“It’s been over a year!” Emma said, she sounded exasperated.
Jessica’s friend sat cross-legged on the couch across from her. As always, she was interrogating her about her love-life.
“A year isn’t that long.” Jessica replied. She didn’t mind Emma’s meddling, she was her best-friend after all and she only wanted to help. Besides, part of her agreed that it was time for her to move on.
“A year without sex is pretty long, Jess.” Her friend replied.
Emma blushed slightly, why did it always have to be about sex? But she responded bravely. “Who says I haven’t had sex since I broke up with John?”
“Playing with yourself doesn’t count, Jess.” Her friend replied without missing a beat.
Jessica’s blush deepened, her friend knew her too well. “I could’ve met someone…” She countered.
“You? Hook up with someone just for fun?” Emma replied, raising her eyebrow. “Or do you have a new crush that you’ve been keeping a secret?”
Jessica shook her head. “No, no secrets.”
“And no one-night stands either, I bet.” Emma continued.
Jessica looked away from her friend. “You know I wouldn’t do anything like that.”
Emma laughed. “No, but it wouldn’t be such a bad idea.”
Jessica’s head swiveled back to her friend in surprise. “What wouldn’t be?”
Her friend grinned. “You, hooking up with someone just for fun.”
Jessica’s blush returned. “Why would that be a good idea?”
Emma shrugged. “Get past this dry spell of yours. It might help you forget about that man who dumped you. Get you back into the game.”
Jessica shook her head. “I’ve already forgotten him.”
“Then why haven’t you been on a single date this past year?” Her friend countered.
Jessica bit her lip, unsure what to answer.
“But hey, if you’ve forgotten about him, that’s great.” Emma continued. “Then it shouldn’t be a problem for you to meet-up with some guy and enjoy yourself for a bit.”
Jessica licked her lips and looked up at her friend. Part of her wanted to agree with Emma, to do what she proposed. Though the idea made her nervous. “Why are you so interested in me having sex?” She asked her, trying to deflect the subject.
“I just want my friend to be able to have some fun.” Emma replied. “To loosen up a bit and get on with her life.”
Jessica blushed. “But how would I even meet someone for that?”
Emma grinned broadly, feeling that she was winning this argument. “There’s plenty of websites and apps that can help you with that.” She replied. “Just download an app, make a profile, post some pictures and you’ll have men for the picking.”
Jessica smiled shyly. “Would you help me with that?”
“Of course!” Emma laughed.
The next hour or so, the two friends spent taking pictures and writing the perfect profile description for Jessica.
“Now promise me.” Emma said when they were done. “Go and select any guy that looks hot. Don’t bother reading their profile, just skim it if you have to. You’re not looking for a relationship, just some fun for one night.”
Jessica blushed. “Really?”
Emma nodded. “Yes! Once you’ve wet your appetite and gained back some of your confidence, you can go ahead and look for something more serious.”
Jessica nodded. “Alright, if you say so…”
It had been a week since Jessica and her friend had created her profile. Emma had been right, she did have men for the picking. She’d skimmed the profiles of any that contacted her, staring at their pictures and imagining herself being intimate with them. The visions she got always made her blush and she quickly ignored their messages.
Emma would be disappointed with her if she knew how many men she’d turned down just because she was too nervous. But she’d never need to know, because Jessica actually had a date tonight.
There was one guy, Enrico, whose messages Jessica hadn’t ignored. He was handsome, strong, muscular, with dark hair and tanned skin. It was his smile however that made her trust him, for some reason she couldn’t explain.
She was meeting with Enrico at a bar tonight, and if all went well invite him home with her. Jessica had been honest with him, telling him that she wasn’t looking for a relationship. Enrico had eagerly agreed that he was up for a casual hookup, no strings attached.
Nervously Jessica waited for him at the bar that night, until she recognized the man from his pictures enter. She waved at him and Enrico joined her at her table with that beautiful smile of his.
“Hi.” Jessica greeted him, blushing slightly.
“Good evening, Jessica.” Enrico replied as he took the chair opposite to hers.
“I hope you don’t mind, I already ordered myself a drink.” Jessica said. The glass of white wine in front of her was half empty. She didn’t want to get herself drunk tonight, but a bit of liquid courage was certainly welcome.
“Not at all.” Enrico replied. “I’ll get something for myself when the waitress notices us.”
Jessica nodded, not sure what to say next.
Enrico looked down at the menu in front of him and then back at her, licking his lips for a moment. It occurred to Jessica that he seemed slightly nervous himself.
The silence stretched, slowly becoming uncomfortable as neither of them said a word.
“I guess I should’ve thought of some conversation topic, before coming.” Jessica chuckled.
Enrico grinned. “Yeah me too…” He paused for a moment.
“So do you do this often?” He asked. “If you don’t mind me asking.”
“No, not at all.” Jessica quickly replied.
Enrico smiled. “Me neither.” He replied. “First time actually… I mean my first time hooking up with someone like this… not my first time, you know…”
Jessica smiled, his slight awkwardness somehow made her feel more at ease. “Me too.” She replied.
Enrico grinned. “So neither of us know what we’re supposed to be doing right now.”
Jessica matched his grin, comfortable now in their shared anxiety. “I suppose we should be flirting a bit, whilst getting to know each-other.”
Enrico nodded. “Alright, what would you like to know about me?”
Jessica shrugged. “I don’t know. What’s your favorite color?”
“Red.” Enrico replied. “What’s yours?”
“Green.” Jessica said.
A short silence followed and Jessica giggled. “Guess we’re not very practiced at flirting yet.”
Enrico took a deep breath. “Do you want to know why red is my favorite color?” He asked.
Jessica nodded.
Enrico bent over the table slightly, bringing his face closer to hers. “It’s the color of a woman’s lips, soft and beautiful, ready to be kissed. Like yours, with that tinge of red lipstick, plump and inviting.”
Jessica felt a blush creeping on her cheeks, her heart suddenly beating faster.
“It’s also the color of her cheeks.” Enrico continued. “When she gets a compliment, like yours right now.”
Jessica’s blush deepened. “I thought you weren’t very good at this.”
Enrico shrugged. “I guess I never tried.” He replied.
Jessica licked her lips. “What else? Why else is red your favorite color?”
Her date grinned. “I have two more reasons, but first tell me why you like green?”
Jessica thought about it for a moment, trying to make her reasoning sound as flirty at his, yet it just seemed boring instead. “I like nature.” She replied. “Going out on long walks in the forest, getting lost in the woods. It’s the color of nature.”
Enrico nodded. “My other reasons are a bit more naughty, do you want to hear them?”
Jessica nodded, slightly excited to hear what he might tell her.
“Red is also the color,” Enrico continued, “of a woman’s bottom when she’s misbehaved, or her knees when she’s been a very good girl.”
Jessica’s blush immediately returned, her mind flailing to understand what he meant, though she knew there was only one real explanation.
“Too naughty?” Enrico asked when she wasn’t able to respond.
Jessica shook her head. “No, no, you just caught me off guard.” She laughed.
Enrico grinned and Jessica could see that despite his flirting words he was still as nervous as she was. It made her feel confident, and brave. “You know,” she said, “my love for green might be a bit more naughty than it appears at first as well.”
Enrico’s eyes widened. “Please, do tell.”
Jessica blushed, biting her lips. “During most of these hikes through nature I’ve been alone, but I’ve always wished to be accompanied by a man. Someone who deep in the forest where no-one could see us would strip me naked, push me up against some tree and fuck me in the middle of the woods.”
Enrico smiled broadly. “Like some forest-nymph with greenery surrounding her.”
Jessica laughed and nodded. She’d never told anyone this, yet her heart was racing, her blood gushing through her veins. Perhaps Emma had been right, being with someone just for fun, made it easier to share these things and enjoy yourself, knowing there would be no consequences.
“You’re not bad at this flirting thing yourself.” Enrico then said with a smile. “I almost wish we had time to go hiking today.”
Jessica blushed. “Well then I wish I’d been naughty, so that I could show you those other shades of red you enjoy later tonight.”
Enrico grinned. “Good girls can get spankings too, young lady.” He replied.
Jessica bit her lip. “That doesn’t seem fair.” She replied.
“But it is.” Enrico replied. “It wouldn’t be fair if bad girls had all the fun, would it?”
Jessica giggled. “I guess not.”
“Besides,” he continued, “when a good girl gets spanked, it tends to be a lot more… let’s say enjoyable.”
Jessica blushed. “Well in that case… Do you want to come over and show me those other shades of red you like?”
“I’d love to.” Enrico replied.
Nervously, Jessica entered her apartment, with Enrico right behind her. She jumped slightly when he closed the door and then quickly turned around to face him. For a moment they just stared at each-other, Jessica biting her lip. Then she reached out and took his hand, placing it on her chest, she could feel her own heart-beat underneath.
Enrico let his hand glide up to her neck and the back of her neck, using it to pull her in closer and kiss her.
Hungrily Jessica stepped forward, pushing her body against his, wrapping her arms around him as they kissed. Eagerly she fumbled at his clothing, pulling his shirt over his head, unbuckling his jeans, and at the same time Enrico pulled off her dress, fumbling with her bra until they embraced bare chest against chest, with just his boxers and her own panties left between them.
Jessica could feel his hard cock trapped against her, she reached down into Enrico’s boxers to free him, but he grabbed her wrists to stop her. “Not yet.” He said. “Or have you changed your mind about showing me my favorite shades of red?”
Jessica blushed. “No, I haven’t.” She replied.
Enrico grinned and took her wrist, guiding her further into her apartment.
Blushingly, Jessica let him guide her across his lap as he sat down on her couch. Slowly he pulled down her panties, baring her backside completely. She could feel his hand on her bottom, warm, strong, kneading and caressing.
She moaned softly at the intimate touch, spreading her legs slightly, showing him that she was wet and horny. Enrico’s hand slid down, cupping her pussy, two fingers sliding between her lips before pulling back his hand.
Jessica moaned deeply and then her date raised his arm. He slapped her ass firmly, a warm sting spreading across her skin from the impact. She closed her eyes.
Enrico raised his arm again, two, three more times his hand connected with her backside. It didn’t hurt, but her skin tingled and burned, like when you took a shower that was just a bit too hot.
Then his hand played with her backside some more, squeezing, groping, his fingernails dragging across her skin. Jessica curved her back, pushing her bottom up, asking for more.
Once again Enrico raised his arm to spank her. A bit harder than before, the smacks echoed through her apartment, the sting spreading across her backside.
“Don’t stop.” Jessica moaned as the heat in her bottom began to build. The sting transitioned into a bit of pain, but this just turned her on even more. Enrico continued, just as she asked, his hand connecting with her backside again and again.
When Enrico paused, his fingers eagerly delved into her pussy after caressing her buttocks. Jessica could feel him inside of her, she moaned deeply, wanting more, more of this but more of the pain as well.
Her date pulled his hand back. The smacks on her bottom now hard and firm, her buttocks rippling from the impact. Jessica squealed in surprise at the force behind them and the pain that settled across her backside. Yet she did not want him to stop, equally surprised by her own arousal at this pain.
Again and again Enrico’s hand rained down on her backside as Jessica moaned and squealed. Until finally, his hand rested on her backside again, squeezing, groping. “Beautiful red.” Enrico said, as his hand slipped between her legs once more, rewarding her for her perseverance.
“Don’t stop.” Jessica moaned once more. She arched her back, raising her red bottom as Enrico pumped his fingers inside of her, begging for more.
Her date chuckled, the hand that had been resting on her lower back, holding her down firmly across his lap now slid up to her bottom. While one hand brought bliss, the other now brought pain, smacking her backside as he brought her to ecstasy.
Jessica screamed, her body shaking, her bottom burning. Out of breath she collapsed across Enrico’s lap.
“Good girl.” He said, now gently caressing her backside. “Your bottom truly does turn a beautiful shade of red.”
Jessica blushed slightly. She’d never done anything like this before, she’d known people were into this kind of thing, but it had never occurred to her how hot and sexy it could be. She’d only agreed to it because she was supposed to just have some fun, to try something new. Now she wondered why she’d never tried it before.
“Can I see?” She asked, blushing slightly, not sure how submissive she was supposed to be as she was still laying across his lap.
“Of course.” Enrico replied and he helped her up.
Jessica blushed as she looked down at her date, sitting almost naked on her couch, his boxers nearly bursting from his erection. “I’ll be right back.” She said
She ran to the bathroom, admiring her colored backside in the mirror. It was redder than she’d thought, and sensitive to her touch. It turned her on even more.
Quickly she returned to Enrico, eager to please him after what he’d done for her. “Only one shade of red left.” She whispered, blushing slightly.
Enrico grinned as she knelt down on the hard floor at his feet. “It’s not every day I get to admire all four shades at once.” He said, taking in her blush, her red lips, her sore bottom and imagining her soon to be red knees.
Jessica pulled his erection from its prison, surprised at his large size and wondering how it had fit inside those boxers. Time to earn that good girl spanking I got, she thought and then took him in her mouth.
It wasn’t long before Enrico was grunting and moaning softly as she licked, kissed and sucked his cock. Eagerly she pleasured him, looking up with big eyes, and even arching out her back to give him a good look at the red bottom he had given her.
His body began to tremble, his eyes closed as it became too much for him to bear and then with a loud grunt he came, filling her mouth with his juices. Jessica swallowed it all, licking him clean before looking up at him, smiling broadly.
When Enrico opened his eyes again, Jessica slowly stood. His eyes slid down for a moment, catching the red shade across her knees from sitting on the hard wooden floor. “Four for four.” He said.
Jessica grinned.
There was a moment of silence as she sat down beside him.
“So what now?” Enrico asked. The both of them suddenly unsure for a moment, now that their first flickering of lust had been satiated.
Jessica licked her lips, looking at the man beside her. She was satisfied, but she wouldn’t mind some more fun. “Do you want to stay the night?” She asked.
Jessica closed her eyes as she lay beside her date in her bed. She moaned softly as Enrico gently played with her breasts.
She hadn’t really thought about anything that had happened this evening, not since Enrico had closed her apartment door behind him. Now there was time to think, but she did not feel the regret or doubt she’d expected. She did not feel at all how she’d imagined she’d feel doing something like this. She just felt happy. Happy and horny as she could feel Enrico’s cock growing, pushing against her hip as he lay beside her.
“There’s condoms on the night-stand.” She whispered.
Enrico’s hand, caressing her breasts, pulling and squeezing her nipples, paused for a moment. Then he pulled back, she could hear the ripping of plastic and his low grunts as he provided them with protection.
Jessica looked over her shoulder just as he turned back to her, towering above her. Enrico placed his hands beside her head, leaning down to kiss her. His knee pressed against her thighs, forcing her legs apart and Jessica eagerly spread them for him.
She moaned deeply as he pushed his cock inside of her, he was big and hard, filling her completely.
Enrico fucked her slowly and gently, a sharp contrast to the intense spanking he’d given her before. His lips traced her neck, his tongue caressing her breasts before biting her nipples. “You know, I just realized I forgot one more shade of red.” He whispered.
Jessica groaned. “Which one?” She asked.
“The red of a mark left on a girl’s neck or breast when I bite her.” Enrico whispered.
Jessica whimpered softly, feeling his cock deep and slow inside of her. “Will you mark me?” She asked.
She squealed in surprise as Enrico’s teeth dug into the soft skin of her breasts. His lips collapsed around the flesh, sucking, pain pulsing through her flesh. She moaned deeply as the pain mixed with the pleasure of his cock deep inside of her.
Jessica looked down at her breast when he pulled back, seeing the round red mark just above her nipple for just a second before looking up at Enrico. He looked down at her hungrily, pulling in closer once more. This time he placed his mouth on hers, tongues intertwining, teeth biting her lips. He continued to fuck her, not slow and gentle like before, but fast and hard. His hips thrusting, pushing his cock deeper and deeper until her whole body was shaking and trembling.
Jessica squealed and moaned, coming loudly, orgasm taking over just before Enrico froze, pushing deep inside as he reached his own climax.
He collapsed on top of her.
“That’s five.” Jessica said.
Enrico chuckled. They’d been laying side by side for several minutes, not talking. Jessica’s words had come as a surprise.
“Any more shades of red I need to know about?” She asked.
“I don’t think so.” Enrico replied.
Another short silence followed. “Perhaps next time you can show me your favorite shades of green?”
Jessica blushed. “This was supposed to be a one-time deal.” She reminded him.
Enrico nodded. “I know. I’m sorry, I shouldn’t have said anything.”
Jessica licked her lips. “Though it wouldn’t be really fair, if you got to see your favorite colors and I didn’t get mine.”
Enrico grinned. “No, it wouldn’t.”
“One more date?” Jessica asked.
***
The end
Story inspired art
