HER BIG BOY (BOX SET)

 

The Boss’s Assistant

 

Grace looked at Dillon as he reached up turning the showerhead. Her new stepson’s bareback rippled with more muscles than she ever imagined. She had watched him grow from age fourteen, and now at 18 he was a strapping man.

Grace had started working for Dillon’s father right after his wife died, and as the secretary to a widowed executive, a number of family related duties fell to her. Initially it was her who remembered Dillon’s fourteenth birthday, and since his father was out of town on a business trip at the time, it was Grace who delivered his present.

When she first saw her soon to be stepson, she was taken back. He had a narrow tanned face with dark blue eyes and sun-lightened brown hair. He was slightly taller than other boys his age, but more striking than that was his old soul. Grace found that Dillon didn’t say much, but when he did speak his heart seemed so full of warmth and depth that she couldn’t stop staring at him.

“This is from your dad,” Grace said handing him an exquisitely wrapped gift.

Dillon looked back at Grace seeing right through her attempt to make his father look good. Dillon knew who his dad was at this point, and now 14-years-old, he no longer felt the need to pretend. “I thank you for your gift, Miss Evans,” he replied.

Grace considered fighting for his dad’s reputation but knew that Dillon was far smarter than that. “You’re welcome. But he did pay for it, so you should thank him for that.”

Dillon smiled at the beautiful brown-eyed, dark-haired woman in front of him. Staring, he decided that she looked a little younger than his mom did, but she was just as fit. His mom had spent many hours at the gym to look like she did, so he presumed that the long-legged woman with her cleavage showing was equally as committed.

 Continuing to stare at her, she reminded Dillon of his mom in two other ways: She was equally as beautiful; and like his mom, this lean, narrow featured beauty didn’t lie to him.

“So do you like working for my dad?” he asked curiously.

Grace looked at the beautiful boy in front of her wondering how much of her real self she should reveal. “He’s a good boss. He’s demanding, but most executives are. I’m glad to be working for him.”

“Good,” Dillon replied saying much more with the silence that followed.

“So are you going to open your gift?”

Dillon turned his attention to the extravagantly wrapped box. Tearing off the paper he fanned the games in his hand. “Oh wow! These are exactly what I wanted,” Dillon offered with reserved enthusiasm. “I have been asking my dad for these. I didn’t think I was gonna get them.”

Dillon looked up at Grace. “These have made my night.”

Grace’s heart melted upon hearing Dillon’s announcement. She couldn’t tell if it was practiced gratitude or sincere appreciation but his words made her tingle a little. The idea that she could make this lonely boy’s night special satisfied something in her that she didn’t even know existed. She could feel herself glow from it.

“Is someone staying with you tonight?” Grace asked looking around at the seemingly empty house.

“Yeah, Mrs Fernando. She’s our housekeeper.”

“Where is she?”

“She’s watching TV in her room. Did you want something to eat? I can get her.”

Grace looked at the boy wanting to experience more of him and hence knowing that it was time for her to leave. “No, I just wanted to make sure that you weren’t here by yourself.”

“No.”

“Did you two do something special for your birthday?” Grace asked worrying about what he would say.

“No. She doesn’t know,” Dillon said losing the fight to hide his feelings.

Grace’s heart broke staring at the gentle young man in front of her. “I’m sorry.”

Grace’s apology only withered Dillon more.

“You know what? I’ve been known to play a mean game of ‘Gears of War.’ I bet you that I can take you two out of three times in any one of your new games. It can’t be any that you have practice in. We have to start on a level playing field.”

Dillon’s eyes lit up. “You play video games?”

“Of course I do. Do you see which games I chose? What, you think I asked the sales clerk which ones to buy?”

Dillon looked down at the games again. He knew he was holding all of the best. “OK, two out of three,” he said running to the huge flat screen TV in the living room.

Grace followed Dillon watching his exuberance. It made her smile. She liked Dillon. He would have been exactly the kind of boy that she would have fallen for when she was 14, except she was sure that Dillon would have been to mature to like her back.

Dillon set up the first game and both played. Two out of three games turned into three out of five after Grace won. And after switching games didn’t bring Dillon a victory, he demanded a rematch.

“Another time,” Grace pronounced knowing that it was past midnight.

Dillon got silent for a moment. “You’re very pretty,” he said bringing a surprising blush to Grace’s face. “Do you think the next time my dad goes out of town, you could come by and we could play again?”

Grace was hesitant to agree feeling the slight tingling again. But he was so cute and so sweet that she couldn’t resist. “Well, if it’s OK with your dad I will.”

Dillon smiled the biggest smile of the night in reply. “I know it will be,” Dillon responded before becoming much more serious. “This has been the best day I’ve had since…” Dillon’s eyes filled with tears but he refused to let them fall. 

He didn’t have to finish the sentence though. Grace knew what the end of that sentence was. It was his best day since his mother died. Dillon didn’t have to say anymore that night. Grace knew she was hooked. After Grace concluded the night with a hug, that beautiful boy was the only thing that she could think about for the rest of the night. And when her boss finally traveled again, she was immediately back.

It was Grace’s devotion to Dillon that captured his dad’s attention. The secretary and boss didn’t have a very passionate relationship, but the executive did know that she would make a good mother, so their relationship endured.

When Grace began sleeping over she noticed how Dillon would subtly compete with his dad for her attention. In truth, she found it very flattering. And when she became the one that babysat him when his father traveled, she was surprised to learn how supportive he could be as well.

“Is my dad the type of guy you imagined yourself with,” the 15-year-old Dillon asked.

“Can you keep this between us?” Grace said leaning into Dillon on the couch.

“Yeah,” Dillon said with a blush.

“Not really,” Grace added with a smile. “I always imagined myself with a blue collar guy.”

“What do you mean?”

“Like, a guy that’s good with his hands. You know, a man’s man. Don’t get me wrong, your father is an amazing man. Any woman would be glad to be with him. But you asked me if he is the type of guy I imagined myself with, and he isn’t.”

“So you like guys that work on their car and stuff?” Dillon asked taking mental note.

“Or a guy that can fix a car or fix things around the house.  I don’t know. I just think there’s something irresistible about that.”  

Dillon smiled at Grace pleased.

Grace next did something she had noticed herself doing more often, she quickly scanned Dillon’s body. Since they had first met Dillon’s chest had filled out and all of his lean lines were becoming rounded.

For brief seconds at a time Grace would also wonder if his male part was growing at the same rate as the rest of him. She got that answer one day when after knocking on his door to wake him up for school, she walked in to find Dillon had begun to sleep in the nude.

Grace was stunned when she saw his naked tanned 16-year-old body uncovered. It was slightly rounded with muscles poking out everywhere. His feet looked just like a man’s and his hard boy cock was at least six and a half inches and thick. She immediately felt her body flush.

Tearing her eyes away from Dillon’s boy cock, Grace looked up at his face. His eyes were open and staring back at her.

“It’s time to get up for school,” Grace said before slipping out of the room.

Grace rushed toward her bedroom not knowing how to respond. Closing the door behind her she crawled under the covers. Grace felt her pussy swell thinking about her beautiful boy’s naked body and she wanted desperately to touch herself. She couldn’t do it though. She knew he was too young to think about in that way.

Still, his smooth young body and man sized cock were sexier than the sculptures she had seen during her trips to Rome. His Adonis-like face and now curly honey-colored hair were more appealing to her than any she could imagine. And the more she thought about him the wetter she got.

Grace struggled with her desires until in a stroke of desperation, she realized she could replace Dillon’s face with his dad’s. Suddenly free to release her lust, she pressed her tapered finger over her swollen clit and rubbed it until she moaned to orgasm.

“Ahhh,” Grace groaned biting onto her pillow to suppress the sound.  As she lay there, in the warm afterglow, she knew she wasn’t fooling herself. She might have replaced Dillon’s face with her boyfriend’s, but it was the boy who had so boldly stared at her naked that she truly wanted. And since he could very soon become her son, she knew she was now going to have to keep more of a distance from him.

Neither one mentioned what had happened when they next saw each other during breakfast. But whereas Grace had a more difficult time looking Dillon in the eyes after that, Dillon’s demeanor was unchanged. Within a few weeks Grace gained comfort from Dillon’s unaffected behavior and she returned to normal as well. But certainly Grace only knocked on his bedroom door from that point forward.

When Grace married Dillon’s dad, she wasn’t sure how Dillon would react. She was expecting for him to at least express some sort of regret that his fantasy could now no longer be fulfilled. But with his usual unexplainable level of maturity, the 17-year-old boy shook his dad’s hand and then gave Grace a hug.

“I guess I should call you Mom now?” Dillon said with a chuckle.

“I guess you should,” Grace replied with a laugh.

“Well Mommy, welcome to the family,” he said smiling.

“Thank you, son,” Grace retorted still chuckling at the idea.

Grace, now married to his dad, tried to see Dillon as a mother would. Taking a long look up her new tall, muscular, strikingly good looking son, she was amazed that he was the 14-year-old that she had played video games with. 

“You have really turned into quite a man,” Grace admitted.

“Well, I’m glad you think so, because you helped me to become the person I am,” he said with his full faced smile.

Grace kept staring at her new son. During the years that she had known him, she was always amazed how he knew exactly the right thing to say. No matter how she felt, Dillon would always say something that made her feel more special than anyone else ever had. And when staring at Dillon in his tuxedo made her heart rate quicken, she knew it was time to walk away from beautiful boy.

Turning to hug another wedding guest, she peered back at Dillon again. Watching his almost ripened body saunter away, she knew it was time to withdraw even further from him. She loved listening and talking to him, but she was married to his dad now and a clear line had to be drawn. However, staring at her gorgeous new son as he talked to the other guests, Grace knew that it would be one of the hardest things she would ever have to do.

 

Grace watched Dillon’s manly 18-year-old body as he reached up to the showerhead. His raised arms flattened his belly causing his jeans to drop revealing the top of his firm ass. Looking into the crack Grace, could see that he didn’t wear underwear.

Dillon lowered the wide showerhead staring down into the part that screwed into the pipe.

“That’s what I thought,” Dillon concluded. “Do you see this?”

Dillon took the showerhead over to Grace who stood at the bathroom doorway in a silk robe that showed all of the clean lines of the naked body underneath. Grace looked down into the showerhead noticing only that Dillon’s naked chest was so incredibly close to her lightly covered breasts.

“Do you see that little mesh screen in there?” Dillon asked turning the showerhead to the light.

“Yeah, I see it.”

“Well, over time that screen can get clogged by little particles that get in the water supply. So what it does is decrease your shower’s water pressure. But if you clean that out, the pressure comes back.”

“Really?” Grace asked with genuine amazement. “How do you know this?”

Dillon smiled. “Well, my pressure had really dropped off in the last few years and I took it apart to see what was going on. I figured that if mime was clogged, yours would be too.”

“I can’t tell you how grateful I would be if this works,” Grace said with a smile.

“I think you’ll be very happy,” Dillon added with a confidence.

Grace watched silently as Dillon popped out the little screen, cleaned it, and then replaced it. She then returned her gaze at his built man’s body as Dillon put the showerhead back.

“OK, that should be tight. Do you want to give it a try?” Dillon asked turning to Grace.

Grace joined her son at the shower. Sliding her body next to his she reached in front of him for the knobs. She knew that when she leaned over her much taller son, he would be able to look down her robe and see her breasts. The idea thrilled her.

Turning the shower on, a rain of water poured out of the head. “Oh my god, that is so much better. I can’t believe you fixed that.” Grace, still leaning under Dillon, stuck her hand under the droplets. “That’s incredible. Have you ever showered under one of these rain showerheads before?”

“No.”

“Oh, you have to. You should take a shower in here one of these times. It’s an incredible experience.”

Grace stood up and looked into her boy’s eyes just in time to see them dart back up to her face. He had been looking at her breasts, she decided. The thought made her nipples protrude through her silk robe.

“I can’t believe how much of a man you’ve become. I remember when you were just a kid,” Grace reminisced while being filled with his masculine musk. “Where is that little boy I used to know?”  Grace said feeling warm all over.

“I don’t know,” he replied. “I guess you helped him grow up.”

Both stared at each other a moment longer before Dillon walked out. Following him into the bedroom Grace watched his firm ass as he left.

“Dillon?”

He turned around approaching the door.

“We don’t talk anymore. Why is that?” Grace asked not ready to let him leave.

“I don’t know,” he said with regret. “But I miss it.”

Grace felt her heart melt for her beautiful boy.

“So what’s been going on in your life?” Grace asked leaning on the bathroom door not knowing how much she glowed in the backlight.

Dillon looked back at his mom and felt a pain in his heart. To him, she was the most beautiful woman that he had ever seen, and their brief interactions were all he could stand at a time without him losing all of his practiced control.

“School, I guess. I’m starting to apply to colleges.”

“What about socially? You never bring anyone by the house. Is there a special someone?”

Dillon debated settling in to the conversation by sitting on the bed, but he couldn’t presume. He wanted Grace, but he felt that if he made a move and it was rejected, he could lose her forever.

He still regretted when he laid naked waiting for her to come into his bedroom. Grace was clearly uncomfortable about it for weeks after, and her brief withdrawal felt like one of her stiletto heels through his heart. He never wanted to lose her like that again, so keeping that in mind he stayed planted where he was.

“I have a couple of buddies that I hang with,” Dillon replied avoiding the second half of the question.

“No special girl… or guy?”

Dillon smiled. “No. There’s no special guy. And I know that there would be nothing wrong with it if there was.”

“There would be nothing wrong with it,” she replied a little relieved. “Girl then?”

“There might be a girl,” he said blushing.

Grace felt her heart drop with disappointment at the news, but didn’t allow herself to show it. “Oh really! Why is this the first time I’m hearing about this? Tell me about her,” Grace requested feeling herself sweat with anguish.

“It’s someone that I’ve known since I was a kid.”

“Ok, that’s good.”

“And she’s really beautiful. She’s the most beautiful person I’ve ever met.”

Grace fought back the tears as she listened to Dillon describe the woman that had his affections instead of her. “Uh huh.”

“And she’s one of those types that you can just count on. She sacrifices so much for others and doesn’t even realize how much everyone appreciates her for it. And did I mention how beautiful she is?” he repeated with a glassy-eyed smile.

“No, you mentioned that,” Grace replied feeling what felt like her heart ripping from her chest. “Then why haven’t you asked her out?”

“Because she’s in a serious relationship.”

“You’re 18. There’s no such thing as a serious relationship at that age.”

“I wish it were that simple,” he said lowering his head.

“Don’t over think it.”

Dillon looked down at the soft cream carpet under his feet trying to find the courage to look back up. “What would you want me to do if it were you?” he asked feeling his tanned face becoming red.

“If it were me?” Grace repeated trying to fight back her excitement about the idea. Thinking about it a while longer, she spoke. “Well, if it were me, I would want you to tell me. Women are very good at hiding their feelings. You can never tell how happy a woman is in their relationship, and you sharing your heart might be exactly what she needs for her to realize that she is with the wrong man.”

Dillon felt himself sweat at the prospect. “So how would you want to be told?”

“Well, not all girls like this, but I like big gestures. I like guys who aren’t scared to show me how they feel.”

“Even if it was dangerous to admit it?”

“Especially if it’s dangerous,” Grace added with a blush. “Girls like a little danger.”

Dillon stared at his mommy not knowing what else to say. Grace stared back just as quiet. Looking at each other for a while, Grace was the first to speak.

“I’m going to take a shower now.”

“OK,” Dillon replied hesitant to leave.

When he finally walked out Grace watched him go. He had turned into the sexiest man that she had ever seen and thinking about him made her heart ache.

Without closing her bedroom door behind him, she took off her robe and laid it onto the bed. Standing naked with her nipples erect and her swollen lips pushing through her trimmed pubes, she looked up at her open door hoping that he might turn and come back in. He didn’t.

Entering and leaving the bathroom door open, Grace turned on the shower. She couldn’t wait to feel the increased droplets on her back. She imagined they would feel like Dillon’s fingers touching her all over her body and she couldn’t imagine a better feeling.

Stepping behind the frosted door, Grace entered the rain. It was warm and comforting. She felt her body come alive as the heat hit her swollen bean and the tips of her fingers followed.

Grace closed her eyes and rubbed her clit. “Ahhh!” she moaned quietly. This time the only thing she could think of was Dillon and the thought made her need to lean against the wall.

Grace flipped her head back feeling the water pelt her face. It was glorious. With her fingers vigorously rubbing her clit and her big boy locked in her mind, there was nothing else she could ask for – until the shower door opened.

Letting go of her crotch Grace was snapped back to reality. The reality she found was even better than her fantasy. Standing in the wide shower door was a naked Dillon whose chest heaved with excitement.

Grace’s mouth hung open with shock at what she saw. Not only had her fantasy come to life, but Dillon’s undressed body was a breathtaking sight. Dillon’s thick muscular chest was amazing enough on its own, but his 16-year-old boy cock now seemed gone. What replaced it was a hard, shaving-can thick, eight inch cock that dwarfed anything that she had ever seen. Dillon really was a big boy now, and his big boy was rigidly standing at attention. Grace looked back up into Dillon’s face which was flush with vulnerability.

Dillon’s large pecs bounced under his breath as he tried to figure out if he should stay or leave. And not giving him a clue as to what he should do, she stared in his eyes and screamed at him in her mind. “Take me. Just ravish me!” she thought.

Dillon stared back at the woman he had always loved frozen as to what he should do. She had said that she would want a big gesture. Now standing in front of her with is cock fully hard, he didn’t know what else was left. “Take her,” he heard a voice yell in his mind. “Don’t ask, just take her.”

Dillon dipped his head about to turn around when instead he threw himself forward toward his love. With one step he found himself under the droplets with Grace in his hand. Looking down at the woman who yielded to his strong touch, he took aim and kissed.

Dillon pressed his strong firm lips against Grace’s taking the back of her head in his free hand. Twisting her, he opened his mouth and there waiting was his love’s delicate tongue. Twirling and tugging on each other’s tongues the couple found themselves lost in the other. Each of his strokes led to her bends and her protuberances lead to his succumbings. They were perfectly in sync.

Dillon let go of Grace’s arm, and touched her stomach. Although still locked in their kiss, his focus was entirely on his finger tips now. For years he had dreamed what it would be like to touch her. His childhood fantasy world had been based on which hand he would use. And with his right hand gently resting on the side of his princess, his adult cock twitched with excitement.

Having touched her naked body for the first time his mind suddenly awoke to a new world of pleasure.  Breathing through the pain of his throbbing heart, he pushed his hand up her soft skin until his strong fingers cradled her soft abundant breast. His cock dripped with lust.

Grace broke away from the kiss taking a deep breath. Dillon’s manly hand on her breast overwhelmed her. His presence and touch released years of pent up desires that she could never admit to but also couldn’t resist. Dillon was the man of her dreams. He was kind, considerate, and breathtakingly gorgeous. And if all of those qualities weren’t enough, he also had the most magnificent cock she could ever imagine.

Grace threw her arms around her big boy feeling the curves of his young defined back. There was not a flaw on it. Following the channel down its center, her hands then hit the river between his deep ass. Having looked at it too many times to count, having imagined it masked by the faces of so many other men, Grace grabbed it. Her chest heaved with delight.

With her mind swimming, Grace took grip of Dillon’s ass and pulled it to her. What she felt as their bodies collided was the fulfillment of all of her dreams. And with Grace’s swollen pussy dripping, Dillon’s giant boy cock pressed against her stomach.

“Huuh,” Grace gasped taking a sharp breath in.

Dillon’s hand gently caressed her breast and his tongue returned to her mouth. Grace closed her eyes and took all of it in. But what she really yearned for, what her loins throbbed in ecstasy for, was to feel Dillon’s manly boy cock fill her hole.