Not Her First Time

When Tucker came across Bailey’s Tinder profile, he immediately paused. She was striking, a beautiful dark-haired woman with bright blue eyes. She seemed a little reserved from what he could gather on her bio, and when he struck up a conversation with her, his suspicions were confirmed. Bailey was timid and a little shy, but sweet nonetheless.

Tucker’s jaw nearly fell to the floor at dinner a couple of nights later as Bailey came through the door at the French restaurant. She was dressed in a form-fitting black dress and black heels, her dark hair straight and sleek.

“Hi,” he said cheerfully, standing up as Bailey approached the table. “I’m Tucker.”

Bailey smiled, her cheeks flushing red even then. “Bailey.”

“I hope I picked an okay restaurant,” said Tucker, sitting back down and looking around. “This place had great reviews.”

Bailey looked around with him, nodding agreeably. “It looks good to me.”

“You look good.”

Bailey looked into his eyes, her expression unreadable. 

The conversation flowed over dinner, even through Bailey’s shyness. She was gorgeous and kind, but Tucker wondered if she might be a little too reserved for him. 

He was shocked at the end of the date when Bailey asked if he wanted to come back to her apartment. Women never invited him back after a first date, especially women like Bailey.

“It’s just a couple of blocks away,” she said, looking beautiful under the streetlights outside of the restaurant. “I walked here.”

Tucker shrugged his shoulders, taken aback, but pleasantly surprised. “Uh, yeah! That sounds great.”

When they arrived at Bailey’s apartment, they cuddled up in her bed as the TV played some reality show Tucker had no interest in. Besides, he was too busy deciding how he should move things along with Bailey. He didn’t want to come on too strong, especially because she seemed like she didn’t have too much experience, but he didn’t want to put her off by not making a move.

Finally, Tucker decided to lift her chin and kiss her in the heat of the moment. It was a soft, gentle kiss, and Bailey immediately giggled. 

“Is that okay?” Tucker asked quietly.

Bailey nodded. “Definitely okay.”

With that confirmation, Tucker rolled onto his side to begin making out with Bailey, as her hands began to undo his shirt buttons. 

Suddenly, he saw a whole new side to this woman. What started as a simple make-out session quickly turned into a frantic race to undress, with the two of them ripping off each other’s clothes. 

Bailey quickly got onto her stomach and began sucking on Tucker’s cock, moaning as she did so. She ran her tongue all along it, making it sloppy and wet. Tucker was in shock. He definitely hadn’t expected such a blowjob from Bailey. She certainly had some tricks up her sleeve.

“Fuck me,” said Bailey, sitting back on her heels and looking up at Tucker with those irresistible blue eyes.

Tucker reached around the small of her back and lowered her onto the bed, spreading her legs apart at the same time. He looked down at her pussy to see that it was already glistening wet. He pushed his length inside of her.

“Oh, fuck!” Bailey moaned, loudly. “You’re so big!” 

God, you feel so fucking good around my cock,” Tucker groaned, looking down to admire the way Bailey’s slim body writhed underneath him.

She had gorgeous round breasts that bounced as he thrust into her, and the sight became even hotter as Bailey began gently tugging at her nipples and squeezing her breasts together, as though putting on a show for Tucker.

“What do you think about anal?” Bailey asked, out of the blue.

Tucker slowed his thrusts and leaned forward so he was closer to her face. 

“Are you serious?” he said. 

Bailey bit her lip. “Mhm.”

“Sure! Yeah, let’s do it,” Tucker stammered, as Bailey pulled out the nightstand drawer to reveal a bottle of lube. 

“Do you want to do the honors?” she said, laughing, as she handed the bottle to Tucker.

He was in disbelief that this shy, soft-spoken woman was now asking him to fuck her ass. His heart racing, Tucker quickly coated his cock with the slick liquid and then rubbed a generous amount over Bailey’s asshole. He was pretty well-endowed and was nervous she wouldn’t be able to take it.

His fears soon dissipated the minute he started pressing his way inside of her tight hole. He went slowly, listening to Bailey’s sounds and watching her expression for signs of discomfort, but she was clearly enjoying every slow second of this.

“Mmm, I love a cock in my ass,” Bailey said, though it came out more like a blissful sigh.

Tucker watched as his entire, thick length disappeared inside of her. What a sexy sight to behold. Bailey had the perfect ass for it, too – so thick and round.

“Look at that,” he said, clicking his tongue as he started to fuck her slowly. “You’re perfect.”
Bailey smiled at him, looking relaxed and happy. Her face changed expressions quickly, though, as Tucker started to fuck her faster now, holding her legs back as he did so.

“Oh shit!” Bailey screamed, grabbing one of her pillows and burying her face in it. “Fuck yes!”

Tucker was fueled by her loud reaction, not slowing down even though his heart felt like it was going to pound out of his chest. He just about came when Bailey started rubbing her clit at the same time that he was fucking her ass. Adding the extra sensation did the trick.

“Yes, yes!” Bailey moaned. “Keep going just like that!”

She furiously rubbed at her clit as Tucker’s cock stretched out her asshole until she was finally shaking and screaming.

Tucker had never seen a woman cum like that before, with a cock in her ass. Only seconds after Bailey had come, Tucker was unleashing his load deep inside her, his cum filling up her asshole.

“Yessss,” Bailey said, “cum in my ass. Oh, that feels so good. . .”

“Shit,” breathed Tucker, the last drop of cum finally out of him.

He pulled out slowly and watched as some of his cum spilled out as he did so. He sat back on his heels and wiped his sweaty brow.

“You are. . . something else,” he laughed, looking into Bailey’s eyes. “I wasn’t expecting that.”

Bailey giggled and reached out to pull him down with her. “Is that a bad thing?”

“No, I like surprises.”

She leaned over to kiss him. “Lucky for you, I’ve got several.”

Tucker’s eyes widened. To his surprise, she made a move again, and within a few minutes, she was on top of him. Tucker grabbed her hips and she lowered her ass down onto his cock, riding it back and forth so that it nearly slipped out completely before she sank back down. Tucker watched in awe, relishing in the view in front of him, as well as the tight sensation of her asshole gripping his cock.

When she came again, quivering and shaking on top of him, Tucker thought back momentarily to how he almost hadn’t swiped on Bailey’s Tinder profile, and what a shame that would have been. . .

Best first date ever.

Authors note: I love the whole ‘shy girl comes out of her shell’ erotica theme and I really wanted Bailey to show Tucker what she was made of once he made a move. Writing this had me throbbing between the legs, I want this exact situation happening to me right now, anybody else? Tamsin 😘

I'm Tamsin (also known as Tammy), I'm the writer of all of these erotic stories. I write what turns me on and it used to be just for my personal use, but I decided to release it publically. I hope you enjoy and if you do remember to leave a comment and if you want more become a private member. If you want to know more about me, this is my personal page.

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