Steven sat there in his neon boxer shorts as his sister tried to remain patient with him. "Steven, why don't you wear tighty whities?" Rachel asked, teasing him as she rummaged through their shared laundry basket. She held up a pair of boxers, the fabric a riot of bright colours, faded with age, the cotton fabric beginning to fray. “These boxer shorts are no worse than what you are wearing right now which have holes in them.
Steven rolled his eyes, not bothering to look up from his book. "They're just not comfortable, Rach. That's all. Why can I not wear normal briefs instead of tighty whities."
Rachel tossed the boxers back into the basket with a laugh. "You're such a weirdo," she said, shaking her head. "It's like you're rebelling against society's underwear norms or something and to be honest, David’s comment about your boxer shorts being ugly is right, they are ugly and full of holes and fraying material. Frankly, you should be ashamed to wear underwear like that. The problem you face in normal briefs is hiding your dick. If you must have such a large one, which you do, and it’s also the biggest cock I have ever seen, you must manage your modesty better and briefs just don’t cut the mustard. They are too skimpy, that’s why. Tighty whities will suit you much better."
Steven sighed and marked his page. "It's not a rebellion. It's about personal comfort. Why do you even care what I wear under my trousers anyway?"
Rachel smirked. "I'm just saying, with your, uh, size," she gestured vaguely in his direction, "normal briefs might be a bit... restrictive making it essential to keep realigning yourself which is not recommended when out in public and boxer shorts are uncomfortable because they bunch up your thighs which means you need to sort them out from time to time."
Steven felt his cheeks redden. Rachel had always had a knack for hitting a nerve. But he knew she was right. Ever since hitting puberty, he'd felt like a bull in a china shop in traditional briefs, preferring his boxer shorts. They never fit quite right, leaving him feeling constricted and awkward. Boxers, on the other hand, offered the freedom and comfort that his burgeoning physique craved. Plus, they had the bonus of hiding his embarrassment from the world.
“Okay, okay," he relented, closing his book with a thud. "If it'll get you off my back, I'll give them another shot." Rachel's eyes lit up with excitement, and he knew he'd just signed himself up for an afternoon of shopping torture. "But I'm not promising anything."
The next day, Rachel dragged him to the mall. They wandered into a department store, the fluorescent lights flickering overhead. Rachel grabbed a basket and started tossing pairs of Hanes, Jockey, and Fruit of the Loom underwear into it. She had a wicked glint in her eye as she tossed a pair of tighty whities with cartoon characters on them. "For old times' sake," she said with a smirk.
Steven couldn't help but feel a little nervous as they approached the fitting rooms. Rachel had always been the outgoing one, unafraid to voice her opinions. But this was his personal space, and she was treading on sacred ground. He took a deep breath and stepped into the small cubicle, the basket of underwear feeling like a judgmental jury in the corner.
"All right," Rachel called out, her voice muffled through the door, "start with the Hanes. They're classic."
Steven sighed, picking up the white pair from the basket. He slipped off his boxers and slid on the Hanes, the fabric feeling strange and foreign against his skin. He glanced at himself in the mirror, the elastic digging into his waist and the legs feeling like a vice around his thighs. Rachel's voice echoed through the door, "How are they?"
He turned to the side, inspecting his profile. The fit was snug, but bearable. The briefs did seem to keep everything in place more than his usual boxers. "They're... okay, I guess," he murmured, his voice sounding a bit too high for his liking. Rachel's giggle from outside made him blush even more.
"Come on, let's see!" Rachel said, her voice a mix of excitement and impatience.
Steven took a deep breath, turned the lock, and stepped out of the fitting room. Rachel's eyes went wide at the sight of him in Hanes tighty whities. The white fabric contrasted starkly with his tanned skin, and she had to admit, they did look surprisingly good on him. The elastic band hugged his waist, and the briefs themselves outlined his muscular legs and... other assets.
"Well?" Rachel asked, her voice a little too eager.
Steven looked down at himself, feeling the fabric cling to his body. "They're... different."
Rachel nodded her expression a mix of amusement and satisfaction. "They are. But let's not get ahead of ourselves. Try the Fruit of the Loom now. They're supposed to be more supportive."
Steven sighed and retreated into the fitting room. He pulled the tighty whities off and reached into the basket for the next pair. The FOTL brand of tighty whities felt smoother in his hands, the material seemingly less likely to ride up and cause chafe. He stepped into the pristine white briefs, the waistband hugging him snugly as he pulled them up. They felt surprisingly good, the fabric stretching comfortably across his hips and thighs.
"How are these?" Rachel called out, her curiosity getting the better of her.
"They're... better," Steven said, his voice a bit more hopeful. The FOTL were indeed more supportive. He could feel the difference as he moved around in the confined space. They hugged his body in a way that was both snug and surprisingly comfortable. He stepped out of the fitting room again, the pristine white of the briefs standing out against his skin.
Rachel's eyes scanned him up and down. "They're a good fit," she said, nodding with a smirk. "But I think we can do better. How about trying the FOTL mesh design?"
Steven raised an eyebrow, unsure of what she meant. "What's so special about mesh?"
"They're supposed to be breathable," Rachel explained, holding up the pack of underwear. "Perfect for when it's hot out, which, let's face it, is most of the time in this town. Trust me, you'll thank me when you're not sweating bullets in those boxers of yours."
Steven took the pack from her, eyeing the white mesh fabric warily. He slipped into the fitting room and put on the new pair. The material felt cool against his skin, a stark contrast to the thick cotton of his usual boxers. He couldn't deny that Rachel had a point; these might be more comfortable in the heat.
"All right, let's see the final verdict," Rachel said, tapping her foot outside the door.
Steven took a deep breath and stepped out, feeling the coolness of the mesh design against his skin. The white fabric was see-through in some spots, but the mesh provided enough coverage to avoid embarrassment. He turned to Rachel, who nodded approvingly.
"They're different," he said, feeling the material shift with his movements. Rachel leaned in closer, inspecting the fit.
"Perfect," she said with a nod. "You look like you could run a marathon in those. And the white will keep you cool."
Steven couldn't argue with her logic, even though the idea of switching to tighty whities full-time was still a little unsettling. "All right, I'll give them a shot," he said, resigning himself to Rachel's challenge.
"Great!" Rachel clapped her hands together. "We're buying 14 pairs of the FOTL mesh briefs. That'll replace your entire underwear drawer."
Steven felt a twinge of panic. "What? No way, Rach. That's overkill."
"Oh, come on," Rachel said with a wink, pushing the basket into his arms. "It's just a little bet. And think of the payoff. You'll be so comfortable; you'll never want to go back to those oversized boxer shorts and skimpy briefs again."
Steven sighed, knowing Rachel wasn't going to take no for an answer. "Fine," he said, "but I'm not wearing them around the house."
Rachel just grinned. "Yes, you are, and you'll get used to it," she said, as they headed for the checkout. "And think of it this way: Mum and Evie are going to see you in your underwear anyway so you might as well get used to it now."
Steven couldn't believe what he was hearing. "But Rach, it's not just about comfort. What if they see me in these?"
"So what?" Rachel said with a shrug. "They're family, they've seen you in your underwear before. And it's not like you're parading around in them. Just be you, Stevie. Besides, you can't hide forever."
Steven's stomach churned at the thought. Rachel was right, but the idea of his mother and his other sister, Evie, seeing him in tighty whities was a whole new level of mortification. Rachel was always so comfortable in her skin, but he had never quite mastered that level of self-assurance.
He took a deep breath and nodded, pushing the cart through the store with Rachel by his side. She was like a proud coach, guiding him through the uncharted waters of tighty whities. They picked out fourteen pairs of the Fruit of the Looms, filling the basket until it was overflowing with white underwear.
"Remember what I said, Stevie," Rachel whispered as they approached the checkout, her eyes gleaming with mischief. "When you get home, lose the shorts and wear just a white t-shirt and your new tighty whites."
Steven felt his cheeks flame up at the thought. "Rachel, I'm not walking around the house in his underwear!"
"You're wearing tighty whities, not your birthday suit," Rachel quipped, her eyes sparkling. "Besides, it'll be like your own personal underwear fashion show. Think of it as practice."
Steven couldn't help but feel a mix of dread and excitement as they left the mall. Rachel had a way of making him do things that were outside of his comfort zone, but he had to admit, the idea of walking around in just his new briefs was... liberating.
And that's how he got into tighty whities.
The moment he walked through the door, Rachel grabbed his hand and tugged him upstairs to their shared bathroom. "Come on," she said, her eyes shining with excitement. "You can't chicken out now."
With a deep breath, he slipped out of his shorts to reveal his new white FOTL mesh tighty whities Rachel had convinced him to buy. The fabric was indeed cooler than his usual boxers, and he had to admit, the support was surprisingly comfortable. Rachel handed him a plain white t-shirt from his drawer, and he pulled it over his head. "Ready?" she asked, her voice betraying a hint of glee.
They descended the stairs, and the moment his bare legs hit the living room floor, he felt a wave of self-consciousness wash over him. His mother, engrossed in a TV show, didn't even look up. Evie, his younger sister, glanced over from her laptop, her eyes flicking down to the waistband peeking out under his t-shirt, before returning to her screen with a smirk. Rach, the instigator, sat on the couch with her arms folded across her chest, watching him with an expectant look.
The house was hot, the air thick with the scent of dinner simmering in the kitchen. The white fabric of the tighty whities clung to him, the mesh providing a welcome breeze against his skin. Despite his initial apprehension, the comfort was undeniable. Steven took a tentative step into the room, the coolness of the floor tiles sending a shiver up his spine.
His mother; woke up from her show, her gaze lingering for a moment before she turned back to the TV, a knowing smile playing on her lips. "You've made a good choice, love," she called over her shoulder. "Your dad and I always knew you'd come around eventually."
Evie looked at her brother and grinned, "Nice package Steve, I always knew you were big but that crazy," returning to her laptop for something more woke.
"I told you it would be okay," Rach piped up as Steven retreated into the kitchen.
"How am I going to deal with David, sis? He hasn't seen me in this type of underwear and he's going to laugh that I'm so big," as Steven turned bright red with embarrassment and fear. "I also don't know what to do if he finds me truly attractive."
Rachel just rolled her eyes. "You're so dramatic," she said, her tone light and teasing. "But if it makes you feel any better, David's been crushing on you for ages. Who knows, maybe this is your chance to make a move."
"Really?"
Steven's heart skipped a beat at Rachel's revelation. "Trust me," she said with a knowing smile. "But remember, this is your show, Stevie. You set the pace and frankly, with that dick, most men would die for one that size."
The thought of David seeing him in the tighty whities and possibly being attracted to him made Steven's head spin. Rachel noticed his discomfort and patted his shoulder reassuringly. "Look, it's not a big deal. Just be casual about it, like it's normal. You'll be fine, I promise."
"But I don't know what to do, sis."
Rachel winked at him, "Just be yourself, Stevie. And maybe stop worrying so much about what other people think of your underwear choices. Besides, I suspect he only cares about what's underneath."
"But sis, I don't even know how to, you know...suck."
Rachel's eyes widened before she burst out laughing. "Oh, Stevie. You're so clueless," she said, wiping a tear from her eye. "You just have to be gentle, okay? It's not rocket science and if you want to swallow, do so, otherwise, for fucks sake, allow him to shoot at you. It's quite simple and just go with the flow."
"Sis..., can I ask you something else?"
"Sure, what's up?" Rachel said, popping a grape into her mouth and watching him fidget.
Steven took a deep breath. "I'm... I'm still a virgin, Rach."
Her laughter abruptly stopped, and she stared at him, her mouth full of grapes. "What?" she finally managed to get out, chewing and swallowing quickly. "How is that possible?"
Steven felt his face redden even more. "I just never found the right time, or the right person, I guess," he mumbled, fidgeting with his t-shirt.
Rachel's expression softened, and she put a hand on his shoulder. "Don't worry, Stevie," she said, her voice gentle. "It's not a race. But if David's interested, you might as well go for it."
The thought of taking that step with David was both terrifying and exhilarating. Rachel's confidence in him was surprising, and he found himself looking at her with newfound respect. "You think I should?" he asked, his voice barely a whisper.
"Why not?" Rachel shrugged. "You're both adults and if you're both into it, what's the harm? Why don't you phone David and arrange to meet?"
"Perhaps I will sis," looking at his phone sitting on the table. "I will do it later, promise, after dinner."
Rach knew he wouldn't do it as she watched Steven Walk into the kitchen. "That boy she muttered to herself; he will never get laid if he continues like this. Fuck it..." as she grabbed Steven's phone to unlock it.
Rachel sat there texting her brother’s budding boyfriend. "Hi David, do you fancy coming over tomorrow? It will be nice to spend some time with you if you're available?"
David replied saying "Love too, see you at seven, XXX."
Rach noted the text kisses and was happy she had done the evil deed and smiled with delight returning the phone to the table just as Steven returned from the kitchen.
The next evening, Steven was sitting in the garden on the patio wearing only a t-shirt and his tighty whities when the doorbell rang, assuming it was for his sister he didn’t bother to answer it. He remained glued to the chair, dreaming of David and wondering how he should manage his desires towards him when Rachel bounced out of the house with a grin plastered across her face, David following close behind. "Surprise," Rachel said, pushing him towards Steven. "I invited David over for dinner."
Steven's heart raced as he looked up. "Sis, I'm not dressed, oh, hi David, I wasn't expecting you, sorry, I'm not dressed, let me go and put some shorts on."
David's eyes widened when he saw the tighty whities peeking out from under the hem of Steven's t-shirt. "You did say come over this evening Steve in your text yesterday."
"I did?" realising that Rachel had had a part in staging this impromptu gathering. "Yeh, sorry, I forgot," looking at his sister with dagger eyes that only siblings can do. He then realised she had planned everything including him being scantily dressed on the patio as he saw she had even gone so far as to set up a little picnic area, complete with blankets and cushions.
"Hey, you look good," David said, his voice a little hoarse as he took in the sight of Steven.
"Oh, um, thanks David," Steven managed to croak out, his face feeling hot. Rachel winked at him before disappearing back into the house, leaving the two of them alone as David took a chair and sat down joining Steven.
David cleared his throat, his gaze lingering on the white waistband of Steven's tighty whities. "So," he said, "how do you like them?"
Steven felt his cheeks burn. "Like what? Oh, the underwear. They're... fine," he said, trying to sound nonchalant. "They're different and yeh, I sort of like them."
David leaned in closer, his eyes locked on Steven's. "They look good on you," he murmured, his voice low and intimate. "Good,” as he eyed Steven's groin and the impressive bulge that was noticeable even to a blind person.
Steven's breath hitched, and he could feel his cock twitch in response. Rachel's words played in his mind, telling him to just go with the flow. He swallowed hard, looking at David, who was staring back with a mix of desire and curiosity. "Thank you," he said, his voice barely above a whisper.
The moment stretched out between them, the only sounds were the distant laughter from the TV and the rustle of the leaves in the breeze. Then, without warning, David leaned over and kissed him. The touch was gentle and tentative, and it sent a bolt of lightning through Steven's body. He gasped, his hands flying to David's shoulders, and then he was kissing back, his body coming alive in a way it never had before.
Rach though, ever the loving sister was watching from the kitchen window, smiling with pride as her plan appeared to be working as she wondered if dinner might now be off the cards.
They broke apart, both panting. David's eyes searched his, looking for any sign of rejection. But all Steven could feel was the overwhelming need to be closer to him, to explore this newfound attraction. Rachel had set the stage, and now it was up to him to play out the scene. He took a deep breath, his heart pounding in his chest. "Do you want to go upstairs?" he asked, his voice shaky.
David shook his head, his eyes dark with desire. "It's nice out here, and it's nice and warm," he said, "Besides, there are blankets and cushions we can use, and your sisters are in the house, and it might be distracting with all the noise."
Steven nodded, his mind racing with excitement and fear. Rachel had set him up, but she had no idea how far this would go. He took a deep breath and leaned back into the kiss, feeling the heat from David's body pressing against him. They fumbled with their t-shirts, desperate to feel the warmth of skin on their skin.
David gently lifted Steven's t-shirt up and over his head and then he did the same, gently lowering himself to kiss Steven's nipples. They broke apart long enough for David to kick his shoes off leaving them both with their socks. David's eyes trailed down to the tighty whities again, and he reached out, his fingertips brushing the waistband. "You do look good in these," he murmured, his voice thick with lust.
Steven's stomach flipped as David's hand moved lower, his fingers slipping beneath the elastic to stroke his lower stomach. He could feel his cock straining against the fabric, desperate for release. Rachel's words of encouragement echoed in his mind, and he decided to take the plunge. He leaned back, pulling David with him, the two of them collapsing onto the blanket on the grass.
Their kisses grew more heated, their bodies grinding together as they explored each other's skin. David's hand slid down further, cupping the bulge in Steven's tighty whities. He gave a gentle squeeze, and Steven moaned, his hips jerking upward. "Is this what you want because it’s what I have been wanting for ages?" David asked, his voice low and gruff with passion.
Steven nodded, unable to form words as he felt the fabric of his new underwear stretch around David's hand. "Y-yeah," he managed to stutter. "But Rachel's inside..."
David smirked, leaning to whisper in his ear, "So are your mum and Evie, but that doesn't mean we can't have a little fun, does it?" His hand squeezed a little harder, and Steven felt his resolve melt away. Rachel had set this up, but he was the one who had to live with the consequences. And right now, all he could think about was the way David's hand felt on him.
With trembling hands, David reached down and pulled at the waistband of Steven’s tighty whities, sliding them down his legs. The cool evening air hit his skin, making him shiver, but David's warm hands quickly followed, pushing the underwear away from his hardening cock. David's eyes were wide with amazement as he took in the full view of his friend's size. Rachel had been right; David was interested, and she hadn’t exaggerated when she told him quietly and in confidence that his prospective boyfriend was big. As he gazed upon Steven, he rather thought that Rachel had underestimated his endowment. He would call it huge.
"Wow," David breathed, his hand hovering over the thick shaft that now pointed straight up. "You're... big."
Steven felt his cheeks burn with a mix of pride and embarrassment. Rachel's words came back to him, urging him to be confident. He took a deep breath, his heart racing as he watched David's hand close around him. The feeling was electric, sending waves of pleasure through his body. David's grip was firm but gentle, and he began to stroke him with a slow, steady rhythm.
Their eyes met, and Steven could see the desire in David's gaze. Rachel had been right about him; he had been crushing on Steve for a long time, and now that they were here, at this moment, the tension between them was electric. "It's okay," David murmured, "I've got you."
Encouraged by Rachel's earlier words, Steven leaned back into the cushions, his legs falling open slightly. David's hand stroked him with a gentle but firm grip, his thumb circling the head of his cock, sending jolts of pleasure through him. He bit his lip to keep from moaning too loudly, his eyes sliding closed as he gave in to the sensation. Rachel had told him to be himself, to set the pace, but right now, he was happy to let David lead.
As David's hand worked its magic, Steven grew bolder. He reached out to touch David in return, his hand tracing the outline of David's cock through his Jeans. The fabric was stretched taut, and Steven could feel the heat and hardness beneath. Rachel had told him to be gentle, and he hoped that his touch conveyed that, as he began to undo the jeans that had become an obstacle.
They sat there, their hands exploring each other, the soft sounds of their breathing the only noise in the quiet evening. Rachel had set the stage, but it was the two of them who were now the stars of their show. Steven could feel his heart racing, his breath coming in shallow gasps as David's strokes grew more insistent. Rachel had been the one to push him into this, but it was David's touch that was making him feel alive in a way he never had before.
And then, Rachel's voice pierced the silence, calling out from the house, "Guys, dinner's ready!" The spell was broken, and both froze, their eyes going wide. Steven's cock throbbed with need, and David's hand paused on him for just a moment before he leaned in and kissed him again, a promise of things to come.
They quickly pulled away, adjusting their clothing as Rachel stepped out onto the patio, a knowing smile playing on her lips. "You two looked like you were having fun," she said, her eyes twinkling. "Come on, let's eat before it gets cold."
Steven felt his face burn as he stood up, his cock still half-hard and his tighty whities doing little to hide his arousal. Rachel's smirk was unmistakable, but she said nothing as they all walked back into the house. Dinner was a blur of forced laughter and awkward glances, the tension palpable between him and David. Rachel had played matchmaker, and she had done it with a flair that only she could manage. But now, the challenge was to navigate these new waters without capsizing the boat.
After dinner, Rachel announced she had plans with friends, giving them the perfect opportunity to be alone together. She winked at Steven as she left, and he knew she was expecting a full report later. The moment the door closed, the silence in the house was deafening. David looked at him, his eyes full of want. "Are you okay with this?" he asked, his voice barely above a whisper.
Steven took a deep breath and nodded. "Yeah," he said, his voice steady. "I'm okay with it," as he led David upstairs to his room, his heart pounding in his chest. He had never done anything like this before, but Rachel's words of encouragement played on a loop in his mind.
Once the door was closed, they wasted no time. They tumbled onto the bed, kissing and touching each other with a desperation that was both thrilling and overwhelming. David's hands were everywhere, exploring every inch of his body, and Steven found himself doing the same, tracing the lines of David's muscles with a mix of awe and desire. Rachel's advice about being gentle echoed in his mind as he reached into David's underwear, feeling the heat and weight of his cock for the first time.
They stripped each other bare, the fabric of their clothes discarded on the floor like the last vestiges of their former selves. Steven's inexperience was evident, but David was patient, guiding him with gentle instructions and encouraging whispers. They kissed and touched and explored until the line between them blurred, and all that was left was the raw, unbridled passion of two men discovering each other's bodies.
He took David in his mouth, tentative at first, but soon growing bolder as he felt the other man's moans of pleasure. Rachel's words about swallowing played in his head, and he knew he had to try. He took David deeper, his throat tightening around the thick shaft. It was a strange sensation, one that was both terrifying and exhilarating. Rachel had been right; it was all about going with the flow.
And as he felt David's grip tighten in his hair, he knew that this was just the beginning. He sucked harder, feeling the warmth spread through him, and knew that he was ready to embrace whatever came next.
David's breath grew ragged, and his hips began to thrust. Steven knew he was close, and the thought of being the one to make him come was thrilling. He swallowed around the thickness, his throat muscles working in a way that seemed to drive David wild.
But it was David's hand on his cock that sent him over the edge. He arched his back, moaning around David's length as his climax built.
"Steve," David panted, his voice strained with pleasure, "you're so good at this."
The words sent a warm glow through Steven, and he redoubled his efforts, eager to make this moment perfect. The desire that was driving him now. He focused on the taste and feel of David, letting instinct guide him. And when David's body stiffened and he felt the hot spurt of cum fill his mouth, Steven swallowed, the salty taste a newfound delight.
They lay there for a moment, both panting, their hearts racing in sync, cuddling on the bed, their bodies still flushed with excitement. "Thank you," David whispered into his ear. "Thank you for letting me show you how much I've wanted this. Now, it's my turn."
He rolled them over, his eyes never leaving Steven's, and then he started to kiss a trail down his neck, across his chest, and down his stomach. David's hands were gentle, his touch reverent as he reached Steven's cock, standing proud and flushed. "Wow," he murmured, his eyes wide with wonder. "You're... massive."
With a gentle touch, David wrapped his hand around the base of Steven's cock, feeling the heat and the pulse of life beneath his fingertips. He leaned in and took the head into his mouth, sucking gently at first, then with more urgency as Steven's hips began to buck.
Steven's eyes rolled back in his head, his breath coming in quick gasps as David worked his magic.
David took his time, savouring the taste and feel of him. He licked and kissed his way down the length of Steven's cock, feeling the veins pulse with every beat of his heart. He took him deeper, his desire for his friend growing with each stroke. Steven's hips bucked involuntarily, pushing his cock further into David's mouth.
Steven's moans grew louder as David's head bobbed up and down, his tongue swirling around the sensitive tip. He reached down, his hand tangling in David's hair as he held him in place, urging him to go faster, deeper, sending a new wave of pleasure through him, and he knew he was close.
The feeling was unbearable, his toes curling into the bed, his body taut with tension. He watched as David's eyes met his, the love and lust in them making him feel alive. He could feel the orgasm building, the tightness in his balls, and he knew he couldn't hold back much longer.
"Fuck, David," he moaned, his voice hoarse with need. "I'm gonna cum."
David's eyes widened, but he didn't stop, his hand squeezing the base of Steven's cock as he took him deeper, eager to taste his release. And then it washed over him, a flood of heat and pleasure that left Steven trembling, his body arching off the bed as he gave in to the feeling, the first orgasm of his life with another man.
They lay there, panting and spent, their bodies entwined. "Thank you," he murmured, his voice barely audible as he kissed David again.
David's eyes searched his, a soft smile playing on his lips as he whispered, "Thank you for letting me." And with that, they drifted off to sleep, their naked limbs wrapped around each other in a tangle of newfound intimacy.
In the weeks that followed, Steven grew more comfortable in his skin. Rachel had pushed him out of his boxer shorts and into tighty whities, and in doing so, had pushed him into a new chapter of his life. He and David grew closer, their relationship evolving from friendship to something more intimate and beautiful. Rachel watched from the sidelines, her mischievous smile never far from her lips as she knew she had played a part in bringing them together.
And when the inevitable happened, and their mother walked in on them kissing in the kitchen, Rachel was the first to laugh. "Well, it's about time," she said, rolling her eyes. "I thought I was going to have to spray paint 'Gay and Proud' on the garage door."
Their mother had taken it in stride, hugging them both tightly. "As long as you're happy, that's all that matters," she said. Rachel had been right about her too; she had known all along and had been waiting for Steven to catch up.
The house was filled with love and laughter as they all sat down for dinner, Rachel's knowing glances and Steven's shy smiles speaking volumes about their newfound relationship. Rachel had orchestrated a change, not just in his underwear but in his life, and for that, he was eternally grateful.
That night with David’s departure home, the house grew quieter as Rachel tiptoed down the hall to Steven's bedroom door. She knocked softly, a mischievous smile playing on her lips. "Stevie," she whispered through the crack, "have you done it yet?"
Steven's cheeks flushed scarlet as he looked up from his laptop. "What?" he asked, his voice a little too high. Rachel chuckled, pushing the door open wider. "You know what I'm talking about," she said, her eyes twinkling. "Don't be shy I know you have sucked him off and I'm pretty sure he has returned the favour, but have you done it yet. Come on, I have a vested interest in this you know."
He took a deep breath, trying to compose himself. "No," he said, his voice barely above a whisper. "We haven't yet."
Rachel's eyes widened; her expression incredulous. "What do you mean you haven't yet?" she exclaimed in a hushed tone. "You've been practically inseparable!"
"Well, we're taking it slow," Steven replied, his voice a mix of embarrassment and excitement. "We want to make sure we're both ready."
Rachel rolled her eyes playfully. "If you two don't get with the programme, I'm going to have to start charging admission to your little underwear fashion shows," she teased.
Steven felt his cheeks burn even hotter at Rachel's words, but he couldn't help but chuckle. "We're just taking it slow," he said again, feeling the need to reassure her. Rachel winked at him, her expression turning serious. "Remember what I told you, Stevie, it's about connecting, not just the act but at some point, the act becomes important, and it seals the relationship at a different level. Anyway, I’ve said what I needed so, good night and see you in the morning."
At that Rachel returned to her bedroom, more frustrated than surprised, muttering her disappointment as she closed the door.
Steven lay there, Rachel's words echoing in his mind. He couldn't deny the excitement that bubbled within him at the thought of taking his relationship with David to the next level. Rachel had been instrumental in pushing him out of his comfort zone, and now he found himself eager to explore further. The anticipation was like a sweet ache, a constant reminder of the uncharted territory that lay ahead.
Rach lay in bed plotting the next turn of her brother's relationship with David. How could she orchestrate it she wondered and then a brain wave hit her. They needed a picnic by the sea, and she would organise it. Feeling happy with herself, she laid back and closed her eyes wondering how far she was happy to go for her baby brother as her eyelids closed and wrapped her in sleep.
The next day, Rachel woke up early with a spring in her step and a mischievous grin on her face. She knew exactly what she had to do to push Steven and David closer together. She had an ace up her sleeve, a plan that was sure to get their engines revving. She began to prepare a picnic basket, filling it with all their favourite snacks and a couple of bottles of wine she had stolen from her mother's stash.
Breakfast was a whirlwind of energy as Rachel told Steven about the picnic, she had planned for later that day. "You're going to invite David, right?" she asked, her eyes glinting with excitement. "Tell him it's just a casual thing, no pressure."
Steven swallowed a mouthful of cereal, his mind racing with the implications of Rachel's plan. "I don't know, Rach," he said, his voice hesitant. "It's kind of... bold."
Rachel rolled her eyes. "Bold is your middle name, remember?" she quipped. "You're going to love it. Trust me."
Steven couldn't argue with that. Rachel had a knack for making things interesting, and he had to admit, he was curious about where she was going with this. He called David, his heart racing as he extended the invitation. David's voice was filled with excitement, and he agreed immediately.
The picnic by the sea was everything Rachel had hoped for. The waves crashed against the shore, the salty air mingling with the scent of the food. The sun kissed their skin, making it warm and inviting. Rachel had even packed a few of Steven's new tighty whities just in case they needed a little extra encouragement.
As they ate and talked, Rachel could feel the tension building between her brother and his crush. She decided it was time to make her move. "You know what would make this picnic even better?" she said, her voice light and playful. "A little skinny-dipping!"
David's eyes widened, and Steven's cheeks turned a deep shade of red. Rachel laughed, standing up and peeling off her clothes without a care in the world. "Come on, guys," she said, her voice taunting. "Don't be shy."
Steven looked at David, and something in the other man's gaze told him that he was game. They both stood up, stripping down to their underwear. Rachel nodded approvingly at the sight of the tighty whities she had picked out. "Well, take them off too if you are planning to skinny dip," as she slipped her knickers off muttering?
Steven and David looked at her naked body and took the plunge, slipping their tighty whities down and off.
Rachel looked at both naked for the first time and in full view and she admired the partial erection that both boys were displaying and then understood for the first time, how huge her brother was when compared with an average man. Impressive she thought as she turned towards the sea, calling their names.
The three of them dashed into the waves, the chilly water a shock to their naked bodies. Rachel squealed, splashing water in their faces. They played in the surf, the laughter echoing across the beach. Rachel watched as David's hand brushed against Steven's thigh, his eyes darkening with desire.
The moment Rachel had been waiting for had arrived. She stepped back, giving them space, watching as their friendship grew into something more. David leaned in, and Steven met him halfway, their lips coming together in a kiss that was both tender and fierce. Rachel felt a pang of something she couldn't quite name, a mix of pride and a hint of jealousy as the boy’s arousal became obvious and for the first time, she was seeing Steven hard, terribly long, big, and beautiful. David wasn't bad she thought but wow, Steven was just magnificent.
But she pushed her thoughts aside, focusing on her role as the mastermind behind this romance. She knew she had done well, setting her brother on the path to happiness. And as they kissed, the waves crashing around them, Rachel couldn't help but feel that she had played a part in creating something beautiful.
Remaining quiet, Rachel continued to watch as the boys became more aroused and excited as they explored each other tongues whilst their hands were employed elsewhere.
"Boys, I'm going for a walk along the water line, I suggest you move to the blanket for some comfort."
The boys either didn't hear or had become deaf to interruptions as they walked towards the blanket hand in hand, both sporting a physical eagerness that left nothing in doubt.
Rach was happy as she skimmed the water’s edge, still naked but one with herself as she sat down not a hundred feet away to watch the boys, she had been instrumental in getting to this point.
David's eyes never left Steven's as they lay down on the soft sand. The tension in the air was mind-blowing, and Rachel felt a thrill of excitement at the sight of the lube that she had left on the blanket was moved by David to a handier position. She knew what was about to happen, and she had to admit, she was a little envious of the intimacy they were about to share.
With trembling hands, David reached out and wrapped his hand around Steven's cock, which was now fully erect and standing tall. Rachel watched, her eyes wide, as David leaned in closer, his breath hot against the sensitive skin. And then, without a word, he took it into his mouth, his lips closing around the tip with a soft pop that made Rachel bite her lip to keep from gasping.
Steven's eyes rolled back in his head, his body arching with the sudden pleasure. She watched as David took more of him, his cheeks hollowing with each suck, his throat working to take all of Steven's length. Rachel felt a warmth spread through her own body, a vicarious thrill at the sight of her brother's pleasure.
David's other hand was busy exploring Steven's body, tracing the lines of his abs and chest before finding his way down to cup his balls, rolling them gently in his hand. Rachel watched, transfixed, as the scene unfolded before her. She had never felt more alive, more connected to her brother's happiness than she did in that moment.
Steven's moans grew louder, and Rachel knew he was close. David's technique was flawless as he took Steven more. Rachel felt a thrill run through her as she watched, her hand slipping between her legs, her fingers playing with her clit, mirroring the movements of David's mouth on Steven's cock.
As the waves kissed the shore, Rachel watched David's hand move to his erection, stroking in time with his mouth on Steven's cock. The sight was almost too much to bear, but Rachel knew she had to keep her cool as she continued to pleasure herself.
The boys didn't seem to notice her presence, lost in their world of passion and exploration as Steven got closer to his orgasm.
Rachel's hand moved faster, her breaths shallow and quick, as she watched David's hand stroke his cock, feeling her desire peak along with her brother's. She could see the muscles in David's arm tensing as he picked up speed, his eyes still locked on Steven's face.
And then it happened. Steven's body tensed, his hips bucking off the blanket as he came with a guttural moan, the sound echoing off the beach. Rachel watched as David's throat convulsed around his brother's shaft, swallowing down every drop of cum like it was the sweetest nectar. It was an erotic sight, one that Rachel had never anticipated she would bear witness to, and it sent her over the edge as well. She bit her lip to stifle her cry of pleasure, her body shuddering with the intensity of her orgasm.
For a moment, there was only the sound of the waves and their ragged breathing. Rachel's hand slowed, her orgasm subsiding, and she took a moment to appreciate the beauty of what she had just seen. The love and trust between the two men were palpable, and she felt a strange mix of pride and arousal.
David pulled back, his lips swollen and shiny with cum, a look of pure bliss on his face as he met Steven's eyes. He leaned in and kissed him softly, a kiss filled with all the love and passion he had been holding back for so long.
Steven's heart was racing as he felt David's body pressing against his, the weight of him grounding him in this new reality. He wrapped his arms around David's shoulders, pulling him closer, feeling the stickiness between them as their kiss grew more intense.
David laid on his back, "Steve, I want you," his gaze was clear, his smile reassuring. "I want this," he whispered, reaching up to caress the side of Steven's face. "Sit on me, my love."
With trembling hands, Steven reached for the lube Rachel had left. He straddled David's hips, feeling the heat of David's cock pressing against his ass. Rachel watched from her vantage point, her breath hitching in her throat as she saw the love and desire in their eyes.
Steven took a deep breath and squeezed a generous amount of lube onto his fingers. He felt a thrill of excitement mixed with nerves as he reached behind him, sliding his slick digits down to prepare himself for David. Steven then squeezed more lube onto his fingers and massaged David's cock with a liberal amount, Rachel’s heart pounded in her chest as she observed the intimate moment, the connection between them growing stronger with each touch.
Steven took a deep, steadying breath, then leaned forward to kiss David, their tongues mingling as he began to lower himself onto David's erect cock. Rachel felt a pang of something unfamiliar as she watched them, her hand moving faster between her legs.
Their kisses grew more urgent as David's cock breached the tight ring of muscle, the sensation of penetration making both men gasp. Rachel's eyes were glued to the sight of David's cock disappearing inside her brother, the look of pure ecstasy on both their faces. It was a moment of raw, unbridled passion that she had never anticipated witnessing, and it sent a shock of arousal through her.
Slowly, with care and patience, Steven lowered himself onto David, inch by glorious inch, until he was fully seated. Rachel watched as David's eyes fluttered closed, a soft groan escaping his lips. The sound was like music to Rachel's ears, and she couldn't help but wonder if she had created a masterpiece of love with her meddling.
The two men held onto each other tightly, their bodies moving in sync with the rhythm of the sea. Rachel's hand continued to work between her legs, her arousal building with every moan and sigh that carried on the breeze. She knew she should look away, and give them privacy, but she was too invested in the moment she had orchestrated.
Steven's hips began to rock, tentatively at first, then with more confidence as he grew accustomed to the feeling of being filled. Rachel watched as David's hand reached around to stroke his cock, the sight of his brother's pleasure driving him to new heights. The sun painted their bodies with a golden glow, highlighting the tension in their muscles and the passion etched into every line of their faces.
The waves crashed against the shore, providing a rhythmic backdrop to their lovemaking. Rachel felt her orgasm build again, her breath catching in her throat as she watched the two men move together in a dance of lust and love. She had never felt more connected to her brother, prouder of who he was becoming.
As their tempo increased, Rachel's hand matched their pace, her desire spiralling out of control. She couldn't tear her eyes away from the sight of David's cock sliding in and out of Steven, his abs tensing with each thrust. It was a beautiful moment, one that Rachel had never dreamed she would see.
Their breaths grew ragged, their bodies slick with sweat and the sea's saltwater. Rachel could feel the tension in the air as David's strokes grew more urgent. She watched as his hand gripped the base of his cock, his other hand digging into the sand, his face a mask of pleasure.
"Fuck, Steve," David groaned, his hips bucking up to meet Steven's, his orgasm approaching like a wave ready to break. Rachel's eyes were glued to the sight of David's cock disappearing into her brother, the muscles in his neck standing out as he held on, fighting for control.
Steven's breath grew ragged, his eyes squeezed shut as he felt David's cock hit that special spot inside him, the one that made his toes curl and his whole body shake with pleasure. Rachel's earlier advice played in his mind, reminding him to breathe and relax, to let the sensations wash over him.
He felt the tension in David's body as he approached his climax, the way his cock grew thicker and the way he moaned into their kisses.
"Steve," David gasped, "I'm close." Rachel watched expectantly as the two men's movements grew more frantic, their passion a living, pulsing entity between them.
"Me too," Steven murmured, his voice hoarse with desire. Rachel felt a thrill run through her as she watched her brother's face contort with pleasure, the way his eyes rolled back, and his teeth sank into his bottom lip.
Their bodies moved together, a symphony of passion played out on the beach, the waves crashing in time with their hips. Rachel watched as David's hand tightened on Steven's cock, stroking him with a precision that spoke of experience and love. The sound of their skin slapping together, the cries of pleasure that mingled with the gulls' calls.
The tension was palpable as David's hips bucked upwards, his orgasm approaching like a storm on the horizon. Rachel could see the veins in his neck bulge, his eyes glazed over with pleasure as he thrust into Steven's tight warmth. "Come for me," he panted, his voice thick with desire. "Come with me, baby."
Steven's eyes flew open at the words, and Rachel saw a flash of something unspoken pass between them. It was a moment of pure, unadulterated intimacy, a connection that went beyond mere friendship. With a strangled cry, Steven's body stiffened, his cock pulsing in David's firm grip. Rachel watched in awe as her brother's orgasm washed over him, his body shaking with the force of it as he shot spurt after spurt of cum onto David's face and chest. More cum shot out, landing on David's stomach leaving Rachel in awe with her brothers’ quantity.
David's cock swelled inside of him, and with one final, powerful thrust, he too reached his peak, his semen filling Steven's ass in hot, wet spurts. Rachel felt a rush of pleasure at the sight, her hand still working furiously between her legs.
As the two men collapsed against each other, their bodies sticky with sweat and cum, especially the sight of David's seed coating Steven's body, the raw intimacy of their union, it all coalesced into an intense climax that Rachel couldn't contain. She bit down hard on her lip to keep from crying out, her hand still working furiously between her legs as she felt the waves of pleasure crash over her. Her eyes were glossed over with lust as she took in the erotic tableau before her, the way David's cock was still half-buried in her brother's ass, the way they both glowed with satisfaction.
Her orgasm had hit her like a tidal wave, stealing her breath and making her muscles quiver. Rachel's body went slack as she finally allowed herself to succumb to the overwhelming desire that had been building within her since she had first set this plan in motion. The seawater rushed around her, cooling her fevered skin as she lay there, panting and trembling, closing her eyes in quiet recovery.
On the blanket, Steven and David were lost in their world, their embrace tight and full of love as they kissed tenderly, their bodies still joined. "I love you, Steve, I do."
"I love you too," Steven whispered back, his eyes full of emotion.
They lay on the blanket cuddling each other for a while, basking in the afterglow of their shared climax. The sea breeze cooled their skin, and the warmth of the sun dried their sweat-slicked bodies. It was a perfect moment, one that felt like it could last forever.
But as the minutes ticked by, Steven's eyes drifted to the spot where Rachel had been watching, and he saw her, lying in the shallow waves, her eyes closed, the gentle motion of the water caressing her body. Rachel looked serene, almost as if she were asleep, the waves lapping at her skin like a lover's tender touch.
The boys got up off the blanket and walked over to where Rachel lay, her eyes still closed, taking in the moment. Steven laid down next to her on the left and David on the right, their naked bodies a testament to the inner peace they were all feeling. Steven turned towards his sister putting his arms across her breasts as David followed suit, his arm coming to rest on her stomach. Steven had never been so close to his sister and had never done anything so intimate, but it just seemed the natural thing to do. David found Steven's fingers and they intertwined the small but meaningful touch of fingers as a symbol of their union they lay there cuddling, devoid of inhibition, the water lapping against their bodies, silent in thought and at peace with the world around.
Rachel was the first to stir, feeling the sun's warmth start to fade and the coolness of the evening settle over her skin. She opened her eyes to see the fiery orange hues painting the sky, the first stars just beginning to peek through the deepening blue. Rachel felt a warmth that wasn't just from the sun, it was a warmth from knowing she had played a part in something so beautiful, so pure. She looked over to see her brother and David, still wrapped around her body, the picture of contentment.
"Guys," she whispered, not wanting to break the spell. "We should probably head back."
They pulled away from each other, the spell of their union momentarily broken. Rachel felt a twinge of sadness as they separated, but she knew they had taken a significant step in their relationship. She watched as they dressed, their movements a little awkward but filled with a newfound affection.
"Thank you, Rach," Steven murmured, his eyes filled with a mix of love and gratitude. Rachel felt a warmth spread through her chest as she took in her brother's words. "You knew what you were doing."
David chuckled, his gaze tender as he looked at Rachel. "Yes, thank you. I've never felt so... seen." Rachel couldn't help but feel a slight twinge of jealousy at the depth of connection between them. She had hoped to bring them together, but she hadn't anticipated the intensity of their bond.
"Sis, I think you also knew what you were doing and thank you for sharing your body and your intimacy. I have never seen you pleasure yourself. It was beautiful to watch.
For the first time, Rachel felt her cheeks grow warm with a blush that spread down her neck and chest. It was a strange feeling; one she hadn't experienced in a long time. She had always been the one in control, the one orchestrating the perfect moment for others, but now she was a participant in a way she hadn't anticipated. The realization that her brother had watched her climax, that he had seen her in such a vulnerable state, was both mortifying and oddly thrilling.
They folded the blanket with a sense of finality, the fabric whispering secrets of their shared intimacy. Rachel gathered the picnic basket, the sand clinging to the outside like a silent witness to their passionate afternoon. The bottles of wine clinked together, a gentle reminder of the liquid courage that had fuelled their daring escapade.
Standing together, they took a collective deep breath, the cool salty air filling their lungs as they stared out at the horizon. The sea stretched on; an endless canvas painted with the deepening hues of twilight. Rachel felt a sense of accomplishment as she took in the sight of Steven and David, their bodies now dressed but the intimacy between them palpable. It was a magical finale to a magical afternoon.
"Fuck, boys, have you seen the time, mum will kill for being so late." The boys looked at Rachel, "what?" she exclaimed, and at that moment, they sent a telepathic message to Mum, "Please forgive us."
They looked out to sea for the final time that day and then they turned and walked away, taking the memories with them as the sea enveloped the beach, ready for a new day.
