Trans Sister

Summary: Sister spends summer with brother and roommates and...

Note 1: Thanks to Breezy and Amy for coming up with this wickedly fun tale.

Note 2: This is Summer Lovin' Story Contest 2022 so please vote.

Note 3: Thanks to Tex Beethoven for editing.

Trans Sister

"Jesus Christ, Steven," Mike sighed, encountering his brother in their living room wearing a dress.

"Mike, please don't tell Mom and Dad about this," Steven pleaded, totally mortified to be caught in his Mom's dress, which thankfully didn't reveal he was also wearing her bra and panties.

"Why the fuck are you wearing a stupid dress?" Mike asked, staring at his brother, his polar opposite in almost every conceivable way, wearing a pink flowery dress... fuck, he was even wearing pantyhose... or at least some sort of hosiery!

"I just wanted to see what I looked like in it," Steven said.

"What you look like is a cross dresser," the older brother said, "and so long as you're wearing that outfit, you actually are one," having now encountered yet one more reason to be embarrassed by his younger brother.

Mike was a senior in high school, and Steven a junior.

Mike was an athlete who played football, basketball and track; while Steven was a 'math-lete' (an actual term that made Mike want to vomit).

Mike was six foot two and built with muscles everywhere, just like their father; while Steven took after their mother and was skinny, with a shapely ass, athletic legs and full lips.

While their father was an influential sports agent whose clients included many of the top athletes in the NFL and NBA, as well as a few MLB and NHL ones, their mother was a former Ms. South Carolina, who owned (and ran) a yoga studio.

"I guess I was just being silly," Steven said, secretly pretty sure he was gay, and even more certain he'd been born as the wrong gender. Although he unmistakably had a penis, he'd always felt more feminine than masculine. He frequently wanted to wear girlie things and do girlie things.

"And are those Mom's pantyhose?" Mike asked, secretly having a thing for pantyhose (gawking at, not wearing), which was likely his mother's fault, since she wore them regularly, and was considered the hottest MILF around by his friends.

"Y-y-yeah," Steven stammered, embarrassed by the disgusted look on his older brother's face. He idolized his brother, but there was no way he could emulate him, and he feared this confrontation could drive an even deeper wedge between them.

"Just get out of that girly outfit and store it somewhere discrete before they get home," Mike said, shaking his head as he stalked out of the room mumbling, "Fucking sissy faggot!"

Yes, it was a disaster! Ashamed, Steven changed out of his mother's clothing, swore 'never again' to himself, and for the next year he managed to suppress all of his desires to be more feminine.

But once Mike left for college, Steven could no longer set aside his temptations or deny who he truly was, and he began wearing panties all the time... pantyhose sometimes. He watched YouTube tutorials on applying make-up, and practiced in the privacy of his bedroom.

So when he reached eighteen, Steven officially came out of the closet as gay, but still not revealing his cravings to be more feminine, since that extreme would be too shameful for anyone to accept. Neither his mother nor father were surprised about his being gay, although his father didn't approve of it at all. Although he was well aware of his father's homophobic views, he'd long been struggling with who he was, and had finally decided not to deny his inner truth just to appease his father. But this struggle turned out to be both tragic and ironic, since shortly after he came out, his father died in a plane crash, incidentally leaving the family very well off.

And shortly thereafter it was his mother who insisted he stop denying his inner self. One day a couple weeks after his father's passing, she sat him down next to her on the living room couch for a 'serious talk', and immediately asked flat out, "Steven, are you just gay, or is it more? In your heart are you actually trans?"

"Mom?" Steven asked, shocked by the question. It had come right out of the blue!

"Honey, I know you've been wearing panties and nylons for a few years, and it's obvious to me that you wish you were a woman," she explained.

Steven broke down in tears. He'd thought he'd always been so discreet!

"It's okay, honey," the mother said, compassionately grasping her son's hands, the son who might soon become the daughter she'd always wished she had, and comforted him (or her, she wasn't quite sure about which pronouns to use yet), "I told you this would be a serious talk, so here's the serious part. I want you to think long and hard about whether you want to go through life as a man or a woman. The decision is entirely yours, and I'll love you with all my heart no matter what you decide. But it will be my honour to pay for the drugs and operations if you decide you do want to transition into being a female."

"Y-y-you will?" Steven stammered, as he wiped tears of joy and growing comprehension from his face. "And you'd still love me?"

"Yes, honey, always and no matter what," she assured him. "It's time you started living as the real you... whoever you decide that should be."

"Oh Mom..." Steven began, but then got all emotional and couldn't continue speaking, as his mother wrapped her arms around him.

"I know, honey, I know," she said.

"Thank you," Steven was able to muster... having been depressed for a while, and had even had the odd suicidal thought because of not being able to be who he felt he/she was.

After two or three minutes, perhaps more, he finally responded. "If you'll support me, and I don't mean just financially, there's no question: I'd love to become a woman."

There was another long silence before the Mom asked, "Then the next question is what should we name my daughter?"

"Oh, Mom," Steven broke down again, this time in a combination of tears and giggles. He'd secretly called himself Stacy whenever he did the odd online roleplaying or left online comments for an author he followed on Literotica... a website where he'd found some erotica that spoke to him.

That had been three years ago.

Steven was now Stacy. The seemingly endless transition had been expensive and time consuming... but now at twenty-one, Stacy was all female... well... except for the seven-inch penis she retained. She had perky B cup breasts, long blonde hair, shapely legs, and an ass that was to die for. Unless you knew Stacy back when she was Steven, there was no way you'd have a clue she used to be a male... other than the Adam's apple.

While Steven had been quiet, reserved and an introvert, Stacy was outgoing, wild and an extreme extrovert.

While Steven had been a wallflower who avoided attention at all costs, Stacy basked in the excessive attention she received whenever she went anywhere. She was beautiful, had a great body, and she flaunted it well. Tight dresses that showcased her ass and tits, and she almost always wore nylons... something she'd learned from her mother.

In short, back when she was presenting herself to the world as a guy, she'd felt that in order to hide her inner self from the world, she had to do her best to hide herself (or himself, if you want to be literal) completely. But now that she was presenting the beautiful woman that she really was to everyone, what was the point in hiding at all? So now she was open and gregarious and having the time of her life!

It's probably worth mentioning that she was also bi. Or at least she was in theory, since she was still a virgin, according to all definitions of the word.

Of course Mike was aware that his brother was now technically his sister, and although he hardly talked to her at all, He struggled to think of his brother as a she... he hadn't seen her since Christmas over six months ago, and while his brother had been obviously turning into a female, and a pretty one at that, he still couldn't wrap his head around the idea that any self-respecting guy could ever decide to become a girl.

Steven had been a virgin. Stacy was still a virgin.

Both Steven back when he was a male, and Stacy once she became who she now was, wanted to lose her virginities. She also wanted to be fucked... and as twisted as this may seem, it was always Mike, her brother, who popped into her head as she stroked her cock. She knew it was wrong, although she also knew incest was a lot more common than most people would think... and that many boys and men fantasized about having sex with a family member... usually the mother (who she also fantasized about). She never thought that would actually happen, since she knew Mike was still disgusted by her decision to become a woman. So she did her best to push those fantasies of getting fucked by her brother and fucking her mother out of her head, and instead she focused on attempting to lose both of her virginities.

While Steven had lacked enough confidence to make it happen, Stacy knew she had the aura to make it happen pretty easily... she knew that both men and women now tended to drool over her. She knew she could get fucked in a heartbeat... but her one remaining insecurity was about what might happen when her sex partner discovered she had a dick. This concern had stopped her from doing anything more than flirting and teasing... until the summer of 2022.

Mike was less than thrilled when his mother told him that his sister (Mom always referred to Stacy with a feminine pronoun, which Mike still couldn't manage), would be coming to stay with him for the summer in Florida... Mike was going to be a senior this fall at FSU. Although Mike tried to protest, his parents (before his father passed) had rented for his use (and for a couple of his teammates) a plush beach house right on the ocean near Tallahassee (actually in a small coastal town called St. Marks)... so it really wasn't his house, and therefore it was his Mom's decision to make, not his.

Mike had lots of concerns about this extended visit.

One: his brother (sorry... sister) would almost certainly cramp his and his roommates' lifestyle. All three were ladies' men, and they often brought women to the beach house for orgies, gangbangs and so forth. Sometimes they were students, often they were MILFs, and occasionally even faculty... all of them mightily attracted to three big-dicked studs with massive reputations. While Mike was a star running back, his roommates were also studs. Malik Green was the team's starting quarterback, and Ricky Denton the team's all-star defensive back.

Two: he had no idea how to talk to his 'sister'. For starters, could he call him/her Stacy without barfing?

Three: if the truth about her transgender status came out, it would be super embarrassing... so it was likely better just to reveal that detail to his roommates up front, and say nothing to anyone else.

Four: his roommates would likely not appreciate having a trans living in the house all summer. Would they need to rent a hotel room every time they wanted to host a party?

Mike spent a couple days warning his roommates about the situation, and they both expected the worst... until she arrived... a few hours early... Stacy wanting to surprise her big brother.

When Stacy knocked on their door, it was Malik who opened the door and gasped. "H-h-hello, h-h-how may I help you?" He stammered as he stared at this beautiful white woman wearing a red dress and black nylons... nylons not something he saw much of in the Florida heat.

"I think you might invite me in, silly," Stacy responded with a broad smile in a sexy voice. "I'm Mike's sister, Stacy."

"You're Mike's sister?" Malik asked, taking in this stunning beauty, and finding it impossible to believe this sexy bombshell used to be a guy.

"In the flesh," Stacy smiled, loving the look of lust and admiration she was receiving now and had been receiving for the entire day. At the airport, on the airplane, leaving the airport, and in the Uber that brought her here.

"Well, come on in then," Malik said, still a little stunned at the living, breathing sex appeal standing right before him.

"Thanks, darlin'," Stacy said, leaning in and kissing his cheek, allowing her sensuous perfume to swarm around him while briefly allowing her small but very firm breasts to rest against his muscled chest... this black guy was fucking hot!

"Yeah, no problem," Malik said, realizing his dick was rock hard. She's a guy. She's a guy! She's a guy, he kept reminding himself as she sauntered past him and he checked out her booty ... her ass was utterly amazing too... no way had that ass used to be on a guy, as the short dress floated up just high enough to give him a quick glimpse of it.

"Holy shit," Ricky said, wearing just trunks, heading for a dip in the ocean.

"Likewise," Stacy shot back, ogling the perfect sixpack.

"Who is this beauty?" Ricky asked, his dick instantly hard, as he admired this blonde bombshell.

"My brother, I'm afraid," Mike sighed as he walked out into the common area, also wearing just a pair of swimming trunks... although he too was shocked by the pulchritude he was encountering. His sister wasn't just hot... she looked exactly like their mother... the only MILF he could never have... and the one he fantasized about the most.

"This is your brother?" Ricky gasped, the babe standing before him looking 100% woman.

"Yeah, he is," Mike said, trying to hide his astonishment at how much she resembled their mother, and he managed to sustain his disdain at him (damn it!) for transitioning. "Yours is the last room on the right."

"Thanks," Stacy said, loving the reaction she was getting from the two roommates, but she'd been hoping for a much warmer greeting from her brother.

"Yeah, whatever," Mike said. "I'm going for a swim. Are you two coming?"

"Uh, yeah, okay," Ricky said, still trying to process that this hot chick, perhaps the hottest he'd ever seen in person, and he'd fucked a lot of hot chicks, was a guy, and he probably had a dick.

"Nice meeting you," Stacy said, as the two hot men followed her brother out the door... although each of them checked her out one last time.

Over the next few days, Stacy was always dressed in sexy attire. Miniskirts, tube tops, nylons... the two roommates were constantly checking her out, as did anyone she encountered nearby... but she was dissatisfied... desperate to get some positive attention from her brother. She couldn't explain why, but she still needed the approval she'd never gotten from him... both as a sibling when they were much younger, but more recently, also as a sexual being.

Mike, on the other hand, could barely look at her. You know that tension you feel when someone is so attractive that you struggle not to stare at them? And then that other feeling when they're so repulsive that you can't stand to look at them at all, but you don't want to be overly rude? Well, Mike kept going back and forth between both of them.

Mike also always called her either Steven or bro. He did this for a couple of reasons. First, he still struggled with his brother being a woman... and although he wasn't against trans people or the LGBTQ+ community in general, and although he'd been vaguely aware of hints throughout almost his entire life that his brother was different (and thus embarrassing), it just felt weird when it was his own brother.

Second, and very confusingly, his brother was hot... like ridiculously hot. He (definitely he) had a tight body, perky tits, a great ass, and long legs... often in nylons. Although very few girls wore them in Florida, the MILFs at the bars often did, and he gravitated to them. There was just something about a woman in nylons.

Third, he couldn't help seeing how much he/she looked like their Mom.

Fourth, during the past two nights he'd had dreams about fucking his brother... with his woman's body... waking up rock hard, and mortified by his own sick, twisted thoughts.

On Friday, Ricky and Malik were chatting about a party they were going to that night, and Stacy asked, "May I come?"

"I don't see why not," Malik shrugged.

Ricky added, "It's at another beach house."

"Cool," Stacy said. "So it's bikini attire?"

"Definitely," Malik nodded, surveying the hot blonde... the one he'd jerked off to every night since she arrived.

"I bet you boys can't wait to see me in a bikini," she flirted.

"Ya got that right," Ricky agreed. Neither of his roommates knew he was bi. He didn't find men particularly attractive, but he loved the look of a well-hung cock. Loved it in his mouth, loved one in his ass. This was his well kept secret... but the secrecy was becoming more fragile with the trans Stacy sauntering around the house in those cute, lightweight dresses. He was dying to know how big her cock was. Although he liked sucking dick and getting fucked by guys (usually older bears, but a couple of twinks had really fucked him good too), and for him the idea of a trans was a real turn on.

"Wait here," Stacy said, really enjoying the attention she'd been receiving from her brother's two hot roommates, and although Mike would deny it, she knew her brother had also checked her out more than once... especially her legs in nylons, which she'd worn every day since she'd arrived... since she knew he had a nylon fetish.

Five minutes later, Stacy returned in a pink bikini, and she asked, turning sideways to offer the boys a good look at her cock, that couldn't be totally hidden inside the bikini bottom in its hardened state, "What do you think?"

"Jesus!" Ricky said, his eyes going directly to the hard cock peeking out of the bikini bottom... a cock that looked incredibly impressive and inviting.

"Shit," Malik said, admiring her perfect breasts... not too big... not too small.

"Is that good 'Jesus shit' or bad 'Jesus shit'?" Stacy asked, although from their tone of voice and the look in their eyes, she knew the answer.

"You look amazing," Malik said, just before his eyes headed further down, and he too caught sight of her cock.

"Yeah, there's no way I'd know you used to be a guy," Ricky said, as he imagined that seven-inch cock inside his mouth or his ass.

"Yeah, except for that huge dick you're packing," Malik said, thinking it so surreal to see a massive hard-on tenting out the pink bikini, but attached to a body he'd love to fuck.

"I have a skirt to help conceal my bottom half," Stacy said. Only my good friends are allowed to see my dick."

"Jesus Christ," Mike said, walking in and seeing his brother's dick poking against the bikini.

"Hi, big brother," Stacy said, going to him and pulling him in for a close, flamboyant hug.

"Get off of me," Mike said, pushing her away, even as he felt his dick hardening.

"Sorry," Stacy said, hurt by the rejection. Yes, as has been said, she loved the attention she received from the two roommates and from other people in the area, but what she really wanted was approval from her big brother... even just a little of it would help.

"I'm sorry too," Mike said, seeing the hurt in Stacy's eyes.

"Why do you hate me so much? Is it because I'm no longer a man, or because I never really was one?" Stacy asked, with tears forming.

"No," Mike said, realizing his poor treatment of her was unfair. It was 2022 after all, and unbeknownst to his buddies, he'd been with a trans woman once. He'd even sucked her cock for a while, and found it stimulating, even though it made him feel like less of a man. He stopped after just a couple of minutes, and then he fucked her good, in part to compensate for his lapse. He finished by depositing a load deep in her ass, which triggered the trans woman to come all over the sheets.