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Chapter 14
by
Nicegent42
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Chapter 14
Jake pulled the Mustang into a space near the front, the headlights sweeping across the stone façade of the museum before cutting out. The faint beat of music slipped through the glass doors even from here, a muffled thrum that seemed to pulse in Tim’s chest. He had spent the entire ride gripping his little red purse like a lifeline, counting down every second until they arrived. Before the engine had even been turned off, the very moment the gearshift hit park, he couldn’t stay inside a second longer.
Shoving the door open and stepping out quickly, the disguised college freshman found himself almost losing his balance. A night and afternoon practicing in high heels hadn’t exactly made him a master in balancing in them and with the rapid movement and the slick surface of the lot he was close to taking a tumble. Stomach lurching, ankle bent, Tim slapped his hand against the roof of the car to steady himself. The sudden stumble yanked his eyes downward, to the hem of the short dress brushing against his thighs, to the dark nylon stretched over his legs, to the way the glossy heels pinched his toes together and **** his calves taut. For an instant he saw himself exactly the way anyone else would, a girl scrambling in her date’s car door, nearly toppling because she was too eager to get out. His mouth went dry.
Seeing Tammy practically jump out of his car, in a hurry to get the date started now that she saw where they were, brought his normal smirk into something much wider. They had already talked about where things were going and the fact she slapped the roof of his car as she got out to make him move faster only encouraged him more. “Yes ma’am.” he said to himself, turning off the car and getting out.
Walking around his vehicle with an **** swagger in his stride Jake took his date’s hand in his own. Walking around holding a girl’s hand wasn’t exactly his preferred way to spend his time, but he knew girls loved the little touches like that and that always led to what he actually wanted. “I thought you might like to look at some art, you seem like the type of girl that is more cultured than a brute like me.” Jake laughed, the destination picked long before he had ever met the girl, it bringing success to his dating life more than once in the past.
Tim’s fingers disappeared inside Jake’s. The difference was startling, Jake’s palm more than a little broader than his own, his grip firm enough to guide without asking. Tim’s own hand felt dainty by comparison, the way it had to look, his hand… a girl’s hand snugly inside her date’s’. The click of his borrowed heels against the asphalt sounded painfully loud with each step, echoing between the parked cars, and every sharp tap reminded him he was not walking like a man. ‘It is just a hand… it is just a hand, no big deal, just one foot in front of the other.’ Tim thought, wanting to pull away, shove his hands in his pockets, though there weren't any, just a purse that held things he really didn’t want to think about. None of that was an option, not really far as he was concerned. ‘Tammy would like this, right? Yeah, I would want to do this if I was with…’ Tim’s mind trailed off, he had never been on a date in his life till now so his thoughts of what he would want to do with a girl didn’t matter. ‘Tammy, like this and I’m Tammy, just be Tammy… easy, super easy, soooo easy… Fuck.’
Ahead, the museum glowed under floodlights, its wide glass entrance spilling warm light across the sidewalk. A cluster of people stood outside laughing, their voices lifting over the faint strains of jazz from inside. Tim’s stomach tightened at the sight of them. ‘What if one of them looks too closely? What if someone recognized me?’
Despite the burst of panic, Tim, as Tammy continued on, unable to do anything else when hand in hand with the taller boy.
Inside the foyer the light was soft and golden, banners for A Night of Art and Wine hanging above the desk where a woman waited with a roll of tickets. Jake let his grip loosen to free his hand from Tammy’s and pulled out his wallet to cover both admissions.
Tim hadn’t even considered paying, considered money at all. Jake had paid before he even had time to think about paying his own way, he wasn’t even sure there was money in the purse, Tim wasn’t even sure if anything from his own wallet when the girls had strong armed him was in the bag. The simple act made him wince. ‘He might as well have stamped his ownership across me…’
Swallowing hard and lowering his eyes, trying to make himself small, trying to let Tammy take over. ‘Tammy is supposed to be shy, Tammy is supposed to be quiet, Tammy is supposed to smile, she likes Jake… her date. My date…’ It was the only way to survive, so when they stepped past the desk and into the open lobby, Tim **** himself to do something that twisted his stomach into knots. He slipped his hand back into Jake’s on his own. Not because he wanted to. Not because it felt right, but because Tammy would, Tammy would enjoy it.
Moving together through the open lobby, the faint jazz swelling louder with every step until it filled the air, the kind of music that made everything feel more sophisticated than it really was. Jake thought of it as elevator music, not caring for it, but the first time he had taken a girl here she had said how she loved it, how soothing it was. He wasn’t exactly the biggest into music, he liked what he liked, but was willing to endure or ignore others if a pretty little thing liked it. Inside past the banners and the ticket desk, the wide entrance opened into the first gallery, where tall round tables stood scattered between sculptures and canvases hung along the walls. The crowd was thin enough that each cluster of people had space to breathe, for him to work his charms on Tammy, and other girls before her.
For Tim the band that played added background sound, a slight cover for the two of them, giving him something else to focus on and lively enough that the museum felt alive in a way he had never experienced before.
Jake steered them without hesitation to one of the high-tops near the front. From here, the band was clearly visible, the polished brass of a saxophone catching the lights, while just beyond them a collection of abstract paintings splashed wild color across a white wall. Tim didn’t know what any of the art meant, but he also didn’t put much thought into it, having more than enough on his mind. He kept his head bowed slightly, purse hugged to his side, heels clicking against the marble floor as he slid onto the tall stool next to Jake as the brown haired young man held the seat out..
“Let’s get this started right,” Jake said, signaling to a server with a raised hand. “When you can, and no rush, bottle of the house red.”
Tim’s stomach tightened. Wine. Drinking. He hadn’t even thought about it. His mouth opened before he whispered to Jake. “I… I’m not twenty-one. I can’t drink.”
The words tumbled out, his pulse hammering the whole time. In his mind’s eye he saw flashes of the fraternity house, of parties he had imagined when he pledged, of red Solo cups sloshing beer, of someone lifting him up onto a keg for a keg stand, while everyone cheered. That was what drinking was supposed to look like. Loud. Masculine. Fraternity-born. Not wearing a little red dress, sitting on a date with a boy, a bottle of wine coming his way and an ID in his purse that said he was Timothy Thompson, not Tammy. Not that he was even sure his own ID was in the bag.
Jake leaned a little closer to his date, his easy smile, that smirk ever present. “Don’t worry about that, babe. Nobody here’s checking. They see a pretty girl with a guy like me, they don’t ask questions.” His voice dropped just enough to sound smooth, or at least that was his intention. “Besides, you carry yourself like a woman who belongs here, belongs with me and I’m truly happy to be here with you tonight Tammy. You don’t have to worry about a thing, they’d never think to card you. ”
Heat crawled up Tim’s neck at the compliment, his mind spinning. ‘Jake, he is a paragon at the frat… he is THE man and he is happy to be here with me?’ He wanted to snap back that he wasn’t a girl at all, not someone he would actually want to hang out with, hardly anyone ever really did, but a small part of him enjoyed the idea of it, despite the lie, despite that he wasn’t suited for anything here. ‘Tammy is though… maybe? She would like this, Tammy would like this, I like this, I like this…’
As Tammy, Tim smiled, sat there and nodded. “Thanks, I…, this place place is nice. Thank you for taking me here.”
Brushing her blonde hair slightly to the side, Jake kissed Tammy’s cheek before clasping her closest hand between both of his own. “This is just the start. If I have it my way we are going to go to many places together. Have adventures, fun and so much more.”
The server returned with the bottle and two glasses. Letting go of his Tammy, Jake poured with exaggerated care, filling hers first before his own.
The glass trembled slightly in Tim’s hand, an odd feeling in him that he couldn’t describe ran through his mind from Jake’s words. The deep red liquid in the glass catching the lights above. Without a thought he brought it up to his lips, feeling like he really could use a drink, needing the drink to calm the storm inside of him.
The wine rolled across Tim’s tongue heavier than he expected, smooth at first with a faint sweetness, then turning dry and biting at the edges. It coated his mouth in a way that beer never had, at least from his limited experience. Leaving a tannic film that clung to his teeth and throat. Each swallow sent a gentle burn downward, not like the fiery punch of the shots of Fireball he had on his first night at the frat, but a spreading warmth that bloomed through his chest. The aftertaste of the drink was something more rich and strange, almost overwhelming, yet carrying a heat that made his nerves slacken in spite of themselves.
Jake watched, eyebrows lifting, amusement flashing in his eyes. “Damn, Tammy,” he chuckled, lifting his own glass, taking a sip. “Didn’t think you’d be the one trying to drink me under the table.”
“Ahh…” Tim opened his mouth, making the sound before closing it and starting again. “You know us girls… we like wine.” Somewhere in his mind he just knew girls liked wine more than beer, he wasn’t sure if it was just something from movies and tv shows or if it was a real thing, but felt he had to be closer to the truth when he wasn’t corrected.
“True, and I can tell you are the type of girl who likes to party and I for one like that.” Jake said, filling his date's glass up once more.
It wasn’t long before the server returned, balancing a tray of charcuterie, little wooden boards lined with slices of cheese, curls of lunch meat, and bunches of grapes. The sight hit Tim the moment the board was tilted his way, sharp cheddar and salty ham making his stomach tighten. His body betrayed him with a low growl, loud enough that Jake’s eyebrows lifted in amusement.
“You want one?” Jake asked, nodding toward the food. They were more expensive than he liked for how little food, but considering what she was planning on doing with him, it was a small cost to keep her happy.
Tim’s throat tightened as his mouth salivated at the offered food. He wanted nothing more than to say yes, to grab the board and fill the empty ache gnawing at his stomach. He hadn’t eaten enough earlier, not even close, and the wine was only making the hunger worse. But he could already picture the mess of it. Worse, he could imagine greasy fingers, crumbs, anything that would break the illusion of Tammy being neat and pretty. ‘I’m supposed to be pretty… Jake said I was pretty.’ Tim thought, his own misplaced ideas of girls leading him down a path away from what he actually wanted to do, to say. Lips pressed together, and Tiim shook his head quickly, enough for his styled hair to bounce about. “No, thank you. I’m fine.”
Jake leaned back in his chair, smirk softening into something closer to indulgence. He had heard her stomach, knowing she was hungry, but the refusal made sense to him in another way that was far too common for girls in his opinion. ‘Another girl on a diet.’ he thought with faint amusement. They were all the same, always watching their figure. ‘A whole board of food like that? I would scarf that shit down it down… if I ever ordered one just for myself.’ He never had, or imagined he would ever do such a thing for himself. The art that he didn’t really care for, music he couldn’t care less about, adding some wine and pretending to care about it all. That was for them, to put his best foot forward with a girl. He wouldn’t really lie, he would tell them he didn’t get it, but he also wouldn’t say he didn’t like it either, no the focus was always on them. Girls really were the fairer sex, so pretty and desirable. On his own… Real food was a burger and fries, while he watched a game. Not meat and cheese on a slab of wood. He let the thought pass with a shrug, he couldn’t help a private smirk at the idea of ever going out with a girl who actually ate. ‘Course I wouldn’t want to go out with a fatty…’ Jake mentally added to the idea of a girl actually eating her fill.
“Nothing for us tonight, just going to enjoy the company of someone I don’t deserve and hope she doesn’t wisen up to the fact that she is too beautiful for me.” Jake half laughed as the server moved on to try and push the offered food to another visitor. Turning back to Tammy he poured a little more in her glass, topping it off as he saw it was half gone already.
‘I am not!’ Tim thought as the older boy spoke to the employee, one he hadn’t even glanced at to have even the slightest idea of what they looked like. Being talked about in such a manner wasn’t the easiest thing for him. It wasn’t just the fact of being referred to as a girl or pretty, but also that he just wasn’t used to getting compliments and hating himself a bit for liking the fact he was getting them. With another large swallow of wine going down his throat he accepted the refill without hesitation, lifting it back to his mouth. Tim could feel the slight shake, the tremble in his hand and placed it flat on the table after another long pull of the drink. He had no awareness of the fact no one else in the room was doing more than just taking a few sips of the drink.
Moving his hand once more, Jake brushed his fingers lightly along Tammy’s arm, trying for his touch to be casual but clearly deliberate. “I have said this before, but you look good tonight. It isn’t just about how you look, but all the effort that was put in, I appreciate it and you for it.” he said, letting the compliment roll easily from his tongue. A girl had shown up for a blind date in sweat pants and a hoodie before on him, not even bothering to put any makeup on, that had been upsetting, he deserved more and the worse part was, she was hella cute and if she just had tried she could have been a knock out. Tammy on the other hand, she knew how to present herself and he was loving it.
Tim tiled his head from left to right, the smile on his face wasn’t the largest but it was real as he laughed lightly. It wasn’t funny specifically, but the situation of it all and how much real effort went into him looking this way was absurd. “You have no idea how much had to be done.”
Moving his hand up across her forearm and up to her shoulder, Jake gave her a light squeeze of his hand as his finger tips played slightly with the strap of her dress. “I don’t, not really, but that only makes me appreciate it more. Why don’t you tell me about it, help me be a bit less ignorant.”
Glancing at the hand on him, Tim **** himself to look back at Jake's face, not realizing in doing so he leaned a little closer to the man, giving the impression of not just acceptance but enjoyment. “You want to know how a girl gets… how I got ready for tonight?”
“Sure.” Jake said, leaning a little closer, his free hand moving up, index finger touching just under her chin. “I just want to hear more about you. I want to get to know the person behind that smile that lights up the room.” he said before leaning in, his lips kissing her lightly.
Tim’s eyes went wide as their lips met. It hadn’t even lasted a full second and it took even longer for his words to sink in after the small intimate moment. “Emmmm!” The worried sound escaped Tim’s closed mouth before taking another swig from the wine.
The second bottle of wine appeared on the table without Tim really noticing it being ordered. The server refilled both glasses, Tim’s fully empty glass and Jake’s half drank one before leaving the bottle. Tim of course didn’t protest, the beverage was not to his liking specifically, but whatever its alcoholic content, it made his anxiety feel like less of an issue. Not that it went away, but just less of a problem. The first bottle had left his head light, his body loose, and another glass seemed like the best way to keep steady in the whirlpool his mind had become. ‘He kissed me… Jacob freaking McGraff kissed me!’
While lost in his own thoughts, Tim felt something unexpected. Jake’s hand settling on his knee.
The heat of it bled straight through the thin nylon, heavier than any of the thoughts dancing around in his mind, pulling him back to the present and causing him to fully freeze in place. The weight, the warmth, the deliberate pressure of a man’s hand on his leg, the thumb moving slightly up and down. Every nerve under the pantyhose came alive, a tingling awareness spreading up through him. ‘That feels good…’ Party him felt like melting in a way some did when getting a massage, his already intoxicated mind just wanting to move with it even before Tim knew he was already that far gone with the wine before something snapped to the surface. ‘Too good! It shouldn’t feel good… but oh..’ The silky barrier of the nylons seemed to amplify every shift of the palm, turning a simple squeeze into something electric. Tim’s chest tightened in panic even as his body betrayed him with a low, traitorous thrill. “Oh…” The word came out with a long breath.
Tim knew he did not like guys, not in the way, he wasn’t gay. He knew he liked girls… loved girls, had touched himself more than once to them online. Still the shiver that ran down his spine was undeniable.
Jake read her little shudder, along with the sound escaping her little lipstick covered lips, as the permission he needed. Sliding his hand up higher, fingers tracing lightly over nylon as if savoring the texture. He could hear Tammy’s breath catch as her lips parted, her bottom lip quivering.
Looking into his eyes, Tim **** his mouth closed as he whined. Not just from the pleasure that ran through him that he knew shouldn’t be there, but the pure wrongness of it all. He had felt so turned on earlier from the material and that had been wrong enough on its own and yet it somehow got worse. Not fighting back, pushing the hand away he once more took a long pull of the wine glass like he was trying to drown his pounding heart was the beverage.
“Glmmm!” Mouth full Tim almost lost it, spit out as the hand on him slid back down and then up again. The sound itself, a mix of almost spitting it out, **** and the unwelcomed and unintended sound of pleasure bubbling up as the fingers trailed along his leg.
“Cute,” Jake murmured, fingers touching her hair lightly as she acted all s hy again. “You blush so easily.”

Tim shook his head quickly, too quickly, trying to deny his words, the feeling, and the entire situation. The next thing he knew, the hand at his leg shifted, Jake’s other hand rising once more to catch his chin, tilting his face upward. The kiss… another kiss landed softly at first, lips pressing and testing. Jake’s mouth was warm and faintly tasted of red wine. His lips were firmer than Tim expected.
Tim’s body stiffened, panic spiking sharp, yet not nearly as sharp as the anxiety let it spike at the man’s first time, the wine dulling things. Then the hand at his thigh squeezing again and the sensations collided. The silky friction along his nylon covered legs, the spreading warmth of ****, the slow deliberate press of Jake’s mouth against his own. It sent a dizzy wave straight through the nineteen year old. ‘No! Its wrong! Wrong, wrong…’ The shiver that ran down Tim’s spine did not feel wrong at all.
Jake deepened things gradually, coaxing the girl more as she melted into him. His lips parted, brushing and tasting, trying to draw her more into things. While he didn’t care about the others around, he also knew the girl was nervous about the date, the shy little things and he wanted her to focus just on him.
Tim had never kissed anyone before. He did not know how to angle his head or when to part his lips and found himself just following Jake’s lead, letting himself be guided by him so easily. It felt good enough that he fell into the rhythm he was led into. His inexperience only sharpened every sensation, every press of lips, every faint tug sending heat racing through him. The softness, the warmth, the faint taste of wine shared between them. Kissing felt good, no matter what his mind told him it was shockingly good.
“Mmmmnnnnoooo” He made a muffled pleasurable noise that slowly morphed into a protest. In desperation Tim pulled back and without even looking at the person who had been kissing him, Tim lifted the glass again, drinking it fast, as though the wine could excuse him, as though it could give him a reason not to kiss back even as his lips tingled slightly in enjoyment from what they had just been participating in.
The more Jake touched, the more Tim drank. His glass emptied in quick pulls. He did not notice how fast until Jake laughed softly against his mouth. “Cheap date,” Jake teased, his thumb stroking Tammy’s cheek.
Tim’s head spun, dizzy with **** and new sensations. Jake’s arm sliding around his waist, pulling him in closer, lips pressing in again with more insistence. His other hand still caressed along Tim’s nylon-clad thigh, stroking upward, tracing deliberately higher with every pass. The silky texture made it worse, made it better, every shift of fabric over skin setting off sparks his body could not deny.
Tim leaned without considering anything, drunk enough that his body sought warmth and pleasure where his mind screamed retreat, though his body acted as if it hadn’t heard the command. Jake’s words and touches wrapped around him like the music itself, slow and deliberate, filling him with panic and arousal together.
‘Tammy would like this. Tammy would smile. Tammy would… would… Oh his hand and and… his tongue feel so good.’
His lips tingled and his legs trembled. When Jake kissed him again he did not pull back. It was awkward and clumsy, his first kiss, but it felt good all the same. The taste of wine on Jake’s mouth, the warmth of another’s lips guiding his, the hand stroking his thigh through smooth nylon, the **** buzzing through his veins. Together they overwhelmed every thought he tried to cling to. For all his panic, for all his protests, his body knew the truth of what he felt.
Jake’s smirk deepened as he slid an arm around Tammy’s waist.
Tim didn’t react, not to a touch less intimate than what was already happening but without a reaction he was unprepared for what came next. Jake’s other arm scooped under his knees, lifting him clean off the stool in one fluid motion.
Letting out a startled gasp, Tim’s arms instinctively clutching at his aggressor’s shoulders. He had never been picked up like this before, not by anyone, not like a girl carried across a threshold. The intimacy of it stole his breath, the casual strength behind it making him feel light as air, weightless, weak, powerless in Jake’s hold. His heart pounded as Jake shifted him, settling him neatly into his lap as though he belonged there all along.
Perched on Jake’s thighs, the hem of his dress riding higher, nylon shimmering under the warm lights. Jake’s hands were on him instantly, one steady at his waist, the other gliding down his leg to stroke along the smooth fabric. Tim’s body went rigid like it had on the first kiss, his face hot, yet the deliberate caress of fingers over legs sent a shivers racing through him all over again.
Then Jake’s mouth found him once again.
This time the kiss carried no hesitation. Jake wasn’t probing, seeing if she liked it, he already knew and wanted more of the little eager girl. Lips pressing firmly, parting, tasting. Her surprise, her stiff body pressing into him, clutching him softened soon after as he parted his lips, sliding his tongue across her own as he deepened the kiss.
The feeling of Jake’s hand sliding higher along his leg, moving just past the hem of the dress even as it was pulled up higher thanks to the unexpected seating change. The touch along the nylon surface of his smooth shaven skin magnified every bit of it until Tim’s nerves lit up in sparks and exploded in fireworks. His thighs clamping together as blood started to rush down from his mind to his lower reaching, every part of him quivering under each squeeze of the older boy’s hand, every turn of his head, at every kiss. Heat pooled low in his belly, his hips shifted, rocking without thought slightly as he sat in the man’s lap. None of it was a thought, it was all just action and a dulled distracted mind.
The kissings, the touching, the groping deepened further, their tongues colliding and brushing against one another the entire time while Tim… Tammy made a muffled noises. Some of them could have been half protests from his fading mind, but most of it was from pleasure. It hadn’t been pure lips touching one another, there had been breaks for breathing, and Tim knew he had drank some more of the wine, not that Jake had ever stopped kissing him in one way or another during those times, but at the same time he couldn’t also recall later any specific time while sitting in his lap that he had pulled away. His lips stayed caught, tingling, clumsy but eager. Time blurred, losing track of how long they sat like that, tangled together, kissing as though the crowded museum had vanished around them.
A sharp sound cut through the haze. “Ahem.”
Tim jolted, eyes flying open. A man in a suit jacket stood nearby, clipboard in hand, his polite smile hiding disapproval. It seemed like they were a manager, but at the same time he was feeling woozy and hadn’t ever looked at the server before, making him unsure if it had been the same person.
“Perhaps” The voice said with some firmness in it. “the two of you might like to continue your evening in the galleries. And if you’re ready, we’ll settle your tab here.”
Flushed scarlet, Tim scrambled off Jake’s lap, nearly stumbling in the process. His lips still felt the effects from what they had just been doing, his legs trembled, and his chest felt tight with embarrassment, but was unable to truly think of other things than the lingering pleasure.
Jake only leaned back in his chair, utterly unbothered. He reached for the bill with, sliding cash into the folder before the manager slipped away.
Tim glanced at the table and froze, seeing three empty bottles that stood in a neat row. His own glass, sitting there full and Jake’s empty. His head spun as he tried to count back. ‘Did I drink too much? No… Jake really drunk that much? Wow he can really hold his ****.’ He thought, not realizing nearly all of it had been his own actions.
When Jake rose, he caught Tammy at the waist again, steadying her.
It caused Tim to blink rapidly, appearing to be Tammy fluttering her mascara covered lashes, when he was just trying to get a grip of himself. The floor seemed to tilt so the hand around his waist had actually been helpful for a change instead of something unwanted. Still uneasy and not wanting to fall, Tim leaned on the taller and clearly stronger man for support.
“Come on,” Jake said with an easy grin. “Let’s go see some art.”
“Hmm… yeah…” Tim said, reaching over to take the glass from the table with him. Hearing the clicking of the heels once more as unsteady as he had been, Tim looked down at his feet, a thought skipping his mind and going right to his mouth. “I like seeing a girl wear heels, they don’t always, I mean they should wear them more, I mean… Even my feet look hot in them and I’m a boy.” he said, not just failing to parse what he said unfiltered but also failing to notice the small bump, the little bulge in the front of the red dress at his own excitement."
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Frat Pledge
Botched Pantie Raid
Timothy Thompson a freshman at college wants to join the fraternity his father was once apart of and move past his lonely years of being a kid with little to know friends. The problem is his constant cheerfulness makes the vice president of the frat want him gone, so he sends him on a pantie raid in an attempt to make him go away. Things get worse for Tim when he is caught, and the girls want to teach him and the fraternity a lesson.
Updated on Dec 1, 2025
by Nicegent42
Created on Jul 2, 2025
by Nicegent42
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