The first in a possible future collection stories revolving around a man named Todd with sexual talent, but still an amateur to the world of online dating.
ALSO NOTE
Lines that appear as such
- Text -
Are meant to be text messages, but if that isn't clear I'll change it in the next chapter.
Enjoy!
“Well fuck you too bitch.”
Todd slammed down the cell phone onto the desk, and dove into his bed. Wanting to scream into the pillow, but failing to find any noise in his throat. He didn’t remain immobile for long before getting off of the bed and grabbing his phone and falling back onto the bed, unlocking his phone and opening up the messenger app and scrolling up in his most recent conversation. He quickly closed out of the app and switched to the app store. With almost no hesitation he downloaded and opened up the app, Tinder. For a second he laughed at the thought of maybe just giving up all together and downloading Grindr, but he wasn’t that far gone yet.
Without long, to his surprise and pleasure, he received a match of a very attractive girl local, with blonde hair, large breasts, and basically the whole package. He decided to be the gentleman and message first.
“Fucking bot,” he nearly yelled, throwing the phone at the pillow then diving into the adjacent pillow, falling asleep.
---
Later that night Todd reached for his phone after waking up to check the time. To his pleasant surprise he had forgotten that he had installed his dating app before falling asleep and discovered he had several matches, some of which appeared not to be bots.
He carefully examined each girl’s individual picture, taking into account every particularly interesting feature each girl had to offer, one of which, a shorter looking girl with short, with strands of a light brown color flashing through her long black hair, caught his interest. She didn’t appear to be in the level of a supermodel by any means, but she had a slight charm to her, a rebelliousness that he was interested. Her breasts were small, but in one of the selfies she was showing off that there is something below her neck with an exposing post workout training bra shot, another was a group of her friends with her at the pool, smiling holding various colored and sized drinks. He became extremely interested in the curves of her legs, the shape graping firmly around the front end of her bikini bottoms was, to say the least, turning him on. Her name was Emi and her bio didn’t say anything noteworthy besides the fact she was attending the local community college and that she enjoyed reading, very basic girl things. Todd went in for his first attack.
- Are you more of a Steven King kinda girl or is Fifty Shades as dark as you can go? -
This was easily Todd’s worst and best pickup line he had ever thought up, because it was, in fact, his first pickup line of all time.
He had always been with Kelly, or not been interested in girls at all because he was too young then. He had lost his virginity to her, and had discovered just that day that she had been cheating on him with various guys for her first year away at college, he cut it off then and there.
A response finally came in.
- Haha. Funny pal. Shakespeare is more my kink if that’s okay with you (; -
This was his playground, jokes are easy to play off.
- I don’t mind a girl with a little class, but maybe one with a little more of a bio would help. -
Their conversation went very back and forth from there.
- There’s a lot in it, you just have to look for it. -
- Pretty sure it only says you go to college here and you like books. -
- Alright. Now take those two and put it together with clue I gave you at the start. -
- … -
- You’re not gonna make this easy for me are you. -
- Nope! (: -
- Damn Lit Majors… -
Todd sat up in his bed. He was definitely into this girl, but it was gonna be a long day if he had any plans on ever getting a chance with the girl in his messages.
---
Not even a week later he found himself standing in front of his apartment door, opening it to find Emi, in a tight, dark blue dress, perfectly curving around her ass, and placing what she had in the front, on full display for Todd, wearing a nice dress shirt and a pair of jeans that probably didn’t go with the shirt, but he wouldn’t have known.
“You’re actually stunning.” Todd could barely get out.
Emi laughed, “You’re okay… I guess.”
Todd turned red in embarrassment, “A little too much?”
“A bit more than a little,” She grabbed his hand and pulled him out the door, “Come on didn’t you say the reservation was at 6?”
“Oh yeah, of course,” Todd led her to his car and together they sped off to a local popular italian restaurant.
---
“So you live on your own?” Emi asked as she paused from her spaghetti.
“Yeah, my parents are sorta crazy and just moved out into the woods somewhere, so they taught me how pay for everything and basically left me here to go to college while they are out in some cabin or something.”
“So... you live on your own?” This time she asked it leaving behind a wink.
“Yeah… I do.” He smiled at her then turned to the waiter, “Check please!”
---
Todd opened the door to the apartment and led Emi into it. He directed her to the couch and offered it as a place to sit. She took off her shoes and walked up to him grabbing his collar tightly, but with a hint of fire.
“I’m not really in the mood for foreplay tonight baby,” She slowly took off the first button, “If you want to fuck, I’m down to fuck, but that’s all I’m in for okay?”
Todd paused for a minute looking down at the girl he didn’t really know anything about, she went to school nearby, she worked at a small cafe her parents owned, she liked spicy foods, little things like that, and for the first time in his life he has encountered his chance at a hookup. One that he is ready and willing to take.
“Don’t worry,” He kissed her softly on the lips, “From there it’s only going up.”
As soon as he finished his sentence he once again took Emi’s mouth and placed it on his, taking his time to tenderly break into and freely explore before going and biting on her lip causing her to groan a little at the mix of pain and pleasure.
She broke off the kiss and looked up at him, “Oh yes, you’ll do fine.”
She dragged him to the open door that led into the bedroom and nearly tearing off his shirt, pushing him down on the bed, and straddling off the top him freely explored his well toned chest before quickly and flawlessly sliding out of her own dress.
Sitting on top of Todd rested, a hundred pound, 5’5, goddess in his eyes. Her small breasts still firmly filled her B-Cup sized bra, and her ass was comfortably, but in no case shying away underneath a smooth pair of dark, lacy panties.
“This feels like something right out of some Fifty Shades type stuff, are you sure you read Shakespeare?” Todd laughed at his own joke for himself as he slowly explored Emi’s body rising from her legs, to her waist, up her stomach and finally passing her breasts pulling her down into him for another kiss.
She once again pulled off and whispered into his ear, “Oh we can go such much darker than that baby don’t even worry.”
Without Todd even noticing Emi had released Todd’s button from his pants and began to slowly pull them off followed by a swift release of his underwear. Grasping his already erect cock in one hand, slowly lifting and lowering her hand on the shaft.
She smiled and spoke as her head came closer to his member’s head, “Feel free to be rough,” she kissed the tip, “It’s kinda my thing.”
With that Emi’s mouth fell into Todd’s throbbing dick swirling her tongue around the head has she did causing him to moan in pleasure which, in return, caused Emi to slightly giggle at the sound he made. In order to get back at the gesture he pulled her hair back and started to control the pace at which she sucked his cock slowly forcing her to dive deeper and deeper onto his shaft until eventually pressing all the way down, reaching the back of her throat and forcing her to come up, gasping for air. Her face was flushed has she panted, slowly stroking Todd’s member still.
She smiled, “Okay, I guess you can play along,” she squeezed his dick and quickly made a twisting motion causing him to tense up from the sudden friction.
He lifted her up and threw her onto the bed, “I can do a lot more than play princess.”
Emi shivered at that comment as Todd seamlessly unclasped her bra, giving a moment to full explore her breasts and, already erect nipples with his tongue, slightly biting the second one before pulling away from it. Then leading his head down to his prize down below, a freshly shaven, fully exposed pussy, all for him to enjoy tonight. He quickly set his mouth on the small nub at the top, taking a moment to explore it and allow time for Emi to give her own reaction, whether it be positive, or negative allowing him to move onto the next section further gaining an idea of what she did and did not enjoy.
After getting an accurate assumption he pulled up and moved over to his desk drawer where he pulled out a condom which he quickly unpacked, but with less finesse placed it on his still hard member. It had been awhile since he had actually had to use one since his previous girlfriend (he had been led to believe) had only ever been with him, the day of the breakup he had gone to get screened for STDs and, luckily, turned out clean. Nevertheless, he placed it on and went back over to the bed with her.
“Are you sure about this?” He asked hesitantly.
She laughed and kissed him, “I consent dumbass.”
Shortly following he slowly spread apart the pussy lips and slid his cock inside her. Steadily he rose the pace has he plunged deeper causing her to moan slightly, he eventually reached his full length inside her. As soon as the full reached was achieved he instantly began to slide in and out in smooth, slow strides, but not before long quickly rose the pace.
As he did he referred back to his previous self-memos about what she enjoyed the most, and went of that information as he slightly curved scraping against the right side of her inside. This caused her to, at first, scream in pleasure at the sudden change of direction and pace, Todd quickly met with a grasp of nails on his own back as she clung onto him.
She moaned, “Holy FUCK that was amazing, do that, but even harder.”
Todd had full control of the girl, “Do what even harder princess?”
Emi smiled, “Fuck my little pussy even harder, please, make me scream, fuck my god damn fucking brains out right now.”
Before she could say anything more, he was back to sliding in and out of her, but this time the pace was double what it had been before and before she even had time to moan, she was rolled from her back to her stomach, and face pressed into the pillow, drowning out her moans as her supply of oxygen was to limited to exhale anything. Todd then proceeded to continue slamming up to the end of her fuckhole as he explored the ass he had admired so much over the past few days and earlier in the night. He smacked it with the full force of his palm, causing Emi to spring up and groan in pleasure while gasping for air.
“Fuck do that more, spank my little tight fucking ass more, please don’t stop fucking my pussy and slapping my fucking ass.”
“Your wish is my command princess,” he laughed as he, once again, placed the full force of his palm on the cheek for her ass causing her to groan again.
Not long after that he pulled out of her, and in a moment of dazed confusion, Emi was picked up and placed on top him, and quickly found moved to hover over his dick.
“Take off the condom,” She commanded, “I want to fuck you raw.”
Quickly Todd slipped off the condom and watched as Emi slid his throbbing cock inside her. He watched her with his hands behind his head, as she rose and fell on him, giving her full effort into pleasuring him full allowing him to relax as she did so, but before long started to raise and lower his own hips against the rhythm of hers meeting on the collision. He eventually felt something rising inside him.
“I’m about to cum,” he groaned quietly.
“Cum inside me daddy,” she screamed as her pace rose, “Fill me with you hot sticky cum!”
Just has he felt himself about to cum he was met with a moment of air on his dick before Emi quickly placed it into her mouth as he quickly unleashed several spurts, coating her throat in cum, which she swallowed.
As Todd laid on his bed, panting in a pleasant afterglow. Emi once again sat on his stomach, but this time, she slapped him.
“What the fuck you were actually going to cum inside me weren’t you.”
Todd was confused, “Were we not having the moment where that happens? You said to…”
Emi laughed for a moment before looking down at him, “This is your first time isn’t it?”
“I’ve clearly had sex…”
“No I mean using a dating app for sex.”
Todd’s face turned red, “Well, yeah. I never really needed it before now so…”
“Todd you gotta be careful, you don’t realize it, but you got a good bit going on with you and girls are crazy and will try to take advantage of that.”
“What are you even talking about.”
Emi sighed and slid to the side of him, allowing him to hold her as she explained, “We know nothing about each other, but you were willing to take off the condom and continue to fuck me until eventually you were about to cum inside me without any knowledge of me being on the pill of if I had any STDs.”
“Well you said…”
“Listen, I saw you at the STD clinic the day we matched and overheard that you got a clean test, then happened to overhear that you got clean results, and because I knew this I decided it would be okay to fuck you.”
Todd now was completely confused, “So that’s the only reason why you were willing to have sex with me?”
Emi laughed and kissed him quickly, “No silly I also got out of something recently, I don’t know what your deal was.”
“Cheating girlfriend.”
“Pretty normal, then you got on tinder looking to fuck the first thing that breathes right?”
“That’s kinda rude to yourself considering that I just did it with you right?”
“I don’t worry about the details, what is important is that you’re good in bed, you’re kind of good looking, and you’re REALLY good in bed.”
“Thank you?”
“But you gotta be more careful, especially if you are planning on going out and doing this again.”
“So what do I do?”
Emi paused for a moment before responding, “I’ll help you out, I’ll give you advice, I’ll get you laid.”
The offer was too good to be true in Todd’s opinion, “But what do I have to do in return?”
Emi smiled, “I just want this,” she ran her hands up and down his shaft, “if you’re not in any sort of committed relationship, I want my share of this dick, and maybe the occasional food date doesn’t sound half bad either.”
Todd sighed a breath of relief, “Dinner and sex? That’s a good deal to me.”
Emi sat up, “As much as I’d like to offer a round two right now, I’ve got to get home tonight, but another night for sure, and make sure to text me before you try anything with other girls okay?” She winked as she finished placing her clothes and stood at the doorway.
---
Todd was sitting at his desk, alone now and in his underwear. He opened up a notes page and titled it “Tinder Notes” and began to type:
“I’m going to write this as a sort of journal to keep my mind off Kelly, and I learned that hooking up isn’t very easy.
Always wear a condom.
Always make sure the girl has no STDs
These are my first two lessons I learned from Emi and I’ll write anymore I learn while I’m doing this because… I might get addicted to this a little.”
Todd saved the document, shut off his computer and dove into his bed. He turned to face his phone, to notice he has a new notification, a new match.
The End
---
Post Story Note:
I hope everyone liked this possible intro to a series basically would feature Todd (and sometimes maybe even Emi?) exploring different kinks and pleasures with different types of girls. I think it’s also kind of cool that I’ve tried to structure it as a tutorial for tinder users, it’s important to practice safe sex and properly interact on tinder. This is not an accurate depiction of most tinder dates at all! If this story is well received I have a few ideas with how to continue it further on, but I’ll ask for anybody that enjoyed it, would you rather see more development to get to the sex or rather mainly just sex? I’ll always include a solid amount of content, but I’m curious if people actually want to read more about how Todd gets these girls (again these are not definite ways to get dates or anything like that and I’m not a girl so I can’t tell you anything besides sometimes somethings work for me). I’m rambling a bit here, but basically I hope everyone who reads with enjoys it and expect more to come if it is received well! Any if anybody has any criticism on the format, story, or this long post story note, let me know below! I read all comments!