The [F]irst encounter with [M]y long term fuck buddy

Many years ago, I established an incredibly convenient fuck buddy relationship with a truly pretty, and sufficiently freaky girl named Kayley. I will build off of this in the future, sharing more of our exploits as they are varied. However, this story is the one that kick-started it all.

Back in the days of instant messaging, I like many others of my generation, spent hours on end chatting, talking shit, crafting elaborate away messages, and sharing filth. Also, as is expected, and simultaneously unbeknownst to us, my online friends and I were paving the way for sexting.

In the midst of a conversation with a friend of mine, I caught the distinct audible indication of a new message.

Kayby018: *Hey*

That was the entire content of the message. My heart swelled, my stomach knotted, I had to respond with something quippy, witty, cool.

illetist90: *Hey*

Satisfied with my response, I awaited Kayleys advances.

Kayby018: *I saw you at the party last Friday, you looked really hot*

Oh man. She really ratcheted this up quickly. Her blunt, unapologetic observation would serve as an example of how most of our conversations would unfold. Kayley said what she wanted, when she wanted, however she wanted.

She continued unanswered as my fingers searched for the appropriate keys to stroke in an attempt to convey my appreciation for the sentiment, and my indifference… because, you know, be cool…

Kayby018: *We should hang out*

Oh shit. Yeah, we definitely should. I’ll take this opportunity, prior to sharing my profound and adept response, to describe Kayley. Kayley was a couple of years younger than me. We had gone to school together and had a similar group of friends. She was in her senior year, and I was lurking around town to figure out what I was going to do next. She was 5’7” or 5’8”, blonde, thin, but in an athletic way. She had full perky breasts, and a firm yet small butt. She had a smirk that crept across her smile nearly always, as though she was privy to something that the rest of us had yet to know. She was pretty, a gentle face, and often presented herself as aloof, or bored, or maybe indifferent.

Illetist90: *Yeah, that sounds good. What are you doing this weekend?*

Clearly I was an expert at communicating with women. I’ll save you the labored dialogue that followed, but aside from some poorly masked innuendo, we were able to coordinate a hangout for the following Friday. My house was empty, as my family was in a neighboring state for a few days. The opportunity was perfect, and I carefully prepared for the perfect sex that I was sure would occur.

Friday arrived and I picked Kayley up. She was dressed cutely, but nothing too revealing or suggestive. A v neck t-shirt, some snug fitting jeans, some cute jewelry, and her hair partially pulled back into a loose ponytail that left strands of hair sweeping her face. I distinctly remember her smell, a lightly fruity, somewhat vanilla scent that reeked of youth. She always smelled like that as long as we fooled around, and it was a staple and sexual trigger for me later in our relationship.

“You look great.” I commented, my anxious energy peaking.

“Thanks” she beamed, not a hint of nerve in her body language or appearance. Fuck she was so cool…

We made the meandering drive back to my house, making small talk as I inspected her body. We arrived shortly thereafter, uneventfully, and made our way to my bedroom on the second floor. To briefly set the scene, I had a fairly large room, a king bed, a futon in front of a TV, with a lot of space breaking up the furniture.

I flipped the TV on, sat on the edge of the bed, and the small talk continued. Kayley sat next to me, and the conversation met its natural end giving way to silence. We did the thing that you do with someone you’re sexually attracted to, stared at each other in silence waiting for the perfect moment, and I then hurriedly leaned in to kiss her.

It was officially on. We explored each other’s mouths. Our tongues met, mingled, danced, and then grinded until our lips and cheeks were covered in the others saliva. My hand slipped up her shirt, under her bra, as my palm felt the hardened and tiny nipple of her left breast. The kissing intensified as I massaged her through muffled moans.

We continued to claw at each other until my hands roamed down to find the clasp of her jeans. I quickly undid them, and slid them past her knees to reveal a lacy pink thong. Perfect. Next was her shirt and bra as one. Both came over her head simultaneously to expose her perfect C cup breasts, tiny rock hard nipples, neatly dotted in the middle of a perky tear drop silhouette.

“Fuck you’re hot” I muttered under my breath. She stared directly in my eyes with a look of pure passion, and a hint of submission. She peeled my shirt from my body, and I looped my fingers under the band of her thong, slowly sliding them down her legs to reveal her perfectly waxed pussy. The lips meeting to create her slit were perfect, glistening slightly and neatly situated to make the most beautiful cunt I’ve ever laid eyes on.

I kissed and licked up her shins, and sucked and tongued the back of her knee. I continued tracing my lips and tongue up her inner thigh, stopping to kiss and nibble as I got closer and closer to the delta of her legs. As my nose grazed the entrance to her body, I licked around her pussy, tracing the outline gently with the tip of my tongue. Kayley moaned quietly and intimately, her fingers running through my hair in an attempt to encourage a more direct approach to her pleasure.

“Please” was all she said, her eyes piercing mine, begging me to push my tongue into her folds.

I obliged, my tongue tracing up her slit until I felt the nub of her clit, settling on that to rock my tongue softly back and forth. Kayley moaned audibly, longer, and deeper. I looked up to see her biting her lip, watching me intently with that fucking smirk on her face, cheeks flushed red.

I brought my finger to my mouth, coating it with saliva, before I gently plunged it deep into her. I probably entered her too quickly, too suddenly, as she elicited another moan and an audible gasp. My fingers and tongue began to work in tandem, and Kayleys breathing accelerated. I looked up again to see she had grasped her right breast in her hand and was kneading it aggressively.

“Oh fuck illetist90, that feels so good” she squealed. I continued to work on her, until finally I looked up to see she had sucked her own nipple into her mouth. *holy fuck* I thought. *this girl is a freak*.

She must have noticed my moment of awe, as she smiled devilishly at me, leaning forward to forcefully grab my shoulders and push me to my back on the bed. Without a word spoken, she relieved me of my pants and boxers in one fell swoop, and nearly dove directly onto my very swollen and slightly leaky cock.

She immediately began to work her hand and mouth in tandem, rotating her top hand, her thumb and pointer meeting her lips, in an effort to extract all of the fluid in my balls as efficiently as possible.

I watched, still in awe of her enthusiasm, the slurping and sucking noises born of suction and saliva and the friction of her hand. Her free hand drifted to my balls, cupping them as she attempted to hoover the rest of my cock down her throat. Her pace began to overwhelm me, and I knew I wouldn’t have long. I had slipped my hand onto her head, the light pressure of my grip matching her tempo. My fingers gripped her hair lightly and I groaned;

“Turn around, I want to eat your pussy while you suck my cock.”

She happily obliged. Soon her pussy mounted my face, my nose nuzzled into her asshole as she resumed her duty of draining my balls into raisins. We both entered a fury, attempting to race each other into an orgasm. She began to bounce her throat off my cock head, gagging lightly, so that her drool dripped down my shaft and onto my balls. I buried my fingers in her slit, my tongue in her clit, with the thumb of my other hand tracing circles on her asshole. We both began to moan loudly into each other. I could feel the pressure building.

“Oh fuck, oh fuck, oh fuck… I’m gonna cum.” I grunted into her cunt. Kayley quickened her pace to a maddening rate, I reached my hands down to her hair and tits with my free hands. Finally, I groaned and pushed myself up into her mouth as I unleashed spurt after spurt of high velocity cum into her mouth. She dutifully sucked it all in, jerking all the while, as I came so much that it overcame her ability to consume it. I watched it dribble out of the corners of her mouth.

She moaned and grunted, an indication for her hunger for me. “Mmmmmm, yawh mmmmm” she grumbled in a hollowed our tone, with her mouth full, as my cock began to soften. She swallowed the last of the mess I made in her mouth.

“Holy fuck, that felt so fucking good.” I exclaimed, searching for breath.

She just smirked that smirk…

*this is part one, part two is the same day, we get into even more filth and I find out that Kayley has a cum fetish. I’ll do my best to get it up in the next few days*

Source: reddit.com/r/gonewildstories/comments/inhbn2/the_first_encounter_with_my_long_term_fuck_buddy