Chapter 16

Tim barely noticed when the museum’s hushed glow gave way to the cool press of night outside the building. The wine and Jake’s steady hand at his back had steered him along so smoothly that by the time awareness returned, the polished facade and velvet ropes were behind him. A faint breeze teased at his hair, carrying the distant hum of traffic, only then did he realize he was no longer being escorted around to look at paintings that he had hardly even paid attention to when near them. “Are we…” Tim craned his neck to look back to the glass doors they had just walked through. “Umm, leaving?”

“Yeah, but don’t you worry your pretty little head, our time together isn’t over.” Jake said while his mind was thinking more about what they would be doing shortly and what she should have her mind on. ‘While not worrying your pretty little head, you can think of what you are going to do with my little head, while you give me head.’ he thought, chuckling at his own joke.

The Mustang loomed only a few steps away by the time Tim caught his bearings, dark metal catching fractured reflections of the parking lot’s patchy lights. His head tipped slightly as if the car had appeared out of nowhere, surprise flickering through the haze. He couldn’t even remember crossing the last hallway before the exit, only that he had been walking, tucked close against Jake’s side, listening to his footsteps echo. ‘Its not over? But we are leaving…’ despite dreading and feeling like he wanted to crawl into a hole to die when this **** date started, now Tim felt a sense of loss. One he didn’t fully understand and didn’t have the wherewithal to process.

Before he could gather his thoughts, the hand touching his lower back shifted and cinched tightly at his waist. In a smooth motion, almost like it had been practiced, the taller boy turned him, pressing his back against the Mustang’s cool frame. The chill of the car’s surface didn’t make it past the extra layer of the corset, but above that it seeped through the thin dress, clashing with the heat that flushed his cheeks. The purse sliding down his arm.

Then came a kiss, one that landed seemingly just as he had finished the turn. Tim found himself pressed between the vehicle and the strong man, causing Tim to let out a a muffled gasp into Jake’s mouth. “HHMMM! Mmmm…” The shock fading as he sagged against the car as Jake’s lips moved over his own, Tim clutching his hands, grasping Jake’s jacket and shirt, not caring that he couldn’t move from the spot. ‘That feels… he is so confident, I wish I could… just keep feeling this…’ Tim’s mind went on, shifting from one thought, it left unfinished before moving to another and getting lost in the moment. The faint taste of the red wine spilled between them, heady and sharp, while Jake’s thumb stroked slow circles at his hip. The steady grip holding him in place, giving Tim a sense of being small and fragile, but for the first time it wasn’t a bad thought about himself, it was something good, something that Jake clearly liked.

Tim opened his mouth, lips parting without thought when he felt Jake do the same, a touch from his tongue to his lips making the nineteen year old follow the more experienced person’s lead without a moment of hesitation. Their mouths tangled, tongues brushing, wet and messy until his chest burned for air. Tim twisted his head aside, panting against Jake’s cheek. “Breathe,” he stammered, the word coming out in a pant and heavily slurred. “Gotta… breathe… and… I need to sit down.” His hand drifted weakly toward his aching calve, it was much easier to raise his leg pressed up against the car and steady in Jake’s arms. “Shoes… my feet… they hurt.” he winced, it wasn’t a sudden spike of pain, but one that had been growing since the first step in the shoes.

Jake chuckled, something he found himself doing a great deal around the pretty little blonde, her stumbling admission was the cutest thing. “Alright, babe.” His voice didn’t have even a hint of annoyance at the stop to what they were up to, he knew they weren’t done, he wasn’t done and knowing she had more she wanted to do to him tonight. Reaching past her, swinging the passenger door open, he gestured with a flourish. “Your chariot awaits ma’am.”

Tim sank gratefully into the seat, the hem of his dress pulling higher across his thighs as he got into the car in a rather unladly like fashion that left Jake grinning wider before closing the door with a heavy click.

“Hmmm” Tim closed his eyes, leaning his head back into the seat as he pulled the heels of him, before flexing his pantyhose covered toes at the sudden freedom from the imprisoning footwear.

Jake slid into the driver’s seat, the Mustang rumbling to life with a low growl as he turned the key. He didn’t even bother touching the gearshift. Just letting the car stay in place, engine idling, headlights not even bothering to turn on the headlights, wanting him and his date to stay in the protective shadows in the parking lot. Only a few lamps still burned at the far end of the lot, casting a dim light at best. Tammy sat there, shifting slightly in his car, her eyes closed and a contented smile on her face. ‘Adorable…’ he thought, taking her in.

Curling against the seat, Tim’s pantyhose covered toes flexing with relief as he wriggled them more, still feeling the dull throb left by the heels. His chest rose and fell fast, though not in a gasping motion the tight grip of the corset no longer felt as if it was a vice, but something that helped give him support all while the wine buzzing through his head. The quiet between them should have let him slip off to sleep with all he had, but instead it made the heat from earlier spread deeper in his chest. Opening his eyes, Tim blinked a few times as he glanced toward Jake, his date… unsure of what came next. “We are, umm not done?”

Jake’s hand found the back of the passenger seat, his body leaning just slightly across the divide. His smirk in place, but being something more predatory than just his natural smugness. “I’m not done, and you have work to do, Tammy. Come here.”

The dress wearing teen felt his stomach flip. Those last two words landed like an order more than some suggestion, and before he even thought about it, he was leaning across the console, being pulled in even closer by Jake’s powerful arm. Their lips met once more, something soft for a heartbeat before Tim felt Jake press in even harder all while pulling him in even more. ‘Is this what happens on all dates? I really need to… yeah, that would be nice.’ His thoughts went to the girls he had been so close to seeing fully nude while staying in their shared room, kissing the tall athletic Emily with her lean but strong body, before it was Sarah, the petite little thing that could allow him to pull her in. Telling her to come here, just like the confident Jake that… the image shifting in his mind of the man he was pressing into, being controlled by him. The kiss became something more passionate all too quickly, Jake’s tongue sliding against his, and Tim’s whole body jolted at the wet, messy contact. “YEMMM!” The feminized boy groaned, trying to say the word yes with his mouth full at the same time letting out a sound of pleasure. He had never kissed like this before, never kissed someone before at all, and the sloppy rush of it overwhelmed him. He blew out air through his nose, able to still smell the wine that was heavy on his own breath and it spilling into the kiss as drool slicked the corner of his mouth.

Jake seemed unbothered, his natural confidence coming through even as he lost himself in their passion, the rhythm, coaxing Tammy, his girl to follow. Each tilt of his head, each tug of his lips had Tammy scrambling to keep up, her small hands clutching at him like she needed him as a lifeline and it just revved her personal engine that much more, driving him wild with lust.

Taking her wrist, Jake pulled her hand down downwards in his lap. Without breaking the kiss, he pressed her palm firmly against his crotch. Against the denim covered bulge that she had created, he wanted her to feel what she had done to him, what she was going to see too in a moment. Holding her hand there he bucked his hips twice slowly. ‘God yes!’ he thought with a desire that felt more like a need than a want.

All the while Tim felt the warmth of something firm in Jake’s pants, the texture of the jeans, it felt off, something wasn’t right but he also couldn’t spare a thought, only closing his eyes as the touch of Jake’s lips on his own faded before it came again, this time on the base of his mostly exposed shoulder. Then another a little higher up and another. “OH!! AHH!” Tim’s pulse hammered in his ears. Heat rushed lower, his own body betraying him. He was already hard, already leaking into the thin panties, the dampness seeping through to the front of the dress. “Yes! Yeeeahhhhaaa!” The fabric tented slightly from him having one new experience after another, like cum shooting from himself without even touching his dick, it still not really processing what was happening while touching someone else's.

Jake didn’t notice what was happening with Tammy… Tim. He was all too focused on his own enjoyment and the eager girl telling him how excited she was as he pressed her hand into his dick. “You are so fucking perfect!”

Tim whimpered into the air as trailing kisses moved up to the nape of his neck, drool slipping down his chin as Jake pushed things further. ‘It’s wrong,’ he thought, dizzy, clinging to Jake with one hand, squeezing the other on his jeans, feeling something different as he did. ‘It’s so wrong, I’m…. I’m fucking cummnig, oh god, oh god, this is… but it feels so good. I have to keep Jake happy. Yes, yes… Emily and Sarah told me to. I need to… I need to…’ His thoughts tangled as Jake’s hand squeezed his tighter against the hardness in his jeans, it not processing that he was adding not just friction but a firm pressure to Jake’s hardon.

His hips shifted restlessly in the seat, dress riding higher, thighs trembling as the mess between his legs spread warm and sticky. His body didn’t care about the excuses anymore. It only cared about the closeness, about Jake’s commanding presence filling the dark, and within it all the very air in the car felt thicker, heavy… Tim didn’t know if it was the air blowing from the vents or him just feeling overheated from what was going on.

Jake’s hand slid from Tammy’s shoulder down to his own lap, fingers tugging at the zipper of his jeans. The sharp rasp of metal teeth sounded louder than the muted engine rumble, pulling his date from her own **** and lust full daze from all the kissing. In the dim light he could see her hazel eyes go wide as she focused in on what he had pulled free even as he continued to adjust his pants.

Tim’s breath hitched. The hard length of the male member… Jake’s cock, it stood out stark against the shadows, swollen and flushed in a way that no screen, no late-night video on his laptop had ever prepared him for. He gasped softly, a raw sound that slipped past his lips before he could even swallow the excess of saliva in his mouth. Dicks he had seen, not that he had been really looking for them or at them with any purpose, porn was a thing, he had seen things, but it was forgettable. This was right in front of him, he was practically leaning over it, leaning over Jake’s cock and it was only inches from him.

“This,” Jake said with quiet triumph, his smirk sharpened into something hungrier, “is what you do to me, Tammy. So just like you wanted… this is all yours.”

The words pierced straight through the fog of ****. Tim’s head spun as those words tangled with his own thoughts, it all jumbling and crashing together too fast to sort. ‘I didn’t…I never… he thinks I want this… him?’ The contradictions tumbled until they burned away under a single truth. Jake was hard because of him. ‘He is turned on because of me!?’ The thought seemed so strange, his own arousal and what was happening in the panties he wore not coming into the picture at all. ‘I turned him on…’

As the thoughts sprang up, and then mentally spoke over or clouded over, Tim’s eyes stayed locked on what he was seeing, unable to look away from the dick that was not just longer than his own, but thicker. ‘He is a real man…’ A dizzy wave of shock mingled with something warmer, heavier, that curled low in his belly. “I did that? Me?’ His legs pressed tighter together, the wet cling of the panties against his leaking tip a sticky reminder of his own state. He had never thought he could turn anyone on, much less someone like Jake, a man of pure confidence, a man that seemed to just snap his fingers and get some hot girl to come to his side or at least that was how Tim thought of him.

Tim’s lips parted, not in protest but in awe, his chest tight with the strangest, most impossible pride. “Your… so big!” The dress wearing boy was going to say hard, but with one thought commingling with another the sentences came together in an unintentional way.

Jake’s hand lingered on the base of his member for a moment, hearing Tammy tell him how big he was did great things for his ego and the way she just stared at his dick, her lips quivering a bit of drool still sliding down her mouth made him unable to resist stroking himself once as she watched him do it. “Go on, Tammy. You know what I want. What you want.”

Tim’s mouth didn’t go dry, his saliva production had increased so much from the kissing and now he felt it sliding from his mouth, as if it was going to drip down onto what he was unable to tear his eyes from. ‘He thinks I want this… Do I? NO! No… I can’t I wouldn’t, I like girls, but, but I made him hard and I… that was just from the kissing though, it felt good I can’t be blamed for that but… He’s hard because of me. I made him like this… I did this. Emily and Sarah said I had to, but… I kind of… I want to… Fuck… I do want to.’

Swallowing the excess saliva, Tim shifted in the seat to move from sitting to being on his knees, not truly looming over what he had created, what he had done to Jake… to another boy. ‘Its okay, I have to do this, Emily even gave me condoms, she knew… its fine, its fine, Tammy would want this, yeah I do, fuck I can’t believe this.’ His knees pressed into the leather seat as he shifted, trembling with the effort of moving closer. The smell of Jake, cologne that he had paid almost no attention to before was there, along with something more, something raw, a description that made little sense to him but it was still the word that came to him as his pulse started to race faster.

Jake’s hand slid into his date’s wavy hair, coaxing and guiding her to her goal that he was aching for her to give attention too. “That’s it,” he said, voice almost a growl. “Be a good girl for me.”

Tim swallowed once more, this time much harder. His lips parted. The world narrowed to the warmth of Jake’s hand at his head and the impossible heat radiating inches away. ‘I shouldn’t… no, this isn’t right, I’m not gay, I like…’ he thought more, but as he pressed his legs together, his ass in the air as he leaned down he could feel how sopping went the underwear he was wearing was from his own explosion of cum. It was hard to refute the desire he felt from Jake, all the care, the attention. He was so much stronger, that much more confident of a man and Jake wanted him. ‘It isn’t being gay… Tonight I’m just Tammy and Tammy would want to do this for him. She would want to make Jake happy, just like Emily and Sarah said, yeah, so it isn’t gay. It's just a girl with her date. Nothing wrong there, her just happy to make him happy. Yeah…’

Not really sure what he was doing, his own mind babbling on and on to justify what he was about to do, Tim kissed the top of the dick in front of him, even then doing it wrong, with his mouth already partially open and ending up giving only part of the tip a kiss, but still one with much more saliva than he was expecting. Feeling the fleshy, sponging substance with his lips was yet another new experience for the nineteen year old, one he wasn’t going to back away from. Often in life he went along to get alone and right now he wanted… Tammy wanted to get along and really wanted to go along with it all.

Reaching out with one hand Tammy, because he couldn’t think of himself as Tim, he was a nobody, Tammy was the one that people, that Jake actually wanted. Tammy kissed the tip of the cock again, this time her mouth closed. Reaching out to grab the base of it, feeling the girth of it all in her fingers, the warmth of the dick that was so much bigger than her in an almost comical way, or at least it would be if Tim wasn’t a joke of a man, no like Jake. Things hadn’t started as hero worship, just Tim trying to do his best for him, to impress him, wanting to be friends with someone like him, but it had grown to something more and a lot of that could have been feeling like he was finally belonging to something, as Tammy he could, she could belong.

She slid her hand up from the base of the cock, his ball sack tight over his dangling bits that made Tammy giggle drunkenly as her hand light touch trailed up to the tip and then back down again. “I really made you hard.” She said, her voice in a half whisper, as her hand tightened more to feel what it was like to add a tighter pressure.

“Yeah… yeah you did baby.” The hand that Jake had on his own member moved to the girls lifted ass and slid it along to the edge of her dress before sliding it back up, but this time under the red fabric to slide along her pantyhose covered ass, feeling the lines of her panties underneath as he gave it a little squeeze.

“OH! Hmm.” Tammy sounded, glancing up at the man that wanted her, feeling him squeeze her ass before turning her attention back to what he wanted, what she was supposed to want. Even trying to ignore who she really was, and with her own horniness she still couldn’t proceed without hesitation, though it didn’t last long before she started again, holding out her tongue and sliding the member in her hand across it. Sliding it to the left and then the right, the fleshy member had a taste that wasn’t exactly appealing, but feeling it pulse in her hand sent a pulse of euphoria at Jake’s enjoyment.

Not long ago it had been Tim rushing around trying to impress the upper classmen, trying to outshine the other pledges. So often in life he had been ignored, he just didn’t fit in. At one point in high school he had tried to think ahead and did research on some computer RAM after hearing some of the nerdier classmates discussing it. He found a great deal on a website, seeing the sticks were on sale and tried to insert himself into that same groups conversation with his little nugget of information, but he wasn’t one of them. Just an outcast, not tech savvy, or brilliant and soon as they asked a probing question about the type of RAM he was at the end of his rope, not even knowing there were different types.

College was a place to reinvent himself, to at least be part of something and with luck and effort perhaps be part of a popular crowd. His own father said this was a time to grow up, to put childish things behind him, to become a man. Yet here he was, finally getting the acknowledgment he wanted, he deserved but he was hardly becoming a man… Tammy was getting the attention, the praise, she was pretty, while he was just plain Tim. The mental illusion that he was Tammy, a girl, she, her, girl, young woman on a date, all of that couldn’t stay in place for longer than a few seconds. Lack of concentration, a mind that felt like it was trying to think through a bog didn’t help the self deception, but still hearing someone groan in pleasure at his efforts was a reward that brought in a sense of pride. He wasn’t Tammy, but it felt like she was still there, she needed to be here for Jake. College wasn’t helping him become a man and against his own will it was reshaping him into a woman… at least of a sort.

Opening his mouth, saliva dripped down before descending to welcome the member inside him, Tim sucked on it, turning his head from left to right before pulling free. It wasn’t so gigantic that it didn’t easily fit in his mouth, not like some insane things he had seen in porn before, but it still was more than a little… impressive compared to what he had been not so blessed with.

Groaning happily, Jake kept one hand held firm on the girl's rear end as he glanced down. It was more like she was teasing him, just giving him a hint of what he wanted and as pleasurable as it felt he wanted more. When she had just finally taken him into her warm wet mouth, she had pulled back off him, her hazel eyes looking back up to him. The animal part of his brain just wanted to shove her back down, to fuck her face, hard and fast, but she was having her fun too, she had made herself clear on what she wanted. He had been bold… too bold and a bit stupid to bring up the topic of getting head at the start of the date, but it had paid off. She had slapped the roof of his car when they arrived at the art museum as she practically jumped out before he had even put it in park. Tammy had been in a hurry for what she wanted and then had practically turned the museum into a two person party as she took in the wine.

“Am, am I doing a good job?”

Jake heard her ask, unsure if this was that shyness, leading to uncertainty in the girl or if she was just teasing him more he answered all the same. “You are amazing, what you are doing is amazing.” His chest rose and fall rapidly, not from some great effort, but just from how his own motor was running.

‘Amazing, I’m doing an amazing job!’ Tim thought, sliding the fleshy object back into his mouth and lowering himself down onto it more than before. He had watched girls do this so many times before, never in person, but it always seemed like such a sexy thing. Seeing their lipstick covered lips stretched out over a man, them moaning enough that it was clear they were getting off from it as much as the man was. That part wasn’t happening at all for Tim and he just assumed it was a natural girl thing, having no life experience to tell him how much of it was just a show for the porn production. Still he emulated what he had seen, making sounds that felt like music to his ears when he was beating himself off.

It was more difficult than he imagined, not that he imagined doing this before. Breathing was difficult, keeping his jaw open was a strain that was unexpected and he felt like he was going to gag and that was with only getting half of the thing in his mouth. Still he kept up the effort, the head tilt thing seemed to be something Jake liked and already he had tasted something new, something slimy and salty. It wasn’t a strong taste, but what had started to leak from the cock in his mouth was unmistakable. He was actually making Jake cum, or at least the first hints of it. The praise of doing something he had never done before and being amazing at it made him redouble his efforts when he tasted the proof of the man’s words. “MMmmmmm, MEEEE!”

With all the excitement in the car, neither person had an inkling of an idea of what was going on outside the vehicle, let alone what events transpired in the parking lot itself. Even before they had walked across the mostly dark parking lot they had preoccupied and hadn’t noticed someone watching them, following them. Emily hadn’t gone into the museum to watch the little date, to see her ****. It wasn’t that she wouldn’t have liked to, but her own budget was tight and paying for entry to the night time event hadn’t been something she had budgeted for. Outside she had leaned against the building, glancing in through the windowed front, hoping to catch them and take photo or better video evidence with her phone, but mostly she just waited.

The entire time building up what little Tammy was doing with her big strong arrogant piece of shit frat leader. He wasn’t the top of the food chain for his little boys club, but he had been the one to kick off events with sending Tim into her house, making him violate them and go through things that were private, were intimate. The freshman had done it all willingly so while he was a pawn, he still did it willingly. Her turning that pawn to her side of the game board to use as a weapon, it only made things better. It hadn’t really been her plan all along, but she also wasn’t the best at long term plans. Everything that happened so far, what her and Sarah had done for a little payback and what was going to happen to make that little payback become a true retribution was going to happen.

A panty raid, that was a relic of the past, not things that really happened anymore. It was like that old **** of the Nerds movie that had some funny moments, but over all it was cringy and at the worst down right rapey. She wasn’t going to tolerate that crap being done to her, she was not a victim and would never let herself be. Briefly she amused herself with the line from that Breaking Bad show about being the one who knocks. She could be the bad guy, the anti-hero, so long as those that were the real problem, not just here, but in life as a whole, like Jake McGraff got a true reckoning.

The young blonde’s head lifted, lips swollen, chin damp, his hazel eyes glassy in the dim light. His chest heavier than it had ever been from the forms glued to his chest and the excessive effort, it heaved like he had run a sprint, though the dizzy warmth in him came from something else entirely. He collapsed back against the passenger seat, a dazed sound escaping before he could stop it.

Jake meanwhile leaned back, smugness radiating even in the shadows, one hand dragging lazily over and through Tammy’s hair before patting her cheek. “Perfect. Just perfect. Tammy… you are perfect.” His tone thick with satisfaction, a natural post nut tiredness coming over him, his grin sharp enough to cut through it and his date’s drunken haze.

Tim’s own body thrummed, still leaking into the ruined panties, still hot from everything he had just done. His thoughts swirled, the enjoyment of what had just happened was there, but also an internal agony at it, the wrongness of it coming back with a much larger **** than before, it made him feel **** to pin the moment on Emily, on Sarah. They had told him he had to do this… though that was much more on Emily, Sarah seemed just all too happy with it, with him being Tammy. ‘Tammy!’ The name jumped in his head, like it was her fault, like she was another person to push the blame onto, anyone but himself. But she wasn’t real, no matter how he tried to frame it, he couldn’t escape the dizzying truth. Jake wanted him and that felt good. Jake praised him and that felt even better. For the first time in his life, someone made him feel wanted.

All while outside, a shadow shifted near the edge of the car. Emily’s phone camera clicking, her having collected more than a few pieces of evidence of the act. A bit of shock in her that little Tim, her creation, Tammy had actually done it. “A blow job on the first date, you are a slutty little thing.” She wanted to laugh at her own comment, but held it in, afraid those inside the idling car would hear her or that she would graduate to true villain status as her laughter turned from normal into maniacal laughter.