Sowing Her Wild Oats - part 5

Click here to read the previous parts of the story.

---

Just a few months ago, Andrea would have turned down Emmie's request to go to a club on a Saturday night. In fact, odds were good that Emmie wouldn't have bothered to ask.

Things had changed, though. Andrea was still engaged to Jay, but she'd opened herself to new experiences in the past few months. Nelson was one of those experiences and he'd opened Andrea's mind to a world of sexual pleasure she hadn't even known existed.

"I could be wrong," Emmie had texted on a Saturday morning, "but I feel like you might now be the kind of girl that wants to go out with her single friends on a Saturday night. Are you in tonight?"

"I am," Andrea replied without hesitation.

Several emojis came in the reply before Emmie added, "Wear what you want, of course, but you'll have more fun if it's at least a little bit sexy."

Jay came into the bedroom a little later as Andrea rifled through her outfits. "What's up?" he asked.

"Oh, I'm going out with Emmie and a few other girls tonight and I'm looking for something to wear."

He approached the bed - her outfit staging area - and picked up a dress that Andrea had already rejected. "I like this dress."

Andrea liked it too, but it was far too conservative for a night out. The high neck, the long sleeves, and the fact that it ended below her knees made it ideal for church or a grandparent's birthday party, but it was not ideal for a night out at a club.

"If you were a single guy and you saw a girl in that dress at a club, would you talk to her?" Andrea asked.

He seemed taken aback. "Wait, are you going out to get laid? I thought you were with Nelson?"

"I'm not with Nelson. I fuck him sometimes because it's amazing, but we're not exclusive. Though, to be fair, I'm not planning on fucking anyone tonight. I just want to wear something that will up the odds of a cute guy flirting with me."

Andrea had become familiar with the look on her fiancée’s face. It was a mixture of frustration, jealousy, and arousal. Sometimes one of those sensations seemed to dominate and on this particular afternoon Andrea saw more frustration than anything.

"And if I wanted to go out to a club tonight?" he asked. "If I wanted to flirt with a girl? If I wanted to try and fuck a girl?"

"Is that what you want?"

Jay set her dress down and sat on the bed. He was quiet as he said, "No."

Andrea took her pants off and straddled her fiancée. He smiled and grabbed her ass as she pulled her hips forward and kissed him softly.

"Do you sometimes feel like you don't know what you want, Jay? With regards to everything that's happened in the past few months, I mean?"

Before he could answer, Andrea kissed his neck softly. His hands moved under her sweater and up her back. He then moved to take her sweater off and she offered no resistance, leaving her in her bra and panties in his lap.

"I know it's hard, but I also know that you're really turned on when I come home from fucking Nelson. I know you like to hear the details. I know you like kissing me after you know I've had his cock in my mouth. I know you like licking my pussy after you know he's been inside me. I know you like fucking me while I tell you about how hard Nelson makes me cum."

He didn't have to say a word. Andrea knew all of it was true. She also knew that Jay was aroused in that moment because his dick felt like a steel pole poking into her.

Jay grabbed her ass, stood up, and spun around to lay Andrea in their bed. He peeled her panties off and crawled between her legs. He began to move his hips, to thrust gently against her pelvis, to stimulate both of them while he remained clothed. Andrea couldn't tell if he was silently asking for permission to fuck her or if he was simply working himself into a frenzy, but she liked the attention.

They fooled around like that for a few minutes before Jay backed out of the bed and began to undress. Andrea sat up, inched towards him, and grabbed his belt.

"We're not fucking," she said.

His face was a perfect picture of disappointment.

"I'm sorry. You can have me when I get back. I'm sure I'll be horny. I might be a little bit drunk. I'll make sure we have fun, though."

Andrea stood, kissed him, and unzipped his pants. She wondered if it was cruel to continue teasing him, but freeing his stiff cock and stroking him as their tongues danced was too thrilling to pass up on.

"What if I came home and told you I sucked someone's cock tonight?" she whispered.

Jay answered with a groan and Andrea dropped to her knees and looked up at him.

She kissed the head of his cock, sucked on it for a few moments, and asked, "What if I was on my knees just like this tonight? What if I was looking up at someone I'd met at a bar or club, someone I'd flirted with for a little while, someone I'd danced and made out with, someone that had gotten hard for me while we danced, someone that had turned me on so much that I just had to have him in my mouth?"

Jay reached down and ran his fingers through her hair. His hand rested on the back of her head for a moment and Andrea wondered if he'd be bold enough to try and direct her mouth to his cock, to try and slide his shaft down her throat like Nelson had once done. Part of her hoped that he would be, that he would show that he possessed the kind of alpha energy that made sex with Nelson so enthralling.

"It would turn me on," Jay said as his hand fell away from the back of her head and rested at his side. "It feels fucked up, but that would turn me on, Andrea. If you came home and told me all of that, I'd be turned on."

Andrea stood and kissed her fiancée. Then she tucked his cock back into his pants, zipped him up, and pulled him in for a lingering hug.

"It's not lost on me that this is hard for you," she said. "It's also not lost on me that the best sex of our relationship has come since I started fucking Nelson."

"I know," he replied softly.

Andrea stepped back and smiled as Jay glanced at her breasts. She was wearing a fairly plain bra, which only made his interest all the more delightful. "I want to wear something sexy tonight, but I don't really have anything that fits the bill, so I'm going shopping. I'm thinking a leather skirt and a tight, skimpy top. Maybe something that can be worn without a bra. Would you like to come shopping with me?"

She saw a flicker of interest. It wasn't enough to convince him to come along, though.

"If it's okay, I'd rather not," he said. "It's not that I'd hate it, it's just that the push and pull of all of this...I just think it would be too much."

Andrea kissed him on the cheek. "Of course. I understand. Is it okay if I text you some pictures, though? To get your opinion?"

Jay nodded. She was tempted to pull his cock out and suck on it a little more. The thought put a smile on her face. That's not the kind of woman she used to be. Not in the slightest. Things had changed, though. Nelson had changed her. Her eyes had been opened to a world of sexual pleasure, and not just her pleasure. Jay's pleasure. Nelson's pleasure. The kind of pleasure she could give a man. It made her feel good.

There'd be plenty of time for that, though, so Andrea gave him one more quick kiss, got dressed, and went shopping.

---

Andrea had never worn a leather skirt and she'd almost never worn a skirt that barely reached past the middle of her thighs. It had never felt like her style. She'd rarely worn four inch heels, either. She'd certainly never gone out in public in a skimpy top without a bra. She was wearing all of that as she walked up to the club, though, and for a moment her three friends didn't seem to recognize her.

"Holy shit!" Emmie finally said after a split second of confusion. "Andrea. You look so hot!"

Her two other friends agreed. The bouncer seemed to agree, too, as he waved them in ahead of the three dozen people waiting in line. It was the first time in Andrea's life she'd experienced a total confirmation of her sexiness and she entered the club bursting with confidence.

"So, are you looking to have fun tonight?" Emmie asked as they sidled up to the bar.

"Fun?"

"Are you planning on going home with someone tonight?" she clarified.

At that moment a cute guy - a really cute guy - leaned over the bar and looked right at Andrea. He smiled and her pulse quickened. She thought immediately of going home with him. She didn't do that sort of thing. Even with Nelson - where the whole purpose was to get fucked - she'd waited until the third date before taking the plunge.

Emmie turned to look at the guy staring at Andrea and her head whipped around as she smiled. "He's cute, but you're the hottest girl in here, Andrea. You could go home with damn near any guy. There's no reason to jump at the first one that smiles at you."

They ordered drinks and when the bartender returned he informed them that they'd been paid for. Men had bought drinks for Andrea before, but not without talking to her first. She liked that she looked sexy enough to inspire such desire in a man, or in many men, as Emmie had suggested.

"Does Jay know you're here?" Emmie shouted over the club's pounding music.

"He does. He helped me pick the outfit. Refused to actually go with me, but I sent him pictures and videos of the options and he said this one was the sexiest. I was honestly surprised he helped."

"I'm not."

"Really?"

Emmie looked at her like she was crazy. "Andrea, really? You've been fucking another guy for a few months and Jay hasn't left you yet. He's into it. He might be conflicted about it - guys aren't supposed to be into their fiancées fucking other men, after all - but he's into it. I mean, come on. You know he's into it."

Andrea smiled. "I told Jay that I wasn't going to fuck anyone tonight...but it's kind of all I can think about. I've never done a one night stand."

Emmie turned her head and Andrea followed. Sadie - one of the other two girls out with them for the evening - was already making out with a guy as they danced. She had her body pressed firmly against his and her tongue was obviously in his mouth.

"It can be a lot of fun," Emmie said. "It's not always great, to be honest, but it can be fun if you find the right guy. Just make sure you kiss him before you go home with him. You can tell a lot from the kiss."

The cute guy that had leaned over the bar to check out Andrea came over. He flashed a charming smile, extended his hand, and invited her to dance with him. She handed Emmie her drink and accepted his invitation.

Two songs later, his tongue was in her mouth. Hers was in his mouth, too. She'd initiated the kiss, in fact. She liked him. He was cute and a really good dancer. He moved his hands over her body in the most remarkable way, too. Every touch seemed designed to arouse her, to draw her deeper into her desire for him. None of it seemed designed exclusively to turn him on, which Andrea took as a good sign. He wasn't the sort of man that saw himself as God's gift to women. He understood that the best way to have great sex was to ensure that the woman was satisfied, or at least those were the conclusions she'd drawn from six minutes of dancing with him.

Eventually they made their way to a darker area of the club. They stopped dancing and segued into full-on making out. His body pressed against hers. His hands roaming. Him moaning as he discovered that she wasn't wearing a bra. Her moaning as he played with her tits through her soft, silky top. His cock pressing into her hip as his erection reached an impressive state of stiffness.

Emmie came over to let Andrea know they were going to a different club. She told her friend she'd be staying and wished Emmie a very happy evening.

Not long after, Andrea and her new friend left with the intention of going back to his place. She was going to have a one night stand and she couldn't have been more excited.

---

It was well after 2 a.m. when Andrea got home. She entered quietly, shut the door, and leaned against it as she thought of Chip - her partner for the evening - sweetly riding in the Uber with her before taking it back to his apartment. He'd been a little disappointed that she didn't want to spend the night, but she'd insisted that she had to get home. He then ordered a car and walked her down to the street. He surprised her by getting in and explained that he’d done so because he wanted her to feel safe, which was sweeter than he probably knew.

He was exceptionally nice, a fact she discovered after they'd fucked the first time. He made an impressive ice cream sundae, too, which they'd shared at his little kitchen table while recovering from the first round of deeply satisfying sex. She'd hung out a little after the second time - it turned out he was fun to be around - and then insisted she had to leave.

Now she was home. It was late. The apartment was quiet.

"Andrea?" Jay's voice rang out from the bedroom.

She smiled. He'd waited up. It was a small thing, but Andrea took it as a good sign. She pushed away from the door and followed her fiancée’s voice. He was in bed. He had on a t-shirt and boxer shorts and his phone rested against his chest.

"Did you have a good night?" he asked.

"Very good. Very, very good."

Jay moved to get up but Andrea stopped him. "Get naked," she said.

He stripped as she watched. She lifted her skirt around her waist and lowered her panties, leaving them on the floor as she crawled into the bed. She sat back on her knees just a few inches from Jay and he leaned over and kissed her thigh.

"You did more than give a blowjob, didn't you?" he asked.

She nodded.

His hand moved to his cock. He stroked himself. He was hard in almost no time.

"Did you think about me?" she asked.

"I did."

"Did you masturbate while thinking about me?"

"Yes," Jay admitted. “I didn’t cum, though.”

Andrea backed up a little and then leaned down and kissed him as she cupped his balls. "I went home with a guy. A guy I'd just met. He fucked me twice. I came four times. The sex was spectacular. So was all the dancing and kissing and foreplay at the club."

Jay stroked himself faster.

Andrea studied his face as she considered how she wanted to make her fiancée cum. She could ride his cock. She could suck him off. She could give him a handjob. She could sit on his face and have him eat her pussy as he masturbated. She could let him have her from behind. She could roll onto her back and invite him to fuck her as long and hard as he wanted. Her pussy was sore, though, as Chip had been quite vigorous, so riding Jay was the only option for sex.

"Was he...was he better than me?" Jay asked.

Andrea searched his face for the motivation behind the question. She quickly determined that desire had driven him to ask it. Desire fueled by the pleasure he took in her having sex with other men. Insecurity was undoubtedly mixed in, but Jay was turned on and seeking the thing that would give him the most satisfying orgasm.

She grasped the base of his cock and he moved his fingers away. Andrea kissed his neck and laid her body next to his. The warm leather of her skirt pressed against his bare thigh and she hoped her silky top felt spectacular against his chest and arm.

"He was much better than you," she whispered. "My pussy got wet as we danced at the club. It got wetter as we kissed. I was soaked by the time we were in the corner making out while he played with my tits."

Jay arched his back a little - always a surefire sign of intense arousal - and moaned. Andrea moaned, too, doing so to ensure her fiancée that she was just as turned on as he was. That probably wasn't true - Jay was almost certainly more aroused - but she wanted to reinforce his pleasure, to make him feel secure enough to fully indulge in it.

"He fucked me better than you do, Jay. The sexual chemistry was instantaneous. From the moment he slipped into my pussy I knew I'd have an incredible orgasm. He fucked me hard but not too hard. He kissed me the right way. He played with my tits the right way. Everything about it was incredible and I came so fucking hard...so fucking hard, baby."

Jay was close to cumming and Andrea changed her mind about the handjob. She straddled him, took his cock inside her, and began to rock her hips back and forth.

"Do you like that I went home with someone tonight, Jay? Do you like that your fiancée was a little bit slutty tonight?"

He nodded.

"Do you like that I sucked his dick to get him hard for me?"

"Fuck...yes!"

"Do you like that I made him cum twice? That your fiancée’s tight, perfect pussy made another man cum twice tonight?"

Jay climaxed and Andrea smiled as his grunts and groans flooded the bedroom. There was something joyful about making him cum that hard. It made her happy in a way that making Chip cum hadn't and Andrea quickly realized that it was her love for Jay - a deep, abiding love - that led to that happiness. It was nice to have made Chip cum, but getting Jay off in such a spectacular manner brought about a deep and genuine sense of satisfaction.

He opened his eyes and pulled her close for a kiss. She let her lips linger against his and welcomed his tongue into her mouth. It felt nice to be close to him, to be still with him inside her.

"You should really keep this outfit. It's amazing."

She laughed. "It's staying in my closet for quite some time. I imagine it will get plenty of use, though I'd like to buy more clothes like this. It was really fun to have grabbed the attention of so many guys tonight."

"I'd like to go shopping with you next time. I'm sorry I didn't go today."

Andrea caressed his face and smiled. "It would be a pleasure to have you come along."

After another lengthy kiss she climbed off of her fiancée and rushed to the bathroom to clean up.

The night had gone well and Jay seemed to be coming around to the notion that he found an unusual kind of pleasure in Andrea having sex with other men.

As his cum dripped out of her and into the toilet, Andrea wondered for the first time if she wanted to continue her sexual experimentations after she and Jay were married. Could she really give up the kind of sexual pleasure she'd discovered in the past few months, or was having great sex – the kind she’d never had with Jay –a necessary component of her happiness? If it was, could Jay deal with that fact or would he decline to marry her?

Those were questions that needed to be dealt with before they walked down the aisle, but Andrea had no sense of how to find an answer.