Meeting the Boss's Daughter Ch. 07

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Bryan's experience with an older woman.
2.6k words
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Part 7 of the 20 part series

Updated 06/08/2023
Created 11/10/2016
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I was lucky that by the time I had gone back down that afternoon, Phillip was busy with chatting with somebody that he had totally forgotten where I went. He gave me the rest of the afternoon to freely roam the exhibits or do whatever. I got myself a snack and coffee then headed back up to my room, took a quick shower, thoughts of the events with Katie flooding my mind.

I took a quick nap as well. By 6 o'clock, I was fixing the tie around my neck and almost ready for the awarding dinner. I was the first at our table. Every now and the then, somebody would come along for a quick chat about the work or share ideas about the creative design process. I managed to learn a thing or two.

I turned my head and saw Katie walking towards the table. It was always amazing how she appeared so different, so decent and proper and fresh and all those perfect adjectives even after an afternoon of wild fucking. I barely recognize her. I just see this perfect, glowing woman walking down the to me in a black, halter top dress and a uhh... some gown thing at the bottom.

I stood up as she reached me, smiled and pulled out the chair beside me for her to sit. She smiled and sat.

"My, you look decent," she joked.

"You look extraordinary," I replied, unable to keep my eyes off her. "How are you feeling?"

She gave me an innocent look, "what do you mean?"

She crossed her legs and immediately I noticed her skirt had a thigh-high slit.

She smacked my arm, "Is that all you ever think about?"

I looked up at her, surprised, "What? What do you mean? Of course not!"

She grinned and took a sip of the champagne the server had just handed her.

"So have you heard from Bryan?," I asked, curious.

She shook her head, "no, you didn't have to scare him off too much."

"What're you talking about," I asked, defensively, "I let him have some fun. I still think he's an ass though."

"You haven't even had a conversation with him," she answered.

"I don't need to," I answered, casually, "He treats you like crap. He's young, immature, you? You need, no, you deserve someone better."

She grinned, "Like you?"

For the first time, I actually felt my cheeks burn in embarrassment, "Nah, I could never be in the level of your stature."

"That's just silly!," she said, laughing loudly. It was the first time I actually witnessed her laugh, she was just so... Beautiful.

I looked at the crowd filling the room, "so what did you think about earlier? Are you alright? Are there... regrets or anything?"

She blushed, unsure of what to say, "Why are you asking now?"

I shrugged, "I'm just curious."

We chatted about lots of other things, school, her thoughts about working with or for her dad, her ideals... Knowing her just made me admire her even more. For a 21-year old, she was definitely a lot mature in her way of thinking. Somewhere along the line however, I found myself asking her, "Do you love him?"

She looked at me, surprised at the question, "I'm not really sure. Sometimes, I think."

"Sometimes?"

She shrugged, "Sometimes, I do, sometimes I don't."

"He treats you like crap."

"Yes, yes, you've said that before, countless times," she replied with a bit of laughter.

"Then, why the confusion about how you feel if you agree?"

Her cheeks turned crimson and a look of hesitation came across her face.

"Come on, I wouldn't judge your reasons, I just want to know how you could allow yourself to be treated that way when I'm positive there are so many others that would want to treat you better."

"What if I don't want to be treated better?"

I sat up straight in surprise at her revelation. "You'd rather be hurt and used?"

"I think that it's a punishment for the guilt I sometimes feel when I indulge in ... things."

"Things? Things you do... with me, for example?"

She said nothing, avoiding my stare.

"Don't you enjoy what I do to you?" The conversation was getting my pants in mild discomfort.

"I guess I... enjoy it a bit too much, more than I should, I suppose."

"And that's bad because...?"

She didn't answer and with good timing too, the program was starting and our table filled up with people from other companies. Her dad was on the VIP table with other CEOs or GMs.

A few tables away from them, Bryan sat staring, along with some of the other people from work, Stan and Amy included.

"Aren't YOU the boyfriend?," Stan asked him.

Bryan wasn't not really listening. His mind was filled with thoughts of what happened earlier. The images of her face in pleasure as she was cumming again and again despite the humiliation the was being done to her, to him. Seeing her with him now, he had wondered if it had all been a ploy. His jealousy was fueling, the anger building within.

"Who's that she's with?" he asked.

"He's one of us," Stan answered, his arm stretching around the back of Amy's chair. He looked at the far direction of where the two were sitting, "seems like they fancy each other, don't they?"

"Does her dad know?"

"I doubt it. You think dear, old daddy would want his little girl getting banged by someone twice her age?"

"I should tell him then."

Amy slides over to the seat beside him, slipping her hand around his chest, "Aww honey, you shouldn't. He's one of the best. Her father wouldn't believe you, especially if she took his side."

He could feel her breasts against his back, they were quite round and soft. "So I should just pretend?"

She smiled and leaned closer to his ear, "maybe you should just loosen up and have some fun while you're here." Her hand brushed against his crotch as she said it and slipped back into her seat.

Bryan turned back to her, a questioning look on his face. Only then did he notice how low her dress was that it revealed quite a lot of cleavage and how she sat with her legs apart as if to entice him to get in between. He had never thought about it before but seeing thjs older, hot woman offering herself to him... but then, he realized something. "Are you two together?"

They both laughed. "We just live the life, kid. She wants to add you in, that's up to her."

"Me and... Both of you?"

She shook her head, "No, I think I might like to try you first. Unless you want to share me with him."

He was silent, a bit hesitant.

She reached over a keycard. "if you change your mind, my room at 10."

Bryan entered the room slowly, using the key she had handed him. He wasn't sure why, he wasn't even sure he was excited but he was damned well curious about what she was offering. He closed the door.

"Perfect timing," a voice called out that made him jump in surprise.

She laughed pushing off the white robe from her body, revealing the black fishnet bodysuit she had on. It covered only her breasts and a very small area for panties. She had knee high, stiletto boots on as well.

His cock had hardened immediately. He had never seen anything like her, except in porn videos.

"Do like what you see?," she smiled as she walked over to him.

"I...," he couldn't finish. She stood inches from him and reached her hand right onto the bulge between his pants. He groaned loud.

She smiled, "that's a yes then. Strip now." She turned and walked over to the bed.

He did as he was told, quickly undoing his pants and shirt and briefs. He stood in place, naked.

She signaled for him to come over. As soon as he was right in front of her, she spread her legs. Only then did he realize that they were crotchless panties. He could see her clean, bare pussy slightly glistening.

"Show me how you eat pussy," she commanded, her eyes focused on his to prove she was seriously in charge.

He swallowed, nervously and knelt down. He could smell her juices. He leaned over and ran his let his tongue touch her pussy, slowly, hesitantly. He yelped when he felt her pull his hair backwards, her face was inches from his, "I don't like a tease. Do as I say or leave my room."

He nodded and she released him. This time, he delved right into her pussy, flicking her clit with his tongue, sucking hard on her juices. He heard her moan. He pushed her legs wider and dug his face into her, lapping at her juices, sliding his fingers into her, making her writhe and buck in pleasure as she came hard.

"Suck my juices, you cunt," she shouted out.

He had never been with a woman so wild. His cock was so hard now, he wanted to ram it right into her. He attempted to stand up but her legs weighed him down by the shoulders.

She sat up and looked at him, a frown on her face. "You don't get to decide when to stop. Do you hear me?"

He nodded, his hand trying to stroke the ache in his groin.

She laughed and stood up. "You boys just have no patience. Lie down!"

He happily obliged but then he heard a door open. He looked up and noticed the doorway to the adjoining room, in its frame stood a naked man with a mask around his face. He was fully erect with a black cock ring around his thick cock. He looked at her in question and that was when he noticed she was tying his ankles to the bedpost as well.

"No, please... I'm not gay. I...," he stammered, his face filled with fear.

She laughed as she climbed on top of him, her face inches away from his, "Don't you worry. He's not for you." She climbed even higher so her pussy was right on his face, rubbing it against him. She groaned as she felt his tongue move along her wet slit. She tied both his wrists in the same manner, grinding down on him. When she was done, she turned around, keeping her pussy on him and leaned down to take his cock into her mouth.

She felt him stir and groan into her pussy as her mouth covered his hard cock. With one hand around him, she stroked and sucked on him hungrily, pumping him up and down tight and fast, her mouth keeping pace. She could feel his hips thrusting upwards at her mouth but as soon as she felt him growing, ready to cum, she stops and releases him. She felt his disappointment as she climbed off him.

"You don't cum until I tell you to cum!" The look on his face made her wonder if he was about to cry. She had no time to pity him as a stronger hand pulled at her and forced her down on her knees. She took the masked man's cock into her mouth, sucking it like a bitch in heat, the way he liked her to. She would take him all in and fuck him with her mouth. He would thrust into her tight lips mercilessly, in and out, holding tightly onto her hair, controlling the movement. She felt his grip in her hair getting tighter and painful, she knew what that meant. She loosened her lips slightly around his cock as it squirted its load deep into her throat, dripping some between her cleavage.

He pulled her up and bent her over the bed, her face directly onto Bryan's cock. She leaned lower and sucked and licked his balls as she felt the massively thick cock behind her push into her wet pussy. With one violent thrust, it was all the way inside her. She sucked on the cock in front of her as the cock behind her started thrusting hard and deep into her, his balls slapping against her clit. Bryan had no control over anything just that he knew not to cum, but it was so hard not to. In front of him was this incredibly wild woman, sucking on his cock, her huge breasts slapping against his balls as she was being fucked mercilessly from behind by some masked man. Her loud moans and the man's grunts filled the room, along with the sounds of his balls slapping at her wet pussy. He had no lost count of how many times she had cum.

Suddenly, the man pulled her up. Bryan watched as she climbed onto him, lowering herself onto his hard, saliva-coated cock. He could feel her pussy pulsating from the hard fucking and numerous orgasms she had already had, she was already open from the massive cock but still, the warmth of her pussy felt so good around him. She moved up and down on him, grinding around him each time he was buried to the hilt in her. It took all his control not to cum right there.

She bent down, her face buried in his neck. He wanted to kiss her, to hold her but the restraints kept him open and void of any contact save for what she let him feel. He heard a loud rip and saw the masked man tearing at the part of the fabric covering her ass. He felt her pussy getting tighter, as if something was pushing it close around his cock. He realized then that the man was sliding his cock into her ass. It was so thick that her ass was getting stuffed so full, it was almost like their cocks were touching each other. He could feel the vibrations of the cock ring under his balls.

"Fuck," he muttered out.

The man pulled at her hair, pulling her up. He leaned backwards, letting her rock back and forth along their two cocks. He reached around her and toyed with her hard nipples, causing her to cry out, the more he toyed with her nipples, the wilder she became, the faster she rocked back and forth. He pushed her forward and knelt up, taking control of both bodies under him. He slid his cock in and out of her ass, at moderate speed first but then building up harder and faster, until he was pummeling her ass so violently, Bryan could feel the force impacting on him. Fuck, he too wanted it. He started thrusting his cock up and down into her pussy. Both cocks were ravaging her, she was held in place by the strong hands on her hair and breasts. She came so many times without rest.

She heard the masked man behind her grunting loudly, she knew he was close. The man under her too was struggling with his restraints, begging her to let him cum. She smiled to herself, and pumped back at both cocks, "cum for me now!"

Bryan cussed first as his cock erupted deep inside her, warm spurts of liquid filling her deep inside. The man behind her smacked her ass a few times, rammed his cock deep insider and shot his load in her as well.

Her holes were filled with so much cum. She squeezed at both their cocks, milking them some more until the one in her ass pulled out and she could only laugh as the man under her seemed to have passed out.

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