Woulda Coulda Shoulda
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Woulda, Shoulda, Coulda free porn video
She should’t have. Brianne shouldn’t have worn that dress. Not to a business event. A slinky black slip dress with a plunging neckline and side boob? Her 34Cs just hanging out there on display? Really? A Vegas club? Sure. The frat date party it was purchased for? OK. But the Summer Intern Thank You Party? Poor choice.
The second martini before dinner was probably a mistake. But her boss had gotten it for her. It would have been impolite to say, no. Politeness probably would not have been in question if she had reacted to him putting his hand on her exposed lower back. A flinch. A chastising look. Something. But all she managed was gooseflesh and a smile.
It was good that she pushed his hand away at dinner when he stroked her thigh under the table. But when the hand returned a few minutes later, she only giggled. And for sure when he slid his hand under her dress and caressed the firm, smooth globe of her ass cheek as they walked toward the exit ... A slap across his face would have been in order. But there was not a word of protest from Brianne.
The other interns grabbed Ubers. Brianne got into her boss’s Tesla. “It’s basically on the way home. I’ll just drop you,” he had said. That was a mistake. Did she really think she was just going to get dropped off at home?
“How about a nightcap?” he asked when they were underway, his car doing most of the driving. She should have said, “It’s getting late.” But she didn’t. “Do you like cognac?” She wasn’t sure she had ever had cognac, but she said yes. “I have some amazing stuff at my place. It’s right up the hill.” Brianne did not suggest anything different.
“Looks like my wife has gone to bed,” he said as they walked into the huge, modern house. His wife is here, Brianne thought. Well, that’s better. “We'll have to be very quiet,” he said with a wink. That wasn’t better.
Brianne’s knees shook as he gave her a tour of the elegant, expansive main floor. Why was she so nervous? Because he’s going to try to fuck me, she thought. She shouldn’t be there. But it would be awkward to leave too suddenly.
“Ah, now about that cognac. Let’s go down to the wine cellar.” They walked down a large staircase to another floor. There was a game room. And a full gym. And a theater room. Then more stairs. A huge basement, impeccably clean and organized. “OK, last one, I promise. There’s a sub-basement.” Brianne’s heart fluttered. Does he have a dungeon or something?
The stairwell opened into a small bar. There was a walk-in cigar humidor. Some rich leather club chairs. And a glass doorway. “Right through here.” The door opened into a giant wine cellar. It was easily larger than Brianne's whole apartment. So not a dungeon, then, she thought to herself. Was she disappointed? When Brianne walked in she was struck by cool air. Her nipples hardened. Her boss noticed, and smiled. "Yeah, it’s fifty-six degrees in here.” Once again she was reminded the dress had been a poor choice.
He walked her through row after row of bottles. He twisted some of them, at random, as they walked. Her high heels clicked on the stone floor. Her nipples only seemed to harden further. Was it just the cold? He said words that seemed almost random to her. “California. Cabernet. Pinot. Oregon. French. Bordeaux. Burgundy. Coat Do Rain, or something like that. Italian. Barollo. Brunello. Ports. Tawny.” She only half followed. She did not know wine. Or liquor, really. Everclear punch and seltzer was all she had learned at college. And she was distracted. Too distracted to really pay attention to his man-splaining about his expensive stuff. Was she anxious that he would make a move, or excited by the prospect?
“At last. Our mission. These are brandies. And … this little beauty … is what we’re after. You warm enough?” She wasn’t. She said she was. “Good. Then let’s just sip it here. We can be certain we won’t wake my wife if we are in here," he said with a mischievous side glance. He led her to a sitting area. A wine barrel with a glass top surrounded by barstools served as a serving table. An ornate cabinet held glasses of various shapes and sizes. There were two wine barrels on their side. “Purely decorative. I tried aging my own barrels once. A disaster.”
He poured the golden liquid into snifters. “Two hundred dollars,” he said as he handed her a glass.
“Two hundred dollars a bottle!” she asked, aghast.
“No. A glass. Two hundred dollars, a glass,” her boss said with pride. “Do you like it?”
It burned Brianne’s tongue and throat, and she felt it all the way down. She nodded.
“Spin it like this,” he said, rolling the snifter in his large hand. “It’s even better when it warms and opens up.” She tried to imitate him. Her boobs shook as she did so. Her boss noticed. This fucking dress, she thought.
He said words. She didn’t hear them. She adjusted to the burn of the drink and it tasted a little better. He leaned in and kissed her. She should have mentioned his wife. She should not have kissed him back. She should not have moaned into his mouth when he slipped a warm hand into her dress and cupped her breast.
He took the snifter from her. He slipped the spaghetti straps of her dress off her shoulders and it fell away. She could have clutched it to her. But she didn’t. In fact she stepped from it, leaving her in her high-heeled sandals and thong. He pulled her to him. He was aggressive now. He squeezed her ass. He sucked her hard nipples. He cupped her vulva as he French kissed her mouth. She should have played harder to get. She should have told him to slow down. She should not have mirrored his aggressiveness. It was not like her to reach out and fondle a man’s cock. But she did.
He broke away, stepping back to take her in. “My god, you are gorgeous. I fought so hard to not think of you that way as you walked around the office. But I did.” He fiddled with his phone, and speakers suddenly came to life, playing some R&B. He swayed as he pulled off his tie and jacket. Brianne took the opportunity to dance provocatively, doing her best impression of a stripper but for the absence of a pole. She shouldn’t have. But she did.
When her boss was shirtless he returned his attention to Brianne, holding her, kissing her, fondling her, then directing her to lie face down across one of the wine barrels. He pulled her thong over her pretty legs and heels, then nudged them wide apart. Brianne was completely exposed. He was obviously about to fuck her. She should have stopped him.
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