Jeremy was in heaven. For months his roommates and him had been stuck in lockdown. Months of only leaving the house for groceries, months of sitting around watching the same old shows with the guys, months of boredom and online classes. And above all, months of the worst sexual frustration he’d ever felt. It was affecting all of them, he could tell the guys were on edge and irritable after months of jerking off alone instead of their usual rotation of booty calls, but at least they were able to get themselves off. But with the thin walls, close quarters, and lack of privacy in their house Jeremy hadn’t had the chance to indulge in his hobby since lockdown started, and he was ready to burst.
It’s not like his roommates were jerks, they were just regular everyday guys. Wings and beer at the sports bar type guys. The type who would probably be uncomfortable to discover that their roommate liked dressing as a woman. So, he’d kept things hidden as much as he could. He knew it wasn’t healthy to hide it, and he’d been planning to come out as trans forever, ever since he secretly started hormone therapy almost a year ago. When lockdown happened, though, being stuck at home all day with the guys made the prospect of coming out so much worse. What if things went wrong and he had to spend all day every day locked in a house with a bunch of guys who would judge and ridicule him, or worse? He wasn’t willing to take that risk.
This weekend, though, was his chance to change all that. His roommates had managed to book a campsite a few hours away, and he was looking forward to spending the entire long weekend as his alter-ego, Jessica. Before lockdown he took every chance he could to spend time as her: dressing up sexy, taking some photos, sometimes camming or RPing with guys online. Having his roommates around all the time meant he hadn’t been able to be Jessica in months. Where Jeremy was shy and quiet, Jessica was confident and desirable. Jeremy was a little bit nerdy and clumsy, but Jessica was sexy and proud of it. Jeremy was aimless, but Jessica knew exactly what she wanted and how to get it. Being Jessica allowed him to express a side of him he normally kept hidden, and he lived for those times. She’d even built up a bit of a following online and had started a countdown, promising her fans that this weekend would make up for the months of no new photos.
The last couple weeks since the guys booked the trip had been spent preparing for the weekend. During grocery trips he made small detours to the sex shop or the drugstore to stock up on supplies he kept hidden in his closet. He’d done some special coding on his webcam software to give it some additional functionality, and he’d even changed his diet to keep himself clean. He was planning on making up for months of lost time with a weekend of luxury and sexual abandon.
After what felt like an eternity the guys left for their trip. Jessica took her time getting ready. She started with a bubble bath, slowly shaving every inch as she relaxed in the tub. She loved how the bubble bath made her skin smell like lavender, even after she’d drained the tub and dried off. Wrapping herself in a fuzzy bathrobe, she made herself a cocktail and did her makeup. She was out of practice, so she went slowly and carefully, plucking her brows into a thin arch, applying a smoky eyeshadow and sharp winged eyeliner, and choosing a deep vampy red lipstick to finish it off. Her hair had grown out over the past few months into a cute shoulder length, and when she wore it down instead of in her usual ponytail it nicely framed her face, giving her a pretty, sophisticated look. She blew herself a kiss in the mirror and winked at herself, and even she had to admit she’d outdone herself. She didn’t just look good, she looked hot. She snapped a quick face selfie and posted it online with the caption “sneak preview… wait til you see the rest 😉”.
She took her time getting dressed, selecting some basic pieces from the lingerie she’d acquired. She had been so careful to resist the temptation to try it on, letting the anticipation build until it was almost unmanageable, that her skin felt electric as she put on the black lace panties. She caught her breath as the smooth silk slid up her soft, hairless legs. Her skin had gotten so much softer with the year of hormones, and it’d been so long since she shaved that she hadn’t realized how shapely her legs had gotten. Next came a black bra — she’d bought some more eye-catching pieces, but she figured she could start with the simple and classic and really draw out the reactions from her fans, moving on to the fancier lingerie as the weekend went on. The ad for the push-up bra promised two additional cup sizes, and she was pleased to find that it delivered, giving her small but growing breasts the illusion of cleavage. She’d gained a bit of covid weight and between the hormones, the weight gain, and the lingerie she was pleased to find her figure had filled out into some nice curves. She spent a few minutes in front of the mirror admiring herself – even the little bulge under her panties was cute.
Next came a black garter and sheer black stockings. She shivered as she worked the stockings up her smooth legs, and she took her time carefully buckling them into the garter and lining up the seams behind her legs. That 50s look was popular, and although she hadn’t had the budget to buy a fancy swing dress, she thought seamed stockings and a garter would give enough classic allure to make it worthwhile.
She giggled to herself when she picked up her out, imagining what her roommate Mike would think. A few weeks ago, they’d come home to find Mike watching porn on the living room TV. It was just some cliché video of a woman in a cheerleader uniform being passed around between three guys, but they had been teasing him about it ever since. She had joined in the teasing but had secretly been pretty turned on by the video too. She’d watched it a few times since then and had even bought a similar cheer outfit – she thought her fans would like it, and she did look hot in it. The blue pleated skirt barely touched the top of her stockings and if she bent over at all it lifted enough that her bum showed. She snapped a few photos and posted them with the caption “What should my cheer be? Is S-L-U-T too much?”. Her previous selfie already had a few dozen comments, and she eagerly read through them. Her fans wanted to see her — they wanted her. Soon enough, she thought.
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An hour later, Jessica was ready to record her video. Her photos had dozens of comments and likes, and her followers were eager to see her. She mentally ran through her checklist for recording: she’d spent some time cleaning herself inside and out and fingering herself a bit to stretch herself out for the video. Her webcam was set up pointing at her bed and she’d double checked her angles and lighting to make sure it was a flattering view. She’d spritzed a touch of perfume and put on some low music to set the mood and lined a few of her toys on her bedside table within easy reach.
She hit the record button and the red light winked at her as she started, rubbing herself and showing off for the camera. She warmed up for a couple of minutes, giving peeks up her skirt, massaging her breasts together, and flirting with the camera before starting for real. She took a plug off the shelf and lay back on the bed. She held her legs up and slowly fingered herself, enjoying the feeling of her fingers inside her, letting the anticipation build. When she’d had enough of her fingers she eased the plug in, giving a little gasp for the camera as it popped fully in. She hadn’t had anything inside her in so long and the sensation of fullness and stretching made her feel amazing. Slowly writhing face down against the bed, she played with the plug and slapped her ass a few times, giggling at how her ass jiggled against her hand. She groped herself, leaving marks where her fingers dug into her ass.
Jessica was having fun, but she wanted more. Grabbing the dildo off the table, she teased the camera by staring into it and giving the dildo a few agonizingly slow licks before she started kissing the tip, popping her lips over the head, and eventually taking the whole thing into her mouth. She gagged a little as she pushed a little too far onto it, but the gag and drool when she pulled it out got her even more aroused. With the plug in her ass and the dildo in her mouth she imagined being stuck between two men, both eagerly using her. She held the dildo with one hand, working it in and out of her mouth as the other explored her body, rubbing up and down her thighs, pulling up her skirt and spanking her ass, and feeling and squeezing the curve of her breasts.
She worked the plug out, positioned the dildo behind her, and slowly eased herself down onto it, giving the camera a good shot of it sliding into her thick ass. She moaned as she felt it fill her up and couldn’t help but close her eyes and reach down to touch herself. She started rocking herself back and forth, riding the dildo. She could feel the pressure as the head massaged her prostate, and she felt herself drip a little and leave a dark spot on the front of her underwear. Her hand slid into her underwear and she pulled her cock out, rubbing it gently as she rode the dildo, riding faster and faster as she moaned and the pressure grew. She closed her eyes as she sunk into the rhythm, bouncing up and down on the cock as she cried out in pleasure.
She lost track of time completely as she fucked herself, building up to a massive orgasm. She screamed as she came, catching her cum in her hand. With her eyes still closed she relaxed back letting herself settle down onto the dildo, moaning quietly as she basked in the afterglow. Playing it up for the camera, she spooned her cum off her hand into her mouth and slowly batted her eyes open.
She froze. Standing in the doorway were her three roommates, jaws wide open as they stared at her.