Sleeping With the Boss

by Sam Crescent

  “Watch me fuck you.” Julian pulled the pillows beneath her hips, propping her up so she would be able to watch.

  Heather watched his cock sink inside her pussy. The condom covered with her copious amounts of cum. She was so turned on by what she was seeing. He grabbed her hands slamming his cock inside her. They gripped each other, fucking their bodies together.

  “Fuck, look at your juicy pussy take me in. You want this, don’t you? You love fucking the boss.”

  “Yes,” she screamed.

  There were no words for her to describe what was happening to her body.

  “I’m not going to last.” He gave a growl, letting go of her hands to finger her clit. She felt on the brink of orgasm constantly around him. There was no way for her to stop this feeling. She wanted him that badly.

  Julian licked her cum off his finger then went back for more.

  “Come for me, baby. Let me hear it. You know how I love to hear you yell my name.” He used two fingers on her delicate clit, his touch relentless against her. “I love fucking you. You’re all mine.” He slammed inside her with each word.

  Heather loved it when he talked dirty to her.

  “Julian!” She yelled his name as she came apart. He fucked her harder until his cock pulsed inside her. The condom filled with his sperm. She didn’t know why he used the condom. He spent most of his time forgetting them with her.

  He collapsed on top of her, taking her farther up the bed.

  “I could fuck you forever. There is nowhere else I’d rather be,” he said. She rubbed his damp hair off his head.

  “I’m here ‘til you’ve had enough.” She stroked his hair. His breath was on her nipples. He got up on his arms staring down at her.

  “Do you love me?” he asked.

  She bit her lip. “Don’t make me answer that,” she said after a few silent minutes. Heather stared past his shoulder unable to think about the hurt inside her chest. She didn’t want their time to be ruined by her admission.

  “I can’t promise you anything, Heather. I told you that.”

  “I know. I didn’t say I loved you, Julian. Don’t be egotistical,” she said. Her fingers were crossed by her side. She wasn’t lying really.

  He stared at her for a little while longer. “As long as you know the score.”

  “You’re against commitment and prefer to sow your wild oats until you fall down dead, old and alone. I get it, Julian. I’m good for however long your dick gets hard for me. Now will you get off me so I can shower? I’ve got grime, work sweat, and everything else.” She shoved at his chest. Julian moved off her giving her space to move. He caught her wrist not letting her get out of the way.

  “I’ve got you all weekend, Heather. We’ll share the shower.”

  “Come on then.” She tugged him off the bed. Her nakedness no longer bothered her.

  He got up to stand next to her, his hand going to her cheek for her to look at him. “The last thing I want is to hurt you. I care for you, Heather.”

  “I know. Sometimes caring isn’t enough, but for now it’s more than I want.”

  They took a shower together, then made love before falling asleep in each other’s arms. Heather lay curled up against his chest as he held her.

  ****

  On Saturday Julian took her for a tour of the small island. They walked the beach without a care in the world. He was reeling from the shock of their situation. The women in his life never made him feel anything like the way Heather was doing. She made him want to be with her in the longer term. Each time he thought he was getting closer to moving on, the stronger his feelings grew.

  Until Heather entered his life, he hadn’t allowed a woman to sleep in his bed while he lay with her. Thursday night was the first time since they’d begun their affair that he’d slept alone. He didn’t like it. Her warm heat kept him at peace during the cold nights.

  The sun had set on their last night together. He stroked her hair where she lay on the bed.

  “I never thought I’d enjoy summer during winter.” She smiled.

  “I wouldn’t have come without you. I’ve enjoyed our time together,” he said.

  “It has been fun. Considering you’re an old man you know how to keep up.” She reached between his thighs to stroke his cock. Julian closed his eyes for a split second to enjoy her ministrations. He loved her hands on him. There was a lot about her that he loved. No, liked. He didn’t love anyone. Care was as far as he was willing to admit. All other emotions were pointless.

  Why?

  He cut the thought off before it had chance to spoil his last night with Heather. She’d been teasing him all day about her ass, making sly comments. He knew she’d been watching scenes of anal sex. She hadn’t deleted the links from his study computer at home. He liked the fact she was thinking about going further with him. The thought of her thinking about him while she watched the videos, turned him on.

  She lay naked. Their last love-making session permeated the air. He stroked down her back to her ass, cupping the cheeks. She gave a moan. “You love my ass, don’t you?”

  “Who wouldn’t?” He gave her left ass cheek a light tap. Her ass went a slightly pale shade of red, which quickly faded. Julian moved down the bed to attend as much attention to her ass as possible. “Open your legs.”

  Heather did as he asked. He loved how responsive she was with him. The bond between them was growing with every passing day.

  “Are you going to fuck my ass?” she asked.

  “Would you like me to fuck this ass?” He ran his fingers down her crack to her soaking wet pussy.

  “You’ve been talking about it for days now.”

  “That’s not an answer, baby. Do you want me to fuck your ass?” He cupped her ass in his hands, spreading her cheeks wide.

  She gave a guttural groan, her head buried in the sheets in front of her. He didn’t do anything else other than touch her intimately.

  “I’m not going to go any further, Heather. You’ve got to beg me for it.”

  “I can’t,” she said.

  Julian leaned over to her ear. “Yes, you can. All you need to do is say, ‘Julian, fuck my ass please’. And I’ll make you scream as I fuck your hot little ass.”

  He waited several moments for her to ask. While he was waiting, he played with her body. She responded to his touch instantly.

  “Julian, will you fuck my ass?” she asked.

  “Yes.” He nibbled at her neck, biting down. His cock pulsed with renewed arousal. When she was shaking with pleasure, he reached for the drawer where he’d stored the lube he needed. She was dripping wet, but the lube would provide extra lubrication to help him through.

  He rolled her over, her tits capturing his eye. Julian cupped her breasts in his palms. His thumb and finger teasing the buds of her nipples. She moaned, and her legs opening wider. He gazed down to see her juicy pussy open for him.

  Running his hands up and down her body, he leaned down and kissed her. “Thank you,” he said.

  “For what?”

  “For trusting me.” For her first time he wanted to stare into her eyes. He kissed her deeply on the lips. His tongue plunged inside her mouth as he caressed her whole body. He wanted her like jelly when he took her ass.

  She gave him everything he asked. Her body lay relaxed beneath him. He knew she trusted him with her body and her ass. The fact she’d never allowed another man into such a delicate part of her body meant a lot to him. He ran his hands down to her slit.

  He fingered her clit teasing her. In no time at all he had her whimpering and thrusting against him.

  “Please, don’t make me wait, Julian. I want you inside me.”

  “Tell me why?” he asked.

  She sent him a frustrated glare. He chuckled but didn’t budge from teasing her clit. Heather needed to open up more. He liked seeing her lose control. Julian knew she liked it when he lost control.

  “Because I’ve spent all my spare time preparing for this. You’ve
had your fingers up my ass, and I’ve watched it. I’m ready, Julian. Please, fuck my ass.” She yelled the last bit at him.

  He unscrewed the lid of the lube and smeared some on his fingers. “I’ve got to start by getting you well lubed up. I don’t want to hurt you. Grab a pillow, and put it under your ass.” Julian waited for her to follow his orders.

  She put the pillow under her.

  “Lift your legs up.” She followed his instructions. “This will feel a little cold at first.”

  Heather gasped as he pressed his fingers to her anus. “That’s it. Relax around me. Let me inside.”

  When he lubricated her ass, he grabbed a condom and quickly tore at the foil then rolled the condom over his cock. He took the tube of lube and smeared plenty over his latex-covered cock. There was more than he needed, but he wanted her to be comfortable. He wanted her to want him all the time.

  “I’m going to go slow and easy, okay.”

  She nodded her head.

  “Let me know if I’m going too hard.”

  “I will.”

  He pressed the head of his cock to her tight anal entrance. “Don’t tense up.” He saw the struggle she had, but she tried to open for him. When he got past the tight ring of muscles he paused to give her time to grow accustomed to him. “Push out,” he said.

  Heather pushed out, and he pressed his length slowly inside her.

  “Stop,” she said, her hand raised for him to stop. “You’re too big. Just give me a second.”

  Julian waited, stroking her thighs. The desire to push that last little bit was intense, but he held back.

  “Okay, I’m ready. Go slowly,” she said.

  Ever so slowly he entered her asshole. He took it slowly so he wouldn’t hurt her. Julian never took his eyes away from her as he sank the last few inches inside her ass. She licked her lips. Her eyes glazed over from desire. His grip tightened on her legs as he pushed the last bit of his cock inside. The action was hard and rough.

  “It’s okay. You’ve got me all, Heather. I’m inside you.”

  “You’re inside my ass?”

  “Yes. Thank you, baby.” He couldn’t form the words he felt inside of his heart. Heather was trusting him with one of the most precious parts of herself.

  “It feels so good.” Her ass tightened around him making him groan.

  “Here comes the fun part.” Julian began to ease out of her only to press back inside. He didn’t leave her snug channel for long. His pace was slow to begin with, allowing her to become accustomed to his cock in her ass.

  Her hands gripped his legs pulling him deeper inside her body. He set the pace giving her more than the last stroke. She whimpered, moaned, and screamed while thrashing on the bed. He wouldn’t give her anymore until she’d orgasmed.

  “Touch yourself,” he said.

  Julian watched her fingers glide between her thighs. Her pretty little clit was swollen with her need to find release. He licked his own lips knowing what she tasted like.

  “Finger your clit. I want to watch you come apart.” She stared at him as with even strokes he tunnelled in and out of her hot little asshole. The heat of her body gripped him. From the way her chest heaved and her eyes were glazed over he knew it was only a matter of time before she splintered apart.

  Her ass tightened around him. He broke their gaze to stare at her cunt. She was about to hurtle over the edge. Her pussy rippled in time to the build of her orgasm.

  “That’s it. Let me feel you.”

  She whimpered, then came apart. Her ass tightened around him to unbearable strength. Her cream leaked out of her pussy sliding down the perineum to cover the base of his cock.

  Before her orgasm finished, Julian fucked her ass. His strokes were gentle but firm. He’d been holding back his own orgasm in order for her to feel him inside her ass as she climaxed.

  He knew he wouldn’t last. There was no way he would ever be able to resist her.

  Her moans echoed around his head, her sounds addictive to him. She wanted the man and nothing more.

  He thrust inside her ass twice more, then growled as his cock jerked washing the condom inside her ass with his spunk. Julian collapsed over her. His head was cushioned by her heavy breasts. Everything about her was perfect to him. There was nothing he would change.

  A part of him wished he could be the man she needed. Their time would have to come to an end soon. She was starting to mean too much to him, and he wouldn’t allow himself to hurt her. The longer they were together the harder it would be to let her go.

  Hurting her wasn’t an option.

  “That was amazing,” she said. Her breath brushed against his hair.

  “I know. Thank you.”

  He looked up into her eyes. The trust and the love her saw in them made his throat tighten. She deserved more than this. Their time together would only ruin that part of her that was so special.

  “We’ve got to leave tomorrow,” he said.

  “I know. My boss wants me at work for Monday morning.” She gave him a smile. There was hope inside her heart. How could he squash her hope? Hurting her now would kill him.

  The threat from Elijah didn’t faze him. He respected the man for caring for his sister. Julian cupped her cheek. Her soft skin called to him. Could he keep going like this without giving her commitment?

  He knew it was hopeless, and yet, he refused to ruin what they had. The time would come when he’d have no choice.

  That day wasn’t today.

  “And you know how much I love to spank your ass. If you’re late I think that would be reasonable punishment enough.”

  She burst out laughing, the sound delightful to hear. There was a tenseness between them. He felt it and knew it was down to what had just happened. Until it could no longer last he would take advantage of their time together.

  Chapter Thirteen

  When they got back from their trip, everything went back to how it had been before they went away. Heather spent as much time with Julian as she could, their relationship growing stronger with each day. The days turned into weeks and the weeks turned into months. Before she knew what was happening, six month had passed, and she was still sleeping with her boss. Julian didn’t want to end things. She tried to talk about the future, but he didn’t want to talk about it. He didn’t want to ruin a good thing, and the moment they started analysing it, he felt it would be over. At least that is what Julian had said to her. He liked the time they spent together. She knew he did. They worked well together. She couldn’t deny their relationship for much longer.

  Her relationship with her friends was getting strained. It was only a matter of time before everything blew up in her face. For six months she’d been with Julian, and she hadn’t seen her friends as much. Elijah still lived in her house. Some of her clothes were at Julian’s.

  They were spending the weekend together at his house, again. Heather stared at him across the bathtub. He’d filled the large tub with hot water and bubbles. The days at work were getting harder. Keeping secrets was not her thing. She didn’t like doing it.

  “Here, some wine to relax you.” Julian poured her a flute of wine before getting in the tub next to her. Her hair was tied at the base of her neck in a clip.

  “Thank you. I need to relax.”

  “You’re over-thinking everything,” he said. He caught her hand kissing her knuckles. Her body tightened as pleasure rushed to every part of her body.

  “That’s easy for you to say. You’re used to this. I’m not.”

  “So you spend a little time with me.”

  “A little time? Julian, I spend every moment here. I’ve not slept in my own bed in over six months. My friends hate me, and you’re telling me I’m over-thinking things.” She took a sip of the wine. It tasted like vinegar. She didn’t have the energy to tell him she should be swallowing down tequila shots with her friends at Wade’s.

  “If it means that much to you, we’ll go to Wade’s this weekend. I’ll meet your friend
s.”

  “You’d do that?” she asked.

  “Yes.”

  She gave a smile. It was forced, but at least she’d get to see her friends. Heather took another sip of her wine. He stroked her shoulder and then her hair. His touch was soothing, yet annoying.

  “So all of your women know when you’ve had enough?” she asked, sipping a glass of wine. For the last six months she’d been putting off the inevitable. The longer they stayed together the quicker she was growing towards her best before date.

  “I’m not cruel, Heather. I give them fair warning. I’ll make sure they’re comfortable for a few months and then cease any further contact.” He stroked her neck as he sipped his own wine.

  “You don’t think that is cruel?” She shivered when he circled a nipple with his finger, his nail scraping the tender, red flesh. Her pussy pulsed with the fresh wave of desire.

  “Most if not all the women I date know the score. I’ve never made a promise I don’t intend to keep.”

  She licked her lips staring into her glass. The alcohol was going to her head, making her feel dizzy. It was moments like these, hearing his blunt talk, that made her regret her decision to be his.

  “What about me? Where do I come in?”

  He opened his mouth to talk then stopped and closed his lips. Heather drained her glass of wine, placing the glass carefully on the side of the bath tub. She wiped her lips to rid any excess. The fact he couldn’t answer her questions left her feeling lonely. Her friends had more than warned her about the path she was taking with him. She’d been a fool not to listen to them.

  “I don’t know,” he said, shrugging his shoulders.

  “Just don’t expect a ring?” She blew a few bubbles away. The tears she felt coming to the surface got clogged in her throat. “I need to get out. I’m turning into a prune.” She lifted out of the bath grabbing a towel to cover herself. Even though her nakedness didn’t bother her as much as it used to she suddenly felt too exposed to show so much flesh off.

  “Don’t go, Heather. I think conversations like this are only going to spoil our time together.” He caught her wrist before she had chance to pull away.