The Blue Dress

Ed stumbled as he crossed the threshold of the bar, and paused, wincing. He had desperately hoped his entrance would be quiet and unnoticed, providing him with relief after his humiliating walk along the busy street from his car, but he was bitterly disappointed. Unused to walking in heels, he almost lost his balance and bumped into a table by the door, loudly rattling some glasses. Combined with the clatter of the door closing, it felt like everyone at the bar turned to stare at him. He stiffly forced himself to recover his posture, smoothing the folds in his dress with his palms. He blinked anxiously and fidgeted with his phone, trying not to think about whether he'd been clocked by any of the bar patrons. If they had, they didn't seem to care; they went back to their drinks, the mutter of conversation resuming.

"Okay, I'm here" he texted. "Where are you?"

- o -

Jessie had giggled with every wince as she had waxed him. One rip, one ragged gasp of pain, one soft chuckle; over and over for what seemed like hours, up and down each leg, his shoulders, his chest. Every so often she'd tousle his hair and brush away a tear from his flushed cheek as he panted through the pain.

"Aww, what a good boy," she'd say. "You're doing really well Eddie. Not many more now." But no matter how comforting her words were supposed to be, she never lost her wicked smile and laughed softly after every pull. Each strip was a tiny emasculation, lifting every coarse hair from his skin and leaving it flushed, tender and soft; feminine.

He had tried to protest whenever she brought up the idea of dressing him up, but he had never quite been able to communicate to her quite how much it bothered him. He'd been bullied in high school for his slim, androgynous physique, and while that was years ago now, the reminder that he had never quite filled out his girlish frame still made him flinch. But every discussion ended the same way, because Jessie would always fall back on her unanswerable argument: "Well, I think it would be really hot!"

What was there to say to that? He did like it when she found him hot. So when she came home one day with bags of clothes shopping and two home waxing kits, he couldn't summon the spirit to protest. He had demurely stripped down as she requested and waited for her in her bathroom, and then sat wincing while she systematically depilated every inch of skin that would be visible under the slinky new pencil dress that hung in the next room.

- o -

"I'll be there in a bit babe, wait at the bar" was the terse reply. His stomach twisted. This was all her idea, and now she was running late? He'd only made it through the embarrassment so far on the explicit understanding that once he reached the bar he would be on her arm for the rest of the night, relying on her to shield him from disparaging glances. For half a second he looked back at the door, considering leaving and hurrying back to hide in his car, but he'd already made such a scene walking into the bar it would be far worse to leave straight away. Swallowing hard, he picked his way through the seating area to the bar, acutely aware of every step. She had coached him a little on how to walk in heels, but he still wasn't sure he was doing it right. In his mind the whole bar turned to look at him as he passed, but he kept his own eyes fixed forward, locked his attention on a stool at the end of the bar, and concentrated on finding his way there, step by clacking step.

He had been so focussed on completing this task that he was completely thrown for a moment when the server asked for his order. He froze like a rabbit in headlights for a long moment, his mind scrambling to pick a drink that someone wearing this outfit might order. When he finally managed to croak "a gin and tonic, please," he was so aware of his voice it came out as a strangled whisper. The server's expression was unreadable. She was a woman in her thirties wearing heavy eyeliner and a band t-shirt, and there was no hint beneath her bored expression whether she noticed anything amiss about this customer. Perhaps she wouldn't have cared even if she had.

After checking three times for a new message for Jessie, he finally forced himself to put the phone down and took a timid glance around. To his relief, nobody was looking at him. It was still early, in the lull before the evening started properly, and there were only a few groups of people sitting at tables. One other man sat two stools down at the bar, in chinos and a casual jacket, nursing a beer. Recognition struck him like a bolt of lightning.

Ed knew Jack Allen from high school. Not closely — he'd been in the year above — but they would both certainly know each other on sight. Throughout school, Jack had been everything Ed wasn't; he was athletic and muscular when Ed was gangly and thin, he was cool when Ed was an awkward nerd. He'd had bitter evidence of Jack's easy popularity girls while he just was starting steal anxious glances in their direction: in one particular case, he'd been summoning up the courage to tell a girl in his science study group that he had a crush on her when she had revealed she was Jack's girlfriend du jour. Of course their schoolyard romance had inevitably unravelled quickly, but by that time the semester had changed and Ed never had an excuse to hang out with her again.

For the most part, Jack hadn't been particularly cruel to Ed, but one event from his final year stood out in his memory. His most vulnerable and hated moments at school were in the gym changing rooms: still awkward and embarrassed about his body, Ed tried to spend as little time there as possible, and always as close to alone as he could manage. On this occasion he had catastrophically failed: after a swimming period, while carefully trying to change back into his underwear while keeping a towel firmly wrapped around his hips, a few jocks from the hockey team barreled loudly through the changing rooms on their way to the pitch. They mostly ignored everyone around them in favour of their own noisy banter, but trailing at the end of the group came Jack.

Jack shouldn't even have been there; he had graduated the previous year and was already at college, but for some reason still trained with the school team now and then. Seeing Ed distracted by the other players, he deliberately shouldered into him from behind as he passed. This was probably not out of spite; it was common enough physical horseplay between guys at their school, but it spun him fully around and knocked his grip on his towel. By this time only Ed and Jack were left in the changing room, and Jack didn't stop walking as he glanced back over his shoulder, but it was too late for Ed to cover himself. The way Jack grinned at the sight of him, fully naked, was ingrained on Ed forever. "Faggot," was all he said, dropping the slur with casual indifference. And then he was gone.

With a tremendous force of will he tore his eyes away from his neighbour and turned back to face the bar. He took a deep breath and tried to compose himself. The liquid fizzed and shivered in it's glass, proof of the unsteadiness of his hand as he took a large mouthful of his drink. He allowed himself another surreptitious glance back over at Jack. The other man hadn't noticed him or his reaction, and seemed deep in contemplation of his own bottle. His phone flashed and he snatched it up, desperate for word from Jessie, to hear that she was going to be here soon.

"Hey babe!" the message read. "Remember that thing I said you should try yesterday? I've got a surprise for you. You're going to love it."

- o -

He had been sitting naked in her bathroom, skin red and tender from the waxing, while she stood, fully clothed, leaning against the door and watching him. She'd been right about this part at least, it had been super hot. Despite the pain, he'd gotten really hard during the process. Not just from the stripping itself, but the way she paid such close attention to his body, caressing and examining each newly revealed patch of skin to test it's smooth hairlessness. Of course his body had responded, and there had been nothing he could do to hide his insistent erection, but she didn't acknowledge it until she had finished. Then she looked down at him with a wry smile, and told him he should jerk off. That was hot too, maintaining eye contact with her as she patiently watched him, arms folded, stroking his shaft. It didn't take long, with his skin alive and singing from the waxing.

"I'm close," he panted. He had hoped she might join in for the ending, to take his load in her mouth the way she sometimes did if he had made her come just right when he went down on her. But she stayed where she was.

"Catch it in your hand," she instructed calmly, the hint of a smile on her face.

As if on command, he felt the pulsing of his orgasm start just as she spoke, and put his hand in place just in time to catch it; three big spurts, and then the oozing remains. By instinct, he ran his other hand up the underside of his cock, squeezing the last drops out.

For a long moment he just sat there in stillness, aware of all the sweet smells of her expensive toiletries, and that puddle of white liquid in his hand.

"Have you ever tasted your own cum?" she asked at last, her eyes glittering with excitement, although her expression remained calm and serious.

He nodded silently.

"I want you to eat that. Now."

He blinked for a moment. He looked down at his hand and back up at her. She raised an eyebrow expectantly. He slowly lifted his hand to his mouth, first cupping it so that the liquid flowed into his mouth, and then running his tongue across his palm to collect the thicker fraction. He had to lick his hand a few more times to gather it all; at the end it was hard to tell what was cum and what was saliva. He held up an empty palm to show her, and swallowed ostentatiously. She lifted her head slightly with a skeptical air. He obediently opened his mouth to show her it was empty.

Her mouth split into a wide grin. "That was so hot," she murmured, as both justification and reward. "Hey, you know what," she added airily, as if she had just thought of it. "You should try sucking cock some time. I think you'd be really good at it." She chewed her lip thoughtfully. "Yeah, I'd really like to see that." She turned, unlatching the bathroom door, and stepped out into the next room. "Clean yourself up babe, I need to show you how to wear a gaff," she called over her shoulder. He stared after her, dazed.

- o -

He stared down at his phone, dazed. He had a dizzy, tingling feeling spreading across his scalp, already uncomfortable from his wig, as the situation slowly dawned on him. She wasn't coming. She had set him up, and it wasn't to have him cling to her arm while they drank the evening away together. He took another mouthful of his drink.

A flash of light caught his attention out of the corner of his eye; the black glass of a phone screen lighting up along the bar. Jack's hand lazily picked it up, flicking through the lock screen. Ed was paralysed, unable to take a breath in the long moments as the other man processed the message, and then slowly, inevitably, turned to look at him. Their eyes met. His face split into a leering grin that seemed alarmingly familiar. He leaned over the empty barstools that separated them, close enough to offer a conspiratorial whisper.

"Are you..." he pointed at the screen of his phone, as if Ed could see the message. He had a sinking feeling he knew what it said. "Are you Jessies, uh..." he paused significantly. "...Partner?"

Ed wasn't able to do anything other than nod slowly. His eyes were wide and round like moons. He clutched his phone nervously to his lap.

Jack chuckled quietly. "Yeah, she was right," he said after a moment. "You definitely do make a cute girlie girl, don't you."

Ed tried to swallow, but his throat seemed to have locked closed. Desperate for some distraction from Jack's hungry stare, he took another gulp of his drink, finishing it. He regretted the gesture; he felt no less tense and holding the glass simply reminded him of how much his hand was trembling. He allowed his eyes to flicker back to Jack, who was still regarding him with a calm, cat-like grin.

"Okay, sure," he continued, as if responding to an unspoken request. "I think we can help each other out." He slipped off his stool and moved up to the one next to Ed, facing the bar and leaning sideways to speak. "Head for the bathrooms, but keep going. Take a left, and up a short flight of stairs, and there's a store room on your right. I'll be right behind you."

For a long moment, Ed didn't move. He didn't know what to do. Jack's change in position spared from having to maintain eye contact, and he stared down at his lap. His phone lit up between his clasped hands; he didn't even have to unlock it to see the preview of Jessie's message.

"Babe, this is going to be so hot."

He blanked the screen with a gesture. Slowly and deliberately, he turned away from Jack and slipped off the stool. He wobbled slightly on the heels as he picked his way carefully towards the bathrooms at the end of the bar. It might have been the gin having an unusually swift effect, but he felt like he was buzzing with nervous energy.

He turned with relief into the back corridor, out of sight of the bar, and gratefully free from the electric tingle of public attention, as well as Jack's hungry eyes. A wave of coldness came over him. He had the sudden urge to escape. He considered for a moment if there might be a back exit down the corridor, but he didn't think so; he could see the start of the narrow stairs further down, seeming to lead deeper into the building.

A new idea occurred to him, like a gasp of fresh air: perhaps he could hide in a bathroom stall, and lock the door. Then he could text Jessie, tell her he wasn't going to do it. Get her to call Jack off. Then tell her to come and find him, and when it was safe, they'd leave together and go home. That was a plan. It was a great plan. It meant he didn't have to face Jack, he didn't have to suck a cock, he didn't even have to walk across the bar on his own again. The nightmare would be over. That's what he would do.

He pushed the bathroom door open a crack, and stopped. He was at the men's bathroom. He stared at his own hand splayed against the door to push it, tipped with long royal blue nails, carefully selected to match his dress. He hesitated. He had walked past the ladies bathroom. He glanced back. It was only a few steps behind. Which should he use to hide, dressed as he was? Either would have stalls to hide in. He was just a few paces away from safety, but if someone saw him in the men's room...

He was startled by a movement inside the bathroom: someone inside was about to come out. The fear of being caught loitering outside the toilets rose to a moment of panic; he released the door with a start and hurried up the corridor, and was around the corner and had vaulted up the steps before he had time to think. It was only when he reached the door to the store room that he realised his mistake.

He stood frozen for a moment, unsure whether to try and hurry back down the stairs and try to slip into the ladies' room before Jack came. He looked dubiously further up the corridor, which seemed to be blocked by boxes and dusty equipment. He unlocked his phone. His thumb hovered over the text box, desperate to send a message to Jessie, a plea for help, but at a complete loss for what to say.

"Babe, this is going to be so hot."

He could hear her saying that last message out loud, as clearly as if she was in the room with him. Thoughts of her came into his mind unasked for. Thoughts of her body, of every curve and fold; of her dark nipples beneath his fingers, and the feeling of burying his face between her legs. Over it all, he thought about how much he loved to hear her moan with pleasure, how much he loved doing everything he could to turn her on, to amp her up until she was shuddering with desire, whispering in his ear: yes, yes, yes! How was he going to reply to that?

He jumped when Jack laid his hand gently on his shoulder.

"Hey," the other man said softly. His voice had taken on a friendly, amicable tone. "It's okay, it's just me."

Ed still recoiled reflexively, and took a step back from him. He looked down at the ground, awkwardly.

"Having second thoughts?" he asked, still using the same reassuring tone. "Hey, that's okay, no one's going to make you do anything you don't want to." He reached out a hand to touch his cheek, his firm masculine fingers brushing past a curl of fake blonde hair to contact Ed's skin. "I bet this is all pretty confusing to you right now, huh."

Ed was shaking like a leaf, but couldn't deny how much that firm hand and warm voice soothed him. He didn't pull away from the touch; instead, he tilted his head ever so slightly, accepting the gesture.

"I know, right now you're feeling like she's swept you up, and dressed you up like a doll. Made you all pretty. And damn if she hasn't done a good job." Jack bit his lip for a moment before continuing. "And now she's asked you to do some stuff. Stuff that makes you uncomfortable." He lifted Ed's chin with his hand, so their eyes met. As it touched his face, Ed could smell his hand, the scent of stale beer and a hint of nicotine. They were so different from Jessie's soft, gently perfumed fingers, but also different from his own; thick and coarse, but strong. "Or maybe," he continued, his voice barely more than a murmur, "stuff you think should make you uncomfortable."

Ed blinked slowly up at him as the words sank in. His expression was warm and friendly, but something in those eyes was still hard and piercing. He seemed to be seeing deep into Ed's soul.

"You know, you can't just put a boy in a dress and a wig and make him a sissy. There's got to be something inside him that makes it right. Makes it fit."

From it's position on his jaw, it was a short, deft movement for Jack's thumb to cross over Ed's mouth. It peeled forward his lower lip, waxy with gloss. His jaw dropped compliantly, allowing the thumb to make contact with the tip of Ed's tongue. His mouth came alive with the sudden new sensation, watering uncontrollably with expectation.

"The world has tried to beat it out of you, but you don't have to play that game," he continued. "So if you want to, you can leave right now." He gestured with his free hand. "Walk out the door, I won't stop you. Jessie sure won't stop you." Jack's grip on Ed's jaw tightened slightly, his thumb pushing a fraction further into Ed's mouth. His voice dropped an octave, becoming hard and forceful. "Or you can get on your knees, and do what you were made to do."

It seemed the most natural thing in the world for Ed to sink down onto his knees, the hem of the blue dress riding up his thighs as he dropped. Jack's hand stayed by his face for part of the journey, but halfway down he pulled it back, taking a line of saliva from Ed's open mouth, using the wet thumb to unfasten his fly. In a single deft movement, Jack's cock was freed of it's captivity. Ed's eyes widened; he had seen other men's penises in porn before, but it was different to see one up close, alarming and arousing at the same time. He noted all the ways it was different from his own; longer, thicker, the skin tone slightly darker. It was starting to stiffen with it's own anticipation, the foreskin pulling back from it's pink tip.

A last quiver of indecision overtook him. He was aware of an urge to turn away, to get up and leave, but it felt distant and muted, as if it was happening to someone else. He looked up. His eyebrows rose in surprise and alarm to see that Jack was holding his phone, recording.