Online dating is a blessing and a curse. Sometimes it’s successful, other times it has you deleting it and redownloading it in a vicious cycle. I wouldn’t call this a success story, but it was fun and it had its moments. I matched with Kaleb on tinder early last summer. We had a lot of music in common and generally hit it off really well. It wasn’t long before we set up a date, which went pretty well and we continued to see eachother.
Kaleb was fresh out of a serious relationship, and apparently his ex was one of the few people he had been with. He was a year younger than me, so turned 20 a few months before I met him. I think. Point being he wasn’t as well versed in casual sex as I was. Truth be told he was pretty vanilla, but he essentially told me that’s what he was used to. If you’ve read any of my other stories, you’ll know I’m not one for vanilla, so I had to get this boy trained up. Thankfully, he was super willing. Over the course of us fucking, which happened a lot, I told him about the various things I was into, and he listened, getting more and more adventurous every time we hooked up.
By this point there were a few things we still wanted to do, I wanted to use my handcuffs and just generally get dominated, and he wanted to fuck me in front of the full length mirror I had in my room. So we planned a day for him to come over to my place after work and cross some things off the list. I made a whole thing of it. I went out and bought new lingerie, spent the day showering, shaving, and making myself cute in anticipation for that afternoon. I left my front door unlocked, as well as the door to my room so I could be in there, waiting in my sexy new lingerie for him. I was wearing thigh high fishnet stockings with lace at the top, matching black lace garter belt, panties, and a sheer halter top bralette that completely showed off my tits. I threw on an oversized flannel and sat on my bed with a book, trying to settle the jittery nerves that were stemming from my excitement . Soon enough I heard my front door open, and then he walked into my room. We made eye contact and I gave him a cheeky smirk.
“I don’t think you’re ready,” I teased, extending a stocking clad leg down my bed.
He didn’t say anything. Just raised his hand and motioned with his finger to come to him. I sat my book down and slowly stood up, sauntering over to him. As I got closer, I dropped my flannel to the floor, giving him a full view of what I was wearing. My heart was pounding as he raked his eyes over me, stepping closer and putting his hands on my waist. Our lips met, and despite what we knew was about to happen, it was surprisingly gentle. I deepened the kiss as I dropped my hands to his belt. I should mention that for his job he had to wear a suit, which made this situation ten times hotter for me. Him standing there looking completely professional and put together, and me, dressed like a complete whore, just waiting to be fucked. I dropped to my knees and teased his half hard cock through his boxers before pulling the waistband down. I slowly licked up his shaft then dropped my head down to the base, taking his now stiff erection down my throat. He let out a low groan and put a hand on the back of my head, encouraging me into a rhythm. I kept bobbing up and down, swirling my tongue around him, letting my saliva make an absolute mess. He wasn’t massive so it made it easier for me to take him all the way down my throat every time. I increased my speed and brought a hand up to cup his balls, giving them a soft squeeze every time my nose pressed against his core. He stripped off his jacket and shirt as I worked. Once his shirt was free, he grabbed both sides of my head and started fucking my face with surprising vigour. I opened my mouth and stuck out my tongue, allowing him to slide in and out of my throat with ease, wet gagging noises pouring out of my mouth every time he hit the back of my throat. I pulled back and looked up at him to meet his eyes, biting my lip and giving him a smile that I knew drove him mad.
“Stand up,” he ordered, and I listened.
He spun me around to face my mirror and pulled my drenched panties to the side, teasing my pussy with his fingers as he stepped out of his pants. He moved his hands to my hips, gently sliding his erection between my thighs. I reached down and gently pushed him towards my entrance and he slowly sank inside of me. He began pumping in and out of me as I got lost in the sight of our reflection, completely entranced with the way his cock looking sliding out and disappearing back inside of me. I watched a hand snake it’s way up my body and wrap around my throat, pulling my head back towards him. I put a hand against the wall to brace myself and arched my back, throwing my ass back to meet his hips. His other hand reached around between my legs to start teasing my clit and soon enough I could feel my legs shaking and twitching in response to his touch. He gave my ass a sharp spank before taking a step back and guiding me to the bed.
I fell back onto the mattress and slid off my panties as he opened my nightstand, pulling out my leather handcuffs and a bandana that we had previously used as a gag. He placed the gag in my mouth, and attempted to tie it behind my head but failed because my curly hair kept getting in the way. I giggled and tied it for him, then offered up my wrists to be cuffed. He grabbed them and placed them above my head, securing them to my headboard. He looked me deep in my eyes as he dragged a hand down my body, stopping to firmly squeeze my breast, then disappearing between my thighs. He gently teased my clit and I jerked against my restraints, earning a smirk from his face. He slipped two fingers inside of my pussy, which by this point was absolutely dripping. He pumped them inside of me at a brutally slow rhythm, causing me to throw my head back and groan into my gag. Pausing for a painful moment, he reached over and grabbed my vibrator from my nightstand, flicking it on and pressing it against my clit. He sank his fingers back inside me, slowly getting faster and faster until I was bucking my hips into hand. He pulled his fingers out and licked them clean, turning my vibe off and leaving it on the bed before lowering his face to my mound and diving in. I can say a lot of things about Kaleb, at this point a lot of them not so great, but I will hand it to him for being a giver in bed. He was extremely enthusiastic when it came to giving head, which everyone knows is the most important thing. I closed my eyes and let out a muffled moan, gently squeezing my thighs against his face and gripping the chain on my handcuffs until my knuckles went white. He turned my vibrator back on and eased it inside of me as he continued to eat me out. The shape of it was designed to hit my g spot, so the stimulation from him pumping it in and out of me as he sucked on my clit was almost overwhelming.
He finally sat up and grabbed a condom from my nightstand, sliding it on his cock before teasing it against my folds. I gave him my best “please fuck me” puppy dog eyes, which seemed to do the trick and he thrusted into me. It didn’t take long before he lifted my ankles to his shoulders (something I had expressed my absolute love for) and was pounding into me. I was whimpering and moaning as much as I could with the obstruction in my mouth, closing my eyes and throwing my head back. His hand found my face and firmly gripped my chin before slightly slapping my cheek, something else I had told him really turned me on, but was completely new to him.
“Look at me.”
I brought my head back and looked at him, seeing how dark and intense his gaze had become. I probably looked like a helpless little mess, which was the goal. He gave me another soft slap (he could have gone harder but hey at least he was trying), and put his hand on my throat, his free hand picked my vibrator back up and starting teasing me with it. We held each others gaze as he kept fucking into me, watching eachother unravel just a little bit with each stroke. He pulled out and leaned forward, undoing my cuffs. He told me flip over and I nodded compliantly, doing what he said. I laid down on my elbows and arched my ass up for him, rewarded with a couple spanks before he slipped back inside me. He instantly grabbed my hair, pulling it back, eliciting another muffled moan. He reached for my gag and pulled it out of my mouth, replacing it with his thumb. I eagerly sucked on it, revelling in the feeling of his cock filling me up and his hips meeting my ass with harsh strokes. Soon enough he brought the vibrator back to my clit and I finally opened my mouth and moaned. I clamped down on his cock and he groaned, only fucking me harder.
“Fuck that’s good,” he moaned as he rocked in and out of me.
I kept squeezing and releasing my walls against him, loving the sounds that were coming out of him. He pulled out and lay down next to me. I took the hint and straddled his hips, teasing his cock before sinking down onto him. I leaned forward and tried to do my best sexy hair flip, bringing my lips down to his neck and gently sucking as I rocked my hips back and forth. He kneaded my ass as I worked his shaft, moaning into his ear. He wrapped his arms around my waist to hold me still and started thrusting up into me. I sat up and threw my head back, letting a moan escape my lips. I put my hands on his chest and started sliding up and down on his cock, giving him that same slutty smile from before. Eye contact clearly worked for him, because as soon as I gave him that depraved, dick drunk, good little slut stare, his mouth would drop open and the look in his eyes would completely change.
“Fuck, I’m gonna cum,” Kaleb groaned, digging his fingers into my thighs.
I picked up my pace, bring a hand to grasp his forearm and the other gripped my headboard to give me more balance. “Fucking cum for me,” I begged in between moans.
He drove his hips up into me and let out a moan as his cock twitched inside of me. I gently ground against him to ride out his orgasm. I leaned forward and gently kissed him, slowly raising my hips to let his softening erection slide out. I flopped down on the bed beside him, both of us catching our breath.
Things ended with Kaleb not long after this. To put it simply, it wasn’t amicable. Regardless, for an obviously emotionally damaged vanilla boy, he was a quick study and a pretty solid lay.
Source: reddit.com/r/gonewildstories/comments/i210tz/training_the_sweet_vanilla_boy_to_fuck_me_the_way