?"

"That’s right"

"Alright, have your way with me"

"That's all she needed to hear." She proceeded to slip on the thong and made him do a twirl for her, snapping off pictures with her phone camera. He took a few of her doing twirls she then pulled out a sexy little number, which included a too short tight black clubbing dress

"Click-click-click" went their cameras taking on various poses for one another. Kimmy then noticed that Johnny was rock hard when she rubbed up against her in her fit of carelessness. They were dancing and taking shots periodically throughout the adventure and they were both really enjoying the games they were playing and both very aroused.

"Ok, finishing touches, put on these 6" platform stilettos and this make up, sit!"

Johnny obeyed, and let her paint his face...when she was done his hair was done his makeup, flawless, if he didn't know any better he’d have sworn he was cute girl... a VERY cute girl

Kimmy agreed... and so did her pussy. She took a couple final pictures and when the giggling died down, she knew what was next. Johnny stood there in front of her kind of stupidly, the giggles slowly escaping his lips as the realization dawned on him. Kimmy slowly approached Johnny and once again ordered, "sit!" but with a lot less, conviction. Johnny once again obeyed hesitantly, sitting on the edge of her bed. Kimmy dropped to her knees in between his legs and approached him.

"Kimmy, you don't have to do this"

"I know, but we made an agreement"

"I had loads of fun, we can call it off..." he hated the idea of passing up a blowjob, but her half shut eyes and sober look on her face gave the impression of reluctance. What Johnny didn't know was the look of pure lust, lust in its essence. Kimmy was so far gone past the point of horny it breached a completely different level. Kimmy, hands on the insides of Johnny’s thighs rubbed them up, slowly crawling her way up to under the skirt he was wearing, and then to massaging his balls through her thong on him and feeling the length of his shaft. She spread Johnny’s legs until her skirt hiked up revealing the thonged package. She slipped the thong to one side freeing his cock and gingerly stroked his shaft, and a small moan escaped his lips as he enjoyed his first handjob. Kimmy was mesmerized by his rigid velvet, and only when she saw in her peripherals him look down, she looked up into his eyes, made eye contact with him for only a second, but what felt like an hour, and plunged down throat deep his entire cock gone in the blink of an eye, and she moaned, and how deep a moan it was as if it rattled from her core. And Johnny moaned. She loved cock, but this one felt so... inexplicable. Everything about it was magic.

Johnny looked down and watched as his cock disappeared into his gorgeous sister’s mouth, his first mouth ever, and so effortlessly, pops, and rings and sparks ignited in his head, heart, ears and toes.

The fireworks went on, and on as he watched his sister work his cock like she hadn't eaten in a week and his was the only food source around for miles. Kimmy felt every vein pump and loved every moment the head brushed up against her tongue and up and down in and out, she loved it, her heart was pounding and she would transition back and forth between his balls and cock. "Flash-click-click" went the camera, Kimmy didn't care. "Flash-click-click" several more times

Kimmy thought to herself, "he wants a show? I’ll give him a night he won't EVER forget!"

She grabbed him by the back of the knees and threw him onto her bed.

"She’s a lot stronger than she looks" thought Johnny as the sensation continued, and suddenly there was nothing at all. Johnny was terribly confused at the sudden change, looked down with his knees in the air and his sister, face down ass up, that thong sticking up like a slut's flag. They made eye contact once again. She put her fingers to her lips and "Shhhhh...." and winked at Johnny. Johnny had no idea what was to come. Kimmy had only fantasized about this, heard her girlfriends whispering about it, and watch videos of it, but now, in the heat of all heat she dove in tongue first.

Johnny yelp and suddenly as her tongue invaded his asshole, swirling and washing away everything that was innocent about him. He was forever changed at that moment on, he and his sister had formed a bond without words that was going to follow them for the rest of their blessed lives, and they loved it. Kimmy spent a good 10 minutes tonguing her little brother and could tell that the time had come. She got back to work on his cock, deep throating, and licking, sucking and sucking. Massaging his ball sack and fingering his freshly saliva lubed asshole.

Johnny could feel the cum working up about ready to exploded, and right as he was about to cum Kimmy pulled up for air and cum followed her mouth shooting right in choking her wind pipe temporarily, one thick puddle landing on her nose under her eye. She swallowed the cock and dumped the rest on her tongue, savoring the flavor. When Johnny was done and drained, he whispered, "don't swallow it, yet," Kimmy obediently didn't.

"Open up your mouth"

Kimmy obeyed "Click-click-click" went the camera

"Ok swallow." As she swallowed Johnny was taking a video from open mouth to swallow to open mouth again watching as his seed was ingested, wiped off her face with her finger and every last drop accounted for. She gave the camera one last giddy grin and blew a kiss to it

Kimmy and Johnny, both spent, took a shower together and cleaned themselves off. Giggles and petting, kissing and groping, they eventually made their way to bed before the sun was about to come up. Lying in each other's arms Johnny whispered "you know this changes everything"

"Yes I do"

"I love you, Kimmy"

"I love you, Johnny"

"We can play dress up anytime you want to"

"I’d love that" And they fell asleep...
1 comments

freshkissReport 

2021-05-13 14:46:05
what guy wouldn't want to let his sister play dress up with him, especially when sex is involved and picture taking whether for kinks or for blackmail which is also kinky. my brother was all into my kinky games with him, even when i eventually blackmailed him into being all mine. like all horny boys he went wholeheartedly into it. i still play with him even after ten years of doing it.

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