Taking his virginity (after a lot of fantasizing) [MF] | 2016

I'm a very long-winded writer, so if you just want to skip until the actual sex head for the *******

Before Blake, I'd had sex with three guys. All had been nice, but rather underwhelming. Blake was different from the beginning. I couldn't stop fantasizing about him. We met through online gaming--he was a friend of a friend. Although he lived in another country, we quickly became quite close, messaging daily and eventually voice calling once or twice a week, to watch shows together, game, or just talk. Despite being extremely different people--he was very artsy, and I was a hardcore science student--we had a lot of common ground when it came to shows, interests, and even deeper beliefs about life.

Things were very platonic for a long while--we'd have slightly flirty inside jokes, but nothing obvious or intense. I happened to know that he was a virgin, probably hadn't even had his first kiss yet. But his voice got under my skin and turned me on like nothing else. We'd often stay up so late I'd be lying in bed with all my lights off and headphones in, just listening to the sound of his voice. It was just the right combination of rough and deep that had my mind running as to what it might sound like whispering some nasty things in my ear.

One call, his voice got to be too much and I slipped a hand under my shirt. As he talked about his classes in uni, I began to gently rub my nipple, biting my lip to keep from moaning into my microphone. I closed my eyes and I could pretend his hand was on my breast, caressing me, slipping lower into my shorts ... when my fingers touched my aching pussy I involuntarily let out a low moan. I froze--he must have heard. I loudly rustled my blankets in the hope he would think I'd just sighed while rolling over. He hesitated, but just kept talking. I began gently rubbing my clit. I was soaking wet just from listening to him talk about analyzing literature. "Are you still there?" he asked. I guess I'd been silent for a while, concentrating on not making any noises while pleasuring myself. "Yeah, I'm here...just sleepy" I said, a little too breathily. I withdrew my hand, too scared to risk anything further.

But as the weeks progressed, I became more and more daring. Part of me wanted him to hear my shaky breaths and my little moans, but another part of me didn't want to make things weird between us when our friendship was going so well. Regardless, I progressed from rubbing my clit to fingering myself while we talked, all without him having a clue (at least I'm pretty sure he didn't). Occasionally he'd let out a little groan of frustration or tiredness and that pushed me over the edge. I never actually came while I talked to him--there's no way I could trust myself to do that surreptitiously--but it felt so fucking good to touch myself with his voice in my ear.

We finally met in person after about six months of talking. There was a whole group of us who played games online together who were meeting in Blake's hometown. I remember being so nervous walking down the steps to baggage claim. He'd called my beautiful and gorgeous a couple of times throughout our conversations, and I was scared he wouldn't find me the same way in person. On snapchat you can choose your best angles--in reality not so much.

In terms of my physical appearance--I'm 5'7" with a very slim build--naturally flat stomach and toned, long legs, with a round ass. I have perky C cup boobs with puffy nipples that become rock hard as soon as I'm aroused. One of my best features, or so I've been told, is my long and wavy dark brown hair that falls midway down my back. I also have blue eyes and relatively full lips. Blake is 6'0" with dark curly hair and dark eyes, a fairly slim build, and the sweetest smile.

I'm not going to lie, meeting Blake in person was incredibly awkward. We hugged and smiled shyly and conversation died very quickly. The 30 minute ride from the airport to his house made me wonder if the chemistry I'd imagined between us time after time was actually present offline.

But the more we talked in person, the easier and more natural it felt. It helped being surrounded by other friends too, but by the third day together I felt so comfortable with him I wished we could get more time alone. I'd fantasized about something happening between us so often I was determined to at least try to make a move.

While I was sharing a room with a few other people in Blake's house, I knew he had his own room. On the third night, after everyone in my room had gone to sleep, I messaged Blake asking him if he was still awake. He didn't respond for just long enough that I'd given up hope before he texted "nope, why?" I sent back: "I can't sleep. Want to watch an episode of The Office in person instead of online?" My heart was beating out of my chest. Even though the message wasn't that flirty, I wasn't used to having to make a move on someone, let alone someone I cared about as much as Blake. Luckily he replied yes, and I crept out of my room and down the hall into his.

He was sitting on his queen size bed with the light on, wearing pajama pants and a t-shirt. I felt my heart beat wildly at the idea that if all went well I'd be seeing him without any clothes on him. I tried to act casually despite the adrenaline coursing through my veins, sitting down with a bounce onto the bed next to him and smiling. "Hey" I said. "Hey. This is a bit of a change, huh?" he said, grabbing his laptop and logging into netflix. "It'll be nice not to have to deal with a bad connection though." I said, lamely. I was too caught up with imagining future, rather dirty, situations to focus on the present one. "Here, do you want to sit against the headboard?" he asked, sliding more into bed in what I took to be a good sign. "Sure. Should I turn off the lights?" I asked. He blushed a little bit. "Sure, if you want." We had suddenly regressed to the same level of awkwardness we first had. But I was determined to not let this chance slip by.

When I sat down on the bed, I made a point to sit close to him, so our shoulders and thighs were touching. As the episode progressed, I gradually let myself melt into him, until my head was firmly nestled on his shoulder. When I felt him gradually lift his arm and place it around me, drawing me closer to him, I couldn't help but shiver. Every one of my nerves was on edge. Six months of anticipation had been building up to this one night.

After the episode finished, there was a moment of awkward silence. I decided to harness as much courage as I had and broke it by saying: "Hey, I really like you, you know?" which was not exactly how I intended it to come out. But Blake broke out into a blushing smile. "Really? I mean, I like you too." I turned my face towards his and we made some of the most intense eye contact I've ever experienced. He seemed to be hesitating about what to do, so I tilted my face towards his and closed my eyes, waiting for a kiss. When I felt his lips finally touch mine, ever so gently, it felt like my whole body was on fire, with sparks travelling up and down my spine like a freeway. He kissed me softly and tentatively at first, one arm still around me. I leaned in, deepening the kiss, and reached up to tangle my fingers in his hair. He brought his other hand to my waist and drew me in closer. We kissed just like that for a while--I didn't want to push him too far, too fast or make him do anything he wasn't comfortable with. As far as I knew, this was as far as he'd ever been with a girl.

But fuck, if I wasn't soaking wet already just from this kissing. I brought my hands up under his shirt, feeling his warm back, pulling him into me. He took the hint and slipped his hands under my shirt. I let out a sharp moan--I couldn't help it. His touch was electrifying. I could feel his breathing quicken when he heard that. His hands roamed up and down my back, pressing me towards him. I got onto my knees and put one knee over him, so I was straddling him while we continued to make out. I could feel his cock, already hard, below me and it turned me on so much. I was breathing heavily as I began to subtly grind on his cock. He let out the hottest little moan I've ever heard, causing my to grind harder. I reached to the sides of his shirt to begin pulling it off; he raised his arms and let me pull it off of him. He had a good amount of chest hair that I immediately tangled my fingers in while we continued to kiss. I could feel his hands grasping at the hem of my shirt, so I raised my arms to let him take it off. I'd forgotten briefly that I wasn't wearing a bra because i was in my pyjamas, but I remembered when I felt the air hit my already rock-hard nipples, and saw the look on Blake's face.

He stared at them for a second before looking up at me, as if to make sure this was okay. In response I took one of his hands and placed it on my breast. He didn't really move it, just looked down and then back up at me. He looked suddenly sheepish and he took his hand off of me and said "I'm really sorry, it's just that I've never done any of this before, and I really have no idea what I'm doing." "Well, you're doing pretty well so far. And I can show you what to do if you want, but we also don't have to go any further. We can do whatever you're comfortable with." I told him. As much as every part of me wanted to fuck him, I wanted his first experience to be something he wanted too.

"No, I want to ... keep going. I just don't know how exactly." He said. I smiled and took his hand, and placed it back on my breast. I moved his thumb over my nipple, rubbing it gently. He quickly got the hint, and brought his other hand up to do the same. I moaned and bit my lip. We kissed for a while while he rubbed my nipples. I felt like I'd soaked through my underwear and pajama shorts by this point, and I couldn't help but rock gently back and forth on his still-hard cock.

"You can suck on my nipples too, if you want. Flicking them with your tongue feels--" I cut off with a gasp as I felt his mouth on my nipple, sending shockwaves through me. "Fuck, that feels good" I said, placing my hands on the back of his head for encouragement. He switched nipples after a while and I honestly thought I might come just from nipple stimulation, which I'd never felt before. But after a while I was getting impatient to see his cock. It felt pretty substantial beneath me, but it was hard to tell. I pulled his head back up to mine and we kissed some more--harder, sloppier, more full of desire. I turned his face away and began to kiss his neck. He moaned again, and that was all the encouragement I needed. I moved off of him and told him to lay down. Then I swung back over him and began to kiss his neck again, this time travelling further down, licking his nipples, kissing my way down his chest. I wasn't the most confident about my blowjob skills, but I'd had some experience and I wanted to make his first blowjob a good one. I took my time trailing kisses down his stomach, enjoying the way he squirmed and his breaths got more ragged. Finally I pulled down his pants and boxers to reveal an absolutely magnificent cock. I think I actually gasped. It was only slightly larger than average, about six inches I think, but it was thick and beautifully shaped and hard as a rock. "You've got a nice cock" I told him, and he blushed and said "Just so you know, I have a feeling I'm not going to last very long. I've never had ... well ... " he trailed off looking sheepish.

"Don't worry about it, just let me know when you're about to come." I told him before resuming my kisses everywhere but his dick. I got so close my nose brushed it, but I wanted to build the anticipation as much as I could. Finally I licked his cock from base to tip, flicking my tongue over the head. He groaned, and I finally took him in my mouth, prompting a "fuck" from Blake. I started slowly, just my mouth, licking my way around to lube up his cock properly before setting up a rhythm in earnest. Normally blowjobs don't turn me on that much, but hearing Blake's moans and feeling his hot cock in his mouth was turning me on when I didn't think I could be turned on any more. It wasn't long before Blake muttered "i think I'm going to come". I hummed my assent on his cock and kept sucking and stroking him even faster. "Fuck ... oh fuck, Haley, I'm about to come" he said, his voice breaking in the hottest way. "I'm coming!" he groaned as I felt his cock throb in my mouth. I kept sucking as I felt his hot cum hit the back of my throat, as he twitched and moaned below me, until he finally shuddered back onto the bed. I swallowed, and then gently released his cock from my mouth.

I slid up next to him in bed, watching his breathing slowly calm down, seeing the red flush of his face. I was both satisfied and even more horny than before, but I didn't want to push Blake any further if he was done for the night. He rolled over towards me. "That was incredible" he said. I was the one blushing now. "Thanks." "I'd like to return the favour, but again, I don't know what I'm doing." My pussy ached just at the thought. "I can show you." I told him.

I pulled his face towards me and hooked one leg over his body. I kissed him again, hoping he wouldn't mind post-BJ kisses. He didn't seem to. I guided his hand to the waistband of my shorts and slipped it underneath. Just the first touch of his hand to my pussy was incredible. It was the moment I'd imagined countless times, but this time it was actually his hand touching me. "Rub with two fingers, in circular motions. Not too hard, like this." I told him, guiding his hand with mine. "Fuck, Blake" I gasped. He was a quick learner, and I got off on clitoral stimulation pretty fast. He took initiative and began to kiss my neck--one of my weaknesses--and I moaned, loudly. The combination of his hot kisses on my neck and his fingers on my pussy and the fact that I'd been imagining this exact moment for months meant I didn't last very long at all. "Fuck, Blake, I think I'm going to cum" I breathed into his ear. He began to rub harder and faster in response. "No, just keep doing what you were doing before" I instructed him. He went back to his gentler, slower circles and I moaned again. He brought his lips back onto mine and I kissed him sloppily, dizzy with pleasure. I moaned into his mouth as I felt the familiar pressure building, cluing me in that I was about to orgasm. I tilted my mouth away from his: "I'm gonna cum, fuck, I'm gonna cum, don't stop--" I devolved into breathy moans as I came, hard. I had to grab his hand to stop him when my legs began to shake.

It was his turn to lay back beside me, but I was the red-faced and panting one now. "I guess it's my turn to say thank you." i said, smiling at him. "I didn't know it would be that quick" he answered, before quickly saying "not that that's a bad thing, I was just surprised." I laughed. "Usually it's not, but I was just really really turned on." I hesitated. "To be honest, I've been fantasizing about this for quite a while." "Really?" "Yeah, sorry if that's weird." "No ... I mean, I have been thinking about it too." After a pause, he added. "It's much better in reality though." I laughed again and leaned in to kiss him.

We started kissing slowly, gently; I traced lazy circles on his back as he tangled his hands in my hair. But then the kiss got more intense as both of our lust kicked back in. I pulled him on top of me and we began to make out again in earnest. I bit his lip gently and lightly dragged my fingernails down his back. He exhaled hard and I could feel his stiffening cock press into my thigh. I shifted so it landed between my legs and he began to gently grind into me. It was the sweetest torture feeling his cock so close to my pussy, separated only by thin shorts and underwear, so close I could feel the heat of it. I decided I needed my shorts and underwear off, now. "Just one sec" I said, reaching down to pull them off. "Allow me" Blake said, hooking his fingers into the waistband and pulling both shorts and underwear off. I pulled his body back onto mine immediately. I wanted to feel his hot cock on my pussy, skin-to-skin. When I felt his dick sliding over my slick pussy, I moaned again. I wanted his cock inside of me so badly, I could hardly think about anything else.

"Do you want to have sex?" I asked him straight out, because I was too horny to think of anything clever. "Yeah. I mean, if you want to." he responded. "Do you have a condom?" I asked. He shook his head. "Damn it. I don't either. But I am on birth control, so we should be okay." I said. He nodded. "Are you okay if I go on top?" I asked. I figured it would be easier for his first time, and this was the position I had fantasized the most about. "Sure, yeah." he said, rolling over onto his back. I straddled him, looking at his expectant face as I positioned myself over his cock. Using my hand, I guided the head to the entrance of my pussy. Fuck. Just the tip felt so good. But sinking down and feeling his full length enter me was the most satisfying feeling. I moaned, loudly, and he did too. "Fuck, you feel so good." I told him. I just stayed there for a while, enjoying the feeling of being so perfectly filled up.

I gradually began to move up and down. I almost moaned with every movement, it felt that good. I was so wet and he fit so well inside of me. I leaned down to kiss his neck as I rode his cock. "Oh my god, Haley...you feel amazing" he moaned as I kissed him. I began to move faster, my lust taking over my controlled movements. I had never had sex like this before, where every sensation felt so good, and where watching my partner turned me on even more. I loved watching Blake's face contort with pleasure, his mouth open to gasp or to groan, as I rode him.

He tentatively reached a hand up to cup one of my breasts; I bit my lip in assent and then moaned as he began to rub my nipples as I bounced up and down on him. The added stimulation began to push me over the edge. "I think I'm gonna cum again" I said. I leaned down to kiss his neck again in the hopes I could get him to come again too, with me. I left sloppy, hot kisses on his neck before I whispered in his ear "are you going to come for me too?" He groaned and with that I was past the point of no return. I sat up and began to grind on him, hard. "Fuck, fuck, fuck, I'm coming" I moaned as I came again. It was almost more intense than the first time as I could feel his cock inside me as my pussy walls clenched and unclenched. I guess my spasms pushed him over the edge too as he groaned "I'm coming too". I collapsed on top of him as the waves of orgasm subsided and his cock softened inside of me. After a few moments of regaining our breath, he tucked some of my wayward hair behind my ear and gently kissed me again. "Thank you." he said quietly. "That was better than I could have imagined." "I'm glad you had a good first time." I told him. I felt so happy, and finally satisfied in a way that I'd been missing for months.