“How does this look babe?” Debbie added to the photo before sending it.
A few moments later the reply came in and she read it, “Looks great, but dump the stockings, I want to feel those silky smooth legs.”
“Ok!” she messaged back, adding in a few heart emoji to go along with it.
It was so great to have a boyfriend that finally cared, and not just about the big stuff, but the little things as well. Things like the stockings, what had she been thinking after all? God, how would he have been able to feel all the effort she’d put in getting laser hair removal if her legs were covered up?
She wiggled her ass back in to her bedroom, sat on her bed, took her shoes off and then slipped the stockings off as well. After putting her shoes back on, she walked over to the trash and tossed the stockings in to it.
It was all the little things like this that made Tom such a perfect match for her, he was always giving her little tidbits of advice that made he better in some way.
Six months ago, when she’d signed up to “The Perfect Match” dating service, she’d been skeptical to say the least. She was a die hard feminist who hadn’t shaved any part of her body since she was a teenager, and she was pretty sure at some deep dark level, she hated men. How was some new dating website going to find her a perfect match… guaranteed?
At first, it had been like all the other dating services she’d tried, full of dumb jocks, misogynistic professionals, and vapid celebrities. Well the celebrities thing was different at least, they had some of the most eligible male celebrities in the world on the service. They were blocked of course, they had to reach out to you before you could communicate with them, but it was kinda fun to look over their profiles and fantasize a little.
Then, while browsing, she’d had a popup window appear with Candy, personal VIP concierge for the service chatting with her. Candy had a particular client interested in her and wanted to set them up on a date.
Candy had sent Debbie his profile link and after a weird flash of the screen he’d appeared and Debbie couldn’t believe her luck! He was gorgeous! Well, ok, maybe not gorgeous in the traditional sense like Brad Pitt or George Clooney, but the longer she looked at his profile picture, the wetter her pussy got.
The butterflies really started to swarm in her tummy when she read the brief profile he’d written.
“Looking for a hot little slut that loves to be groped in public. Must be willing to take suggestions about her appearance and attitude and make the appropriate changes.”
Debbie quickly replied to Candy that she was so excited to met Tom and couldn’t wait for their date.
That first date had been heaven, Tom had picked her up and started critiquing everything about her right away. Her conservative dress, her lifeless short hair, her flats, her lack of makeup, everything. But it was the next thing that he did that cinched it for her. He’d simply stepped up right in front of her, reached around and grabbed her ass, then gave it a quick smack.
She’d gasped and swooned in to his arms. She looked up in to his eyes, parted her lips and spoke, “Please Tom, do it again…”
To which he simply did. And not just there on her door step, but all throughout the date. He grabbed her ass, he grabbed her breasts, he grabbed her hair, he grabbed her head and twisted it around to kiss her without asking. She was desperately horny by the end of the night and when he dropped her off, she begged him to come inside and continue.
He declined, only saying she had a lot of work to do before he’d enter her home.
She’d spent the next several weeks messaging him, sending him photos, telling him what she was changing, asking for feedback and suggestions, and he always responded promptly.
It was almost a month later when he agreed to a second date. She’d already bought new clothes, gone and had her hair died and extensions added, had her first round of laser hair removal, and spent hours online practicing with her new makeup.
This time when he arrived, she had worn a short skirt, a tight top and heels. He showed his appreciation by keeping his hands roaming all over her body throughout the date. And when they returned to her place, he came inside, bent her over the living room couch and fucked her right there were any of her neighbours walking by would see her.
She came so hard she thought she might have died.
Since then she’d worked on herself, under Tom’s direction of course, constantly. She was up to five days at the gym, she had to take a couple weeks off when she’d gotten her breasts done. She was watching a lot of porn as well to learn how to act properly when Tom was fucking her. She was also spending most of her time at home completely naked, without the blinds down, so her neighbours could get a good look at her when they walked by.
Tom had suggested just the other day she should start flashing them when she went out on her run and just the thought made her pussy wet.
The knock at her front door disturbed her thoughts and she raced to the front door and swung it open, Tom was standing there and she pushed right up against him. He smiled and grabbed her ass and pulled her outside as she grabbed the door and closed it behind her.
He took a step back and grabbed the lower band of her top and pulled it out and up over her breasts, “God I can’t get enough of those tits Debbie.” he said and grabbed hold of them.
She let out a moan and let her head lean back a bit, “Oh god baby, squeeze those big fake tits! I love showing them off for you baby!”
He continued for a few minutes until he let go, grabbed her by the hips and twirled her around. With one hand on her abs, he leaned her forward and she reached out and placed her hands against the door. With his foot he kicked her feet apart and then pulled her short shorts down until they would go no farther.
His one hand slipped between her legs and found her pussy, the other grabbed a hold of her ass and squeezed.
“Mmmmmmm… god that feels so good baby, squeeze that ass, put those fingers in my hot little pussy…”
They stood there, on her front door step, for several minutes as he groped and played with her body. She knew the neighbours would be watching, he did this every time he came over and she loved every moment of it.
But eventually he pulled her hands away, pulled up her shorts, and smacked her ass, “Ok, that’s enough for now, time to get going slut.”
She stood up and fixed the rest of her outfit before looping her arm through his and leaning in to him, “Ok baby, like, where are we going tonight?” she asked.
He smiled and looked down at her, “Oh, your going to love it. It’s a new private club where pretty much anything goes. I’m gonna have you naked, on my lap, playing with your tits and pussy for hours! It’s going to be great!”
“Oh my god babe, that sounds amazing! Are lots of guys going to be watching you grope me? Cause you know how horny that makes me babe!”
“You know there will be slut, I can’t wait to see how wet your pussy is by the end of the night.”
Debbie wiggled her way around to the passenger side of the car and slipped inside, as Tom walked around to the drivers side, all she could think about was how luck she was to have found her perfect match in Tom.