Chapter 1: Breakthru
Castiel had never been lucky with love or sex. He had been in relationships but they always ended in boring dates, dissatisfying orgasms and ruined friendships.
Meg had been the first to his heart and to seduce him… then had proceeded to tell everyone he was bad in bed, but what 15 year old was actually good in bed? Meg's over-exaggerated three dollar hooker moans had put him off anyway and he hadn't even climaxed that first time but Castiel did learn to be more guarded with his emotions.
However disappointing his first time was, the memory of it had been enough to fuel his teenage brain into semi-satisfying orgasms when he had a spare moment and some Vaseline handy.
Next came Daphne, who had gone out of her way to get Castiel's attention all through high school but when he had given in their senior year he found her to be quite boring and obviously only dating him because of his prestigious Novak name.
Although he had found Daphne attractive (he found her green eyes to be quite alluring) their relationship was mundane and sex with her had been at best - adequate.
Whenever he would try to stray from the usual missionary - she would glare at him as if he was some sort of pervert. He once spent a little longer than normal cupping her ass, only to have her call him a deviant. He hadn’t let himself feel anything too deep for her so it was no huge loss when at the end of their senior year Daphne had dumped him, stating his ‘promiscuity’ as the reason, after he had gotten drunk and dared to ask her for a blow job.
He dated a couple more women much like Daphne in his first year of college, disappointed by the lack of imagination they all seemed to have agreed on when it came to fun and sex.
None of them came even close to making him feel anything for them. He wasn’t cold hearted, and he did genuinely want to experience falling in love or even just be in a relationship where he could feel comfortable enough to be himself.
Women seemed to find him attractive enough but Castiel wanted someone adventurous and curious.
It had been a far cry from his brother Gabriel’s college experience which seemed to entail every type of legal fornication plus a few that were borderline if his brother’s excited rantings were to be believed.
His next sexual experience had been at a college party where he had gotten ridiculously drunk and found himself the recipient of a sloppy drunk blow job being administered by an overly enthusiastic guy he vaguely recognized from one of his business classes. It should have felt weird and wrong to have a male so intimately engulfing his cock but it was the first time Castiel had felt a strong orgasm outside the ministrations of his own hand.
He entertained the idea of perhaps pursuing men but found there was no man he was particularly attracted to. Even the blow job guy - in the light of sober day - held no appeal. Castiel put the experience down as a clear indicator that he needed to start dating less prudish women.
His last girlfriend had been more or less forced onto him by their respective families. Hannah Chester was a Teaching Assistant at their Business School and had started off being as conservative as the others, much to Castiel’s disappointment, but had at least been curious enough to try new things when it came to food, music and movies.
Their sex life was more mechanical than intimate but Castiel, by that point, had resigned himself to the idea that love wasn't real, the best orgasms came from his hand (or unexpected homosexual blow jobs apparently) and that his relationship with Hannah would do as well as any other if he focused on his studies and prepared himself to run his father’s business.
A year into their relationship, Hannah left Castiel for a female student in one of her classes and Hannah’s family had accused Castiel of corrupting their daughter.
Needless to say, the Novaks did not receive a Christmas card from the Chesters that year.
"You know there was always something strange about that Hannah girl. Jaw too square, hands too rough." Castiel's mother took a deep drink from her wine glass as she swayed a bit despite comfortably sitting on an expensive leather armchair.
"And that grey lesbian suit jacket should have been a dead give away," added Gabriel as he poked and prodded the Christmas presents.
"Gabriel, get away from those!" their mother snapped, a little bit of wine sloshing on her pristine knee length skirt. "But it is rather rude of the Chesters to blame Castiel for their daughter’s deviancy - if anything WE should be the ones alienating THEM from parties."
She pursed her lips and made a small tut sound before taking another deep swig of wine.
"Aw, are the rich old coots not inviting you guys to their boring ass snobby hootenannys?" sing songed Gabriel.
"Honestly Gabriel, with the the way you talk - people probably think you were raised by wolves and sent to public school," their mother tutted again and slowly blinked while swirling the wine glass in her hand.
Gabriel rolled his eyes and continued terrorising the presents.
Castiel was just happy that they had ceased discussing his private life and he could continue browsing through endless dating profiles on his phone. He had taken part in four one night stands since Hannah, which, although debaucherously thrilling, still left him feeling dissatisfied in mind, body and soul.
The house phone rang and their mother shakily stood up to answer it.
As soon as she was out of earshot Castiel felt Gabriel slink uncomfortably close, no doubt to peer over at Castiel’s phone.
Before Castiel could tap out of the dating app, Gabriel looked up at him with a lecherous grin. "So baby bro, decided to play the desperate skank field before trying the ol' ball and chain gig again?"
"Not that it's any of your business but . . . well. . . yes," Castiel shrugged.
Gabriel straightened up and stretched. "Careful with that slope - those dating app skanks are kinky as fuck."
Castiel was definitely aware - his first encounter had been with a seemingly normal girl named April who turned out to be into extreme, dubiously consented bondage with a hint of blood kink.
Castiel wanted adventurous but April seemed a little too peppermint for his curiosities. "You've tried the app before?" he asked his older brother.
"Not that particular one but I've tried a few in my time, especially before Kali and let me tell you - I count myself as a pretty sexually adventurous guy but even I was scared off by some of those crazy chicks." Gabriel scratched his stomach through his blindingly loud shirt that Castiel knew was only worn to rile their mother up.
"I haven't had any truly horrible experiences as yet," Castiel said. Which was true, even with April, who'd called him vanilla for not wanting to try her messed up kinks, a first for Castiel.
Gabriel had poured himself some expensive scotch from the cabinet they weren't supposed to take drinks from. "Oh? So you've actually met with some already?"
"Yes, four actually," Castiel said, while safely stowing his phone in his jacket.
"Haha Cas! You dog!" Gabriel sat in front of Castiel with crossed legs and a straight back. "Well, how were they?"
Castiel rolled his eyes at his brother and crossed his arms. "Gabriel, I'm not going to go into detail about my sex life with you."
"Ok fine, just give me a run down, then. Yes or no answers only," Gabriel suggested excitedly.
That sounded . . . reasonable. "Um . . .ok"
"Did they give you head?"
"Gabe," Castiel pinched the bridge of his nose suddenly feeling very tired.
"C'mon - yes or no?"
Castiel sighed. "Yes"
"Did they swallow?" Gabriel asked with a suggestive eyebrow.
"Um. . . no." Castiel had to think about that one because there had only been one blow job worth remembering in his life and none of those girls had provided it.
"Did they want to do any crazy stuff?"
Abort, abort, Gabriel could NOT know about April. "No. . . "
"Ok, I don't believe THAT for a second, but I'll let it go for now . . .hmmm." Gabriel leaned back on his elbows with the tumbler of scotch next to him. "Did you go in the back door?"
"Yes with one of them," Castiel answered without realising and instantly felt a blush take over his face.
"Haha awesome. . . did you let them do butt stuff to you?"
Gabriel raised the more lecherous eyebrow of the two.
"No! Of course not!" One of them had suggested butt stuff and although Castiel had been slightly curious about prostate orgasms for a while - a one night stand didn't seem like the right time to explore that.
"Ok ok." Gabriel held his arms up in mock surrender. "Were any of them squirters?"
"Um, I don't think so."
Gabriel's smile faded as he picked up his tumbler of scotch.
"Well this was less fun than I thought it would be. Um. . . Was your relationship with Hannah a front for her lesbianity?"
"Wait. . . That wasn't a part of -"
"Yes or no, Cas?"
Castiel folded his arms over his chest again, much like a petulant child. "Lesbianity is not a word and no, it was a real relationship as far as I was concerned."
Gabriel's brows creased in displeasure. "Did you know she ate carpet while you were dating?"
"No." And he didn’t – he had no idea. Castiel thought they had been pretty open with each other about most things and if he was hurt by anything about their break up it was more that Hannah hadn’t trusted him enough to tell him of her preferences.
Gabriel looked down at his scotch and hesitated before asking "Did you. . . love her?"
". . . No." He didn't.
If he were to describe their relationship it would have been closer to a friendship . . . with obligatory relationship sex thrown in to keep up the charade.
Gabriel genuinely smiled at Castiel. "Well I guess I'll have to cancel the flaming poop I had planned to send her then."
"Haha nothing. Hey, so I got you a special present that mother can't see. . ." Gabriel gracefully popped up into a standing position despite being on his fifth scotch of the night.
"Um ok?" Castiel had always been cautious of Gabriel’s “gifts” since that time he had managed to rig a blow up doll to inflate when Castiel pulled the bow of a gift box.
Gabriel took out an envelope from the back pocket of his pants and handed it over to his younger brother.
Castiel opened it to find a cruise ship ticket but not to the fancy 'networking' ones his parents were always trying to push him into going on. Instead, it was one of those bawdy singles mixers he's heard his friend Balthazar talk about where everyone is drunk the whole time and having sex everyday with strangers.
Castiel was confused by the gift, sure, he spent an obscene amount of time thinking about sex but apart from the candid conversation he had just had with Gabriel, the general consensus was that Castiel was as vanilla as they came.
"Gabe, I Uh-"
"No need to thank me - I feel it my duty to school my little brother on the finer craft of banging skanks . . . Even though you finally seem to be doing a good job of that yourself," he added with a wink towards Castiel.
"I can't justify a week off work plus, mother would find out and that's just all kinds of embarrassing." Even as he provided excuses of why he shouldn't go, Castiel’s interest was definitely piqued.
Gabriel's expression turned into something that Castiel could only describe as 'scheming.' "Hmm I'm not hearing a no . . .which is more than what I thought I'd have to work with."
Gabriel sat down in the armchair their mother had been occupying. "Well, taking the week off is actually the easiest part of this considering you're the boss there and mother and dad - well, we'll just tell them the same thing I told them when I went on the cruise."
Castiel felt his face crinkle in concentration trying to remember when Gabriel was absent for a week but could only think of that time he broke his leg while on a skiing weekend and had to stay because he couldn't travel. . . wait.
"Ah there it is, and no I didn't break my leg - but I did spend the week in bed." Gabriel waggled his brows at Castiel as he poured himself another drink.
Castiel looked down at the ticket in his hand, maybe he could go on the cruise, have a week of kinky sex and get it out of his system. Then. . . then what? Marry a boring woman his family approved of and father a couple of kids into a loveless lacklustre marriage? Depressing didn’t even begin to cover that outcome.
"What's wrong?" Gabriel's voice cut through Castiel’s sudden melancholy.
"Nothing, thank you Gabriel, I'll think about it." He offered his brother a grateful smile and folded the envelope into his jacket pocket along with his phone.
A shrill voice sounded from the other room. "Fine Roger, if you don't want to spend Christimas eve with your family. Fine. . . . I'm fine. . . No, I'm not angry, I'm just tired . . . Hmmhm. . . Ok goodbye husband." Their mother appeared in the doorway. "Your father is fucking his secretary this Christmas eve but will be gracing us with his cheating presence tomorrow for lunch."
Castiel winced - not at the language or even the subject, but because their mother's attitude meant that she was very drunk and close to that scary point where she started crying and talking about men that wanted to marry her before she had chosen their father.
"Mother, with a mouth like that people might think you went to public school and were raised by-"
"Gabriel please, I have too much of a headache to deal with your so called wit." She held her temples and scrunched up her face.
As a fellow veteran of their mother's drunken moods, Gabriel sighed and was by her side in a few strides and cooing sweet words, encouraging her to go to bed.
She didn't put up much of a fight but before she let Gabriel help her up the stairs she turned around to face Castiel. "Castiel, one of your father's business partners is coming to Christmas lunch and he's bringing his family along. He has a daughter named Tessa who I think you should speak to. She's very bright and has expressed an interest in meeting you," his mother sniffed nonchalantly.
"She reminds me of myself at that age, determined and beautiful with so much promise," she said almost wistfully.
Gabriel rolled his eyes and gently guided her elbows towards the staircase. "Alright drunky, time for bed."
"Gabriel!" their mother snapped.
Castiel could hear the echo of Gabriel's giggles up the stairs. Great, he thought, he now had to deal with yet another 'family approved' set up. He knew if he really didn't like the girl nobody could technically force him to date her. But he would have to put up with his mother calling him everyday telling him how he was wasting his life, and how their brother Luke had been set up with his wife Lilith, and they couldn't be happier and the only way he would be happy too was if he started a family of his own. Which of course was a big fat hairy lie, made glaringly obvious by what had transpired between his parent just moments ago.
Suddenly the cruise didn't sound like something he should be making excuses for. What if there was a girl on the cruise that also came from an affluent family but was looking for a last hoorah before she settled down with some boring preppy guy that was going to cheat on her with his secretaries?
Castiel slumped back into his armchair with a sigh. He was obviously overthinking the situation.
Gabriel came down the stairs smelling distantly of potpourri. "Drunky had a bit of a barf but then went to sleep, she'll be fine for lunch tomorrow."
Castiel scrunched his nose up and rubbed his face suddenly feeling exhausted again.
"Hey Glummy, have a drink, it'll be fine. I've heard Tessa is pretty hot." Gabriel downed what was left of their mother’s wine in one obnoxious gulp.
Castiel felt a ripple of annoyance. "Ugh she could be the most beautiful woman in the world and it wouldn't matter if she’s as boring as dishwater."
Gabriel looked over at him with surprised eyes and then burst out laughing. After his amusement had trickled into small giggles he finally said "Maybe you could find someone like my Kali? Y'know long distance, see each other once a month to fuck like bunnies and then get to tell our respective families that we're in a relationship."
"I think you lucked out there," Castiel tried to say with as little sarcasm as he could muster. Kali was actually terrifying, he hated to think what sex with her must be like. That being said, she had always been kind to him despite their first meeting consisting of Luke introducing Castiel as ‘their repressed little brother’.
In a rush of impulse Castiel finally made a decision. "Gabe. . . I'm going on the cruise."
Gabriel turned around again and walked up to Castiel with a grin on his face. "Atta boy!" Gabriel smacked him on the shoulder. "Get ready to see more pussy and wang than you'll ever see again."
"Gabriel, ew." Castiel scrunched his nose up again but the more he thought about it. . . it didn't actually sound so bad.