Stuart was somewhat surprised when Penny called. Only a couple days before they’d had their first date and things were going nicely until she slipped up. They’d met and had dinner at a local establishment that He’d paid for. Afterwards they went back to her place and one thing led to another as they began making out. As things got more intimate it suddenly became clear Penny’s mind was on someone else when she passionately gasped, “Oh Leonard!”. Needless to say, Stuart was taken aback and Penny embarrassed. Things deteriorated from there and became helplessly awkward for the both of them. Stuart felt it best to leave at that point.

Stuart had known Penny for a few years and frequently saw her through mutual friends. Her relationship had been on again, off again with Leonard for some time. With their most recent break up, Stuart waited a reasonable amount of time and then asked Penny if she would be interested in going on a date. He half expected her to politely turn him down but instead she agreed. Within their social group Stuart and Penny had something in common in that they were not the brainiacs their other friends were. The others were career academia with high levels of education. Often times they found themselves on the fringes of conversations not really able to relate or keep up with the rest of the group. In many ways this was what contributed to Penny’s last break up with Leonard.

When Stuart came calling Penny was touched that he made the offer. He was a nice enough guy and never belittled her though she had to admit, there were times she laughed along with the others when he was the brunt of a joke. To say Penny pitied Stuart was perhaps a bit strong but appreciated his courage to ask her out. Going into the date she saw it as no more than a couple of friends spending some time together. At the very least Stuart wasn’t going to talk about things that were over her head.

As it turned out they had an enjoyable dinner and the wine, which Penny frequently enjoyed, relaxed things when they returned to her apartment. She enjoyed Stuart’s company but wasn’t physically attracted to him, however the wine lowered her inhibitions considerably when Stuart leaned towards her for a kiss. Penny couldn’t deny it was a very nice kiss and to be honest, after her break up, appreciated the attention. She reciprocated as the kissing continued mutually enjoyable up to the point of her Freudian slip. Unfortunately for Stuart it was clear, she still had feelings for Leonard. As much as she tried to put the gene back in the bottle Stuart felt it best to depart…..

……Stuart accepted Penny’s apology along with an understanding they didn’t need to go into long explanations. Penny was relieved he accepted as she wanted to make things right. They’d spend the time together and continue to be friends. They decided to take in an early movie and have dinner afterwards. Things went well as both of them put the past behind and enjoyed each other’s company once again. In some ways, the movie allowed them to be together and not have to do a lot of talking. Penny caressed Stuart’s arm as they watched which was re-assuring to him, she was enjoying their time together. The movie provided them something new to discuss over dinner and the conversation continued to be light hearted even though they took differing views on the outcome of the movie and how they would’ve handled things had they been the characters. The contrast in thoughts without it becoming a scientific equation was a blessing as well as enlightening. As per usual Penny sipped on a couple of glasses of wine over the course of the meal.

Once again Penny invited Stuart to her apartment. As hesitant as Stuart was, he agreed to come up. He’d been attracted to Penny from the first day they’d met but never expected her to show any interest in him, the fact they kissed at all on their first date was a miracle as far as he was concerned despite the unfortunate way things ended that night. In many ways Stuart was socially awkward, especially where women were concerned but Penny had generally been nice to him. He came out of his shell when he first asked her on the date, which Penny felt was very sweet of him. To be on a second date with her, despite her previous error, he knew he had to get past his fears and allow the date to unfold however things were meant to play out. Besides, it was clear Penny’s fopaux wasn’t deliberate or intended to hurt him.

Once to her apartment Penny offered Stuart some wine. He accepted as she poured for the both of them. Sitting on her couch they continued to chat. Penny consumed her wine at a much faster rate than Stuart did. Before long Penny was sitting with both legs bent and sort of under her, she’d moved in close to Stuart remembering how pleasurable their kissing had been on the previous date. Stuart, in his laid-back passive way kept casual until he stopped saying something mid-sentence as Penny leaned in. Their lips came together as they gently kissed again. This time, it was different, Penny’s lips were softer, more passionate. Stuart wasn’t sure if she had a greater appreciation for him or the wine and it’s effects. Stuart could taste the subtle alcohol on her breath making each kiss even more intimate. Bringing his hand to her waist he gently pulled her to him as Penny accommodated in response.

Stuart gently caressed Penny as they kissed but played a waiting game as to touching more intimate areas. Penny caressed similarly though her motions were slower. After a bit of non-stop kissing Penny had to break it off for a breath. Disengaging completely, Penny reached for her goblet of wine for another sip of liquid courage. Looking back at Stuart, she took him by the hand as she stood up, “OK…..lets go!” Penny announced in that playful voice Stuart had come to know and love over the years. Often, that voice came out when she really wanted something. Their hands almost pulled apart as Stuart shifted his weight to stand but eventually got to his feet, not sure where they were going but could only hope.

Penny led the way for the few steps that were necessary for them to enter her bedroom. The room was softly lit by the light of her small night stand lamp. Stopping at one corner of her bed, still holding Stuart’s hand she pulled him close behind her while bringing his hand up to her chest. Fully grasping Penny’s breast Stuart could feel her nipple harden through the material of her bra and top. With his other hand he pulled Penny’s golden hair aside as he began kissing along her neckline. Years of fantasies were paying off as he pleasured Penny. Penny craned her neck to allow him more bare flesh to kiss as he sent goose bumps down her arms and a pleasant sensation through her body and down her pelvis.

Soon Stuart could hear Penny’s deep breathes as she continued to open up to him sexually. He’d been massaging her breast with her hand still holding him there while he continued to kiss and caress her neckline with his tongue. With a slight pull on his hand Penny allowed it to drop free of her chest. In doing so Stuart brought his hands together just below the small of her back as he unclasped and unzipped her skirt. Every bit of the way Stuart half expected Penny to stop him in his tracks but she didn’t. As the material loosened from around her body, she shimmied a bit to help gravity do its part and for her skirt to drop to the floor. “Was this really happening?” Stuart thought to himself.

Penny put a knee on her bed as she leaned forward. The wine was having its effects and she had no desire to continue standing. Stuart remained where he was as she first knelt and then rolled to one side. In doing so he took in her beautiful ass. Her thong, a G string really, left nothing to the imagination as Stuart could make out the distinct sun-tanned areas versus what was covered by petite bikini bottoms as they tapered around her hips and between her legs. Before joining her, Stuart manned up enough to kick his shoes off and take down his own pants. Penny lay facing him but as Stuart got onto the bed, he knelt over her and came to rest along her far side. Penny rotated with him so she could continue to face him. No words were spoken as she leaned into Stuart and began kissing him again.

Stuart became bolder as they lay together. He returned to caressing Penny’s breasts again and would soon be unbuttoning her top. Penny paid it no mind as he slowly undressed her as her hand went up under his polo shirt and caressed his nipples and ran up and down his back. Stuart couldn’t help but get an erection in his briefs but didn’t dare reach down to adjust them or himself. Despite Penny’s overt behavior he still played things slow…..sort of.

They continued to kiss as Stuart’s hand started to wander more. He caressed her stomach with a light touch that made her giggle for a moment. “That tickles,” she cooed but didn’t resist or move his hand away. Gliding his hand around her hip and back up along her thigh, Penny continued her gentle attentions and kissing while Stuart continued to explore. A long-held curiosity of Stuarts was about to be answered. Over the years Stuart had vivid fantasizations of Penny and imagined the more intimate aspects of her body. As his fingers continued to explore, the inevitable happened as he came to the small triangular patch of material. The material covered only what was necessary. Gently pressing Stuart could sense there was nothing beteen flesh and fabric. With a couple quick movements his fingers slid just under the elastic at the top of the cotton material. Gently pushing down his fingers glided pubic bone across her pubic bone without the slightest hint of pubic hair. He had been wrong in assuming Penny had a small manicured muff.

In an attempt to not appear too egger Stuart withdrew his fingers from Penny’s thong with his more intimate knowledge of her. Bringing his hand up, Penny’s top now wide open, he caressed her other breast for the first time. Initially he felt the silky material of her bra with her hard nipple within. Many times, Stuart had observed Penny’s hardened nipples through her clothing and having to control a stiffy in his pants. A moment later his hand was fully under her bra and cupping her breast. Penny lay back taking in deep breaths as they stopped kissing. Stuart quickly investigated and determined her bra clasp was in front. Pulling his other arm out from around her, Stuart proceeded to unclasp Penny’s bra releasing her ample breasts. Again, the soft light of the bed lamp revealed her perky nipples as well as her tan lines. Stuart thoroughly enjoyed the privilege of taking in Penny’s body. Again, years of fantasizations and mental visualizations were becoming reality. He knew how precious the moment was.

Stuart kissed along Penny’s neckline down to her breast choosing one nipple where he gently licked and sucked. Not knowing how sensitive Penny’s nipples were, he maintained a delicate touch. Sliding a hand down her body yet again this time he was more deliberate. His fingers came to edge of Penny’s thong that ran along her thigh. The material tapered to a very narrow “V” between Penny’s legs and the elastic weak. It happened a bit quicker than Stuart intended but his fingers slipped under the material and into Penny’s labia. The warmth of the area intensified as he pushed in and was greeted with significant wetness. Penny’s body was ready for intercourse.

Suddenly Stuart felt a tugging of sorts. It was Penny wanting his polo off. Stuart withdrew his fingers from Penny’s crotch and responded to her desires. Raising up to pull his polo up and over his head, Penny did similar to remove her top and bra. Rather than laying down Penny continued to lean forward and before he knew what was happening, she pushed him to lay back down as her hands ran down the sides of his body and to his briefs. Penny could see his engorged penis through his underwear but now it was her turn to explore. “OH MY!” Penny exclaimed as she was pleasantly surprised to see Stuart’s manhood almost spring out of the constraining material of his whitey tighties . It wasn’t the biggest cock Penny had seen but it was still generous compared to many. Penny almost wanted to apologies for underestimating Stuart for so long but remained silent as she took the head of his penis into her mouth.

Stuart was in heaven. He’d never imagined something like this would ever happen where Penny was concerned. He'd asked her out on a lark and she’d accepted. If anything, maybe her little mistake on their first date was making this realization better than if things continued similarly on their first date. To be honest, Penny went into the second date knowing she needed to give Stuart something of herself but had no idea how far things would go. She deliberately drank more wine than usual to lower her inhibitions and for things to happen. If anything, they’d fool around a little bit, maybe he’d frigging her under her skirt but at some point, the date would end. As things developed, Stuart had impressed and Penny couldn’t deny it. Compared to other boyfriends as well as the occasional one-night stand, Stuart was truly a lover, a Casanova of sorts. Every step of the way, Stuart comported himself in a way Penny wished the various men in her life would treat her. However, there were times where she wanted sex and accepted what they gave.

There was no doubt Penny knew how to pleasure a man orally and she could’ve easily brought Stuart to climax but she decided to make him ride that fine line. In an effort to slow things down just a bit, Penny urged Stuart to take his briefs down and off so she could also take a breath. She was partially over him so she lifted herself off so Stuart could bend and facilitate the removal of his briefs. Once they were off, Stuart brought his hands to Penny’s waist for her to do similarly with her thong. With her facing down towards the end of the bed and not much room at the head board it became an awkward sequence of movements as Penny removed her thong, almost toppling onto Stuart in the process. The wine continuing to have its effect didn’t help either as Penny giggled a bit embarrassed with herself. Stuart couldn’t help but smile at her as she glanced back at him.

Red faced, Penny leaned forward again to take Stuart’s member into her mouth again. Stuart welcomed her continuing attention but soon nudged her. Penny resisted at first but then accommodated. Sliding himself down the bed a bit to give her more room for her legs, Penny moved with him and in the process re-aligned her body over his as she brought one leg over. The soft light in the room was just enough for Stuart to take in a beautiful view of Penny’s vagina her legs spread apart to straddle him. All inhibitions were now gone as Penny adjusted herself as she felt Stuart’s tongue begin to manipulate her. Brining his hands up he reached around to her ass. One middle finger made its way further between. Penny either was oblivious or enjoying as he gently massaged her tight little asshole.

Stuart took all of Penny’s sexuality in, her scent, her tasted her own unique womanhood. Licking and probing with his tongue he soon learned that Penny had a nice fleshy hood that covered a nice sized clitoris. It didn’t take much for him to work his tongue into her and give her clit a nice flick that Penny instantly reacted too. He had a nice technique using his nose as well that also gave Penny pleasure as well. It didn’t take long for her to slow her manipulations of Stuart’s cock and more specifically enjoy the pleasures he was giving her. Stuart, flicked her clit again.

Penny suddenly moved raising herself and creating a chill for both of them. Their skin together had created a fair amount of sweat and her sudden separation gave access to the ambient air. “You’re turn to be on top.” Penny exclaimed. Had she let him continue she would’ve cum in short order. She pulled her leg back over Stuart and then pivoted to lay down beside him. Again, Stuart got another view of her crotch during her maneuvering. After her proclamation and settling in next to him, he rose and rotated to come over Penny. Her leg closest to him went straight and flat against the bed as he came over. Penny simultaneously shifted her rear so she was more towards the middle of the bed as well. With Stuart now centered she bent and opened her legs for him.

Stuart considered leaning in against Penny to kiss her again but then changed his mind as he looked down at her and she back up at him knowing she wanted one thing. He gently moved back and forth searching with his cock what he sought. Penny could’ve assisted but gave him by gave him time….

…..They both knew instantaneously. A gentle steady push and Stuart felt the head of his penis enter Penny’s vagina. Slow methodical movements followed. Penny encouraged him along the way with her fingers. She soon closed her eyes as Penny began to enjoy her own pleasures with him inside of her. Stuart was in many ways numb as his fantasies continued to come true. He never in his wildest dreams ever imagined himself fucking Penny. He couldn’t help but to indulge in looking down and seeing himself slide into her. He must have been fixed on watching for a while as he looked back up at Penny’s face to which he was greeted with a devilish smile. A smile that told him it was OK and to enjoy, there was nothing to be ashamed of. They were two adults intimately enjoying each other.

Penny had suspected for a long time that Stuart had a thing for her. After all, how many men wouldn’t. She knew she was attractive and though she flaunted it at times to get the sexual attention from men when she needed it, Stuart was no different than any other heterosexual man having secret sexual desires of her. Stuart got more in tune with Penny’s responses. He would increase or slow himself down to her reactions and sounds. Her moans let him know that what he was doing was right. Penny couldn’t help but let it go as long as it could. Stuart would change something just enough to introduce new pleasurable sensations but not enough to get her to orgasm. It was like a long sexual massage that was long overdue and one that Stuart was willing to provide. There was nothing aggressive or abrupt about Stuart, he was kind and gentle and demonstrated a lot of longevity. His cock stayed hard the entire time and it absolutely felt great as he continued to gently thrust into her body.

Eventually Stuart quickened his pace more for to invigorate himself to full hardness again. He’d gotten her close enough it wouldn’t take much more. Stuart sensed Penny tightening and slowed his thrusts back down but became more deliberate, Penny responded with deep hard breaths, she was close. Another slight change and….

“AAAAAAAAaaaaaaaaaAAAAAAAAAaaaaa……..FUUUUCKKKKKKK…..FUUUUCKKKKKkk……HHHHhhhhhhhhaaaaaahhhh…….FFF…..FFFFFFUUUCCCK……..MMmmmmmm…..aaaaaaaaaa….MMMMMM…….mmmm”

Penny convulsed as Stuart went motionless with his cock deep inside of her. Completely in her own little world for the moment Penny couldn’t help but exclaim the expletives. Stuart enjoyed taking in Penny’s complete sexuality as he watched her writhe and shutter in full orgasm. Little did he know how intense Penny’s orgasm really was and that she rarely got to experience it on that level. More often than not the sex was over when the man came and she didn’t experience an orgasm at all. Still though, she enjoyed those experiences but they paled in comparison by far to what Stuart was giving her, “Oh…my god….he’s incredible!” Penny thought to hereself.

Stuart remained silent and still as Penny continued to writhe and convulsing gradually coming down from her sexual high. Her body eventually relaxed as she continued to breathe deeply in her afterglow, “You don’t know………how incredible……..you are.” Spoke Penny between breathes. Stuart couldn’t help but start to thrust again as he felt himself going a bit soft. Penny nodded her head in agreement with her eyes semi closed as she was still swimming in pleasure. Stuart still felt wonderful inside of her.

Satisfied he’d taken care of Penny, Stuart now indulged himself, looking down he watched himself continue to thrust into her body with a gentle but full movement. As he felt himself getting close, he looked up and saw into Penny’s eyes, she knew he was close as well. He could tell she was torn. He wanted nothing more than to cum inside of her, whether it be the beginning of something between them or just this one time. She said nothing but he knew the concern was there. The choice was his.

Animal instinct was taking over, he was meant to be given this opportunity and if possible, to inseminate and breed this woman. In this moment she had given herself to him and it was meant to be, it was his right. The intensions were clear, she must want it just as much as he does, she just can’t bring herself to say it. That has to be it, she wants it more than he does himself. Penny was the ultimate reward for his patience and kindness. She was more than that, she was his trophy. It would only bring them that much closer together, it all made sense. He was so close now……..

“MMMMMmmmmm….MMMMmmmm….mmmmmmmm”

Stuart made one quick movement, then reached down…….it only took a couple of strokes as Stuart shot a hot stream of cum across Penny’s belly almost to her breasts, "YYYYIIIIIIIIIIIIIIIKKKKKsss” she exclaimed, totally surprised. He continued to stroke himself as an abundance of semen ejaculated over Penny’s belly and pubic area.

Stuart saw the immediate relief on Penny’s face that he didn’t cum inside of her even though he likely left some precum behind. Penny pulled him towards her in an effort to hug and kiss him. He’d been a true gentleman the entire time. Stuart was more inclined to lay beside her as his arms had been holding him up much of the time and now needed the pressure off of them. Penny understood as she rolled to give him room to lay next to her. They held each other in the mutual afterglow of their sexual pleasures.

“I’ll be right back.” Said Penny as she turned to roll off the bed and head to her bathroom. Stuart took in the beautiful curvature of her ass. Even with the door partially closed Stuart could still hear her pee and the subsequent fumbling of the toilet paper roll and wiping. The water then ran for a bit, longer than Stuart had expected. Penny returned to her bedroom with a damp hand towel in hand. Stuart took her body, the first time he saw her fully in front of him, enjoying her slight pouch between her navel and pubic area. Penny hated it and tried hard to get rid of it through exercise but to Stuart it subconsciously represented fertility and sexuality.

Penny handed the hand towel to Stuart as she climbed back into bed. As implied, he wiped himself clean and realized he too needed to utilize the commode himself. Excusing himself, Stuart also headed to the bathroom. Similarly, Penny could hear him urinating, wipe and wash his hands as well. Returning to the bedroom it was his turn to accept the fact she would be viewing his body entirely. Penny had gotten under the covers and gestured for him to join her. Sliding under her comforter Stuart was pleased that Penny had remained nude. The teenage boy in him looking at Playboys came to the forefront as he looked forward to Penny getting out of bed in the morning and the view, he knew he would enjoy.

A tug on his wrist, Penny invited Stuart to roll and spoon with her. He accommodated as he gently pressed himself against her, she was very warm, his penis nestling somewhat into the upper crack of her ass cheeks. Soon she would be breathing deeply in a sound sleep. It would take Stuart a bit longer as he wondered what the morning would bring. Was this a one-time thing she felt she needed to do for him? Was she now his and for them to enjoy an intimate relationship? Anything could happen but as his eyes became heavy, Stuart knew one thing, he would make it last as long as he could…….