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Chapter 52
by
Mr Nice Guy
What's next?
The Hotel
There was a hotel around the corner from the bar, a nice boutique affair that serviced clients travelling for business wanting to be near enough to the downtown core to walk to meetings, but far enough away from the rough neighbourhoods to still feel safe. Vanessa slapped her credit card down and filled out the paperwork for a room with a kind sized bed, then turned around to kiss her daughter's boyfriend while she reached around and felt his ass through his dress. She still thought of him like that, as her daughter's boyfriend. Perhaps after their date was over, after their time in the room together, she would change that. Maybe not, though. It was kind of fun. Kind of kinky.
"Your key card," the desk clerk called her attention back. She turned and smiled at the young woman patiently holding out her card, "Room 315. The elevator is on your left."
Vanessa took both her credit card and the two room cards from the clerk, thanked her, then pulled Tim by the hand toward the elevator. How long had it been since she had felt that way about a man? Hungry, eager, excited, and horny as hell. She wanted to throw Tim on the bed, rip that beautiful gown from his body, and find out what he had waiting for her underneath. Normally she didn't feel that way about men, but Tim was far hotter than the men she normally came in contact with. Short, slight, and made-up to look like a movie starlet, she couldn't help but feel wet when she allowed her eyes to linger on him for too long. His sleek red gown, showing off one long, smooth, sexy leg all the way up, made it worse. If she didn't have so much self control, she would have jumped him three times since the bar.
Nancy had been right. Tim was exactly what she needed. He made her feel young and sexy again! For too long she had played the role of boss, or the role of mom. What Vanessa wanted was to play the role of lover. Not to anyone, though, but to that hunk of a man. Her man. Well, their man. She would, of course, share him. How could she not? Nancy was crazy about him, so why would Vanessa deny her? There was plenty of Tim to go around.
The elevator door opened and she smiled to see that 315 was just two doors down the hallway. Soon she'd really get to see how much of Tim there was to go around. By the bulge in the front of his gown, though, she suspected that it was substantial. She hoped it was substantial.
A beep sounded from the door as she swiped the card, indicating that it was open. One push and Vanessa was inside, her daughter's boyfriend, her lover, right behind her. They didn't make it to the bed before they embraced again, greedy lips pressed up against each other, curious hands exploring bodies. They both began to moan, grinding, rubbing. Vanessa found the zipper on Tim's gown and soon it was pooled on the ground around his ankles. He, too, found her zipper, but the tight dress **** her to step away from him for a moment to take off.
Tossing the dress behind her, she took him in, tasting him with her eyes. Clad only in his strappy high-heeled shoes and a pair or red lace panties, Tim was the vision of manliness. Not a hair was on his body below his head, either shorn clean or unable to grow, just the way she liked it. His penis, fully erect and poking out of the top of his panties, looked huge against his small, hairless body. She loved her Nancy, but how had she landed a man like this?!
He was on her in a flash, falling into her embrace as she fell onto the oversized bed. He kissed her lips, he kissed her breasts, he kissed her groin. She wanted him so badly, but she wanted him to take her like a man takes a woman, at least for that first time. She wanted to be claimed. Pulling Tim up by his hair from where he has been kissing her inner thigh, she brought his lips back to hers. Then she reached down and pushed her panties aside, giving him room to slide into her.
"Fill me up," she said, "I need this. I need you."
And he did. Her legs wrapped around him, pulling him in, holding him tightly. He was wonderful. He was massive. In and out and in and out he thrust, their bodies becoming hot and sweaty. Shivers of pleasure ran through her as tiny orgasms began to happen, teasing her to want more and more. Tim's mascara began to run as he sweated, giving him a hot, rugged look, reminding Vanessa of a lumberjack or a sailor. He was a man's man.
And then, a few minutes after they hit the sheets, Tim began to cum. She could feel it inside of her, blasts of beautiful hot sperm filling her up. The feeling of his cock, the knowledge of his pleasure, pushed her over the edge. She began to scream.
"FUCK!" her voice pierced the room, "TIM!!!!"
And then they were done. Done that time. Vanessa had no intention on letting her lover, her daughter's boyfriend, off that easily. They had booked the room for the whole night, after all. Tim slid out of her and lay next to her panting. For a few minutes, neither Vanessa nor her date moved. They were caught in the moment, the pleasure of knowing what they had just done, what they had just felt. It was enough to just be near each other.
Then Tim slowly sat up, took a deep breath, and climbed off the bed. To the front door he went, his behind wagging as he walked carefully in his heels, to collected his clutch. Then he flipped on the light in the bathroom where she could hear him sighing.
"You alright, lover?" she called over the sound of running water, not wanting to leave the bed.
"Just fixing my face," he called back.
Of course. His makeup was a mess. Just like a man, just like her man, to make himself handsome for her again. She skootched herself up until her head was resting on a pillow and smiled contentedly, happy that Nancy had had such a good idea.
What's next?
The Trade-Off
Give Some to Get Some
Tim was lonely. Tim was . Tim made a decision that might lead him down some unexpected paths. Will he live a life of regret? Or will he get everything he ever wanted? Sometimes you have to give a little to get a little.
Updated on Oct 26, 2025
by Mr Nice Guy
Created on Nov 4, 2021
by Mr Nice Guy
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