Being my trans sister's valentine
It was about half past four, in the afternoon, when 13-year-old Boris came home after football practice. The raccoon boy steeped out of a family van, owned by one of his friends' parent and waved goodbye to his friends from the junior football club as they drove off.
Boris then entered his suburban house and dropped his sports bag just inside the hall. He heard the TV was on and knew it would be his sister watching, since both his parents wouldn't be home for a while. He then went to the living room, where sure enough his older sister was, 15-year-old Ivanna.
Ivanna was a very pretty raccoon girl with long, dark brown hair and beautiful chestnut colored eyes. She wore at that point, a blue denim skirt and a wine red blouse, in contrast to her brother's green football jersey and white shorts.
She looked however sad and Boris asked: "What's wrong? Is it a sad movie?"
"No, no its not." Ivanna said meekly.
"Has someone teased you at school?" Boris asked harshly and was ready to fight anyone who had bullied his sister.
"No, it's just that it is Valentine's day and I haven't got a date." Ivanna said a bit bemused at Boris reaction.
"Oh" Boris said a bit embarrassed, as he realized what day it was and that girls made a big fuss about it. However, Ivanna had not always been a girl, since she was born a boy and named Ivan. It however became more and more clear to the raccoon that she was a girl and started wearing girls' clothing. Ivanna's parents had been very supportive of her and instilled in Boris that Ivanna was his sister now.
Boris had no problems with that. He had of course been a bit confused in the beginning, but since Ivanna quickly started completely looking like a girl, he almost forgot that she was ever a boy.
Boris had only once called Ivanna a boy doing a sibling fight and instantly regretted it as he saw her hurt she looked, and he vowed never to do it again and to protect his sister.
"So, no one has asked you out?" Boris asked and Ivanna answered: "No. so I'll just have to spend the day watching cheesy romance movies."
Boris looked at his sister and thought she looked like a very cute girl and didn't know why anyone wouldn't ask her out. He hoped it wasn't because of her being a former boy. Boris then said: "I could be your Valentine, you know, just until mom and dad gets home. I can keep you company while you watch your movies."
Ivana looked at him and smiled. "You don't have to pity me. I'm fine. Besides, I'm your sister. Isn't there some girls in your class you can ask out?"
Boris became red I the face from embarrassment and said: "I just don't know what to say to them."
Ivanna smiled sympathetically at him and said: "Just tell them they look beautiful today and maybe ask them to come over and do some homework. There you can have a more private setting to maybe get to kiss them. That's how I got my first kiss, by a boy who invited me over to do homework"
Boris still looked embarrassed, so Ivanna said: "Fine, you can be my Valentine for a couple of hours. Maybe you can learn some things from the romance movies."
Boris then sat down next to his sister and started watching the movie with her. Boris didn't particularly like those movies but watched anyway to please his sister, who despite knowing how cheesy they were really liked them.
There was a lot of kissing scenes and Boris became a bit embarrassed. He knew that if he had been Ivanna's boyfriend it would be a time like this they would sit and make out, and the thought exited him. He tried to tell himself that it was only natural since Ivanna was a cute girl, but then again he knew it was wrong.
Boris began starring at his sister and became more and more filled with desire. His eyes wandered from her naked legs up to her short skirt which only covered her pelvis. Then he starred at the two A-cup breasts which were hidden under her blouse. And then finally he starred at her cute face with her beautiful eyes, her cute nose, her pretty hair and her soft lips.
His starring was however soon discovered by Ivana who asked curiously: "What are you looking at, Bo?"
"Nothing, nothing." Boris said embarrassed and looked away, but couldn't hide his blushing. Ivana however knew and said: "You starred at me, again. Don't you think a girl notices when a boy looks at her."
The teen raccoon boy felt very ashamed and Ivana asked softly: "You still haven't kissed a girl yet, have you?"
Boris shook his head and felt more uncomfortable, but Ivana asked with her soft girlish voice: "Do you want to kiss me?"
Boris was stunned as he looked at his sister's face and she looked serious, but then she said: "Or maybe you should just wait until you find a special girl for that special moment. You know what, forget it."
It was now Ivana's turn to be embarrassed, but then Boris said comforting: "You are a special girl to me, so I would like to kiss you."
The was an awkward silence for a moment before Ivana said: "Okay, but we got to keep it a secret."
Boris nodded and then saw Ivana close her eyes, pucker her lips and move her head slowly towards his. He then closed his eyes as well and then moved his head closer to her face. Then their lips met and the two of them kissed. For Boris, it was a magical moment as he experienced his first kiss, and he felt all warm inside doing it with a girl he loved.
Then the kiss stopped, as Ivana pulled away and Boris felt a bit disappointed that it didn't last longer. "Not bad for a first time kiss, brother." Ivana complemented.
"You were great too. I hope you will let me practice with you so more when I will begin to date so I can be good when I find my first girlfriend." Boris said happy and dazed.
"You want more?" Ivana asked and Boris nodded enthusiastically. "Fine, then let's tongue kiss this time. Just open your mouth slightly and let your tongue dance with mine." Ivana said seductively. Boris wasn't quite sure what she meant, but closed his eyes again and waited for his sister to take action.
He then once again felt his sister's lips on his, but then felt his mouth being forced open by her tongue. Boris let his sister's tongue enter his mouth and then caught on as he let his tongue wrestle hers.
The two siblings dueled tongues for a bit, during which they also started stroking each other's sides for added affection. At one point, Boris accidentally went a bit too low and touched his sister's butt. He immediately pulled away, but Ivana took hold of his hand and placed it back on her behind. Boris then gave it a playful squeeze and Boris then felt Ivana groan softly into his mouth.
The two raccoons continued kissing for about a minute, all the while Boris continued groping his sister's ass. When they finally broke apart, Ivana playfully said: "My little brother is a bit of a pervert, since he likes to grope his sisters butt so much."
Boris grinned sheepishly and said: "Well, you liked it very much too." Ivana looked a bit embarrassed but smiled at him none the less. Boris then looked a bit down and saw the small mounds on Ivana's chest and asked nervously: "Hey, can I, can I touch your boobs as well?"
The question shocked Ivana for a moment but then she gave a sly smile and nodded. Boris then excitedly placed his hands on Ivana's two small breasts and began feeling them up through Ivana's blouse and bra. the older sibling didn't want to show how much she enjoyed it, so she suppressed her moans. She however wanted more, and felt herself embarrassingly grow hard. She then finally said: "Do you want to touch them directly?"
Boris looked up at her sister to see if she was serious, and since it seemed that way he nodded his head. He then helped her sister get the blouse of her and removed her plain white bra to reveal a pair of small A-cup boobs. "They are not that big, given my condition, but maybe they will grow bigger from the estrogen pills or I maybe I can get a surgery one day." Ivana said apologetic, but Boris found them perfectly fine. His hands quickly went back to fondling the now naked mounds and then he dared to go further as he went in and started sucking on one of his sister's tits. "Damn bro, you are kinky." Ivana moaned happily as Boris was giving her even greater pleasure.
Boris himself was also getting a raging hard on and hoped Ivana wouldn't find out. But then, as the two siblings grinded against each other, Boris erection accidentally hit Ivanna's erection. The two raccoons looked at each other in embarrassment and shame and quickly scooted away from each other to sit at each end of the sofa.
"We should stop now." Ivana said.
"Yeah, you are right." Boris conquered.
The two then sat in awkward silence for several minutes, which felt like an eternity, their eyes demonstrably fixated on the TV so they didn't make eye contact.
It was Boris who first broke silence and shyly stated: "You are still topless."
"Oh, yeah, so I am." Ivana shyly answered back.
"They look nice." Boris said as he handed Ivana her bra and blouse and she gave him a smile as thanks.
She didn't however put her clothes back on, she sat quit for about a minute and then said: "I could give you a blowjob if you want."
Boris was stunned and looked at to see if she was joking, but the cute raccoon girl just gave a flirtatious smile and appeared completely serious. The boy knew it was taboo to have any sort of sexual interaction with a family member, but then again they had done a lot of taboo things already. His dick gave strong twitch at the suggestion and it was impossible for the hormonally charged teen not to be enticed by the offer. The raccoon boy then gave a soft nod and Ivana gave a wide grin at his permission
Ivana then got off the sofa and down on her knees in front of her brother. She then gently tucked down her brother's shorts and underpants to his knees. Boris became a bit embarrassed to have his genitalia exposed to his sister as he had a slight fear that Ivana would disapprove of it, but Ivana just looked hungrily at it. The raccoon girl was horny and was aching for a cock and her brother's would do.
The penis had gone a bit soft doing the period of awkward silence, but Ivana had her feminine ways of changing that. She reached out and let one hand gentle message her brother's ball and then used the other hand to gently coax the sheath to get the dick out from its hiding spot. Boris gave out soft moans and said "That feels so good, Ivana.", and Ivana smiled at her efforts being appreciated.
Once the dick had finally emerged, Ivana bended her head down and without any hesitation let her brother's dick enter her mouth. Boris began groaning and Ivana felt flattered that she had that much of an effect on her little brother.
As Ivana kept blowing her brother, more and more pre-cum emanated from his cock and Ivana greedily sucked up every drop of the delicious nectar. Sucking cock was actually her favorite sexual escapade, since anal sex did give a sore bum. She did like taking in the ass still, and while Ivana was blowing Boris she stuck two fingers in her butt and started fingering her boy hole.
For Boris this whole experience was completely new. Before that day he hadn't even kissed a girl and now had he not only kissed one but he was also receiving oral sex from one, that it was his sister both made it better and worse. He knew it was taboo, but on the other hand it felt naughty and he knew he could trust Ivana not to do anything he didn't actually want.
Ivana kept blowing him for several minutes and he felt his orgasm, but then to his dismay she stopped. "Why did you stop." Boris asked distraught and Ivana said cheerfully back: "I was just wondering if you wanted to shoot you load in my butt, I am kind of itching to get a cock up there and you have one."
Boris couldn't believe what she was saying, but nodded as agreement. Ivana then stood up, reached under her blue denim skirt, pulled down her thong from underneath it and then playfully tossed the underwear in her brother's face. She the raised her skirt to her midriff to reveal her own boner, which was the same size as Boris's. she then straddled her younger brother's hips, took hold of his cock and lined it up against her bum hole before slowly descending on the hot organ.
"So tight." Boris moaned.
"So hard." Ivana moaned back
Ivana then started going up and down on her Brother's penis, riding him gently at first, but then slowly raising the pace. Boris remained pretty passive as he let his more experienced older sibling lead the action.
An opportunity to do something more arose however when Boris's mind was drawn to Ivana's dick, which joyfully bounced on Boris's stomach as she went up and down. Boris then took hold of it and started beating the meat in a rapid pace. "No don't, I shouldn't have such a thing." Ivana moaned, but Boris ignored her as her feverously jerked his sister off.
The two siblings quickly worked up a sweat as their passions ran wild, and much against Ivana's intention it appeared she would be the first to climax. Boris's expertise in jacking his own cock off worked wonders as he was jerking Ivana's cock, plus adding the stimuli of the raccoon cock in her bum made Ivan's orgasm approach rapidly.
It therefore only took a couple of minutes before Ivana cried out: "I am going to come." As she then slammed down hard on Boris's cock, before erupting and shooting her load, which landed on Boris's shirt.
Boris looked his sister in awe in her afterglow as he just realized he had made her come, and before she had made him come.
Ivana panted for a bit as she caught her breath before apologetically saying:" Sorry for messing up your shirt."
"Hey, don't worry about it, I'm just glad to make you come." Boris answered back and smiled.
Ivana smiled back and said: "Well, time for you to climax."
Ivana then started riding Boris again, but Boris stopped her and said: "No, get off me."
Ivana looked puzzled and was about to ask why, but Boris caught her off by saying: "I just would like to take you from behind." Ivana looked surprised for a moment but then smiled and got off her brother.
They then got into position as Ivana bent down on the sofa and raised her ass and striped tail invitingly. Boris then got behind his sister and easily inserted his dick back I n the well-fucked hole, to which the two raccoon siblings gave a big groan.
"Ah, yes, fuck me brother." Ivana huffed.
"I will, sweet sister. You are a girl and your role is to take a man's cock" Boris moaned back in a dominating tone.
"Yes, fuck my pussy. My duty is to be mated with when a man desires pleasure." Ivana playfully said back.
Boris had been on the verge of coming for several times and he knew this would be it. His dick went feverously in and out of Ivana's bum hole and his balls bounced against his sister's and it was only a matter of time before he groaned out "I'm going to come." And then he erupted and shot his hot load of boy jizz deep inside Ivana's anal passage.
The two raccoon siblings then panted in the afterglow for a bit, with Boris still balls deep in his sister. He then slowly pulled out and saw his semen drip out of her opening.
Wanting not to mess up the living room and thinking his shirt was already messy, Boris took it off and handed it to Ivana so she could use it to clean herself up a bit.
"Thanks." She said exhausted after the ordeal and wiped herself off, and then used it as a seat cover as she sat back down on the sofa. Boris then pulled his pants back up and joined her and the two of them relaxed for a bit on the sofa.
"We should probably clean up and air out before mom and dad gets back home." Ivana said and Boris agreed tamely.
"We will probably never do That again." Ivana said.
Boris: "Yeah. Or until next Valentin's day."
Ivana smiled and said: "Or maybe your birthday or Christmas, if you do my house chores."
The two of them then laughed before getting serious and stated hastily cleaning up any traces of what had transpired on that Valentine's day.
The end.