Romance: My First Time With The Tycoon Read online

  Chloe watched Maria disappear up the stairs and turned her attention back to the plate of food in front of her. It was barely lukewarm but she was still hungry enough to eat it. Picking up her fork, she began to pick at her plate.

  Chapter 7

  Chloe sat on the floor in the library. The kids had long since taken themselves to bed and Maria and the rest of the house staff were turning in for the night as well. The silence of the house made Chloe realize just how tired she was. She struggled to stay awake a she flipped through the pages of Alice in Wonderland. It was always one of her favorite books, particularly the illustrated edition. As she looked over each illustration, she tried not to let her mind wander back to the state of Linda Hammond. She couldn’t help but wonder however, why Linda was drinking so much. What had happened to take her from dutiful wife and mother to drunken mess? She wished that Dana knew what was happening, just so she had someone to talk to about it. She contemplated asking Doug, he would most certainly know, but she wasn’t sure if it was the type of question you should ask. Obviously in most circumstances it wasn’t, but her new relationship with Doug left many fuzzy boundaries.

  “Hey, sleepy head.” Chloe’s eyes snapped open and she tried stiffly to sit up. She had fallen asleep in the library with her back against the bookshelf. As she slept she must have slid down the shelf and ended up in a slumped heap on the floor.

  “Hmm?” She rubbed the back of her neck as she leaned back against the bookshelf.

  “I thought I might find you in here.” Doug said with a smile. Chloe focused her eyes on him and realized that he was dressed to the nines. A perfectly pressed tuxedo and a red bowtie around his neck were complimented with shining black shoes.

  “Wow,” she said in a croaky voice. “You look nice.” Doug smiled as he crouched down and sat beside her.

  “Kids in bed?” He asked. Chloe nodded.

  “Your wife is too.” She said without thinking.

  “What?” Doug asked.

  “She came down to the kitchen when I was down there with Maria. I’ve never seen Linda drunk but if I’d lit a match she would have gone up in flames.” Chloe said. Doug groaned.

  “Urgh, not again.” He sighed.

  “She came looking for wine but I sent her to lie down and said I’d bring it to her.” Chloe said. “She passed out before Maria went to go check on her.” Doug shook his head.

  “I guess now you know why we’re separating.” Doug said. Chloe nodded silently. “She’s been like this for a while.” Doug said.

  “She never used to be…” Chloe said. Doug shook his head.

  “No, when Dana went away to school Linda started drinking. It’s only become worse since I’ve had to start working more at night.” He sighed loudly and looked up at the ceiling. Chloe leaned over, putting her head on his shoulder.

  “I’m sorry.” She said. She knew it wasn’t enough, but it was all she could think of to say. She felt him nod.

  “Thanks, me too.”

  The sadness in Doug’s voice as he talked about his wife made Chloe feel guilty for what she and Doug had done.

  “Do you think you can fix it?” Chloe asked. “The two of you, I mean?” There was a long pause before Doug spoke.

  “No. That ship sailed a while ago I’m afraid.” He said.

  “You sound so sad. How can it be over if you’re so sad?” Chloe asked, lifting her head to look at him. Doug seemed to think about the question for a while before answering.

  “When you go through so much with someone, like I have been through with Linda, you always love them. It doesn’t matter what happens, you always love them.” Chloe nodded and lay her head back on his shoulder. “But,” he added, “There’s a difference between loving someone and being in love with someone.” He said.

  “Hmm.” Chloe said. Despite being twenty years old she had never ever felt as though she was in love. She had dated plenty of men, but no one had ever struck her as The One, the way that she imagined they should. Judging from what Doug was saying now, she was quite glad that they hadn’t. “It sounds kind of complicated.” Chloe said.

  “It can be.” Doug said.

  Doug and Chloe sat in the library listening to each other breathing for what felt like an eternity before Doug spoke.

  “Come with me.” He said as he got to his feet slowly. Chloe got up to her feet and followed him as he walked through to his office and out in to the main foyer. As he took a step on the staircase, Chloe looked at him and shook her head.

  “I can’t go up there!” She whispered desperately. Doug frowned.

  “Why?” He whispered back.

  “Your wife is up there!” She whispered back. Doug shook his head.

  “Everyone sleeps on the second floor. My room is on the third.” Chloe hesitated before following him up the stairs. When they got to the second floor she stepped extra cautiously, afraid of wakening anyone. Doug led her to a door at the end of the second floor hallway. When he opened it a tall staircase went straight up. Doug gestured for Chloe to go first.

  When she got to the top of the stairs, Chloe saw a large king sized bed in front of a large window. More interestingly however, there was a spiral staircase in the center of the room. Without looking back at Doug, Chloe went straight up the spiral stairs and came out in a small room surrounded by windows.

  “Oh my God, it’s like a lighthouse!” She said, still whispering. When Doug finally made it up to the small room he shook his head.

  “You don’t have to whisper.” He panted. “You’re two whole floors above everyone else. I’m pretty sure you’re safe.” Chloe grinned.

  “I like it up here.” She said.

  “It’s my little oasis.” Doug said. “No one ever comes up here except me. It used to be my office, but since Linda and I separated I made it my bedroom. Chloe peered out of the window that overlooked the back of the house. The view was incredible.

  “I can’t believe this has been here for so long and I never knew about it.” She said.

  “That’s because I never wanted to show it to you until now.” He said with a smile as he wrapped his arm around the small of her back.

  Chapter 8

  Doug pulled Chloe in to him, spinning her around and leaning down he planted a kiss on her mouth. Chloe could barely breathe from the butterflies in her stomach. Even if he and Linda were splitting up, there was still so much that was forbidden about her being with Doug. Yet, the more she thought about how forbidden it was, the more turned on she became. Doug felt her hesitating.

  “What is it?” He asked, pulling back.

  “I…nothing…” Chloe said, standing on her tiptoes and leaning towards him. As her lips met his, he smiled against her mouth.

  “Uh uh, you can’t get away that easily. Tell me what’s wrong…” He lifted his head so that Chloe couldn’t reach his lips.

  “I don’t know.” Chloe sighed. “It’s still kind of weird, but then when I think about the weird stuff and it makes me horny…” Chloe said, her eyes cast down at the floor with embarrassment.

  “Hmmm…so you like forbidden things then hmm?” Reaching forward, Doug lifted her chin with his finger. Chloe lifted her eyes back to his and nodded slowly, a look of uncertainty on her face.

  “Oh I know plenty of forbidden things that will get you really excited.” Doug said with a grin. Chloe couldn’t help but giggle.

  “Stop, I’m serious!” She said. Doug laughed.

  “So am I!” He replied.

  “Okay then, show me” Chloe said. She had a feeling that she was going to regret asking him that later, but for now she was ready and willing to find out what he had to show her.

  “Are you sure?” Doug asked. Chloe nodded emphatically. “Alright…well, you’re going to have to get naked I’m afraid.” Chloe smirked.

  “Are you just trying to get me naked?” She said, squinting her eyes at him. Doug shook his head innocently.

  “Oh no, I wouldn’t do that. I just need you naked to be
able to show you something…” Doug said, the corner of his mouth lifting in a smile.

  “I don’t believe you, but in the spirit of adventure…” Chloe stripped for him.

  Once she was completely naked and feeling more than a little vulnerable, Chloe looked up in to Doug’s wide eyes.

  “What now?” She asked, her nipples already hardening.

  “Now…” Doug loosened his bowtie and proceeded to strip himself naked as well. Chloe watched as his throbbing cock popped loose from his tuxedo pants.

  “You didn’t have any underwear on?” She asked, her eyes fixated on his monster cock. Doug shook his head.

  “But that’s not the forbidden thing I wanted to show you…that’s just a bonus.” He grinned as he stepped out of his pants.

  When completely naked, Doug looked at Chloe.

  “Last chance…” he said. Chloe couldn’t stop staring at his cock.

  “For what?” She said, fixating on the glistening drop of pre-cum on the tip of his cock. Doug reached down and stroked his cock firmly, watching Chloe’s eyes light up.

  “To back out…” Doug said as his fingers reached the tip of his cock. He rubbed the slick drop of pre-cum around his cock head. Chloe licked her lips hungrily. She shook her head.

  “I’m not backing out.” She said.

  “Good…” Doug said, taking a step towards her.

  Gently, Doug spun Chloe around so that she was once again facing one of the four large windows. Taking a step forward he nudged her closer to the window until she was right up against it.

  “Hands on the window.” He commanded. Chloe hesitated. “Hands on the window.” He said again, firmly. Chloe did as she was instructed. Then she felt him pushing her so that her cheek came up flat against the window.

  “Mmm…” Chloe moaned as she felt Doug reach down and part her legs. Then he stepped up behind her, pressing so close to her that she could feel his cock throbbing against her. Beginning to tease her, he slid his cock vertically between her ass cheeks and pressed his body against hers. Her face pushed flat against the glass he listened to her breath coming quickly.

  “Do you want to know now?” He asked.

  “Mmm…” Chloe moaned. Slowly moving his hand downward, Doug slid his cock from between her ass cheeks and in one movement without warning he slid inside her. Pulling out, he slid inside her again. He repeated this a few times until his thick cock was covered in her sticky pussy juice.

  “Are you ready?” He asked. Chloe was breathless from the shock of feeling his huge cock inside her, skin on skin.

  “Uh huh…” She said quietly. Then she felt it. The incredible pressure as Doug pressed against her tight asshole. Taking a deep inhale, Chloe bit down hard on her lip.

  “Ever so slowly…” Doug said as he pressed forward a little at a time. The pain was almost too much for Chloe to bear as he began to stretch her tight hole.

  “Oohh!” She moaned.

  “You can do it.” He instructed her as he continued pushing.

  Chloe wasn’t so sure that she could do it. The sensation was unlike anything she had felt before. A mixture of pain, pleasure and a desperate feeling that she had to use the bathroom. Just as she was sure that she had to give in and beg him to stop, she felt a feeling of incredible relief. Her ass felt full and she could feel Doug’s naked body pressed up against her, his pelvis against her ass.

  “That, my love, is what we call forbidden.” She could hear the smile in his voice as he pushed forward just a little more.

  “It feels…incredible!” She said, her breath fogging up the glass in front of her.

  Doug pulled backwards, his cock sliding out of her tight hole until he was almost completely out of her. Then slowly he thrust forward again. Chloe was sure that she wasn’t going to last much longer.

  “Do you like my cock in your ass?” Doug hummed in her ear. Chloe nodded, her sweaty skin squeaking against the cool glass.

  “Uh huh…it feels so good, so tight!” Chloe said, trying hard not to hyperventilate as she caught her breath.

  “Mmm, you are tight.” He said as he thrust forward, burying his cock deep inside her perfectly plump ass. Sliding his hands around to her front, Doug grasped her perky breasts. With one in each hand he pinched her perky nipples tightly between his thumbs and forefingers. He looked over her shoulder through the window, hoping that someone out there was watching as he pressed her naked body up against the pane of glass. He imagined them watching as he pinched her budded nipples and sunk his cock shaft inside her ass. He pushed forward just a little more, his pelvis coming up flush against her ass cheeks.

  “Ahh!” Chloe cried out. Doug stilled.

  “Did I hurt you?” He asked, gently.

  “Uh uh, it just feels so good!” Chloe said. Doug pulled back and thrust deep inside her again.

  “God, your ass is so tight around my cock, you’re going to make me cum inside you.” As he spoke, Doug continued to thrust in to her puckered asshole. “Do you want me to cum inside you, Chloe?” He asked hungrily.

  “Yes, oh God yes!” Chloe begged now as she pushed against him, managing to push out her ass just a little. The further she stuck her ass out, the deeper she felt him inside her. “Ahhhh!” She cried out again. “Oooo, I’m going to cum, Doug!” As she spoke his name, that was all he needed to hear. Doug’s thick cock exploded in her ass. As soon as Chloe felt the first warm shot of cum as he thrust, her whole body stiffened. “Uhhhhh, ooohhhhhhh!” She cried. And then the ripples of ecstasy took over her body too. As her tight asshole puckered and squeezed rhythmically around Doug’s cock, Doug thrust deeper. “Oh my God!” She panted.

  Chloe pressed her hands against the steamed up window, her breath creating foggy patches over the steam. She panted. Doug’s naked body pressed hard against her, his cock trapped inside her still puckering ass.

  “Ohhh Chloe…” He murmured in her ear, his warm breath tickling her cheek.

  “Mmm.” She hummed happily. Doug pressed his lips to her cheek, kissing her tenderly.

  “I don’t know about you, but that was a first for me.” He said. Slowly he pulled back, prying his cock from her hungry ass.

  “You’ve never done that before?” Chloe asked, slightly excited at the prospect of being his first experience for something. With him being twenty years older than her, she wasn’t sure that there would be any of those.

  “Uh uh, you, love, are my first anal experience. In forty years I have never had the pleasure of a tight asshole around my cock.” After freeing himself, Doug gasped and leaned up against the window next to Chloe.

  “I like being a first.” Chloe said with a smile. She turned around to press her back against the cool window and she looked at him.

  “Oh, don’t worry, I can think of plenty more firsts for us to try together.” Doug said with a mischievous smile. Chloe grinned back.

  “I bet you can.”

  Chapter 9

  “Hey!” Chloe sat on the edge of her bed.

  “Hey.” Dana said.

  “You okay?” Chloe asked.

  “Not really…” Dana said. Chloe froze, sure that she had been found out by Dana.

  “What’s wrong?” Chloe said. She held her breath as she waited for Dana to answer.

  “I think my dad is having an affair…” Dana said. As the words hit Chloe’s ears, her eyes widened and she felt her heart beginning to thump loudly.

  “What?!” Chloe tried to sound surprised. “Why would you think that?” She asked. There was a brief pause.

  “Dad asked me to go home yesterday…” Chloe tried to think, the last time she had been to visit with Doug had been two days ago and he had repeated their lighthouse room incident.

  “Right…” Chloe said.

  “So I get there and he starts being super nice to me.” Dana sounded worried about this alone.

  “Dana, he’s always super nice to you, why would you think that meant he was having an affair?” Chloe really hoped that she could stee
r Dana away from her cheating theory.

  “Well we’re just talking and he starts telling me that he and mom are separating.” Dana sighed loudly.

  “Oh my God, why?” Chloe prayed that her acting was good enough to get her out of being caught playing a part in this twisted soap opera.

  “He wouldn’t say. He just said that they were having difficulties and they needed time away from each other.” Dana paused, waiting for some type of reaction from Chloe.

  “And you think it’s because your dad is cheating?”

  “What else could it be?” Dana asked.

  “I don’t know; it could be anything. People separate all the time for all kinds of reasons. He didn’t say anything about what it could be about?” Chloe pushed.

  “Nope. He just said they were having difficulties and it was between them.” Dana said.

  “Hmm, maybe it’s his way of trying to protect you?” Chloe offered.

  “I don’t know.” Dana said. “Something’s just weird about the whole thing.”

  “I agree…” Chloe couldn’t do anything else without raising suspicion. “But we have to assume that they know what they’re doing. I mean, the whole thing sucks but they’re both grown adults and sometimes shit just happens, you know?” Chloe said.

  “What the hell, Chloe? This is my parents we’re talking about, not just some couple on a TV show.” Dana sounded angry for a moment but then she burst in to tears.

  “Hey, don’t cry. I’m sorry. I was just trying to help. What I meant was…” Chloe sighed. “Want me to come and pick you up? We can go to the park?”

  “Please.” Dana sniffled down the phone.

  “I’ll be right there.” Chloe said.

  Goodman Park had been the girl’s secret meeting place since they first ran away together at the age of nine. They had huddled inside the small house at the top of the slide until the sun went down. When it started getting really dark out, the two of them decided that they probably weren’t angry enough to run away after all. Sneaking back to Dana’s house, they had put up a popup tent in the library instead. Every major event in the girls lives had taken place in that park, or at least been talked about there.