When she asked me to be her first time [MF]

(My writing is always long, so I’ve used +++++ to denote where sexy stuff starts, and ======== to denote where sex itself starts. It’s a cute story though, so hopefully the context adds to it.)

A few years ago, in the months between the relationships mentioned in my last two stories, I felt kind of unreasonably lonely. I had a solid group of friends, but the folks in the department where I was doing my masters weren’t that sociable and most of my friends from other departments were in serious relationships. I’m too extroverted for a cozy party every other week to be sufficient, so I basically became that guy who uses multiple dating apps. I think my experience there was kind of unusual, because the main reason I was using four of them (Coffee Meets Bagel > Hinge > Bumble >>> Tinder, if anyone looking for an actual relationship wanted suggestions along those lines) was just that it was hard to find people weren’t either ego swiping or trying to evaluate people for hookups. To be clear, I’m not using the latter to describe people who swiped left on me. Everyone’s got their own tastes, and that’s completely fair! Rather, it’s the people who swipe, expect you to carry everything, and go silent if you aren’t being the most entertaining person in their DMs at a given time. Really not a fan of having my time completely wasted, even if it’s only 20 minutes per ego match.

However, more weekends than not I had a date scheduled, and that was really most of how I got the socializing I needed to be emotionally healthy. Even with the ones that didn’t seem romantically promising – and were mutually understood to be such – we would often just plan more times to hang out platonically because the company was fun. It’s usually more fun to hang out with people you know, but most genuinely friendly people are a delight even if you don’t know each other yet.

One of the first dates in that period was with a woman who was working for a high-end food company as a biologist. While a lot of places would mainly use flavor chemists and stuff like that to make their crackers optimally addictive or whatever, this place’s whole brand was built on things having no artificial chemicals. So her work was on using genomics combined with focus group research – or something like that – to figure out which plants they should cross-breed to make better fruits, vegetables, and wines (though the wineries themselves were far away). Basically using Darwin and Mendel to do the same kind of thing as the flavor chemists at a lot of places, while catering to a very bougie market.

Divya was this petite, clever, and bubbly woman (yeah, yeah, so what if I kind of have a type) who’d grown up in LA and left for college to study biology. After graduating she’d recently moved to the area where I was doing my MS to work at this food company, and as a young adult in a strange part of the country was now experiencing the same kind of loneliness as me. We clicked immediately, and by the end of a first date the second (and third, I was already ready to bet) were pretty much guaranteed. The dates went from coffee, to lunch, to dinners, and we continued loving being around each other. However, I wanted to take things slowly, and conveyed this to her on the third or fourth date. I was just a couple months out from a serious relationship, and while I absolutely wanted to continue getting to know her, I wouldn’t be ready to make anything official for a while. She said that was totally fine.

Fast forward a couple weeks, and we’re at my apartment watching a movie on the couch. I don’t remember what it was, but knowing me it was probably some historical drama too intense to be any semblance of a good date-night movie. She snuggles up next to me, and it’s just a really cozy evening. As an aside, folks who read the last one may be noticing a pattern which I only just realized: small women seem to really like nestling themselves up against my much larger frame. Hooray for never fitting on airplanes… or a lot of chairs and desks… or certain stairwells…

Anyways, the movie is continuing, and I’ve got my arm around her shoulders and am playing with her hair. I always ask before doing that, not just because I don’t want to do something they’re uncomfortable with but also because even among those who like it some prefer gentle hair touching and head rubbing, while others love it so much that concerns about the effort needed to keep long hair groomed. Shoutout to the ladies who can manage that. If I were y’all, I think anything beyond a pixie cut would have me raging every time I had to style it or anything. Divya was one of those with long hair who preferred the “fuck it staying pristine, I want those head rubs,” approach. As the movie progresses I sort of lean slightly over against the pillows by the arm of the couch, and she’s resting on my chest as I play with her hair and rub her head.

At this point we’re just chatting, and the movie is largely ignored. Divya sits up, slowly but unexpectedly, and turns to face me. She smiles, then places her hands gently on each of my cheeks and says “How the hell are you single? You’re so fucking handsome.” I was completely flabbergasted. While I know I’m not actively unattractive, if I’m at all attractive as an adult it’s via a colossal case of ugly duckling syndrome. Past partners had made some offhanded comments, or maybe a hint or two that they thought I was good looking, but I never realized that could be part of a relationship for me. As I’m just kind of stunned and unsure what to say, she climbs on top and kisses me. Divya had this very specific smell, and I’d never experienced it that close before. My imprecise recollection is of something like a sweet-smelling but mild mix of ginger and vanilla, but I don’t remember for sure and never asked what perfume she used, so at least for me that information is lost to time.

After that first kiss, she pulls back a little, and I can see that as the impulse passed she’s feeling unsure if she did the right thing. I tell her again that I’m not ready for anything serious just yet, and she tells me, “That’s okay. There’s no rush,” continuing to smile at me sweetly. I look up at her, nod with a smile of my own, and place my hand on the back of her head to gently pull her back in for another kiss. We just kept going, and it wasn’t even like making out or anything. There was no urgency or French kissing or anything that, just a really intimate moment we were both savoring. We just held each other and kissed. At some point the movie ended, and the dimming of the screen to the credits made us both realize how much time had passed. It was late, and she needed to drive home, so I walked her back to her car. Before she climbed inside, she planted another kiss on my lips and asked if she could come over the next evening. It was a Friday, and the following week wasn’t too busy for me, so I told her I’d love that. I walked back into my apartment with a heart metaphorically made of the wrong state of matter, but of all the things to have melt, I didn’t mind that one bit.

The next morning I’m headed to the grocery store, and I text her to ask if there’s anything she’d like me to make her for dinner. I warn that I’m nothing amazing in the kitchen, so anything technically challenging is a bad idea, but I’ll do my best if it’s something I think I have a real shot at. I don’t remember what she picked, but that evening I either did a pretty decent job making it or she is an amazing and unnecessarily kind liar. During dinner we’re talking about books, and she asks what some of my favorites are. I list a few, and one of them turned out to be a book she’d been curious about for a while but wasn’t sure if she wanted to take the time to read. I tell her I’ll go to my room and grab my copy for her to borrow, but before I get all the way out of my chair Divya stops me. She pauses for a couple seconds, then asks if I would read it to her. Being read to was a big deal to her as a kid, and she hadn’t gotten to experience it in over a decade. “I’d love to,” I tell her, my heart melting all over again.

I had expected I would just head to my room, retrieve it from my bookshelf, and return to read it to her on the couch. But when I turned away from the bookshelf next to my desk, she was standing right behind me. I smile, and since I’m assuming there’s a reason she followed me into my room I ask where she’d like to cuddle while I read to her. She shrugs kind of bashfully, and asks if my bed would be okay. It’s more comfortable than the couch, so I have absolutely no problem with that. My bed was on a pretty high frame because I like being able to use the space under it for dressers and other storage. With my height, it’s no issue at all to get up onto the bed despite the elevation, but at barely 5′ tall that’s rather challenging for her. When I notice she’s having a hard time, I hop back off the bed and offer to help her up. “Okay,” she tells me, then guides my hands to her waist. I tell her to give a little jump, and provide the rest of the boost she needs to comfortably and safely get up onto the bed. I hop on after her, and barely a minute later she’s snuggled up against me just like the night before.

I crack open the book (“All the Light We Cannot See”, for those looking for a really moving piece of historical fiction), and start the story. I get really into reading to people, and so it takes a lot of focus. I try to maintain consistent and distinct voices for important characters, and maintain a cadence that I’d expect from a good audiobook. Because of the concentration required, I’m ignorant to everything but the reading and the warmth of her body against mine. Out of the blue she places her hand on the book to push it down, then kisses me just like before. It’s the prior night all over again, gentle and sweet… at least at first. Quite unexpectedly, I feel her tongue slip up against mine, and things quickly become more intense. She climbs onto my lap and places her hands on the sides of my head to sort of hold me in place for easier kissing, and my arms are wrapped around her slim waist. We continue for a while – no clue how long – until she pulls back a little to stare into my eyes again.

|+ + + + + + + + + + + +

“I…” she starts, “I want to ask you something.” I tell her of course, ask away. Divya explains that growing up with very traditional Indian parents, she didn’t date anyone in high school, and her relationships in college were kind of muddled by the difficulty of getting out of the mindset she was raised in. She’d had serious boyfriends, but hadn’t ever wanted to be physically intimate with them beyond the kinds of things she and I were already in the middle of. I started to reiterate that it was completely fine if she wanted to wait, and that I was still in absolutely no rush, but she stopped me partway through.

“I want to have my first time with you,” she told me, glancing away before looking back straight at my face earnestly. I smile back warmly, and ask her if she’s sure. She says she is, but that it needs to be slow because she doesn’t know what to expect. I tell her explicitly that things will go at exactly the pace she’s comfortable with, and that they can pause, slow down, speed up, or stop entirely whenever she’d like. She nods, her face a visible mix of nervous excitement. I ask if I can take her shirt off. She nods again, nervous but more firmly. My hands slide against the waist of her jeans, then up under her shirt to touch bare skin. Divya yelps a little, and I pull back to ask if she’s okay. “Your hands are freezing!” she giggles, making an exaggerated shivering motion. I smile and chuckle back, then suggest we cuddle under the sheets for a little while, “so I don’t give you frostbite.”

We’re in that warm little cocoon (well, little compared to me. Any bed that could physically fit me would have inevitably been quite roomy for a person Divya’s size), and we’re holding each other’s hands, “to warm them up faster,” she’d insisted. Once she decides they’re sufficiently tropical rather than arctic, I slide them back to the smooth, bare skin under her shirt. I don’t know anything about fashion, but I wish I knew the term for this shirt. It was kind of loose and flowy at the waist, but form-fitting in the shoulders and upper chest. Opaque fabric, but thin, soft, and almost wispy. Whatever it was, all night I’d been loving how it looked on her, but I was even more excited to see underneath.

Divya was very petite, and I think her boobs would probably have been an A cup. I’ve never been a “boobs” guy in the traditional sense, in that I’m more the sort to be an ardent supporter of the “itty-bitty-titty-committee”. The covers aren’t completely covering us, and the lamp beside my bed provides good lighting, so as the shirt comes up and off I’m just admiring the shape of her. Her skin had a softness to it which so suited the rich brown color, and there was a rhythmic and visible rise and fall to her chest as she breathed a little heavily in excitement. I’m sure I was doing the same. I toss her shirt towards the foot of the bed, then run my hands gently along her side. We kiss again, though it’s very much not the innocent sort from earlier that evening and the night before. I ask if she’s still feeling comfortable, and she replies “yes” with a smile and a firm nod. My kisses then drift down her neck, her collarbone, until my lips are on one of her nipples. They’re poking out, almost as though asking to be played with, and so I start running my tongue around each, moving back and forth slowly and periodically. Her fingers are in my short hair, and I wrap an arm behind her to gently place a hand on her ass. That hand then drifts around her hip towards the front, and I unbutton her pants. She grabs my arm, and I stop immediately to look up at her.

“Everything okay?” I ask. “Yes!” she replies to reassure me, then pauses before saying, “Would you be willing to finger me?” I smile widely and tell her of course, and that I’d love to. Her eyes are glittering with excitement, and while there’s still some nervousness on her face, that nervousness is starting to go the way of an ice cube sitting in the sunlight of a Florida summer afternoon. The zipper slides on down, and now I’m slipping her jeans off her hips and down her legs. There’s something special about a beautiful woman who’s completely naked save panties and a pair of ankle socks. I know knee-high or thigh-high socks are the standard fetish, though I don’t think I would call my feelings on this a fetish, but it just “hits different” for me, so to speak. As she kicks gently to help me get her jeans off, I get this sense that we’re both looking at each other practically like a pair of kids in a candy store.

I suspect the reason I tend to be most attracted to petite woman, and the reason they’re definitely overrepresented among people who express interest in me, is that the difference in heights and body sizes let me feel like a protector, and lets them feel protected. I may well be talking out of my ass with regard to how they feel about the size difference in general, but that was the explanation I got from one woman I dated. Whatever the reason, seeing Divya laying on my bed, her small frame silhouetted against the medium green of my sheets, was just heavenly. It’s not the only time I’ve felt that, and she’s not the only one I’ve felt it with, but when it happens the feeling is essentially impossible to really put my finger on. Speaking of putting my finger on things… (this joke is probably fucking up my attempt to convey how that moment felt, but I couldn’t resist)

Now it’s time for me to resume those wandering kisses. I start with her lips, then slowly move down inch by inch until my lips are at the waistband of her panties – white, kind of dainty things. I slide them down and off. Whereas after the jeans came off she still had her legs spread wide – though not exaggeratedly so, now she has her knees closer together. I move back up to kiss her, and ask if she still feels comfortable. She tells me that she’s nervous, and I remind her we can slow down or stop any time she wants. She looks at me, and tells me it’s okay, then goes quiet for a bit until she said, “Can you still finger me?”

|= = = = = = = = = = = =

“Don’t need to ask me twice,” I reply with a grin. I continue kissing her, and reach one hand down to gently stroke the skin previously covered by her panties. I move my fingers down to her inner thigh, and then slide them over her slit. She wasn’t shaven, but I couldn’t care less as long as it’s groomed enough that I won’t end up picking hair out of my teeth if I eat the woman out. For fingering it doesn’t matter at all, but she was also trimmed enough that there wouldn’t be any problem regardless of how I was helping her get off. The first several times I sleep with someone, I always try to operate under the assumption that they won’t be anywhere near as wet as I might immediately think. That’s not usually the case, but there’s no harm in being a bit more careful and I don’t want to hurt someone I’m sleeping with by accident because we rushed. Also, lube is great regardless, and having a bottle of it in my nightstand at all times might be the best “pro-tip” I could give anyone of either gender. I <3 lube.

Anyways, this was one of the times where I substantially *underestimated* how wet the person I was with had gotten. That momentary brush with her labia left my fingers dripping a little, and I’d be lying if I said that didn’t make my boner “grow three sizes that day”. I start working on her clit, asking what feels good and what doesn’t, how much pressure to apply, which sort of movements work best, and so on. Divya is blushing, her toes curling a little, and even with her eyes closed she’s still smiling in between making those sorts of “O” faces that often precede an orgasm. I bring my other hand down and start sliding a finger inside her gently, keeping the first hand busy with the preferences she’d expressed regarding her clit. I’m making sure to go very slowly, using my index finger to stroke inside her and only moving deeper with caution. Admittedly I still don’t know exactly why, but I know most of the women I’ve heard talk about this (in person or online) have described their first time as horrific. I knew I probably couldn’t make it mind-blowing, but I sure as hell was going to make it as good as I possibly could for Divya. Whether or not things worked out between us, I wanted her first time to leave her knowing that her pleasure is absolutely essential. Once again she grabs my wrist, and I pause immediately to ask what’s up. Of all the things I thought she might have been about to say, it was not what followed.

“I don’t think you’re going to hurt me – though I’ll let you know if it does! I’ve used toys before and… you don’t need to be that gentle, okay.”

“Are you saying you want me to be rough?”

“Not super rough, but definitely at least a bit.”

I smirked, kissed her, and set to work. There’s not much to tell about the next few minutes which wouldn’t be a repeat of what I’ve already said, but soon enough the ratio of time spent smiling to time spent in an “O” face is leaning more and more towards the latter. I suddenly feel her shake, and she grabs hold of my bicep. I had a momentary fear that it was her telling me to pause, but with the look on her face the past few minutes I decided I would continue but keep a close eye for any signs of distress just in case. As it turned out, it was purely eustress – of the orgasm variety. The trembling continues, but then begins to fade. As she comes down off the high, she… well… looked kind of high. Divya made a little giggle, then reached behind me to pull me in for a kiss. “How was is?” I asked between kisses.

“Really good,” she giggled again.

“I’m glad,” I replied with another kiss.

At this point Divya bit her lip, and I could see words starting to form. I raised an eyebrow, which I think she saw, and she blurted out, “I want you inside me.” I told her I’d be right back with a condom, and hopped out of bed to grab a few from my desk a few feet away. I place a handful on the nightstand – I wasn’t about to think through counting out a reasonable number – along with a bottle of lube, then climb back into bed next to her. Now it’s her turn to strip me, and pretty soon a t-shirt, boxers, and jeans of my own have joined the pile of her clothes at the foot of the bed. I open one of the condoms and roll it onto my dick, then ask which of us she’d like to have on top.

“I assumed it would be you,” she answered, almost quizzically.

“Do you want it to be? I’m happy either way, but I thought you might like to control the pace and depth and all that. That’s a lot easier when you’re on top.”

“I don’t really know what to do,” was the reply.

“Well, you could be on top and decide how fast and deep we go initially, then I could take over afterwards. It might make things easier for you, but then I can still take the lead if you’d like.”

She agreed enthusiastically, and soon I was on my back and helping her navigate the head of my dick inside her. Wide-eyed as the tip slowly split her open, her intense look turned to a gasp as she dropped herself down a little too fast.

“You okay?” I asked.

“Yup, just surprised is all. You’re big.”

I chuckled, and said, “I’m not sure what you’re basing that on, but thanks.”

She laughs sweetly back, then takes some time to slide herself most of the way up and down my shaft a few times. It’s clearly awkward positioning for her, so once it seems like she has a feel for the shape of things I offer to take over. A vigorous nod is all I need to see, and I lay her down across the bed on her back. Divya spreads her legs wide, and I position myself between them. As I’m positioning the tip of my cock between her labia, she reaches up to pull my torso closer. It makes things a little tricky momentarily, but once I’m inside her I can move my arms down on either side of her chest more easily and she gets to hold me like she wanted.

I’d love to tell you that I made her orgasm again from just penetration, but that didn’t happen. Thankfully, by all indications she continued to have a wonderful time too. This was one of those times where there wasn’t any changing of positions, fancy sex jiu-jitsu, crazy kinks, or anything like that. I’m definitely one to go for all that stuff (minus the sex jiu-jitsu. Though if playfully combining MMA and sex is your thing, I can definitely understand how that could be very fun), but I just wanted her to feel safe and to enjoy herself. Plus, it having been a particularly slow burn had left me incredibly turned on as well. I certainly wasn’t being as gentle as I would have been without her earlier request, but at least initially it was still slow, rhythmic strokes. Soon enough, my brain just automatically starts slipping into the habit of progressively increasing the speed and intensity, and before I even noticed it she said, “Yes! Harder!”

Between how petite she was and this being her first time, I had the entirely ridiculous fear that I would break her or something. As a result, the change to “harder” wasn’t anything significant. When she realized I wasn’t understanding how serious she was, she placed her hands on my cheeks just like she had the night before. At this point it felt so bizarre to think it was only 24 hours since that first kiss. Her hands are on my cheeks again, and she’s smiling at me, but there’s a hint of sternness to it this time. “Worlds_dumbest_docto,” she whispered, “I want it harder.” I got the message that time.

I’m moving far more than before, far faster. Her arms wrap around my back and neck to pull me in tight, and at that point the only option I have is to do it all with my hips. I’m thrusting harder – not nearly the force I’ve used when asked for it in more established relationships, but apparently still enough to fulfill the request. I can hear her gasping, and I’m breathing faster and faster myself.

“You feel amazing,” I whisper into her ear fiercely.

“Oh god… you too…” she moans out.

It’s only a moment more before I’m thrusting deep and filling the condom. I later found out she was on birth control, and if we’d been dating, or at least known each other at that point, odds are all that sperm would have gone straight up into her womb. As intense as my fetish for that is, the thought didn’t even cross my mind that evening. We’re tangled up in each other, doing that thing where it’s a mix of breathing heavily and soft but contented laughter after you’ve just had really good sex. I kiss her, and tell her I’m going to throw the condom away but that I’ll be right back. She nods, and I slide back out of her. I see a puddle in the sheets as I do so, and for a brief moment panic thinking the condom might have broken. Nope, fully intact and quite full as well. Then I realize it’s just how wet she’s been this whole time, and I felt like a total stud in a way I’d never experienced in my entire life up to that point. I tossed the condom in the bathroom trash, and quickly washed my dick. I don’t know if it’s actually true, but I was once told to do it just so that if there’s a round 2 you don’t have to worry about the cum on your dick sliding over the new condom, or the whole condom sliding off now that you’re lubed up with your own semen. Once that was all set, I grabbed a towel that was clean but not super nice and headed back into my bedroom. I climbed back up beside her, and offered the towel in case she wanted to clean herself or wanted me to clean her. Apparently it was the latter, so that turned into a kind of… postplay? There’s probably a word for it, but it was like extending the physical intimacy beyond the sex itself after the fact, rather than in the lead up. We fell asleep in each other’s arms, and in the morning I woke up to the warmth of her naked back pressing up against my bare chest.

It didn’t work out in the long run, because well before I felt comfortable with anything serious she flatly insisted on it being official. I wasn’t ready and didn’t want to waste her time, and so she decided it wasn’t a good fit. I respected the decision, and cross my fingers that she’s ended up very happy with someone who was ready to give what she needed. While that’s absolutely the main thing I wanted for her, to this day I still hope her first time is a happy memory she can carry forever.

Source: reddit.com/r/gonewildstories/comments/sj8s27/when_she_asked_me_to_be_her_first_time_mf