Rapunzel in New York – A Sexy Fairy-Tale. Category: Long and Satisfying
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Welcome to my first new piece in what I’m calling ‘phase 2’ of the blog. For an explanation, see this post.
So, I thought I’d challenge myself on several fronts. Firstly, you’ll notice that I’ve got an illustration rather than a picture of my arse at the top. I’ll still be taking photos, but I wanted to mix things up by occasionally doing an illustration. Yes, it’s all my own work – no fucking AI involvement (it would probably be better if I got AI to do it, to be fair).
Secondly, I wanted to challenge myself with the story. I’ve always written in the first person as myself. It’s the easiest way of doing it. So I thought I would try and imagine myself as a man. Never having had a cock myself (except a strap-on one), I’ve done the best I can to imagine what it might be like to be the fuckor rather than the fuckee. I’ve also set this tale in New York with an American protagonist, so I’ve tried to make the language fit with that. Hey, all of this is a work in progress, and you don’t grow if you don’t push yourself, do you?
My initial idea was that Rapunzel would be a flautist, which is how I originally wrote this, then I watched the BBC Last Night of the Proms a few days ago, and was reminded of the insatiable horn (see what I did there) that I’ve got for the exquisite trumpet virtuoso, Alison Balsom, who also just happens to have long blonde hair. I’m sure she wouldn’t thank me for it, but I dedicate this to her. #sohot #trumpetrocks
I hope you like it.
Approximately a 15-minute read.
***
I hadn’t been in Manhattan long – only about three weeks – when I first saw her. I’d moved into a little apartment on West 20th Street, overlooking the Highline. My place is on the second-from-top floor and looks out towards the Hudson, or at least it would if it weren’t for the fancy apartment block facing mine on the other side of the Highline. Man, those places are swanky – all the apartments have floor-to-ceiling panoramic windows looking eastwards and blocking most of my view of the river. Still, I had the telescope which my parents had gifted me when I moved, and I was still able to see through the gaps to watch the river traffic and comings and goings in the neighbourhood.
I’m gonna confess right away. I did – do – sometimes sweep my telescope, set up on its tall tripod, across the apartment blocks surrounding me, just in case, you know? Hey, I’m a normal, single guy. Don’t tell me you wouldn’t do the same.
On that one evening, I’d been drinking a couple of cans and watching the river when a movement from the block opposite caught my eye. I swept the telescope to where I figured it was and jumped out of my skin when I saw someone else in that block looking back at me through their own telescope – a beautiful brass one on a dark wood tripod. The person looking through it was beautiful as well. She was wearing an ivory-white silk robe, and her long blonde hair was pinned up; a few stray locks tumbling messily down the sides of her delicately featured face.
***
When she saw that I’d seen her, she took her eye away from the telescope and gave me a wave. I was embarrassed as hell, but I gave her a wave back. She walked to the side of her window, and shutters began to move across. She waved again just before she disappeared.
It took me a while to fall asleep that night.
Early next morning, a Saturday, I went out to get a Starbucks. I froze as I saw the blonde girl standing a couple of places back in the line. She spotted me and gave a little knowing smile. A few minutes later, as we waited for our orders, she came and stood right next to me.
‘Well, well, if it isn’t my peeping Tom!’
I gave a nervous laugh. ‘I’m Billy, actually.’
‘I like ‘Tom’ better,’ she said. She was about twenty, English, well spoken, and told me that she was a trumpet performance major at the Manhattan School of Music.
‘I expect you’re wondering how a student can afford to live where I do?’ I told her it was none of my business, but she clearly wanted to share.
‘I’ve got a sugar-mommy.’ She paused to study my face, looking for some hoped-for reaction. I tried hard to remain inscrutable.
‘She’s a financier,’ she went on, ‘lives in Dallas with her doting husband and two perfect children, goes to a big old Texan Church every Sunday, raises her hands and renounces the sins of the flesh, then flies here a couple of times a month for meetings, stays with me in the apartment she pays for and licks me until I come all over her face. She gives great head, so it really is a win-win.’
I was stunned and had no ready response.
***
An order was called out: ‘Rapunzel.’
‘Oh, that’s me!’ she said and went to grab her drink. ‘Well,’ she said, ‘nice to meet you, Tom.’
‘Wait – is Rapunzel your real name?’
‘Oh yes. My parents have a lot to apologise for – my sister’s called Cinderella.’ She laughed at my bemusement. ‘Just kidding. She’s called Saskia. Rapunzel is my name, though.’
‘It’s, uh, very pretty.’
‘No, it isn’t, and you’re just being nice because you’d like to get into my panties.’ I still had nothing to offer in response. ‘Well, I really do have to go, but my benefactor flies in on Monday. If you happened to be looking out on Monday evening, I’d try to give you something worth watching.’ And, just like that, she was gone.
I had nothing much to occupy me that weekend, which was a drawback as I struggled to think of anything but my encounter with my gorgeous neighbour. I’ve never looked forward to Monday as much.
I rushed home after work on Monday, picking up tandoori to go on the way and settled myself, like an ornithologist, on my couch, lights out – one eye on the TV, one on the window across the way. Waiting for a sign of movement to trigger my leap to the telescope.
I waited and waited and waited again.
***
I think I was beginning to nod off when my peripheral vision caught a movement. I was instantly awake and leapt to the telescope, fastening my eye to the eyepiece as quickly as I could.
The blinds at Rapunzel’s apartment were half-opened. There she was! She was wearing the white silk robe again, and she stood, with her hands resting on her hips in a 50s pin-up style pose. As soon as she saw me leap into action, she gave that little wave again, then reached to the back of her head. A couple of flicks and her hair was released. She ran her fingers through it, shaking it out and tossed it so it fell over her left shoulder and down. Man, I don’t think I’ve seen hair longer; it fell below her waist, down even to the tops of her thighs, silken and glossy. She untied the robe and shrugged it off her shoulders, letting it fall to the floor. Underneath, she was completely naked. I can tell you, I nearly had heart failure. She stood for a few moments, letting me get my fill of the view and then pointed downwards to the bottom of her window. I dropped the telescope a smidge and saw three pieces of legal-size paper stuck to the glass, each with a digit on it. In a few moments, and with a shock, I realised she was telling me her apartment number.
I have never moved so quickly. I was out of my building and across into the foyer of hers in no time.
***
She opened her door to me in the same state of undress that had provoked my frenzied sprint across from my block.
‘Gosh,’ she said, ‘that was quick. Nothing much on TV then? If I knew before that just letting my hair down would get you charging up here to save me… weapon in hand – well.’ Not for the first time, I was lost for anything to say, so I reached out with the aim of putting my hand on her hip.
‘Not so fast. I’ve got someone who wants to meet you.’ She beckoned me in and through into her lounge – the room which looks out eastwards towards my own apartment.
Reclining on a white leather couch was another woman, ‘handsome’ I think is how she would be described; dark-skinned with a strikingly beautiful face and sturdy, muscular limbs. She was early 40s and clearly took good care of herself. She was dressed in a silk robe – this one was black – and was nursing a martini glass in one hand.
‘Hi.’ She said. ‘You must be Tom.’
‘Hi,’ I said, trying to hide my nerves. ‘I’m actually called Billy.’
‘Rapunzel said you were Tom, and I kinda like that better. Is that OK with you, honey? Can I call you Tom?’ Without waiting for a response, she continued.
‘Good. You can call me ‘Mommy’ like she does. So, Tom, this is what we thought would happen. You can fuck Rapunzel here while I watch. No holding back, though, young man; I want you to make a proper mess of her, and then – afterwards – I will clean her up. Alternatively, you can go home and spend the evening peeping through your telescope. What do you think?’
***
Shortly, I was naked as well, Rapunzel having assisted me in shedding my clothes into a heap on the polished wood floor. A baby pink chaise longue was positioned in the centre of the room, looking out across the expanse of the city. Rapunzel went to the switch at the side of the room, and soon, the window blinds were fully retracted.
‘You’re going to fuck her on the chaise, Tom,’ said Mommy. ‘You’re going to fuck her while I watch, and the rest of the city too; so, make a good show of it for us.’
Rapunzel arranged me on the chaise, facing out towards the rest of New York. She kneeled in front of me, between my knees and thrust her delicious ass towards the glass. I was almost sad that I wasn’t looking through my telescope: the view would have been incredible. The silky-soft hair fell across my thighs, and as she moved, it felt like a thousand gentle fingertips stroking my skin. My cock, initially struck with stage fright, began to grow. I looked downwards into the big baby-blues staring back at me as she swayed her head softly, aware of the effect that the waves of hair, brushing my skin, were having.
‘Can I begin, please, Mommy?’
‘Oh, yes. Make sure you get him good and hard now, like a good girl would.’
***
Rapunzel took a handful of her hair and began to brush the tip of my, now fully hard, cock with it. Jeez, I never felt anything so good in my life – it felt like my cock was being stroked by invisible fingers. Rapunzel took more of her golden hair and wound it around my shaft, all the while looking up into my eyes, never breaking her gaze. Placing her small hand around the cock, she slowly moved it up and down, wanking me, with the cushion of her hair feeling like satin as it glided across my skin. A bead of pre-cum trickled from the tip, and she caught it with her tongue.
‘Mommy, he tastes so good! Please say that I can taste him?’
‘Now, you’ve been such a good girl, but don’t spoil it all by getting all greedy. You know that’s Mommy’s special treat and she’s looking forward to it.’ I glanced across at the white sofa. The older woman was sitting now with her legs spread wide, her robe open, as she pinched and rolled a nipple between her fingers. ‘Don’t get him too excited now – he’s got to fuck you in front of the whole city first, remember? They need to see what a good girl you are – Mommy’s little slut – don’t they?’
‘Yes, Mommy. I’m sorry. Do you want him to fuck me now? If I keep going like this, I think he’ll just come all over my face?’
‘Well, that will never do, child. Come on, Tom, you’re up.’ Rapunzel stood, taking my hand, and helped me to my feet.
‘Oh my, Tom!’ Exclaimed Mommy. ‘You really are up, aren’t you? I almost feel jealous of my little slut here.’
***
Rapunzel positioned herself on all fours on the chaise, her hands gripping the headrest and her ass thrust backwards towards me. I tore my gaze away from her beautiful, creamy white globes to glance at Mommy. Her hand was between her legs now, and she didn’t attempt to disguise what she was doing. She let out a gasp as her fingers plunged into herself. ‘Come on, Tom.’ She exhorted me. ‘Don’t keep the lady waiting.’
I didn’t need any more encouragement. I took hold of Rapunzel’s hips, and she reached through her legs, taking hold of my cock and dragging it up and down through her dripping wet pussy lips. It was Rapunzel’s turn to moan now.
‘Come on, Tom. Get to work.’ Said Mommy. ‘And don’t forget I want you to make a mess of her.’
I pressed forwards against that glistening wet cunt, and my cock slid slowly in. She was tight but so wet that I was soon halfway inside her, and after pausing to relish the feel of her gripping my cock began to rock slowly back and forth.
***
At first, I moved only an inch or two, forwards and back. This felt like some kind of dream – a fairy tale – and I didn’t want to do anything to jar myself awake; I wanted it to continue for as long as possible. To the left, in the dimmed lighting of the apartment, I could see Mommy, stroking her wet cunt and squeezing her full breasts, and to the right was the expanse of the great city; lights, camera, action. I really did feel that I was in a performance of a sort. Give my regards to Broadway. The streamers of blonde hair fell about Rapunzel’s shoulders, pooling on the pink velvet of the chaise, a few locks lying along her back, falling between the warm globes of her ass, wet now with Rapunzel’s juices and clinging to my cock as I began to thrust full length into that tight little pussy that she was jamming backwards onto me. Our flesh met with wet slapping sounds as I made sure to get every last inch as deeply into my slutty little trumpeter as I could.
A flurry of gasps from the couch let me know that Mommy had just come off on her fingers. I had been desperately clinging to what self-control I had – not wanting for this to end, but I knew I was reaching the point of no return.
‘Mommy!’ Rapunzel’s voice was unsteady as she called out between gasps. ‘Mommy, I really want to come now. Can I come, please?’
‘Yes, you’ve been such a good girl for Mommy. Tom, it’s time for you too.’
I didn’t need any encouragement. Rapunzel began to jerk and twitch, and I felt her pussy clamping down on my cock as she was hurtled into her orgasm.
***
I could feel mine beginning to crest. Rapunzel was swearing at me now as she shuddered and shook.
‘Fucking give me it. I want your cum in me. Fill this dirty slutty little cunt with your spunk.’
My cock jerked inside her as I complied, jamming myself into her as hard as I could, pulling her back by her hips, impaling her as my shaft jetted hot semen deep into her.
We remained in that little tableau for a couple of minutes, gasping. When I pulled out, Rapunzel put her hand over her sex and wriggled around so that she was now lying on her back on the chaise, one leg up and resting on the back, the other foot on the floor.
‘I think Tom did well, Mommy. There feels like a lot, and I’ve saved every drop just like a good girl, just for you, Mommy.’
Mommy now rose from the couch and came over to where we were. She indicated the edge of the chaise.
‘Take a seat, Tom. You’ve done well, and I think we may need to make you a regular guest, but for now, take a load off and enjoy the view.’ She kneeled between Rapunzel’s legs, and Rapunzel removed her hand. Her beautiful pussy was sticky with a mix of our juices, glinting in the thousand lights of the tower blocks outside. A trickle of white emerged from the place which my cock had just now vacated, and Mommy fell upon it with her tongue like she hadn’t eaten for days.
‘Oh Fuck, oh yes!’ Rapunzel reached down and grabbed my hand. I held it, and she squeezed as I watched my come being eaten from her.
Love, Jaimie. xx
Links and Stuff
Retelling fairy-tales for an adult audience is nothing new and something I’m aiming to explore a bit more. I prefer the classics, but if you want a few recommendations for modern attempts at fairy-fucking smut, this might do the trick for you.
When I visited NYC with my better half, we walked the Highline, which was amazing – I highly recommend adding it to your ‘must do’ list if you ever visit Manhattan.
