*deep breath*

I'm sure some will have strong feelings on this fic, but... I loved the prompt, I'm pro-sex workers and I've had a bunch of prompts for Hiccup x all the female characters. Where possible, the chapter names will have the ship in that chapter.

Hiccstrid are still a couple, they just have their escort jobs too. It's not that tough.

All ships will be heterosexual (I know!)

For starters?

Hiccup x Heather!

-HTTYD-

Phone alarm trilling, Hiccup checked the work calendar pinned to the wall. Heather, 18:30, six hours.

"Time to get ready for work babe?"

"Yep. Gods, what is it with women wanting me to take them dancing?"

Astrid laughed, watching Hiccup as he opened the wardrobe and picked out his green suit. Apparently it brought out his eyes, but equally important to him was that it was comfortable and didn't make him feel suffocated.

"Dancing is sweet and very... date-y. Teaches you if the other person is shy or confident, shows that you're able to be close to them without feeling nervous. Old fashioned courting. Shut up and be the fantasy."

His girlfriend was unsympathetic, laughing as Hiccup hung the suit on the door, checked his boots were polished and picked out his 'fancy pants' underwear.

"Are you working tonight? You haven't hung your calendar back up."

She'd taken it down to fill in planned shifts.

"Yeah, but only as an accompaniment tonight. Some poor guy who didn't want to go to the theatre alone but can't talk to girls."

"I'm sure you'll fix that" Astrid winked, watching him undress "but it sounds very cultured. I'm going for a shower."

He scrubbed himself thoroughly, made sure he'd shaved down to only the habitual stubble that helped him not look about six years old. His hair was hopeless as ever, but that was nothing new. Astrid resided on the bed holding his pants hostage until he kissed her, which Hiccup offered her willingly.

"Love you. Now get dressed for your date."

"Love you too."

Astrid was just selecting her outfit when Hiccup was dressed and ready to leave. He admired the deep red dress she chose, knew she would look utterly sensational when she headed out as some strangers date that night. He dabbed a little aftershave on, and Astrid sniffed him before humming in approval.

"Nice. Got your condoms?'

"Always."

Hiccup patted his suits inside pocket, then his trousers and finally the extra one in his wallet - it was changed out regularly to ensure it wasn't damaged. Astrid winked, kissed him goodbye and shooed him out of the door. Heading up to his car, Hiccup smiled at the shiny exterior of what was almost his most prized possession.

His job paid very well, and while Hiccup wasn't one for an extravagant lifestyle he couldn't resist the 'Night Fury' car and splurged on that and that alone. The only other real expenditure he had was the clothes, but tonights job alone would have paid for his suit and left spare change. Plus, this one was wanting for a proper date. Hiccup wouldn't dare short-change a customer on what they wanted. Elda, the woman who ran the agency he and Astrid worked for, even asked clients for a list of conversation subjects. This particular woman was in to wild camping, mythology and Viking tribes, apparently.

He popped in a breath mint on the way, though he had brushed his teeth earlier. Pulling up outside the bar Heather had asked him to meet her at, Hiccup slid from his car, brushed down any dust from his suit and checked his aftershave was still detectable. Satisfied he was presentable, Hiccup scanned the people illuminated by street lights that had flickered on as evening began to fall.

Spotting who he was pretty sure he was there to meet, Hiccup gave her the once over. About his age, built fairly similarly to Astrid and with pretty green eyes, a long dark braid hung over her shoulder. He felt in his pocket for his trademark, then approached.

"Heather?"

Green eyes narrowed slightly in suspicion, but Hiccup was used to that when approaching who was effectively a stranger.

"Who's asking?"

"I'm Henry."

When her face cleared, he smiled and she returned it. Hiccup withdrew the rose from his pocket, gentle to avoid crushing it - he always brought one on dates. Heather smiled prettily as she took it, walked ahead when Hiccup held the door open for her.

"Shall we?"

He never drank alcohol, nursed an ice water at the bar after buying Heather a drink. He always kept an eye on his 'dates' consumption too. Heather clearly needed to calm her nerves a little though, so her vodka and cranberry juice ought to help there.

"So Heather, what do you do for a living?"

"I work with endangered animals."

"Really? My mom works with animals too."

That part was true, but after one or two slightly obsessive customers Hiccup was very selective with any further details he gave and had pre-rehearsed answers for questions about his life, job, childhood and so on.

"Yeah? That's pretty cool."

By the time she'd finished her drink and they'd talked the whole time through, Heather was starting to come out of her shell and Hiccup now knew she was frequently busy with work, and didn't have much time for dating. He also learnt that she kept reptiles as pets, had an older brother and really liked extreme sports.

"Me and Dagur like mountain biking."

"On actual mountains?"

"Yep."

"Wow. I'm a little clumsy, it sounds like I'd get hurt."

A lot of his job was psychology; Hiccup paid attention to how a person responded, adapted his behaviour and attitude depending on that and once Heather got to talking, she was quite happy to lead the conversation. After her second drink, rather than make a comment about wanting her sober for 'later', Hiccup gestured to the wide open space with soft lighting and melodic music.

"Would you like to dance?"

He knew she would; it was in his job description for the night but he couldn't exactly say that. Heather nodded and he smiled, threw in a little bow as he reached for her hand and led her to the specially designated dance area. Heather was quite tall, and Hiccup had taken dance lessons with Astrid but he reckoned he could manage it.

"You're a good dancer."

"Thanks. You're not so bad yourself."

Heather seemed quite content to all but melt against him as they stepped and swayed to the music, blending in with the other patrons who were out on dates too. The soft lighting reflected off her silver skirt quite well, giving her lower half an almost ethereal glow whenever a particularly bright beam hit the material.

"Can I ask you something?"

"Sure."

She peered up at him through her eyelashes, and Hiccup worried for the concern in her expression.

"Do you think people who do this are pathetic?"

Hiccup raised an eyebrow.

"Dancing?"

"No. Buying a date."

"O-oh. No! Not at all. People get lonely, and that's not a weakness or pathetic. You're allowed to want things like dates and dancing and stimulating conversation, and if you don't have the time to look then I'm just more convenient. People all over the world pay for convenience every day. It's no different than... buying a dishwasher."

Heather started laughing, leaning against him and he was happy to see her smiling again.

"So... you're a dishwasher?"

"Exactly. I'm a dishwasher."

Having worked up an appetite twirling around the dance floor, they headed over to the bar to obtain food. He remembered to pull her chair out, which made her smile. Heather ordered a hearty meal while Hiccup stuck to a light salad and chicken, not wanting to risk being bloated later.

Now past any residual awkwardness, Heather went back to opening up in conversation, chatty and happy again as they worked their way through their meal. Hiccup sipped his 'mocktail', really just a combination of fruit juices with a paper umbrella in designed to look as though he was totally a grown up totally drinking alcohol.

"Do you want to order dessert?"

Heather swirled her straw around in her glass, remnants of mostly-melted ice clinking against the inside of her glass.

"Yeah, but how about to go?"

Hiccup couldn't really miss her playful smirk, pretended to think about it.

"Where are we going?"

Heather pretended to think about that too.

"My place?"

He returned her smile.

"Lead the way."

Heather ordered dessert while Hiccup settled the bill, which was included in his price after all. As they left, Hiccup enquired about her travel.

"My brother drove me, wanted to check you were who you were meant to be since I told him it was a blind date."

"Ah. Well I drove here, I'm happy to drive you home."

Grinning, Heather whistled lowly at his car.

"Wow. Nice wheels."

"Thanks. Kind of my pride and joy, but that's what happens when you like engines."

Heather directed him toward her home, assuring him that no angry big brother was waiting to ask about his intentions toward Heather. Her dessert sat on her lap in a box, waiting to be opened up devoured. Probably much later, as some kind of post-coital treat. Hiccup shot a glance at the in-car time, saw there was still a good two and a half hours left 'on the clock' with Heather.

Plenty of time to ensure she got her money's worth then.

"Here, this is me."

They pulled up outside a little quaint two-bed, garden a little overgrown but not totally out of control. It was more managed than his parents garden got sometimes anyway. He saw a silver car tucked in at the side, followed Heather up the garden path with gravel crunching underfoot. She asked him to hold her sweet treat so she could look for her keys, letting them in to her home and Hiccup immediately detected that smell that meant this girl cooked. Or someone she lived with did, but she hadn't mentioned a roommate.

"Do you live with someone?"

"Not at the minute, my roommate moved out to get married. Why?"

Hiccup restrained himself from making the sort of remark he would to Astrid about noise disturbance, and shrugged with a smile.

"Just curious."

Heather saw right through him, putting the pudding box in the fridge and turning to him with a smirk.

"Mhmm."

Hiccup tried to keep a straight face, but found himself laughing along with her when Heather began giggling. He undid his jacket, folded and hung it over the back of a kitchen stool. That was why he kept condoms in jacket and trousers. He loosened his tie just enough to pop his top button open, watched as Heather followed the line of his neck revealed.

"Can I get you a drink?"

"Water would be great."

Heather filled a glass for him, handed it over and Hiccup sipped it in a bid not to spill any down his clothes. It had happened before. She was notably tense and Hiccup had a pretty certain inkling as to why; it was a frequent awkward point on his 'dates' where the lady wasn't sure how to transition from dinner and drinks to sex. Hiccup used to be that awkward, and sympathised hugely.

"Want to come sit down?"

He took her hand gently, led her to the living room he'd spied on the way in and got her to sit on the sofa with him. Heather came along quite happily, perched next to him and Hiccup could Ser how she looked at his mouth.

"May I kiss you?"

Teenage Hiccup would never have believed adult Hiccup could be that smooth and confident; he would have stammered and blushed and expected the girl to laugh in his face. That thankfully didn't happen, and Heather didn't even bother to say yes - she kissed him.

Hiccup had kissed quite his share of ladies now, but still found that everyone was different. Some were shy and tentative only to turn out rough and hungry. Others were methodical and measured, took time and arousal to let go and attack his mouth needily. He could taste the remnants of Heather's fruity cocktail on her lips, sweet and sharp. When Hiccup wasn't pushing toward deeper kisses, Heather quickly moved to a more demanding stance, tugged his tie and pressed herself closer.

Surprisingly sure fingers unknotted his tie and tossed it to one side, starting on the buttons of his shirt. Hiccup always liked the ones who didn't take long to come out of shyness into want. He also liked the women who were slow burners, hesitant until their arousal overwhelmed.

It was just sex though; they weren't Astrid. He knew she felt the same about her work too.

Compartmentalising his relationship for the moment, Hiccup pulled back to watch Heather gasp for breath, green eyes dark and dilated, cheeks faintly flushed and chest heaving against her dress.

"Upstairs."

"Hm?"

Heather stood up, grabbed his hand.

"Upstairs. Bedroom."

Hiccup stood, grinning.

"Lead the way."

Her bedroom was a testament to her interests, those plushie animals one got from conservation charities perched up on one shelf, another with little figurines of Viking gods and goddesses. Her bedsheets were black with silver runes patterned over them, which Hiccup only had a second to notice before Heather and he were hitting her bed. There was something to be said for hired dates; Hiccup never wondered what the evening was expected to end in. Of course, there were times he could tell the women weren't certain about going through with it, and did his best to put them at ease or assure them there was no obligation.

So far, he wasn't terribly worried about either situation with Heather. If anything, he was considering slowing her down before she tore something going for his belt. He gripped her wrists and moved her hands to her side, tried to talk soothingly.

"Relax, there's no rush."

"You say that but I have a time limit and intend to have you at least twice."

Hiccup chuckled, dropped a hand to the side of her knee.

"I shall endeavour to meet your demands, but I'd hate to ruin such a nice dress."

The silver material felt almost impossibly soft beneath his fingers, slid up over pale skin dotted with the occasional scar Hiccup expected on someone who worked with animals. When stripped of her dress Heather was somewhat shy again, but Hiccup was well-versed in helping someone feel more comfortable with their body in bed. It was an essential skill.

"Come kneel here for a minute."

He stood at the foot of the bed, had Heather kneel facing away from him so he could untie her hair braid. Combing his fingers through the strands had the desired effect of making her relax, making his way up to her scalp to rub soothing circles there. It was immediately apparent Heather was sensitive there, effectively melting against him as Hiccup caressed delicately, low groans leaving her mouth that stirred Hiccup's own lust.

"Better?"

"Mhmm."

Shirt already hanging open, Hiccup slid it from his arms and hoped it wouldn't pick up loads of carpet fluff from the ground as it fell. Then he ran his fingers down the middle of Heather's back, enjoyed her shiver and sharp exhalation. Hiccup could undo a bra in his sleep, blindfolded and one handed. Knowing they were not exactly a comfortable garment, when Hiccup had slipped the straps down her arms he placed fingers on her shoulders, squeezed and massaged any residual tension away.

"Gods that's good."

"Can't have you all tensed up, then you'd not have any fun at all."

Hiccup encouraged her to lean forward a little, fairly sure that once she got into stride Heather wouldn't want to go slow, but until then he was going to build the fire gradually. He kissed the back of her shoulder, ran the tips of his fingers over her side and she trembled under such minor ministrations. Responsive... Hiccup took note, continued to explore the more low key areas like her back and stomach, avoiding anywhere too sensitive or direct until he was satisfied she was close to losing control.

Sure enough, Heather lost patience with his slowness and, with a speed he hadn't expected, turned and pulled Hiccup back to the bed. Down to only cute black briefs with a picture of a polar bear on, Heather crawled on top of him, straddled narrow hips and ran her hands over his bare torso. Hiccup had always been and would always be rather skinny, but adulthood had filled him out a little and curious hands explored lean muscles.

"Not that that isn't wonderful, but would you mind if I moved to get my boots off?"

Heather mock-grumbled, but slid fluidly from his thighs to let Hiccup sit up, lean forward to remove shoes and socks, sighing happily at the feel of a cosy carpet beneath bare toes. Lips curved up in a mischievous smirk touched Hiccup's back, nipped at his shoulder blade and wrapped herself around him from behind. Her bare breasts were hot against him, swollen nipples dragged against skin as slim hands dropped to his belt buckle again. This time he let her undo it, lifted his hips to wriggle out of his bottoms.

"It's a nice suit but it has definitely served purpose."

"If you say so."

Hiccup plucked the condoms from his pocket and tossed them further up the bed, twisted to resume kissing Heather until she was reduced to gasps and whimpers again. Her underwear was damp against his own, her hips pushing up against his erection as though seeking evidence Hiccup wanted her.

"S-slow down a little."

"Done that. Now is time to get a move on."

If he had any doubts, Heather's eagerness to strip them both of underwear put paid to them. He had to almost pin Heather down to check she was aroused enough to take him, got a petulant growl when he insisted on ensuring he wouldn't hurt her. Satisfied she was more than wet enough, Hiccup tore foil and sheathed his erection, found long slim legs wrapping tight around his hips in Heather's haste to get to the main event.

"Fuck, I needed this."

Hiccup didn't say anything, waited for that initial instinctive tensing against the new feeling to pass so he knew Heather was comfortable enough for him to move. He moved with measured slowness, made note of her responses and which angles made her moan, shake, clutch at his upper arm. Then he could focus on those particular motions, focus on pushing Heather to a state of quivering need and desperation.

Given that Heather had made it clear she wanted a round two, Hiccup didn't feel too bad about the first time coming close to being over too fast. If anything, it ought to take the edge off for her. When she tugged his hair and bit his lip, back arching as she moved with him, he could feel her grow tighter and hotter, knew she was close.

"Fuck... Henry, gods that's good!"

That was a clear distinction for him between any who weren't Astrid; Astrid called him Hiccup in bed and he liked it. Henry was his work name... it was fairly vanilla but then he wasn't a porn star.

Sliding his hand over her belly, Hiccup stroked her clit and Heather needed little more stimulation before she came with a shout, curling up into him as she shook and fell limp, breath ragged and quick.

"By the gods I needed that."

Hiccup winked.

"Hope you don't think we're done yet."

Heather laughed lightly, watching as he pulled out and removed his condom; he hadn't come yet but that wasn't uncommon for him, especially when he knew he was going to go again later.

"Where you going?"

"To get you some water, I won't be long."

He pulled his boxers on, padded downstairs and hissed at the cold floor beneath his bare feet on his way to the kitchen. Rehydrating himself, Hiccup took a full glass up to Heather who looked quite happy to see it.

"Thanks."

"No problem. You looked thirsty, and besides" Hiccup climbed back up onto the bed with a grin "you needed a little time to not be oversensitive."

Eyes widening at the implication, Heather placed the glass aside as Hiccup stretched up to kiss her; he'd checked. They still had the better part of an hour. Plenty of time for him to deliver a better second round.

Hands roved spots he already knew she liked, made Heather squirm beneath his touch as his mouth explored her neck, slid over her collarbone to reach her chest. Her breasts were by no means large, but they suited her frame, were soft and plush beneath his hands, his mouth and Heather bucked and cursed when Hiccup tongued a swollen nipple. One hand fisted in his ridiculous hair, tugged when Hiccup went too long without giving the poor girl a chance to breathe.

Her pale thighs trembled against his, parted instinctively when Hiccup placed a hand there to spread them wider. Heather was hot and soaked already, lax with the previous climax and permitted two fingers easily. He couldn't keep the smirk from his face when crooked digits found the right spot, dragged across it to make her shake harder. A thumb circling a swollen clit had her close to growling again, wonderfully devolved from the nervous girl that he had started their date with.

"Stop being such a tease!"

"Where's the fun in that?"

Heather dislodged his hand and leapt at Hiccup, pinning him on his back with a sudden strength. His boxers didn't last much longer, slick fingers struggling to place the latex correctly but Hiccup was pretty adept at such a task. Satisfied it would stay on, he let Heather set her own pace as she seated herself on his cock. Left wanting for a while, now he was the sensitive one and Heather was not in a forgiving mood after he had tormented her so.

Still, she certainly seemed to enjoy using Hiccup to fuck herself hard and fast, and he simply held on for the ride by gripping slender hips or touching tightly muscled thighs. Hidden strength was belied by her slim body, but Hiccup could sense it in her movements, felt it when Heather leant forward to brace herself against his upper body and could hold him in place with almost frightening ease.

Heather's grip on his skin wasn't perfect; both were sweaty, messy and beginning to crumble beneath the pleasure shared between their bodies. She slipped, fell forward and didn't bother to correct herself, used the angle to rut and grind harder against him. Hiccup felt her convulse and spasm against him and was struck with relief that he no longer had to hold back, shared in the thrill of climax, only moving to ensure he didn't lose the condom but, as a gentleman, offered the cuddling afterglow.

Like Astrid said; he was supposed to be the fantasy and Heather had wanted to ease her loneliness. She laid against him for several minutes, finally yawning into her hand.

"Tired?"

"Mhmm."

"If you want, I'll stay until you fall asleep, then let myself out."

"Really?"

Hiccup nodded; the time differential between her time being up and when she fell asleep was going to be minimal at best. He even tucked her in, stroked her hair lazily until her breathing evened out. Hiccup redressed quickly and quietly, cleaned up his condom rubbish and dropped it in the bin downstairs. Retrieving his jacket, Hiccup locked her door behind him, posted her keys through her letterbox and headed to his car.

Astrid had left him a text to say she got home alive and un-murdered (a running joke between the escort couple, whoever finished first that night sent it), and Hiccup fired one back to say he was just about to drive home. She replied with a promise to run him a bath, which Hiccup knew full well meant she would be getting in it with him. Maybe even already waiting in it when he got back...

-HTTYD-

This will be updated... whenever I have time and inspiration I guess.

The chapters will run Hiccup, then Astrid but there'll be Hiccstrid-centric chapters littered throughout. If you have a pairing request, feel free to drop it. Might happen, you never know!