Cherry

My girlfriend wants to try anal, and we're...

"Almost there...?" She's biting her lip, squinting, concentrating. Jenny is surprisingly cute like this, we haven't pushed too many boundaries before so this is a new look for her.

Plus the angle isn't bad... Head down, ass up, her arms crossed under her cheek and her ankles crossed between my legs. That beautiful body arched against me, grinding herself sensuously onto my cock. Her hair spills across her shoulders, echoing the flex of her, dark gold on soft skin.

I can feel her slowly relaxing. Her pussy feels incredible but this is a different sensation. The hottest part is still her reaction though, I can feel the tension easing from her body; both around my cock and the muscles of her back under my slowly massaging fingertips.

This is pretty intimate to start with, but I thought I'd talk about what inspired me to write this. Some writers fall in love with the moon and write sonnets, but I found inspiration in the cute little noises Jenny makes with my achingly hard cock... nearly inside her tight, pink, virgin asshole.

Such cute noises. Like she doesn't quite know she's making them; little sighs when it starts to feel good, little gasps when she got brave enough to push further back against me, little whimpers when it hurts just a bit.

I could come right here right now, with maybe a little eye contact and the right combination of horny noises. I'm so hard I could probably keep fucking her even then, just ease my throbbing dick deeper into her arse with the hot natural lubricant aiding me.

And hold myself there until my eyesight came back, and the clashing neural cymbals faded to a pleasant static-y ache. Until she's relaxed and happy and horny, and she gives me that look that says 'fuck me hard, big guy'.

...

I let my gaze drag softly over her back from where our flesh meets, along her spine until I catch her sly blue eye as she half turns to look.

"How are you doing, Gorgeous?" I'm being supportive as hell right now. We've really been connecting the last few weeks and I think trying this might be the reward.

If we can do it, that is. So far we're about... halfway, and Jenny is doing some good for my ego by writhing and moaning like she's being ravished by a 'roided-up Gorgon right now, but I don't think the eager pulsing of my cock inside her is helping.

"You're really big..." Jenny confirms for me.

"You always know just what to say to me..." I hiss with laughter, but the movement is uncomfortable for Jenny and I withdraw just a little, give her some breathing room.

"Relatively big then..." Jenny doesn't speak in complete sentences when she's being fucked in the ass; we're learning a lot about each other today.

"You want to go back to the toy for a bit?" I ask, and keep any disappointment from my voice. It takes as long as it takes, and Jenny is worth the wa..

"No..." She purrs at the same time she starts grinding back down onto my cock. The friction is delicious for me, but I think a little more lube would make things easier.

"Fuck..." I suppose I act out my verbs when I'm horny, or narrate what I'm doing, it depends how fatalistic you are. "Jenny..." I growl and fall to rest with my weight on my knuckles, my hands either side of hers.

"I love you." She says to me, relaxing a little just to emphasise the point I think.

"I love you." I say, tensing up a little. Christ, this is intense. This is like a whole other virginity she'd been holding out all this time, and I'm the lucky bastard that gets to pop her cherry.

I realise this would be a weird time to propose, and that I'm going to have to make up a story about where I was when I decided Jenny was the one for me, if only so we have something we can tell people in polite company.

Then I realise I'd need a ring too. Tradition really cramps my spontaneity sometimes.

Jenny pushes further than before, she feels my thighs meeting hers and tenses up.

"Easy..." I grunt at the sensation of being enveloped by her, but as wonderful as it feels for me, I have to consider this is Jenny's first time.

"Oww..." She whimpers softly, trying not to tense up more from the sting. I pull back again slowly.

"Here, lie back down for a bit." I say. "Is it bad?"

"I've had bigger pains in the ass than this." Jenny is also cute when she's doing deadpan understatements. We share a comradely chuckle.

I slowly ease my still-throbbing cock out of her. Jenny winces as I pop out of her and lays gently back down on the bed.

She's rushing it a little, thinking she can just push back against me and relax after, not before. That kind of wild fuck seems a little advanced for a first try.

My kisses leave little smudges of moisture on her skin, glinting in the light as I nuzzle between her thighs to give her slick, hot, aching pussy some attention.

She's wet, swollen, sticky. Like if we'd been out all day and I'd been teasing her with kisses and touches until she was almost humping my leg, and she couldn't do anything about it until we got back to the car...

Good times. I often find myself remembering things like that while I'm kissing my lover's clit for her.

"Mmm..." Jenny has a low, expressive sort of moan at times like this. Even though she's a little sore she's still as horny as I am. No-one said anything about giving up.

Jenny spreads out her arms and focuses on the coolness of the bed beneath her. When my lips softly tug at her clit she draws up one leg a little, giving me better access.

"You're obsessed with my pussy..." She teases me in a lazy, distracted voice. I reply with a loud sucking noise as I slurp on her clit, making her shiver and then giggle.

To be fair, I'm obsessed with her ass too, and her tits. Jenny has a broad appeal, and not just because of her slim, lithe body. Once I caught myself watching her sleep in my arms just because she was beautiful, just to listen to her breathing. I never realised I was sentimental before that.

I was about to get lost in a happy little reverie while I sucked her clit, but Jenny helpfully wiggles her ass under my palms holding her open to me. I sometimes think we would have tried this months ago if I didn't keep getting one taste of her then forgetting everything else.

This wasn't quite what she was prompting me to do, but I let out a low growl of pleasure as I keep licking and kissing slowly upward from her pussy to her ass.

"Babe... God..." She giggles in between the words, surprised at my boldness. I've never kissed her there before, she's always been too shy to let me before.

But she's letting me now, and the moan that interrupts her giggling is feedback enough for me to continue. She tastes of the lube we've been liberally applying, cherry flavoured on my whim. Cherry lube for popping her cherry with, from me that passes for wit.

"Fuck..." Jenny's voice is brazenly loud for a second and then she shuts herself up, blushing from head to toe as she clamps a hand naughtily over her lips.

I had my mouth full, so I just growled agreement from between the gorgeous curves of her backside and gently slide my warm tongue inside her.

"Oh my god..." Jenny is really outdoing herself with the commentary today. It's about half the reason I've been rock solid for the last hour or so, and just like Jenny I'm starting to get a little ache of frustration deep inside.

Jenny writhes subtly in the bed, this new sensation is probably where we should have started. But build-up is important, she would've been too shy to let me without a lot of foreplay, cuddling and a drastic temporary lowering of inhibitions.

She feels almost as tight to my tongue, but as I reach under my mouth to rub her clit with the pad of my thumb she relaxes her ass.

"Mmm." I mumble, not stopping now we're making progress.

"Like..." Jenny trails off. "Like that?" I can see the rosy pink blush wash over her skin, at least the limited but erotic sliver of her ass and back that I can see from here.

"Mhmm..." I mumble again, with feeling. Jenny seems to have gotten the hang of relaxing now, letting me give her long licks as well as gently fucking her with my tongue.

Jenny tenses up, her feet had been making lazy circles in the air but now her legs straighten out and clamp tight around me.

"Ooh..." Jenny is lying with her head on her folded arms, her eyes shut as she focuses on the feeling.

For a second I wondered if Jenny came before I expected, it was a close run thing and even she wasn't sure at first. She clamps her thighs hard on either side of my neck, trying to wring the last delicious sensation from her nerves.

I try to press my tongue as deep into her as I can. I've always had something of an oral fixation when it comes to women, though I'd argue in Jenny's case it's because of the way she reacts.

"Fuck me..." Jenny says in a whimper. I smile and keep up my teasing licks, chuckling softly.

"No, really." Jenny says in a more urgent tone. "I'm ready. Fuck me..." She moans again as I circle her ass with the tip of my tongue, dipping in to tease her again.

I'm pretty hungry for it too by this point, I scoop my arm under her hips and lift her up to her knees. She's looking right at me, the view along her curving back as I trickle lube onto her, then myself, then spread it around.

"Mmm..." She purrs for me as I press the head of my cock into her again. Easier this time, Jenny has drawn a hand up between her legs to rub herself at the same time.

"Perfect..." I was going to say something else but I just trail off into a happy little groan at the hot slick feeling of her.

I watch her eyes as we get back to about where we were before, she bites her lip and watches me back.

I push further, slowly but firmly, and Jenny leans back into me just a little as we meet in the middle. After a few weeks talking about it and a few playful attempts with fingers and toys, we're there.

"Oh..." Jenny makes such a soft, intimate little noise. It wasn't noisy before but it felt like the whole house went silent. I'm reminded of other intimate moments with her, it felt like that the first time we kissed too.

I wait a moment, watch her face as I run soothing palms over her back. Her eyes are closed now, but she gives me a slow nod, sighing against the pillows.

I pull mostly out and slowly push back, eliciting another low groan from both of us. It would be stupid to play favourites with Jenny's body, but this is different. This kind of intimacy is new to both of us, it adds a nervous energy to every sensation. It's not just sex when you're exploring like this.

I repeat the slow fuck, and get the same slow flex from Jenny as she shifts on the bed and lines me up just right.

It's been about a minute since I teased her, I notice.

"Having fun, Gorgeous?" Her eyes flutter open and she blushes a deep crimson, biting her lip again. I love when she does that.

I emphasise the question with a slow, deep fuck, an easy rhythm I could keep up all day.

"Mmm..." Jenny turns her head to rest on the other side, avoiding my steady gaze but still pushing back against my cock.

"That's a 'yes'." I lean down and support my weight on one hand, holding myself deep inside her as we adjust position. Now Jenny's beautifully curved back is pressed to my chest, my arms slipping under her hips to bring her as tight against me as I can.

"Fuck..." I whisper in her ear, kiss her cheek as she chuckles. I can only act all cool and aloof for a little bit, then I remember that Jenny is naked and we're fucking. No matter how many times we do, that thought never gets old.

I glide my hands up her body and take hold of her breasts as I thrust deep into her ass, both of us lost in the feeling of it all for a while. That slow fuck was like a dance, neither of us feeling any urgency to do anything but enjoy each other.

"I love you." I kiss her earlobe after I say it, let out a long contented groan as she takes me easily now.

"I love you too." She giggles, I feel the vibration of it inside her.

"What's funny?" I croon in her ear, unable to pay too much attention to anything other than holding her and making love to her.

"You go all warm and fuzzy as soon as you're in me." Jenny giggles again, then moans as I flex my cock inside her.

"Warm and fuzzy?" I try to convey what I think of this in the more confident thrust, the playful squeeze of her nipples between my fingers and thumbs.

Jenny doesn't answer for a few moments, I remind myself this is a first for her and slow down again. Jenny lazily lifts her head and turns the other way to face me.

"Mmm..." Jenny luxuriates under me. "You're so serious until you're fucking me, then you..." She trails off as sensations ripple through her.

"Then I what?" I prompt, teasing her again.

"Ahh..." Jenny reaches behind her to grip the back of my neck by the hair, squeezing me tight. I smooch along the nape of her neck and knead her breasts in my hands, waiting for her answer.

She's flushed and distracted, her full lips hang slightly parted as she breathes deep and fast, struggling to balance until I put a supportive arm around her.

What the hell, we can talk later.

I kiss between her shoulder-blades, making her shiver, then I put one hand there to keep her head down as I start fucking her harder and faster.

I think Jenny might just be a natural. This new sensation makes her squirm and writhe like she does when I'm rolling her clit between my lips.

The great thing about her is that she's full of surprises. I didn't know she could draw until we'd been dating for four months, now I have one of her designs tattooed on my arm. This time she surprises me by getting so into it she got almost... competitive.

Jenny gradually lifts up onto her elbows and I lift up to give her room, one arm supporting us and one still wrapped affectionately around her chest.

She lifts up more and we both wobble in balance for a second as we transition from prone to some variation on doggy, and now into a sensually slow sort of grind in my lap as I kneel and she arches her back.

I want to say something. But I was too smart to interrupt this wanton mood she's in, things get really good when Jenny is feeling brave and explorative.

"You fucker..." She accuses me sweetly, as if this wasn't a joint effort, as if it wasn't her grinding down onto my cock that was making her feel that way.

I keep quiet, accepting the credit along with the blame, bite her earlobe in that friendly 'you're mine' sort of way.

Usually that makes her giggle, sometimes it makes her so ticklish she fights me off. Today she sighs low and loud, like she was waiting for me to do that. I feel the vibration of it in her chest, and then she lifts her hands off the bed and wraps them around my shoulders from in front.

Riding in my lap, arching her back, sticking her chest out as I go back to holding her breasts in each hand, pulling her down onto me a little harder as Jenny really starts getting into her rhythm.

"... fuckin' love you..." I say between groans as I hug her tighter to my chest.

"... love you..." Jenny never fails to respond to those three little words. It's becoming a bit of a game for me to say it when she's losing herself in the moment.

She's gasping now, panting and gripping my neck and shoulders hard. I tweak her nipples just to make her moan and then wrap my arms around her hips so I can fuck her harder.

"... fucker..." She's still calling me names, and I feel like evening the score.

"... you're the..." I try, but Jenny had started experimenting with squeezing me as she rides me, and it took a minute for me to focus on anything else.

"You were... saying?" She laughs, grinding down deeper into my lap. I become aware that she's taken over somewhere in the last few minutes. The woman is insidious, I love that.

I groan and give up on dialogue for a bit. We can think later.

She feels perfect, smooth and lithe, misted with passionate sweat, blooming with heat. Never ever wanted to let her go.

So I held on, and grit my teeth, and kissed the back of her neck, and growled the way that makes her shiver.

And came, in an energetic, bounding series of seconds as Jenny gets there right with me. Hard to tell who set who off, but I'm blaming her cute moans and the sly look in her eyes.

Heat creeping under my skin, the coolness of her shoulder against my cheek as I hug her, slowing down but not stopping.

Jenny felt it as a wild frozen second, a novel blend of min/maxed sensations that made the build-up seem tame. She tenses hard around me, holds herself down deep in my lap and lets out a low hard groan, then suddenly remembers to breathe in.

"Fucking..." Jenny also acts out her verbs on occasion, but this time she only manages one before letting out a shivery kind of unintentional groan that teases the last clench of orgasm from my body.

But Jenny, being a show-off at heart, manages to keep going for... I don't know. I want to say at least a minute, but it was probably half that. I was too distracted by Jenny's intensity.

"Mmm..." A cute little whimper halfway through as she manages to catch one deep breath. She's shaking in my lap, unsteady as her hands move down to grip my thighs under her for support.

I chuckle, rub my cheek against hers and hug her tight as she relaxes in stages back into my arms.

We wobble as she forgets to balance, but I was ready for it, keep her steady, listen to her happy chuckling noises as she remembers what we just did.

"Mhmm..." She agrees with something one of us said earlier, making me laugh.

My laugh makes my cock throb inside her and she moans, flexing her back against my chest.

"That was..." I couldn't think of more words.

"Yeah..." She agrees with me.

With a pair of lustful groans, we part, and she turns over in the bed.

I watch her eyes, considering that we only had one first time together like that, and that it went so well there might be a second time.

"You're the best, Babe." I tell her, I've told her before but she looks like she believes me this time. It would've been worth the wait just for that.

"Well then you're the second best." She tells me.

We kiss.