A gay story: S.L – The Boyfriends Author’s Note: This is a standalone story, however follows characters first introduced in ‘S.L – The Pretty Boy’ so read that one first if you’d like to know their backstories. This is a smutty fantasy so please do not read if you want realism. All characters in this story are 18 or over.
This is part of the ‘Sapphire Lane’ universe which is a collection of various stories all set on Sapphire Lane, or at the nearby Ginerva Academy and Violet Liberal Arts College.
The Story
Caidan rushed into his apartment, late home from his work at a coffeehouse. He was going out for dinner with his girlfriend and one of her friends who also was bringing their boyfriend, and he only had half an hour to get ready. He quickly showered then dressed in a white shirt and black skinny jeans, and checked his hair in the mirror. He was twenty two years old, with a slim figure, pale skin, and attractive thin face with a nose his girlfriend always said was pretty. His wavy black hair was cut short in a pixie cut.
He still couldn’t quite believe he had a girlfriend, as he was openly gay however had met her in unusual circumstances at a queer bar. He had mistook her for a femboy twink, while she thought he was a boyish lesbian so after dancing and kissing, they had gone back to her college dorm where they realised their mistake however decided to have sex anyway.
Neither of them had been ‘turned’ straight by the experience however they were undeniably attracted to each other so he saw her as his ‘little freckled prince’ boyfriend whereas she regarded him as her ‘pixie cut princess’ girlfriend, so despite their relationship being technically heterosexual, it was uniquely queer.
Ready, he rushed back out of his apartment to hurry to the restaurant.
****
The restaurant was Italian, with cosy rustic décor, and Caidan spotted Casey, his girlfriend, sat at a table in the back. Next to her was a blonde girl, presumably her friend who had come up to the city to visit her at college, while her boyfriend was sat with his back towards Caidan so he couldn’t see his face.
Casey saw him as he approached and waved. “Fashionably late…” She teased Caidan then introduced him to the table. “This is my friend Amy, and this is her boyfriend Mathieu.”
“Nice to meet you both…” Caidan smiled, a little taken aback when he saw how attractive Mathieu was. He was perhaps the definition of a pretty boy with flawless lightly tanned skin, youthful face with a sweet smile, slender body, and dark brown hair cut in an androgynous chin length bob. Caidan thought he looked far too pretty to be straight, and wouldn’t of believed it if he wasn’t sat with his blonde girlfriend.
They ordered their food, a mixture of pasta dishes and pizza, as well as a bottle of red wine. Throughout the meal they chatted and joked, with Caidan trying to hide his captivation with the other boy who he found spoke with a soft French accent.
Casey and Amy led most of the conversation catching up about their different colleges, and reminiscing about their high school days. As they chatted, Caidan accidentally knocked someone’s foot with his, and murmured an apology that might have been lost under the noise of the girls’ chatter and dim of the restaurant, as he felt a foot gently tap him back, then tenderly rub against his calf. The angle meant it was impossible to have been Casey’s foot, and besides, it felt like a male shoe rather than a high heel so didn’t seem to be Amy neither which just left Mathieu.
He subtly glanced across the table at the boy, who seemed to be focusing on the girls’ conversation but Caidan was sure the boy flashed him a little smile. Intrigued, and hoping it really was the boy and not his blonde girlfriend, Caidan carefully slipped his foot out of his loafer shoe, and carefully found the other person’s foot again. He rubbed his foot, covered by his sock, against the person’s ankle, discreetly caressing it with his toes, and was excited to feel a trousered leg, rather than one enclosed in tights, so knew it was indeed Mathieu, and not Amy, he was playing footsie with.
He glanced at the boy again, who seemed to be blushing a little however didn’t give their secret game under the table away though twisted in his chair slightly, with Caidan guessing the boy must also be slipping a foot out of his shoe. Sure enough he felt the boy’s toes nudge against his own foot, then move up to caress his ankle and calf though his skinny jeans, then even higher to playfully tap his knee.
The secret under the table flirting was interrupted with the arrival of the food, and Caidan slipped his foot back into his loafer, though was excited by the experience, wondering what the boy’s sexual orientation was as it wasn’t normal behaviour for a heterosexual boy, sat with his girlfriend who was a conventionally pretty girl without the tomboyish gamine features that Casey had, to play footsie with another male.
****
As Casey’s college campus didn’t allow boys inside, they instead went back to the hotel that Amy and Mathieu were staying in, stopping in a corner store to grab some bottles of wine. The hotel room was quite small but had a little sofa which Caidan found himself sat on next to Mathieu while the girls lounged on the bed.
Drinking the wine, they soon found themselves playing a game of truth or dare with Amy proving herself quite lewd when tipsy.
“Who tops out of you two?” She asked Casey who had chosen a truth.
Casey laughed. “I do… I brought my own strap-on as I was needing to borrow one belonging to my roommate too often!”
Caidan blushed a little, but found himself excited to have it revealed to Mathieu that, despite being with a cis girl, he still took cock. He wondered if the boy ever got pegged by his girlfriend, and decided he’ll try to ask if Mathieu or Amy picked a ‘truth’. He didn’t need to however as Casey asked the same question to Mathieu.
“I top…” The boy began but Amy cut in. “…but I’m the dominant one, perhaps I should invest in a strap-on like you!”
After a few more questions, as most of them were picking ‘truths’, Caidan got his chance to ask Mathieu something. “Have you ever kissed a boy?”
The pretty boy blushed, and nodded. “I experimented a little in college before I met Amy, and my first kiss in school was with a boy too so consider myself bicurious if not bisexual.”
This response pleased Caidan, though didn’t surprise him after their subtle footsie flirting in the restaurant. Despite both of them having a girlfriend, he couldn’t help wondering how bicurious the boy was feeling tonight, and absently mindedly picked ‘dare’ when Amy asked him.
“We’ll put it to the test. Kiss Mathieu… with a bit of tongue.” Amy grinned, and Casey giggled at the audacious dare.
“If Mathieu doesn’t mind?” Caidan said, hoping the boy wouldn’t but not wanting to come on too keen. The boy shrugged with an easy-going smile. “I don’t mind, just for fun but I think if we kiss the girls need to kiss too!”
“Deal!” Amy agreed without hesitation.
“I didn’t think you had any interest in girls…” Casey teased.
“Don’t flatter yourself… I just want to see the boys kiss!” Amy laughed.
Caidan turned to face the other boy on the sofa, a little shy now it was actually happening especially with the two girls watching from the bed. Mathieu grinned and reached out, gently putting his hand on Caidan’s cheek then leaning in to kiss the boy. Their lips met, softly at first as they lightly kissed but as they grew more comfortable, their lips slightly parted to kiss more deeply. Caidan ran his fingers through the boy’s dark brown hair, then caressed his slender neck before running his hand over the boy’s flat chest.
Caidan got more daring, and flicked the tip of his tongue over the boy’s bottom lip, as Amy had dared them to include tongues after all, and was excited to feel Mathieu respond with his own tongue. Their lips parted further with the kiss deepening as their tongues darted into one another’s mouths.
“I think they’ve forgotten it’s just a dare!” Amy exclaimed, and both blushing a little, the boys broke their kiss however if not for the blonde girl’s intrusion, it was clear they both would of continued.
“Guess it’s our turn now…” Casey giggled, sipping her wine, then kissing Amy. Caidan watched his gamine girlfriend kiss the blonde, the girl clearly making the most out of the opportunity as he had with Mathieu, though he had to suppress a surprise twinge of jealously. It was strange but he found seeing Casey kiss someone else made him desire his ‘little freckled prince’ even more, however that evening his desire was divided between her and the bicurious fem boy sat next to him on the sofa.
Though he loved being pegged by his girlfriend, he couldn’t help fantasising about what Mathieu’s cock, flesh rather than synthetic, would feel in his mouth or butthole. He was surprised to feel the boy gently kiss his cheek, and turned towards Mathieu who kissed him on the mouth again before he could speak. He kissed back, even though they no longer had the excuse of the dare, and felt the boy’s warm wet tongue in his mouth again. For someone who had seemed a little shy and quiet, the boy was certainly proving he could be direct!
“Hey, they’re at it again!” Amy said, when her kiss ended with Casey and the girls saw the boys were kissing rather than watching them.
“Sorry, guess we just felt left out seeing you two kiss…” Mathieu shrugged with a naughty smile. They continued to play truth or dare, until Mathieu asked everyone who they would use a free pass on to fuck if given permission by their partner.
Amy named a college professor she had a crush on, but Mathieu surprised them all by smiling naughtily and naming Caidan.
“Get a room!” Amy cried, laughing. Caidan wasn’t sure if Mathieu was just teasing but, given the footsie and kissing, it really did seem like the bicurious boy wanted to fuck him which, if not for his relationship Casey, he would welcome though fidelity didn’t stop him from imagining would it’d be like with the pretty boy.
On his turn he flirtatiously picked Mathieu as his fantasy free pass.
“Gosh, you two!” Casey laughed. “Mine would be this Hawaiian girl at college named Noelani…”
The continued to chat and drink the wine. Caidan was now unable to ignore the sexual tension with Mathieu who was openly flirting with him, and he teased back, which the girls noticed too and joked about. Soon their supply of wine was running low.
“Let’s go down to the hotel bar.” Amy suggested.
“Sure, but how about we leave the boys here… that way we won’t bore them with our gossip and they can get on with what both of them clearly want to do…”
“Fine by me!” Mathieu laughed, winking at Caidan who blushed but was excited by his girlfriend’s proposition.
Amy laughed. “What a great idea! I think they’re just all talk anyway, but I think you two have your free passes issued!”
“See you later, you owe me one…” Casey whispered in his ear as she followed Amy out of the room.
Amy might have been treating it like a joke, but Caidan could tell that Casey was sincerely offering him the free pass with the brunette boy so, if Mathieu was serious and not just teasing, he was going to grab at the opportunity. Despite their flirting, it was a little awkward to find himself suddenly alone with the boy on the sofa.
“So… what shall we do…” Caidan asked, a little shyly as he didn’t tend to like initiating, it having been Casey who approached him when they met in a queer bar, and the other boy who had begun the footsie, kissing, and picking one another as free passes. He also wanted to make doubly sure that the boy was serious about this, and not just a heterosexual boy who was just fooling around after too much wine, but didn’t mean any of it.
“Hey, I thought you were the gay one who just happened to be dating a girl, I’ve only had a couple of flings with boys before I met Amy and none of them got further than kissing and touching… you guide me!”
“Well, I guess we start by resuming kissing…” Caidan said, knowing what he wanted to do with the boy, and now reassured to take action. He climbed up so he was kneeling on the sofa facing the seated boy, leaning down to kiss his upturned face while caressing his slender shoulders. He felt the boy’s hands on his waist, and liked the feeling of being held by the boy as they made out, their kissing becoming French.
“Let’s get this off…” Caidan said, tugging up the boy’s shirt who raised his arms so it could be pulled up over his head, before they returned to kissing. He ran his hands over the slender bare back of the boy, then brushed his fingers over his exposed chest to gently rub the boy’s nipples which were light brown in colour. The kiss next broke so they could unbutton and pull off Caidan’s white shirt, with Mathieu kissing his flat tummy and chest. He closed his eyes, enjoying the sensation of the boy’s lips wandering over his body, and stroked his fingers through the brunette’s bob cut.
“Yes, tease my nipples babe…” He moaned when he felt the boy’s lips on them, and Mathieu responded by circling his tongue around the areola, and flicking it teasingly over the nipple itself. Caidan tilted the boy’s face up to kiss him again as he eased him back on the sofa so Mathieu was led on his back with him on top. As they kissed slowly and deeply, Mathieu’s fingers wandered over the boy’s chest and then down towards between his legs, feeling his crotch through his trousers.
“I think you’re hard!” Caidan grinned.
“Aren’t you?” Mathieu blushed excitedly.
“Mmm, but that can wait…” Caidan said as he unzipped the front of the boy’s tan trousers, with Mathieu hip thrusting his butt up off the sofa so they could be pulled down his slender legs, lightly tanned and slightly hairy, to reveal his boxer shorts that had a prominent bulge.
“Do you have lube?” Caidan asked, the thought just occurring to him.
“Yes… shall I fetch it?”
“Not right now, but we shall definitely need it later…”
Caidan kissed the boy’s neck, making him moan gently, then worked his way down Mathieu’s chest, stopping to pleasure the nipples with his tongue before continuing down, teasing his belly button, then used his teeth to tug down the boy’s boxer shorts. Mathieu laughed, helping the boy pull down the shorts as though using his teeth was sexy, in a fun goofy way, it wasn’t the most smoothly efficient method.
Caidan examined the boy’s exposed cock, that stood up hard with arousal, and was topped by a neatly trimmed little triangle of pubic hair. He was surprised with how big it was, a little over six inches, as for some reason was expecting the boy would be smaller, however the shaft was prettily slender rather than girthy with a cute little head.
“I’ll suck you but I don’t want you cumming until you’ve fucked me!” Caidan warned before kissing over the slender shaft of the boy’s cock, and teasingly licking it with his tongue. He licked around beneath the penis head, just where it joined the shaft and was sensitive, before taking it in his mouth.
He sucked the tip, tasting a twinge of saltiness from a drop of precum, while stroking the shaft with his hand. Mathieu moaned, running his fingers through Caidan’s pixie cut, unable to prevent himself thrusting a little in his excitement so the boy took his cock deeper in his mouth, moving his hand down to the base so he could take more of the shaft between his lips as he bobbed his head up and down.
A part of him wanted to feel the cock cumming down his throat however knew if he did that, he probably wouldn’t be able to receive a good fucking from it after so constrained his sucking to just foreplay. He kissed over the shaft again, now wet from his saliva, and moved his mouth down to the boy’s testicles, hairless as the boy clearly shaved it, and kissed them, sucking on each ball in turn. He wondered if he was better than Amy at giving blowjobs but thought it was best not to ask the boy to choose between his girlfriend and him.
“I can’t wait to feel your long cock in my butthole… does Amy let you do anal?”
“Occasionally… but you’ll be the first boy asshole I’ve been inside. Shouldn’t we get your jeans and underwear off now too?”
“Good idea.” Caidan grinned, climbing up so he could pull off his skinny jeans and boxers, his cock had gone flaccid during the interlude of giving the blowjob but he knew it’d become quickly erect again as soon as he got some sort of sexual stimulation.
“Do you shave your legs?” Mathieu asked, running his fingers over the boy’s hairless thigh. “I might shave mine too…”
“They’ll look even prettier if you do, but I don’t mind a little hair, and it might make you look too much like a twink for someone with a girlfriend…” Caidan grinned.
“Let’s swap places. I want to see what a cock tastes like before I fuck you.” Mathieu said, and Caidan found it exciting how the boy was now taking the initiative. He led down on the sofa so the boy could stoop down to his cock.
Mathieu tenderly kissed the flaccid penis, and seemed to enjoy licking it, starting his tongue at Caidan’s scrotum, and slowly licking it all the way the underside of his shaft, passing over the frenulum until he reached the tip. He gently fondled the boy’s balls at the same time as taking the cock in his mouth, excited to feel it stiffen between his lips. Though it was the boy’s first time sucking a penis, there was no mistake that he wanted the dick in his mouth, experimenting and eager without a hint of hesitation or doubt.
Caidan’s cock was a little smaller than Mathieu’s, at five inches which the boy eagerly bobbed his head up and down, accidently gagging himself a couple of times as he took it too deeply, but soon settled into a good rhythm to suck it. Caidan took a handful of the boy’s hair, feeling like the chin length bob was the perfect length to give him something to hold onto without getting in the way of the boy’s sucking lips.
Whenever he needed a break, Mathieu paused to do one of his slow tongue licks up the underside of the boy’s cock, which Caidan didn’t mind as they felt good and he found it hot how the brunette seemed to be savouring the taste and texture of his entire cock- scrotum, shaft, frenulum, and head. It was like watching someone enjoy a delicacy for the first time.
“Stop now, or you’ll make me cum too soon!”
“Okay… though just so you don’t get any expectations, I’m not sure I’m ready to be fucked myself today… I’d like to try it sometime but it’s a lot of firsts for a bicurious boy like me… first time a boy’s sucked my cock, first time I’ve sucked a cock, and will be first time I’ve fucked a boy’s ass, so think it’s a bit much at once… though I do want to make you cum some other way!”
“That’s okay… a lot of gays just bottom or top anyway so it isn’t typical to always switch roles. I can always ask Casey to peg me later if in the mood!” Caidan said, caressing the boy’s cheek to show he really didn’t mind. “But I think its time you fetched that lube…”
“Sure!” Mathieu said eagerly, and got up to go to the bedroom, rummaging through his travel bag until he found the bottle of lube, as Amy liked to use it for vaginal sex. Caidan positioned himself on his back, pulling up his legs and holding his thighs so his butthole was exposed.
“I like this position the best as I get to look up at who is fucking me…” Caidan explained, as the boy knelt in front of him on the sofa.
“Fine by me… so do I just squirt this on your asshole as well as my cock?” Mathieu asked as he slipped on a condom.
Caidan nodded, and the boy squeezed a blob of lube onto his palm, rubbing his hands together to warm it then stroked his cock, lubing that first before wiping his fingers over the wrinkled tight speck of the noirette’s butthole.
“Finger me a little first babe…”
“Sure!” Mathieu grinned, and gently rubbed one of his fingers around the butthole, before gently pushing it against the entrance until it slid inside, tenderly pushing it back and forth as the warm hole clenched around his finger.
“It already feels very tight… is my cock really going to fit?”
“Of course, it just needs a little warming up. Ease another finger in…” Caidan said, moaning softly from the one already inside of him. Mathieu obediently pushed another finger against the opening, slowly easing Caidan’s asshole to stretch wider to accommodate both fingers, which tenderly fucked it together.
“That feels great… but I want your cock inside of me.”
“Coming right up!” Mathieu grinned, and removed his fingers, replacing them with the tip of his cock which he gently pushed against the tight opening. The head of his penis slowly penetrated the boy’s butthole, and soon Mathieu was gently thrusting, moaning as he experienced how good the anus felt around his cock. Caidan put his raised feet on the boy’s shoulders for support, so he was able to let go of his thighs rather than clinging to keep them pulled up, and used his free right hand to stroke his own cock as he was fucked by the boy.
Though it was Mathieu’s first time in a boy’s butthole, he had had vaginal sex with Amy in similar positions so wasn’t a novice when it came to thrusting, and picked up a speed and rhythm he kept to, making Caidan’s moans of pleasure almost as in beat as the thrusts of his cock.
“Oh fuck, I want you deeper in me!” Caidan moaned, wanting to take advantage of the boy’s long slender dick, and got Mathieu to help push up his thighs further, and spread them, so now his knees were up against his chest and his feet were either side of the brunette’s butt. This allowed Mathieu to shuffle closer in, meaning his cock slid further inside of Caidan’s asshole with each thrust which increased in intensity, causing the sound of the brunette’s balls slapping the noirette’s buttocks to fill the room.
Mathieu, feeling his orgasm approach, was moaning as well as Caidan, and his thrusts slowed down but became slower and more forceful, pushing deep inside of the boy each time. He cried out as he orgasmed, leaning forward with his cock still inside of the butthole so he could kiss the pale boy beneath him.
“That was amazing, and I really loved looking down at your face as I fucked you…” He murmured before he pulled out of Caidan, who was also very happy with the fucking he had received. Mathieu carefully removed the condom from his softening dick, and tied the end so cum wouldn’t leak out of it and make a mess. Caidan wished the cum could of made a mess inside of his butthole but understood, as they had only met that evening, why Mathieu had worn protection.
“How am I going to make you cum, shall I give you another blowjob?”
“Mmm, maybe you could use your mouth to make me hard again… but think I’ll use your cute butt, not butthole, but your actual buttocks to cum.”
Mathieu went down to kiss the boy’s cock, definitely confirmed bisexual rather than just bicurious as he jumped at the opportunity to taste it again, and raised an eyebrow questioningly.
“You know how a girl might give a boob job by rubbing your cock between her tits, well it’ll be like that but using your butt cheeks!”
“Ah I see… sounds kinky. But first…” Mathieu said before sucking the penis between his lips, blowing it until it became erect again.
Mathieu led down on his front, so his small but juicy butt was accessible for the noirette. Caidan knelt behind the brunette, between his legs, and so he could slide his cock between the lightly tanned buttocks which he trickled lube over so the cleft became a slippery ravine for his cock to rub against.
“That tickles a little!” Mathieu laughed at the feeling of the pale boy’s cock sliding up and down his ass crack. Caidan caressed the boy’s buttocks, and pushed them together so his cock was sandwiched between them as he thrust it back and forth. It wasn’t actually something he had done before but it felt fun, and unlike anal which usually meant the ass cheeks needed to be spread apart, it gave him full view of the firm juicy buttocks pushed together. ‘I’ll have to remember to suggest trying it with Casey…’ Caidan thought, thinking it’ll be something a little silly but hot to vary their lovemaking.
With the sucking, stroking, and buttfucking, he wasn’t far off an orgasm so it didn’t take long for the rubbing against the boy’s ass crack to make him cum. His cock ejaculated a strand of white cum, landing over the boy’s lower back, and followed by a couple of other smaller loads.
“Wow, now I guess I can say I made someone cum just with my ass cheeks!” Mathieu laughed, looking over his shoulder. Caidan grinned, and led down besides the boy so they could kiss again.
“I bet we must have had more fun than our girlfriends chatting in the hotel bar.”
“That is for sure!” Mathieu agreed.
****
Caidan had gotten dressed, while Mathieu took a quick shower before dressing in a fresh pair of boxers to wear to bed, covering his body with a hotel dressing gown. He had just came out the bathroom when the two girls, obviously having had a few cocktails in the bar as they were more tipsy than when they left, returned.
“Just chilling on the coach are we… so you two didn’t take advantage of your free passes in the end.” Amy smirked but Casey pointed excitedly at the used condom on the coffee table which they had forgotten to clear up.
“Who fucked who!” The girl asked.
“I topped, and he bottomed… but we both sucked and I gave him an ass job so think we both got good use out of our free passes!” Mathieu laughed, at the surprised expression of Amy and grin of approval from Casey.
“Oh my gosh, I can’t believe it! Next time perhaps we could stay and watch!” Amy grinned, seeming excited by the thought of watching her fem boyfriend having sex with another pretty boy.
“Anytime they want… as I think it’ll be good for my gay boyfriend to get a taste of cock every now and again.” Casey laughed. “But I think it’s only fair I get a free pass to taste some pussy occasionally too!”
“Agreed.” Caidan grinned. “Though I don’t want you to use your strap-on with some girl… that isn’t for sharing!”
“I feel so boring that I’m the only one who doesn’t need to have a free pass to fuck someone my own gender…” Amy giggled.
“You should give it a go! I’m sure we can find you some girl to experiment with…” Mathieu said.
“Yeah… but not me, I like my girls less girly and more tomboyish! Though my roommate Mitena is an escort so she might be an option…” Casey teased her blonde friend.
“Are you saying I’d need to pay to get another girl to sleep with me!” Amy said in mock outrage.
Caidan relaxed back on the sofa, happy though feeling his relationship just got a little more complicated to explain to people. Now he wasn’t just a gay androgynous boy dating a lesbian girl he found attractive due to her looking gamine enough to pass as a femboy, but one who also got free passes to have sex with real femboys while allowing his girlfriend to sleep with tomboys. He guessed there wasn’t a special LGBT flag for that…
Author’s note: Thanks for reading! I had fun writing gay smut for a change, and it was nice to bring back Caidan and Casey. I have some more ideas for these characters if people want more of them!