[M]y [F]irst time with a girl

This is the story of the first time I had sex with a girl. I had had sex with a few guys before this and had been sexually active with my best friend since we where 14, but it wasn’t until I was 18 that I lost my ‘straight virginity’. It’s long with a bit of pre-amble, so if you want to skip straight to the smut please jump to the ******

I had been going out with Zoe for about a month. She knew about my bisexuality and was fine with it, she also knew that I had never been with a girl before as well. We’d had some hot and heavy make-out sessions before, she had felt my cock through my trousers and I had felt her boobs through her t-shirt but we hadn’t gone any further than that.

It was Summer in the early 2000’s, and me and Zoe had been out with some friends for the evening. It was pretty late and she wanted to go home. Being the gallant boyfriend I walked her home. We got to her house and we start kissing outside. As usual we got really into it and started groping at each other. She pulled away and said that she really wished she could finally invite me up, but despite technically being an adult her parents were still against the idea of her having boys over to stay, even though they apparently thought quite highly of me. I reminded her that my grandparents (who I lived with) where in London for the weekend and that I was home alone. Zoe cocked an eyebrow with a grin and asked why I hadn’t mentioned this already. She took my hand and we walked to my house, which was only 10 minutes away. That night though the walk seemed to take forever. The whole time she was making small talk and I was replying absent-mindedly, my head spinning with the possibility that Zoe would be staying the night with me. Doubt began to creep in. Maybe she was just having me on, and we would get to my door and she would kiss me goodnight and go home herself. She had a wicked sense of humour, it was one of the things that attracted me to her in the first place.

She looked over at me and asked what I was thinking. I said nothing much, and she grinned that grin again and said she’d have to give me something to think about. As I was considering how AMAZINGLY corny that line was, she pushed me up against a fence and kissed me roughly. I had still been hard from the kissing earlier, and the prospect of what might happen that night, but somehow I seemed to get harder still. She grabbed me through my jeans and began rubbing slowly; I thought I might cream in my pants. We carried on walking (with occasional stop for more making out) and finally got my house.

When we got inside I started to panic. I told myself to calm down; it wasn’t as though this was the first time I was going to have sex. But I couldn’t seem to control my mouth, which seemed to be running at 90 words a second. I asked if she wanted a drink, or something to eat, or would she like to sit down, or watch something on TV, or a DVD or…

She stared to laugh and kissed me gently. “Why don’t you show me your room?” I was trembling, a deep internal tremble that always occurred when I got sexually excited. I led her upstairs and took her to my room. I was just coming out of a goth phase, so there were a fair amount of heavy metal posters all over the darkly wallpapered walls, a sound system in the corner (with a triple CD-changer! Ooooh so early 2000’s!), books all over the place and a single, unmade bed. I just said “Well, uh, this is it!” I had no idea what to do. My heart was racing, my body was trembling and I felt like my dick was going to rip it’s way out of my jeans and start rampaging round the room on it’s own. She touched my arm and I turned around to face her. She kissed me and said that she would like a drink after all.

I practically fell down the stairs on my way to the kitchen. What should I get her? Did she say hot or cold? Hot seemed ridiculous at this time of night, or was that subtle hint that we might need caffeine to keep us up for a while longer? Should I have some coffee? No no no, coffee might make my heart vibrate out of my chest. I settled on a glass of water eventually.

******

I took carried it back upstairs and back into my room. When I entered my heart almost stopped. She was in my bed, up on one elbow facing me. There was a pile of clothes next the bed. There was a bra on top of the pile. I came within an inch of dropping the glass.

She smiled and said “Clothes off, in bed, now.” I stripped off in a flash, but hesitated at my boxers. Was I being too presumptuous in getting completely naked? She saw me pause and said “Lose them.” I took them off and a long string of pre-cum dripped off the end of my cock. She reached out and rubbed a little off of the end. She put the finger to her tongue and licked it theatrically. I lifted the duvet and slid in beside her. Her hands where all over me immediately, her lips crushed to mine with her tongue in my mouth. We where on our sides, facing each other. I slid my arm underneath her and pressed her to me so her breasts where against my chest. My other arm started to run down her side lightly. She was gentle, kissing me hard and raking her nails down my side and back. My trembling was at it’s peak, and she asked if I was OK, looking into my eyes with concern. I explained that it was just a thing that happened when I got excited, and she laughed told me to relax. Might as well have told my dick to deflate on the spot; wasn’t going to happen, love. She lifted her leg and wrapped it around my ass, pulling me in such a way to motion that I was roll on top. She wrapped her other leg around me, and I felt warm wetness against my shaft (average size, slightly girthy, circumcised. In case you wanted to know). She began to grind her hips against me, rubbing my dick against her wet lips and clit. She started to moan into my mouth and I thought I was going to cum straight away. Then I had a horrible thought.

I broke off the kiss and said “I don’t have any-”

“Don’t worry about it.” she replied.

“But-”

“I said don’t worry about it.” Again; my brain was firing as lightspeed. Did she mean that I shouldn’t worry because we going to go raw? Or was this going to be a super heavy make-out session with everything but sex? My body was on autopilot; kissing deeply and grinding away with my cock sliding between her labial lips. It felt amazing, and there was a real danger of me cumming from this alone, however my preoccupation with my own thoughts was likely what saved me from firing off prematurely.

She broke off the kiss and looked directly into eyes, along with that grin. I normally get uncomfortable with looking someone directly in the eyes, but this felt special, this felt like an intimate connection. She reached down, pushing her hand between our locked hips and I raised myself up on my elbows and raised my butt in the air.. She grabbed my member, sliding her hand along the shaft to spread the mingled wetness of her juices and my precum. Again, this was almost too much. I was so tightly wound I made a guitar string look slack. I trembled severely and let out a loud sigh/moan.

“Are you OK?” she whispered. The tenderness in her voice made my heart flutter. She was normally quite the tomboy; all brash humour and pop punk grrrrrl power, but here; in this singular moment with just the two us, naked and exposed, there was true affection in her eyes and in her voice, and it made me feel a true connection with.

I smiled and half laughed. “I don’t think I’m going to last too long, here. This is all very hot and heavy.” The grin returned with a gleam of mischief in her eye. “Don’t worry about that, we’ve got all night.”

She rubbed the tip of my cock against her clit a few times, then positioned it lower. I felt heat and wetness on my tip, and instinctively thrust forward slowly. There was no resistance, just an amazing sensation of slick warmth that moved down my shaft. Clearly the situation was making her as turned on as I was. She let out a small sigh as I pressed myself all the way in and held it there, not wanting this moment to end. She brought her legs up and wrapped them around me again while I raised myself up onto my hands and looked down between us to where we were now joined. I pulled back slowly, relishing the sensation of her inner walls around my cock, and watched as my cock slid almost completely out of her, before slowly burying myself in her again. As I said before; I’d been with men, having fucked and been fucked by them. But this was something else entirely. Every sense was alight. The sight of Zoe beneath me, breasts bare, dirty blond hair spread out on my pillow like a halo, looking up at me with slightly parted lips with a hint of a smile in her blue/green eyes, hands on my waist and legs around my butt. The smell of her body and sex mingled with my own, creating a musky warm scent. There was warmth between us, not just where we were connected at the groin, but a full body heat that felt like it connected us. Her breathing was a small yet lovely sound, like small ‘ha’ with each thrust. Not that there were many of those, I have to admit.

All these sensations came to me in an instant hit, almost overwhelmingly. Thrusting back in again felt even better as I bottomed out, pushing as far as I could and holding it there. I knew I wasn’t going to last much longer. On the next slow withdrawal and thrust the familiar feeling of an impending orgasm began to build, and I began to breath heavier. “Ah shit I’m going to cum,” I gasped out and in the next second I came harder than I ever had before. I moaned loudly as I kept thrusting through the orgasm, my body shaking not with nervousness this time but with ecstasy. I could vaguely hear Zoe saying something, but I have no idea what. I stopped moving, the sensations too much for me, but I stayed inside her, relishing the feeling of connection with her. She reached up and pulled my face to hers, kissing me long and deep. I gently collapsed onto her, sliding a hand down to grab her butt.

We lay that way for a while, just kissing and caressing each other. I don’t know why, but I always stay hard for a good 15 minutes after orgasm, so was still quite firm inside her, but was quite sensitive. I broke the kiss and gave a half laugh. “Holy shit.” I couldn’t really articulate anything else.

“Was it what you were expecting?” she asked, with that grin.

I propped myself up on an elbow again. “It was intense. Like really intense. I didn’t really know what to expect to be honest. It’s very different with the guys I’ve been with.”

“How so?” She didn’t sound annoyed at me bringing this up, which I immediately regreted as soon as the words left my mouth, but actually interested.

“I don’t know, less intimate, I guess? I felt a real connection with you-”

“For that whole 30 seconds, yeah?” A full-toothed smile this time. The tomboy was back.

I laughed, happy to take the dig. “Yep, for those 30 seconds I felt connected to you in way I’ve never felt with anyone else. It was a bit overwhelming, to be honest.”

“God, you’re such a girl.” The words were playful, and she pulled me in for another heavy kissing session.

I was still hard inside her during this, and it showed no signs of abating. However a few test movements still proved that I was too sensitive for round 2. So I pitched another idea.

“Can I go down on you?” I asked, out of the blue.

Her eyebrows went up slightly at this. “I mean, sure, if you want to. It might be a bit of a mess down there though. I don’t want you getting put off on your visit.”

“Duly noted. I will attempt to assess the state of affairs up close. I will present a full report shortly.” Did I mention that I’m a dork? Because I’m a bit of a dork.

I withdrew and inhaled sharply at the sensitivity. I realised then that I hadn’t really seen Zoe properly naked yet, and took this opportunity to rectify that. The light was off but there was a streetlight across the road which had always given my room decent illumination. I had pushed my self up to a kneeling position and was looking down at her naked form; it was a beautiful sight to be sure. Her hair was all over the place. Her boobs, not perky by any means, where soft and inviting with stiff, light brown nipples in the centre. Her very slight belly was glistening slightly with sweat where I had been lying on her. The look of mischief that was never far away was twinkling brightly in her eyes. Her legs where slightly raised with the knees bent around my thighs, and her shaved pussy sat there in the middle; just waiting for the first touch of my novice tongue.

I didn’t waste any more time and shuffled myself down until my face was between her thighs. I could smell musk that I had picked up before, just far stronger and far more intoxicating. I licked gently at first, not parting the lips but brushing over them. Instantly I got a small moan from further up the bed. I licked again, harder this time, pushing my tongue down the middle and tasting her properly for the first time. She tasted warm and sweet; I couldn’t get enough of it. I licked harder again, and this time I felt the hard nub of her clit at the top of her slit. She moaned louder then and ran her fingers through my hair; pulling my head gently toward her. I didn’t need any more incentive and went work with gusto.

Though I hadn’t been with a girl before I had watched a fair amount of porn, and knew that if I concentrated on the clit too much she might become over sensitive, so I worked on starting at the bottom of the slit and slowly working my way all the way to the top. At the bottom I felt the hotness that was her hole, and tasted my own cum mixed in there. I had obviously tasted cum before and it didn’t bother me, it may have actually turned me on that much more. I knew that rhythm was an important part of eating out as well so I kept a steady bottom-to-top licking action going. She was squirming and moaning constantly now, grabbing my hair to get me to apply more pressure. She was bucking her hips faster, so I started licking faster to keep up. I didn’t really know what to do with my hands, so just placed them on her upper thighs. She put her legs over my shoulders, took my hands and placed them on her boobs. I immediately started to play with them; squeezing and rubbing my fingers over her rock-hard nipples, the whole while licking hard and faster and she moaned louder and louder. Who says men can’t multi-task?

I don’t know how long we kept it up for until she started to judder and tremble, pulled my head back and said “Fuck me,” in a breathless voice. I moved up and positioned myself again as I had before; arms straight, hips connected. I tried to put it in myself this time, but simply couldn’t get the angle right. She grabbed me and guided me in, then moved her hand to her clit and began to play with herself. When I entered her this time she felt much tighter but no less wet. She moaned loudly when I slid all the way in and wrapped her legs around me again. I started thrusting quickly this time as I felt much less sensitive than before. Her head was back with her neck bared, so I started kissing and nibbling it as I went. She put her free hand on my waist and got into rhythm with me. Her pace was quickening to I tried to keep up and pretty soon we where both breathing heavily. I could feel her tightening around my cock like she was trying to push me out so I started thrusting harder. She started going “oh fuck oh fuck oh fuuuuuuuuuuck” and I knew she was about to cum herself (either that or she was faking it for me, I was happy either way). I was getting close again due to the tightness and the pace, and started moaning myself.

She came first; her breathing stopping for a long second as her body stiffened. She pulled me to her roughly, her arms locking around my shoulders as her body relaxed again, her breathing coming back heavily and her pussy pulsating around my cock. It felt glorious. She didn’t scream theatrically but moaned loudly in my ear. I came just after her; the clenching her inner walls around my manhood tipping me over the edge quickly.

We where both covered in a sheen of sweat as we kissed hard, hearts pounding like we had run a marathon. We broke off, breathing heavily. I withdrew immediately this time, the sensations of leaving her almost bittersweet.

“I guess I did something right then?” I asked with a grin as I rolled over to her side, causing her to have to shuffle up and turn on her side to face me. I now had my back to the windowed wall. Single beds, ammarite?

She nodded in answer and kissed me again, gentle and sweet. We retrieved the duvet, found a box of tissues at her request (not hard to find in an 18 year old boys bedroom) and talked some pillow talk. We were basically nose to nose, and I kept running my hands lightly along her sides and thighs, producing a few giggles. Eventually she flipped over so we were spooning. I slipped an arm under the pillow and draped the over her waist to cup a boob. Pressing myself to her my now flaccid cock rested on her butt-crack, and immediately began to get hard again. She obviously felt this and gave a little wiggle, but didn’t pursue things further. Taking this as a hint I didn’t start dry humping her butt (though it was, uh, hard). We talked a little more while I kissed her neck and shoulder, then we both drifted off to sleep.

I don’t know how long it was later but I when I woke up it was still dark and we were still in the spooning position. I came immediately awake, no grogginess or confusion. I was almost in shock at how things had gone down (so to speak). It has been a truly amazing experience, and certainly cemented that I was bisexual as I DEFINTELY wanted this happen again. As many times as possible, in fact. I wanted to go again, as began to get hard at the thought but immediately started to doubt myself as to whether Zoe would appreciate being woken up for another round. Horniness won out over anxiety in this instance though, and seeing as my right hand was still full of boob, I started there.

I began to very gently move my hand so that I could rub her nipple with my thumb. This quickly had the desired effect as it began to stiffed. I moved the rest of my hand under the breast as I gently rubbed with my thumb and forefinger. I pressed my now solid and precum leaking cock against her butt-crack and began to gently hump her awake. I started gently kissing her shoulder and she turned her head toward me. She looked beautiful, all full of sleep with a smile on her lips. We kissed again and she moved my hand down between her legs. She parted them slightly to give me access while I dry humped her butt. Not having explored a pussy with hands before I probably didn’t do fantastically the first time, but after some guidance I found her honeypot and was able to her motor running to the point where she moaning in my mouth as I slipped a finger inside her.

After a while she opened her legs fully while still on her side and grabbed my cock from between them. She moved it so the head was almost level with her clit then closed her legs again. A few gentle thrust and my shaft was coated in her juices. I slid between her thighs straight along her lips, if I thrust hard enough at the right angle I was just able to rub her clit with my tip. She had stopped twisting to kiss me now and was turned away from me again, clearly getting into this non-penetrative humping that we were doing. I looked down at our bodies locked and sliding together and it was incredibly hot. I held her hip in one hand and snaked my left under her so I could cup a boob from below. We rocked together this way for a while, the sensations for me being very pleasurable but not quite enough to tip me past the point of no return.

Suddenly she jerked slightly which changed my angle just enough that I entered her unexpectedly with a hard thrust. She gasped and I stopped moving, panicking immediately that I had hurt her. She looked back at me and said it was fine, she just wasn’t expecting it! She repositioned herself again, almost doing a lying sideways doggy style. It was a far over as she could go before falling off the bed. She reached back and grabbed my hand, placing it on her hip. I took this as a suggestion to have at it. So I did.

I started to fuck her slowly, it felt so good to be inside her from behind. The position didn’t allow me to full-on thrusts, so I kind of stayed inside her and did very shallow movements. It was all very slow and sexual. Zoe was moaning gently, rocking her butt in time with me to get a good rhythm going. Despite already having cum twice, I didn’t last too long this time either, such was the horniness of the situation. Again I blurted out “I’m gonna cum!” before doing so, loudly. After I withdrew and duvets were again recovered etc etc I sheepishly said I was sorry for shooting so fast again. She faced me and kissed me, saying I got a free pass as it was our fist night together. But she’d get hers in the morning. I raised an eyebrow, she raised one back and we both laughed. More kissing ensued before we fell asleep again.

I woke in the morning to find myself on my back with this gorgeous girl straddling me. The sun was just up and she was lit up like some celestial being. I was a scene directly out of my fantasies. She saw I was awake and laughed. “Aww, I was hoping to get you inside me before you woke up.”

I was already hard, of course. She grabbed my cock and pointed it upward, then raised and lowered herself towards it. She rubbed the tip against herself a few times and spread her juices all over the head and shaft, then slowly lowered herself onto me. It was a hell of sight, watching my cock disappear into her, seeing the point our groins were now connected, feeling her thighs beside my hips. She started to rock her hips back and forth slowly, grinding against me, moaning the whole time. She grabbed my hands and placed them on her boobs, and I went to work, rubbing, squeezing, caressing. her grinding got harder and lent back slightly, using one arm to prop herself on my thigh, the other hand going to her clit and rubbing. Before long I felt her starting to tighten again. I could feel myself getting closer, this whole scene being the most erotic thing I’d ever witnessed. Her grinding and heavy breathing got more erratic before she finally climaxed with a cry, going rigid again before falling forward onto me. I surprised her by grabbing her around the body and flipping her over onto her back, which got me a shocked giggle before I re-entered her and fucked her hard and fast til I came again a few seconds later.

This was our first night together and it changed my perception of my own sexuality forever. We had many other great times, but our fling was short-lived. I have a lot of other stories if people are interested; with both men and women (and both at the same time on a few occasions), so please let me in the comments if you’re interested in hearing more from me.

Source: reddit.com/r/gonewildstories/comments/ryq246/my_first_time_with_a_girl