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Edward knew it was bad when jerking off started to get boring.
Even before he was the Riddler, he hadn’t exactly been a ladies man, and now with a vastly more complex nightlife, his opportunities were becoming increasingly slim.
To make a long, but uncomplicated, story short; he was a virgin.
He’d taken to his own hand long ago, like most growing boys do, and hadn’t ventured past it. He was positively aching for touch. He shamefully eyed women on the street, shyly glancing, just long enough to imagine what they looked underneath their clothes.
Not that he really knew what to imagine.
Sure, he’d watched porn before, but the gawdy, ridiculous moans turned him off, and he had a nagging suspicion that the average woman’s body probably didn’t look like that. All sharp curves and body oil; No, he wanted something less artificial.
It was a typical Gotham night; cloudy, humid, yet cold, like the sky was teasing the idea of rain. Edward had his eyes closed, trying to conjure a vague idea of an ideal woman in his mind, with one fist wrapped tightly around his cock.
But something just didn’t feel right. He was aching to come, rutting sharply into his hand, desperately searching for release, but as hard as he got, it just wasn’t working.
He ran his free hand up and down his side, over his thighs, but it didn’t feel like the real thing. He was achingly hard, tip red and slick with precum, and thrusting into his hand with reckless abandon until he was physically panting, sweating from the exertion, small whimpers leaking from his lips.
It felt like it went on forever, but nothing would help, nothing would do it for him.
After god-knows how long, Edward was about to give up and surrender to a fitful sleep, and try again the next night. But, then again, he was going to be quite busy tomorrow night. He was picking up rats from the pet store, and new piping from the supply shop. To stay on his desired schedule he’d need to be productive, and with the way his head was swimming now, there’s no way he’d be focused enough with aching balls.
He weighed his options.
1) Call someone he knows that might have sex with him (Not possible, due to his lack of friends). 2) Go out to a bar and try and pick someone up (Also not possible, due to his lack of social skills and sex appeal). 3) Find a whore.
Despite his recent expenditures at the army supply store and Home Depot, Edward could say that he had some spending money on hand. Working in tech had worked in his advantage in a multitude of ways. The real problem was the internal struggle. Could he overcome his twisted sense of morality, and indulge in such a filthy, criminal act?
His erection twitched in his fist at the thought. Okay, yes, he could.
“They’re just supporting themselves,” He muttered to himself as he took to the streets. He already lived in the part of town that most people tried to avoid. He was sure one of these street corners would be populated by a lady of the night, especially as he inched closer to the Iceberg Lounge. “Just making a living in the… corrupt system that infests the inner workings of-”
“Looking for a good time, sweetheart?”
A young woman, scantily clad in a tight black dress, was looking at him expectantly. She was gorgeous, he thought silently.
“How-” He cleared his throat before speaking again, quieter this time. “How much?”
The woman smiled, almost smugly.
“Depends on what you’re asking for, doll.” She took a step closer to him, and he averted his eyes, simply out of habit. “Hand, mouth, or all the way ?” Edward’s heart was beating fast in his chest, and he forced himself to bring his gaze from the pavement into the woman’s eyes.
“All the way.”
“Seventy bucks. Thirty bucks extra, if you want to cuddle afterwards.” He’d never solicited a prostitute before, but it seemed pricey. Was she scamming him, or was he just cheap?
“That sounds-”
“Expensive?” He hated when she interrupted him, but said nothing of it. “I’m high end, baby. If you wanna find something cheaper, you’ll have to keep walking. I come with the no-STD-guarantee.” She smiled coyly.
He hadn’t even thought about it. Though he really had no reason to trust her word, he could feel his dick pressing against his boxers, and he was ready to throw caution to the wind.
“Okay.” He sighed, digging for his wallet, before fishing out a wrinkled hundred dollar bill, slipping it into her hand. When her cold skin touched his, just briefly, he felt the foreign excitement of human contact. “Your place or mine?” The question sounded silly, but he wasn’t exactly practiced at this, or anything.
“I know a place.”
She led him down the block, until they reached a tall, dark brick building. She took his hand, absentmindedly, showing him down the alley, and a steel door entrance to the building. A man stood at the door, arms crossed, like a bouncer.
“He’s with me.” She whispered to him, and Edward was whisked inside. They climbed a rickety staircase, up to a room, which, when the door opened, reminded Eddie where he really was.
The dark burgundy and sultry red interior was a little too brothel-like for his taste. Though, to be fair, that’s what it was. The single bed in the room was covered in a plush comforter, and was pristinely made. Edward took an awed look around, taking in the colored wallpaper, and dim orange lighting. When he refocused, the woman was on the bed, gently undoing the straps of her heels. He felt suddenly inadequate, as if this was a woman he had picked up, not paid to sleep with him.
“What do I-” The question died on his lips. He could at least act like he knew what he was doing. To her credit, the woman was doing her best to look unsympathetic.
“Come here, sweetheart, tell me about yourself.” Edward sat on the bed, undoing his own boots, as the woman stroked circles on his back through his shirt, before pushing into the knots on his back. “Your job must be stressful, yeah? You’re so tense, baby.”
His mouth was wide in pleasure, not just from the relieving massage, but from her words. When was the last time someone had talked to him with such affection? After some thought he realized, never had anyone talked to him with such care in their tone.
“Mmm, yeah you could say that.” He mumbled.
“What do you do for work?” Edward laughed, awkwardly, even though she didn’t understand the joke.
“Tech stuff, mostly.” Understatement of the year.
“That’s cool!” Something tugged in his chest. She sounded so genuine. Perhaps it was her job to sound genuine. He didn’t mind, he liked it either way. “So what kinda stuff are you into?”
Edward choked on his own spit at the change of topic, though really he should’ve expected it. If he wanted to pay someone to talk to him, he’d get a therapist, not a prostitute.
“I- um, I… I don’t really know, for sure.” He felt his cheeks getting hot, blood rushing to them.
“Are you a virgin?”
He could say no. He could deny, deny, deny. He could suck it up, accept his hundred dollar loss, and sprint for the door. He didn’t do any of these things.
“Yes.”
“That’s so exciting!” The woman, to Edward’s surprise, grinned widely. “I get to be your first, wow that makes me feel so special.” She sighed, almost dreamily. “If you’d have told me that, maybe I would’ve given you a discount.” She joked.
Before Edward could choke out a reply, her hand appeared on his thigh. Tracing the inner seam with her long nails. His attention was suddenly refocused on his hard-on, which, if it had diminished at all, had now returned full force. He had to focus on keeping his hips planted on the bed. Her fingers traced slowly upward, until he could feel their gentle touch ghosting over the bulge in his pants.
“This is how I usually start, to get somebody in the mood.” She then presses her palm into him, and the pressure makes Edward jump. This is completely different than his own hand, like he doesn’t know what’s coming next, or what to expect. “What’s your name?” The question catches him off guard.
“Edward… Or Eddie.”
“Do you want to see my body, Eddie?”
Hearing his name from her lips made his hips jerk into her hand. Now he didn’t have to imagine what she looked like in shy glances, like he did with women on the street, no, she was going to show him.
“Mmm- Yes, yes, please.”
“Well, because you’re so polite.”
She rose from the bed, though Edward sorely missed her touch, he was too distracted by her figure to care too much about it. Slowly, she peeled the thin black fabric from her frame, dragging it over every inch of her curves, teasingly. It made Edward want to rip it off her. First, it revealed a black lacy bra, with so little coverage it could hardly be called that. As it fell, finally, from her hips to the floor, a pair of matching black cotton panties were revealed.
Every inch of her skin, revealed to him, was intoxicating. He wanted to touch her, to kiss and lick anywhere he could.
“Then, because it’s your very first time, I’ll throw in something extra for you.”
She dropped to her knees in front of him. Edward’s eyes fall instinctively to her cleavage, and then to her pursed lips. He practically jumped out of his skin when she pressed her mouth to his bulge, over his pants. He could feel the hot breath from her mouth through the fabric, a small patch of saliva staining the fly.
Her fingers slowly undid the zipper, and Edward lifted his hips, allowing her to drag his pants down his legs, along with his boxers, before discarding them. His cock was released from its confines, exposed to the night air. Without a second though, she wrapped a hand around it, pulling in swirling circular motions up and down its length.
“Oh, oh-” He couldn’t suppress the noises, the whines, escaping from his throat. “That feels, mmm, that feels so good.”
She didn’t respond, she simply smiled smugly to herself, before leaning forward without warning, wrapping her lips around his tip. He could feel the warmth of her mouth, her tongue licking patterns around the head. It was almost too much, and he tried desperately to keep himself from coming too soon.
His hands thread themselves into her hair, gripping tightly, though he restrained himself from pushing her head. He only needed something to grab to steady himself. He could hear the wet sounds from her throat, and felt the beads of saliva dripping down his length.
His hips bucked of their own accord, pushing themselves into her mouth, stuttering unconfidently.
“I’m, oh fuck, that feels so- I think I’m-”
She pulls off him abruptly, leaving him bucking into the air, chasing after an orgasm that won’t come.
“I’m sorry, baby,” She looks at him apologetically, after seeing his confused expression. “But if you want to fuck me tonight,” He does. “Then you have to hold off a bit longer.” He silently swore to hold off forever, if he had to.
“I want to touch you.” The words tumbled from his mouth without any second of forethought. His mind was so scrambled, so desperate, that he found no filter between his thoughts and his words.
“You can do that.” She climbed back onto the bed, moving herself to lean against the pillows, stacked at the top of the bed. She lay back lazily, running his fingers up and down her sides, his eyes mindlessly following their path. “Where do you want to touch?”
He reached out, but she caught his wrist before he could find contact.
“Use your words, sweetheart.”
His cheeks flushed, though his eyes couldn’t break from her body.
“I- I want to touch…” He didn’t know how to phrase it. “I want to touch your tits.” It sounded so vulgar, he wanted to wash his mouth out. But he quickly forgot the thought when her grip on her wrist pulled his hand toward her chest, letting him grab her. As he felt the weight of her in his hand, the soft warm feeling, she spoke again.
“See? Polite boys always get what they ask for.”
He whined, without his mind’s consent. He quickly shut his mouth, pressing his lips together tightly, in shame.
“Such a pretty boy,” She stroked the hair from his face, tracing the lines of his cheek. “I love when you make noises like that, so sweet.” There she was, sounding so genuine again. The praise made a blush climb up his neck. His free hand moved to his cock, taking it in his fist roughly, replaying the words in his head.
“Mm, thank you, thank you,” He mumbled, watching her face twist into a pleased expression.
Her hands toyed with the hem at the bottom of his shirt. It was starting to suffocate him, the collar feeling like it was closing around his neck. Without protest, he let her drag it up and over his head, before he discarded it on the floor, with the rest of his clothes. She looked him up and down, and he couldn’t find it in himself to doubt the look of lust in her eyes.
“Does this pretty boy want to fuck me?” She asked, looking into his eyes intently.
“Yes!” His pupils are wide, even at the thought. “I want to fuck you so bad, I need it, I-”
“What do polite boys say?”
He paused, trying to calm his breathing and erratic heart.
“Please?” She nodded, waiting for more. “Please. Please let me fuck you, I- I would do anything, please-”
He was caught off guard by her hand on him suddenly, trailing from his collarbone, down the front of his chest, past his belly button, through the trail of hair leading down to the base of his dick, until she finally took him in her hand.
He was achingly hard. He’d been at the edge of coming all night, and he was becoming more and more frantic, chasing his release fruitlessly. He’s offhandedly aware of her reaching for something on the nightstand, before he sees her rip open a metallic package, transferring it to her other hand.
A condom. He supposes this was part of the guarantee she’d promised earlier. He silently lets her roll the rubber up his length.
Edward puts his hands on either side of her head, moving up on the bed until he’s lined up at her entrance, and she guides the tip of his cock up and down her slit.
“Do you feel how wet I am, sweetheart?” She asks, tracing shaping on his back with her nails. “That’s all for you.” He wanted her more than ever. “Go ahead, baby.”
With that simple permission, he pushed himself inside her, slowly at first (which was more for him than her), until he was nearly entirely sheathed in her.
It was better than he’d imagined, which is saying something, because he’d imagined it probably a million times.
“How does it feel?” She asks, prompting Edward from his trance.
“It, fuck, it feels so good, you feel so good,” His head hangs limply down. “I can’t- It’s so perfect.”
“Try moving,” Edward pulls out slightly, and then pushes back in, still slow and steady. “Again.” Her breath is becoming slightly labored, and she bites her lower lip. “Again.” He pulls out again, until he’s nearly completely out, and pushes back in. “Just like that, baby, just like that.”
Without warning, he’s starting to thrust. This time, without any hesitancy. He’s chasing his orgasm, the pleasure nearly clouding his vision. He can feel her squeezing him, and he’s almost aware of the breathy moans escaping his throat.
The bed shakes beneath them as he thrusts, rutting sharply into her, their hips meeting in a lewd slapping noise that echoes into the hot room. He’s whining now, sweet noises falling from his lips.
“You’re being so good for me,” She’s panting under him, her nails digging sharply into his back, until Edward is sure she’s drawn blood. “Such a good boy, you’re so perfect.”
“Say it again,” He pants out. “ Please .”
“You like being called a good boy?” He nods fervently. “You’re so pretty, so lovely. I love when you fuck me like this, it’s- Mmm fuck- it’s so good, Eddie.”
He drops to his elbows, and she arches her back sharply, so their chests are flush to each other, faces just inches apart. She keens, moving her lips to Edward’s neck, sucking marks down his throat, sure to show up deep purple tomorrow.
He can hear the bed pounding against the wall, and he secretly hopes it leaves a dent. She locks her legs around his waist, pulling him ever closer to her. One of her hands goes to his hair, twisting the strands into a tight grip, until it’s tugging roughly at his scalp. The pain is violently unexpected, and it sends a bolt of electricity through his body, straight to his cock.
She feels his hips stutter at the action, and tugs again sharply. His hips jerk unevenly, and a high whine drips from his lips.
“Do it again, please,” He whimpers, trying to decipher the hazy look on her features.
She pulls at his hair again sharply, this time roughly pulling his head to the side, exposing the side of his neck, kissing down his throat, before biting down.
The pointed sting of her teeth are like a shot of adrenaline. He’s sent into a new frenzy throwing his hips into her at a new pace.
“I’m going, mmph, I’m going to come.” He admits, as soon as he realizes it himself. He can feel his balls tightening, and he’s so, so, painfully close to the edge.
“I want you to come for me, can you do that?” He nods, his breath too labored to speak again. “Come for me baby,” He buries his face into the crook of her shoulder rutting into her. “Be a good boy, and come.”
At her command, he comes. His hips stutter, before slowing, and finally burying himself deep inside of her, to the hilt, until he can feel his own warm seed fill the condom, and drip down his length.
He falls off of her, or more so collapses, in order to take it off, though still he sorely misses the warmth. He ties it in a knot, discarding it to the wastebin in the corner of the room.
When he comes back, she’s sitting up on her elbows, and he feels strangely exposed, naked in front of her gaze. He remembers the extra thirty dollars he paid her, to afford the luxury of a more platonic touch.
“Come here, baby,” She gestures for him to get back on the bed. He obliges, crawling toward her. When he lay next to her, she pulled him over, until his cheek rested on her bare chest, her heartbeat pounding in his ear, the rush of her blood filling his head. “How do you feel?”
“Like this is the place worthy of salvation in the cesspool that is Gotham City.” The endorphins flowing through his bloodstream had loosened his lips.
“Well, I’m glad it was good, sweetheart.” She says, though it feels like she doesn’t entirely disagree with his statement.
When he wakes up, she’s gone, and he’s alone in the dark room. There’s a note left on his pile of clothes, pushed into a heap on the ground.
I hope you had a good first time, pretty boy xoxo
P.S. If you ever want to do it again, call me?
P.S.S. No discounts for your second time <3