First Time Experiences

[NSFW: Explicit Sexual Content]

[A/N: This became a lot longer and more detailed than I had originally intended. I was struck with the idea of writing about a couple’s first time having sex where one’s an intersex woman (Charlotte uses she/her), and one’s a cis woman whose only previous experience is with other cis women. That ended up turning into all this. Once I saw how long it was getting, I realised at that point I was only writing for my own satisfaction. There’s also some retrospection early on (marked with ~ signs), so I hope the tense changes don’t confuse you. But if you get through it, I hope you like it.]

“Are you really sure?” she asks me, and I smile gently at her. Part of me wishes she’d stop asking, but even though I am definitely nervous, she seems to be even more so than me. Typically she’s the more confident one.

“Yeah,” I say to her, and put my hand behind her head to pull her into a kiss. My tongue slips in without resistance, and I hold her for a moment. “Are you?” I ask back, and I can see in her eyes how she’s thinking it over.

~Back when I asked her out, I could tell right away that she hesitated. I wrote it off as just a natural reaction to a girl she barely knew asking her out. We had talked a little, but I really only knew her as the cool, competent, mature woman at work. She always seems like she can do anything. Falling for her was easy. Learning that underneath that exterior she can be just as insecure and troubled as me was both a relief and a disappointment.~

“Yeah,” she tells me. We have discussed this several times, and finally hit a point where we both feel we want to go for it. I cup her cheek with my hand and stroke it gently with my thumb.

“Just let me know if you change your mind, and I’ll do the same,” I say. We already said the same before we started, but I don’t think it hurts to repeat it. She nods, and nuzzles against my hand. The way she smiles at me makes me feel a bit better. She starts cautiously touching me, and I can feel my body tingle wherever her fingers make contact.

~After we started going out she kept some distance between us. It took me a little while to notice, because I didn’t expect we’d get that close until after a little while anyway. But I think she was always conscious of it, from the very start. I haven’t felt like asking, but I wonder if she’s had some bad experience in the past.~

I raise my arms to let her take my top off, then I return the favour. She is quite beautiful. She tells me I am too, but if so I’d say it’s in a different way. I always feel like people are judging me for being with someone so pretty when I’m so ordinary-looking by comparison.

~It took about three weeks before she told me. At first I felt upset that she hadn’t told me right away, but the look on her face made me feel bad for even thinking that. The usually calm and confident Charlotte was on the verge of tears. Shaking like a leaf. I think she was certain that I was going to break up with her over it. Or worse. She still cried when I didn’t. From relief or surprise, I think. We held each other for a while afterwards.~

As for me, I have never been with anyone like her. Or anyone with a cock. Today will be my first time seeing one in person. So yeah, I’m nervous. I’m just trying to hide it for her sake.

I ask her to turn around for me, and I undo her bra before I embrace her from behind. She has such wonderful breasts. They fit my hands so well, and she makes such lovely noises when I caress them. I reach down to undo the buttons on her jeans, and I feel her freeze.

“You okay?” I ask, and stop my hands on her stomach.

~After she told me, I realised she had been avoiding having her crotch come in too close contact with any part of me as much as possible. She still kept doing that after I knew, even though I tried to tell her it was okay. Perhaps I wanted myself to believe that as much as I wanted her to. We have fooled around some, but stayed away from each other’s crotches.~

“Yeah, I’m fine… sorry,” she says after a moment. Maybe after tonight she will feel more comfortable. If everything goes well. I love her. I think she loves me too. She is very cool and collected most of the time, and very sweet when we’re together. Very attentive and thoughtful. Likes to tease me. I’m not sure she is fully aware of how charming she is.

“You don’t have to be sorry,” I tell her, and lightly kiss her neck. “Do you want to stop?” I ask. We can always try another time.

“No, I… please… k-k-keep going,” she replies, and I squeeze her gently against me. I’m not sure I deserve her, but I don’t intend to leave her so long as she doesn’t want me to.

I move my hands again, and pop the buttons open. I can feel her cock under there, bulging against her underwear. Even though I could tell she was serious when she told me, it’s been hard to actually believe it. Until now. Until I could feel it.

My hands can’t help brushing against it while undoing the buttons, and she jumps at the touch. I stop my hands again, but before I can say anything, I can feel her hands sliding over mine, and guiding them to push her jeans down.

I crouch to push them all the way down, and she steps out of them. Then she turns around as I stand back up, and she looks so bashful I have to smile. Yet she reaches out, and this time she’s the one who pulls me into a kiss. Her tongue feels very warm in my mouth. I place one hand on her butt, and one on her back. It is pressing lightly against me down there now.

I worried beforehand that I was going to freak out if that happened, but I think I’m doing okay. She undoes my bra far easier than I did hers. I’m not sure if she’s practised, or just a natural.

She hooks her thumbs inside the lining of my slacks, and starts pulling them down. I step out of them, and feel a little embarrassed at how she can look right at my knickers now. Can she tell I’m already a little turned on? Does it show?

At least she doesn’t make any comment on it, and I steal another quick kiss once she stands back up.

“Is it okay if I go first?” I ask her. A combination of curiosity and not wanting to wait too long drives me. She hesitates, then nods. “Could you sit on the edge of the bed?” I smile in what I hope is an encouraging manner.

She does so, and I move to take her knickers off. It’s impossible to not see the bulge now, and I swallow from both nervousness and anticipation. I feel her freeze again as soon as I touch her hips, and I look up at her.

“Should I s-” I start to say, but she shakes her head, and relaxes again.

“Go ahead, I’m just…” she says while blushing quite heavily. “Just feeling… very… self-conscious,” she confesses, and I giggle a little.

“Well, I’m glad you feel okay telling me,” I say, and grab the lining of her underwear. She lifts her hips, and I start pulling them down. Only to quickly find I sort of have to unhook it around her cock. I’ll have to remember that for next time. … next time. I’m already jumping ahead here.

She slides further up into the bed when I’m done. I guess she’s more comfortable that way. I get onto the bed with her.

“Still doing okay?” I ask as I get between her legs. She nods at me.

“Yeah,” she says. “A little embarrassed I guess.” She smiles, and it really does make me feel better whenever she does. I look down at her crotch. She seems to be just like me underneath, and above there’s her cock. Her very real cock. So that’s what one looks like, huh? I thought it would be a little more… I don’t know. I slide down a little to get closer, and reach out a hand towards it.

“Can I?” I ask as I’m close to touching it. She has tensed up.

“Yes…” she replies and relaxes a little again. I touch my fingers to it, and she gasps. The cock stiffens and grows a little more. I guess it’s not done. I was wondering whether it was supposed to be more… more. I carefully put my hand around and grab it, and I feel it firming up even more in my grip. Such a strange sensation. It’s certainly more like what I expected now, but how big is it going to get? Well… now what?

“Um…” I say sheepishly, and look up at her. “What do I do… now? I have no experience with this,” I confess, and I think I’m probably blushing. I should have googled what to do. Gotten some tips at the very least. Why didn’t I think of that?

She’s smiling very patiently at me. Maybe seeing me freak out a bit is making her feel better about all this.

“Just… stroke it. Move your hand up and down,” she says. Right. I should have been able to figure that out. That’s obvious. Why didn’t I figure that out? I start moving my hand. “Don’t grip it too tight,” she tells me, and I nearly let go entirely. Wow, I’m worse at this than I thought I could be. Pussies are simpler. … maybe someone who’s never dealt with one wouldn’t think that…

“S-sorry,” I say, and try to get a comfortable grip. It is definitely very hard now. Is she getting turned on by watching me bumble about down here? I can’t imagine I’ve actually done anything that feels good yet, at least. “Like this?” I start carefully moving my hand again, trying to not drag or pull anything too much.

“Mhm…” she says, and lets out a small moan. “Keep going… a little faster…” I have a hard time believing I’m doing this right at all, but the facial expressions and sounds she’s making are very erotic. Should I do something with her pussy too? Or is that too much at once? Maybe I should focus on learning one thing at a time…

Looking at her, she’s so damn sexy right now. The way she’s squirming, and the faces she’s making. I’m feeling aroused myself just from watching her. Maybe she’s just reacting to how it feels different having someone else touch you. Maybe it’s been a while since she’s touched herself even. I don’t know what she does when I’m not around. Could I really be doing this right?

Her cock is such a strange thing, and it feels strange. Strange to me, at least. And really, really warm. It’s a little pinker than her skin. I… I kinda wonder what it tastes like… I stop stroking, and hear her let out a disappointed whine as she opens her eyes again.

“H-hey Charlotte?” I say, and she looks at me. It looks like it takes her eyes a moment to focus.

“Wha? Is… is it too… weird?” she asks me with a worried look, but I shake my head.

“No, it’s not that, I just…” Wow, this feels so embarrassing to actually ask. But there’s no way I could just do it without asking. She’s still looking worried, I have to just say it. “Can I… I mean… is it okay if… I… I taste it?” Oh wow, I probably could have said that better. Her eyes go wide.

“Er… um… you really don’t have to,” she says. I can feel her cock pulsing in my hand though.

“I-I know, but… I’m curious, so I… I want to,” I say, and it feels like my whole face is overheating. “If that’s okay, I mean. Please don’t feel like you have to… er… let me…” My brain may be fried, but I can hear her giggle.

“Sure,” she says, taking a deep breath. “But if you don’t like it, you don’t…” I nod, and try my best to return her kind smile. I’m sure this is scary for both of us, so I really appreciate her being patient with me. I don’t think I deserve someone as good as her.

“I know,” I reply, and start scooting down so I get close to it. “Thank you… you know… for… putting up with me…” I tell her, and she blinks a little at me.

“Ahaha, I could say the same,” she says, and reaches down to gently stroke my face. “I’m sure this is weird for you. I… think you’re doing great though.” I can’t tell if she’s serious, or just trying to make me feel better.

“That’s a little hard to believe since I have no idea what I’m doing, eheh…” I say with a nervous laugh. Heh, hard. “But you’re the one who would know.” And she did look really into it.

“Yup! And you can always trust me,” she declares. There’s that cool confidence of hers. “So please don’t worry about it.” She leans back and braces herself. Yeah, I should just trust her.

Now that I’m up close, that size of it seems a little more daunting. Will this really fit in me? It looks so thick. … let’s worry about that later.

I take hold of it again, and I can feel her twitch. It definitely has a smell of its own. I can feel it in there with the smell of her pussy. Which is more familiar proof of how turned on she is. I can also see something glistening at the tip. Taking a closer look it seems to be clear and sticky, and it’s dribbling out. Looks like some of it got onto my hand earlier. I guess I didn’t really notice with everything else on my mind.

I hold it up, and hesitate a moment. Why is this the part that feels like the point of the no return? It sounds like she’s just about to say something when I finally lean in to run my tongue gingerly up the side, catching some of the sticky stuff too. The moan she lets out sends shivers through me, and I can feel through her too.

It tastes… a little salty, but more sweet, I’d say. I expected it to taste more strongly, but it’s fairly mild. The texture of the cock against my tongue is a little strange, especially the head, but I wouldn’t call it unpleasant.

“Was that okay?” I ask, looking up at her.

“Yeah,” she says, swallowing hard. “Just di-didn’t think it would feel… that intense…” I’m not sure if that means I’m the first to do this, or if I’m just somehow that good. I don’t actually want to ask.

“Can I keep going?” I want to hear her make more sounds like that. She nods at me.

“Yes, but… ahm… be careful with your teeth…” she says with a deep blush. I am confused for a moment, before I realise what she means. I hadn’t thought as far as actually putting it in my mouth, but I can totally understand she might be nervous about biting.

I lean in to lick it more, and she rewards me with more of her erotic moans. With the way her cock is twitching, I feel like that means I’m doing it right. Probably. It’s certainly producing more of that sweet, sticky stuff. She seems to react the most when I use my tongue around the head of her cock. So what will she do if I take that into my mouth?

It’s not so thick that I struggle to wrap my lips around it. I hear her groan in a new way as I do that, and when I flick my tongue across the tip her back arches right up off the bed as if her spine was hit with a jolt. This is fun. Getting these sorts of reactions from her is really turning me on, and I’m glad I’m able to make her feel good.

I roll my tongue around a bit, and experimentally suck on the head. I accidentally brush my teeth against it, and I can hear her hiss. I’m going to need to practice the whole teeth thing. How much can I do this before my jaw gets tired?

“J-Jenny…” I hear her say, and I lift my head to look at her. “If you keep this up, I’m gonna c-cum soon… so you don’t have to…” She’s panting heavily, and it seems to be making it hard to talk.

“Charlotte… I want to do this,” I tell her as confidently as I can. “If you want to cum, I want to make you cum.” I can clearly see the arousal in her eyes, and it’s making me feel tingly all over. “But if you really don’t want me to, just tell me so.” I sit up a little so she can see my eyes properly. Hopefully she can see I’m serious. She looks away for a moment, then looks back at me.

“I want… I want you… to make me cum…” she says with a pleading look. Why is that turning me on even more? I smile at her, and then go back down to take her cock into my mouth again.

I still feel like I’m at the ‘trying to figure this stuff out’ stage, but I can tell she’s getting close regardless. That part remains much the same, as she’s making the same kind of sounds I’m used to. And I think the cock is swelling even further.

“J-J-Jenny, I’m… I’m about to…” I hear her manage to struggle forth the words. “You should…” I should? “Pull… out…” I’ve gotten so into my ‘practice’ I don’t realise what she means in time. Then she cries out, and I feel something hot shoot into my mouth. I reflexively pull back, and the next blast just barely misses my face as white stuff shoots into the air before splattering down on my hand and her crotch. Why is it so hot? I let go and the rest spurts onto her stomach.

I blink a little. So that’s what an orgasm from a cock is like. I think maybe some of it got into my hair. I check with the back of the hand that’s only covered in a bit of my juices. On reflection I maybe should have kept one hand clean, but in my defence I was really into it. Yup, feels like there’s some in my hair.

And what about the stuff that got into my mouth? It’s salty and kinda slimy, but I swallow it. That feels like the easier option rather than running to the bathroom to spit it out. I won’t say it’s necessarily pleasant, but I could probably get used to it. I mean, it’s Charlotte’s…

What a mess this turned into though. I think I can now say that pussy orgasms are easier to deal with. Or at least to clean up after.

“Ah! I-I-I’m so so-sorry Jenny!” Charlotte says, and I look up at her. Oh. She looks really ashamed. “I tried to h-ho-hold back a-and warn you, b-b-but…” Oh no, I think she’s about to cry.

“Charlotte, please, don’t worry about it!” I blurt out really quickly. “This was my fault too. I heard you speak, but I… I wasn’t really paying attention, because…” I blush a bit. “I was so focused…” I giggle nervously. “So please, you didn’t do anything wrong,” I say as reassuringly as I can manage.

“Really?” She sniffs.

“Really.” I smile at her, and start to giggle more at this ridiculous scene. “What a mess this is, hahaha.” I shake my head a little. “The two of us, as well.” She starts laughing along with me, which is perhaps even better to hear than her earlier moans. “We should probably clean up this mess a bit before we continue,” I say after I’ve calmed down a little.

“Continue?” she says a little confused.

“Well yeah. Did you think we were just going to get you off, and nothing else?” I ask incredulously, giving her a look. “Ah… but if you don’t want to keep going…” I suddenly change my tone, remembering I shouldn’t push.

“No, I mean, I… thought you wouldn’t want to… after this…” she says hesitantly. I notice she can’t really move without her cum running everywhere, and giggle a little again. There’s just something so silly about this.

“You just stay there, I’ll get us some paper towels. If you move, you’ll just make more mess,” I say, and she nods meekly at me. What a scene, haha.

I wash my hands,  and get the stuff out of my hair as best I can. Might as well take my knickers off too. I return with a roll of paper towels, and get Charlotte cleaned off.

“Thank you…” she says as she can finally sit up again. “I’m really so-” she starts, but I put a finger to her lips to shush her.

“I told you that you don’t have to be. And you can trust me on this,” I say and kiss her lovingly. Feeling her melt into the kiss makes it so much better. I reluctantly pull away again.

“Look,” I tell her. “It was a little strange, but also kinda fun. I feel like I need more practice, but you certainly appeared to be enjoying yourself anyway…” I grin at her, and boop her nose. It is nice to at least try to be the calm and dependable one for once. “Um… did you enjoy it?” I ask, letting my insecurity slip. She nods, and blushes so beautifully, then hugs me. I hear her sniff a little.

“Yes. Thank you,” she says again, and I hug her back.

“Thank you too,” I say, and I hold her for a minute before I feel the need to break the mood.

“Now… so… watching, and listening to you sort of… actually really turned me on, so… could you…” The words stumble out of me.

“Could I what?” she leans back and ask me. Damn, she’s collected herself enough to tease me. I recognise that look she’s giving me.

“You know…” I try to worm my way out of it.

“Know what?” she says. She isn’t going to let me get out of this.

“Charlotte, please…” I say, begging.

“Please what?” she says. Argh, she just loves making making me say embarrassing things.

“L… lick me…” I can tell she’s enjoying this way too much, but I’m going to beat her to the punch here. Before she asks another thing I keep going: “I want you to… lick my… m-my…” She tilts her head questioningly to the side. Curse you, Charlotte. “Lick my… pussy…” Why is it so embarrassing to say these things out loud? I’m an adult! “There! You happy?” She looks very happy.

“You could have been nice to me,” I complain. “Considering it’s our first time, and what I just did for you…” I can’t stop myself from pouting. “You knew damn well what I meant…”

“Did I?” she teases, then laughs when I shoot her a dirty look. “Okay, okay, I’m sorry. You were just so cute… but maybe you’re right that I should have been nicer.” I sigh dramatically.

“That’s what I get for cheering you up,” I say in an exasperated tone. “Maybe next time I won’t bother…” I say that, but I’m also really glad the mood has picked up. Us two joking and teasing like normal. She being much better at it than me. It gives me hope that this… sex… can also become normal for us.

“You can make it up to me,” I say, and plop down onto my back. While my body has calmed down some, I can still feel it tingle.

“Haha, fair enough,” she says in a delightful tone. I wonder if she’s feeling relief like I am. She leans down to kiss me passionately. She certainly knows how to take my breath away when she wants to.

I blush as she gets between my legs. Just something about seeing her down there is quite erotic. Did she feel the same when I was down there on her?

I’m fairly certain she has done this kind of stuff before, but it’ll be the first time I’ll feel her tongue on me. That thought alone is making me tingle even more.

“Let me know if I do anything wrong, or anything really right, okay?” she says, and I blink. Right, even if she’s done this before, she’s not done me before.

“Okay,” I reply, and try to calm down. But I can feel my anticipation rising as she slides down. Soon enough I can feel her breath down there, and I let out a whimper.

I watch her intently as she reaches out to touch me, and I’m not able to suppress a gasp when she finally does. It really feels very different when it’s someone else touching you. Geez, does she have to look so pleased about it? I’ll be blushing for days…

She spreads me open, and I can already feel shivers running through me as she leans in. Maybe I should have quickly washed down there too while I was up, it has to be kinda gro- Tongue! Her tongue is on me! It’s moving! I moan loudly and squirm about. It’s been a while, but I didn’t expect it to feel so intense. I feel it shoot through my every nerve. Ah, not my-

“Eeeeeeeeeeee,” I squeal as her tongue moves onto my clit, and I think my whole body tenses up. “C-Charlotte, t-too much,” I hiss, and she stops. I sigh, slightly relieved, and slightly disappointed. My body is able to relax again.

“Sorry,” she says, giving me a concerned look.

“It’s… it’s okay,” I say while trying to catch my breath. “I just… can’t handle you… on my… c-clit… right now…” I try to smile. “The rest was good… so please…” She gets what I mean, and starts probing me again with her tongue. Oh damn… it really has been too long.

I lean back, and give in to the sensations. I guide her a little bit, but she seems to be doing quite fine on her own. She’s probably watching my reactions like I was watching hers. I’m feeling dizzy and warm. Her tongue is also very warm. And moving all over.

She’s holding me gently now, around my thighs. Am I squirming too much? I’m not able to stop.

Ah! It slipped in. She’s licking at my insides. Ah damn. I won’t be able to last much longer like this. Her being down there, eating me out. Does she like how I taste? I can’t look.

“I… I’m not gonna… last…” I say, gripping the sheets tightly. “Please… ah… a little… faster…” She obliges right away, and I let out a satisfied hiss. It feels so good. Fuck, here it comes. So close now. Just… a little… more…

“AAaaaaahhhhhhhhh!” I cry out as the dam bursts, and release washes through me. I don’t know how long it lasts, but it feels like forever, yet also like it’s over too soon. It’s so different when someone else does it. It’s been too long.

I shudder pleasantly, and look down at her to see she’s smiling up at me. Even with her chin covered in my spunk she’s beautiful. My heart pounds a little extra as she licks her lips.

“How was it?” she asks playfully, causing me to blush even more.

“Um… very good,” I reply. The way she grins happily at me makes me have to look away. “I w-would have thought that much was obvious…” I say, feeling quite embarrassed.

“Yeah, but…” she crawls up to me and kisses my cheek. She smells of me. “I want to make sure.” I turn my head to meet her lips. She tastes of me too. I wrap my arms around her and pull her down on top of me. Tasting myself on her tongue feels really erotic. I wonder if she would feel the same if our positions were reversed?

Wait, what’s… oh. She’s hard again. I can feel it press against me, so hot I worry it may burn my skin. Should I give that part of myself to her today as well? The possibility had been part of our talk beforehand. And I had planned to do so eventually. I just hadn’t been sure whether today would be the day. Will it really fit in me? The thought is making me feel all tingly again. I love her, and I… want to know.

“Charlotte?”

“Hm?”

“Do you want to… um…” How do I even phrase this? How do I ask someone to put their cock in me without dying of embarrassment? “Take it to the next step?” I try, hoping she’ll take the hint.

“Huh?” she says, and gives me a confused look. I’m worried I’ll have to explain further, but I can tell when realisation dawns on her. “Oh, you mean actually…” she says, and I nod shyly. Please don’t tease me, please don’t tease me, please don’t tease me. “… putting my cock in you?” How can she say that so shamelessly? I nod again, and I’m sure I’m blushing furiously.

“Are you sure?” she asks, and smiles kindly at me.

“Y-yes…” I reply, forcing myself to not look away. “We’ve gotten this far, so we might as well get it ov- ah no! T-th-that’s not what I mean, I meant-!” I cover my face with my hands and groan. Kill me now. I hear her chuckle, and she gently pulls my hands down so she can kiss me. Her warmth is comforting.

“You don’t have to force yourself,” she assures me, and I feel so hopeless.

“I’m not,” I whine. Gods, I must sound so pathetic. “I just meant… I feel like I’m in a good place right now. It feels like a good time t-to try it.” I hope I sound sincere. She looks at me for a moment, probably thinking it over.

“Okay,” she says, and starts to move down. “But you have to tell me right away if you change your mind. I don’t want to… hurt you…” I can hear a slight tremor in her voice.

“I will,” I promise her. The tingling won’t stop as I see her go down on me again. She wants to make sure I’m still wet enough. Spreading me open again, she slides a finger into me. I flinch as it goes in, and she stops moving immediately.

“Keep going,” I say. “It just… took me by surprise a little…” Even though I was fully expecting it. She starts moving again, and it feels pretty good.

“I’m going to insert one more, okay?” she says, and I nod at her.

“I’m ready,” I say, taking a breath. She pushes two fingers together before sliding them into me. I moan lightly. “Feels good…” I tell her, and she seems relieved.

“Well, you’re certainly quite wet,” she says, and licks her fingers. Causing me to blush again.

“Don’t tease me,” I say, and she laughs. She sits up and starts getting into position. It looks bigger when I see it up against me like that. She’s guiding it towards me, and I can feel panic rising.

“W-wait!” I say quickly, and she stops. It’s so close to touching me.

“Changed your mind?” she asks, sounding concerned.

“N… not exactly…” I say, and sit up. “But I think I have to be in control for this… so could you lay down?” I shimmy to the side to give her room, and she gives me a quick kiss before laying down. I’m less sure I’m ready for this now, but I’m still feeling very tingly. I straddle her. The way she’s looking up at me just makes my heart race even louder. Damn it, I don’t really have enough height.

“Ho-hold my hand?” I ask her, and she thankfully does so. I’m going to need some support for this. I get up into a low crouch. Ideally I’d like to be able to get right on top of it so I can just sit down. I squeeze her hand and use it for balance, and I feel her cock twitch as I take it in my other hand.

This is going to be in me soon, I think to myself as I lift it up. I probably shouldn’t think too hard about it. Heh, hard. It doesn’t take too much effort to lower myself so it’s positioned against my pussy. Now how do I…

I understand enough to realise I need to get it lined up against my opening. Moving it back and forth feels really weird, as if my groin is on fire. The way it’s touching me doesn’t feel like fingers or a tongue. I hear her moan softly as I fumble about. Don’t know how that would feel good, but cocks are weird.

Ah! It sort of pops into place suddenly, and I can feel the tip pressing against me. It twitches, and I almost raise myself up. She’s watching me very intently now, which is definitely making me feel self-conscious. Still, so far, so good. Is it really going to fit in me?

“Okay, here goes…” I say, as much to myself as to her. I grind against it a bit to make sure it’s actually properly in position, and she moans louder. It seems to be. Now I just need to lower myself down, right? I squeeze her hand, and she squeezes back. Okay. Taking a deep breath, I start to push down. There’s a little resistance at first, but then…

It’s spreading me open. It’s going in. Ah. Ah! The head is in! Oh damn… this feels strange. I stop to catch my breath. It’s in. A little bit, at least. I think that was the thickest part of it, so the rest should be fine. Maybe.

Ah! I feel her starting to push her hips up. “C-Charlotte, stop,” I say, and she does.

“Sorry,” she says, and slides back down. The head pops back out, so I guess I raised myself up a little automatically.

“Sorry I’m so slow…” I tell her, but she shakes her head.

“It’s okay, take your time. I’ll control myself,” she promises. Lining her cock up again, I take a couple of quick breaths before I lower myself further. The head slides in once more. It doesn’t hurt like I’ve heard people say it does. The way it’s spreading me open and filling me up is a really strange sensation, and it’s making it a little hard to breathe. There’s the feeling of being strained and stretched, but I wouldn’t call it pain.

“Are you okay?” Charlotte asks when I pause again. I think it’s about halfway in now, and I’m probably squeezing her hand really hard. Is she breathing as heavily as I am? Her cock feels so warm against my insides.

“Yeah, it just…” I take in another gulp of air. “I think it’s going to take… some getting used to, ehehe…” I blush and smile nervously at her.

“Well, I think you’re doing great,” she says, and moans again. “Ah-also you’re squeezing…” It takes me a moment to realise she isn’t talking about the hand.

“How about you?” I ask. “Are you okay? Am I doing anything wrong?” She smiles warmly at me.

“I’m fine,” she replies. “It’s… it’s really hot and soft inside you,” she says, and I nearly lose my balance.

“I don’t understand how you’re able to just say things like that.” Even if she’s not embarrassed, I feel embarrassed on her behalf. She just giggles at me.

I keep going. Being filled up is starting to go from being strange, to strangely satisfying. She is in me. Charlotte is inside me. Just the thought alone is a turn-on. The feeling… is still going to take some getting used to, but I think that shouldn’t be too hard. … heh, hard. … I’m not much of an adult.

Ah! Our hips touch. It’s all in me now. The whole thing. It managed to fit. I guess my vagina is just that amazing. Okay, that was a really corny thought, I’m glad I didn’t say it out loud.

“It’s in,” I say instead, and slide down on my knees again. Crouching like that was really starting to feel uncomfortable.

“It’s in,” she confirms, letting out a deep breath. Was she holding that in?

“Now… um… n-now what?” I ask, feeling a bit of deja vu. You’re supposed to move, right? Damn, I’m so full. She chuckles softly.

“Well, you could just keep sitting like that,” she suggests jokingly. “Or… we could say that’s enough and stop there?” she asks, and it doesn’t sound like she’s joking about that. I can feel her throbbing inside me.

“No…” I say, shaking my head lightly. “I want to… feel more of this…” I’m still holding onto her hand. “But I really don’t know how to… could… can you… show me? O-or can you do it?” This is awkward to ask, but I’d rather she take control back now.

“Okay,” she says, and reaches out to stroke my other arm. “If you get off of me, we can switch places.” I don’t move. The idea of pulling all the way out, and then pushing back in from the start…

“Can we do that without pulling out?” I ask. Maybe that’s a stupid question. She lets go of my hand, and pushes herself up a bit. The way she shifts inside me feels weird and electric.

“It’s going to be easier putting it back in again now that we’ve done it once,” she says when she’s fully sat up. Now it’s like I’m in her lap, just with her cock still buried deep within me.

“Yeah, but…” I put my arms around her and cling on. “I’d rather not.” She starts stroking my hair in the way she knows calms me down.

“Are you really sure you want to do this?” she asks, and I squeeze her tighter. The truth is I’m not really sure. But now that we’ve gotten this far, I think it would be better to keep going than start all over next time. Or worst case: maybe I never work up the nerve to do this again, if we don’t… don’t finish this time. I squeeze around her cock too, and her reaction is somehow comforting.

“Yes,” I finally say, determined. She kisses me on the cheek. I’ve noticed she likes doing that.

“Alright. But if you really don’t want to pull out, then we’re going to have to be careful,” she says. We start slowly turning around, and I unintentionally move up and down in her lap a little. I bury my face in her shoulder to stifle my moans. It’s definitely weird to feel it move, but it’s also touching so many spots inside me at once.

“Sorry…” I say in a low voice once we’re fully turned around. “I know I’m being weird, and making things difficult… I’ll do better next time…” She smiles at me, and starts easing me down onto my back.

“Hey, don’t be sorry,” she tells me. “I already told you: Don’t worry about it.” She slides out a bit, then back in as I’m lowered down. Which is a bit scary, but it feels good too. “Also, next time?” she asks teasingly. “I’ve not scared you away from cocks, then?” I blush, and shake my head.

“N-not when it’s with you,” I say. “I… I love you Charlotte, and I want… all of you.” For once she seems lost for words, and I giggle a little at her expression. Such a beautiful blush. She bends over to kiss me, and I eagerly let her tongue in. Now she’s inside me in two different places at once, which feels a lot more erotic than it maybe should.

“You are so cute,” she tells me in her most seductive voice. It makes me want to let her do anything she wants to me. “I love you too, Jenny,” she says and gets into position. I’ll be able to see her every movement like this.

“Go easy on me…” I say with a hint of pleading, and she smiles at me.

“Of course,” she says, and slowly starts to move. Pulling out a little. Oh damn… Then pushing back in. Oh damn… She’s inside me. She is moving inside me. I can feel every part. It’s so much. I moan, and groan. Her movements gradually get longer, but she makes sure not to pull out completely. I want to bury my face in something. It’s like she’s moulding my insides in her shape. Making me hers.

“You doing okay?” she asks me, panting lightly.

“Mhm,” is all I answer.

“Does it feel good?”

“Mhm!” It really doesn’t feel so weird any longer, it just… there’s so much of her inside me… touching so much of me. “How about you? Are you… feeling… good?” It’s hard to speak, but I want to know. I don’t feel like I’m contributing much here by just writhing around.

“Mhm,” she replies, and it turns into a moan. “It’s real… really warm inside you, and… you keep squeezing…” Do I? I’m not even aware. This feels like it’s melting my brain.

“Can you go… faster?” I ask, and she takes a moment to reply.

“You… sure? I might cum… pretty soon… if I do…” she says, and the idea rolls across my mind. Is she going to cum inside me? Do I want her to? The thought is really making me tingle all over, and we discussed it. We just didn’t reach a decision. Gah, it’s so hard to think. Damn… yeah, I want her to make a mess of my insides. I want to feel it.

“Yeah… please… and- oooohhhhhh,” I moan as she hits deep inside me. I don’t know what she hit, but I certainly felt it. What was I… oh, right. “And you can… c-cum inside me…” I say.

“Huh? Are you-”

“Yeah, I’m sure,” I say before she finishes asking. “Just do it.”

“B-b-but…” she says, but I can feel how she’s throbbing and pulsing.

“Please,” I beg her, and she finally seems convinced. She changes her position a bit, and starts moving faster. Oh damn oh damn. A lot faster. Oh fuck. I’m losing my mind.

She comes all the way down to kiss me passionately, yet still she’s able to keep slamming into me. Ah, I can feel her swelling, just like before. She’s close. The anticipation is making all of me tingle as if electrified.

“I… I’m about to…” she says, short of breath. I kiss her hungrily, and wait for it to happen.

She moans really loudly into my mouth as she cums, and breaks free of the kiss, gasping for air. Hot. It’s so hot. I feel it shooting into me, and it’s so damn hot. I think it’s burning me.

The whole sensation of it pushes me over the edge, and I start clamping down on her hard. I want to squeeze every little drop into me.

She stops shuddering after… some amount of time, I don’t know. I don’t go on for much longer myself. I hug her tightly against me and kiss her again. She seems a little more tired than I feel. Well, she did do most of the work at the end there.

Feeling her go soft inside me and slide out is also a strange sensation. This was all… certainly not what I’m used to. I definitely didn’t hate it, though. It felt good, and I certainly got really into it, but I think that’s also because it was with her.

I keep hugging her against me, and let her rest. I need to catch my breath too. Letting her cum inside me… that was me getting swept up in things. I’m on birth control for other reasons though, so I’m not worried about that. I just wonder if it’s going to be hard to… get it all out again? Nah, it’ll probably just glide out on its own soon enough… maybe I should grab some paper towels right away.

I get the pillow placed under her head, then sit up and grab the roll of paper towels. Damn it, yeah, some of it’s already dribbled onto the sheets, but I can catch the rest, at least. I didn’t really notice earlier, but it has a very distinctive smell.

Turning around, I watch her resting for a bit. Has she fallen asleep? I reach out and caress her face. She nuzzles against my hand like usual.

“Hey, you doing okay?” I ask. She slowly rolls onto her back, and looks at me.

“Yeah… you?” she asks, and I giggle at the state of her.

“Yeah…” I reply with a smile. “You know, if I’m perfectly honest… that was a really strange experience. And thrilling. And a bit scary.” I see a flash of worry on her face. “Ah, don’t get me wrong! I didn’t hate it, hopefully I managed to demonstrate that. Ehehe…” I laugh sheepishly. “It felt really good, it was just… very different. I… ahm… think I learned a lot.” I plop down next to her, and she rolls back onto her side to look at me.

“What I’m trying to say is… I liked it, but it’s going to take some getting used to,” I say, and stroke her hair gently. “And since it’s with you, I want to get used to it.” She blushes lightly, and smiles at me. So beautiful. “Sorry I’m so bad with words, I’m not sure my brain is working right yet, haha.”

“Pfffft. Is that my fault?” she teases.

“Yeah, everything’s your fault,” I say, and kiss her softly. “But… um… I hope you liked it too… I mean! I know you came, of course! But I kinda feel like I was a lot of trouble to deal with…”

“Ahaha, don’t worry about it. Really, don’t,” she says, and scoots a little closer. Touching her nose to mine. “It was a bit awkward maybe, but aren’t first times supposed to be? I really appreciate your patience…”

“I feel like I should be the one to say that,” I tell her. “I didn’t know anything, yet you taught me, and let me take my time to figure things out…” I lean my forehead against hers.

“Hey, I’ll say in all honesty that I’m relieved you wanted to even… learn in the first place,” she admits. “I was a little… no, I was very worried I’d scare you away.” I put my arm around her and pull her as close as I can.

“I’m not going to let you go that easily,” I say, and giggle. I still don’t think I deserve her, but so long as she wants me… “I really love you, you know.”

“Yeah,” she says. “I love you too.”

We end up falling asleep there for a while.

~Wulf

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Posted on May 23, 2017, in Fiction, Storytime and tagged , , , , , , , , . Bookmark the permalink. 1 Comment.

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