Tan Lines and High Heels

Edited by: Pope1944. Thanks!

***

Lew, standing in the hallway, watched his mother packing her suitcase. "Well, at least she's smiling!" he thought, a small smile on his own lips. When he and his girlfriend had hatched this plan he could have sworn that it wouldn't work. But given that they were to take a plane later today, it was clear that he had been wrong.

Shifting his eyes slightly, Lew looked at his mother like men looked at women. Just for a moment, of course. His mother was still very beautiful and sexy even though she was nearly forty. She was average size, but very curvy. Not curvy in the sense that she was chubby. Instead she was blessed with very large breasts and prominent hips, with a small waist in between. Her long brown hair, currently loose all over her back, enhanced her sexiness.

He had no idea why she was still single, three years after she broke up with Lew's dad. And the fact that she was single was the number one reason behind this crazy idea of a trip south. Lew and his girlfriend thought about that a month ago on the first day of real summer. They had been lounging on the deck, glistening with water from the pool, when they saw Lew's mother, Jessica, walking out of the house with her bikini. It was a motherly bikini, hiding a lot more skin than the bikinis his girlfriend wore, but it still showed her curves.

A few minutes later, while she was back inside to get a glass of wine, it was Lew's girlfriend who said "Damn... With a body like that, I don't understand why she's still single!" Lew grinned and quickly glanced at his girlfriend's body. While he found her very attractive, his 19 year old girlfriend looked like a child next to his mother. She added "I think I just had a good idea!"

That good idea had been to plan a trip down to some beach destination with the specific intent of putting his mother back on the dating scene. Lew had laughed and shook his head, but before he could say that it wouldn't work, Jessica walked back out and his girlfriend told her, explicitly, about her plan. Jessica laughed and blushed, but to Lew's surprise, she didn't say no. And in fact, she agreed the following day.

Now, the initial plan was for all three of them to go. Sadly, three days before departure Lew's girlfriend came down with a stomach flu. A bad stomach flu. They couldn't find anyone else to take her place and the trip turned into a mother and son thing. Lew didn't mind much, as he got a long very well with his mother. Their relationship became a lot more important after his dad left, and in the years since, mother and son had grown very close.

Shaking his head and taking his eyes off his mother's exposed cleavage, bent as she was over her suitcase, Lew walked to the living room. Thinking about it, he reflected that this closeness with his mom was a very special thing. After talking about it with his friends, he learned that none of them could talk to their moms as much as he did. When Lew told one of his closest friend that his mom had given him relationship and even some sexual advice about his girlfriend, the friend almost spat out his drink.

Sitting in the couch, Lew grinned and remembered that time when she explained a few things about women to him, on that very couch. He remembered being very uncomfortable about it at first but his mom's easy smile and relaxed attitude had calmed him down very quickly. He blushed as he remembered her hand caressing his hair as they talked. "That was normal, right?" he wondered, uncertain enough to know that he wasn't about to ask his friends about it.

Then again, normal or not, he remembered that his girlfriend, the first and only he'd had so far, had complimented him on being a very gracious and considerate virgin. He was no longer having a mind boggling sex life with her , but his mom had made a few things extremely clear and it turned out that it had worked wonders with his girlfriend.

Lew still remembered the third time they had sex. After rolling off of her, while she was still panting in post-coital bliss next to him on the bed, he had looked at her. It was the height of summer and her body was deeply tanned except for bright white lines of untanned skin. Lew loved those tan lines which highlighted the shape of her bikini. It reminded him of her sexy bikini even while she was naked. He had already liked seeing tan lines on nude models online, and he was growing to love them even more now.

In any case, in that blissful moment, his girlfriend had said "Damn! You learn so fucking quickly!" Maybe he had, but despite his raging hormones, Lew had thought that he had simply been able to keep his mother's advice in mind.

Well, it was now time for him to return this favor and encourage her to go out on dates and even have sex with a sexy latino man. Lew smiled as he remembered her reaction to those very words last week. His girlfriend had told that to his mom and instead of shaking her head, Jessica had simply blushed and giggled. Lew didn't know how serious she was about actually dating some stranger there, but to his pleasure she seemed really into it.

About twelve hours later they arrived in a land of sun, beaches and turquoise water. The small town they had chosen wasn't too touristic, keeping some of it's original charm. And easygoingness. Most of the people here, both locals and tourists, seemed remarkably relaxed. With a perpetual smile on their faces. Perfect! On their way from the small airport to their hotel, Lew saw that many men looked at his mother appreciatively. Even better!

They hadn't been able to get a switch for the rooms they had already reserved, so they would both get a room with a queen sized bed. He would sleep alone, while his mother would, hopefully, find someone to sleep with. That, after all, had been the plan. After he had unpacked and put his swim trunks on, he knocked on the door between their rooms.

When she said "Come in." Lew opened the door and stopped dead in his track. His mom was putting on her bikini. Well, it was pretty much completely on, but seeing her like this, from behind as she tied her top, took him by surprise. He had no idea why, given that he had seen his mother with that bikini many times.

Her body was already pretty tanned from all that sunbathing back home, and her skin positively glowed. Her nicely rounded ass, framed by those feminine hips, stood out right now and Lew briefly closed his eyes before looking back up. Maybe it was the place, maybe it was because they were alone in a hotel or maybe it was the fact that he knew his mom would be on the lookout for interesting men, but damn! Looking at her from behind like this made him realize just how hot she truly was! When she turned her head and upper body around, presenting him her covered left breast in the process, he swallowed.

"What's wrong?" she asked, looking at herself in the mirror.

"Nothing..." he mumbled.

"Don't lie to me young man. Why did you look at me like this? Is my bikini torn or dirty?" she asked, now fully turning around in front of him.

"No, no mom." He said, trying to hide his embarrassment as he forced himself not to look at her breasts. He took a deep breath and decided to distract her by saying "It's just that this is what I call a motherly bikini."

While it was indeed a pretty conservative bikini, he couldn't deny that it held and presented her large breasts in a very flattering way. Not lewd or indecent like a string bikini would be, but still. In the brief silence, he cleared his throat, feeling his face reddening. His mother said "What?", with a small smile on her lips.

"Well, if you're here to seduce men, I'm not sure that this will work..."

"What?" she asked again, surprised. "I'm not sexy anymore?"

"It's not that mom! It's not you, it's your bikini." Lew stammered, realizing that he had jumped from the frying pan into the fire. He was seeing his mother in an entirely new way and he didn't know how to handle that.

"Well, it's a bikini, right? How much more sexier can it get?"

Pausing for a moment, Lew then said "Did you see the girl in the red bikini downstairs?"

"Of course I did... Every man on the planet saw her!", his mom replied.

"Well, that's a sexy bikini..."

"Sure... I could sew three such bikinis form the material in mine!" Jessica laughed.

"That's... exactly my point!" Lew said.

His mom sat down on the bed, sighing, unawares of how her breasts bounced despite the sturdy frame and wide band that held the top of her bikini. "I can't wear something like that Lew... Not at my age!"

"Oh mom... Now you're fishing for compliments." Lew replied.

"No I'm not!" she replied, looking up.

"Stand up mom. Stand up and let me look at you." Lew said, shocking himself as he heard the words coming out of his mouth.

Her eyes opened slightly wider as she looked at him, but she did stand up. "Now..." he added. "Undo your hair, free it from that bun. Ok, now stand up straight, push your shoulders back... yes, like this. And now arch your back, just... so. Yep. Like that. Look at yourself mom." As she looked at herself in the mirror, Lew could see the slight surprise on her face and he relaxed when he saw the smile on her lips. "Mom. You are gorgeous. If you were to put on a bikini like the red one, every man on the planet would be looking at you instead of that little girl!"

His mom looked at him for a long moment. A long silent moment. Eventually Lew became nervous again as the moment stretched. Finally, his mom grinned and said "Are you using on me the tricks I gave you for girls, my dear son? Why are you complimenting me like this?"

"No!" Lew replied, laughing. "You're just so..." but he stopped himself. "Oh... damn. I can't say that!"

"Go ahead." his mom replied, with a serious look, staring into his eyes. "Let's suspend the normal rules for this week, alright?" his mom said.

It was clear that she needed him to say that, needed to hear what he had been about to say. Lew thought about it for a moment and took a deep breath. "You're gorgeous and extremely sexy mom. Even my girlfriend is envious of your body! I'm sure that if you get a new bikini there won't be a single man on this little island that won't be staring at you, drooling with lust."

His mom stared at him in silence again, and Lew simply couldn't decipher what he could see in her eyes. After a moment she said "Not a single one? What about you?" Lew's jaw dropped as he heard those words. But his mother laughed before he could reply. "Tell you what, mister!" she said. "I'll buy a sexier bikini if you agree to wear a speedo-type swimsuit."

"What?" Lew said, stunned.

"Well yes, If I'm going to play the sexy MILF..." Lew was shocked to hear that word from his mother, but she continued "you're also going to try something new. You're not single and looking to score like I am," again, Lew was surprised to hear those words from his mother's mouth. She continued "but I'm sure that you're going to please quite a few girls and women out there with a speedo on."

Lew didn't know that to say. Yet as he was thinking about it, he heard himself saying "OK!"

"Deal!" his mother replied, grinning. "So. I'm going to town to see if I can't find something more suitable... Even if it's so sexy that I'll have to burn it before coming back home!"

Lew's mouth went dry at the thought. After clearing his throat, he asked if she wanted him to come with. She didn't. As he was walking back to his room, Lew wondered if he would not follow her anyway to make sure that she wouldn't buy another motherly bikini. Letting himself fall on his back, he felt a smile lifting the corner of his mouth as he tried to imagine his mother wearing that red bikini...

Jessica went to the bathroom and looked at herself in the mirror. "This bikini isn't motherly, is it?" she thought, turning this way and that looking at it. "Maybe it is..." Jessica stripped down completely and took another look at her body. "Am I really sexy, even at my age? And did Lew say that he thought I was sexy?" Jessica was shocked at the lewd smile that she saw on her own face in the reflection.

She was fully aware of just how handsome and desirable her son was, had been for years. She hadn't been surprised when he came back home one day with his first girlfriend. Nor had she been surprised to see just how beautiful the girl was, content to see that her son had grabbed what was probably a very popular girl at school. And now she had just learned that he found his old mom desirable? Well then. There was hope for her yet!

Looking at herself sideways, she recognized that her breasts were still quite perky despite their size... and their age. Jessica had always been extremely proud of her breasts. Proud and grateful. It had made finding boys, then men, always a very easy exercice. Lew and his girlfriend had been right that it was high time that she try to find another man in her life. It has been years now...

Sighing, she turned to face the mirror and looked at her bush, smiling. She had seen Lew's girlfriend naked once, a few months ago, without her knowing it. Late at night, she had walked out of the bathroom naked, convinced that Jessica was sleeping. While Jessica thought that Lew's first girlfriend was pretty, she couldn't figure out why he thought such a girl with such a celery-type body was sexy. She was very thin, which seemed the norm these day, with small breasts and only hints of having any hips.

But Jessica had seen that this young girl had completely shaved her pussy. Thinking bout it now, it hadn't been a huge surprise given the current trend. Looking down at her own trimmed but still generous bush, Jessica smiled naughtily and decided to shave it off completely. Even if it would be the very first time she would do this, it wasn't simply a spur of the moment thing. Jessica had brought a clipper and razor, just in case she decided to do it. And, in any case, the sexy bikini she would buy probably wouldn't fully hide her bush in any case.

And so about thirty minutes later, Jessica was walking around in town wearing nothing but her old bikini, flip-flops and her wallet in her hand. Even though nobody could see it, the fact that her pussy was now completely bare, with nary a trace of hair anywhere between her legs and even between her buttocks, Jessica felt naked. And slightly aroused as well, she had to admit.

After asking around town, she learned that there was only two shops that would sell bikinis. When she saw the first one, clearly designed for the conservative middle age tourist type, Jessica finally admitted that her bikini was, as Lew put it, too motherly. She had in fact seen the same one in the window display, next to publicity images of much older women wearing it. She really needed something else.

Then again, when she entered the other shop, she almost laughed out loud. While it wasn't exactly a sex shop, it wasn't far from it. Determined to get rid of her old woman's bikini, she went in and tried to find something appropriate. It wasn't easy. Just for fun, she tried a few that she knew she would never buy.

First, a small bikini that seemed very sexy but still decent enough until she realize that the thin white fabric, with no backing or padding anywhere, would turn fully transparent in the water. After that she even tried a fully transparent one, feeling herself blush even trying it on and looking at herself in the mirror. Before getting back to her changing booth, she got a few glances and smiles from the young man at the counter.

She then tried the classic, over-the-top V-type of sexy swimsuit that was popular in the 80's. The bottom was held by long strings that went directly up to her breasts in front, and slipped a string between her buttocks in the back. It was utterly ridiculous, but as she looked at herself, it was clear that it was sexy. One of the bikinis she tried was even split at the crotch for easy access to her pussy!

The next one had such small triangles that it didn't fully hide her nipples. Jessica had always had large nipples, but given that they were proportionate with her even larger breasts, she had never minded. But this bikini would be completely absurd! Looking down, she saw that it barely covered her slit! "Damn! Who wears such bikinis?" she thought as she walked back to the booth.

She saw that the young man was still looking at her and she smiled at him. "As fun as this is, there's no way I'm going to buy anything from this store. Sexy is one thing, but vulgar is quite another..." she thought. Still it had been great fun! Her mood changed very rapidly when she saw that her old bikini and flip-flops were gone. She looked in the adjacent booth just in case, but no, they were gone. Most likely stolen. Luckily she had thought to keep her wallet in hand the whole time, but still...

"Damn it!" Jessica thought. Now she would have to buy a bikini from this shop just to be able to walk to the other shop. Even the thought of coming out of here and walking five or six blocks made her blush with embarrassment. Well, in any case, she wouldn't ever wear this one, even if it was to get out of here because of a fire! She giggled.

And so Jessica went back out and this time tried to find the least outrageous bikini. She finally picked one that fit the bill. It wasn't something she would have chosen, and she wold only wear it to get to the other store. Looking at herself in the mirror, she laughed nervously at the thought of getting out with it.

The bottom was very small. Very. It hid her pussy, but just so. It was an American-flag themed bikini, and the bottom had red and white stripes going down in the same direction as her slit. It was, at most, three inches wide at the top. From the corners, two fine strings wrapped around her hips and met a third string on her lower back. Of course it was a string bikini, something she had never worn in her life. In fact, Jessica hadn't even worn such a thing for panties!

Up top, the two triangles were blue with white stars on it, as if to attract even more attention to her breasts. There was even a big white star above each of her nipples! It was the biggest top she had found, yet it didn't cover much of her breasts. She could still see much of the outlines of her breasts in the middle and a whole damn lot of those outlines on either side. The top wasn't quite wide enough, and so the outside curves of her breasts were more exposed than usual. In fact, she felt like her breasts could pop out at any moment! More than half of her breasts were visible!

And finally, there was something else that was very visible. Her tan lines. Even before arriving here, Jessica had already had a decent tan. A tan with very clear white demarcations where her old bikini had been. As she had been trying on other bikinis, she had seen them, obviously, but given that she hadn't had any intention of actually buying any of them, she hadn't cared about the white lines on her smooth skin. Now, those lines were unmistakable.

And, even to her eyes, extremely sexy. Somehow it enhanced the effect of the small bikini, attracting her eyes even more. And she knew that the contrast between her golden and white skin, especially in conjunction with the American colors of her bikini, would grab the attention of all the men who would see her like this. Christ! Jessica sighed as she looked at her reflection: huge breasts, tiny bikini, bright white tan lines... This was an unholy and naughty combination!

And it wasn't just a white outline around her breasts! Looking down, she saw the same white tan lines around her pussy and all around to her hips. Turning around, she gasped as she saw how her white ass was mercilessly exposed! "Fuck!" she breathed. The string hid absolutely nothing and her bright white buttocks would shine like a fucking beacon fire in the night! Thankfully, she knew she still had a nice and relatively firm ass. Nevertheless... she had never exposed it so brazenly in her entire life! Not even when she was at her physical prime in her twenties!