The Scholarship

"Show it to me." Maggie said. She'd wasted her time pursuing, almost falling for, someone who wasn't a girl. Wasn't what she'd wanted after all this time.

Tracy blushed. He couldn't. He'd wanted nothing more a few minutes ago. But not now. Not like this.

"I"m sure, you will be very popular in jail dressed like that." Maggie said.

Tracy's eyes widened in alarm. Jail? For what?

Maggie answered the question that he never asked. "For pretending to be a girl so you could take advantage of me. And you have taken advantage of me. You've watched me undress all these nights. God, seeing everything I have without my consent. Well, I got news for you , now it's my turn."

Tracy stood. He blushed furiously. He thought quickly, but he couldn't see a way out of his predicament. With trembling hands, he took off his shirt.

"So the bra is stuffed I take it?" Maggie said. Watching Tracy, she could feel her initial anger dissipate. She tried to hold onto it. She wanted to rage. She wanted to punish this little shit who had fooled her. But there was something about him. For one, he was attractive. For another , h was so...obedient. Wrapped around her finger. Seeing him there trembling in a bra and sweats it was hard to believe he was really a boy.

Tracy blushed. "Yes," he admitted.

"Leave it on, but take off those yoga pants."

The blush in Tracy's cheeks went down to his chest. He removed his pants.

"Is it really that small?" Maggie said. To another girl it would have been a put down, but to Maggie it was a compliment. Tracy still looked like a girl to her. He still made her hot. "It's barely a bulge."

Each comment seemed a blow to Tracy's pride. He was terrified. He almost liked, but thought the better of it. For there was more than met the eye.

"I have two pair of panties on." Tracy said. "A regular pair and a special part that ... keeps it hidden."

"Oh I see the lines now. Let me see them."

Tracy took off the ordinary cotton panties, leaving him only in a flesh colored tight thong, specially made to control his bulge.

"Even like this, I still can't believe you are a boy," Maggie said. The girl rummaged through her drawer and tossed him several items. Several small and sheer items.

"Put them on. Now."

Tracy looked through them. What was going on? "I don't understand..."

"There are two ways this can go Tracy," Maggie said. "Speaking of which, is that even your real name or another lie?"

"It's my name.." Tracy answered.

"Good," Maggie said. "We may be able to go from here. Now that I know your secret, I have a choice to make. I have to turn you in...or become your accomplice since you've dragged me into this. So if I'm going to be an accomplice, I need to make sure you won't get caught. Now put them on, or do you want me to turn you over to Gwen. You know she's a criminal justice major, don't you? That should be rich."

"I-I don't want you to turn me in. I just...Tracy wanted to obey, but he was out of his depth in some ways.

"I don't know how all this works." Tracy said, holding up what happened to be a garter belt helplessly.

"You have so much to learn, I don't know if I should even bother," Maggie sighed. "Okay, here let me help. But just this once."

Poor Tracy only had experience with the minimum of girls clothes. He'd never worn stockings that required garters. He'd worn some heels, but nothing like these. How could someone be expected to stand in them, much less have to walk.

"Now let's try kissing again. It's more important now than ever. Before, you were just an inexperienced girl who had all the time in the world to discover this stuff, but now you better learn it quickly or risk being found out," Maggie said, moving close, her mouth slightly open and tongue extended. "Just like we did before, hold your arms up and keep your hands out of the way."

Tracy knew what to do this time. He'd already played this game once before. He played it coy, waiting for her to brush her lips against his.

"We've already done that. This time I want you to kiss me back." Maggie said. "Now kiss me. Suck my tongue. Do it pervert."

The dark haired girl parted her lips and stuck out her tongue. Poor Tracy preferred the other way, this way seemed so - embarrassing. Worse, caught up in this position, instigating the kiss with his arms held over his head, he couldn't help but feel weakened somehow.

Worse, she didn't seem inclined to kiss him. Instinctively, he knew he had to kiss her to pass this test. He tried the things she had tried with him. Light coaxing kisses, dotting Maggie's chin, her ear, even on her unresponsive lips.

Eventually her lips parted. He kissed her passionately. He could feel her respond. Could feel her tongue extend. Tracy did as she bid. Sucking on her tongue. Sucking it into his mouth. He felt a bit of extra wetness in his mouth. Was it Maggie's saliva? He wasn't sure, but he felt that tingly feeling return once more. The warm feeling made his embarrassment a bit more bearable.

"Not bad," Maggie said, licking her lips, then moving close once more. She was hot. No she was more than hot. She was steaming. She had fantasies she was ashamed of. Fantasies that would scare the innocent girl she thought she was pursuing. But fantasies a boy - a perverted boy in hiding - fantasies that could be explored. "Again."

Instead of just letting Tracy suck her tongue, she kissed him passionately. Exploring his mouth with her tongue, nibbling his ear, sucking on his neck.

Tracy felt Maggie's hand slip under his shirt. Up under his bra. Teasing his nipple. He moaned in response. But then her touch grew hard, catching his nipple between forefinger and thumb and giving a cruel twist, and the sucking on his neck grew more forceful, in danger of giving him a hickey and a painful bite.

"Ouch," Tracy admitted, his lean body squirming in Maggie's firm grip arms coming down and attempting to force the girl away.

"That's a nice touch," Maggie said in a low voice. Dominance and submission - this was her fantasy. Boys always tried to be boys, but she wanted someone soft - someone yielding. She'd have it one way or the other. "Boys are tough...a little fake whining will surely make them think you are a girl. Now get those arms back up. I won't tell you again."

"Yes.." Poor Tracy could feel her cold blue eyes boring into him, raising his arms back up over his head. They felt weak and tingly. Worse, she'd taken his cries for fakery, but the truth was, it had hurt. He felt unmanned by that admission, because as Maggie said, "Boys were tough."

Maggie kissed him again. Kissed him however she willed. Her hands roaming over his body. Palming his ass. Her fingers twisting and pulling his tender nipples. He held his breath, tears welling in his bright eyes, not feeling like a boy at all, until finally he was forced to admit his weakness.

"Ouch..that really hurts." He gave a great gasp when she finally released him.

"You are learning quickly. Most boys don't know it, but girls have sensitive nipples. Yes, this may work after all," Maggie said, her nostrils flaring. "It may indeed."

His nipple still smarting, Tracy was so very relieved when she took him by the hand and led him to bed.

"Now it's time for you to learn something else every girl learns at some point in her life" Maggie breathed, taking off her nightshirt.

God she was incredible. Standing there nude and unselfconsciously, she was soft and round and all that he had imagined. She made a mound of pillows on her bed, and sat down, reclining against them. Her legs were spread wide. Her pussy was dark and matted. Not like the girl's from the porn he'd seen, but she still looked attractive to him. His cock ached as it fought against the confines of his shaper.

"Come to the foot of the bed," Maggie said, beckoning him with a crooked finger. You've got me all hot and bothered Tracy. If you are going to pretend to be a girl, you have to learn what happens when a girl has to do what a girl has to do."

"I don't understand," Tracy stammered, face flushed. He thought he did, but he wasn't sure. My God, was it possible. Was he going to..have sex?

"Don't be a stupid," Maggie said. "You can't just tease someone up and leave them hanging. You know what to do. Use your mouth on me. Like I said, you've got me hot. Now take care of it."

"But I've never," Tracy breathed.

"Sush..just do what I say," Maggie said. "Blow on it first. Make your breath nice and warm. Mmmmmmm....now use your lips. Just the tenderest of kisses. Oh Tracy...that's nice. Do you like it? Do you like making love to my pussy?'

Maggie's fingers ran lovingly through his hair. Her soft moans were music to his ear. Her aroma was thick and musky. It smelled more than he had reckoned. The lips were pink and moist. Like a pink flower. It would be perfect except for the tight pair of shaping panties keeping his manhood tucked and safely out of commission.

"When I ask a question, I expect an answer," Maggie said, giving his ear a sharp twist for emphasis. It came out as an order. So uncharacteristic of the girl he'd come to have such strong feelings for. Or his best friend for that matter. Perhaps she was still upset about his lies. Though certainly she'd come to realize he was just as unwilling as she.

"Yes - I like it." Tracy said after remembering what the question was.

"Am I just a piece of ass to you?" Maggie's tone grew hard. "Am I you little pervert?"

"No." Ouch. Again she twisted his ear. Tracy began to feel a tremble of nervousness.

"When I ask a question, don't just answer yes or no like I'm some kind of piece of ass you can lie to to get into bed" Maggie said. "I want a little endearment. A yes love or no love would be nice, considering all I'm risking helping you carry on this charade. Do I make myself clear?"

If Tracy was unsure of what he'd gotten himself into before, he was nearly terrified now. However, there was little he could do given he already precarious position. Little he could do but utter a soft and submissive, "Yes love." It was a phrase he'd come to know quite well.

"Oh yeah baby that sounds nice," Maggie moaned breathlessly, pulling his face in tight. "Oh fuck yeah. Say that one more time."

"Ouch..yes..love..," Tracy moaned. It was actually growing a bit uncomfortable. She pulled his hair and he discovered her thick thighs were incredibly strong. It was a little scary.

"Mmmm- you like that baby? Then get in there. Use that tongue on me. Use your lips-your nose... make love to me. Oh God, I love it. Do you love it baby?" Maggie breathed. "Answer me."

"Mmmphhh-yes love..." Tracy groaned. It was hard to hear. It was hard to breath. His lips ached. His neck hurt. He was a bit scared.

"I like that too. Oh sweetie, you are going to make me cum. You are going to make me cum so hard. For someone so inexperience, you give great head."

Tracy's cheeks colored. He didn't want to give great head. It sounded like something a girl would do, not a boy. Yet, he had no choice but to continue his oral affections.

Maggie hips pumped faster, grabbing Tracy's ears she pulled hard. Working herself on his mouth. Oh yeah. Oh fuck yeah!

"Owww- I mean -mmmm..more gently please love," Tracy gasped.

"Ahhh..fuck I'm coming," Maggie moaned, oblivious to his protestations, a wave a pleasure cascading through her loins. Completely soaking Tracy's cute face with her nectar. "Oh God, I'm coming."

When Maggie's lust was quited, she tugged Tracy up from the foot of the bed. Tracy loved it, loved the tender kisses his lover bestowed on him. Loved the feel of their naked sweaty bodies intertwined together. Love the little I love you's she sighed.

However, he didn't love the swollen ache in his trapped balls or the heels that were still strapped to his feet. He'd love nothing more than a quick session of masturbation and to get those damned heels off his feet, but Maggie was snoring so cutely, and for the life of him, he couldn't wake her up.

It wasn't how he had imagined his first time with a girl. Sticky faced, aching tongue and bruised lips weren't supposed to be his reminders, but then again, he'd never imagined himself with such an incredibly beautiful girl to begin with. A girl that wasn't just attractive, but attractive and funny in a quirky sort of way.

For such a girl, he was willing to compromise. At least a bit. ++++++++++++++++++++++

"Mmmmmmm....I just don't know what to do with you," Maggie purred, as she idly twirled her fingers through a lock of Tracy's blond hair-that was merely blond before but now had spectacular highlights. "On one hand I feel so guilty keeping up this act of yours."

'Not too guilty to get eaten by me,' thought Tracy, as his tired tongue glided up and down Maggie's wet slit for what felt like the thousandth time. It wasn't just his tongue, his lips were bruised and his knees ached from kneeling on the floor so long.

"Oh yeah," Maggie swooned, her large thighs spreading wider from her leisurely pose in her comfortable chair. "Just like that. Just like that. Work that tongue. Faster you little lez. That's the way. Mmmm...I looked it up today, and it is a felony. I'm like guilty of a misdemeanor for just knowing about it. Mmmm..but baby you are my misdeameaner - the more I miss, the meaner I get. Now my clit baby. But gently. You know how I like it."

"Yes love," Tracy said, looking up from between her outstretched thighs, his face drenched in girl juice. He blew on her clit with his warm breath. Warming her up to it. He'd been at this for nearly an hour. At one time, he'd been crazy about the idea of going down on a girl. But now? Now, while it still turned him on, it felt more like work than sex.

He looked over at the clock. Shit, his class would be starting in a few minutes. He needed to finish Maggie off - not only that, he needed to clean up and get out of his horribly humiliating outfit.

Not just any outfit, it was one of the outfits Maggie bought him as a present. A kinky number for him to dress up in when he made love to her. Well..went down on her. One night he was a sexy nurse. Another night a meter maid. This morning he happened to be ... a schoolgirl.

He wore a short pleated skirt that hugged his hips and flared out ending mid thigh. A form fitting sleeveless sweater. A tight fitted oxford. A striped tie. Two purple thigh high socks. A pair of Mary Janes. Underneath he wore a pushup bra and a pair of boy cut panties. A pair of pigtails completed the outfit.

Tracy fluttered his tongue, just the way Maggie liked it. He kept at it despite the pain as she tugged his pigtails and trembled as she moaned. Finally she was sated. He slowly licked her, bringing her down from her orgasm.

Wiping his face, Tracy quickly stood. "Sorry Love, I hate to run, but I have to get ready for class."

"You're already ready baby," Maggie cooed. "Just wash your face and freshen your makeup."

Tracy looked down nervously. She couldn't be serious. He laughed at her joke.

"Very funny Maggie."

"I'm not laughing." Maggie said. "I bought you that outfit. What's the fucking problem. Are you ashamed or something?"

"No love...." Tracy whispered. He was ashamed. Intensely so. Yet he'd offended Maggie somehow. He sought to mediate the damage. "I - I really like them."

Maggie hugged him close, her hands sliding under his miniskirt and cupping his bottom. "Don't worry, if you mess them up, I'll buy more. I have plenty of money. Don't you want to look nice for me?"

"Yes love.." Tracy stammered. He fumbled with his hair. The humiliation bit hard. "Can I...at least.. put it in a pony tail, love?"

"Baby," Maggie smiled, twirling one of Tracy's pigtails with an index finger. "Just think...all day long I will be imagining you back between my thighs and one of your cute little pigtails in each hand. Just imagine how wet I'll be? Isn't that what you want babe?"

"Yes love," Tracy's knees trembled. He could only imagine what others would think about when they saw him. Did they imagine holding those same pigtails? Having no choice in the matter Tracy went to class. He'd never felt more out of place, more vulnerable. It seemed that everyone was staring at him. Most girls looked at him in disgust and a bit of jealously. Boys looked at him with unrestrained lust. It was the last thing he wanted.. all those boys staring at him, practically undressing him with their eyes. It was the clothes, they practically begged for stares. A skirt that constantly needed to be pulled down, a shirt so tight it was difficult to move, thigh high socks attracting attention to his legs, a padded bra attracting eyes high on his chest, worse, there were fresh hickies on his neck that advertised just what sort of girl he was. Those damned pigtail tickled his neck every time he turned his head, always reminding him of his embarrassment.

It was too much and so very humiliating.

I'm a boy-I'm a boy, he repeated over and over again trying to make the situation more bearable. This is only for a little while. This is only for a little while. He kept his head down and tried his best to ignore the looks. To get through the day without incident. =================

"I creamed my panties when I saw you. You looked so cute, I wanted to eat you up." Maggie said as she grabbed Tracy by his pigtails and pulled him in tightly between her thighs. "I've been craving you all day. But I was slightly disappointed the way you walked, head pointing down at your feet like you were trying to hide. Then I saw your collar all popped up, and you know how I feel about popped collars. They are extremely tacky."

"I'm sorry," Tracy said. "But I had a blemish on my neck." But it wasn't a blemish, his neck was adorned by two hickies and one had a set of teeth imprinted on it.

"Next time, just spruce it up with a bit of makeup."

"I tried," Tracy said. "The makeup rubs off my neck and people can see..."

"Your hickies."

"Yes." Tracy's face flushed red as he felt the stares he'd received today anew.

"What are you so worried about," Maggie said. "It's not as if you are in high school anymore. You are expected to have a bit of fun in college."

That was the most embarrassing aspect of it. He'd seen a few hickies in high school, but not in college. Worse, he'd heard some of the comments from other girls. Saying she'd not learned anything in high school. In the end, she'd flipped up her collar to hide the evidence of the morning makeout session with Maggie.

"And no more popped collars," Maggie said. "I find them distasteful."

"Yes love," Tracy said as he returned to the task at hand and planting a few light kisses on the full mouth of Maggies wet and swollen sex.

"Look. I've got a surprise for you," Maggie smiled. From behind her back she brought out a latex dildo she'd kept hidden.

"What is that for?" Tracy said, a trace of panic was in his voice.

"We are going to have to teach you your way around one of these," Maggie said. "I mean, come on, how long do you think you can pull this off without knowing certain things. I found out in no time. So what will you do if some boy gets too fresh with you on a date? Call the police? We both know that isn't an option. So we have to teach you another way. "

"But I'm not dating..." Tracy stammered. He wasn't dating any boys. He had no intention of dating any boys. He wasn't into that.

"Sushhhh," Maggie placed the dildo between her thighs. Wedged into the groove of her bare sex. "Where are you going to go? Are you going to call for help? Go ahead. What if the police get involved? You know what will happen then. So stop pretending you are so rough and tough. We both know what you will do when it comes down to it. So you might as well learn to do what it takes to not get caught."

"But I won't be alone with boys." Tracy blushed deeper and shook his head, never moving from the spot where he knelt between her thighs. "I'm careful."