Better the Second Time Around Ch. 01

Author's note:

Like many of you reading this, I have been a faithful follower of BusyBadger's series, A New Way of Seeing Things for nearly four years. I always thought I would like to try writing for Literotica too, even though I have little experience writing fiction, especially erotica. A recent medical event, that fortunately I fully recovered from, made me decide to get out the old bucket list and get started on it. Since writing a series on Literotica was on the list, here goes.

I have no idea how long the series will be but hope I can keep it going for a while. After writing the first three chapters, I feel like Dave & Lisa are good friends that I care about even though they are of course, fictional. So, if you like them too, I'll keep writing as long as their story lasts. I welcome comments and suggestions but please understand that I'm a romantic at heart and believe good sex is a result of love, affection and consideration between those involved. If you agree with me on that, I think you will enjoy Dave & Lisa's story, hopefully even the parts without sex. If not, well thanks for stopping by, but you might enjoy some of the other stories in Literotica more. Either way, thanks!

Setting: A small city in the Midwest.

Characters:

David (Dave) Thompson, age 52, widower for three years. Two grown children. Dave is the owner/operator of a commercial printing business and is a part time professional photographer.

Lisa Williamson, age 50, divorced for 10 years. Three grown children. Lisa is a high school English teacher.

Melissa Thompson, age 25, daughter of Dave, unmarried.

Chris Thompson, age 23, son of Dave, unmarried

Matthew Williamson, age 27, son of Lisa, unmarried.

Rachel McAllister, age 25, daughter of Lisa, wife of Travis.

Travis McAllister, age 26, husband of Rachel.

Stephanie Williamson, age 22, unmarried.

Synopsis: Dave and Lisa meet when he is asked to photograph the wedding of Lisa's daughter, Rachel. A difficult divorce had left Lisa feeling unsure of herself, undesirable and not very sexy. Dave strongly disagrees with her self-assessment and begins to help her discover how beautiful and sexy she really is.

Chapter 1 Lisa Discovers Her Sexy Side—With Some Help

Lisa Williamson was nervous. She didn't like having her picture taken. That was true in part because she was not comfortable with the way she looked. After her children were born, she never seemed to be able to get off the few extra pounds she had gained and to her embarrassment, most of those extra pounds eventually went to her chest. Over the years, her bra size had gone from the 32 B she wore on her wedding day many years ago, to the 36 D she wore today. Ok, she was really a 36 DD but only busty young women or old ladies wore cup size DD and since she was neither, (50 is NOT old, she kept telling herself) she usually squeezed herself into a 36D.

Lisa was blessed with long auburn hair and to her, this was her saving grace. When she was younger, her hair seemed to be what attracted men first. She knew she had a nice body back then, but nothing spectacular. It was her hair that had gotten her noticed. She was grateful that her auburn hair was still what people noticed first, not her extra pounds.

Of course, her ex-husband John had not complained about the extra pounds—right up to the day he announced he was in love with someone else and wanted a divorce. Then he had plenty to say, suggesting it was her fault that he had an affair with a woman ten years younger than she, because Lisa had "let herself go." This from a man whose belt size had grown from a 30 when they married to a 44 when they divorced. Lisa might be an English teacher but her math was good enough to know that John's waist was almost half again bigger than it was when she married him. "And his penis was half again smaller," the slightly bitter side of her snickered.

That was ten years ago. After the divorce was finalized, John moved to Chicago, taking his new wife with him and leaving Lisa to finish raising their three children. Fortunately, they were good kids and had turned out OK. The only one she really worried about was Stephanie. She was only 12 when her father left and navigating her teen years without a father in the house seemed to have been a challenge for her. This was reflected in the way she talked and dressed. Lisa feared she was trying to use sex to attract attention from men; seeking the wrong kind of attention from them because she never got the right kind of attention from her father.

Lisa sighed and brought her attention back to the matter at hand. She had to get ready for the photographer—her fiancé. How had she ever let Dave talk her into this? Yes, he was a part time professional photographer, but still...

That was how they had met. He was the photographer for her daughter Rachel's wedding earlier that year. His daughter, Melissa, was one of Rachel's bridesmaids and when the photographer Lisa had hired backed out at the last minute, Rachel saved the day by asking her father, Dave Thompson, to photograph the wedding. He was an amazing photographer, making everyone comfortable and knowing just how to arrange the bridal party to get the best results. His candid photos during the wedding rehearsal and again at the reception captured moments in time that had become cherished memories.

When they were reviewing the photos, trying to decide which ones to have printed for the album, Lisa noticed there were a lot of her, not as many as there were of the bride of course, but still there seemed to be a lot more mother of the bride pictures than was usual. "I'm just imagining things," she thought to herself—until her younger daughter, Stephanie said, "Wow! There sure are a lot of photos of you Mom. I think the photographer has a crush on you!"

"Don't be silly, Steph."

"No, she's right Mom," Rachel chimed in, "You're in a lot of the photos and you look great."

"Yeah, Mom," Steph said, "And look at your cleavage! You look sexy! No wonder the photographer has the hots for you."

"Steph!"

Lisa could feel her face redden, especially because her son-in-law Travis had been looking at the photos with them. Because she was uncomfortable with the size of her breasts, she tended to dress conservatively, trying to hide them. Her daughters had talked her into a dress for the wedding that was modest by today's standards but felt a bit risqué to her, showing a hint of the cleavage that she had tried so hard to hide over the years. And if she was honest, when she leaned forward a bit, more than just a hint of her cleavage could be seen.

"Maybe if you'd showed off your boobs a little more, your husband wouldn't have left you," she thought to herself, followed quickly by "John didn't leave me because I didn't show my boobs enough. He left because he was a jerk! Anyway, he didn't ask me to show my boobs. If fact, the last few years he rarely even looked at them."

Bringing her thoughts back to the present, Lisa felt the butterflies in her stomach make their presence known as she again thought about the photos Dave was preparing to take. It turned out Stephanie had been right about why there were so many of her in the wedding photos. Soon after the wedding, Dave called Lisa, asking how they liked the photos and ended up apologizing for taking so many of her. "I just couldn't help myself," he said. "You looked so beautiful and the lens was just drawn to you." They talked for over an hour and before the conversation ended, she found that she had agreed to go on a date with him.

Now, just three short months later, she and her daughters were planning her wedding. Which once more brought her mind back to the dress waiting for her. When Dave had talked her into letting him take some "engagement" photos of her, he specifically asked her to wear the dress she had worn to Rachel's wedding—with another request. With a twinkle in his eye he asked her to wear a bra that enhanced the cleavage peaking from her dress. Embarrassed that he would ask such a thing, she shyly told him, "I don't even have a bra like that."

Handing her his credit card, he looked her in the eyes and said, "Buy one." His smile widening, he lowered his voice and said, "Buy some sexy panties too!"

"Sexy panties!" she exclaimed, "You won't even see them under the dress."

"But it will drive me crazy knowing you're wearing them."

So here she was, wearing a bra and panty set that would be more appropriate for her daughters than for her 50-year-old body. Looking at herself in the mirror, she tried to objectively evaluate the image before her. "Actually, not too bad considering my age," she thought. "Sure, my boobs are bigger than I would like, and my hips are those of a woman who bore three children, but my stomach is still pretty flat and my legs look pretty good, if I do say so myself." Although she couldn't bring herself to think she was still pretty, she did like the way her hair framed her face.

She looked more closely at the bra and panties, thinking, "I bet Dave would love to see me wearing just these, without the dress. Just a couple more months, my love."

Lisa had been a virgin when she and John were married. She had "saved herself" for her first husband and he was the only man she had been with. Perhaps because of that, she felt a self-imposed pressure to wait until they were married to have sex with Dave. She knew it was old fashioned but she felt like it was the thing to do. Or maybe she was just scared.

John had not been much more experienced and their lovemaking had never progressed much past brief foreplay and the standard missionary position. "Maybe if I had been more adventurous in bed, he wouldn't have left me," she thought, continuing her earlier self-recrimination. "Maybe he needed more. Maybe I needed more!" She hoped she could be everything Dave wanted and needed and secretly hoped that he could stoke the embers of sexuality that had recently been rekindled in her.

As she continued her self-evaluation, her hands brushed the swell of her breasts jutting out from her new bra, a blush involuntarily coloring her chest as she remembered the day she bought it. The day that started to change how she looked at herself. The day she started to believe she might still have a chance to be the sexy woman she secretly longed to be.

***

She had travelled to another city nearly an hour away because she was too embarrassed to buy sexy underwear in the small city they lived in. After all, she was a school teacher and might run into one of her former students or even worse, the parent of a current student working or shopping in one of the few clothing stores available here. She had driven to a woman's boutique located in a large mall, praying she would not run into someone she knew. She even planned her arrival to be near closing time to reduce the chance of that.

When she arrived at the boutique, she went straight to the lingerie department and began to peruse the bras and panties trying to find something "sexy" in her size. Frustration set in quickly. "Apparently, women my age with large breasts are not supposed to look sexy," she fumed. Just as she was about to give up, a young woman, probably in her early 30s, came up to her and asked if she could help. Her face coloring, Lisa quickly said, "No thank you. I'm just looking." The woman mentioned her name was Alexa and that if she changed her mind, please let her know.

As Alexa turned to leave, Lisa quickly blurted, "No, wait. I guess I do need some help! I'm looking for something for my fiancé. No, I mean not for my fiancé, for me. My fiancé is a man of course. I'm looking for something to wear for him. Well, not that he will see it, I'll be wearing a dress. But he wanted me to get a sexy bra and panties to wear under the dress so he will know I'm wearing them while he takes my picture and I..." She stopped, realizing she was rambling almost incoherently.

Alexa placed her hand on Lisa's arm and said kindly, "I think I understand. Now, what's your name?"

"Lisa," she replied.

"Ok, Lisa, how about letting me help you find something that he is sure to like— whenever he gets to see it. Ok?"

Gratefully, Lisa nodded her head. "I'm sorry to be so silly," she said, "but this is going to be my second marriage and the first didn't end so well and my fiancé Dave is a really special guy and I want to look sexy for him and..." She paused then said, "I'm rambling again, aren't I?"

"That's ok, "Alexa replied, "I think its sweet that you want to look sexy for, uh, Dave—is that right? Especially at your age. Wait, that didn't come out right. I mean, you are a beautiful, mature woman and I just hope I look half as good as I do when I'm your age. And I hope I have someone special like Dave to look beautiful for. He's a lucky man." This last statement was made as Alexa's eyes swept down and back up Lisa's body, stopping briefly on her breasts before returning to her eyes.

At this, Lisa felt a little tingle go through her body, focusing on her nipples and between her legs. "What was that?" Lisa wondered to herself. "Was she checking me out?" "No, she's not," she quickly thought. "Besides, even if she is, I'm not attracted to her, she's a woman!" "Deny all you want," her naughty side answered, "but your body says differently."

With a slight shake of her head to bring her back to reality, Lisa replied, "Thanks, but I'm the lucky one."

"So Lisa," Alexa said, "what did you have in mind for Dave?

"Well," Lisa replied, "He is a photographer and he wants to take some engagement photos of me. He asked me to wear the dress I wore to my daughter's wedding. That's how we met; he was the photographer. The dress I wore had a "V" cut in front and I guess it showed a little cleavage. Dave wants me to wear that dress for the photos but with a bra that emphasizes my cleavage a bit more." As Lisa said these last words, the blush in her chest and face began to rise again. "Oh, and he also wants me to get some sexy panties."

"Yes, you mentioned that before," Alexa replied and once again let her gaze travel Lisa's body.

She then took control and asked, "You look like about a size 10 and a 36 D or DD. Is that right?" Lisa nodded and Alexa began pulling several bra and panty sets off the rack, each one seemingly briefer than the one before. None of them looked like anything Lisa could ever imagine wearing. "Let's try these first," Alexa said, "We can use the fitting room over here." She led Lisa to an area at the back of the lingerie section with three drape covered booths located inside a small alcove with a short hallway. As they headed that direction, Alexa suddenly stopped and said, "Wait, did you bring the dress with you?"

"No, I didn't think to."

"Ok, let me see what I can find. Go ahead and try on the first set but wait for me before you try the next. I'll be right back"

Lisa went into the last booth and closed the curtain, double checking it to make sure it was closed. Then she removed her blouse and skirt followed by her bra and panties. Her breathing picked up a notch as she looked at herself in the mirror, feeling the thrill of being naked with Alexa so near. "What has gotten into you?" she asked herself in a low voice.

Lisa quickly started putting on the bra and panties set that seemed to offer the most coverage, still much less than she was used to. She had the panties on and reached for the bra when she heard Alexa say, "How is it going?" while opening the curtain a few inches. Even though her back was to the curtain, Lisa moved her hands to cover her breasts. As she did, Alexa said, "Relax Lisa, there is no one here but me."

Lisa quickly put on the bra and turned to see that Alexa had a dress in her hand, offering it to her. "Here," she said. "This may not be quite like the dress you have but it does have a "V" cut neckline and might help you see what your dress would look like with the bras you are trying on."

"Thanks," Lisa replied and quickly pulled the dress on.

"Here, let me help you get that adjusted," Alexa said and without waiting for a response, opened the curtain and started pushing and lifting Lisa's breasts, trying to set them into place in the dress.

Almost in shock, Lisa let Alexa work her magic and was soon rewarded with a "There, that's better. Look in the mirror and tell me what you think." Lisa turned to the mirror and couldn't believe it was her reflection she was seeing. The breasts she had tried for so long to hide were no longer hidden! In fact, they were very noticeable and looked—well, sexy. A quiet "Wow" escaped from her lips.

"You can say that again!" Alexa commented. "You look great; and very sexy!"

Lisa's modesty began to fight back against the excitement of seeing her boobs look so, so...Wow! Her first thought was; "You can't get that bra," followed by a naughty thought, "Of course you can; but try the others on first, they might be even hotter." Lisa stammered, "It uh, it, well, it, it looks good; but I don't think I could ever wear something like this in public."

"You said you wanted something that Dave would like, right?" Alexa reminded her. "Well he's going to love the way that bra enhances your cleavage and from what I saw, he's going to love the panties too!" "Still," she continued, "Why don't you try on a couple more before you make your decision. Get started and I'll be right back."

She left, closing the curtain behind her. Lisa removed the dress carefully and took off the bra and panties, remaining naked while looking over the remaining three sets. The first bra had some coverage but the fabric was lacy and a bit thin. The second bra was very sheer. She could see the outline of her fingers through the fabric. The third was lacy with sheerness in places, but not so much as the second. However it was very low cut, what they called a demi-bra and she was sure she her breasts would look like whale blubber in it.

Her modesty reasserting itself, she had finally settled on the first set when the curtain opened and Alexa poked her head in again. Lisa was facing Alexa and the open curtain, completely naked! She tried to cover herself and Alexa said, "Relax! You don't have anything I haven't seen before, and it's nearing closing time. Since there is no one else in the store right now, I locked the door. Besides, you have nothing to be ashamed of. At the risk of repeating myself, Dave is a lucky guy."

"He, uh, he's never seen me this way," Lisa blushingly replied.

"His loss." Alexa said. "He's gonna flip when he does. He won't be able to keep his hands off you, but then you won't want him to, will you," she said with a wink. "That's a nice set you picked, but these are really for Dave, right? Try this set on," she said, handing her the very sheer set.

Lisa quickly put on the bra and panties. She reached for the dress but before she could start to put it on, Alexa said, "Wait, let's get you adjusted in those before you put the dress on." Without waiting for a reply, she reached into the bra, and lifted first one breast, then the other, adjusting the fabric of the bra around each breast, her fingers brushing Lisa's nipples as she did.

Lisa felt her nipples begin to harden. Embarrassed and willing them to return to normal, she again reached for the dress. Once again Alexa stopped her and said, "Let me see how the panties look on you. Turn around." Her will to resist waning, Lisa slowly turned around and gasped when she saw herself in the mirror. Her nipples were poking through the bra and even the little bumps on her areolas could be seen through the thin fabric. She looked down and was shocked to see that the outline of her lips could be seen through the thin fabric of the panties even with the liner still in. Meanwhile, she realized that Alexa's hand was traveling all over her bottom as she adjusted the panties.