The Scholarship

"Oh-oh-oh-God-oh here - here it comes," Tracy moaned, his legs dancing in the air. Pleasure surging like never before. Oh God, sweet release was his.

"I told you to tell me before." Maggie stopped jacking and glared down at her roommate.

"Ahhhhh..." Poor Tracy. The surge of pleasure died at his balls and they gave a lone spasm. A dollop of bitter cum landed on the back of his tongue. More please. Please jerk me - jerk my clit. Oh God. She looked at him expectantly. He gave a reluctant swallow. So thick. So bitter. So salty. His stomach threatened to heave, but his lust held him in check.

"Please love," he begged. "I'm so close."

"I asked you to tell me before you came, but instead you just start spurting away despite what I said." Maggie said. "I think I deserve an apology."

"I'm sorry love," Tracy said. "I'll do better."

Maggie licked Tracy's hairless cock to lube it up and then spit into the crack of his bottom. She resumed jacking, only this time she had another surprise in store. With her other hand, she pushed the tip of a finger into his tight little hole.

"No-oh please-" Tracy grunted, but his need was so great there was no force in his voice, only need.

"No?" Maggie asked. "Or did you mean more?"

No his mind plead. But "More." his body begged. "More oh God, please more." He was so close. So fucking close he was leaking. Dripping drip drop - drip drop into his mouth, forcing him to swallow more of his bitter seed.

Lightning danced in Maggie's loins. She'd never had anyone in such a precarious position. Never had such control over a person. Oh how she relished it. She pressed her finger home. That mouth and tongue had long since been hers, and now that ass was hers too.

Poor Tracy. It was an unexpected invasion. It was an unwanted invasion. It was - it was like a trigger. Violating him. Making his body feel ...invaded. The normal cycle of pleasure escalating to a peak no longer applied. It was far too late for that. The best he could do was manage to squeak out - "Ugh - coming oh God I'm coming...."

Tracy's eyes rolled back in his head as the wall of pleasure slammed home. His ass spasmed, tightening around the invading finger. He obediently held open his mouth as rope after rope of slimy jizz shot out catching most, but not all - praying that this time, despite the fact that he hadn't followed orders that Maggie would not stop short once again.

"Swallow it baby," Maggie urged. "Swallow all that nasty come."

Tracy obliged. He had no choice. He swallowed and prayed she'd continue.

Sure enough, this time the dark haired vixen kept up her ministrations. Jacking him till his climax subsided. Afterwards, she captured the stray dollops of cum and deposited them in Tracy's mouth and he swallowed submissively, even those his cheeks burned bright red in humiliation.

Poor Tracy didn't have it in him to blush. But the shame of the act burned inside now that he was sated. He'd been jacked off. He'd been fingered. He'd swallowed come. What must Maggie think of him now?

"What do you say.." Maggie looked down expectantly.

"Thank you?" Tracy whispered as Maggie smiled and kissed him again and again.

"That's my good girl. Now you can show me your appreciation now that it's my turn," Maggie said, scooting back on the bed while propping her back with a pile of pillows. She spread her legs wide at the edge of the bed.

It was a position Tracy had come to know quite well. Who wouldn't want a pretty girl spread out so wide and welcoming? However, of late he'd come to resent that comfortable position. For while she was reclining on her soft mattress and pillows, Tracy was required to slip off very same bed and down to his knees on the cold hard floor.

Down between her thick outstretched thighs. The scent of her musk so strong, almost an assault on his olfactory senses. Her petals, what once seemed a pretty perfect flower, now seemed a hungry mouth. She was already soaked. He blew his warm breath over her sex and began to lightly kiss her. She let him for awhile, purring while he went down on her, running her fingers through his hair.

I'm glad you liked it," Maggie said. "It's always fun doing different stuff. Just be sure to remember it when it's my turn for something new."

Tracy shivered, wondering what this perverted girl had in mind. ********************

There were other later times, times when Tracy felt that he was being taken advantage of. Times when he felt the bitter sting of betrayal.

"Drink your smoothie missy," Maggie said. "Or it's time for a little correction."

"No!" Tracy stomped his foot. He wouldn't drink and he wouldn't stand for it "Not until you tell me what's in it."

"Fine," Maggie said. "We'll double it."

"Triple," Tracy raged. "It doesn't matter. I won't do it. Not until you tell me what's in it."

"Fine," Maggie said, her mind running full speed, backing down just this once, but knowing she couldn't let her charge get too full of himself. "Fruit. Yogurt and a few other ingredients."

"How do you explain this!" Tracy pulled up on his sweater and the cups of his padded bra.

"I don't understand what I'm supposed to be looking at."

Tracy looked down. There was nothing there. Wait, he was still trying to figure these things out. He took off the sweater and top and put his arms down and framed his chest with his hands.

"What am I supposed to be looking at?" Maggie said.

"My nipples," Tracy's face burned a bright red. He had been noticing the swelling for some time now. At first he figured it was due to Maggie's tormenting his nipples. So he'd tried to be extra nice. It was then he realized the swelling didn't go down.

Maggie smiled and her cheeks flushed. "Let me take a look."

She drew close for inspection. She thumbed his tight nipples, relishing how they grew hard. "They are very cute little nipples."

"They are swelling," Tracy said, circling the puffy area with his fingers. "See...that's not normal."

Maggie smiled and took off her shirt and bra. "Look at chest baby," She showed of her heavy breasts. "They are much larger than yours."

"But I'm not.." and though he was extremely angry, Tracy stopped short. There were some things he never said to Maggie, no matter how angry. "I don't have breasts."

"You mean you didn't," Maggie said. "And what would have happened if someone saw your chest? They would know your secret, which is my secret too. So we can't have that, now can we? Besides, you can't wear a bra all the time. What if we go to a beach?"

"But - but," Tracy didn't want breasts. This was just an act so he could go to college and keep out of trouble. But these...there were real and they felt permanent.

"Shhhh....don't they feel nice," Maggie ran her fingers over those tender buds and suckled one for good measure.

"But this is my - my body," Poor Tracy felt his knees go weak. Yes, it did feel nice, but this was his body. His. And this didn't just happen, it had to have been done. The only way he could think of was in those daily smoothies Maggie was intent that he drink.

"You should thank me," Maggie said. "Do you know I had to get a prescription for the pill and then send it off to 4 online pharmacies in order to help you? To make sure that you aren't caught. This isn't just about breasts, how long has it been since you've had to shave that wispy little mustache of yours?"

Several weeks. Oh God, would he be able to grow a mustache again even if he wanted to? He'd noticed other changes. He skin was smoother. His body softer. It was easier to keep his voice at the proper pitch. Yes, these things made it easier to pose as a college coed, but how permanent were these changes. Mmmm- but Dear Lord her hands felt good and his nipples were so sensitive.

"I'm waiting..." Maggie said, pushing him down on the bed, and rolling his panties down his legs. She tugged off the tape that held his manhood hidden between his legs. She licked his cock. She even put the head in her lips. She'd licked it before, but never put it inside her mouth. Never sucked him. Was this what it felt like to make love as a boy? To get a blowjob?

"I'm still waiting..." Maggie said.

"Thank you love." Tracy moaned as Maggie took his cock into her mouth and sucked again. Ahhh heaven. He wished he were harder, however, she didn't seem to mind.

"There is more where that came from, but first drink up," Maggie said and went down on him again.

Tracy picked it up from nightstand. He wanted her to continue. Wanted her to suck him. What was one more? He swallowed it down as Maggie worked two fingers into his asshole.

"Mmmmphhh..." Tracy moaned. "I'm coming. Ah ah- here it comes."

He'd never felt such pleasure. He came right then and there. It felt a little funny. He wasn't quite hard, but he came nonetheless. Came right into her mouth. Ahhh - it was heaven alright.

Maggie got up from the floor and kissed him and it was a bit of a surprise when she returned his sperm to him, but by now he was used to the taste and swallowed it without complaint.

"Now let me see those nipples Missy," Maggie said. "I believe you still owe me for that outburst."

"Please..." Tracy begged. He'd been so certain before. Now his certainty had vanished. Tears welled in his eyes, his boy already knowing what was in store.

"You should have thought of that earlier," Maggie said. "Don't make it worse than it already is."

Tracy looked down at his chest, he couldn't help but regret that he'd given in on drinking the smoothie. He had breasts. He'd assumed the swelling of his nipples was caused by the punishments. Now he knew the truth. Yet knowing what he knew, he had the feeling that after the punishment he was going to get, he'd be reluctant to rebel again.

He was still a boy though, he was sure of it. He had his first blowjob. Yes, and boys received blowjobs. He only had to endure and then he'd be free and no more smoothies. But until then, he wanted more blowjobs.

***************************

In the coming weeks, Tracy felt like he was less and less what made Tracy Tracy. While he was more and more what made him into whatever it was Maggie wanted.

At one time he had to make a supreme conscious effort to keep up with Maggie's many demands. To sway his hips when he walked. To cross his legs, wrapping them around each other when he sat.

He couldn't help but think of the many stares he received on a daily basis. Worse, at the mixers, boys were no longer coming on to Maggie, they were coming on to him.

He was a boy. He repeated the fact to himself every hour. But though he repeated it, he didn't feel much like a boy. He had a girlfriend, but the truth was...

A boy wouldn't be wearing garters, stockings, heels, and a bustier. A boy wouldn't be on all fours. A boy wouldn't ...ouch...

Tracy tried to wriggle away from Maggie's strong grip. However she had him on his hands and knees. One of her hands firmly held him by the pony tail, they other reached around his waist, going for his crotch.

"See, it isn't so easy," Maggie said. "I thought you said you wouldn't get put in this position."

"You tricked me," Tracy grunted. He most certainly would never let a boy get him like this. On all fours. Naked except for a pair of heels.

Maggie's cheeks were rosy from the power the rushed through her loins. "What are you going to do now? You know you can't call for help. Do you give up? " She pushed her hips forward.

"Yes," Tracy gasped. She had him.

"Now let go of my wrist and I'll tell you how to handle this situation."

Tracy reluctantly let her go, even though it left him even more in her power.

"Now boys have a one track mind," Maggie said. "All that testosterone leaves them almost brain damaged. So instead of leaving it up to him, give him some suggestions of things to do to keep his hands busy elsewhere other than where your secret will be discovered."

"Where?" Tracy asked.

"I don't know. Think of something. At the very least you could ask him to spank you. No one can resist giving a sexy girl a little spanking."

Tracy tried to think, tried to come up with another use for her hands, but drew a blank.

"Spank me." He stammered.

Maggie smiled. Her hand came down once and then again. Leaving a red hand mark in their wake. Then she paused.

"You can't just sit there like a lump," Maggie said. "Otherwise he's going to get bored and go back to what he was doing. Now try again. And encourage me this time."

Tracy tried to think of another course of action, but still couldn't. The stinging of his bottom made thinking that much harder.

"Spank me," he breathed.

Maggie obliged with two more hard licks. This time harder than before.

Damn it smarted. Worse, Maggie had stopped once again.

"More." Tracy encouraged and received two more blows. God, was her hand made of iron? Worse, the smacks against his flesh were loud. He prayed no one could hear what they were up to.

"Mmmmm...you are turning me on," Tracy managed to force out.

"Good," Maggie encouraged, her voice low from her arousal. "Now you got his hands occupied, but a boy has other things for you to worry about."

Maggie pushed her hips forward. Her old dildo was long gone. Now she sported a strap-on for these training sessions. She ran the shaft up and down her lover's makeshift slit.

"Let me turn around." Tracy said. "I want to suck you love."

"No boy is going to turn down that sweet pussy for a suck job," Maggie said. "Your chance for that ended when you got into this position. Just tell him you are a virgin and are saving yourself for marriage."

"I'm a virgin," Tracy stammered. "I'm saving myself for marriage." Was it really so easy? Why had he struggled with her for so long if this was all he had to do.

Unfortunately, there on his hands and knees, with Maggie there behind him, he had no way to see that she was lubing her strap on cock. No way to know she'd tightened her grip on his hair and held him firmly by the hip. Didn't see her line up the head with his tight crater.

If he did, he'd surely have struggled. He'd at least tightened his rear.

"Uffffff..." Tracy grunted. Dear God, she'd impaled him. She'd stuck it up his rear.

Maggie eyes blazed like lasers. She bit her lip and kept pushing. Kept working that big cock in her lover's tight ass.

"Oh God...Oh God..." Tracy groaned. It was like an immovable object invading his bowels. He tried to fight the invader, but God, it hurt so much.

"I can't," Tracy gasped. "It hurts. It's too big. Please."

"Sush," Maggie crooned. "I won't hurt you baby. I'll be ever so gentle."

She began to slowly withdraw it.

"Does that hurt?" she asked.

"No..." It was hard to talk. When she pulled it out, it seemed to leave a void that took his breath away.

"See..."Maggie slowly reversed coarse, pushing it in again, but only an inch or so, before withdrawing again. She slowly worked him with it. Gaining ground each time. If only a millimeter or so. It didn't matter. She had all night.

God, there was no doubt about it. This was heaven, Maggie assured herself. To think she thought she was cheated when her roommate turned out to be a boy. No, she wasn't cheated. This was a gift. A gift from heaven above.

It wasn't heaven for Tracy. His knees hurt. His hair hurt. His bottom ached.

"If you just squat there like a bump on a log," Maggie said. "He's going to grow impatient. He may get rough."

Maggie's strokes grow longer. Stronger.

Poor Tracy couldn't take a pounding. He thought back to the times he'd pleasured Maggie. What had she done? He gave a gasp. A moan. "Yes..oh yes..," he panted. He arched his back. He moved his body back and forth. Meeting her thrusts with his own.

"I'm getting close baby," he cried breathlessly in a way that anyone would assume he was getting ready to climax, praying it would be enough for Maggie not to try getting rough with him, it felt like he was being turned inside out as it was.

Maggie moaned in response. She's known Tracy would enjoy it...once he had the proper encouragement. She rubbed the bridge of her sex on the pad from Mr. Friendly to speed her along.

But for Tracy, Mr. Friendly wasn't quite so friendly. Mr. Friendly was uncomfortable at best and downright hurt at worst.

Tracy bit his lip, his brow knitting in concentration. Boys were tough. He was a boy. A boy in hiding. God, but it penetrated him. Opened him in a way he didn't think was possible. Worse, the more he tried to fight it, to clench, to resist the invader, the more it hurt.

It grew too much for him to take. His will sapped, he stopped fighting the battle, going down on his elbows as Maggie continued to work him with the phallus. He still managed to meet her thrusts, her body slapping into his own. Then a disturbing thing happened. He discovered, that angled down as he was, when it hit him inside just so, a burst of pleasure could be felt. He could feel himself leaking, though he wasn't coming in the usual sense.

"Oh God..nggg..ugghh.." Tracy moaned helplessly. What was happening to him? He was definitely leaking. He tried to stop, to tighten his muscles, but that only served to cause him more discomfort as his sphincter tightened too.

"Fuck..baby...that is one sweet ass," Maggie moaned. Casually giving his bottom a spank and a harsh grab of his cheeks.

"God you are a dirty slut. You love it up the ass. Look at the way you squirm. The way you beg for it." Maggie panted, fuck she was nearly there. She reached around, and made an astonishing discovery.

"You are wet baby," Maggie said. "I can feel it running down your thighs. You like it don't you. You like it up that tight little ass."

Maggie's passions rose, sending lightning through her loins. Grabbing Tracy by the hips, working him, rubbing her clit up and down the pad of the strap on. "Oh take it, take it you sweet bitch take it."

"Oh God..more - more -" Tracy moaned, God he'd come close to orgasm with no stimulation on his cock at all. And though she gave it to him, and though each plunge brought a small burst of pleasure that resembled coming, it wasn't quite the same. He never road over the edge. Just those small maddening bursts over and over again. Making him squirt just a little each time.

"I love you baby," Maggie collapsed after her orgasm, holding him tight, cuddling him and running her fingers through his hair.

"I love you too,"Tracy did. His heart felt full whenever he heard those words, but now that his endorphins began to ebb, his ass hurt. It really hurt. Would he be able to walk tomorrow?

He knew she was trying her best to help. That this was all in order to help him in case he was involved in some worst case scenario. But there'd never be a worst case scenario, he'd make sure of it. He'd never be around some boy. What's more, he knew a way to make certain of it, and to make certain Maggie needn't worry about any more of these bizarre sexual training sessions.

"That was nice love," Tracy said.

"Anything for you baby," Maggie mumbled, her eyes only half open.

"I've been thinking," Tracy said. "Though no one can find out what I really am...there are other girls on campus that don't date boys. "

"Sweety, those girls are dykes," Maggie said, patting Tracy on the head in pity. Oh this was perfect. It was just what she wanted, but hadn't figured a way to get Tracy to come around to the idea. The fact that he volunteered it made it all the sweeter.

"Yes," Tracy's cheeks were no longer warm. They felt hot. "But we could. You and me. We could tell people that we are lovers. There's nothing wrong with it....and we do love each other...right?"

"Baby of course I love you," Maggie said. "But if you start looking butch, then people are going to suspect."

"I know.." Tracy's voice lowered to a whisper. "but I..I don't have to be butch."