Reluctant Young Widow

Please be kind. This is my very first story to write. Thanks!

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She'd had too much to drink. She knew that, but how could she decline an offer from an old friend, especially one that had been friends with her and her husband when he was still living. Grace had been a widow for nearly a year, spending most of which trying to keep it together after losing a husband she had adored and at far too young an age. She was now a 32 year old widow with no kids and trying to readjust her life. This had been the first night she'd made herself accept an offer from a friend to go out to a bar. Aiden was a bartender at a little local dive that frequently had bands and "talent" nights and he had been inviting her pretty regularly. So, Grace got dressed up and went out, feeling a little more secure with this than venturing out on her own since she'd be the guest of the bartender. It had been so long, she had a hard time figuring out what to wear. After going through half of her closet she settled on a loose, knee length wrap-around skirt and matching spaghetti strap top. She added casual jewelry to complete her summery look and high heels to make the barstools a little easier to reach. Grace was 4'10" and pleasantly curvy. She was much less curvy now than she'd been a year ago, but at her height, wearing a 32DD and size 4 still looked filled out.

Aiden had been true to his word about taking care of her. She sat at the end of the bar, watching the band and had Aiden's company probably more often than was good for his tips for the night. They'd always had good chemistry, so it wasn't too surprising to her that they fell into their old flirting habits. He'd also made her some strong drinks, well disguised due to his bartending experience, which is what led to her current predicament. After realizing she'd had too much to drive and asking Aiden for the number to the cab service he recommended, she found herself accepting his offer to take her to his house. She'd been over to his place tons of times in the past, back when they were both happily married. Now she was a widow and he was divorced, new dynamics she hadn't thought about when she'd accepted both his offer to come out for a drink or for a ride. Now she was sitting on the couch, her head spinning, but still laughing and enjoying talking with Aiden. He was getting changed out of his work clothes and walked into the living room in pajama pants and shirtless. Aiden was about 6'2" and well built. Grace tried to nonchalantly look away, but Aiden saw her noticing his bare upper half. He just grinned and sat beside her on the couch, pretending there was nothing awry. After a couple minutes of chatting, she jabbed him in the ribs for making a short joke. He said "Oh is that how it is?" and began tickling both her sides. Grace laughed loudly and jerked around a little, trying to escape his grasp and Aiden took the opportunity to pull her onto his lap, so she was straddling him. He stopped tickling her after he had her positioned where he wanted her, just over his cock with her upper body close to his. He held onto her sides as he looked her eye to eye, inches away from her face.

"This is a bad idea," Grace said, after a few tense moments of looking him in the eye.

"Why is that?" Aiden replied as he ran one hand over her side and upper thigh, while the other pushed her long brown hair away from her neck, giving him access to plant small kisses on her neck and earlobe.

"Because," Grace answered, her breathing ragged, "It just is."

"You say that," Aiden whispered quietly in her ear as he ran his hand across her ass and under her skirt, "But let's see if you mean it."

He slipped two fingers under the edge of her thong, into her dripping wet pussy and began expertly working them. Grace had already put one hand on his chest and began weakly pushing away as his hand went under her skirt. Her feeble attempts to push him away stopped, along with her breathing, as he began massaging her clit. Once she found her breath again, she tried again to weakly move away, but he had one hand on the back of her neck, holding her close. The world was spinning even more as all this happened and Grace realized she hadn't taken everything into account, a little too late.

"Aiden," Grace whispered pleadingly.

"Grace," Aiden responded, "You can't tell me you're not attracted to me, we've always been attracted to each other. You also can't tell me you don't really want this or aren't enjoying it because it's obvious that you are." He let these words hang in the air for a minute as he slowly, almost nonchalantly worked his hand on her pussy and traced the side of her shoulder, neck and ear with his nose and lips. Once he arrived at her ear he whispered, "I think you need this. I think it's been too long for you and I think I'm going to make you enjoy this."

Grace felt as though she had utterly melted as he accosted her drunken senses, but she tried to pull herself back out of it to protest more. It wasn't just that she wasn't looking for this tonight or that she still hadn't gotten over her husband. It was that he had been the only man she'd been with and it had been a year since she'd done anything but pleasure herself. Part of her worried about whether any other man would think she was any good and whether it would feel like losing her virginity again if the guy didn't take it easy on her. "Aiden," she tried again, "The only man I've ever been with was my husband. I don't know if I'm ready for this."

"You are, and there's no better person for it. You know I care about you and you know I'm experienced enough to make this good," he said, as he moved to her mouth and began passionately kissing her. As they kissed he worked a couple fingers into her pussy and began pumping in and out, trying to further convince her and begin stretching her out for his huge cock at the same time.

She tried to pull back, but Aiden wrapped his fingers into her hair and gently, but firmly pulled her hair. Aiden had a good memory. He'd remembered when her husband had joked about how much she enjoyed having her hair pulled and how she liked to play rough. Her resolve evaporated the moment he pulled her hair. He knew how to do it right, a firm pull on a large section of hair, not just a few hairs. She began kissing him back and let the hands that were pushing against his chest, simply rest on his chest now. He continued for a few minutes, kissing her, pulling her hair and furiously working on her pussy, attempting to push her so far that she wouldn't deny her need once they changed positions or he began undressing her. When he was convinced she wouldn't bolt as soon as he loosened his grip, he let go of her hair and untied her wrap-around skirt, leaving it draped over her legs. He then moved his kissing down her neck and shoulder, quickly unsnapped her bra and pulled one breast up, out of the low cut shirt to begin kissing and sucking on it. Grace thought for a moment as he made this transition that she should stop him, but her intoxicated brain wasn't working fast enough for her to come to that decision before he had her nipple in her mouth and his expert sucking and licking instantly banished all other thought from her mind.

Aiden was hard as a rock underneath her now and let go of his hold on her pussy so he could change positions, putting her underneath him on the couch. She had a lot less room to stop him this way, if she changed her mind again and tried to enforce that decision. He knew when they moved past foreplay, into him actually entering her she would put up another fuss. He kept her mind off this inevitable conclusion by concentrating solely on her breasts, sucking and massaging them so well she thought she could orgasm any minute from this attention alone. When her moans became louder and she began breathing harder and squirming around a lot more, he started fingering her again, pushing three, then four fingers in, stretching her tiny pussy so it would be more able to accept his large cock when he was ready to fuck her. Grace was completely overcome with the sensations as the alcohol mixed with her lust and his knowing movements.

As he sucked on one breast and worked his fingers in her drenched pussy, he pulled his 9" rock hard cock out and moved closer to give himself better access to her pussy. He pulled his fingers out and lubed his dick with her wetness and eased down toward her and worked on planting kisses from her nipple up to her mouth. She kissed him and laid her hands on his chest again reflexively at his new position. She kissed him back to begin with, but as he wrapped one arm up around her back, placing his hand at the back of her head and used the other to guide his cock toward her pussy, she stopped kissing and began placing pressure against him. This resistance just pushed Aiden even more, made him want to fuck her small pussy that much harder. He finally pulled his mouth away from hers, allowing her to begin protesting, but immediately talked over her.

"You want this and you need this. I'm going to fuck you so good, no one else will ever come close to satisfying you."

"Aiden, no," she began, squirming underneath him, attempting to get leverage away from his throbbing cock, ready and waiting to enter her.

"It's going to happen, sweetheart. Try to relax so it can feel good the whole time, not just once you get with the program again." He grabbed a handful of her hair and squeezed her with his arm to keep her down where he wanted her as he slipped the tip of his long dick in and slowly began working it in. Grace started protesting more loudly, telling him to wait and trying to get her arms underneath him to push him away. He just rested the weight of his shoulders across her to keep her upper body fully restrained and wrapped an arm around her waist to position her hips where he wanted them as he slowly pumped more of his massive cock in her. Grace kept putting up a struggle, making each thrust hurt more than it should have, while helping him wiggle in with her movements.

"Just relax," Aiden whispered. "Relax."

Slowly Grace started relaxing, mostly because past experience told her it would hurt less if she did. She had somewhat sobered up during this and wasn't happy with Aiden at the moment. She was just thinking that she should have stopped him, then that she shouldn't have come over when he pulled his hand from around her waist and began working her clit again as he tried to get his entire cock in her, inch by inch. The combination of having a large cock expertly worked into her pussy and experienced fingers working her clit, she soon started forgetting how mad she was and could only register what was happening to her body. Sensing her give in, Aiden started working more in earnest toward stretching her out enough for his dick, pushing further with each stroke as he pulled her hair and nibbled her neck and ear. The more she got into things, the rougher he was- biting instead of kissing her neck, pulling her hair harder and wrenching one of her arms up to hold her wrist with a handful of her hair. Grace was losing herself completely. The dominating way he was taking her, holding her down, pulling her hair, but still not fucking her too hard to really hurt her was pushing her toward an orgasm. As he started feeling her build toward what he knew was an orgasm, Aiden fucked harder and faster, pushing past the control that was keeping him aware of her pain level. Grace was teetering so close to an orgasm that the new sensation of pain just drove her further, getting her closer to that peak.

"Oh yes!" she screamed. "God yes, that's it."

"You ready to take all of my dick?" Aiden asked dirtily as he picked up the pace, pumping to the speed he wanted.

"Oh, Oh, Ohhhhhhhhh, yes!" Grace screamed. Aiden forced the rest of his large cock in to the hilt with each thrust now, feeling himself building to cum having his entire dick in this small, tight pussy with her loving every second of being fucked as hard as he could fuck her.

Grace wordlessly screamed as she reach the peak, just about to go over the edge and Aiden pushed her over saying "Fuck yeah, take that dick in that tight little pussy. Damn you feel so good on my cock."

"Ohhhh, uuuuugggghhhhh yessss!"

Once Grace finished orgasming, Aiden knew he needed to finish before she calmed down from her bliss and began to feel the pain he was inflicting on her poor, beaten pussy. He pulled his head back far enough to get a good look at his little captive and watched his dick disappear inside her pussy a few times before he came in an explosive orgasm, pushing her back halfway off the couch as he finished. He slowly continued to pump in and out of her after he finished, both of them breathing heavily, his arms as the only support for her from the waist up. Once he finally looked her in the eye, he kissed her and pulled his head back to gauge her reaction. She smiled breathlessly back at him, shook her head and said "Next time I want to see what you think of my blowjob skills..."