"Hey, Charlie," Reese said when his girlfriend answered the phone and greeted him. "I have to tell you something and I need you to promise you won't be mad,"
"Uh-oh, what is it?" she replied with a small hint of concern in her voice.
"I'm not gonna be able to take you out tonight."
"Why? What happened?"
"It's Sky. He called me and said he needed to come over. He just broke up with his girl and...well, he sounded pretty messed up."
"Oh no! That sucks."
"Yeah, I'm sorry. I'll have to make it up to you."
"No, I meant for Skylar. He really liked Cat and they've been together for like, forever. I feel so bad for him."
"Yeah, me too," Reese said with a sigh. "Look, I gotta take care of Sky tonight so we'll have to go out another time."
"Of course. I get it. I'm your girlfriend but he's your best friend. Just know that you owe me two nights of sex now."
Reese had a lighthearted chuckle. "Mhm, and you should know I always pay my debts."
"I'll hold you to it," Charlie said flirtatiously.
"I'm sure you will."
"Mhm. Love you. Take care of your boyfriend. Bye."
"I will. Love you too, babe."
Reese ended the call and sighed. The 'boyfriend' comment was a long-running inside joke that had exhausted its humor sometime within its first month. Charlie still thought it was cute to say so she never stopped referring to Skylar as Reese's boyfriend (or sometimes his 'other girlfriend'), using it really in an endearing way rather than injuriously. Reese hadn't bothered to object to the terms in years, taking it as a compliment on their close friendship. He was a pretty secure guy.
His mind going back to Skylar's situation, he called his heartbroken best friend and conversed with him as he raced to Reese's house. Skylar, his voice quavering from lamentation, told him what happened and expressed his feelings. His now ex-girlfriend, Catherine, had been cheating on him for months (at least), and when Skylar found out, he was hurt but had eventually forgiven her.
She never stopped having sex with the other guy though, and had no intention to. Eventually, Skylar tried to work it out by (reluctantly) suggesting an open relationship, defying Reese's advice, and swallowing what little pride he still had with Catherine. Even though Catherine had accepted Skylar's proposal, she forbade him from dating other girls. Skylar, being so in love with her, stayed faithful while she openly had sex with the other guy, not even trying to hide it for the sake of common decency. Finally, Cat broke it off suddenly and without giving a reason.
Reese listened to his friend vent his heart until he arrived. Opening the door, Reese saw Skylar's crystalline blue eyes sparkling with tears, his full, rose-colored lips quivering. Skylar fell into his best friend's broad chest as soon as the door opened and Reese received him and held him tightly in his large, strong arms.
"It's gonna be okay, bro. That bitch didn't deserve you at all. You were way too good for her, man. Way too good. Do you know how many girls would love to have a guy like you? All of 'em." Reese tried to console Skylar as he closed the door and walked him to the couch with his arm around his relatively small and slightly less muscular shoulders.
"It's too bad," said Skylar, "I only want Ca- Cat- Catherine." At the mention of her name, his eyes flooded once again.
"Stop it, Sky! Stop crying over her. She doesn't deserve it. You could have another one like that." Reese snapped his finger loudly. "One who's not a damn sociopath."
Reese talked Skylar up, holding his hand and wiping his tears away with his thumbs, trying to get him to stop crying. Reese declared the words 'Cat', 'Cathy', and 'Catherine' to be curse words in his house, punishable by a thump to the lip. Skylar laughed for the first time that night when he used her name and Reese meted the punishment, flicking his plump lower lip hard enough for it to hurt pretty good.
Once the waterworks ended, Reese tried to find a way to cheer his bestie up, to get him out of his overall funk. He had forgotten to cancel the reservations for his dinner date with Charlie so decided to take Skylar out instead. Charlie texted Reese to check on Skylar right before they left and he let her know they were going out.
How's our BF? Charlie texted.
Not spectacular, Reese replied.
Aww... 😔 poor baby. Tell him I'll give him a blowjob if he wants, Charlie texted. And as Reese pondered the efficacy of oral sex as a remedy to heartbreak, she texted, ...JK.
Reese laughed to himself and sent, You'd cheat on me to help my best friend!!? 😍 You're so sweet. Definite keeper.
Charlie responded in kind. You'd stan your girlfriend up to help your boyfriend!?🥰 Mary me! Lol
Reese chuckled at Charlie's antics as he and Skylar got in the car. Well, we're headed out. Decided to keep the dinner reservation. Looks like Sky stole your date...
Reese's phone buzzed once more before he took off. It read: Okay. You guys have fun on your date. Wine him and dine him and make him feel better. Have a good time. But not too good a time. If Sky steals my night of sex there will be blood.
Reese chuckled and looked over to Sky, who was eavesdropping on his text conversation and smiling a cute little smirk at the corner of his pouty lips. Reese was happy to see his friend smile, and almost as happy to see that he understood Charlie's and his inside joke, even enjoying it enough to keep the pretty little smile on his face for the entire ride to the restaurant. Reese wondered what exactly was going through Skylar's mind.
At the five-star restaurant, Skylar didn't eat much of his meal but he did, however, drink all seven cocktails he ordered - even the ones he said tasted bad. He always got hyper-emotional and touchy-feely when he drank and tonight was no exception. Reese was happy to have a back corner booth in the dimly lit restaurant, or else he'd be just a tad embarrassed that his best friend kept touching his arm, shoulder, chest, and thigh as he talked. Reese wondered whether he was embarrassed for Sky to be seen in public so obviously drunk, or because he found he didn't hate having Skylar's hands all over him.
As the night progressed, Skylar's babble eased over from Catherine (the mention of whose name earned Sky a slightly more pouty lip), to how good a friend Reese was. Then to how good of a guy Reese was. Then to how good Reese looked. Skylar gushed over his best friend and rescuer's tall and immense tight-end's body, which he kept in excellent shape even after he was finished with football. Reese loved Skylar's thinner, shorter, yet, equally impressive physique, which he also gained while playing on their former high school's football team. It always amazed Reese how Skylar kept up with him during training, even though he was only the kicker.
Reese had felt a little flustered whenever the pretty, older waitress came around and witnessed the intimate bromance, but when they were alone he relished the moment. Who wouldn't love being worshipped until completely flushed by their objectively gorgeous best friend? When the thought came that he might have a crush on Skylar, he gently pushed it aside into the portion of his brain labeled 'preposterous', blaming his slight erection on Belle, their 40-something-year-old pretty server.
After Skylar drank all his drinks he was pretty drunk and needed to "just rest for a bit," leaning against Reese's side. Reese put his arm around his friend to keep him secured and comfy against his chest. Losing the fight with muscle memory several times, Reese would find himself gently caressing Skylar's bare arm, up underneath the sleeve of his Polo shirt and back down to the elbow. After Skylar murmured, "That feels good," in the cutest, lazy kitten voice imaginable, he surrendered to his harmless little habit. Reese was a pretty secure guy.
When the waitress came with the check, she watched with the most voluminous smile as Reese slowly reached for the wallet in his back pocket while trying not to disturb Skylar. Reese blushed when Skylar absently wrapped his arms around his waist. "You two are such a cute couple," Belle gushed in a hushed tone. Reese smiled and thanked her, not bothering with a correction. What could he say, he liked compliments. And he was a pretty secure guy. "Cute, cute, cayoot," the server was mumbling to herself and shaking her head as she walked away, her system apparently overloaded on cuteness.
Reese helped his best friend into the car, buckled him in, and drove him home. Skylar wasn't completely passed out, but Reese figured it would be quicker to simply carry the smaller boy up to bed than to be used like a crutch. Reese scooped him right out of the car and cradled him in his strong arms. Skylar put his arms around the stronger man's muscular shoulders, was carried to his bed, and deposited gently on top of the covers.
Reese removed Skylar's shoes for him, then his socks, then stood back and looked at the picture - the boy in his bed fully clothed in a tight baby blue Polo top and dark denim skinny jeans. He looked absolutely helpless and atrociously cute - so much so that Reese had to convince himself of a pure motive for doing what he was definitely about to do for one reason or the other.
He looks uncomfortable. Surely he's hot and sweaty. It's not like I want to see him undressed! Reese assured himself as he started on the three little buttons on Skylar's Polo, then lifted it over his cobblestone abs, and his head, baring all his hard little chest. I mean, I'm secure enough to admit he's gorgeous without his clothes on, but that's not why I'm doing this. He needs me right now. His fingers became inexplicably clumsy as he unbuttoned his friend's jeans, revealing a small, triangular portion of his tight, pastel purple undies.
Reese, as gently as he could, worked Skylar out of his pants, getting them down a little in the front, trying his best not to touch the tent in the soft cotton briefs his erection created. He carefully turned his friend onto his tummy to pull the jeans down in the back. He slowly did so, revealing the powdery purple boy panties stretched taut over Sky's bubble butt. Reese's heart was in his throat, heat assaulted his cheeks, and his cock strained against his pants, his contextual memory bringing him back to when he first lost his virginity. Stupid brain, he thought, blaming his body's response on faulty programming. Thinks since I'm undressing someone I never undressed before that it's the same kind of thing.
Reese couldn't keep his eyes off his friend's pretty little booty though. Or rather, his light briefs, just then remembering an important fact about Sky's sleeping preferences. Sky usually sleeps naked. I should probably take his undies off for him so that he's comfortable. This night is supposed to be all about him. I shouldn't deny him any comfort because I feel weird about it.
And so, with an excellent reason to do so, Reese hooked his fingers in the waistband of Skylar's purple undies and began to slowly peel them off his perfect little bottom, lifting his hips to get them down past his muscular thighs and off his feet. It was the cutest boy butt Reese had ever seen - a little muscular, but plump like a girl's and completely hairless, even in between.
As a result of another round lost to muscle memory and situational conditioning (so Reese told himself), he took a quick little whiff of the crotch of his friend's undies, a habit he had developed with Charlie. What he smelled there was the unmistakable aroma of fresh precum, his friend's liquid arousal. Probably from thinking about Catherine. I ought to pop his cute little lip again.
He tossed the boy panties aside, feeling significantly more flustered and flushed than he did at the restaurant. His cock was fully engorged and starting to hurt in his pants and he was supremely, superfluously horny. It must be the smell of Sky's precum, he argued internally, my brain thinks it's mine so it's reacting like I'm horny.
Reese stared at the cute boy he had just undressed, and he couldn't help but ogle - hell, marvel - at his friend's naked body. The tight cords of hard-packed muscle beneath taut, smooth skin. Butter soft and petite, but still hard and strong. The muscles in his back and shoulders, his arms and legs, and his glorious, girly tush! It looked so good, especially since Skylar had spread his legs some, separating his cheeks enough to show his posterior valley and a hint of the tight, pinkish little hole, not to mention his soft little cock and balls down below. All clean and devoid of hair.
Reese looked away after gawping silently for half a minute, then shook himself back into his right mind, this time telling himself the alcohol he had drank (one old fashioned) was the culprit. He knew he needed to get out of there and decided to go have a shower and sleep on the couch. So he squeezed Skylar on the shoulder and said, "Good night Sky," before turning to leave.
When he took his first step towards the door, Skylar whined. "No, wait. I don't wanna be alone." He sounded only a little more coherent than someone who needed their friend to undress them. Reese paused beside the bed, looking down at Sky. "I... I want you to... to sleep with me. Please... can you sleep with me, Reesie?"
Skylar was an adorable ball of sadness, cuteness, and neediness, the sexy, dangerous kind. When Reese hesitated, Sky turned onto his back and reached out for Reese's belt buckle. "C'mon. Take off your clothes and get in bed with me." Skylar was still slurring his words and handling the other boy's belt rather poorly. Reese could only marvel - at the incidentally sexy words pouring out of his friend's pretty mouth, at his friend's spectacular body, everything compact and hard, especially his cock, not small but not huge, uncircumcised, with just a little bit of his glistening pink tip showing from inside the foreskin.
"I need you, Reesie," he said sadly. "Please. If I'm all alone, I'm just gonna think about Catherine."
After a brief hesitation, Reese smiled and lifted his t-shirt up and off his body, baring his massive chest. He then tucked Skylar in and hit the lights before dropping his pants and climbing into bed behind Skylar, wearing nothing but his tight white briefs. He was sure to keep about a foot of space between himself and Skylar as he got comfortable.
"Reesie....," Skylar pouted, "I said 'Catherine'. You have to punish me."
"So now I owe you two lashes," Reese said as he leaned over his bestie and applied two softer flicks to his lips.
"Mmm, thank you," Skylar cooed softly, snuggling back into Reese and surprising him. But he didn't balk, but rather, put his arm around his hurting friend, placing his open palm on his tummy. His flesh was like warm silk stretched over smooth stones.
Skylar purred like a little kitten at the touch, and pressed himself back against his immovable friend, snuggling deep into his embrace. "This feels so good, Reesie," said Skylar, and placed his hand on top of Reese's, caressing it gently. "I love you."
"I love you too, Sky," Reese whispered to his friend who he knew was an extremely emotional and affectionate person, especially after drinks. And if Skylar wanted to snuggle, who was he to deny his friend the much-needed intimacy after such an awful day? Reese resolved he would withhold no adoration from his Skylar, admitting to himself that the contact was hypnotically cozy and heartwarmingly sweet.
In that deeply intimate moment, he didn't think it unseemly to give Skylar a kiss, just a little one. And so he did, right on Sky's naked shoulder, eliciting a comfy little moan from him that encouraged Reese to plant another on his solid trapezius muscle, and then his neck, and then his ear.
Skylar's cute little reactions were priceless and Reese loved the effect he was having on him. He was like a toy - kiss here to make me squirm and giggle, kiss here to make me arch and moan. After Reese had sprinkled his bestie's neck, shoulder, and ear in a baker's dozen of candied kisses, he began to drift off to sleep, cuddling his closest friend with the strongest hard-on he'd ever had.
*****
Reese woke up a little groggy and a little dazed, clinging to the familiar feeling of a body pressed against him, sure to be Charlie. His morning wood was sticking up between her soft ass, which was surprisingly and thankfully naked. With his eyes still closed, Reese began to caress a hip. Though it was the right size, more or less, something was off about the feel, but he focused more on how good it felt, rather than how unfamiliar.
Reese started to move his hips back and forth, sliding his cotton-covered wood between the warm valley of flesh. He grabbed a hand full of ass and squeezed. It felt different but more importantly, really good. Overtaken by lust in his hazy mental state, Reese pushed down his boy panties and tried to slide himself into the warm, wet pinkness he knew awaited him between his girlfriend's legs. What he found (or rather, what he didn't find) confused him. Skin. Just skin. No pussy..., and, therefore, not Charlie. In sudden realization, Reese quickly removed his cockhead from Skylar's perineum, rolled away, and fell out of his bed.
He stood and pulled his undies up, then stared at Skylar, who was, thankfully, still sound asleep. A little embarrassed but smirking at his own foolishness, Reese went into his en suite bathroom to shower and refresh his mind. When he finished showering, he came back into the bedroom, his vast fortress of a body dripping wet and completely nude. Reese smiled at the naked boy sleeping peacefully in his bed but stopped staring once his cock began to react. He quickly dried himself and donned a fresh pair of undies, orange and blue striped briefs.
Reese tiptoed around the house, performing a few little chores. He cleaned up a bit and did some laundry, then Charlie called.
"Hey, babe," she answered.
"Good morning," he said. "I miss you."
"Awww, I missed you too. Especially last night. I don't think I know how to sleep alone anymore." Just hearing Charlie's voice expressing she missed him started to turn Reese on. It had been a few months now since the couple hadn't slept in each other's bed. They practically lived together. "I had to put on your t-shirt to fall asleep."
Reese smiled. "Oh, you missed me that much, huh?" he chuckled.
"I did," she admitted. "You didn't find it weird to sleep by yourself after all this time?" she asked, not sounding accusatory, but just curious.
"Well..., uh..., I didn't exactly sleep alone," Reese said, allowing space for understanding.
Charlie laughed, "Oh, my God, you didn't!"
"We didn't, like, sleep together, sleep together. We just... slept... together. Just... in the same bed, is all. He was drunk and all sad and needy like." Charlie was laughing the whole time Reese tried to explain.
"So what did you do, strip him and tuck him in, and spoon in behind him," she said, completely sarcastically and coincidentally one-hundred-percent accurate. The long pause from Reese gave it away.
"Umm...," he managed.
"Oh, my God!" Charlie burst out into a loud giggle. "He really is your boyfriend!" She chortled.
"It wasn't like that, okay. He was hurt, Charlie. He just needed some...," he sighed at what he had to say to justify himself, "...love and affection. I'm the only one who could give it to him. You know how Sky is. He's really emotional and sometimes he just needs a hug and a cuddle."
Charlie had stopped laughing. "So, when I said, 'did you strip him', the answer is 'yes'?" Reese answered by not answering. "I see. So you were naked, cuddling with your boyfriend?" Her voice wasn't humorous and teasing like before, but it wasn't angry either. More like..., curiosity..., mixed with intrigue..., mixed with..., no, it can't be...
"No, only he was naked," Reese replied, hoping it didn't sound so bad. "I was in underwear."
"How did..., how did it feel to have Sky's naked body on yours. Did it turn you on?" Yes, her voice is definitely a little sultry right now. Is she fantasizing about us?
"No- well, not-" he started when she cut him off.
"Mmm it did, didn't it? You caress his hard body? Turn him on? Take advantage of him in his fragile state? Mmm?" She was practically moaning.
"No, it wasn't like that at all. We didn't do anything!" Reese asserted.
Charlie continued. "But you wanted to." That one wasn't a question. "You wanted to touch him. To stroke his cock. It was hard for you to resist, wasn't it?" Her breaths were coming faster as she spoke, even as her voice grew low and misty.
"No. No. No. Charlie, you know we're not like that!"
"Why not?" There was a barely perceptible pout in her voice. "He is your boyfriend after all. I wouldn't mind if you two...made each other feel good. Y'know?"
"What... What are you saying, Charlie?" Reese needed to cut through the layers of sarcasm and find out what Charlie meant.
She sighed. "I'm saying... Oh, God, I can't believe I'm seriously about to tell you this... I'm saying..., I think it would be super hot if you and Sky got it on... There, I said it."
Reese was shocked. He had just gotten an endorsement from his girlfriend to fuck his boyfriend. No! Best friend. Not boyfriend. "Charlie, you know Sky's not gay right?" he said seriously.
"Then seduce him. He got naked in your bed and you two cuddled. All he'll need is a little push from you, Reese, and I bet he'll let you do whatever you want with him." She sounded more like a conspirator than his girlfriend.
"But I'm not gay!" he said with confidence provided only by how badly he wanted her to believe him, rather than the truth. He didn't think of himself as gay, gay, but he could appreciate the sexiness of the masculine form, Skylar's in particular. Maybe he was a little bit closer to bi on the spectrum. Just a little.
Charlie sighed a sigh of very apparent disappointment. "If you say so," she said in a tiny voice before adding, "might be just what Sky needs too."
The idea hung in the atmosphere like an airborne virus. "Well, babe, I gotta go. I'll talk to you later, okay? I love you."
"Okay. I love you too, Reese."
He ended the call and continued to contemplate Charlie's sentiments as he made breakfast for Skylar.
He couldn't get the fact that his girlfriend wanted him to fuck his best friend out of his mind. Nor the idea that it might be good for him. Reese would do anything for the sexy boy upstairs, but he wouldn't take advantage of him in his fragile state - not that I want to. He'd be sweet to him, cuddle him, feed him, and give him everything he wanted, but seduction was completely out of the question.
Reese finished making Sky's big breakfast, set it on a tray, accenting it with one of a dozen white roses he had bought for Charlie the day before, and headed upstairs. He balanced the tray with one large hand as he used the other to snatch the covers off Skylar's naked body to wake him. Skylar roused with a squirming stretch and cat-like yawn, rolling onto his back to glare at Reese, standing there in his underwear with a tray of food. "I made you breakfast," Reese said, placing the feet of the bed tray beside Skylar's thighs and obscuring his rapidly swelling penis from view.
Skylar was grateful his penis was out of his best friend's sight but felt it continue to grow due to the cool air and Reese's tightly muscled frame, not to mention the substantial bulge in his boy panties. Skylar was impressed with the size (in a proud best friend sort of way if you were to ask him). It looks really full even when completely flaccid, he thought just before averting his eyes away from Reese's pack and to the food he'd cooked for him.
"Thanks, Reesie. I was dying of hunger." He started in on the scrambled eggs, crispy bacon, sausage, homemade waffles, fresh-cut pineapples, grapes, and orange juice. Reese watched him as he ravaged the plate, smiling at his friend's ravenous appetite. "You already eat?" Sky asked.
"I wasn't really hungry," he said, sitting down next to Skylar on the bed. "How are you feeling?"
"Great, thanks to you. You know how to make me feel just wonderful." He smiled that great big, gorgeous smile that Reese loved.
"Glad to hear it," Reese smiled back. "So, you're not at all thinking about..., that girl? Y'know, she who shall remain nameless?"
"Who, Catherine?" Skylar said, looking at Reese with a coy smirk, expecting 'punishment.' It made Skylar a little sad to say her name, and therefore to think of her, but there was something about his friend touching his lips that excited him. Something about being treated like a bad child made him feel so guiltily excited. He couldn't explain it.