[M]y first time giving a girl her [f]irst two orgasms

I (25M) have spent so much time reading and getting off to stories on this subreddit. I didn’t think I’d ever submit one of my own experiences, but here I am, 2 bottles deep into my favorite (9.5% ABV) beer and ready to share. Consider this my “thank you” to this community’s authors. I thought I’d share this while it was still fresh in my memory. Keep in mind this is my first time submitting a lengthy text post, so please let me know if there are any typos, grammatical mistakes, formatting concerns, or general critiques. I’m also open to general feedback.

This past summer started with casual, nonexclusive dating and ended with a relationship in every sense of the word minus the label. Naomi’s (24F) grad school, the new long distance between us that came with her master’s program, her grieving a 4.5 year relationship that ended 3 months before we met, and general incompatibility culminated in an agreement to breakup this past Saturday. Truth be told, I had sensed it was coming to an end in the past several weeks, but in my naiveté I thought it could be salvaged. Oh well. Live and learn.

Less than half an hour after our breakup around 8:30 P.M. this past Saturday, I began the process of revising my Bumble and Tinder profiles. I’d be lying if I said I hadn’t been grappling with an itch to meet new women, taste new bodies, and hear new moans. My now former flame was vanilla in the bedroom. Finishing in her mouth was almost always a no-go; the warmth, viscosity, and sensation of ejaculation would result in her gagging and possibly vomiting. The size of her mouth and the sensitivity of her gag reflex made blowjobs challenging. Deep penetration and certain angles were painful for her, so I was usually limited to a wide-leg missionary and front-facing cowgirl position. Bless her, she tried. I was hoping to turn her out, but it didn’t pan out as I had hoped. Please don’t get me wrong; my intention isn’t to shame her for her sexual reservations, but it has to be said that we didn’t exactly click and this context serves a purpose within my inaugural post.

I matched with Edith (25F) at some point during Sunday afternoon. Dark brown wavy hair, a light complexion, glasses, a round face, a soft and gentle expression, between slim and average, wide hips, and overall a bookworm kind of vibe. After 5 months away from the mercurial world of online dating, I wasn’t expecting to have anything happen anytime soon. The conversation was casual and involved the usual dance of questions such as “What’s the first thing you notice about someone?” and “What exactly are you looking for?” Two of the last things I expected to be asked were “Are you busy today?” and “Would you mind picking me up?” I was taken aback; her photos, messages, and overall profile suggested she was more of a reserved and “get to know you over the course of several dates before I bang you” kind of gal. I suggested an evening walk through a local park, and she gladly accepted my suggestion. I picked her up from her home about 5 hours later; she looked just like she did in her photos albeit with her hair in a bun rather than down.

The date was going well enough. No awkward silences, no misunderstandings, enough common ground, and a comfortable amount of vulnerability.

The conversation eventually drifted towards sex, and she revealed it had been only several months earlier in the year since her first kiss and sexual encounter. This is something I wouldn’t have expected given the way she expressed her hopes for dating while we messaged each other; she seemed to know what she wanted (no FWB, no one night stands) and that suggested some amount of experience to me.

We end up in an alcove in front of a fountain in one of the park’s gardens and chat about life, the universe, and everything. The conversation goes silent, but it isn’t an uncomfortable silence. It’s the silence that makes you feel like it’s gonna storm. You can’t see it, but you can feel it, this, electricity. It’s a silence that I, sitting next to Edith and gazing at the garden and the lights strung above, would be a fool to interpret as anything other than a signal to progress past words. I know we’re on the same page when she breaks the silence by commenting that this stone bench in the alcove of the garden is a perfect make out spot. I didn’t expect her to be so forward.

Our arms wrap around each other, we pull each other close, our eyes close, and our lips touch. It’s readily apparent that she had her first kiss just several months prior. I give her a few pointers and she’s still a bit awkward in her movements, but she’s definitely getting the hang of it. This snogging session lasts maybe 7 minutes before we stop to take in the moment. She comments “Great, now I’ll be horny for the rest of the night.” I shoot my shot and tell her she’s welcome to come over. She doesn’t hesitate to say that’d be a great idea.

By this point, you’re probably wondering when the fuck I’ll get around to the reason why you navigated to this subreddit in the first place, so I’ll tell you that we arrive at my place, make our way to the couch in front of the television, watch one episode of Bojack Horseman, and make it through about the first 5 minutes of an episode of Arrested Development when I ask her if she’s ever tried spooning. She hasn’t. I ask if she wants to be the little spoon or the big spoon. She chooses to be the little spoon. Our bodies are pressed against each other, my arms are wrapped around her, and it doesn’t take long before I start to exhale forceful and hot breath down her neck. Her diaphragm contracts and expands heavily and significantly more dramatically than it already had been. The hand of my top arm makes its way under her shirt, glides up the skin of her abdomen, and slides underneath the cup of her bra to hold and squeeze her breast for the first time. It’s somewhere between small and medium (I’m not familiar enough with cup sizes to be more precise), and her nipple is just a tad smaller than the tip of my pinky. She’s sensitive and shudders at this first touch. Keeping in mind her inexperience, I take my time while I pull my hand back out, lift up her shirt, unhook her bra, and move back under the front of her shirt to give equal attention to her other breast. Her breathing becomes heavier. I pinch her nipple lightly with my top hand as my bottom hand starts to grip her throat as we remain spooning on the couch as police dogs descend upon George Bluth in the Aztec Tomb.

Soon enough, my crotch is grinding against her ass. There’s no way she doesn’t feel my bulge growing and hardening against her. My top hand moves from playing with her nipple and squeezing her breast to sliding over her jeans and between her legs. Her crotch is warm, and even through her jeans, I can tell she’s getting wet. My hand moves back up under her shirt towards her midriff then back down under the waistband of her jeans and underwear. She hasn’t shaved. My hand slides lower. She’s so wet. My fingers glide right across her clit and down her slit. She gasps and moans; I can’t help but think she was hoping for this since she told me back at the garden she’d be horny for the rest of the night. I lightly rub my middle finger in a circular motion on her clit and elicit a quiet, breathy “Oh my god” every second. This isn’t enough for me, and maybe isn’t enough for her. We need to go deeper. It’s a seamless transition from the top of her clit to the beginning of her lips and the wet, hot opening of her pussy. My middle finger slips right in and is immediately coated with her natural lubrication. I breathe even more heavily into her ear, kiss it, suck on it, slide my tongue between its ridges, and suck and kiss along her neck. I want to overload her senses. I want her to know what intimacy can be. I plunge my finger as deeply as I can from a spooning position and use my newly soaked finger to tease her clit whenever I slide my finger back out.

This can’t go on forever, so I ask her if she’d like to move to the bedroom. She follows me until we’re standing next to the edge of the bed. We wrap our arms around each other and embrace as our lips interlock. I spin her until her back is facing the bed, and I push her backwards as I follow by falling forward as I prop myself up with my hands and arms. We kiss more in that position before I move to realign us so that we move from lying horizontally across the bed to vertically. She rests her head on a pillow, and I ask her if she’s ever undressed someone before. She says she hasn’t, and I guide her through the motions; I instruct her to grab my shirt from its bottom hem and pull it up towards and over my head. Her shirt and unhooked bra follow suit. I help her take off my pants. I slide off her jeans. We’re entwined with all but our underwear removed.

I position my body between her legs, my crotch against hers, and slide down to have my face hovering above her chest. I take her nipples in my mouth. I test the waters by flicking them, swirling my tongue around them, nibbling them, and eventually biting them firmly as she gasps and moans. I slide my face up towards hers to lock lips with her for a few more moments before moving to bite her neck, play with her ears, kiss along her clavicle, and trace a path between all of those spots with my tongue. I ask her if she would take hair out of her bun and let it down so I could run my hands through it. She was already cute with her bookworm look, but with her hair down and glasses off, she looked like a total sexy and sultry vixen.

My mouth makes its way back down to her chest where I give more time and attention to her breasts before kissing down the middle of her torso down to her pussy. Her panties are still on, so I sit up on my knees on the bed to lift her legs up, grab the waistband with both hands by her sides, and slide them up and towards me to reveal a completely natural and untouched bush. She’s bashful and tells me she hasn’t shaved because her skin is sensitive, and acknowledges that some men prefer a clean-shaven pussy. I reassure her by telling her it isn’t the first time I’ve seen pubic hair and that I don’t mind any degree or absence of a bush. I ask her if she’s ever received oral. She replies that she hasn’t. I dive headfirst between her legs to taste her, determined to make her first experience one to remember. I start by lightly running the tip of my tongue up and down her clit then circling it in slow, methodical circles. She tastes and smells so sweet; I can’t get enough and am turned on even more by the fact that I’m the first mouth to taste her. Her breathing is heavy, and her speech is a quiet, breathy stream of one repeated phrase, “oh my god.” I switch my focus from my tongue on her clit to my tongue sliding up and down her slit. Her labia is absolutely drenched and my tongue is coated with her taste as I penetrate her with it before sliding it back out. I move my tongue back to press hard against her clit as I move the tip of my tongue in a fast, forceful circular motion. I trace the alphabet with my tongue against her clit. I simultaneously slide my middle finger inside her and curl it upwards to massage her g-spot. Her legs begin to tremble. I flick my tongue quickly back and forth horizontally across her clit as I slide my index finger inside her to join my middle finger, alternating which finger I curl upwards. I look up at her face while I’m between her legs, and I see her looking back down at me with her eyes barely open and fluttering as she holds her mouth agape. Her moans become louder and I feel her pussy spasm. Her legs are shaking now. She goes silent then starts gasping as she climaxes. I slow down and uncurl my fingers as I transition to gently fingerfucking her. Her legs slowly relax and her moaning returns as my soaked finger slide in and out of her.

I give her a few moments to soak in the aftermath of her orgasm before taking the lead again to ask her if she’d like to take my cock in her mouth. She gladly obliges and moves between my legs as I go to lay on my back with my head on a pillow. I slide my boxer briefs down, my dick springs out, and she gingerly takes it in her mouth. I can feel her teeth lightly grinding against my shaft, so I give her more than the one tip and soon enough she has her tongue and lips gliding slowly up and down my shaft. Most likely because of my previous partner, I’m not expecting her to go more than a third of the way down my shaft, so I’m (more than pleasantly) surprised when this sexual newbie swallows two-thirds of me without struggling to or gagging. I lift her mouth up off of my cock to ask her if she has a gag reflex. She says she does, but she doesn’t know how sensitive it is. Of course, the only way for me to find out is by grasping the back of her head with one hand while I hold her hair in the other and start to slowly push her mouth down back onto me. She engulfs about 80% of me before it seems there isn’t more progress to be made for now (to her credit, she still hasn’t gagged). She starts bobbing her head up and down; it’s a bit stop-start, but it feels amazing and this blowjob seems to be going more smoothly than they had gone at times with Naomi. I give her tips on swirling her tongue around the head and shaft, and I show her how to stimulate my head while using her head to stroke my shaft. I ask her how I taste to which she responds “Good, but I want to feel this inside me.”

Say no more. I sit up to spin and push her back against the bed. I spread her legs open and take in the sight of my new, bashful, horny, and inexperienced lover. I reach towards my nightstand drawer to pull out a condom. I slide it onto my cock and position myself above her, face-to-face, cock-to-pussy, and use my hand to guide myself inside her. There’s absolutely no resistance, and her eyes begin to flutter again as she begins to let out another breathy repeated stream of “oh my god.” Her legs are spread open as I slowly thrust into her and feel her warmth enveloping me. I could only go so deep with my previous partner, so it was amazing to feel no resistance as I continued to push deeper into Edith’s pussy. I’m fully inside her now and hold myself there while I watch her face, lips parted halfway and eyes beginning to open to meet my gaze. I lower my lips down to kiss her as I pull my cock back out before sliding it back in to establish a slow, steady rhythm. There’s only the sound of our breathing, the sound of my cock spreading and entering her wet pussy, and her repeated “oh my god” as we let ourselves melt into this shared experience.

Her walls feel so fucking hot and wet and….good around my cock, even with a condom on. I quicken my thrusting and start to take even more control by grabbing her legs and resting them on my shoulders. This was absolutely not something I could do with Naomi, and that made it all the more exhilarating when I realized I could still probably go deeper. Edith’s eyes were barely open now as the sloshing sound of my cock thrusting in and out of her soaking pussy continued. With her legs on my shoulders, I began to press my body down against hers so that her legs were being pressed down towards her chest. Still no resistance and still no cries of pain or discomfort. I angled myself so that the head of my cock rubbed against her g-spot. At this point I was pounding Edith, spurred on when she switched from her repeated “oh my god” to “fuck me, please fuck me.” My legs were straightened out and I was balanced on my toes as I would be in a plank; I was lifting myself up before slamming myself back down into her wet, hot, and hairy pussy. I pick up the pace as she continued moaning as we pressed our lips together to kiss every now and then. Eventually I’m hammering her, and I start to feel her legs tremble again. She starts up again with her stream of “oh my god,” and as I continue fucking her it becomes more rushed, more urgent, more choked up, as she starts to reach her second climax. I can’t take it anymore, and I start to feel the pressure and tension building in my cock. Her legs start to shake, she moans, I plunge myself as deeply as I can inside her, I groan, and shoot my load into the condom while her vagina is fully enveloping my cock. My body collapses on top of hers and we lay there for a few minutes, breathing and soaking in our post-orgasmic bliss.

I prop myself back up on my arms and slide out of her while holding the base of the condom. We took care of the usual post-coital business that not every sexy story includes (cleaning up with tissue and/or wet wipes, tying up and throwing away the condom, peeing to prevent UTIs, etc) before settling back onto the bed to cuddle before driving her back home. She tells me that I had just given her her first two orgasms. Ever. Masturbation included. I tell her I’m honored to have given her that experience, and I honestly do feel that way. I had definitely made an effort to make this a good sexual encounter and a night focused on her because she told me she was inexperienced, but I had no idea I was taking her into uncharted territory.

That was Sunday, and it’s Tuesday now. We texted on and off during Monday.

“I’ve been thinking about yesterday and I’m totally wet lol”

“Would it be too soon to ask to see you again today? Lol”

“Thought I’d let you know that I’m fingering myself thinking about you”

“I was thinking about when you went down on me and I had my first orgasm. I don’t know what you did with your tongue and fingers but I want to feel it again. And then when you put your dick inside me it felt soooo good. I want you to fuck me again. Oh my god please fuck me again”

“Will you fuck me again?”

“Oh my god I want you touching me all over my body”

“I want everything”

“A girl has needs and you have a nice dick so yeah haha”

Turning out this shy bookworm could be fun.

Source: reddit.com/r/gonewildstories/comments/drygyx/my_first_time_giving_a_girl_her_first_two_orgasms