The Scholarship

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Sorry," Maggie said, "But as you can see, we were rudely interrupted."

"Sorry," Stacy blushed, seeing her brother in the altogether. "I can..come back later."

"It's no problem," Maggie said. "We are practically family."

"Later would be good sis," Tracy finally managed. He'd never been so humiliated in his entire life.

"Don't be rude Tracy. Let's hear what your sister has to say," Maggie said. "It could be important."

It was important. Tracy knew his sister must be here to try to reason with Maggie. Girl to girl. However, he was tied up, and wearing nothing but stockings and heels. Worse, than the fact he didn't have on panties, was that he was still taped. His crotch was a smooth as any girl's.

"Now is okay," Stacy continued with a gulp and quick glance at her feminized brother, her mouth suddenly dry. "I wanted to uh talk about Tracy."

"Ahhh," Maggie said. "Our Tracy's little problem?"

"Yes.."

"Speaking of problems, aren't you on scholarship too?" Maggie asked. "How do I know you don't have the same problem."

"Don't be ridiculous," Stacy said.

"No more ridiculous than Tracy here. Just look at those cute little breasts. And that sexy little puss. Only a thorough examination would prove what he really was." Maggie said. "So, what I'm saying is. I guess I need some sort of proof that you are what you say you are."

"But.." Stacy broke from the girl's harsh stare. This wasn't going how she planned at all.

"You strip. I'll make myself comfortable." Maggie ordered, as she mounted Tracy once more, this time mounting him reverse. Burying his soaked face in her rear.

"Is your mouth tired baby? Maggie asked. "Maybe we can play with Mr. Friendly while you take a rest."

Tracy burned bright red at the suggestion. He'd been hesitant to lick the cruel girl as he hated this position. He'd have to tilt his head painfully in order to lick her sex, and even then, his nose would be buried in her other hole. Worse was the knowledge that his sister would see him doing it in such a fashion and she might assume he was licking her rear as well. However, there was only one thing more humiliating than that, and that would be getting fucked with the strap on cock she called 'Mr. Friendly' in front of her. He sighed and commenced to licking with renewed vigor.

"Good girl," Maggie said, "That feels real nice." To Stacy: "Slowly Stacy, we are in no hurry here. We have all afternoon."

Stacy obeyed the bossy brunette, while growing more and more embarrassed by the second. It wasn't so much the stripping. It was the fact that her brother was going to see her naked. Worse, that he'd see that she was aroused. God, seeing her brother tied up to the four corners of his bed while laying there helplessly beneath that girl. Dressed in pumps and a cute pair of panties. His crotch, emasculated and as smooth as any girls. He even had his hair trimmed into a sexy little landing strip. On the bright side, it could be worse, with her brother's head buried in Maggie's rump, there was no way he could see her there in her altogether.

"Satisfied?" Stacy asked with more confidence than she felt. Chill bumps covered her from head to toe. Her face and breasts flushed from her unwanted excitement.

"Not yet," Maggie said, reaching down and running a finger along Tracy's makeshift slit."I can do the same thing with Tracy with a little bit of tape. Let me see the inside."

Oh God. This was certainly going to far. However, there was something about being naked that made her feel a bit more - compliant. There was no help from her brother, that was certain. God, he was so..embarrassing. With nimble fingers, Stacy reached down and spread her nether lips. It was worse - so much worse than being at the gynecologist's's office.

"I guess you are a real girl after all," Maggie said. "But your little brother is almost worthless. He's never going to bring me off at this rate. Be a dear and look in my top drawer there.

Stacy opened the drawer and her eyes grew wide at the contents. Imagining what they were used for made the fire in her loins rage bright.

Poor Tracy licked for all he was worth. Oh how he licked. He even licked places he'd never licked before. Her asshole. It was a bit musty, but he went at it. Anything to get his sister out of here. It was bad enough his sister had seen him thus. Much worse for her to see the contents of the drawer and know what sort of things he did with Maggie. Or the things she did to him.

A crop. Clamps. A paddle. Vibes. Dildos. Some very realistic. Some - some even appeared to be fashioned in such a way to be worn by a girl.

"Pick one," Maggie ordered. "Something you think will encourage your little sister to be a good girl."

Being made to chose. Whatever she picked would be used on her brother. She could pick something easy like the large feather or something cruel like the paddle. Whatever she chose - it would label her in Maggie's eyes. She could...but she couldn't. Her hand closed around the most perverse of all. She could see the laughter in Maggie's eyes - or was it victory. Whichever the case, there was no help for it. She handed it to the cruel girl.

"I'm not going to use it," Maggie said triumphantly. "You are. Bring the clamps too."

Oh God. It was terrifying yet thrilling at the same time. She heard her brother's muffled protestations. She ignored them, pushing one end of the cock inside her and strapping herself into the harness.

"Don't forget to lube." Maggie said. "It's in the drawer."

She watched her brother struggle against his bonds as she lubed up the phallus.

Stacy positioned herself between her brother's legs. It was so very hard to imagine the body beneath her as masculine. Those long lean legs, the white stockings, the heels, the small breasts. A swollen slit was all that remained of his manhood.

Stacy had never done anything like this before. Sure, she'd had sex. But she'd always been the screwee, never the screwer. It was more difficult than she figured. She had to sit back on her haunches and scoot forward. Ahhh- there it was....

"Oh she's licking now," Maggie purred. "Her tongue is like a tornado. And you wouldn't believe where she's licking right now-mmmm...that dirty dirty girl has her tongue right up my butt. Gawd, it's right up my asshole. Stacy, do you still think it's necessary to - you know - mmmmm - to spur her on?"

Poor Tracy hoped briefly, that his ordeal would be over. Surely his sister wouldn't actually do what it was that Maggie had suggested. However, the question was rhetorical. Trapped beneath Maggie, Tracy couldn't see the determined look in his sister's eyes. However, he soon felt that determination against his tender rear opening.

"Mmmmmphhhh..." Tracy protested, his words dying in Maggie's drenched sex. Struggling was useless, tied up and spread eagle. He tightened his rear, body had changed so much over the course of the semester. In the beginning he may have put up a fight, may have resisted a few moments. However, his bottom was no longer virginal, it had been stretched often and thoroughly. Though he wanted to resist, his body yielded, accommodating the phallus in one smooth stroke.

There was worse to come. His nipples were clamped one by one. And the chain was being pulled with his sister's every thrust. He was forced to move with her motion, to work himself on that hard phallic invader.

There was nothing Tracy could do but lick. Lick whichever hole Maggie liked. And right now that was her dark nether hole. Lick and take it, his neck bent at an aching angle. His sister was really plowing into him. It felt good. The worst was the knowledge that this forbidden pleasure was being administered at the hands of his sister.

Don't think of that, not her, not like that he told himself. He discovered something worse than being taken by his sister. The tape that hid his cock was ripped off one piece at a time. He groaned from the aching pain as his balls distended. Soon after, nature took over. No. No. Not now. But it was too late. He was hard again and he wasn't sure who was jacking him off. Was it Maggie or was it his sister?

Please not my sister, he prayed. Oh God, he could feel his come rising. What if it was his sister with her hand wrapped around his cock. What would she think of him laying there tied up, all dressed up in girly lingerie, his face buried in his girlfriend's bottom, while his sister was buried in his. Worse, what would she thing- if he - if he?

He balls surged. His thighs spread wide as his narrow hips flexed. It felt like gallons spewed forth, but it was only a small trickle. Maggie captured the discharge on her finger, then held the pearl of fluid to Stacy's mouth. The girl belonged to her now, as did her brother. She'd toyed with the girl while she pumped her hips, taking her brother. She teased the girl's nipples, even pinched them cruelly.

But that was too much for the girl. Stacy protected her chest and the look she gave was that any more of that wouldn't be allowed. It was disappointing to be sure, but hardly a surprise.

Maggie shrugged, taking hold of the chain connected to Tracy's aching nipples and pulled. She felt the groan of anguish against her tight rear hole. Ah, yes, there was still one sister she owned.

Maggie kissed Stacy while she pulled the chain in another direction. Kissed the girl deep. Bit her lips. She smiled as the girl licked the bitter pearl of cum from her fingers. Stacy hesitated briefly. This was her brothers come. She couldn't. Yet, she opened her lips and took it all, her eyes rolling back in her head as she sucked hard on the finger in her mouth. Slim hips pumping hard as her orgasm slammed into her like a home run.

Something else slammed home as well. Slammed home with the bright flash of a camera. The knowledge of what she'd done. That it was taboo. That she shouldn't have given in to temptation.

"No..." Stacy protested, but it was far too late.

Flash! Flash! Flash! Maggie giggling the whole time.

Capturing her between her brother thighs. Blushing. Naked. Post climax. Hands covering her face - but it was far too late. Extricating herself- phallus sticking out from her thighs. Hands trying to cover it - but it was far to large for such small hands.

"Just a little insurance," Maggie laughed. "Nothing for either of you to worry your pretty little heads about about. As long as you do what I say. Say Stacy, what are you doing tomorrow?"

"Nothing," Stacy replied reluctantly.

"Well, I've been wanting Tracy to get a tattoo," Maggie said. "A pretty little butterfly on the small of her back. A little something that would make sure no one ever doubted he was a girl."

Maggie untied her feminized charge and held him in front of her, his rear facing his sister, while tracing the small of his back in the design of a butterfly- a design a bit larger than she let on.

"Please love," Tracy whimpered. "Needles frighten me."

"Or do you think I should give him one on his ankle instead?" Maggie asked. "I want you to pick which one. If I like your answer, we can delete one of the pictures we just took. Guess wrong and we can keep it awhile longer.

Stacy bit her lip as she looked at her brother's cute bottom. God the way the girl was palming those alabaster cheeks so possessively. Her brother standing there in stockings, garters, and a pair of high heel pumps. His cock was visible now, but she could never imagine him as being masculine again. Not after what she'd seen. His blue eyes looking back at her so helplessly.

A picture. How many did the girl have? She could see from the look in Maggie's eyes what the girl wanted her to say. God, but she felt so guilty. She'd be betraying her ... it was so hard to think of the dainty creature in front of her as her brother. Yet, they were family. She should...oh but the way her insides melted. God, she couldn't. She didn't dare.

"On the back."

Maggie said, teasing Tracy's nipples with one hand, while cupping his balls with the other. "What is a tattoo like that called Stacy? Doesn't it have a name? I seem to have forgotten it."

The words words were hard coming, Stacy's tongue didn't want to work. "A tramp stamp." she stammered.

"Mmmm...I like the sound of that," Maggie said. "Okay, I'll delete one of your pictures. You can go now."

"What do you think Tracy?" Maggie asked her hand moving down to his hard cock, catching it between her forefinger and thumb and jacking him slowly. "Your sister thinks it's a good idea too."

"Please Maggie," Tracy begged, his chin trembling and tears welling in his eyes. "I'm scared of needles." Not just needles but having a permanent tattoo.

"But it would be sexy," Maggie said. "You want to be sexy for me don't you?"

"Yes..but.." Tracy wiped the tears with the back of his hand. God, what she was doing down there felt good. Not good enough to make up for a tattoo, but so very good nonetheless.

"But what if I don't like it later," Tracy said. "It's be permanent."

"They can take it off with lasers these days," Maggie said.

"Please," Tracy begged. He couldn't even manage to stand due to Maggie's stroking. He went down to his knees. "Anything else."

"Why are you going down there?" Maggie asked playfully. "Did I say you could lay down."

"No," Tracy said, and tried to get back up on his trembling legs, but couldn't quite manage. Instead of standing his thighs spread on their own volition.

Maggie smiled and got on top of him. Positioning his hard cock against her wet furrow.

"And you don't have to get a tattoo if it scares you," Maggie said. "If I'd known you'd be so frightened, I would have never mentioned it. I just wanted you to be sexy for me."

"I want to be sexy for you," Tracy gasped. He did. Maggie wiggled her hips and he could feel himself slide into her entrance. She made it sound as if he were scared of being tattooed. No, he was just scared of that one. A tramp stamp. No, he couldn't.

How about if I got you one of those fake tattoos?" Maggie asked. "Would that be okay?"

"Mmmm...yes..." Tracy breathed. God he could feel her hot sex dripping on his hard shaft. His head right in her opening.

"A pretty butterfly," Maggie said. She wriggled more, he was in her now. "Will you do it for me?"

"Yes." A temporary tattoo was nothing. Of course Tracy could.

On Monday he wouldn't be quite so convinced. Not when we went to class with a pretty little butterfly on the small of his back. Easily seen in his shirt that bared his midriff and a tight pair of shorts. No, on Monday, his cheeks would blush all day. He wouldn't meet anyone's eyes. It wouldn't matter if the tattoo were real or not, the effect would still be the same.

Which was one of Maggie's goals. To have Tracy all to herself. She wriggled her hips again and her insides danced when Tracy's legs spread and he wrapped his knees around her back.

It was a position no boy would ever take with a girl. No, a regular boy would grab her by the hips while he humped his own. He'd take control, even from the bottom.

But not Tracy. Tracy was active in other ways. Femmy ways. He rubbed Maggie's shoulders...her ass. He kissed and sucked her nipples. He moaned in her ear. He gave pleasure - he didn't take it.

"If you come inside me, you are going to have to lick it out. We still have to watch what we do you know."

Tracy nodded, his face a bright red.

"What's it going to be?" Maggie asked a bit harsher this time.

"I'll lick you after," Tracy whispered.

"I know you'll lick me after," Maggie said. "What I asked was if you planned to suck all that nasty come out of me."

"Yes love," Tracy breathed. "I'll suck my come from you after. God...just please..please...I'm so close."

Maggie grinned and bit her lower lip. She shifted her hips and tightened her muscles.

"Wait..wait..." Tracy moaned, his nails digging into Maggie's back. His loins surged, it was too late.

"Already?" Maggie mocked playfully.

Tracy's cheeks burned a bright red. Shallow grunts told the truth no matter if he kept his words locked behind his tightly clenched jaw. It was...magnificent. He'd never felt such a sensation.

"Don't worry baby," Maggie said. "I don't mind, so long as you remember your promise. And I expect a very thorough job to be done."

She straddled his body and worked her way up. Her hairy mound was drenched. Her purple hued lips were thick with lust and dripping with Tracy's premature ejaculation and her own secretions.

"I love you baby," Maggie whispered and sat down on Tracy's pretty face.

The sound was muffled but she swore he said he loved her too. Yes, tonight Tracy was getting twice her usual allowance. Mmmm..the girl had earned it.

The end

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
5 Comments
erins_Whoreerins_Whoreabout 3 years ago
Liked the story! ... Also...

I did really enjoy this story. But I wanted to state - this is clearly a work of sexual fantasy. This is NOT an example of a good relationship - in real life this would be a very very abusive relationship. So please don't think of this as an example of a viable relationship.

BrendaNWBrendaNWover 3 years ago
So very exciting

Thank you for a very well written story, please continue the story of Maggie, Tracy and Stacy. The pace and wording is just so good that I felt I was watching them, right next to them .. even fading into each character ..

secretLacesecretLaceover 8 years ago
You are the best!

We need a continuation of this master piece. The pace is perfect and you always had such a naughty imagination. Please please please!

YANKEE DANYANKEE DANover 13 years ago
Love your tranny stories

I skimmed alot in this story, I do that alot with the longer ones, but I'll be back read it all the through when I'm not in such a hurry :)

JentvcdJentvcdalmost 14 years ago
Really a Good Story!!!

Gots to say all your stories are Great,Love them all.

Share this Story

Similar Stories

Feminized By My Mother Ch. 01 Shemale mother makes son a sissy.in Transgender & Crossdressers
Party Slut Never fall asleep at parties!in Transgender & Crossdressers
Lesser of Two Evils A man's choices will transform him into a cum slut.in Transgender & Crossdressers
The Babysitter Babysitter guy becomes babysitter girl.in Transgender & Crossdressers
Turned Out A male college student gets used by a dickgirl classmate.in Sci-Fi & Fantasy
More Stories